JP2010100594A - Nonionic surfactant, and cosmetic product and preparation for external use using the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide novel derivatives of polyoxyalkylene dimer acid and polyoxyalkylene dimer diol ester, and to provide a cosmetic product and a preparation for external use which blend them and are excellent in safety, stability, and sense of use. <P>SOLUTION: The cosmetic product and the preparation for external use includes at least one nonionic surfactant which is a nonionic surfactant composition obtained by an esterification reaction of hydroxyl groups of both ends of polyoxyalkylene dimer acid and polyoxyalkylene dimer diol (2-3C alkylene) with a fatty acid, and is chosen from a group consist of a polyoxyalkylene dimer acid ester derivative and a polyoxyalkylene dimer diol ester derivative of structures shown in the figure. <P>COPYRIGHT: (C)2010,JPO&INPIT

Description

  The present invention relates to a nonionic surfactant, a cosmetic using the same, and an external preparation.

  Conventionally, nonionic surfactants containing polyoxyalkylene / higher alcohol ethers and polyoxyalkylene higher fatty acid esters have been used in cosmetics and external preparations. For example, polyoxyethylene (hereinafter abbreviated as “POE”)-nonylphenol ether, POE-octylphenol ether, POE-stearyl ether, POE-oleyl ether, POE-oleic acid ester, POE-stearic acid ester and the like are cosmetics and external preparations. Is used. (For example, see Patent Documents 1 and 2). Further, for example, Patent Document 3 describes that POE-dimer diol and POE-dimer acid are used as nonionic surfactants and give excellent functionality to cosmetics and external preparations.

JP 2006-76899 A JP 2006-182703 A JP 2008-115091 A

  However, these nonionic surfactants are not always satisfactory in terms of safety, stability, feeling of use and the like as raw materials for cosmetics and external preparations. Therefore, a raw material that is further excellent in safety, stability, feeling in use, pigment dispersibility, solubilization performance, odor and the like is desired. As a result of intensive studies to achieve the above-mentioned problems, the present inventors have esterified the hydroxyl groups at both ends of a compound obtained by adding polyoxyalkylene oxide (C2 to C3) to dimer acid and dimer diol. The present inventors have found that the nonionic surfactant containing a new derivative obtained in this way is excellent in safety, stability, feeling of use and the like as a raw material for cosmetics and external preparations.

  The present invention relates to hydroxyl groups at both ends of a compound obtained by adding polyoxyalkylene oxide (polymerized with alkylene oxide having 2 to 3 carbon atoms (hereinafter referred to as “C2 to C3”)) to dimer acid and dimer diol. The present invention provides a nonionic surfactant containing a new derivative obtained by esterification reaction of a fatty acid with a fatty acid. The present invention further provides cosmetics and external preparations that are excellent in safety, stability, feeling of use and the like, containing the nonionic surfactant.

（但し、式中、Ｒ，Ｒ’は水素または脂肪酸残基、ａ，ｂ，ｃ，ｄは１以上の整数でａ＋ｂ＋ｃ＋ｄ＝１２〜４０の範囲である。また、(ＡＯ)、(ＡＯ’)がＣ２からＣ３の単一アルキレンオキシド付加重合体である。また、(ＡＯ)、(ＡＯ’)がＣ２とＣ３のアルキレンオキシドのブロックまたはランダム付加重合体である。ｎ＋ｎ’はアルキレンオキシドの平均付加モル数を示し、１〜２００の整数である。また、ＲＯ、Ｒ’Ｏはエステル化度によりモノエステル化合物、セスキエステル化合物、ジエステル化合物となる。）

（但し、式中、Ｒ，Ｒ’は水素または脂肪酸残基、ｅ，ｆ，ｇ，ｈは１以上の整数でｅ＋ｆ＋ｇ＋ｈ＝１２〜４０の範囲である。また、(ＡＯ)、(ＡＯ’)がＣ２またはＣ３の単一アルキレンオキシド付加重合体である。また、(ＡＯ)、(ＡＯ’)がＣ２とＣ３のアルキレンオキシドのブロックまたはランダム付加重合体である。ｎ＋ｎ’はアルキレンオキシドの平均付加モル数を示し、１〜２００の整数である。また、ＲＯ、Ｒ’Ｏはエステル化度によりモノエステル化合物、セスキエステル化合物、ジエステル化合物となる。） (1) A nonionic surfactant composition obtained by esterifying a hydroxyl group at both ends of a polyoxyalkylene dimer acid or polyoxyalkylene dimer diol (alkylene carbon number C2 to C3) with a fatty acid, A nonionic surfactant composition comprising at least one selected from the group consisting of a polyoxyalkylene dimer acid ester derivative and a polyoxyalkylene dimer diol ester derivative having the structure shown below.

(In the formula, R and R ′ are hydrogen or fatty acid residues, a, b, c and d are integers of 1 or more and a + b + c + d = 12 to 40. Also, (AO), (AO ′) Is a single alkylene oxide addition polymer of C2 to C3, and (AO), (AO ′) is a block or random addition polymer of alkylene oxides of C2 and C3, n + n ′ is the average addition of alkylene oxide This represents the number of moles and is an integer of 1 to 200. RO and R′O are monoester compounds, sesquiester compounds, and diester compounds depending on the degree of esterification.)

(In the formula, R and R ′ are hydrogen or fatty acid residues, e, f, g and h are integers of 1 or more and are in the range of e + f + g + h = 12 to 40. Also, (AO), (AO ′) Is a single alkylene oxide addition polymer of C2 or C3, and (AO), (AO ′) is a block or random addition polymer of C2 and C3 alkylene oxide, n + n ′ is the average addition of alkylene oxide This represents the number of moles and is an integer of 1 to 200. RO and R′O are monoester compounds, sesquiester compounds, and diester compounds depending on the degree of esterification.)

  (2) A nonionic surfactant composition obtained by esterifying a hydroxyl group at both ends of a polyoxyalkylene dimer acid or polyoxyalkylene dimer diol (carbon number C2-C3 of alkylene) with a fatty acid, A cosmetic comprising a nonionic surfactant composition comprising at least one selected from the group consisting of polyoxyalkylene dimer acid ester derivatives and polyoxyalkylene dimer diol ester derivatives having the structures shown in Chemical Formula 1 and Chemical Formula 2 above. is there.

  (3) A nonionic surfactant composition obtained by esterifying a hydroxyl group at both ends of a polyoxyalkylene dimer acid or polyoxyalkylene dimer diol (carbon number C2-C3 of alkylene) with a fatty acid, An external preparation containing a nonionic surfactant composition comprising at least one selected from the group consisting of polyoxyalkylene dimer acid ester derivatives and polyoxyalkylene dimer diol ester derivatives having the structures shown in Chemical Formula 1 and Chemical Formula 2 above. is there.

  One or more nonionic surfactant compositions of the reoxyalkylene dimer acid ester derivative and the polyoxyalkylene dimer diol ester derivative according to the present invention are more excellent in emulsion stability than conventional nonionic surfactants.

  Cosmetics and external preparations containing as active ingredients one or more nonionic surfactant compositions of polyoxyalkylene dimer acid ester derivatives and polyoxyalkylene dimer diol ester derivatives according to the present invention are excellent in safety, and more functional It can be made excellent.

  Hereinafter, the present invention will be described in detail.

  The polyoxyalkylene dimer acid used in the polyoxyalkylene dimer acid ester derivative represented by the above chemical formula 2 used in the present embodiment is a known dibasic acid obtained by intermolecular polymerization of unsaturated fatty acids with a carbon number of C2. ˜C3 alkylene oxide (that is, ethylene oxide or propylene oxide) is subjected to addition polymerization.

  The industrial production process of dimer acid, a known dibasic acid, is almost standardized in the industry. For example, dimer acid and its lower alcohol ester can be obtained by dimerizing an unsaturated fatty acid having 11 to 22 carbon atoms or its lower alcohol ester with a clay catalyst. The dimer acid obtained industrially is mainly composed of a dibasic acid having about 36 carbon atoms, but contains an arbitrary amount of trimer acid and monomer acid depending on the degree of purification. In general, dimer acid content of over 70% by mass and dimer acid content increased to 90% by mass or more by molecular distillation are in circulation. Although a double bond remains after the dimerization reaction, a hydrogen bond that has been further hydrogenated to improve oxidation stability is on the market. In the present invention, any dimer acid currently in circulation can be used.

  The polyoxyalkylene dimer diol used in the polyoxyalkylene dimer diol ester derivative represented by the above chemical formula 2 used in the present embodiment reduces a known dibasic acid obtained by intermolecular polymerization of unsaturated fatty acids. To the compound obtained by addition polymerization of C2-C3 alkylene oxide.

  The dimer diol obtained industrially contains other components such as trimmer triol, monoalcohol and ether compound depending on the degree of purification of the above-mentioned dimer acid used as a raw material and its lower alcohol ester. Generally, any dimer diol content exceeding about 70% by mass can be used in the present invention, but a high-purity dimer diol, for example, a dimer diol content exceeding 90% by mass is preferred. In addition, dimer diols are distributed from animal fats and vegetable fats, but those derived from plants are desirable.

  The alkylene oxide is not particularly limited as long as it has C2 to C3 carbon atoms, but preferably has C2 carbon atoms. Examples of the alkylene oxide used in the present invention include ethylene oxide and propylene oxide.

  The polyoxyalkylene dimer acid ester derivative or polyoxyalkylene dimer diol ether ester derivative contained in the nonionic surfactant of the present invention is a dimer acid or a hydroxyl group at both ends of a compound obtained by adding an alkylene oxide to a dimer diol. (For example, caprylic acid, stearic acid, isostearic acid, palmitic acid, isopalmitic acid, myristic acid, oleic acid, linoleic acid, lauric acid, erucic acid, behenic acid, ricinoleic acid, hydroxystearic acid, polyhydroxystearic acid, etc.) And the esterification reaction compound. In the nonionic surfactant of the present invention, it is particularly preferable to use isostearic acid because the effects of the present invention are excellent when isostearic acid is used.

  The synthesis conditions of the polyoxyalkylene dimer acid ester derivative and polyoxyalkylene dimer diol ester derivative contained in the nonionic surfactant of the present invention were as follows: polyoxyalkylene dimer acid and polyoxyalkylene dimer diol and an arbitrary amount of fatty acid (isostearin). Acid, hydroxystearic acid, polyhydroxystearic acid), and the esterification reaction is performed at 230 ° C. to 260 ° C., preferably 250 ° C. in a nitrogen atmosphere. By changing the charge ratio of polyoxyalkylene dimer acid or polyoxyalkylene dimer diol and fatty acid, the esterification degree of the resulting ester can be arbitrarily adjusted between monoester and diester.

  The polyoxyalkylene dimer acid ester derivative and the polyoxyalkylene dimer diol ether of the present invention can be made into various types of ester compounds depending on the purpose of development. That is, by selecting the type of fatty acid, selecting a combination of two or more different fatty acids, selecting raw materials for dimer acid and dimer diol, selecting an alkylene oxide and its addition amount, an ester having desired characteristics can be obtained. Obtainable.

  Polyoxyalkylene dimer acid and ester of polyoxyalkylene dimer diol and fatty acid can be selected by appropriately selecting the raw materials, viscosity, state (solid, soft wax, liquid, etc.), IOB value (= inorganic value / organic) Property value) and compatibility with other components (compatibility, etc.) can be arbitrarily adjusted, and a cosmetic and an external preparation excellent in feel and stability can be provided.

  Substances obtained by esterifying fatty acids (eg, isostearic acid, hydroxystearic acid, polyhydroxystearic acid) into a raw material obtained by addition-polymerizing only ethylene oxide as alkylene oxide to dimer acid has improved lipophilicity compared to before the esterification reaction. did. Also, the obtained polyoxyethylene (hereinafter abbreviated as “POE”) (EO is mol) dimer acid ester compound is an addition amount of ethylene oxide, the degree of esterification, and the appearance is liquid to solid, emulsified and solubilized. We have been able to develop a wide variety of products from strong to weak, silicon oil-soluble. The amount of ethylene oxide added is preferably 1 mol to 200 mol of ethylene oxide to 1 mol of dimer acid, and more preferably 2 mol to 100 mol of ethylene oxide is added to 1 mol of dimer acid. That is.

