JPS6271525A - Emulsion dispersing agent - Google Patents

Abstract

PURPOSE:To remarkably enhance the dispersive power of the titled agent by incorporating 0.2-2mols of at least one kind among the four specified amino ether-type surfactants into 1mol of the specified org. boron compd. to form the emulsion dispersing agent. CONSTITUTION:The emulsion dispersing agent is prepared by incorporating 0.2-2mols of at least one kind among the compds. expressed by formula II (R1 is a 8-22C alkyl, etc., R2 is ethylene, etc., and R3 is H, etc.), formulas III and IV [R4 is a 6-24C alkyl, etc., and R5 shows formula V (X is 1-3 integer and R6 shows R4CON, etc.) and formula VI [R7 is (R2O)n (n is 1-50 integer), R8 shows R3, etc., and R9 expresses R3-N-R3, etc.] into 1mol of the compd. shown by formula I (X, X', Y and Y' are H, methyl, ethyl and an alkenyl group originated in a butene polymer having 5-60 average degree of polymerization).

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a new dispersant. Conventionally known organic boron compound-based emulsifying and dispersing agents include 1. For example, surfactants formed by bonding with boric acid ester residues as disclosed in Japanese Patent Publication No. 11311/1983 previously disclosed by the present applicant. However, this type of organic boron surfactant has a low HLB and is water-insoluble, so it can only be used in W2O type emulsion systems and inorganic dispersion systems in hydrophobic solvents. could not.

In addition, Japanese Patent Publication No. 60-161732 describes a structure containing an oil-soluble/semipolar organic boron surfactant and a carboxylic acid in the same molecule, which has interfacial properties, and the agent is suitable for both hydrophobic and hydrophilic systems. It shows wide compatibility as an emulsifying dispersant, and
Since the semipolar boric acid ester residue in the molecule reduces the ionic repulsion of the carboxylic acid residue, it can create a denser interfacial adsorption film than ordinary anionic surfactants and increase the surfactant ability. However, the present inventors conducted intensive research on improving the emulsification and dispersion performance.

The present invention was based on the discovery that a remarkable improvement in performance can be seen when reacting with a chemical agent. That is, the present invention generally provides that x in formula 1
x' y and Y' are hydrogen atoms, methyl group, ethyl group, RC
O group (where R is a straight chain or alkyl group having 6 to 24 carbon atoms, or an alkenyl group derived from a polymer of butene with an average degree of polymerization of 5 to 60) General formula (2), (3), (4) or (5) (wherein R5 is an alkyl group or alkenyl group having 8 to 22 carbon atoms, R1 is ethylene or propylene, R5 is a hydrogen atom or (R20)
, Hn is an integer from 1 to 50) 5th'e4. t<16 BIJp,z Nzttt
, ttiiiyle=fb-:tx) ゛(Tsurujitol9zku)-7di(ManφF-Lula=Borate, Di(sorbitan)=Borate, Di(Mannitan)=Borate, (Glycerinixylitol)= Examples include borate and (glycerol nisorbitan) borate.

These fatty acids (however, hydrocarbons having 7 to 31 carbon atoms and 1 carbon group) can be reacted with one or more fatty acids having 2 to 9 residual hydroxyl groups or subsequently. It is produced by converting part or all of the resulting terminal hydroxyl group into a tennis box with a fatty acid (provided that it has a hydrocarbon group having 7 to 31 carbon atoms).

On the other hand, examples of succinic acid (hereinafter referred to as a predetermined acid) or anhydride thereof that connect an alkyl group or alkenyl group having 6 to 24 carbon atoms include n-hexylsuccinic acid, isohexylsuccinic acid, n-hexenylsuccinic acid, isohexysenylsuccinic acid, etc. Acid, n-octylsuccinic acid, isooctylsuccinic acid, n-octylsuccinic acid, isooctylsuccinic acid, n-decylsuccinic acid, isodecylsuccinic acid, n-decenylsuccinic acid, isodecenylsuccinic acid, n-dodecylsuccinic acid acid, isododecylsuccinic acid, n-dodecenylsuccinic acid, isododecenylsuccinic acid, n-tetradecylsuccinic acid, isotetradecylsuccinic acid, n-tetradecenylsuccinic acid, isotetradecenylsuccinic acid, n - Hexadecylsuccinic acid, isohexadecylsuccinic acid, n-hexadecenylsuccinic acid, isohexadecenylsuccinic acid, n-octadecylsuccinic acid, isooctadecylsuccinic acid.

