JPS6183151A - Preparation of surfactant - Google Patents

Abstract

PURPOSE:To obtain a surfactant having light color and low irritancy to the skin and the eye mucosa, useful as cosmetic and kitchen detergent, etc., at a low cost, by reacting a natural oil or fat with a polyamine, and reacting the reaction product with monochloroacetic acid compound. CONSTITUTION:The objective compound can be produced by (1) reacting a natural oil or fat such as coconut oil, hydrogenated beef tallow, etc. with the polyamine of formula (R1-R4 are H, 1-4C alkyl, etc.; m is 0-4; n is 2-6) at 50-230 deg.C, preferably 100-180 deg.C for 3-30 hr, and (2) reacting the resultant product having 1-1+m acyl groups with the compound of formula XR5CO2M (X is halogen; M is alkali metal) (e.g. sodium monochloroacetate, monochloroa cetic acid, etc.) at 30-150 deg.C and 7-8 pH.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing a surfactant. More specifically, the present invention relates to a method for producing a 0゛ surfactant containing a specific amphoteric surfactant derived from natural oils and fats.

Amphoteric surfactant compositions have little irritation to the skin and eye mucous membranes, and are useful compounds as bases for cosmetics such as shampoos and hair rinses, and as bases for cleaning agents such as kitchen detergents and bathtub detergents. Conventionally, products obtained by reacting a reaction product of a higher fatty acid or its methyl ester with a polyamine with sodium monochloroacetate or monochloroacetic acid are known. However, ampholytes derived from higher fatty acids,
Surfactant compositions require a higher reaction temperature than those derived from fatty acid esters, and are colored yellow or yellowish brown during production, and when used as a base for cosmetics or detergents, dyes may be used. However, it has disadvantages such as inhibiting the effect of dye and requiring an increase in the amount of dye used. The reason for decolorizing such a colored amphoteric surfactant composition with a decolorizing agent such as hydrogen peroxide is that the decolorizing agent does not irritate the skin or eye mucous membranes and inhibits the action of dyes and fragrances. On the other hand, higher fatty acid methyl ester class fatty acid methyl ester is derived from transesterification of natural fats and oils with methanol, and then requires a complicated and disadvantageous process of collecting and disposing of methanol by-produced by reaction with polyamine. It is something.

Furthermore, it has the disadvantage that methanol, which is harmful to the human body, may be mixed into the amphoteric surfactant.

The present inventors have conducted extensive research on methods for producing surfactants containing amphoteric surfactants that do not have the above-mentioned drawbacks, and as a result, have arrived at the present invention.

That is, the present invention combines natural oils and fats with the general formula (1) (in the formula R1,
R2, R, and circles each independently represent HC1 to C4
alkyl group or -( aH2aH,o ), H (
(where p is an integer), m is an integer of O to 4, and n is an integer of 2 to 6]. The product (A) having an acyl group of the same formula (2)% formula (2) [wherein X is a halogen atom, R, is a C1-C4 alkylene group 1M is an alkali metal. ]→＋−（奄→→
This is a method for producing a surfactant.

The natural oils and fats used in the present invention include coconut oil, palm oil,
Examples include vegetable oils and fats such as castor oil and olive oil, animal oils and fats such as beef tallow, and hydrogenated natural oils and fats such as hydrogenated beef tallow.

Preferred are coconut oil and hydrogenated beef tallow.

The amine used in the present invention is a polyamine represented by the general formula (1). In the general formula (1), p is preferably 1 to 5. Two n's may be the same or different. Furthermore, when there are multiple people (m is 2 to 4), the boundaries between the two may be the same or different.

Polyamines represented by general formula (1) (hereinafter referred to as polyamines) include polyalkylene diamines such as ethylene diamine, propylene amine, and hexamethylene diamine, diethylene triamine, triethylene tetramine,
Polyalkylene polyamines such as tetraethylene pentamine, hentaethylene hexamine, and cyhexamethylene triamine, N-substituted polyamines such as the above-mentioned polyalkylene diamines and polyalkylene polyamines (N-substituted products include N-; N, N- ;N, N, N'-;N,
It includes various substituents such as N, N'1N"-. For example, N-alkyl/L/(C1~
C4) substituted product, N-hydroquinethyl substituted product, or -(CH2CH20)p■ substituted product when p is an integer of 2 or more. Among the above polyamines, preferred are N1 N-dialkyl substituted polyalkylene diamines and N-hydroquinethyl substituted polyalkylene diamines, and particularly preferred are methylaminopropylamine, diethylaminoethylamine, aminoethyl It is ethanolamine.