  A substance obtained by esterifying a fatty acid (for example, isostearic acid, hydroxystearic acid, polyhydroxystearic acid) into a raw material obtained by addition polymerization of only propylene oxide as an alkylene oxide to dimer acid is more lipophilic than before the esterification reaction. Improved. The obtained polyoxypropylene (hereinafter abbreviated as “POP”) dimer acid ester compounds were all lipophilic nonionic surfactants. The amount of propylene oxide added is preferably 1 mol to 200 mol of propylene oxide with respect to 1 mol of dimer acid, more preferably 2 mol to 100 mol of propylene oxide with respect to 1 mol of dimer acid. Is to add.

  A substance obtained by esterifying a fatty acid with a raw material obtained by block- and random-polymerizing ethylene oxide and propylene oxide as alkylene oxide into dimer acid has improved lipophilicity than before the esterification reaction. The resulting POP + POE dimer acid ester compounds are developed in a wide variety of forms, from those with a liquid appearance to those with a solid appearance, those with strong emulsification and solubilization performance, and those with weakness, depending on the amount of ethylene oxide addition, propylene oxide addition and esterification. did it. The addition amount of alkylene oxide is preferably 1 to 50 mol of propylene oxide and 2 to 100 mol of ethylene oxide, more preferably 1 to 10 mol of propylene oxide, and 2 to 100 mol of ethylene oxide with respect to 1 mol of dimer acid. It is to add in the range of mole.

  Substances obtained by transesterifying fatty acids (for example, isostearic acid, hydroxystearic acid, polyhydroxystearic acid) into a raw material obtained by addition-polymerizing only ethylene oxide as an alkylene oxide to dimer diol are more lipophilic than before the esterification reaction. Improved. Also, the obtained polyoxyethylene (hereinafter abbreviated as “POE”) (EO is mol) dimer diol ester compound is from the liquid appearance to the solid, emulsification and solubilization depending on the amount of ethylene oxide addition and esterification We have been able to develop a wide variety of products from strong to weak, silicon oil-soluble. The amount of ethylene oxide added is preferably from 1 mol to 200 mol, more preferably from 2 mol to 100 mol, per mol of dimer diol.

  A substance obtained by esterifying a fatty acid (for example, isostearic acid, hydroxystearic acid, polyhydroxystearic acid) to a raw material obtained by addition-polymerizing only propylene oxide as an alkylene oxide to dimer diol is more lipophilic than before the esterification reaction. Improved. Further, the obtained polyoxypropylene (hereinafter abbreviated as “POP”) dimer diol ester compounds were all lipophilic nonionic surfactants. The amount of propylene oxide added is preferably 1 mol to 200 mol, more preferably 2 mol to 100 mol, of propylene oxide with respect to 1 mol of dimer diol.

  Substances obtained by esterifying fatty acids (eg, isostearic acid, hydroxystearic acid, polyhydroxystearic acid) into raw materials obtained by block polymerization and random polymerization of ethylene oxide and propylene oxide as alkylene oxides to dimer diol are more effective than before the esterification reaction. Improved lipophilicity. The resulting POP + POE dimer diol ester compounds are developed in a wide variety from the liquid appearance to the solid, the emulsification and solubilization performance to the weak, depending on the amount of ethylene oxide addition, propylene oxide addition and esterification. did it. The addition amount of alkylene oxide is preferably 1 to 50 mol of propylene oxide and 2 to 100 mol of ethylene oxide with respect to 1 mol of dimer diol, more preferably 1 to 10 mol of propylene oxide and 2 to 100 of ethylene oxide. The range of moles.

  Dimer acid and dimer diol have a molecular weight twice that of conventional higher fatty acids and higher alcohols, and their alkylene oxide addition polymers, as well as compounds obtained by esterification with fatty acids, are safe, stable, It is excellent in touch and the like, and by blending it, a cosmetic and an external preparation with good safety and excellent use feeling can be provided.

  Although the compounding quantity of the nonionic surfactant of this invention to cosmetics and a skin external preparation is not specifically limited, About 0.1 mass%-50 mass% are desirable, More preferably, 0.5 mass%-30 mass %.

  One or more polyoxyalkylene dimer acid ester derivatives or polyoxyalkylene dimer diol ester derivatives used in the present embodiment, cleansing oil, facial cleansing foam, cleansing cream, cleansing gel, massage cream, cold cream, emollient cream, Moisture cream, hand cream, emollient emulsion, moisture emulsion, hand emulsion, lotion, pack, foundation, lipstick, press powder, eye shadow, tic, hair liquid, set lotion, permanent wave solution, hair cream, hair lotion, hair mousse, Hair wax, hair gel, shampoo, hair rinse, hair conditioner, body shampoo, solid detergent, liquid detergent, antiperspirant, af Over shaving cream, sunscreen cream, sunscreen oils, hair tonics, hair tonic, bath agents, can be used as a nonionic surfactant upon adjustment of cosmetics and external preparations such as external pharmaceutical composition. There are no particular restrictions on the dosage forms of cosmetics and external preparations, and any emulsification system, solubilization system, solution system, powder dispersion system, water-oil two-layer system, water-oil-powder three-layer system, etc. It may be a dosage form.

  The cosmetics and external preparations of the present embodiment include, as oil phase raw materials, saturated or unsaturated fatty acids and higher alcohols obtained therefrom, squalane, castor oil and derivatives thereof, lanolins including beeswax, liquid and refined lanolin, and Derivatives thereof, cholesterol and derivatives thereof, macadamia nut oil, jojoba oil, carnauba wax, sesame oil, cacao oil, palm oil, mink oil, owl, candelilla wax, whale wax and other oil phase raw materials, paraffin, microcrystalline wax, Oil phase raw materials derived from petroleum and minerals such as liquid paraffin, petrolatum, ceresin, methylpolysiloxane, polyoxyethylene / methylpolysiloxane, polyoxypropylene / methylpolysiloxane, poly (oxyethylene / oxypropylene) / methylpolysiloxane S , Silicones such as silicone polymers such as methylphenyl polysiloxane, fatty acid-modified polysiloxane, aliphatic alcohol-modified polysiloxane, amino acid-modified polysiloxane, resin acids, esters, ketones, oily components, The polyoxyalkylene dimer acid ester or polyoxyalkylene dimer diol ester of the present invention can be used in combination as long as the effect as a nonionic surfactant is not impaired.

  In addition, the cosmetics and external preparations of the present embodiment include the polyoxyalkylene dimer acid ester and the polyoxyalkylene dimer diol ester used in the present embodiment or the nonionic surfactant composition as long as they do not inhibit the effect. Other surfactants include N-long chain acyl amino acid salts such as N-long chain acyl acidic amino acid salts and N-long chain acyl neutral amino acid salts; N-long chain fatty acid acyl-N-methyl taurine salts, alkyls Sulfates and alkylene oxide adducts, fatty acid amide ether sulfates, fatty acid metal salts and weak bases, sulfosuccinic acid surfactants, alkyl phosphates and their alkylene oxide adducts, anionic surfactants such as alkyl ether carboxylic acids; higher alcohols And ethers such as alkylene oxide adducts thereof Nonionic surfactants; ether ester type nonionic surfactants such as glycerin esters and sorbitan esters and alkylene oxide adducts thereof; polyoxyalkylene fatty acid esters, glycerin esters, fatty acid polyglycerin esters, N-long chain acyl peptide polyglycerin esters , Surfactant esters such as sorbitan esters and sucrose fatty acid esters; nonionic surfactants such as alkyl glucosides, hydrogenated castor oil pyroglutamic acid diester and its ethylene oxide adducts, and fatty acid alkanolamides; Aliphatic amine salts such as ammonium chloride and dialkyl ammonium chloride, quaternary ammonium salts thereof, aromatic quaternary ammonium salts such as benzalkonium salt, fatty acid acid Various surfactants such as cationic surfactants such as arginine esters; betaine surfactants such as carboxybetaine; amphoteric surfactants such as aminocarboxylic acid type surfactants and imidazoline type surfactants are also included in the present invention. In addition to the polyoxyalkylene dimer acid ester and polyoxyalkylene dimer diol ester or nonionic surfactant composition thereof.

  Furthermore, the cosmetics and external preparations of the present embodiment include, as an aqueous phase component, amino acids such as glycine, alanine, serine, threonine, arginine, glutamic acid, aspartic acid, leucine, and valine; glycerin, ethylene glycol, 1, Polyhydric alcohols such as 3-butylene glycol, propylene glycol and dipropylene glycol; polyamino acids including polyglutamic acid and polyaspartic acid and salts thereof, polyethylene glycol, gum arabic, alginate, xanthan gum, hyaluronic acid, hyaluronic acid salt, Chitin, chitosan, water-soluble chitin, carboxyvinyl polymer, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropyltrimethylammonium chloride, polydimethylmethylenepiperidi , Quaternary ammonium of polyvinylpyrrolidone derivatives, cationized protein, collagen degradation product and derivatives thereof, water-soluble polymers such as acylated protein, polyglycerol, amino acid polyglycerol ester; sugar alcohols such as mannitol and alkylene oxide adducts thereof; In addition, lower alcohols such as ethanol and propanol can be blended.

  Furthermore, examples of additives and medicines that are blended in the cosmetics and external preparations of the present embodiment include those that are usually blended in cosmetics and external preparations. For example, preservatives such as paraben derivatives, fragrances, pigments, pearlizing agents, antibacterial agents, antibacterial agents, anti-inflammatory agents, analgesics, antifungal agents, keratin softening and release agents, UV protection agents, hair restorers, whitening agents, Antiperspirants, sweat deodorants, vitamins, pH adjusters, hormone agents, viscosity adjusters, herbal medicines and the like can be blended.

  Contains the above POE (nmol) dimer acid ester and POE (n mol) dimer diol ester or one or more active ingredients to be blended in cosmetics and external preparations prepared by appropriately blending the above ingredients The amount of the nonionic surfactant to be used varies depending on the product form, but is usually 0.01 to 100% by mass (the nonionic surfactant composition of the present invention is added with other components as, for example, makeup remover) And can be used as it is, preferably 0.1 to 50% by mass.

  One embodiment of the present invention will be described below, but the present invention is not limited thereto. In the examples, unless otherwise specified, “part” represents “part by mass” and “%” represents “% by mass”.

Example 1: Synthesis of POE (20 mol) dimer acid;
750 g of dimer acid “Pripol 1009; made by Unikema” is charged and stirred, and the temperature is raised while introducing nitrogen. When the temperature is raised to 80 ° C., 3.0 g of potassium hydroxide is added. Further, the temperature is raised to 130 ° C. to start addition of ethylene oxide, and the reaction is conducted at a reaction temperature of 160 to 165 ° C. When 585 g of ethylene oxide was added in a reaction time of 2 hours, it was cooled with water and neutralized at 110 to 120 ° C. with 6 ml of 50% aqueous citric acid solution. PEO (20 mol) dimer acid of AO = ethylene oxide, n + n ′ = 20, R = H, R ′ = H in the above [Chemical Formula 1] of the above-mentioned [Chemical Formula 1] of EO adduct by precoat filtration using diatomaceous earth. Obtained.

  As a result of analysis of this product, it was a compound having an acid value of 0.51, a hydroxyl value of 111.75, a saponification value of 115.34, and an HLB value = 8.3.

As a result of carrying out infrared absorption spectrum measurement about this compound, characteristic absorption was recognized by wavelength 3469.94cm < ^-1 > (hydroxyl group), 1737.86cm < ^-1 > (ester), and 1122.57cm < ^-1 > (ether).

