JP2848706B2 - Alkylidene glycerol surfactant and detergent composition containing the same - Google Patents

Description

Description: TECHNICAL FIELD The present invention provides novel alkylidene glycerol surfactants useful in detergent compositions.

BACKGROUND AND PRIOR ART The condensation products of aldehydes and glycerol (alkylidene monoglycerol or monoglycerol acetal) are disclosed in GB 414772 (Johnson). For example, reacting lauric aldehyde with glycerol gives a monoglycerol acetal,
Membered dioxolane ring structure: Is described. Although such products are hydrophobic, the introduction of water-solubilizing groups results in materials useful as wetting, cleaning, foaming and dispersing agents.
For example, the compounds shown above do not themselves exhibit foaming properties, but when reacted with chloro-sulfonic acid, provide highly foaming anionic surfactants, and upon ethoxylation, nonionic surfactants. Agent is obtained.

EP 12543A (ICI) discloses cyclic acetals and ketals of glycerol and other polyols and their use as emollients in cosmetic, toilet and household cleaning compositions. A reaction product of the aldehyde RCHO and glycerol is disclosed, which comprises a mixture of a five-membered ring structure A (1,3-dioxolane) and a six-membered ring structure B (1,3-dioxane), the proportion of which is It can be changed by a known method by changing the conditions.

These materials can be alkoxylated, acylated or alkylated as desired.

Monoglycerol ketal is US3909460 and US39489
53 (McCoy / Texaco Inc). These substances can be synthesized by the condensation of ketones with glycerol and have the following formula: Wherein R and R ′ are alkyl groups containing a total of 6 to 30 carbon atoms. ]. Unlike monoglycerol acetal, these substances can only be present in the form of a five-membered ring. These substances, like the monoglycerol acetal, require the introduction of a water-solubilizing group, such as sulfate or polyoxyethylene, to obtain a water-soluble surfactant.

Thus, the present inventors have synthesized acetal and ketal containing two or more glycerol residues. These materials are liquids or soft solids and behave as effective water-soluble nonionic surfactants, which are particularly useful in detergent compositions for laundering textiles. It has been found that when combined with other known surfactants, oil stain cleaning power is synergistically improved.

In many respects, the novel substances behave in a manner similar to ethoxylated alcohol nonionic surfactants and, if environmentally it is desirable to reduce the use of ethoxylated substances, they can be used in detergent compositions. It is possible to replace all or part of the included ethoxylated alcohol nonionic surfactant with a new substance.

Definitions of the Invention Accordingly, the present invention provides a compound of formula I: [Wherein, R ₁ represents a linear or branched alkyl or alkenyl group, R ₂ represents a hydrogen atom or a linear or branched alkyl or alkenyl group, and the total number of carbon atoms in R ₁ and R ₂ is 7 to 17, and A represents a monoglycerol or diglycerol group. ] Is provided.

A second aspect of the invention is the use of a compound as defined above as a surfactant or wetting agent.

A third aspect of the present invention is a detergent composition having a surfactant system comprising a compound as defined above.

A fourth aspect of the present invention is a process for preparing a compound of formula I, comprising reacting an aldehyde or ketone of the formula: R ₁ —CO—R ₂ with an oligomer of glycerol.

DETAILED DESCRIPTION OF THE INVENTION Alkylideneglycerol The compound of formula I above has more than one compound in the molecule (especially 2
It is considered to be a novel substance in the presence of (one or three) glycerol groups. Each of these two compounds
They are called alkylidene diglycerol and alkylidene triglycerol.

Diglycerol (A is a monoglycerol group.)
Has the formula IIa and IIb: (The linear isomer IIa is the major isomer).

Triglycerol (A is a diglycerol group.)
Exists as a mixture of the six structural isomers represented by the following formulas IIIa to IIIf. Again, the chain isomer IIIa is the main isomer.

The main chain isomers of alkylidene di- and triglycerols IIa and IIIa have the general formula Ia: [Wherein, n is 1 or 2. ].

The total number of carbon atoms in the groups R ₁ and R ₂ of the compound of the present invention is 7 to 17, preferably 9 to 13. In principle, the carbon atoms can be distributed in any proportion between the two groups. However, the compounds studied by the present inventors are classified into two types, that is, compounds in which R ₂ is a hydrogen atom and compounds in which R ₂ is a methyl group. In both cases, R ₁ is a straight or branched chain alkyl or alkenyl group.