n-octadecenylsuccinic acid, isooctadecenylsuccinic acid, n-tocosylsuccinic acid, isotocylsuccinic acid,
n-tocosenylsuccinic acid, isotococenylsuccinic acid, n
-tetracosylsuccinic acid, isotetracosylsuccinic acid,
Examples include n-tetradecylsuccinic acid, isotetradecylsuccinic acid, and acid anhydrides thereof, and further, examples of lower alcohol monoesters of specific acids include methyl ester, ethyl ester, n-propyl ester, etc. , isopropyl ester, n-methyl ester and isobutyl ester.

Next, the method for producing a given organic boron compound will be described in detail.
The reaction between a predetermined di(polyol)=borate and a predetermined acid is carried out under reduced pressure or normal pressure at 50 to 300°C, preferably at 100°C.
This is done by heating and dehydrating at ~200°C, in which case gases that are not involved in the reaction, such as N2 gas and carbon dioxide, are introduced,
The use of azeotropic solvents such as benzene, toluene, xylene etc. makes it easier to complete the reaction. Furthermore, the reaction between a predetermined di(polyol)=borate and a lower alcohol monoester of a predetermined acid is carried out by heat dealcoholization at 30 to 250°C, preferably 70 to 200°C, under reduced pressure or normal pressure. Also, the introduction of gases that are not involved in the reaction, such as N2 gas and carbon dioxide gas, facilitates the completion of the reaction.

In addition, examples of succinic acid or its anhydride linking alkenyl groups derived from a butene polymer having an average degree of polymerization of 5 to 60 include n-hexylsuccinic acid, isohexylsuccinic acid, n-hexenylsuccinic acid, isohexylsuccinic acid, and isohexylsuccinic acid. acid, n-octylsuccinic acid, inoctylsuccinic acid,
n-octynylsuccinic acid, isooctynylsuccinic acid, n
-decylsuccinic acid, indecylsuccinic acid, n-decenylsuccinic acid, isodecenylsuccinic acid, n-dodecylsuccinic acid, indodecylsuccinic acid, n-dodecenylsuccinic acid,
Isododecenyl succinic acid, n-tetradecyl succinic acid,
Isotetradecyl succinic acid, n-tetradecenyl succinic acid, isotetradecenyl succinic acid, n-hexadecyl succinic acid, isohexadecyl succinic acid, n-hexadecenyl succinic acid, isohexade Cenyl succinic acid, n-octadecyl succinic acid, isooctadecyl succinic acid, n-octadecenyl succinic acid, in-octadecenyl succinic acid,
and Examples of the lower alcohol monoester of a given acid include methyl ester, ethyl ester, n-propyl ester,
Examples include isopropyl ester, n-butyl ester, and isobutyl ester.

Next, the method for producing a predetermined organic boron compound will be described in detail.The reaction of a predetermined di(polyol)=borer 1- with a predetermined acid is carried out at 50 to 300°C under reduced pressure or normal pressure, preferably at 10°C.
It is carried out by heating and dehydrating at 0 to 200°C. In this case, the introduction of gases that do not participate in the reaction, such as N2 gas and carbon dioxide gas, and the use of azeotropic solvents, such as methylnaphthalene, benzene, toluene, and xylene, will slow down the reaction. Making closure easier6
Aminoether type surfactants represented by general formulas (2), (3), and (4) include decylamine, dodecylamine, myristylamine, palmitylamine, cetylamine, stearylamine, tallow amine, behenylamine, lauryl aminopropylamine, Beef tallow aminopropylamine, and higher fatty acids such as lauric acid, myristic acid, stearic acid, and oleic acid, and amines such as ethylenediamine, propylene diamine, aminoethylethanolamine, diethylenetriamine, triethylenepentamine, and tetraethylenepentamine. A compound obtained by reacting an imidacillin compound by a phase separation method as a raw material, and adding 1 to 300 known moles of ethylene oxide to 1 mole of these raw materials by a public temperature method, Preferred in terms of performance are dodecylamine, myristylamine, palmitylamine, cetylamine, stearylamine, tallow aminopropylamine, C,, H3s
CoNHC,H,NHC,H4N)i2,C1□H,,
C0NHC, H4NHC2H4NHC2H4N HOC
x t Hx 3.