Example 2: Synthesis of POE (20 mol) dimer acid monofatty acid ester compound;
Next, fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid per mole of the POE dimer acid obtained in Example 1 Each of “K-PON306; manufactured by Ogura Gosei Kogyo Co., Ltd.” was charged at a rate of 1 mole, and the esterification reaction was performed at a reaction temperature of 250 ° C. for 6.5 to 8 hours while introducing nitrogen. In the above [Chemical Formula 1], AO = ethylene oxide, n + n ′ = 20, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R A POE (20 mol) dimer acid monofatty acid ester compound in which '= H 2 was obtained.

  As a result of analysis of these products, isostearic acid ester compound: acid value 3.2, hydroxyl value 32.85, saponification value 100.67, HLB value = 8.7, hydroxystearic acid ester compound: acid value 3.29. , Hydroxyl value 67.62, saponification value 100.87, HLB value = 9.3, polyhydroxystearic acid ester compound: acid value 10.28, hydroxyl value 19.99, saponification value 142.59, HLB value = It was 5.5 compound.

As a result of measuring the infrared absorption spectrum of each of the compounds, isostearic acid ester compounds: wavelengths 3489.38 cm ⁻¹ (hydroxyl group), 1736.97 cm ⁻¹ (ester) and 1115.87 cm ⁻¹ (ether), hydroxystearic acid Ester compound: Wavelength 3489.38 cm ⁻¹ (hydroxyl group), 1736.01 cm ⁻¹ (ester) and 111.90 cm ⁻¹ (ether), polyhydroxystearic acid ester compound: wavelength 3455.62 cm ⁻¹ (hydroxyl group), 1735. Characteristic absorption was observed in 04 cm ⁻¹ (ester) and 1113.94 cm ⁻¹ (ether).

Example 3: Synthesis of POE (1 to 200 mol) dimer acid monofatty acid ester compound;
By operating in the same manner as in Example 1, the addition reaction time of ethylene oxide (hereinafter also referred to as “EO”) was controlled on the dimer acid “Pripol (Puripol) 1009; made by Unikema”, and the number of moles of EO addition was changed. In the same manner as in Example 2, fatty acids [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Kokura Gosei Kogyo”, polyhydroxystearic acid “K-PON306; Kokura Gosei Kogyo” Any one of “made by the manufacturer”], and the nonionic surfactant (1) [POE addition moles (EO is 1 to 200 mol)] in the above [Chemical Formula 1], AO = ethylene oxide, n + n ′ = 1 to 200, R = fatty acid residue (each fatty acid residue used in the esterification reaction), POE (1 to R ′ = H 2) 00 mol) was obtained dimer acid mono fatty acid ester compound.

  As a result of analysis of these products, for example, POE (60 mol) dimer acid monohydroxystearate compound has an acid value of 6.01, a hydroxyl value of 39.79, a saponification value of 54.45, and an HLB value of 13.6. It was a compound.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, the POE (60 mol) dimer acid monohydroxystearate compound has characteristic absorption at wavelengths of 3498.06 cm ⁻¹ (hydroxyl group), 1735.04 cm ⁻¹ (ester) and 1111.297 cm ⁻¹ (ether). .

Example 4: Synthesis of POE (40 mol) dimer acid monostearate compound;
1 mol (1670 g) of POE (40 mol) dimer acid obtained by the same operation as in Example 1 is 1 mol (330 g) of isostearic acid “EMERSOL874; manufactured by Cognis Japan” as a fatty acid. Then, the esterification reaction was carried out at a reaction temperature of 250 ° C. for 7 hours while introducing nitrogen, and 1955.3 g (yield 97.8%) of the nonionic surfactant (1) of the present invention, 1], a POE (40 mol) dimer acid monoisostearate ester having AO = ethylene oxide, n + n ′ = 40, R = isostearate group, and R ′ = H was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 5.38, a hydroxyl value of 23.03, a saponification value of 72.81, and an HLB value = 11.8.

As a result of measuring the infrared absorption spectrum of this compound, characteristic absorption was observed at wavelengths of 3489.38 cm ⁻¹ (hydroxyl group), 1736.97 cm ⁻¹ (ester), and 11113.94 cm ⁻¹ (ether).

Example 5: Synthesis of POE (20 mol) dimer acid sesqui fatty acid ester compound;
Fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid “K” per mole of the POE dimer acid obtained in Example 1 -PON306; manufactured by Ogura Gosei Kogyo Co., Ltd.] was added at a ratio of 1.5 mol, and the esterification reaction was carried out at a reaction temperature of 250 ° C. for 5 to 8 hours while introducing nitrogen. Nonionic surfactant (1) of the invention, that is, in the above [Chemical Formula 1], AO = ethylene oxide, n + n ′ = 20, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid A POE (20 mol) dimer acid sesqui fatty acid ester compound having a residue: H ratio of 1: 1 was obtained.

  As a result of analysis of these products, for example, a POE (20 mol) dimer acid sesquiisostearate compound has an acid value of 5.56, a hydroxyl value of 15.23, a saponification value of 111.03, and an HLB value of 7.9. Met.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, the POE (20 mol) dimer acid sesquiisostearate ester compound showed characteristic absorption at wavelengths of 3482.63 cm ⁻¹ (hydroxyl group), 1737.94 cm ⁻¹ (ester) and 1115.87 cm ⁻¹ (ether).

Example 6: Synthesis of POE (1 to 200 mol) dimer acid sesqui fatty acid ester compound;
By operating in the same manner as in Example 1, the addition reaction time of ethylene oxide (hereinafter also referred to as “EO”) was controlled on the dimer acid “Pripol (Puripol) 1009; made by Unikema”, and the number of moles of EO addition was changed. In the same manner as in Example 5, fatty acids [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Kokura Gosei Kogyo”, polyhydroxystearic acid “K-PON306; Kokura Gosei Kogyo” Any one of “made by the manufacturer”], and the nonionic surfactant (1) [POE addition moles (EO is 1 to 200 mol)] in the above [Chemical Formula 1], AO = ethylene oxide, n + n ′ = 1 to 200, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid residue (ester Each fatty acid residue used in the reaction): The ratio of H 1: a is to obtain a POE (1 to 200 moles) of dimer acid sesqui fatty ester compound 1.

  As a result of analysis of these products, for example, POE (40 mol) dimer acid sesquiisostearate compound is a compound having an acid value of 8.39, a hydroxyl value of 13.22, a saponification value of 81.3, and an HLB value of 11.0. there were.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, the POE (40 mol) dimer acid sesquiisostearic acid ester compound showed characteristic absorption at wavelengths of 3482.63 cm ⁻¹ (hydroxyl group), 1736.97 cm ⁻¹ (ester) and 111.90 cm ⁻¹ (ether).

Example 7: Synthesis of POE (60 mol) dimer acid sesquiisostearate compound;
A ratio of 1.5 mol (240 g) of isostearic acid “EMERSOL874; manufactured by Cognis Japan” as a fatty acid to 1 mol (1260 g) of POE (60 mol) dimer acid obtained by the same operation as in Example 1. The non-ionic surfactant (1) of the present invention (1) 1437.3 g (yield 95.8%) was prepared by carrying out an esterification reaction at a reaction temperature of 250 ° C. for 7 hours and 30 minutes while flowing nitrogen. That is, in the above [Chemical Formula 1], the ratio of AO = ethylene oxide, n + n ′ = 60, R = isostearic acid ester group, R ′ = isosteric acid ester group: H is 1: 1, POE (60 mol) dimer acid sesquiisostearin. The acid ester was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 9.03, a hydroxyl value of 18.36, a saponification value of 62.26, and an HLB value = 12.7.

As a result of measuring the infrared absorption spectrum of this compound, characteristic absorption was observed at wavelengths of 3489.38 cm ⁻¹ (hydroxyl group), 1736.97 cm ⁻¹ (ester), and 1112.97 cm ⁻¹ (ether).

Example 8: Synthesis of POE (20 mol) dimer acid difatty acid ester compound;
Fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid “K” per mole of the POE dimer acid obtained in Example 1 -PON306; manufactured by Ogura Gosei Kogyo Co., Ltd.] was added at a ratio of 2 moles, and the esterification reaction was performed at a reaction temperature of 250 ° C. for 5 to 8 hours while introducing nitrogen. Nonionic surfactant (1), that is, in the above [Chemical Formula 1], AO = ethylene oxide, n + n ′ = 20, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid residue A POE (20 mol) dimer acid difatty acid ester compound which is a group (each fatty acid residue used in the esterification reaction) was obtained.

  As a result of analysis of these products, for example, POE (20 mol) dimer acid diisostearate compound is a compound having an acid value of 8.72, a hydroxyl value of 10.41, a saponification value of 114.97, and an HLB value of 7.2. there were.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, the POE (20 mol) dimer acid diisostearate ester compound showed characteristic absorption at wavelengths of 1737.94 cm ⁻¹ (ester) and 1115.87 cm ⁻¹ (ether).

Example 9: Synthesis of POE (1-200 mol) dimer acid difatty acid ester compound;
By operating in the same manner as in Example 1, the addition reaction time of ethylene oxide (hereinafter also referred to as “EO”) was controlled on the dimer acid “Pripol (Puripol) 1009; made by Unikema”, and the number of moles of EO addition was changed. In the same manner as in Example 8, fatty acids [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Kokura Gosei Kogyo”, polyhydroxystearic acid “K-PON306; Kokura Gosei Kogyo” Any one of “made by the manufacturer”], and the nonionic surfactant (1) [POE addition moles (EO is 1 to 200 mol)] in the above [Chemical Formula 1], AO = ethylene oxide, n + n ′ = 1 to 200, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid residue (ester Used in the reaction is the fatty acid residues) to give a POE (1 to 200 moles) Dimer acid di fatty acid ester compound.

  As a result of analysis of these products, for example, POE (40 mol) dimer acid diisostearate compound is a compound having an acid value of 11.68, a hydroxyl value of 15.54, a saponification value of 87.32, and an HLB value of 11.2. there were.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, the POE (40 mol) dimer acid diisostearate ester compound showed characteristic absorption at wavelengths of 1736.01 cm ⁻¹ (ester) and 111.90 cm ⁻¹ (ether).

Example 10: Synthesis of POE (4 mol) dimer acid diisostearate compound;
2 moles (540 g) of isostearic acid “EMERSOL874; manufactured by Cognis Japan” as a fatty acid with respect to 1 mole (660 g) of POE (4 moles) dimer diol obtained by the same operation as in Example 1. The non-ionic surfactant of the present invention (1) 1146.0 g (yield 95.5%), that is, the above, In [Chemical Formula 1], a POE (4 mol) dimer acid sesquiisostearate ester in which AO = ethylene oxide, n + n ′ = 4, R = isostearic acid ester group, and R ′ = isosteric acid ester group was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 16.29, a hydroxyl value of 30.78, a saponification value of 174.9, and an HLB value = 3.0.

As a result of measuring the infrared absorption spectrum of this compound, characteristic absorption was observed at wavelengths of 1740.83 cm ⁻¹ (ester) and 1171.81 cm ⁻¹ (ether).

Example 11: Synthesis of POE (60 mol) dimer acid diisostearate compound;
2 moles (270 g) of isostearic acid “EMERSOL874; manufactured by Cognis Japan” as a fatty acid with respect to 1 mole (1230 g) of POE (60 moles) dimer acid obtained by the same operation as in Example 1. In each case, the esterification reaction was carried out at a reaction temperature of 250 ° C. for 7 hours and 30 minutes while flowing nitrogen, and the nonionic surfactant (1) of the present invention (1) 1472.8 g (yield 98.2%), that is, the above In [Chemical Formula 1], POE (60 mol) dimer acid diisostearate ester in which AO = ethylene oxide, n + n ′ = 60, R = isostearic acid ester group, and R ′ = isostearic acid ester group was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 10.54, a hydroxyl value of 14.22, a saponification value of 65.64, and an HLB value = 12.8.

As a result of measuring the infrared absorption spectrum of this compound, characteristic absorption was observed at a wavelength of 1736.97 cm ⁻¹ (ester) and 1112.97 cm ⁻¹ (ether).