As used herein, R ₂ derived from the aldehyde R ₁ CHO
Is a 1-alkylidene (di- or tri-) glycerol or (di- or tri-) glycerol acetal, and the methyl ketone R ₁ CO
A compound derived from CH _{3 wherein} R ₂ is a methyl group is 2-
Alkylidene (di- or tri-) glycerol or (di- or tri-) glycerol ketal.

As inferred from the examination of the above-mentioned known documents, the compound in which R ₂ is a hydrogen atom (1-alkylidene di- and triglycerol, or di- or triglycerol acetal) is also a 6-membered ring isomer Ib: Exists in the form of

In fact, usually a mixture of the two forms is obtained, predominantly in the form of a five-membered ring.

The present inventors have studied in detail the following compounds.
All alkyl groups are straight.

1-de Siri Denji glycerol _{(R 1 = C 9, R} 2 = H) 2- de Siri Denji glycerol _{(R 1 = C 8, R} 2 = methyl) 1-dodecane Siri Denji glycerol (R ₁ = C _11, R ₂ = H) 2-dodecylidene diglycerol (R ₁ = C ₁₀ , R ₂ = methyl) 1-decylidene triglycerol (R ₁ = C ₉ , R ₂ = H) 1-dodecylidene triglycerol ( R ₁ = C ₁₁ , R ₂ =
H) These materials are estimated to have a hydrophilic-lipophilic balance (HLB) ranging from about 7 to 13 and are useful in a wide range of detergent compositions. For a complete discussion of HLB, see “Surfactants in Consumer Products”, edited by J Falbe,
See Springer-Verlag, 1987.

Alkylidene glycerol is liquid to solid, depending on the length and type of the alkyl or alkenyl chain, the number of glycerol groups in the molecule, and the particular isomer or isomer mixture present.

Linear 1- and 2-decylidenediglycerols are low viscosity liquids and are therefore particularly suitable for making liquid detergent compositions, especially non-aqueous liquid detergent compositions. Dodecylidene diglycerol is a solid and is suitable for incorporation into a particulate detergent composition. HLB value of diglycerol is estimated from the behavior of the phase to be 9.5 to 10.5, which is C ₁₂ ethoxylated alcohol with an average ethoxylation degree of 3 to 4 (hereinafter, for convenience, the C ₁₂ EO _3-4 Say)).
However, its oil stain cleaning power is somewhat better.

These materials include anionic surfactants of the sulfate and sulfonate types and nonionic surfactants with a higher degree of ethoxylation (eg, HLB such as C _8-18 EO _5-10).
Is higher (preferably 9, more preferably 9-13)
Advantageously, it is used in combination with a co-surfactant.
The novel compounds or in combination with primary alcohol sulphate, when used in combination with C ₁₂ EO ₈ nonionic surfactants, synergistic oily soil detergency has been observed.

Straight-chain desilidene and dodecylidene triglycerol are soft liquid-crystalline solids and are suitable for incorporation into both aqueous liquid and particulate detergent compositions. Those HL
The B value is estimated to be in the range of 12-13, which corresponds to C ₁₂ EO ₈
Comparable to nonionic surfactants. These substances are
Is lower (preferably 9, more preferably 7-9)
It is most appropriate to use in combination with a _co- surfactant (eg, C _8-18 EO _2-6 ). When C ₁₂ EO ₃ was used, a synergistic oil stain cleaning power was observed.

Synthesis of Alkylidene Glycerol As indicated above, the novel alkylidene di- and triglycerols of the present invention can be synthesized by condensing the appropriate aldehyde or ketone with a glycerol oligomer or mixture of oligomers.

Although these methods generally produce more or less complex mixtures, it has been found that it is generally not necessary to isolate pure compounds in the absence of excess non-surfactant by-products.

Detergent Compositions The novel surfactants of the present invention can be incorporated into detergent compositions in any physical form (eg, powders, liquids, gels, and solid bars).

These compositions, in any physical form, generally comprise a detergent active and a detersive builder, and may optionally contain bleaching ingredients and other active ingredients to enhance performance and properties.