C, H, NH2 R, C0NHC2H, NH2, R, C0NHC, H4N
HC,H40H,R4C0NHC2H4NHC2H,N
H2, R4C0NHC, H, NHC3HGNH2, R,
C0N) ((C2H, NH), C2H, NHOCR4,
R4C0NH (C2H, NH), C2H, NH2, R4
C0NH (C2H, NH), C, H, NHOCR C2
H4N HC2H4N H.

An aminoether type surfactant in which 5 to 20 moles of ethylene oxide is added to 1 mole is preferred.

The organic boron compound and aminoether surfactant thus obtained are used in a molar ratio of 1:0.2 to 2, but preferably the acid value equivalent of the given organic boron compound is The preferred molar ratio is 1:0.5 to 2 mol when mixed to neutralize the amine value equivalent of the aminoether type surfactant.

The emulsifying and dispersing agent of the present invention thus obtained has the following characteristics: In addition to being a useful agent in preparing ○/W type polymer emulsions and stabilizing W/○ type cold cream, It is also used as an auxiliary agent for nonflammable hydraulic fluids with a small amount of water added. In addition, when used as an inorganic dispersant, magnetic iron oxide metal particles, ceramic dispersant for water and oil paints, emulsifying dispersion of water-based paints, magnetic fluid auxiliary agent, and metal paste dispersant for electromagnetic shielding paints, it improves the conductivity of the system. enhance

Next, examples of the present invention will be shown.

Example 1. Molar ratio of a compound having the following structural formula: 1:1 C4 (200C Near H33) In a four-loop flask equipped with a stirrer, a thermometer, a gas inlet tube, and a reflux condenser, 104 g of styrene, methyl acrylate, 0.13 g of ammonium persulfate, and 696 g of water were added. 15.5 g of the compound having the above structural formula was charged and emulsion polymerization was carried out at 75°C for 5 hours to obtain an emulsion with an average particle size of 1#.

Moreover, even when left at 40° C. for 6 months, no separated phase was formed and the product remained stable.

On the other hand, an emulsion obtained by emulsion polymerization using the same amount of sodium stearate in place of the above compound of the present invention produced a separated phase after being allowed to stand at 40°C for 20 days.

Example 2 Into the same apparatus as in Example 1, 93.7 g of styrene, 354.6 g of methyl methacrylate, 0.13 g of potassium persulfate, 1083 g of water, and 15.7 g of a compound having the following structural formula were charged at a molar ratio of 1:l CH200C. Emulsion polymerization was carried out at □7H3° and 50°C for 8 hours to obtain an emulsion with a first class average particle size. Even when this emulsion was allowed to stand at 30° C. for 1 year and 1 month, it remained stable without forming a separated phase.

Example 3 448 g of methyl methacrylate was placed in the same apparatus as in Example 1.
0.2 g of potassium persulfate, 1083 g of water, and 15.7 g of a compound having the following structural formula were charged in a molar ratio of 1:1.2. Emulsion polymerization was carried out at 50°C for 5 hours, resulting in an average particle size of 11.
An emulsion was obtained. This emulsion was heated to 50℃ for 7
Even after standing for several months, no separated phase was formed.

It was stable.

Example 4 In a 200 cc beaker, 3 g of beeswax, 125'F paraffin Log, 13 g of petrolatum, and 40 g of liquid paraffin were added.
A compound consisting of the following structural formula (equimolar mixture) 5
molar ratio of 1:1.5, heated and melted at 75 to 85°C, and mixed uniformly.