Example 12: Synthesis of POE (20 mol) dimer diol;
Charge 600 g of dimer diol “Pripol (Prepol) 2033; made by Unikema”, stir and raise the temperature while flowing nitrogen. When the temperature is raised to 80 ° C., 3.0 g of potassium hydroxide is added. Further, the temperature is raised to 130 ° C. to start addition of ethylene oxide, and the reaction is carried out at a reaction temperature of 160 to 165 ° C. When 328 g of ethylene oxide was added in a reaction time of 2 hours and 20 minutes, it was cooled with water and neutralized with 7.5 ml of 50% aqueous citric acid solution at 110 to 120 ° C. POE (20 mol) dimer diol in which AO = ethylene oxide, n + n ′ = 20, R = H, R ′ = H in the above [Chemical Formula 2] of 1505 g of EO adduct (yield 95%) by precoat filtration using diatomaceous earth Got.

  As a result of analysis of this product, it was a compound having an acid value of 0.11, a hydroxyl value of 79.77, and an HLB value = 10.0.

As a result of measuring the infrared absorption spectrum of this compound, characteristic absorption was observed at wavelengths of 3485 cm ⁻¹ (hydroxyl group) and 1190 cm ⁻¹ (ether).

Example 13: Synthesis of POE (20 mol) dimer diol mono fatty acid ester compound;
Next, fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid per mole of the POE dimer diol obtained in Example 12 Each of “K-PON306; manufactured by Ogura Gosei Kogyo” was charged at a ratio of 1 mole, and an esterification reaction was performed at a reaction temperature of 250 ° C. for 5 to 8 hours while introducing nitrogen. In the nonionic surfactant (2) of the invention, that is, in the above [Chemical Formula 2], AO = ethylene oxide, n + n ′ = 20, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = H POE (20 mol) dimer diol mono fatty acid ester compound was obtained.

  As a result of analysis of these products, isostearic acid ester compound: acid value 4.13, hydroxyl value 38.18, saponification value 36.52, HLB value = 8.3, hydroxystearic acid ester compound: acid value 4.31. , Hydroxyl value 71.53, saponification value 36.21, HLB value = 8.8, polyhydroxystearic acid ester compound: acid value 9.22, hydroxyl value 23.82, saponification value 103.15, HLB value = The compound was 5.3.

As a result of measuring the infrared absorption spectrum of each of the compounds, isostearic acid ester compounds: wavelengths 3489.38 cm ⁻¹ (hydroxyl group), 1737.94 cm ⁻¹ (ester) and 1116.83 cm ⁻¹ (ether), hydroxystearic acid Ester compound: Wavelength 3491.31 cm ⁻¹ (hydroxyl group), 1735.04 cm ⁻¹ (ester) and 1114.90 cm ⁻¹ (ether), polyhydroxystearic acid ester compound: wavelength 3456.59 cm ⁻¹ (hydroxyl group), 1733. 12cm showed characteristic absorption to ^-1 (ester) and 1114.9Cm ^-1 (ether).

Example 14: Synthesis of POE (1-200 mol) dimer diol mono fatty acid ester compound;
By operating in the same manner as in Example 12, the addition reaction time of ethylene oxide (hereinafter also referred to as “EO”) was changed to dimer diol “Pripol (Prepol) 2033; made by Unikema”, the EO addition mole number was changed, In the same manner as in Example 13, fatty acids [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Kokura Gosei Kogyo”, polyhydroxystearic acid “K-PON306; Kokura Gosei Kogyo” Any one of “manufactured”] and a nonionic surfactant (2) [POE addition mole number (EO is 1 to 200 mol)] in the above [Chemical Formula 2], AO = ethylene oxide, n + n ′ = 1 to 200, R = fatty acid acid residue (each fatty acid residue used in the esterification reaction), R ′ = H E was obtained (1 to 200 moles) dimer diol mono-fatty acid ester compound.

  As a result of analysis of these products, for example, a POE (10 mol) dimer diol monoisostearate compound has an acid value of 3.39, a hydroxyl value of 45.17, a saponification value of 48.61, and an HLB value of 5.5. Met.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, the POE (10 mol) dimer diol monoisostearate ester compound showed characteristic absorption at wavelengths of 3475.88 cm ⁻¹ (hydroxyl group), 1737.94 cm ⁻¹ (ester) and 1111.86 cm ⁻¹ (ether).

Example 15: Synthesis of POE (40 mol) dimer diol monoisostearate compound;
1 mol (202.5 g) of isostearic acid “EMERSOL874; manufactured by Cognis Japan” as a fatty acid with respect to 1 mol (1297.5 g) of POE (40 mol) dimer diol obtained by the same operation as in Example 12. The non-ionic surfactant (2) of the present invention (2) 1469.4 g (yield 98.0%) That is, in the above [Chemical Formula 2], POE (40 mol) dimer diol monoisostearate ester in which AO = ethylene oxide, n + n ′ = 40, R = isostearate group, and R ′ = H was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 6.25, a hydroxyl value of 28.08, a saponification value of 26.64, and an HLB value = 11.5.

As a result of carrying out infrared absorption spectrum measurement about this compound, characteristic absorption was recognized by wavelength 3488.61cm < ^-1 > (hydroxyl group), 1736.01cm < ^-1 > (ester), and 11113.94cm < ^-1 > (ether).

Example 16: Synthesis of POE (60 mol) dimer diol monoisostearate compound;
Isostearic acid “EMERSOL874; manufactured by Cognis Japan” as a fatty acid in a ratio of 1 mol (207 g) to 1 mol (1593 g) of POE (60 mol) dimer diol obtained by the same operation as in Example 12. In each case, the esterification reaction was carried out at a reaction temperature of 250 ° C. for 7 hours and 30 minutes while introducing nitrogen, and 1744.3 g (yield 96.9%) of the nonionic surfactant (2) of the present invention, that is, the above-mentioned In [Chemical Formula 2], POE (40 mol) dimer diol monoisostearic acid ester in which AO = ethylene oxide, n + n ′ = 60, R = isostearic acid ester group, and R ′ = H was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 7.46, a hydroxyl value of 23.91, a saponification value of 22.55, and an HLB value = 13.1.

As a result of carrying out infrared absorption spectrum measurement about this compound, characteristic absorption was recognized by wavelength 3497.09 cm < ^-1 > (hydroxyl group), 1735.04 cm < ^-1 > (ester), and 1112.97 cm < ^-1 > (ether).

Example 17: Synthesis of POE (20 mol) dimer diol monohydroxystearate compound;
A ratio of 1 mole (300 g) of hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo” as a fatty acid to 1 mole (1200 g) of the POE (20 mole) dimer diol obtained in Example 12 And 1466.6 g (yield 97.8%) of the nonionic surfactant (2) of the present invention, by carrying out an esterification reaction at a reaction temperature of 250 ° C. for 6 hours and 30 minutes while flowing nitrogen. That is, POE (20 mol) dimer diol monohydroxy stearate in which [O2] in the above [Chemical Formula 2], AO = ethylene oxide, n + n ′ = 20, R = hydroxystearic acid ester group, R ′ = H was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 4.31, a hydroxyl value of 71.53, a saponification value of 36.21, and an HLB value = 9.3.

As a result of carrying out infrared absorption spectrum measurement about this compound, characteristic absorption was recognized by wavelength 3491.31 cm < ^-1 > (hydroxyl group), 1735.04 cm < ^-1 > (ester), and 11114.90 cm < ^-1 > (ether).

Example 18: Synthesis of POE (10 mol) dimer diol monopolyhydroxystearate compound;
For 1 mol (365 g) of POE (10 mol) dimer diol obtained by the same operation as in Example 12, 1 mol (635 g) of polyhydroxystearic acid “K-PON306; manufactured by Ogura Gosei Kogyo” as a fatty acid was used. ), And the esterification reaction was carried out at a reaction temperature of 250 ° C. for 5 hours and 30 minutes while flowing nitrogen, and 982 g of nonionic surfactant (2) of the present invention (yield 98.2%) That is, in the above [Chemical Formula 2], POE (10 mol) dimer diol monopolyhydroxystearic acid ester having AO = ethylene oxide, n + n ′ = 10, R = polyhydroxystearic acid ester group, and R ′ = H was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 10.71, a hydroxyl value of 21.8, a saponification value of 122.55, and an HLB value = 3.7.

As a result of carrying out infrared absorption spectrum measurement about this compound, characteristic absorption was recognized by wavelength 3455.62 cm < ^-1 > (hydroxyl group), 1735.04 cm < ^-1 > (ester), and 11114.90 cm < ^-1 > (ether).

Example 19: Synthesis of POE (20 mol) dimer diol sesqui fatty acid ester compound;
Fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid “to 1 mol of the POE dimer acid ester obtained in Example 12 Each of K-PON306; manufactured by Ogura Gosei Kogyo Co., Ltd.] was charged at a ratio of 1.5 mol, and esterification was performed at a reaction temperature of 250 ° C. for 5 to 8 hours while flowing nitrogen. In the nonionic surfactant (2) of the present invention, that is, in the above [Chemical Formula 2], AO = ethylene oxide, n + n ′ = 20, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = Fatty acid residues (each fatty acid residue used in the esterification reaction): H ratio of 1: 1 POE (20 mol) dimer diol sesquifatty acid ester To give the ether compound.

  As a result of analysis of these products, for example, POE (20 mol) dimer diol sesquiisostearic acid ester compound has an acid value of 6.34, a hydroxyl value of 20.06, a saponification value of 51.55, and an HLB value of 7.5. Met.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, the POE (20 mol) dimer diol sesquiisostearic acid ester compound showed characteristic absorption at wavelengths 3494.20 cm ⁻¹ (hydroxyl group), 1737.94 cm ⁻¹ (ester) and 1116.83 cm ⁻¹ (ether).

Example 20: Synthesis of POE (1-200 mol) dimer diol sesquifatty acid ester compound;
By operating in the same manner as in Example 12, the addition reaction time of ethylene oxide (hereinafter also referred to as “EO”) was changed to dimer diol “Pripol (Prepol) 2033; made by Unikema”, the EO addition mole number was changed, In the same manner as in Example 19, fatty acids [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid “K-PON306; Any one of “manufactured”] and a nonionic surfactant (2) [POE addition mole number (EO is 1 to 200 mol)] in the above [Chemical Formula 2], AO = ethylene oxide, n + n ′ = 1 to 200, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid residue Each fatty acid residue used in the esterification reaction): The ratio of H 1: obtain a POE (1 to 200 moles) dimer diol sesqui fatty ester compound is 1.

  As a result of analysis of these products, for example, POE (60 mol) dimer diol sesquiisostearic acid ester compound is a compound having an acid value of 8.84, a hydroxyl value of 17.8, a saponification value of 27.52, and an HLB value of 12.7. Met.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, the POE (60 mol) dimer diol sesquiisostearic acid ester compound showed characteristic absorption at wavelengths of 3484.59 cm ⁻¹ (hydroxyl group), 1736.01 cm ⁻¹ (ester) and 111.94 cm ⁻¹ (ether).

Example 21: Synthesis of POE (20 mol) dimer diol difatty acid ester compound;
Fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid “to 1 mol of the POE dimer acid ester obtained in Example 12 Each of K-PON306; manufactured by Ogura Gosei Kogyo Co., Ltd.] was charged to a ratio of 2 moles, and the esterification reaction was carried out at a reaction temperature of 250 ° C. for 5 to 8 hours while introducing nitrogen. POE (20 mol) dimer diol difatty acid wherein AO = ethylene oxide, n + n ′ = 20, R = fatty acid residue, R ′ = fatty acid residue An ester compound was obtained.

  As a result of analysis of these products, for example, POE (20 mol) dimer diol diisostearate compound is a compound having an acid value of 4.93, a hydroxyl value of 10.62, a saponification value of 88.02, and an HLB value of 2.0. there were.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, the POE (20 mol) dimer diol diisostearate ester compound showed characteristic absorption at wavelengths of 1739.87 cm ⁻¹ (ester) and 1199.73 cm ⁻¹ (ether).