Detergent Active Compounds The detergent compositions of the present invention comprise a surfactant system comprising one or more detergent active compounds (surfactants), the surfactant system comprising at least a portion of the alkylidene di-substituted compound of the present invention. Or consist of triglycerol.

As mentioned above, one or more co-surfactants may be present, these are soap and non-soap anionic, cationic, nonionic, amphoteric and zwitterionic detergent active compounds, And mixtures thereof. Many suitable detergent active compounds are available and are described in the literature, for example, 'Surface-Active Agents
and Detergents ′, Volumes I and II, Schwartz, Perry
and Berch.

Preferred detergent active compounds which can be used are soap and non-soap synthetic anionic and non-ionic compounds.

Anionic surfactants are well known to those skilled in the art. Examples include alkylbenzene sulphonates, linear alkyl benzene sulfonates, especially the alkyl chain length is C ₈ -C _15; first and second alkyl sulfates, especially C ₁₂ -C
₁₅ primary alkyl sulfates; alkyl ether sulfates; olefin sulfonates; alkyl xylene sulfonates; dialkyl sulfosuccinates; and fatty acid ester sulfonates. Generally, the sodium salt is preferred.

The nonionic surfactants which may be used, the first and second alcohol ethoxylates, especially C ₈ -C ₂₀ aliphatic alcohols alcohol per mole ethoxylated with average 20 moles of ethylene oxide, per especially alcohol 1 mole include ethoxylated C ₁₀ -C ₁₅ primary and secondary aliphatic alcohols with an average 10 moles of ethylene oxide. Non-ethoxylated nonionic surfactants include alkyl polyglycosides, glycerol monoether and polyhydroxyamide (glucamide).

The total amount of surfactants present depends on the end use, for example as low as 0.5% by weight for dishwashing compositions and as high as 60% by weight for hand-washing textile laundering compositions. For textile washing compositions with a washing machine, generally 5 to 40% by weight is suitable.

Detergent builders The detergent compositions of the present invention generally also include one or more detersive builders. The total amount of the detergency builder in the present composition is suitably 5 to 80% by weight, preferably 10 to 60% by weight for powder, 5 to 25% by weight for aqueous liquid, and 5 to 25% by weight for non-aqueous liquid. Is 10 to 40% by weight.

GB as an inorganic builder that can be present
1437950 (Unilever), sodium carbonate, optionally in combination with calcium carbonate seeds; crystalline and amorphous aluminosilicates, such as GB
Zeolite disclosed in 1473201 (Henkel), GB1473202
Amorphous aluminosilicates disclosed in (Henkel) and
Crystallinity disclosed in GB1470250 (Procter & Gamble) /
Amorphous mixed aluminosilicates; and EP164514 (Hoec
hst). Inorganic phosphate builders, such as sodium orthophosphate,
Pyrophosphates and tripolyphosphates can also be present, but are less environmentally preferred.

Suitably the zeolite builder is present in an amount of 5 to 60% by weight, preferably 10 to 50% by weight. An amount of 10 to 45% by weight is particularly preferred for granular fiber laundry (washing machine) compositions. The zeolite used in most commercially available granular laundry compositions is zeolite A. However, the largest aluminum zeolite P (zeolite MAP) described in EP384070A (Unilever) can also be used to advantage. The zeolite MAP is a P-type alkali metal aluminosilicate in which the ratio of silicon to aluminum does not exceed 1.33, preferably does not exceed 1.15, more preferably does not exceed 1.07.

Organic builders which can be present include polycarboxylate polymers such as polyacrylates, acrylic / maleic copolymers and acrylic phosphinates; citrates, gluconates, oxydisuccinates, glycerol mono-, di- and trisuccinates. Monomeric polycarboxylates such as acid salts, carboxymethyloxysuccinates, carboxymethyloxymalonates, dipicolinates, hydroxyethyliminodiacetates, alkyl- and alkenylmalonates and succinates; and sulfones Fatty acid salts. This list is not exhaustive.

A particularly preferred organic builder is citrate (suitably,
5-30% by weight, preferably used in an amount of 10-25% by weight) and acrylic acid polymers, especially acrylic acid / maleic acid copolymers (suitably 0.5-15% by weight, preferably 1% by weight).
~ 10% by weight).