28 g of warm water at 80°C was gradually added with stirring, and then cooled. The average particle size of the emulsion obtained was 1.5 #, and the long-term stability test (20°C, 65
It was stable for 1 year and 2 months under conditions of constant pH and constant temperature and humidity. On the other hand, the emulsion obtained by using the same amount of sorbitan sesquioleate instead of the organic boron compound of the present invention has an average particle size of about 4M, and the liquid paraffin is separated within 2 months after production. It was observed.

Example 5 A compound having the following structural formula was used in a molar ratio of 1:1.1 C□, H25 (However, R is an isohexadecenyl group and an isooctadecenyl group in a ratio of 4:1.) The following A magnetic paint with the following composition was created.

Vinyl chloride resin 50g Polyurethane resin 40g Carbon black
5g methyl isobutyl ketone 100
0 g xylene 1000 g Compound of the present invention 1 g A magnetic paint as a comparative test example was prepared by using the same amount of a comparative substance (child structure) in place of the organic boron compound of the present invention.

Then two types of paint were applied to the polyester film,
As a result of making magnetic tapes, running them on a playback device, and examining the abrasion properties of the tapes, the tapes based on the examples containing the organic boron compound of the present invention had less wear than the tapes using the comparative materials, and the γ- Fe20. The dispersion was also good.

Example 6 Weighed 5g of chromium oxide with an average particle size of 0.8M in a μ graduated cylinder, then added 0°3g of a compound with the following structural formula in a molar ratio of 1:1 (where R is the residue of polybutene with an average degree of polymerization of 15). 10m
1:1 (weight ratio) of toluene and methyl ethyl ketone in Q
After the solution dissolved in the mixed solvent was placed on a shipwreck, it was shaken up and down 30 times, and the amount of chromium oxide precipitated was 301 portions after shaking, and the amount of chromium oxide precipitated was 0.2 when left to stand still.
It was below mα and exhibited stable dispersion.

On the other hand, when the same amount of sorbitan monoisoleate was used instead of the compound of the present invention, 1.8 m12 of sediment was formed after standing for 30 minutes, and the same amount of ammonium isoolenic acid soap was used. In this case, 1.7 mu of precipitate was generated after standing for 30 minutes.

Example 7 Resin when a compound having the following structural formula in a molar ratio of 1:1.2 (where R is a residue of polybutene with an average degree of polymerization of 30) and sorbitan monostearard were used as a dispersant for an MMA resin colorant. Coloring agent inside (titanium white)
The particle size distribution was compared.

Molding method: Mixing for 10 minutes, injection molding at 180°C, 5 parts blending ratio (Formulation 1) (Formulation 2)
MMA resin 100 parts 100 parts Titanium white 1 part 1 part The above compound of the present invention 0.2 parts - Sorbitan monostearard - 0.2 parts Particle size distribution comparison data sample Average particle size (μ) Titanium white (before resin compounding) 200 pieces Compound of the Invention 6 Sorbitan Monostearate Compound 50 Based on the results, it was found that the organic boron compound of the present invention is superior to sorbitan monostearate in colorant dispersion performance.

- A comparison test was conducted on the dispersibility of magnesium hydroxide particles in hydrocarbons.

Blend ratio Blend 1 Blend 2 Magnesium hydroxide 30 parts 30 parts Kerosene
65 parts 65 parts Compound of the above invention
5 parts - Sorbitan dibehenate - 5 parts The above two dispersions were placed in a graduated cylinder with a height of 25 CIl+, and under constant temperature and humidity conditions of 20° C. and 65% RH.
When we observed the dispersion stability of magnesium hydroxide in kerosene, we found that the dispersion stability of magnesium hydroxide mixed with sorbitan dibehenate (
Formulation 2) had a sedimentation rate of 0.81 in 24 hours and 1.71 in 48 hours, whereas the formulation containing the compound of the present invention (
Formulation 1) is 0.31 in 24 hours and 0.7 CI in 48 hours.
The precipitation was 11.