Example 22: Synthesis of POE (1-200 mol) dimer diol difatty acid ester compound;

  The dimer diol “Pripol (Prepol) 2033; made by Unikema” obtained by the same operation as in Example 12 was controlled by controlling the addition reaction time of ethylene oxide (hereinafter also referred to as “EO”), and the number of moles of EO addition was changed. Further, in the same manner as in Example 21, fatty acids [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid “K-PON306; The esterification reaction is carried out using any one of “manufactured by Kogyo” and the nonionic surfactant (2) [POE addition moles (EO is 1 to 200 mol)] in the above [Chemical Formula 2], AO = ethylene oxide , N + n ′ = 1 to 200, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fat POE (1-200 mol) dimer diol difatty acid ester compound of acid residues (each fatty acid residue used in the esterification reaction) was obtained.

  As a result of analysis of these products, for example, POE (40 mol) dimerdiol diisostearate compound is a compound having an acid value of 10.42, a hydroxyl value of 12.67, a saponification value of 40.65, and an HLB value of 10.0. there were.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, the POE (40 mol) dimer diol diisostearic acid ester compound showed characteristic absorption at wavelengths of 1735.04 cm ⁻¹ (ester) and 111.90 cm ⁻¹ (ether).

Example 23: Synthesis of POE (2 mol) dimer diol diisostearate compound;
Isostearic acid “EMERSOL874; manufactured by Cognis Japan” as a fatty acid in a ratio of 2 mol (768 g) to 1 mol (832 g) of POE (2 mol) dimer diol obtained by the same operation as in Example 12. In each case, the esterification reaction was carried out at a reaction temperature of 250 ° C. for 7 hours and 30 minutes while introducing nitrogen, and the nonionic surfactant (2) of the present invention (2) 1529.6 g (yield 95.6%), that is, the above In [Chemical Formula 2], POE (2 mol) dimer diol diisostearate ester in which AO = ethylene oxide, n + n ′ = 2, R = isostearic acid ester group, and R ′ = isosteric acid ester group was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 5.14, a hydroxyl value of 9.4, a saponification value of 95.56, and an HLB value = 1.1.

As a result of carrying out an infrared absorption spectrum measurement about this compound, characteristic absorption was recognized by wavelength 1739.87cm < ^-1 > (ester) and 1120.69cm < ^-1 > (ether).

Example 24: Synthesis of POE (4 mol) dimer diol diisostearate compound;
Isostearic acid “EMERSOL874; manufactured by Cognis Japan” as a fatty acid in a ratio of 2 mol (801 g) to 1 mol (999 g) of POE (4 mol) dimer diol obtained by the same operation as in Example 12. Then, the esterification reaction was carried out at a reaction temperature of 250 ° C. for 7 hours and 30 minutes while introducing nitrogen, and 1722 g (yield 95.7%) of the nonionic surfactant (2) of the present invention, 2], a POE (4 mole) dimer diol diisostearate ester in which AO = ethylene oxide, n + n ′ = 4, R = isosteric acid ester group, and R ′ = isosteric acid ester group was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 4.93, a hydroxyl value of 10.62, a saponification value of 88.02, and an HLB value = 2.0.

As a result of measuring the infrared absorption spectrum of this compound, characteristic absorption was observed at wavelengths of 1739.87 cm ⁻¹ (ester) and 1119.73 cm ⁻¹ (ether).

Example 25: Synthesis of POE (5 mol) dimer diol diisostearate compound;
Isostearic acid “EMERSOL874; manufactured by Cognis Japan” as a fatty acid in a proportion of 2 mol (645 g) with respect to 1 mol (855 g) of POE (5 mol) dimer diol obtained by the same operation as in Example 12. Then, the esterification reaction was carried out at a reaction temperature of 250 ° C. for 6 hours and 30 minutes while introducing nitrogen, and 1437 g (yield 95.8%) of the nonionic surfactant (2) of the present invention, 2], a POE (5 mol) dimer diol diisostearate ester in which AO = ethylene oxide, n + n ′ = 5, R = isosteric acid ester group, and R ′ = isosteric acid ester group was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 6.56, a hydroxyl value of 10.42, a saponification value of 86.4, and an HLB value = 2.0.

As a result of measuring the infrared absorption spectrum of this compound, characteristic absorption was observed at wavelengths of 1739.87 cm ⁻¹ (ester) and 11118.76 cm ⁻¹ (ether).

Example 26: Synthesis of POP (10 mol) dimer acid;
700 g of dimer acid “Pripol (Puripol) 1009; made by Unikema” is charged and stirred, and the temperature is raised while introducing nitrogen. When the temperature is raised to 80 ° C., 3.5 g of potassium hydroxide is added. Further, the temperature is raised to 130 ° C. to start addition of propylene oxide, and the reaction is carried out at a reaction temperature of 160 to 165 ° C. When 721 g of propylene oxide was added in a reaction time of 2 hours, it was cooled with water and neutralized with 110 ml of a 50% aqueous citric acid solution at 110 to 120 ° C. POP (10 mol) dimer acid with AO = propylene oxide, n + n ′ = 10, R = H, R ′ = H in the above [Chemical Formula 1] of the above-mentioned [Chemical Formula 1] obtained by precoat filtration using diatomaceous earth Got.

  As a result of analysis of this product, it was a compound having an acid value of 0.56, a hydroxyl value of 100.3 (theoretical value 98.0), a saponification value of 99.7, and an HLB value of 3.9.

As a result of carrying out an infrared absorption spectrum measurement about this compound, characteristic absorption was recognized by wavelength 3477.66cm < ^-1 > (hydroxyl group), 1737.86cm < ^-1 > (ester), and 1114.86cm < ^-1 > (ether).

Example 27: Synthesis of POP (10 mol) dimer acid monofatty acid ester compound;
Subsequently, fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearin per 1 mol of the POP dimer acid ester obtained in Example 26 Each of the acids “K-PON306; manufactured by Ogura Gosei Kogyo Co., Ltd.” was charged in a proportion of 1 mol, and the esterification reaction was performed at a reaction temperature of 250 ° C. for 5 to 8 hours while introducing nitrogen. In the nonionic surfactant (1) of the present invention, that is, in the above [Chemical Formula 1], AO = propylene oxide, n + n ′ = 10, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = H ".

  As a result of analysis of these products, for example, POP (10 mol) dimer acid monoisostearate compound has an acid value of 6.9, a hydroxyl value of 51.17, a saponification value of 118.89, and an HLB value of 2.7. Met.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, the POP (10 mol) dimer acid monoisostearate ester compound showed characteristic absorption at wavelengths of 3472.02 cm ⁻¹ (hydroxyl group), 1735.04 cm ⁻¹ (ester) and 1111.05 cm ⁻¹ (ether).

Example 28: Synthesis of POP (1-200 mol) dimer acid monofatty acid ester compound;
By operating in the same manner as in Example 26, the addition reaction time of propylene oxide (hereinafter also referred to as “PO”) was controlled to dimer acid “Pripol (Prepol) 1009; made by Unikema”, and the PO addition mole number was further changed. In the same manner as in Example 27, fatty acids [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Kokura Gosei Kogyo”, polyhydroxystearic acid “K-PON306; The esterification reaction is performed using any one of “manufactured by Kogyo”, and AO = propylene in the above [Chemical Formula 1] of the nonionic surfactant (1) [number of moles of POP added (PO is 1 to 200 moles)] Oxide, n + n ′ = 1 to 200, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = H 2 POP ( 200 mol) to give the dimer acid mono fatty acid ester compound.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 29: Synthesis of POP (10 mol) dimer acid sesquifatty acid ester compound;
Fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid “K” per mole of the POP dimer acid obtained in Example 26 -PON306; manufactured by Ogura Gosei Kogyo Co., Ltd.] was added at a ratio of 1.5 mol, and the esterification reaction was carried out at a reaction temperature of 250 ° C. for 5 to 8 hours while introducing nitrogen. In the nonionic surfactant (1) of the invention, that is, in the above [Chemical Formula 1], AO = propylene oxide, n + n ′ = 10, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = POP (10 mol) dimer acid sesqui fatty acid ester compound in which the ratio of fatty acid residues (each fatty acid residue used in the esterification reaction): H is 1: 1 Obtained.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 30: Synthesis of POP (1-200 mol) dimer acid sesqui fatty acid ester compound;
By operating in the same manner as in Example 26, the addition reaction time of propylene oxide (hereinafter also referred to as “PO”) was controlled to dimer acid “Pripol (Prepol) 1009; made by Unikema”, and the PO addition mole number was further changed. In the same manner as in Example 29, fatty acids [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Kokura Gosei Kogyo”, polyhydroxystearic acid “K-PON306; The esterification reaction is performed using any one of “manufactured by Kogyo”, and AO = propylene in the above [Chemical Formula 1] of the nonionic surfactant (1) [number of moles of POP added (PO is 1 to 200 moles)] Oxide, n + n ′ = 1 to 200, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid residue ( Each fatty acid residue used in the esterification reaction): The ratio of H is 1: 1 is POP (1 to 200 mol) to afford the dimer acid sesqui fatty ester compound.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 31: Synthesis of POP (10 mol) dimer acid difatty acid ester compound;
Fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid “K-” per mole of the POP dimer acid obtained in Example 26 Each of PON 306; manufactured by Ogura Gosei Kogyo Co., Ltd.] was charged to a ratio of 2 moles, and the esterification reaction was carried out at a reaction temperature of 250 ° C. for 5 to 8 hours while introducing nitrogen. In the ionic surfactant (1), that is, in the above [Chemical Formula 1], AO = propylene oxide, n + n ′ = 10, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid residue POP (10 mol) dimer acid difatty acid ester compound (each fatty acid residue used in the esterification reaction) was obtained.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 32: Synthesis of POP (1-200 mol) dimer acid difatty acid ester compound;
By operating in the same manner as in Example 26, the addition reaction time of propylene oxide (hereinafter also referred to as “PO”) was controlled to dimer acid “Pripol (Prepol) 1009; made by Unikema”, and the PO addition mole number was further changed. In the same manner as in Example 31, fatty acids [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Kokura Gosei Kogyo”, polyhydroxystearic acid “K-PON306; The esterification reaction is carried out using any one of “manufactured by Kogyo”, and the nonionic surfactant (1) [number of moles of POP added (PO is 1 to 200 mol)] in the above [Chemical Formula 1], AO = propylene Oxide, n + n ′ = 1 to 200, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid residue ( Was obtained POP (1 to 200 moles) Dimer acid di fatty acid ester compound of the fatty acid residues) using the esterification reaction.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 33: Synthesis of POP (10 mol) dimer diol;
700 g of dimer diol “Pripol (Prepol) 2033; made by Unikema” is charged and stirred, and the temperature is raised while introducing nitrogen. When the temperature is raised to 80 ° C., 3.5 g of potassium hydroxide is added. Further, the temperature is raised to 130 ° C. to start addition of propylene oxide, and the reaction is conducted at a reaction temperature of 160 to 165 ° C. When 721 g of propylene oxide was added in a reaction time of 1 hour and 30 minutes, it was cooled with water and neutralized with 10 ml of 50% aqueous citric acid solution at 110 to 120 ° C. POP (10 mol) dimer diol of AO = propylene oxide, n + n ′ = 10, R = H, R ′ = H in the above [Chemical Formula 2] of 1383 g of EO adduct (yield 95%) by precoat filtration using diatomaceous earth Got.

  As a result of analysis of this product, it was a compound having an acid value of 0.10, a hydroxyl value of 105.50, and an HLB value of 3.4.

As a result of carrying out an infrared absorption spectrum measurement about this compound, characteristic absorption was recognized by wavelength 3450.37 cm < ^-1 > (hydroxyl group) and 1114.86 cm < ^-1 > (ether).