The builder, whether inorganic or organic, is preferably present in the form of an alkali metal salt, especially a sodium salt.

Bleaching Component The detergent composition of the present invention may also suitably contain a bleaching system. The dishwashing composition can suitably include a chlorine bleach, and the textile laundering composition is more preferably a peroxy bleach capable of producing hydrogen peroxide in an aqueous solution (eg, an inorganic peroxide). Acid salts or organic peroxy acids)
Can be included.

Suitable peroxy bleaching agents include organic peroxides such as urea peroxide and inorganic persalts such as perborates, percarbonates, perphosphates, persilicates and persulfates of alkali metals. Is mentioned. Preferred inorganic persalts are sodium perborate monohydrate and tetrahydrate and sodium percarbonate.

Particularly preferred is sodium percarbonate which has a protective coating against destabilization by moisture. GB2123
044B (Kao) discloses sodium percarbonate having a protective coating comprising sodium metaborate and sodium silicate.

The peroxy bleach is suitably present in an amount of 5 to 35% by weight, preferably 10 to 25% by weight.

Peroxy bleach can be used with bleach activators (bleach precursors) to improve the bleaching action at low wash temperatures. The bleach precursor is suitably from 1 to
It is present in an amount of 8% by weight, preferably 2-5% by weight. Preferred bleaching precursors are peroxycarboxylic acid precursors (particularly preferably peracetic acid precursors and perbenzoic acid precursors) and peroxycarbonic acid precursors. A particularly preferred bleach precursor suitable for use in the present invention is N, N, N ', N'-tetraacetylethylene-diamine (TAED).

Bleach stabilizers (heavy sequestering agents) can also be present. Suitable bleach stabilizers include ethylenediaminetetraacetic acid (EDTA) and polyphosphonates such as Dequest ™, EDTMP.

Particularly preferred bleaching systems include peroxy bleaching agents (preferably sodium percarbonate or sodium perborate monohydrate), optionally a bleaching precursor, and EP458397A, E
Includes with transition metal bleach catalysts described in P458398A and EP509787A (Unilever).

Other Ingredients The detergent composition of the present invention can include an alkali metal (preferably sodium) carbonate to enhance detergency and facilitate processing. Sodium carbonate
Suitably, it may be present in an amount of 1 to 60% by weight, preferably 2 to 40% by weight. However, compositions containing little or no sodium carbonate are also within the scope of the invention.

In granular detergent compositions, a small amount of powder structurant (powder
Powder flow properties can be improved by incorporating structurants, such as fatty acids (or fatty acid soaps), sugars, acrylic acid or acrylic / maleic acid polymers, or sodium silicate. A preferred powder structurant is a fatty acid soap, suitably comprised in an amount of 1 to 5% by weight.

Other substances that may be present in the detergent composition of the present invention include sodium silicate; an anti-redeposition agent such as a cellulose polymer; a fluorescent agent; an inorganic salt such as sodium sulfate; Foam accelerators; proteolytic and lipolytic enzymes; dyes; colored speckles; fragrances; foam regulators; This list is not exhaustive.

Liquid Detergent Compositions As mentioned above, the alkylidene di- and triglycerols of the present invention can be advantageously incorporated into aqueous and non-aqueous liquid detergent compositions.

The aqueous liquid according to the present invention is isotropic. Alternatively, it may be a structured liquid obtained by dispersing lamella droplets in an aqueous continuous phase containing a suspended particulate solid, if desired. Such structured liquids without suspended solids are disclosed, for example, in US Pat. No. 4,244,840; structured liquids with suspended solids are disclosed in US Pat.
In addition to 840, it is also disclosed in EP38101A, EP160342A and EP140452A. The liquids are EP346995A (Unileve
The peptized polymers described under r) may suitably be included in amounts of 0.01 to 5% by weight.

The non-aqueous liquid according to the present invention contains less than 5% by weight, preferably less than 3% by weight of water. The non-aqueous liquid can take the form of a particulate solid phase dispersed in the non-aqueous liquid phase, the non-aqueous liquid phase suitably comprising one or more non-ionic surfactants at 1-90% by weight, preferably 5 to 75% by weight, more preferably 20 to 60% by weight. The non-aqueous liquid advantageously incorporates a hydrophobically modified dispersant, such as hydrophobic silica, to improve physical stability. It is also advantageous to incorporate peptizers, for example the acids described in EP 266199 A (Unilever).

