JP2002332494A - Detergent composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a surfactant composition satisfying a foam-generating property on cleasing and a conditioning property on foaming and soaking, and a detergent composition containing the same. SOLUTION: This surfactant composition consists of an isomeric mixture of decyl glyceryl ether obtained by using an isomeric mixture of decyl alcohol obtained by an oxo reaction from propene trimer as a raw material, and the detergent containing the composition is also provided.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a surfactant composition having excellent foaming properties at the time of washing and conditioning properties at the time of foaming and rinsing.

[0002]

2. Description of the Related Art In detergents such as soaps, shampoos, facial cleansers, whole body detergents, dish detergents, laundry detergents, etc., anionic surfactants, nonionic surfactants,
Amphoteric surfactants and cationic surfactants are used, and these are selected according to the purpose and sometimes used in combination.

For example, non-ionic surfactants having low foaming properties are mainly used for fully automatic dishwashers and detergents for clothes, since they are required to be free of foam. In consideration of slipping and washing feeling of the hair, on the contrary, good foaming is required even in a lot of dirt,
An anionic surfactant excellent in foaming property is mainly used. In addition, a cationic surfactant is blended as a bactericidal component in a disinfecting handwash, etc., but since the cationic surfactant hardly foams, a nonionic surfactant or an anionic surfactant is used in combination. I have.

Among these detergents, in which foam needs to be formed, an amphoteric surfactant, a long-chain fatty acid alkanolamide compound and the like are used in combination with the above-mentioned surfactants for the purpose of improving the foam performance. But the effect is still not satisfactory. In addition, in shampoos and the like for washing hair, in addition to detergency, conditioning performance at the time of lathering and rinsing is also an important factor.However, the more foaming effect and washing effect, the more the hair becomes entangled during lathering and rinsing. There is a tendency for squeaks to occur, and there has been a demand for a cleaning agent having both of these properties.

[0005] On the other hand, glyceryl ether exhibits various properties depending on the length and shape of the alkyl group (branched or straight chain), the number of glycerin, and the number of alkyl groups, and is used as an emulsifier, a dispersant, a detergent, and the like. It is an excellent nonionic surfactant. However, none of the glyceryl ethers conventionally known as components of the detergent composition satisfy both the foaming property at the time of washing and the conditioning property at the time of foaming and rinsing.

[0006]

DISCLOSURE OF THE INVENTION The present invention provides a surfactant composition having both foaming properties at the time of washing and conditioning properties at the time of lathering and rinsing, and a detergent composition containing the same. The purpose is to do.

[0007]

Means for Solving the Problems The present inventors have found that an isomer mixture of glyceryl ether obtained from an alcohol obtained by the oxo reaction from a trimer of propene has a high foaming effect during washing, In addition, they found that they had excellent conditioning properties during lathering and rinsing, and could be suitably used as a surfactant composition.

That is, the present invention provides a surfactant composition comprising a mixture of decyl glyceryl ether isomers obtained from a mixture of decyl alcohol isomers obtained by an oxo reaction from a trimer of propene, and a detergent composition containing the same. It provides things.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION The decylglyceryl ether isomer mixture used in the present invention is obtained from an alcohol obtained by an oxo reaction from a trimer of propene as a raw material. Or an isomer mixture of decyl alcohol having a methyl branch.

[0010]

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The decyl glyceryl ether isomer mixture used in the present invention is prepared by a method of synthesizing and hydrolyzing glycidyl ether using the above decyl alcohol isomer mixture and epihalohydrin such as epichlorohydrin as raw materials. It can be synthesized by a known method such as a method of directly reacting glycerin with an acid catalyst, a method of reacting the above decyl alcohol isomer mixture with glycidol using an acid or basic catalyst, and a mixture of decyl alcohol isomer mixture and epihalohydrin. Is preferred. The resulting decyl glyceryl ether is a mixture of linear or methyl-branched isomers, similar to the starting alcohol.

The straight chain glyceryl ether having an alkyl chain length of 8 to 10 has a very high foaming effect, but the conditioning property at the time of rinsing is not satisfactory. If the alkyl chain length is too short, it can act as a solvent to dissolve oil stains and wash them, but the foaming effect is low. Also, when the alkyl chain length is long, it functions as an emulsifier or a detergent, but the foam amount is rather reduced. Those having a longer chain length act as oils and have high functions as skin care agents and treatment agents, but have no effect on foaming properties. In addition, dialkyl and polyglycerin act as antifoaming agents, and have an adverse effect on foaming properties. However, the decyl glyceryl ether isomer mixture used in the present invention is
It has both high foaming properties during washing and excellent conditioning properties during foaming and rinsing.

The content of the surfactant composition comprising the above-mentioned decylglyceryl ether isomer mixture in the cleaning composition of the present invention is compatible with both foaming property during washing and conditioning property during foaming and rinsing. From viewpoint, 0.1-1
0% by weight, especially 0.5 to 5% by weight, is preferred.