Example 9 (R is an isooctadecenyl group) 30 mQ of a 0.5% aqueous solution of the compound having the above structure and 30 mQ of liquid paraffin were placed in a homogenizer, and 6
The mixture was mixed at 000 rpm for 3 minutes, placed in a 50 mQ measuring cylinder, allowed to stand at 20°C, and the separation of water or oil was examined. In addition, as a comparative substance B, a salt of lauric acid and a salt of dodesysuccinic acid were selected, each of which was made into a 0.5% aqueous solution, and then subjected to the same test. As a result, the test example using the salt of lauric acid separated the aqueous phase of 10 mQ after 3 hours, and the test example using the salt of dodecylsuccinic acid separated the aqueous phase of 20 mQ and the oil phase of 14 mQ. On the other hand, in the test example using the compound of the present invention, 4 mQ of aqueous phase was separated after standing for 6 hours, but the emulsification performance was significantly better than that of the comparative substance.

Patent Applicant Toho Chemical Industry Co., Ltd. Patent Application No. 210034 of 1985, Relationship with the amended case Patent Applicant Nihonbashi Kajugaracho Address 1-14-9 Tou, Nihonbashi Kakigara-cho, Chuo-ku, Tokyo
Name Toho Chemical Industry Co., Ltd. 4, Number of inventions increased by amendment None 5, Subject of amendment Correction of clerical errors in Zenbumi MJ 6, Contents of amendment 1, Full text correction of detailed description of invention Thread 1) 1. Name of the invention Emulsifying and dispersing agent 2. Claims ■ General formula 1゜CHJLO-A RCO-5 (where R is an alkyl group having 7 to +3 carbon atoms or an alkenyl group n is o, l, 2 or 3 ) (However, R' is an alkyl group having 6 to 24 carbon atoms, %=lkr alkenyl group, or an alkenyl group derived from a butene polymer with an average degree of polymerization of 5 to 60, and at least one R or R/ General formulas (2), (3), (4) and (5) per mole of each type (where R3 is an alkyl group or alkenyl group having 8 to 22 carbon atoms, R2 is (Ethylene or propylene, R1 is a hydrogen atom or (R,0)nHn is an integer from 1 to 50) However, R4 is an alkyl group or alkenyl group having 6 to 24 carbon atoms, and R1 is a formula. An emulsifying and dispersing agent containing 0.2 to 4 moles.

3. Detailed description of the invention The present invention relates to a new emulsifying and dispersing agent.

The present applicant has conventionally found that these boron-containing surfactants have a boric acid ester group of a polyhydric alcohol having adjacent hydroxyl groups and also have a hydrophobic group, and although these boron-containing surfactants exhibit some degree of performance as emulsifying and dispersing agents, they are not necessarily satisfactory. The present inventors conducted various studies to improve the emulsification and dispersion performance of the previously disclosed boron-containing surfactants, and found that these boron-containing surfactants and alkylene The present invention was based on the discovery that emulsification and dispersion ability is significantly improved when used in combination with an oxide-added aminoether type surfactant.

That is, the present invention is based on the general formula (1) [where x, x' y and Y' are hydrogen atoms, methyl groups,
group or alkenyl group, n is 0, ■, 2 or 3)0O
H (wherein R' is an alkyl group having 6 to 24 carbon atoms, an alkenyl group, or an alkenyl group derived from a butene polymer having an average degree of polymerization of 5 to 60, and contains at least one R or R in one molecule) (However, R1 is an alkyl group having 8 to 22 carbon atoms, Al (However, R4 is an alkyl group having 7 to 21 carbon atoms.) group alkeni 0 or 1
An integer of ~3, R1 is R4C0N or (R,0)nH] R3 [However, R1 is R1, R, (N - R,)y (y =
The present invention provides an emulsifying and dispersing agent containing 0.2 to 4 mol of one type of O or R1.