Example 34: Synthesis of POP (10 mol) dimer diol mono fatty acid ester compound;
Subsequently, fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid per mole of the POP dimer diol obtained in Example 33 Each of “K-PON306; manufactured by Ogura Gosei Kogyo” was charged at a ratio of 1 mole, and an esterification reaction was performed at a reaction temperature of 250 ° C. for 5 to 8 hours while introducing nitrogen. In the nonionic surfactant (2) of the invention, that is, in the above [Chemical Formula 2], AO = propylene oxide, n + n ′ = 10, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = A POP (10 mol) dimer diol mono fatty acid ester compound of H was obtained.

  As a result of analysis of these products, for example, a POP (10 mol) dimer diol monoisostearate compound has an acid value of 5.3, a hydroxyl value of 48.42, a saponification value of 41.89, and an HLB value of 2.2. Met.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, the POP (10 mol) dimer diol monoisostearate ester compound showed characteristic absorption at wavelengths of 3474.91 cm ⁻¹ (hydroxyl group), 1736.01 cm ⁻¹ (ester) and 1111.34 cm ⁻¹ (ether).

Example 35: Synthesis of POP (1-200 mol) dimer diol mono fatty acid ester compound;
By operating in the same manner as in Example 33, the addition reaction time of propylene oxide (hereinafter also referred to as “PO”) was controlled on the dimer diol “Pripol (Prepol) 2033; made by Unikema”, and the PO addition mole number was changed. In the same manner as in Example 34, fatty acids [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid “K-PON306; The esterification reaction is performed using any one of “manufactured by Kogyo”, and AO = propylene in the above [Chemical 2] of the nonionic surfactant (2) [POP addition moles (PO is 1 to 200 mol)] Oxide, n + n ′ = 1 to 200, R = fatty acid acid residue (each fatty acid residue used in the esterification reaction), R ′ = H P P was obtained (1 to 200 moles) dimer diol mono-fatty acid ester compound.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 36: Synthesis of POP (10 mol) dimer diol sesqui fatty acid ester compound;
Fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo Co., Ltd., polyhydroxystearic acid“ K- Each of “PON306; manufactured by Ogura Gosei Kogyo Co., Ltd.” was added at a ratio of 1.5 mol, and the esterification reaction was carried out at a reaction temperature of 250 ° C. for 5 to 8 hours while introducing nitrogen. Nonionic surfactant (2), that is, in the above [Chemical Formula 2], AO = propylene oxide, n + n ′ = 10, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid Residue (each fatty acid residue used in the esterification reaction): POP (10 mol) dimerdiol sesquifatty acid ester in which the ratio of H is 1: 1 To give Le compound.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 37: Synthesis of POP (1-200 mol) dimer diol sesquifatty acid ester compound;
By operating in the same manner as in Example 33, the addition reaction time of propylene oxide (hereinafter also referred to as “PO”) was controlled on the dimer diol “Pripol (Prepol) 2033; made by Unikema”, and the PO addition mole number was changed. In the same manner as in Example 36, fatty acids [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid “K-PON306; The esterification reaction is performed using any one of “manufactured by Kogyo”, and AO = propylene in the above [Chemical 2] of the nonionic surfactant (2) [POP addition moles (PO is 1 to 200 mol)] Oxide, n + n ′ = 1 to 200, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid Group (each fatty acid residues used in the esterification reaction): The ratio of H 1: 1 was obtained at a POP (1 to 200 moles) dimer diol sesqui fatty ester compound.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 38: Synthesis of POP (10 mol) dimer diol difatty acid ester compound;
Fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid “K” per mole of the POP dimer diol obtained in Example 33 -PON306; manufactured by Ogura Gosei Kogyo Co., Ltd.] was added at a ratio of 2 moles, and the esterification reaction was performed at a reaction temperature of 250 ° C. for 5 to 8 hours while introducing nitrogen. In the nonionic surfactant (2), that is, in the above [Chemical Formula 2], AO = propylene oxide, n + n ′ = 10, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid residue A POP (10 mol) dimer diol difatty acid ester compound of the group (each fatty acid residue used in the esterification reaction) was obtained.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 39: Synthesis of POP (1-200 mol) dimer diol difatty acid ester compound;
By operating in the same manner as in Example 33, the addition reaction time of propylene oxide (hereinafter also referred to as “PO”) was controlled on the dimer diol “Pripol (Prepol) 2033; made by Unikema”, and the PO addition mole number was changed. In the same manner as in Example 38, fatty acids [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo”, polyhydroxystearic acid “K-PON306; The esterification reaction is performed using any one of “manufactured by Kogyo”, and AO = propylene in the above [Chemical 2] of the nonionic surfactant (1) [number of moles of POP added (PO is 1 to 200 mol)] Oxide, n + n ′ = 1 to 200, R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid Was obtained POP (1 to 200 moles) dimer diol di fatty acid ester compound of group (each fatty acid residues used in the esterification reaction).

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 40 Synthesis of POP (10 mol) + POE (10 mol) dimer acid;
Dimer acid “Pripol (Puripol) 1009; made by Unikema” (400 g) is charged and stirred, and the temperature is raised while introducing nitrogen. When the temperature is raised to 100 ° C., 3.2 g of potassium hydroxide is added. Further, the temperature is raised to 130 ° C. to start addition of propylene oxide, and the reaction is conducted at a reaction temperature of 160 to 165 ° C. and a reaction pressure of 0.06 to 0.1 MPa. After 412 g of propylene oxide has been added in a reaction time of 1 hour, the reaction is then started at the start of addition of ethylene oxide, at a reaction temperature of 160 to 165 ° C., and at a reaction pressure of 0.06 to 0.1 MPa. After 312 g of ethylene oxide has been added in 1 hour of reaction time, the mixture is cooled with water, 32 g of KYOWARD 700SL (manufactured by Kyowa Chemical Industry Co., Ltd.) at 90 to 100 ° C. and 11 ml of ion-exchanged water are dehydrated at 100 to 110 ° C. under reduced pressure. 30 minutes passed at −0.1 MPa, and after filtration, 1068 g of PO + EO adduct (yield 95%) in the above [Chemical Formula 2], AO = propylene oxide + ethylene oxide, n + n ′ = 10 (PO) +10 (EO), POP (10 mol) + POE (10 mol) dimer acid with R = H and R ′ = H was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 1.39, a hydroxyl value of 85.18, a saponification value of 70.17, and an HLB value = 6.6.

As a result of measuring the infrared spectrum of this compound, characteristic absorption was observed at wavelengths of 3473.95 cm ⁻¹ (hydroxyl group), 1736.97 cm ⁻¹ (ester) and 1113.94 cm ⁻¹ (ether).

Example 41: Synthesis of POP (10 mol) + POE (10 mol) dimer acid monofatty acid ester compound;
Subsequently, fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; Ogura] with respect to 1 mol of POP (10 mol) + POE (10 mol) obtained in Example 40 "Made by Kogyo Kogyo", polyhydroxystearic acid "K-PON306; made by Ogura Gosei Kogyo" were charged in a ratio of 1 mole, and nitrogen was introduced, and the reaction temperature was 5O <0> C at 5O <0> C. Esterification reaction is performed for 8 hours, and in the nonionic surfactant (1) of the present invention, that is, in the above [Chemical Formula 1], AO = propylene oxide + ethylene oxide, n + n ′ = 10 (PO) +10 (EO), R = fatty acid Residue (each fatty acid residue used in the esterification reaction), R ′ = H POP (10 mol) + POE (10 mol) dimer To give the acid mono fatty acid ester compound.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 42: Synthesis of POP (1-50 mol) + POE (1-200 mol) dimer acid monofatty acid ester compound;
By operating in the same manner as in Example 40, the addition reaction time of propylene oxide (hereinafter also referred to as “PO”) was controlled on the dimer acid “Pripol 1009; made by Unikema”, and the PO addition mole number was changed. In addition, the addition reaction time of ethylene oxide (hereinafter also referred to as “EO”) was controlled, the number of moles of EO addition was changed, and the fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”], hydroxy was obtained in the same manner as in Example 41. The esterification reaction is performed using stearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo” or polyhydroxystearic acid “K-PON306; manufactured by Ogura Gosei Kogyo”], and a nonionic surfactant ( 1) [Formula of [POP addition mole number (PO is 1 to 50 mol), ethylene oxide addition amount is 1 to 200 mol]] ], AO = propylene oxide + ethylene oxide, n + n ′ = 1 to 50 (PO) +1 to 200 (EO), R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = H 2 POP ( 1-50 mol) + POE (1-200 mol) dimer acid monofatty acid ester compound was obtained.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 43: Synthesis of POP (10 mol) + POE (10 mol) dimer acid sesqui fatty acid ester compound;
Fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; Ogura Gosei Kogyo Co., Ltd.] relative to 1 mol of POP (10 mol) + POE (10 mol) obtained in Example 40 Made of polyhydroxystearic acid “K-PON306; manufactured by Ogura Gosei Kogyo Co., Ltd.” in a ratio of 1.5 mol, and 5 to 5 at a reaction temperature of 250 ° C. while introducing nitrogen. Esterification reaction is performed for 8 hours, and in the nonionic surfactant (1) of the present invention, that is, in the above [Chemical Formula 1], AO = propylene oxide + ethylene oxide, n + n ′ = 10 (PO) +10 (EO), R = fatty acid Residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid residue (each fatty acid residue used in the esterification reaction): H Ratio 1: is) to obtain a POP (10 mol) + POE (10 mol) of dimer acid sesqui fatty ester compound 1.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 44: Synthesis of POP (1-50 mol) + POE (1-200 mol) dimer acid sesqui fatty acid ester compound;
By operating in the same manner as in Example 40, the addition reaction time of propylene oxide (hereinafter also referred to as “PO”) was controlled on the dimer acid “Pripol 1009; made by Unikema”, and the PO addition mole number was changed. In addition, the addition reaction time of ethylene oxide (hereinafter also referred to as “EO”) was controlled, the number of moles of EO addition was changed, and the fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”], hydroxy was obtained in the same manner as in Example 43. The esterification reaction is performed using stearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo” or polyhydroxystearic acid “K-PON306; manufactured by Ogura Gosei Kogyo”], and a nonionic surfactant ( 1) [Formula of [POP addition mole number (PO is 1 to 50 mol), ethylene oxide addition amount is 1 to 200 mol]] ] AO = propylene oxide + ethylene oxide, n + n ′ = 1 to 50 (PO) +1 to 200 (EO), R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid residue ( POP (1 to 50 mol) + POE (1 to 200 mol) dimer acid sesqui fatty acid ester compound in which the ratio of each fatty acid residue used in the esterification reaction): H was 1: 1 was obtained.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 45: Synthesis of POP (10 mol) + POE (10 mol) dimer acid difatty acid ester compound;
Fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; Ogura Gosei Kogyo Co., Ltd.] relative to 1 mol of POP (10 mol) + POE (10 mol) obtained in Example 40 ”, Polyhydroxystearic acid“ K-PON306; manufactured by Ogura Gosei Co., Ltd. ”] in a ratio of 2 moles, and the esterification reaction was carried out at a reaction temperature of 250 ° C. for 5 to 8 hours while introducing nitrogen. In the above [Chemical Formula 1], AO = propylene oxide + ethylene oxide, n + n ′ = 10 (PO) +10 (EO), R = fatty acid residue (used for esterification reaction) POP (10 mol) + POE (each fatty acid residue), R ′ = fatty acid residue (each fatty acid residue used in the esterification reaction) 0 mol) to give the dimer acid di fatty acid ester compound.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 46: Synthesis of POP (1-50 mol) + POE (1-200 mol) dimer acid difatty acid ester compound;
By operating in the same manner as in Example 40, the addition reaction time of propylene oxide (hereinafter also referred to as “PO”) was controlled on the dimer acid “Pripol 1009; made by Unikema”, and the PO addition mole number was changed. In addition, the addition reaction time of ethylene oxide (hereinafter also referred to as “EO”) was controlled, the number of moles of EO addition was changed, and the fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”], hydroxy was obtained in the same manner as in Example 45. The esterification reaction is performed using stearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo” or polyhydroxystearic acid “K-PON306; manufactured by Ogura Gosei Kogyo”], and a nonionic surfactant ( 1) [Formula of [POP addition mole number (PO is 1 to 50 mol), ethylene oxide addition amount is 1 to 200 mol]] ] AO = propylene oxide + ethylene oxide, n + n ′ = 1 to 50 (PO) +1 to 200 (EO), R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid residue ( POP (1-50 mol) + POE (1-200 mol) dimer acid difatty acid ester compound of each fatty acid residue used in the esterification reaction was obtained.