In the cleaning composition of the present invention, various surfactants used in ordinary cleaning agents can be used in combination with the above-mentioned surfactant composition of the present invention.

Examples of anionic surfactants include alkyl sulfates, alkyl benzene sulfonates, polyoxyalkylene alkyl ether sulfates, alkyl sulfosuccinates, sulfosuccinate surfactants, α-
Olefin sulfonate, polyoxyalkylene alkylphenyl ether sulfate, glyceride sulfate, amide ether sulfate, polyoxyalkylene fatty acid amide ether sulfate, alkyl phosphate ester salt, polyoxyalkylene alkyl ether phosphate ester salt, polyoxy Alkylene phenyl ether phosphate salt,
Glyceride phosphate ester salt, amino acid surfactant, fatty acid salt, acylated sarcosine salt, polyoxyalkylene (hydroxy) alkyl ether carboxylate,
Examples include amide carboxylic acid, amide ether carboxylate, alkyl (hydroxy) ether carboxylate, alkane sulfonate, α-sulfofatty acid salt ester salt, acylated isethionate salt, and taurate surfactant.

Examples of the nonionic surfactant include polyoxyalkylene alkyl ethers, polyoxyalkylene fatty acid esters, polyoxyalkylene sorbitan fatty acid esters, polyoxyalkylene sorbite fatty acid esters, polyoxyalkylene glycerin fatty acid esters, and monoglycerides. And sorbitan fatty acid ester-based and long-chain fatty acid alkanolamide-based surfactants.

Examples of the amphoteric surfactant include betaine acetate, betaine amide acetate, sulfobetaine, amidosulfobetaine, imidazolium betaine, amino acid, amidoamine, phosphobetaine, alkylamine oxide, amidoamine oxide and the like. Surfactants.

Examples of the cationic surfactant include a quaternary ammonium salt represented by the following general formula (1) or (2).

[0019]

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[Wherein at least one of R ¹ , R ² , R ³ and R ⁴ is an alkoxy, alkenyloxy, alkanoylamino or alkenoylamino group having a total of 8 to 28 carbon atoms] substituted indicates an alkyl group or alkenyl group optionally residual represents a benzyl group, an alkyl group or hydroxyalkyl group or the total number of moles added 10 following the polyoxyethylene group having 1 to 5 carbon atoms, Z ^- is halogen Represents a compound ion or an organic anion. ]

[0021]

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[Wherein at least one of R ⁵ and R ⁶ is an alkyl group which may be substituted by an alkoxy group, alkenyloxy group, alkanoylamino group or alkenoylamino group having 8 to 28 carbon atoms in total. Or an alkenyl group, and the other group represents a benzyl group, an alkyl group having 1 to 5 carbon atoms or a hydroxyalkyl group, and R ⁷ and R ^{8 each} have 2 to 2 carbon atoms.
3 represents an alkylene group, Z ⁻ has the same meaning as described above, and m and n represent an integer of 1 to 20. ]

[0023] Z ^- in particular chloride ions are preferred as.

One or more of the above surfactants can be selected and used depending on the purpose, and the weight ratio to the surfactant composition comprising a mixture of decylglyceryl ether isomers (ordinary surfactant) : (Surfactant composition of the present invention)
Is preferably 30: 1 to 1:30, particularly preferably 20: 1 to 1: 1.

Further, the detergent composition of the present invention may contain components used in ordinary detergents according to the purpose. Such components include preservatives, bactericides, chelating agents, vitamins, anti-inflammatory agents, anti-dandruff agents, humectants (propylene glycol, glycerin, diethylene glycol monoethyl ether, sorbitol, panthenol, etc.), conditioning components ( Higher alcohols, ester oils, cationic polymers, silicone compounds and derivatives thereof, etc., pearling agents (ethylene glycol distearate, etc.), coloring agents (dyes, pigments, etc.), viscosity modifiers (methyl cellulose, polyethylene glycol, ethanol, etc.) ), PH adjusters (such as citric acid and potassium hydroxide), salts (such as sodium chloride), plant extracts, fragrances, pigments, ultraviolet absorbers, and antioxidants.

The detergent composition of the present invention can be produced according to a conventional method, for example, a hair shampoo, a whole body cleanser, a face wash,
It can be used as a hand washing agent, a dishwashing agent or the like.