The method for producing the boron-containing surfactant represented by the general formula (1) of the present invention is already clear in Japanese Patent Publication No. 11311/1982 and Japanese Patent Application Laid-Open No. 161732/1983, 8 to 24 fatty acids, fatty acid anhydrides, fatty acid esters, alkyl (or alkenyl) succinic anhydrides having an alkyl group or alkenyl group having 6 to 24 carbon atoms, and polymers of butenes having 5 to 60 carbon atoms and maleic acid. By reacting with polybutenyl succinic anhydride by a known method, di(xylitol) borate, di(sorbitol) borate, di(mannitane) borate, (glyceride, phosphorus, xylitol) ) = borate, (glycerin, sorbitan)
Borate and the like can be mentioned, but it is preferable to use di(glycerin) borate and di(sorbitol) borate from the economic point of view. Fatty acids having 8 to 24 carbon atoms, fatty acid anhydrides, and fatty acid esters include capric acid, lauric acid, myristic acid,
Examples include valmitic acid, stearic acid, oleic acid, linoleic acid, erucic acid 1, isostearic acid, etc., but from the economical and performance standpoints, it is preferable to use lauric acid, stearic acid, and oleic acid. Carbon number 6~
Alkyl (or alkenyl) succinic acid hydrides having 24 alkyl or alkenyl groups include n- or isohexylsuccinic acid, n- or isohexylsuccinic acid 1, n- or isooctylsuccinic acid, n- or isohexylsuccinic acid, n- or isohexylsuccinic acid, n- or isohexylsuccinic acid, Octynylsuccinic acid, n- or indodecenylsuccinic acid, n- or isotetradecylsuccinic acid, n
- or isotetradecenylsuccinic acid, n- or isohexadecylsuccinic acid, - 與dTOP! -11n- or isooctadecylsuccinic acid, rho or isooctadecenylsuccinic acid, n- or tocosylsuccinic acid, n- or isotocosenylsuccinic acid, n- or isotetradecylsuccinic acid, n- or isotetradecylsuccinic acid Anhydrides such as acids can be used, but in some cases, acids themselves and their esters can also be used. Among these, n- or isoalkenyl succinic acid having 14 to 18 carbon atoms is preferred from the viewpoint of economy and effectiveness.

The aminoether type surfactants represented by general formulas (2), (3), and (4) of the present invention include decylamine, dodecylamine,
myristylamine, valmitylamine, cetylamine,
Stearylamine, tallow amine, behenylamine, lauryl aminopropylamine, tallow aminopropylamine, higher fatty acids such as lauric acid, myristic acid, stearic acid, oleic acid, ethylene diamine, propylene diamine, aminoethylethanolamine, diethylene triamine, Using an amide compound imidacilline compound obtained by reacting with amines such as triethylene pentamine and tetraethylene pentamine by a known method as a raw material, 1 to 1 mol of ethylene oxide or/and propylene oxide is added to 1 mole of these raw materials.
It is obtained by adding 300 mol of dodecylamine by a known method, and is preferably dodecylamine in terms of performance.
myristylamine, valmitylamine, cetylamine,
Stearylamine, beef tallow aminopropylamine, C,
H,,C0NI-IC,H4NHC,H,NHl.

C,,)! ,3CONHC,H4NHC,H4NHC,
H4NHOCC,,H,,,N-CH,,C,84NH.

An aminoether type surfactant in which 5 to 20 moles of ethylene oxide is added to 1 mole is preferred.

The organic boron compound and aminoether surfactant thus obtained are used in a molar ratio of 1:0.2 to 4. In order to neutralize the amine value equivalent of the aminoether type surfactant, the preferred molar ratio is λ1:0.5 to 411 moles.

The emulsifying fraction agent of the present invention thus obtained is characterized by being a useful agent when making ○/W type polymer emulsions, and being a agent for stabilizing W2O type cold cream. When used in small quantities as a magnetic fluid aid and a metal paste dispersant for electromagnetic shielding paints, it increases the conductivity of the system.

Next, examples of the present invention will be shown.

Example 1 The following test was conducted using a mixture of a boron-containing surfactant and an aminoether type surfactant at a ratio of L: 1 mol.