It is represented by the general formula (2) used in the present invention. Compound(
In the compound (hereinafter referred to as the compound of general formula (2)), X is a halogen atom, and examples thereof include chlorine and bromine. Ma is an alkylene group with numbers 01 to C, and can include groups such as ali, methylene, ethylene, propylene, and isobutylene. Further, M is an alkali metal, and examples thereof include sodium and potassium.

Among the compounds of general formula (2), preferred is monochlorosodium acetate. Monochloroacetic acid may be used in combination with an alkali such as caustic soda.

In the production of reaction products between natural fats and oils and polyamines,
The amount of natural oil and fat used varies depending on the type of polyamine used, but is usually 1 to 1+m of the primary or secondary amine groups in the polyamine (m is the same as m in general formula (1)).
Preferably, it is reacted (acylation reaction) with one (in the necessary amount). In this case, the reaction product can also be further converted into imidacillin if possible. The reaction temperature is usually 50°C.
~230”C.

Preferably 100-180°C, reaction time usually 3-3
Although a catalyst is not particularly required, a catalyst such as caustic soda can also be used. Glycerin, which is a by-product of the reaction, may be removed, but it is preferable not to. Glycerin, a by-product, can be effective as a solubilizer, low-temperature stability improver, humectant, etc. in the preparation of cosmetics and detergents. preferable. (The effect is better than adding glycerin afterwards). Note that unreacted polyamine can be removed if necessary.

Next, in the reaction between the reaction product obtained in the above reaction and the compound of general formula (2) (ampholyte reaction),
The amount of compound used varies depending on the type of reaction product, but usually one of the reaction products (acylated polyamine) (
1 (mo/L/) to 2m+4 (mo/v) (m is the same as above) for each compound of the general formula (2) is the amount necessary for reaction. , the reaction temperature is usually 30 to 150°C, which is the amount necessary to carboxyalkylate or betainate at least one of the amine groups.
Preferably 60-100'C.

The reaction time is usually 3 to 10 hours. A solvent is not particularly required, but if used, water is preferred, and the pH is preferably maintained at 7 to 8 with an alkali such as caustic soda.

The surfactant of the present invention thus obtained can be used even if it contains glycerin, sodium glycolate, common salt, etc., or even if it contains other surfactants.

The surfactant obtained by the method of the present invention can be used as a base for cosmetics such as shampoos and hair conditioners, and as a base for cleaning agents such as kitchen detergents. When using it as a base for detergents such as shampoo and kitchen detergent, it is diluted with water. Usually the amount used is 1 to 5
0% by weight (calculated as anhydride), preferably 5 to 25% by weight.

Other components can be used in combination with the above, and examples of such combinations include general anionic surfactants, nonionic surfactants, and amphoteric surfactants (excluding the composition of the present invention). Examples include common detergent bases and auxiliaries such as solubilizers, diluents, fragrances, dyes, fluorescent dyes, preservatives, inorganic or organic bilges, and pH adjusters. Also, when used as a hair rinse, it is diluted with water.The amount usually used is 0.1 to 10% by weight (calculated as anhydrous).
and preferably 1 to 5 weight ratio. In the case of hair rinses, other ingredients can also be used in combination, such as general cationic surfactants, 1 nonionic surfactants, and amphoteric surfactants (excluding the composition of the present invention). ) Usual hair rinse bases and adjuvants such as solubilizers, diluents, fragrances, dyes, preservatives, and pH adjusters.

The surfactant of the present invention is light in color and does not contain by-products such as methanol, and when used in cosmetic bases such as Nyanbu and hair rinse agents, it is less irritating to the skin and eye mucous membranes and is less irritating to hair. It has characteristics such as giving an excellent texture. In addition, since it uses natural oils and fats as ingredients, it can be produced at low cost, and when by-product glycerin is not removed, it acts as a solvent, allowing the reaction to occur uniformly and yielding a high-performance composition. Furthermore, when it is in the form of an aqueous solution, it has excellent low-temperature stability.

The present invention will be further explained below with reference to Examples, but the present invention is not limited thereto.

Example 1 Coconut oil 650. ! 9 (1 mol) and dimethylaminopropylamine 306.9 (3 mol/L/) were heated in a reaction vessel equipped with a reflux condenser at 140 to 160°C under a nitrogen stream until the primary amine value became 5 or less. Allowed time to react. Then, it was cooled to 80°C, 1900.9% water and 386g (3.3mol/l) of monochrome acetic acid sorter were added, and the mixture was heated to 80°C.
Stirring was continued for 7 hours while maintaining p)I at 7 to 8 with C (a small amount of caustic soda was added during the reaction). The hue of this product was 120 according to the AP HA method.