Examples The present invention will be further described by the following examples, but the present invention is not limited to the following examples. In the examples, parts and percentages are by weight unless otherwise indicated. Examples with numbers are examples of the present invention, and examples indicated by alphabets are comparative examples.

Examples 1-4 Synthesis and characterization of alkylidene di- and triglycerols Example 1: Synthesis of 1-decylidene diglycerol This example shows that in formula I, R ₁ = linear C ₉ H ₁₉ , R ₂ = H ,
The synthesis of compounds where A = monoglycerol is described.

1,1-dimethoxydecane (22.0 g, 0.10 mol) in dimethylformamide (100 cm ³ ), diglycerol (86.0 g,
0.52 mol) and p-toluenesulfonic acid (0.25 g)
Was heated at 100 ° C. for 7 hours. The reaction mixture was cooled, water (400 m ³ ) was added and the mixture was brought to ether (2 × 300 c.
m ³ ). Combine the ether extracts and combine with water (2
× 250 cm ³ ) and brine (250 cm ³ ) and dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure gave a crude product. Short path distillation using a Kugeller apparatus provided pure 1-decylidenediglycerol (14.7 g, 48%).

Compound characterization was performed by nuclear magnetic resonance (NMR) spectra. δ _H (360 MHz, CDCl ₃ , TMS): 0.89 (3H, t, CH ₃
−), 1.3 to 1.4 (14H, m, − (CH ₂ ) ₇ −), 1.65 (2H, m, C ₈ H
_{17 -CH 2 -), 3.5~4.4 (} 10H, m, -O-CH 2 -CH (O) -C
_{H 2 -O -), 4.88,4,98 (} 1H, t, C 9 H 19 -CH-).

1-Dodecylidenediglycerol was synthesized and analyzed using a similar method.

Example 2: this example is 2-de Siri Denji glycerol describes the synthesis of R ₁ = a straight-chain C ₈ H _17, R ₂ = methyl, A = compound a monoglycerol in formula I.

2-Decanone (0.136 mol) and diglycerol (340.0 g, 2.05 mol, 15) in dimethylformamide (340 cm ³ )
Equivalent) and p-toluenesulfonic acid (0.5 g)
Stirred at <RTIgt; 3 C </ RTI> for 3-6 hours. Cool the reaction mixture and add water (25
0 m ³⁾ was added and the mixture was extracted with ether. The ether extract was washed with water and brine and dried over anhydrous sodium sulfate. Removal of the solvent on a rotary evaporator gave a crude product. Short path distillation using the Kugeller apparatus provided pure 2-decylidenediglycerol (12.52 g, 30%).

Compound characterization was performed by nuclear magnetic resonance (NMR) spectra. δ _H (360MHz, CDCl ₃ , TMS): 0.88 (3H, t, J =
_{6.9Hz, CH 3), 1.3 (} 12H, m, - (CH 2) 6 -), 1.31,1.37 (3
H, s, O-C ( CH 3) C 8 H 17 -O), 1.65 (2H, m, C 7 H 15 -CH 2
−), 2.2 to 3.0 (2H, br m, −OH), 3.6 to 4.4 (10H, m, −O
_{-CH 2 -CH (O) -CH 2} -O-).

Example 3 Synthesis of 2-Dodecylidenediglycerol This example describes the synthesis of a compound of formula I where R ₁ = linear C ₁₀ H ₂₁ , R ₂ = methyl and A = monoglycerol.

2-Dodecanone (0.136 mol) and diglycerol (340.0 g, 2.05 mol, 15) in dimethylformamide (340 cm ³ )
Equivalent) and p-toluenesulfonic acid (0.5 g)
Stirred at <RTIgt; 3 C </ RTI> for 3-6 hours. Cool the reaction mixture and add water (25
0 cm ³ ) was added and the mixture was extracted with ether. The ether extract was washed with water and brine and dried over anhydrous sodium sulfate. Removal of the solvent on a rotary evaporator gave a crude product. Short path distillation using the Kugeller apparatus provided pure 2-dodecylidenediglycerol (21.3 g, 47%). Boiling point: 225 ℃ / 0.04m
bar.