[0027]

EXAMPLES Production Example In a reactor, 570 g (3.60 mol) of an isomer mixture of decyl alcohol obtained by an oxo reaction from a trimer of propene.
And boron trifluoride ether complex 4.26 g (0.0300 mol)
And dehydrated under reduced pressure at 100 ° C. and 1.1 kPa. After that, epichlorohydrin 277.
5 g (3.00 mol) was added dropwise over 1 hour. After aging at 90 ° C for 2 hours and confirming disappearance of epichlorohydrin by gas chromatography (GC), 5.00 g (0.0600 mol) of a 48% by weight aqueous sodium hydroxide solution (48% NaOH) was added, and the temperature in the bath was adjusted. 114
Excess alcohol was distilled off under reduced pressure at ~ 140 ° C and a pressure in the tank of 0.67 kPa to obtain crude decylhalohydrin ether. To the above crude decyl halohydrin ether, 300 g of 48% NaOH (3.60 mol
l) and 420 g of water were added, and the mixture was stirred under reflux at 110 ° C. for 6 hours. G
After confirming disappearance of the halohydrin ether with C, 50 g of ethanol was added and the mixture was separated at 100 ° C., and the lower layer was removed. The obtained crude decyl glycidyl ether was heated at a temperature of 115-120.
Distillation and purification were conducted at a temperature of 0.53 kPa and a temperature of 0.53 kPa to obtain 398.5 g of decyl glycidyl ether. Decyl glycidyl ether 200
g (0.861 mol), 10.3 g (0.172 mol) of acetic acid, 48% NaOH
3.6 g (0.043 mol) and 27.3 g (1.722 mol) of water were added,
Stir at 200 ° C. for 4 hours. After confirming disappearance of glycidyl ether by GC, 10.8 g (0.129 mol) of 48% NaOH was added, and the mixture was stirred under reflux for 2 hours. The reaction was terminated by confirming disappearance of the ester by GC. Remove sodium acetate by washing with water,
After dehydration under reduced pressure at 100 ° C. and 1.1 kPa, 140 g of a decylglyceryl ether isomer mixture which is a colorless transparent viscous liquid
I got Purity (GC area%) 95%. 35% yield from epichlorohydrin.

Example 1 Using the decyl glyceryl ether isomer mixture obtained in the Production Example, a hair cleansing composition having the composition shown in Table 1 was produced by a conventional method, and the foaming amount, fingering during lathering and The feel to the hair during rinsing was evaluated. The results are shown in Table 1.

<Evaluation Method> 1 g of the detergent composition was applied to a 20 g (15 cm) hair tress of healthy Japanese women in their 20s and 30s, foamed for 30 seconds, and then rinsed and dried with a dryer. This operation was performed by 10 expert panelists, and the foaming amount at that time, finger passing during lathering, and feeling to the hair during rinsing were sensory evaluated according to the following criteria. Average score of 3.5 or more ◎, 2.5-3.4 ○, 1.5-2.4 △, 1.4
The following was judged as x.

(1) Foaming amount Very good lathering: score 4 Sufficient lathering: score 3 lathering felt insufficient: score 2 almost no lathering: score 1

(2) Finger passage at the time of lathering Hair is very good, finger passage is very good: score 4 Hair entanglement is small and finger passage is good: score 3 Hair is slightly entangled and finger passage is unsatisfactory: Score 2 Hair is entangled, finger penetration is strong, poor: Score 1

(3) Feeling to hair during rinsing Smooth and very good without squeaking: score 4 Smooth and weak and good squeaking: score 3 Slight squeaking slightly, and smoothness dissatisfied: score 2 squeaking strong: poor 1

[0033]

[Table 1]

Example 2 A shampoo having the following composition was produced by a conventional method. (Ingredient) (% by weight) Polyoxyethylene (2) sodium lauryl ether sulfate 10 Sodium lauryl ether sulfate 5 Decyl glyceryl ether isomer mixture (Production example) 3 Benzalkonium chloride aqueous solution (50% by weight) 1 Ethylene glycol distearic acid 2 Silicone emulsion (BY-22-062; Dow Corning Toray) 2 Ethanol 1 EDTA 0.5 Sodium benzoate 0.5 Fragrance 0.5 Citric acid aqueous solution Appropriate amount Purified water Balance

This shampoo was excellent in foaming property during washing and conditioning property during foaming and rinsing.

[0036]

The surfactant composition of the present invention is excellent in both foaming property during washing and conditioning property during foaming and rinsing.

 ────────────────────────────────────────────────── ─── Continuing on the front page (72) Inventor Mitsuru Uno 1334 Minato, Wakayama-shi, Wakayama Prefecture F-term (reference) 4C083 AC102 AC171 AC172 AC302 AC312 AC422 AC532 AC692 AC782 AD152 CC38 EE07 4D077 AB10 AC01 AC07 BA07 CA15 CA17 DB06Z DC02X DC02Z DC08Z DC14Z DC19X DC20X DC24X 4H003 AA01 AB27 AB31 AC03 AE05 DA02 DA17 EB07 EB08 EB09 EB16 EB37 ED02 ED28 FA18

Claims (2)

[Claims] 1. A surfactant composition comprising a decyl glyceryl ether isomer mixture obtained from a decyl alcohol isomer mixture obtained by an oxo reaction from a propene trimer. 2. A detergent composition comprising the surfactant composition according to claim 1.