  As a result of analysis of these products, for example, POP (10 mol) + POE (10 mol) dimer acid diisostearate compound has an acid value of 7.06, a hydroxyl value of 13.99, a saponification value of 102.27, and an HLB value of 4. .7 compound.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, POP (10 mol) + POE (10 mol) dimer acid diisostearate ester compound showed characteristic absorption at wavelengths of 1737.94 cm ⁻¹ (ester) and 1113.94 cm ⁻¹ (ether).

Example 47: Synthesis of POP (10 mol) + POE (10 mol) dimer diol;
550 g of dimer diol “Pripol (Prepol) 2033; made by Unikema” is charged and stirred, and the temperature is raised while introducing nitrogen. When the temperature is raised to 100 ° C., 4.4 g of potassium hydroxide is added. Further, the temperature is raised to 130 ° C. to start addition of propylene oxide, and the reaction is conducted at a reaction temperature of 160 to 165 ° C. and a reaction pressure of 0.06 to 0.1 MPa. When 594 g of propylene oxide is added in a reaction time of 2 hours, the reaction is started at the start of ethylene oxide addition, reaction temperature of 160 to 165 ° C., and reaction pressure of 0.06 to 0.1 MPa. When 451 g of ethylene oxide is added in 1 hour of reaction time, the mixture is cooled with water, 44 g of KYOWARD 700SL (manufactured by Kyowa Chemical Industry Co., Ltd.) at 90-100 ° C. and 16 ml of ion-exchanged water are dehydrated under reduced pressure at 100-110 ° C. 30 minutes passed at −0.1 MPa, and after filtration, 1515 g of PO + EO adduct (yield 95%) in the above [Chemical Formula 2], AO = propylene oxide + ethylene oxide, n + n ′ = 10 (PO) +10 (EO), POP (10 mol) + POE (10 mol) dimer diol with R = H and R ′ = H was obtained.

  As a result of analysis of this product, it was a compound having an acid value of 0.11, a hydroxyl value of 77.89, and an HLB value = 6.1.

As a result of measuring the infrared spectrum of this compound, characteristic absorption was observed at wavelengths of 3478.77 cm ⁻¹ (hydroxyl group) and 1111.297 cm ⁻¹ (ether).

Example 48: Synthesis of POP (10 mol) + POE (10 mol) dimer diol mono fatty acid ester compound;
Subsequently, fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; Ogura] with respect to 1 mol of POP (10 mol) + POE (10 mol) obtained in Example 47 "Made by Kogyo Kogyo", polyhydroxystearic acid "K-PON306; made by Ogura Gosei Kogyo" were charged in a ratio of 1 mole, and nitrogen was introduced, and the reaction temperature was 5O <0> C at 5O <0> C. Esterification reaction is performed for 8 hours, and in the nonionic surfactant (2) of the present invention, that is, in the above [Chemical Formula 2], AO = propylene oxide + ethylene oxide, n + n ′ = 10 (PO) +10 (EO), R = fatty acid Residue (each fatty acid residue used in the esterification reaction), R ′ = H 2 POP (10 mol) + POE (10 mol) It was obtained Softimage ol mono-fatty acid ester compound.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 49: Synthesis of POP (1-50 mol) + POE (1-200 mol) dimer diol mono fatty acid ester compound;
By operating in the same manner as in Example 47, the addition reaction time of propylene oxide (hereinafter also referred to as “PO”) was controlled on the dimer diol “Pripol (Prepol) 2033; made by Unikema”, and the PO addition mole number was further changed. In addition, the addition reaction time of ethylene oxide (hereinafter also referred to as “EO”) was controlled, the number of moles of EO addition was changed, and the fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”], hydroxystearin was obtained in the same manner as in Example 47. Non-ionic surfactant (2) by performing esterification reaction using acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo” or polyhydroxystearic acid “K-PON306; manufactured by Ogura Gosei Kogyo” ) [POP addition mole number (PO 1 to 50 mol), ethylene oxide addition amount 1 to 200 mol] In Formula 2], AO = propylene oxide + ethylene oxide, n + n ′ = 1 to 50 (PO) +1 to 200 (EO), R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = H POP (1-50 mol) + POE (1-200 mol) dimer diol mono fatty acid ester compound was obtained.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 50: Synthesis of POP (10 mol) + POE (10 mol) dimer diol sesqui fatty acid ester compound;
Fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; Ogura Gosei Kogyo Co., Ltd.] relative to 1 mol of POP (10 mol) + POE (10 mol) obtained in Example 47 Made of polyhydroxystearic acid “K-PON306; manufactured by Ogura Gosei Kogyo Co., Ltd.” in a ratio of 1.5 mol, and 5 to 5 at a reaction temperature of 250 ° C. while introducing nitrogen. Esterification reaction is performed for 8 hours, and in the nonionic surfactant (2) of the present invention, that is, in the above [Chemical Formula 2], AO = propylene oxide + ethylene oxide, n + n ′ = 10 (PO) +10 (EO), R = fatty acid Residue (each fatty acid residue used for esterification reaction), R ′ = fatty acid residue (each fatty acid residue used for esterification reaction) The ratio of H is 1: 1 is POP (10 mol) + POE was obtained (10 moles) dimer diol sesqui fatty ester compound.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 51: Synthesis of POP (1-50 mol) + POE (1-200 mol) dimer diol sesqui fatty acid ester compound;
By operating in the same manner as in Example 47, the addition reaction time of propylene oxide (hereinafter also referred to as “PO”) was controlled on the dimer diol “Pripol (Prepol) 2033; made by Unikema”, and the PO addition mole number was further changed. In addition, the addition reaction time of ethylene oxide (hereinafter also referred to as “EO”) was controlled, the number of moles of EO addition was changed, and the fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”], hydroxy stearin was obtained in the same manner as in Example 50. Non-ionic surfactant (2) by performing esterification reaction using acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo” or polyhydroxystearic acid “K-PON306; manufactured by Ogura Gosei Kogyo” ) [POP addition mole number (PO 1 to 50 mol), ethylene oxide addition amount 1 to 200 mol] In formula 2], AO = propylene oxide + ethylene oxide, n + n ′ = 1 to 50 (PO) +1 to 200 (EO), R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = fatty acid residue A POP (1 to 50 mol) + POE (1 to 200 mol) dimer diol sesqui fatty acid ester compound in which the ratio of groups (each fatty acid residue used in the esterification reaction): H was 1: 1 was obtained.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

Example 52: Synthesis of POP (10 mol) + POE (10 mol) dimer diol difatty acid ester compound;
Fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”, hydroxystearic acid “12-hydroacid HP; Ogura Gosei Kogyo Co., Ltd.] relative to 1 mol of POP (10 mol) + POE (10 mol) obtained in Example 47 Made of polyhydroxystearic acid “K-PON306; manufactured by Ogura Gosei Kogyo” in a ratio of 2 moles, and flowing nitrogen at a reaction temperature of 250 ° C. for 5 to 8 hours. An esterification reaction was performed, and in the nonionic surfactant (2) of the present invention, that is, in the above [Chemical Formula 2], AO = propylene oxide + ethylene oxide, n + n ′ = 10 (PO) +10 (EO), R = fatty acid residue (Each fatty acid residue used in the esterification reaction), R ′ = fatty acid residue (each fatty acid residue used in the esterification reaction) It was obtained OP (10 moles) + POE (10 mol) dimer diol di fatty acid ester compound.

  As a result of analysis of these products, for example, POP (10 mol) + POE (10 mol) dimer diol diisostearate compound has an acid value of 8.77, a hydroxyl value of 14.39, a saponification value of 54.71, and an HLB value of 4. 0.0 compound.

About the said compound, EO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively. For example, POP (10 mol) + POE (10 mol) dimer diol diisostearate compound absorbs characteristics at wavelengths of 3476.84 cm ⁻¹ (hydroxyl group), 1737.94 cm ⁻¹ (ester) and 111.90 cm ⁻¹ (ether). Admitted.

Example 53: Synthesis of POP (1-50 mol) + POE (1-200 mol) dimer diol difatty acid ester compound;
By operating in the same manner as in Example 47, the addition reaction time of propylene oxide (hereinafter also referred to as “PO”) was controlled on the dimer diol “Pripol (Prepol) 2033; made by Unikema”, and the PO addition mole number was further changed. In addition, the addition reaction time of ethylene oxide (hereinafter also referred to as “EO”) was controlled, the number of moles of EO addition was changed, and the fatty acid [isostearic acid “EMERSOL874; manufactured by Cognis Japan”], hydroxy was obtained in the same manner as in Example 52. The esterification reaction is performed using stearic acid “12-hydroacid HP; manufactured by Ogura Gosei Kogyo” or polyhydroxystearic acid “K-PON306; manufactured by Ogura Gosei Kogyo”], and a nonionic surfactant ( 2) [POP addition mole number (PO is 1 to 200 mol), ethylene oxide addition amount is 1 to 200 mol] In [Chemical Formula 2], AO = propylene oxide + ethylene oxide, n + n ′ = 1 to 200 (PO) +1 to 200 (EO), R = fatty acid residue (each fatty acid residue used in the esterification reaction), R ′ = POP (1-50 mol) + POE (1-200 mol) dimer diol difatty acid ester compound of fatty acid residues (each fatty acid residue used in the esterification reaction) was obtained.

  About the said compound, PO addition mole number and aliphatic ester were confirmed by the infrared absorption spectrum measurement, respectively.

  Hereinafter, the results of evaluating the effect of the nonionic surfactant composition using the polyoxyalkylene dimer acid ester and the polyoxyalkylene dimer diol ether ester of the present invention or one or more of them as an active ingredient will be specifically described according to formulation examples. Show.

Evaluation Example 1: Solubility Test The solubility of the polyoxyalkylene dimer diol and the polyoxyalkylene dimer diol ester compound obtained in the examples in various solvents was evaluated.

  For the solubility test method, the compounds obtained from each Example were adjusted to a 1% solution with the solvent shown in Table 1, mixed with a paddle while heating to 70 ° C, and then cooled to 25 ° C. The condition was observed. In addition, the evaluation standard of the solubility test is indicated by “◯” if it is dissolved transparently, “Δ” if it is dispersed, and “X” if it is not dissolved.

  As a result, as shown in Table 1, Examples 24 and 52 that had undergone esterification were nonionic surfactants that were soluble in nonpolar oil and cyclomethicone and that were excellent in lipophilicity. Further, the POE (1 to 20 mol) addition compound has good odor and liquidity at low temperature, and is excellent as a nonionic surfactant use or as an oil for cosmetics and external preparations.

Evaluation Example 2: Oil Solubility Test by Degree of Esterification The solubility of the POE (20 mol) dimer diol and isostearic acid ester compounds obtained in Examples 12 to 21 in an oil agent by the degree of esterification was evaluated.

  In the oil solubility test method, the compound obtained from each example was adjusted to a 1% solution with the solvent shown in Table 2, mixed with a paddle while heating to 70 ° C, and then cooled to 25 ° C. The condition was observed. In addition, the evaluation standard of the oil solubility test is indicated by ◯ if it is transparently dissolved, Δ if it is dispersed, and × if it is not dissolved.

  As a result, as shown in Table 2, every time the degree of esterification was increased, it was dissolved in nonpolar oil.