Compound characterization was performed by nuclear magnetic resonance (NMR) spectra. δ _H (360MHz, CDCl ₃ , TMS): 0.88 (3H, t, J =
(? 17 () 6.9Hz, CH 3), 1.3 H, m, - (CH 2) 8 -), 1.31,
1.36 (3H, s, O- C (CH 3) C 10 H 21 -O), 1.65 (2H, m, C 9 H
₁₉ −CH ₂ −), 2.2 to 3.0 (2H, brm, −OH), 3.5 to 4.4 (10
_{H, m, -O-CH 2} -CH (O) -CH 2 -O-).

Example 4: Synthesis of 1-decylidene triglycerol This example demonstrates that in Formula I, R ₁ = linear C ₈ H ₁₇ , R ₂ = H
The synthesis of compounds where A = diglycerol is described.

1,1-dimethoxydodecane (11.5 g, 0.05 mol) in dimethylformamide (250 cm ³ ), triglycerol (24
0 g, 1.0 mol) and p-toluenesulfonic acid (0.5 g)
Was heated at 100 ° C. for 5 hours. The reaction mixture was cooled, water (400 m ³ ) was added and the mixture was brought to ether (2 × 300 c.
m ³ ). Combine the ether extracts and combine with water (2
× 250 cm ³ ) and brine (250 cm ³ ) and dried over anhydrous sodium sulfate. Removal of the solvent under reduced pressure gave a crude product. Short path distillation was performed using a Kugeller apparatus to remove low boiling impurities, yielding nearly pure 1-dodecylidene triglycerol (14.2 g, 70%).

Compound characterization was performed by nuclear magnetic resonance (NMR) spectra. δ _H (360 MHz, CDCl ₃ , TMS): 0.88 (3H, t, CH ₃
−), 1.3 to 1.4 (18H, m, − (CH ₂ ) ₉ −), 1.64 (2H, m, C ₁₀
H ₂₁ -CH _2- ), 3.5 to 4.4 (15H, m, -O-CH ₂ -CH (O)-
_{CH 2 -O -), 4.88,4.97 (} 1H, t, C 11 H 23 -CH-).

1-Dodecylidene triglycerol was synthesized and characterized using a similar method.

Examples 5 to 8: Detergency The detergency of oil stains was compared in a triolein removal experiment using a tergotometer.

Stain removal was evaluated using ³ H radiolabeled triolein. The knitted polyester test cloth having this stain (about 1.9%) was washed for 20 minutes with a turgotometer UR 7227. The stirring was 70 rpm, the amount of washing liquid was 500 ml, and the washing temperature was 40 ° C. The surfactant was used at a concentration of 1 g / l in distilled water in the presence of a sodium metaborate buffer (0.05 M). After washing, 4
A 1 ml sample of the wash liquor was removed and the radioactivity was measured using a liquid scintillation counter.

 The detergency (%) was calculated from the following relational expression.

In detergency _{(%) = A w / (} A s × 100) [ wherein, A _w is the total radioactivity in the wash liquor, A _s is the level of radioactivity applied to the first fabric. ] Decylidene and de de Siri Denji glycerol all, when used with primary alcohol sulphate (here PAS) and C ₁₂ EO ₈ ethoxylated alcohol is a high HLB cosurfactants, shows the cleaning behavior acting cooperatively Was.

Example 5 2-decylidene diglycerol (Example 2) and primary alcohol sulfate (coco PAS) Example 6 2-Dodecylidenediglycerol (Example 3) and Coco PA
S Example 7 2-de Siri Denji glycerol (Example 2) and C ₁₂ EO ₈ nonionic surfactant Example 8 2-dodecane Siri Denji glycerol (Example 3) and C ₁₂ EO ₈
Nonionic surfactant Examples 9 to 12: Detergency In these examples, the detergency was measured in the same manner as used in Examples 5 to 8, but the tergotometer washing liquid contained the following components in 24 ° (France) hard water: It was taken.