104 g of styrene, methyl acrylate, 0.13 g of ammonium persulfate, 696 g of water, and 15.5 g of a compound having the above structural formula were placed in a four-bottle flask equipped with a stirrer, a thermometer, a gas inflow tube, and a reflux condenser, and the mixture was heated at 75°C for 5 hours. As a result of emulsion polymerization, an emulsion with an average particle size of 1 μm was obtained, and the emulsion remained stable without forming any separated phase even after being left standing at 40° C. for 6 months.

On the other hand, an emulsion obtained by emulsion polymerization using the same amount of sodium stearate in place of the above-mentioned compound of the present invention produced a separated phase after being allowed to stand at 40°C for 20 days.

Example 2 Into the same apparatus as in Example 1, 93.7 g of styrene, 354.6 g of methyl methacrylate, 0.13 g of potassium persulfate, 1083 g of water, and 15.7 g of the following mixture were charged at 50°C. Emulsion polymerization was carried out for 8 hours to obtain an emulsion with an average particle size of lμ. Even when this emulsion was allowed to stand at 30° C. for 1 year and 1 month, it remained stable without forming a separated phase.

Example 3゜448 g of methyl methacrylate was placed in the same apparatus as in Example 1.
, 15.7 g of the following mixture with 0.2 g of potassium persulfate and 1083 g of water was prepared. :1.2 molar ratio mixture was subjected to emulsion polymerization at 50°C for 5 hours, resulting in an average particle size of 1μ.
An emulsion was obtained. This emulsion was heated to 50℃ for 7
Even after standing for several months, no separated phase was formed and the product remained stable.

Example 4 In a 200cc beaker, 3g of beeswax, 125°F paraffin log, 13g of vaseline, and 40g of liquid paraffin were charged with 5g of a 1:1 molar mixture of two of the following structural formulas, respectively. L: 1.5 Molar ratio mixture (where A=C11, (CI+,), (Jl-C11,
-) 1.5 molar mixture of C0OH and 1.5 molar mixture Heating and melting at 75 to 85°C, mixing uniformly, and then heating to 80°C
28g of warm water was gradually added with stirring, and then cooled, the average particle size of the emulsion obtained was 1.5μ,
and long-term stability test (20℃, 65RH constant temperature, constant temperature)
The average particle size of the 1 year and 2 month sample was approximately 4μ, and separation of liquid paraffin was observed 2 months after production.

Example 5: Using a mixture having the following structural formula, a mixture with a molar ratio of 1:1 (where R is 4:1 of isohexadecenyl group and isooctadecenyl group) is as follows. We created a magnetic paint with the following composition.

δ-Fe, 0. 350g vinyl chloride resin 50g polyurethane resin
40g carbon black
5g Methyl isobutyl ketone 1000g

Then two types of paint were applied to the polyester film,
Magnetic tapes were made and run on a playback device, and the abrasion properties of the tapes were examined. As a result, the tapes based on the examples containing the mixtures of the present invention showed less wear than the tapes using the comparative materials, and γ-Fe.

0, the dispersion was also good.

Example 6 Weighed 5g of chromium oxide with an average particle size of 0.8μ in a graduated cylinder, then added 0.3g of a mixture of the following structural formula to a 1:1 molar mixture of 10mfl of toluene and methyl ethyl ketone (1=1).
Weight ratio) After lubricating the solution dissolved in the mixed solvent, 3
When the sample was shaken 0 times, the amount of chromium oxide precipitated was 0.2 rrl or less after being allowed to stand for 30 minutes after shaking, indicating stable dispersion.

On the other hand, when the same amount of sol-obitan monoisoleate was used instead of the compound of the present invention, 3
1.8 mQ of precipitate was formed after standing for 0 minutes, and 3
1. After 0 minutes of standing. A precipitate of 7 mQ was formed.

Example 7 A 1:1.2 molar ratio mixture of a mixture of compounds having the following structural formula (where R is a residue of polybutene with an average degree of polymerization of 30) and sorbitan monostearard were used as a dispersant for an MMA resin colorant. The particle size distribution of the colorant (titanium white) in the resin was compared.