Evaluation Example 3: Emulsion stability test;
Examples 54-55 and Comparative Examples 3-5 (milky lotion);
Using the POE (nmol) dimer acid fatty acid ester and the POE (nmol) dimer diol fatty acid ester obtained in Examples, an emulsion having the formulation shown in Table 2 below was prepared. These emulsions were prepared by heating component 1 and component 2 to 70 ° C., gradually adding component 2 to component 1 and emulsifying with a homomixer.

  The emulsion stability of these emulsions was evaluated by the following method. That is, each adjusted emulsion was left in a thermostatic chamber where the atmosphere was repeated at −5 to 40 ° C., and the state of the emulsion was observed one month after this cycle test. The evaluation standard of the emulsion stability was ○ when the cycle test at −5 ° C. and 40 ° C. was stable for one month, and × when separated at one month. (Repeating conditions were [-5 ° C. × 48 hours] → [40 ° C. × 120 hours] as one cycle for one month.)

  As a result, as shown in Table 3, the polyoxyalkylene dimer acid ester compound and the polyoxyalkylene dimer diol ester compound obtained in the examples maintained an emulsified state without separation after one month compared with the comparative compound, It was excellent in stability. (Indicated by mass%)

Example 56: W / O-emollient cream;
W / O-emulsions having the compositions shown in Table 4 below were prepared as follows. That is, component 1 and component 2 were each uniformly dissolved at 70 ° C., and component 2 was mixed while stirring component 1. The W / O emollient cream prepared in this way exhibits a stable, stretchy and moist sensory function as well as a product using a silicon surfactant. Further, the POE (10 mol) Dimerdiol monopolyhydroxystearic acid ester: Instead of (Example 18), for example, a silicon surfactant (“EMALEX SS-5051” manufactured by Nippon Emulsion Co., Ltd.) was used, and the amount added was the same as in Example 56. Compared to the prepared W / O-emollient cream, it showed a sensation of less stickiness.

Example 57: W / O-UV base cake;
A W / O-UV base cake having the composition shown in Table 5 below was prepared as follows. That is, component 1 was heated to 85 ° C., component 2 was heated to 75 ° C., and component 2 was gradually added while stirring component 1. Component 3 was then added and filled before solidifying. This W / O-UV base cake showed excellent sensory properties with good stability, glossiness and elongation equivalent to or better than products using silicon surfactants. Further, instead of polyglyceryl-2 oleate, POE (2 mol) dimer diol diisostearate: (Example 23) and sorbitan sesquiisostearate, for example, a silicon surfactant (“EMALEX SS-5051” Nippon Emulsion Co., Ltd. The amount added was lower than that of the W / O-U / V base cake prepared in the same manner as in Example 57, and showed a sensation of less stickiness.

Example 58: Cream face washing;
The cream face washing shown in Table 6 below was adjusted as follows. That is, component 1 is heated to 75 ° C. and component 2 is heated to 70 ° C., and dissolved uniformly. Next, while stirring component 1, component 2 was gradually added to saponify, and further component 3 was added and cooled to 40 ° C. This cream face-wash has a good feeling of use, an excellent emollient effect, and good foaming stability.

Example 59: Liquid face washing;
A liquid face wash having the composition shown in Table 7 below was prepared as follows. That is, component 1 and component 2 were each heated to 70 ° C., and component 1 was gradually added while stirring component 2. Next, the mixture was stirred while cooling with water, and Component 3 was added at 50 ° C. to cool to 30 ° C. This liquid face wash showed excellent stretch and creamy foaming sensuality.

Example 60: body shampoo;
The body shampoo shown in Table 8 below was adjusted as follows. That is, component 1 is heated to 65 ° C., and components 2 and 3 are each heated to 50 ° C. and dissolved uniformly. Next, components 1 and 3 were gradually added while stirring component 2, and then cooled to 40 ° C., and component 4 was added. This body shampoo showed good sensation of spreading and creamy foaming.

Example 61: cleansing emulsion;
A cleansing emulsion having the composition shown in Table 9 below was prepared as follows. That is, component 1 and component 2 are each heated to 70 ° C. and dissolved uniformly. Next, component 1 was gradually added while stirring component 2. This cleansing emulsion has a characteristic that it is viscous and difficult to sag during use, is excellent in cleansing performance, and exhibits a refreshing sensation after use.

Example 62: cleansing oil;
Cleansing oils having the compositions shown in Table 10 below were prepared as follows. That is, component 1 and component 2 are each heated to 60 ° C. and dissolved uniformly. Next, component 2 was added while component 1 was being stirred. This cleansing oil can be used even with wet hands, and since it has excellent pigment dispersibility, it is well-familiar with foundations, makeup, and the like, and exhibits an excellent sensuality in cleansing performance.

Example 63: cleansing gel;
A cleansing gel having the composition shown in Table 11 below was prepared as follows. That is, component 1 and component 2 are each heated to 70 ° C. and dissolved uniformly. Next, component 2 was added while component 1 was being stirred. This cleansing gel was transparent and very viscous, difficult to sag during use, and was excellent in pigment dispersibility, so it was well suited to foundations, makeup, etc., and exhibited an excellent sensation in cleansing performance.

Example 64: cleansing cream;
A cleansing cream having the composition shown in Table 12 below was prepared as follows. That is, component 1 and component 2 are each heated to 75 ° C. and dissolved uniformly. Next, component 2 was added while component 1 was being stirred. Since this cleansing cream was excellent in pigment dispersibility, it was familiar with foundations, makeup, and the like, and exhibited a sensuality excellent in cleansing performance.

Example 65: Milky white lotion;
A cleansing gel having the composition shown in Table 13 below was prepared as follows. That is, component 1 is heated to 80 ° C. and component 2 is heated to 75 ° C., and dissolved uniformly. Next, component 1 was gradually added while stirring component 2. Then, it cooled to 30 degreeC and added the component 3. This milky white lotion showed excellent sensuality such as good spread and familiarity.

Example 66: W / O-massage cream;
A W / O-massage cream having the composition shown in Table 14 below was prepared as follows. That is, component 1 and component 2 are each heated to 60 ° C. and dissolved uniformly. Next, component 2 was added while component 1 was being stirred. This W / O-massage cream had a very glossy feeling despite the small amount of oil, maintained a certain stretch feeling, and exhibited a sensuality that could be expected to have a massage effect.

Example 67: Moisture cream;
A moisture cream having the composition shown in Table 15 below was prepared as follows. That is, component 1 is heated to 75 ° C. and component 2 is heated to 70 ° C., and dissolved uniformly. Next, component 1 was gradually added while stirring component 2. This moisture cream was glossy, imparted emollient properties, and showed excellent sensuality.

Example 68: hair wax;
A hair wax having the composition shown in Table 16 below was prepared as follows. That is, Component 1 and Component 2 are heated to 80 ° C. and dissolved uniformly. Next, component 2 was gradually added while stirring component 1. Then, it cooled to 50 degreeC and added the component 3. This hair wax had a matte feeling and an excellent sensation for holding styling.

Example 69: Hair gel;
A hair gel having the composition shown in Table 17 below was prepared as follows. That is, Component 1 and Component 2 are heated to 80 ° C. and dissolved uniformly. Next, component 2 was gradually added while stirring component 1. This hair gel maintained a proper styling, gave the hair a wet feeling, and exhibited a sensation excellent in protecting damaged hair and in transparency.

Example 70: Hair shampoo;
A hair shampoo having the composition shown in Table 18 below was prepared as follows. That is, component 1 is heated to 70 ° C. and component 2 is heated to 75 ° C. to dissolve uniformly. Next, component 1 was gradually added while stirring component 2. Component 3 was then added and cooled to 30 ° C. This hair shampoo imparted moist feeling and gloss to the hair and exhibited excellent sensuality as a smooth finger.

Example 71: Conditioning shampoo;
A conditioning shampoo having the composition shown in Table 19 below was prepared as follows. That is, component 1 was heated to 60 ° C. with stirring, then component 2 was added and cooled to 30 ° C. This hair shampoo kept the moisture of the hair, gave gloss and moist feeling, and showed an excellent sensation as a smooth finger.

Example 72: Rinse-in shampoo;
A rinse-in shampoo having the composition shown in Table 20 below was prepared as follows. That is, component 1 is heated to 60 ° C. with stirring and dissolved uniformly. Next, after cooling to 40 ° C., Component 2 was added. This rinse-in shampoo imparted moist feeling and luster to the hair, and showed a sensation excellent in smooth fingering.

Example 73: Hair conditioner;
A hair conditioner having the composition shown in Table 21 below was prepared as follows. That is, component 1 is heated to 75 ° C. and component 2 is heated to 80 ° C. to dissolve uniformly. Next, component 1 was gradually added while stirring component 2. Component 3 was then added and cooled to 30 ° C. This hair shampoo kept the moisture of the hair, gave gloss and moist feeling, and showed excellent sensuality as a smooth finger.

Example 74: Lipstick
Lipsticks having the compositions shown in Table 22 below were prepared as follows. That is, component 1 was heated and dissolved, component 2 was added thereto, kneaded with a roll mill and dispersed uniformly, defoamed, poured into a mold, rapidly cooled, and formed into a stick shape. This lipstick was well-familiar with the skin and showed excellent sensuality in terms of spreadability.

Example 75: Sunscreen lotion A sunscreen lotion having the composition shown in Table 23 below was prepared as follows. That is, component 1, component 2 and component 3 are dissolved at room temperature. Next, component 2 and component 3 were gradually added while stirring component 1. This sunscreen lotion suppressed breakage due to sweat and the like, and was excellent in pigment dispersibility.

Application examples of the present invention include application of cosmetics and external preparations.

Claims (3)

A nonionic surfactant composition obtained by esterifying a hydroxyl group at both ends of polyoxyalkylene dimer acid or polyoxyalkylene dimer diol (alkylene carbon number C2 to C3) with a fatty acid, which is shown below A nonionic surfactant composition comprising at least one selected from the group consisting of a polyoxyalkylene dimer acid ester derivative and a polyoxyalkylene dimer diol ester derivative having a structure.

(In the formula, R and R ′ are hydrogen or fatty acid residues, a, b, c and d are integers of 1 or more and a + b + c + d = 12 to 40. Also, (AO), (AO ′) Is a single alkylene oxide addition polymer of C2 to C3, and (AO), (AO ′) is a block or random addition polymer of alkylene oxides of C2 and C3, n + n ′ is the average addition of alkylene oxide This represents the number of moles and is an integer of 1 to 200. RO and R′O are monoester compounds, sesquiester compounds, and diester compounds depending on the degree of esterification.)

(In the formula, R and R ′ are hydrogen or fatty acid residues, e, f, g and h are integers of 1 or more and are in the range of e + f + g + h = 12 to 40. Also, (AO), (AO ′) Is a single alkylene oxide addition polymer of C2 or C3, and (AO), (AO ′) is a block or random addition polymer of C2 and C3 alkylene oxide, n + n ′ is the average addition of alkylene oxide This represents the number of moles and is an integer of 1 to 200. RO and R′O are monoester compounds, sesquiester compounds, and diester compounds depending on the degree of esterification.)   A nonionic surfactant composition obtained by esterifying a hydroxyl group at both ends of polyoxyalkylene dimer acid or polyoxyalkylene dimer diol (alkylene carbon number C2 to C3) with a fatty acid. And a cosmetic comprising a nonionic surfactant composition comprising at least one selected from the group consisting of a polyoxyalkylene dimer acid ester derivative and a polyoxyalkylene dimer diol ester derivative having the structure shown in Chemical Formula 2.   A nonionic surfactant composition obtained by esterifying a hydroxyl group at both ends of polyoxyalkylene dimer acid or polyoxyalkylene dimer diol (alkylene carbon number C2 to C3) with a fatty acid. And an external preparation containing a nonionic surfactant composition comprising at least one selected from the group consisting of a polyoxyalkylene dimer acid ester derivative and a polyoxyalkylene dimer diol ester derivative having the structure shown in Chemical Formula 2.