g / l surfactant (total) 1.00 zeolite 2.42 sodium carbonate 1.82 acrylic acid / maleic acid copolymer 0.592 Example 9 1-decylidene diglycerol (Example 1) and Coco PAS Example 10 1-Decylidene diglycerol (Example 1) and nonionic surfactant Example 11 1-Dodecylidene diglycerol (Example 1) and nonionic surfactant Example 12 1-Dodecylidene triglycerol (Example 4) and nonionic surfactant In the case of 7EO nonionic surfactant For 3EO nonionic surfactant These results indicate that 1-dodecylidene triglycerol behaves as a high HLB surfactant. 1
-Little benefit was obtained when dodecylidene triglycerol was mixed with another high HLB surfactant, 7EO ethoxylated nonionic surfactant, which has very similar performance. However, when mixed with 3EO ethoxylated alcohol which is a low HLB surfactant, improvement in detergency was observed.

Examples 13-16: Detergent compositions Examples 13 and 14: Powder detergent Powder detergents incorporating the compounds of the present invention can be made with the following formula (% by weight).

Example 15: Non-aqueous liquid detergent Examples 16 and 17: aqueous liquid detergent

Continuation of the front page (72) Inventor Can-Rodie, Abidedo Nadiyne United Kingdom, Thiester C.H.2.2.J Day, Fool, Hewitt Street 29 (72) Inventor Nicholas, Malcolm Phillippe, United Kingdom, Merseyside El 49.0 Tay Wy, Wirral, Upton, Slingsby Drive 69 (56) References JP-A-58-13530 (JP, A) (58) Fields studied (Int.Cl. ⁶ , DB name) C07D 317/22 C11D 1/68 B01F 17/32 B01F 17/38 CA (STN) REGISTRY (STN)

Claims (18)

(57) [Claims] (1) Formula I: [Wherein, R ₁ represents a linear or branched alkyl or alkenyl group, R ₂ represents a hydrogen atom or a linear or branched alkyl or alkenyl group, and the total number of carbon atoms in R ₁ and R ₂ is 7 to 17, and A represents a monoglycerol or diglycerol group. ] The compound of. 2. Formula Ia: [Wherein, n is 1 or 2. The compound according to claim 1, wherein 3. The compound according to claim 1, wherein R ₁ represents a C ₉ or C ₁₁ alkyl group, and R ₂ represents a hydrogen atom. 4. The compound according to claim 1, wherein R ₁ represents a C ₈ or R ₁₀ alkyl group and R ₂ represents a methyl group. 5. A surfactant or wetting agent comprising the compound according to claim 1. 6. A detergent composition comprising a surfactant system comprising one or more surfactants, characterized in that the surfactant system comprises a compound according to claim 1. Stuff. 7. The surfactant system according to claim 1, wherein A is a monoglycerol group. The detergent composition according to claim 6, characterized in that the composition further comprises a co-surfactant having an HLB value of at least 9. 8. The detergent composition according to claim 7, wherein the auxiliary surfactant has an HLB value of 9 to 13. 9. The detergent composition according to claim 7, wherein the co-surfactant is selected from sulfate and sulfonate anionic surfactants and ethoxylated nonionic surfactants. 10. The detergent composition according to claim 7, wherein the co-surfactant is a primary alcohol sulfate. 11. A method according to claim 7, wherein the co-surfactant is a C _8-18 alcohol ethoxylated with an average of 5 to 10 moles of ethylene oxide per mole of alcohol.
A detergent composition according to claim 1. 12. The surfactant system according to claim 1, wherein A is a diglycerol group. The detergent composition according to claim 6, wherein the compound of the formula (1) is used together with an auxiliary surfactant having an HLB value not exceeding 9. 13. The detergent composition according to claim 12, wherein the HLB value of the co-surfactant is 7 to 9. 14. The detergent composition according to claim 12, wherein the co-surfactant is an ethoxylated nonionic surfactant. 15. The method according to claim 12, wherein the co-surfactant is a C _8-18 alcohol ethoxylated with an average of 2 to 6 mol of ethylene oxide per mole of alcohol.
A detergent composition according to claim 1. 16. The detergent composition according to claim 6, which is in a liquid form. 17. The detergent composition according to claim 6, which is in the form of a non-aqueous liquid. 18. A process for preparing a compound according to claim 1, comprising reacting an aldehyde or ketone of the formula: R ₁ —CO—R ₂ with diglycerol or triglycerol.