Comparative Example 1 Coconut oil fatty acid 630g (amo)V) and dimethylaminopropylamine aos, 9 (8 mol) were heated in a reaction vessel equipped with a reflux condenser at 170 to 180°C under a nitrogen stream until the primary amine value was 5 or less. The reaction was allowed to take place for 6 hours.

Next, the mixture was reacted with sodium monochloroacetate in the same manner as in Example 1 to obtain an amphoteric surfactant. This hue is API (A
According to the law, it was 300.

Example 2 Coconut oil 650.9 (1 mo/I/) and amine ethylethanolamine 312 g (8 moles) were mixed in a reaction vessel equipped with a reflux condenser to reduce the primary amine value at 150 to 160 °C under a nitrogen stream. The mixture was allowed to react for 4 hours until it became 5 or less, and then allowed to react for 15 hours at the same temperature under conditions of 50 mmHH while distilling the water produced. Soda 585.
7 (5 mo/v) and adjust the pH to 7-8 at 80°C.
Stirring was continued for 7 hours while maintaining the pH (pH was adjusted with a small amount of caustic soda during the reaction). This object's hue API
(It was A Law Te 140.

Comparative Example 2 Yang oil fatty acid 6sog (smo/L/) and aminoethylethanolamine 512ji (3 mol) were heated at 170 to 180°C under a nitrogen stream in a reaction vessel equipped with a reflux condenser.
The reaction was carried out for 6 hours until the primary amine value became 5 or less, and then the reaction was carried out for 15 hours at 150 to 160°C while distilling the produced water under conditions of 5 mm and 11 g.Then, the same method as in Example 2 was carried out. was reacted with monochlorosodium acetate to obtain an amphoteric surfactant. This hue was 400 by the AP HA method.

Example 8 Hydrogenated beef tallow 860p (1 mo/I/) and diethylaminoethylamine 360p. @(3,1 mo/L/ ) in Example 1
After reacting in the same manner as above, excess diethylaminoethylamine was distilled off. Next, 500 g of water and 410 g (3.5 mol) of sodium monochloroacetate were added to obtain the same surfactant of the present invention as in Example 1. This hue is AP
It was 100 by the HA method.

Test Example 1 Nyanpuwo 75 was obtained using the following formulations IVkL1 and Nn2. When I used this product, it created a rich lather and left my hair supple after washing.

Formulation N [11 Lauryl sulfate trieta)-luamine 15 g (40% aqueous solution) Coconut oil fatty acid jetanolamide 5 Solution of the activator of the present invention obtained in Example 1 30 Fragrance, dye
trace water
50 prescription Nn2 Sodium polyoxyethylene lauryl ether sulfate
10g (30 multi-aqueous solution) Coconut oil fatty acid jetanolamide 5 Activator solution of the present invention obtained in Example 3 35 Fragrance, dye
trace water
50 Test Example 2 Activator solution of the present invention obtained in Example 3 20.9 Propylene Glyco/l/5 Water

75 If you prepare a hair rinse agent by dissolving a small amount of fragrance and dye in the liquid with the above composition and adjusting the pH to 4 with citric acid, and diluting this with 100 times the amount of water, it will improve the smoothness and softness of the hair. The hair has increased elasticity and a good texture, making it easier to comb and style the hair.

Test Example 3 2 of each of the active agents of the present invention obtained in Examples 1, 2, and 3
A skin irritation test was conducted using a patch test using an aqueous solution of H (active ingredient equivalent). In other words, a lint cloth coated with the sample was applied to the inner side of the upper arm of 15 male and female participants, and a batch test adhesive was placed on top of it.After 48 hours, the presence or absence of erythema or other changes was examined. I didn't admit it.

Claims (1)

[Claims] Natural oils and fats and general formula (1) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (1) [In the formula, R_1, R_2, R_3 and R_4 each independently represent H, an alkyl group of C_1 to C_4 or -(C
H_2CH_2O) pH (where p is an integer), m is an integer of 0 to 4, and n is an integer of 2 to 6. ] A product having 1 to 1+m (m is the same as m in general formula (1)) acyl groups (A
) is reacted with a compound represented by the general formula (2) XR_5CO_2M (2) [in the formula, Method for producing activator.