Molding method: Mixing for 10 minutes, injection molding at 180°C, 5 parts blending ratio (Formulation 1) (Formulation 2) MM
A resin 100 parts 100 parts Titanium white
1 part 1 part The above mixture of the present invention
0.2 parts - sorbitan monostearade - 0,
Two-part particle size distribution ratio calibration data sample Average particle size (μ) Titanium white (before resin compounding) 200 Mixture of the present invention 6 Sorbitan monostearate compound 50 Based on the results above, the organic boron compound of the present invention is sorbitan monostearate. It was found that the colorant dispersion performance was superior to that of the conventional method.

Example 8 A comparative test on the dispersibility of magnesium hydroxide particles in hydrocarbons was conducted using a 1:2 molar ratio mixture of a mixture of compounds having the following structural formula and sorbitane dibehenate.

Blend ratio Blend 1 Blend 2 Magnesium hydroxide 30 parts 30 parts Kerosene
65 parts 65 parts Mixture of the above invention
5 parts - Sorbitan dibehenate - 5 parts The above two dispersions were placed in a graduated cylinder with a height of 25 cm, and the dispersion stability of magnesium hydroxide in kerosene was measured under constant temperature and humidity conditions of 20°C and 65% RH. When observed, it was found that the mixture containing sorbitan dibehenate (Formulation 2) sedimented by 0.8 degrees in 24 hours and 1.70 degrees in 48 hours, whereas the mixture of Chinoku Formulation 1 containing the mixture of the present invention sedimented. ) was 0.3 mark in 24 hours and 0.7 m in 48 hours.

Example 9 (x + y + z = 12) (1:), 8 molar ratio mixture (where R is isooctadecenyl group) 30 mm of a 0.5% aqueous solution of the above mixture and 30 mm of liquid paraffin were placed in a homogenizer, 6000rp
The mixture was mixed for 3 minutes at 100 m, then placed in a 50 mm measuring cylinder, allowed to stand at 20° C., and the separation of water or oil was examined. In addition, as comparison substances, we selected salts for lauric acid and salts for dodecylsuccinic acid.

After making each into a 0.5% aqueous solution, it was subjected to the same test. As a result, the test example using the salt of lauric acid separated a 10 mm aqueous phase after 3 hours, and the test example using the salt of dodecylsuccinic acid separated a 20 mm aqueous phase and a 14 mm oil phase. On the other hand, in the test example using the compound of the present invention, a 4 mm aqueous phase was separated after standing for 6 hours, but the emulsification performance was significantly better than that of the comparative substance.

Patent applicant: Toho Chemical Industry Co., Ltd.

Claims (1)

[Claims] 1. General formula 1, ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(1) However, in formula 1, X, X'Y and Y' are hydrogen atoms, methyl groups,
Ethyl group, RCO group (where R is a straight chain or branched alkyl group or alkenyl group having 6 to 24 carbon atoms) ▲ Formula,
There are chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and at least one compound represented by an alkenyl group derived from a butene polymer with an average degree of polymerization of 5 to 60, 1 type per mole. General formulas (2), (3), (4) and (5) for 1 mole ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼... (2) (However, R_1 is an alkyl group or alkenyl group with 8 to 22 carbon atoms , R_2 is ethylene or propylene, R_3 is a hydrogen atom or (R_2O)_nH n is an integer from 1 to 50) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(3) ▲Mathematical formulas, chemical formulas, tables, etc. Yes▼...(4) However, R_4 is an alkyl group or alkenyl group having 6 to 24 carbon atoms, and R_5 is a formula▲There are mathematical formulas, chemical formulas, tables, etc.▼[However, X is 0 or an integer from 1 to 3, R_5= R_4CON or (R_2O)
_nH] There are ▲ mathematical formulas, chemical formulas, tables, etc. ▼...(5) (However, R_7 is (R_2O)_nH, or the formula ▲
There are chemical formulas, tables, etc. ▼ [However, R_8 is R_3, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ {y = 0 or an integer from 1 to 2, R_9 is ▲ There are ▲ Numerical formulas, chemical formulas, tables, etc. ▼ or ▲ Numerical formulas, There are chemical formulas, tables, etc. ▼} An emulsion powder containing at least 0.2 to 2 moles of one of the compounds shown in .