JPS5984994A - Liquid detergent composition containing dipeptide compound - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a cleaning composition, in which a liquid containing a dipeptide compound, more particularly a liquid cleaning composition characterized in that the liquid containing a dipeptide compound contains an N-(N-)' sylglycyl)glycine compound. It is related to.

In recent years, an increasing number of consumers are demanding liquid cleansers that are gentle on the skin and liquid cleansers that are highly biodegradable, and liquid cleansers that meet these demands are on the market. Ta. Typical surfactants used as bases in these detergents include N-acylamino acid salts, amidoamine type amphoteric surfactants, and acylated peptides. Among these, acylated peptides have disadvantages such as the appearance of natural 9 and a peculiar odor. These shortcomings are thought to be caused by impurities such as lipids and polysaccharides contained in natural peptides, and volatile components such as aldehydes, ketones, keto acids, and sulfides that are generated when impurities are oxidized. In order to improve the drawbacks of acylated natural peptides, it was necessary to remove organic substances such as lipids and polysaccharides contained in natural proteins.

However, it was difficult to completely remove these impurities, and the improvement effect of the imbued product C was insufficient.

The inventors of the present invention aimed to improve all the drawbacks of conventional acylated peptides, and found that a specific dipeptide compound did not have these drawbacks, and developed the present invention. It took me a thousand seconds to complete it.

That is, the present invention relates to the general formula (I) 1eC0NHCH2CONI(CH+C00M
(T) (wherein RCO is I having 8 to 22 carbon atoms
l'+i ll1j acid residues are all represented, and M is a hydrogen atom, an alkali metal atom, an ammonium group, or an alkanolamine cationic residue) It is something.

RC of the general formula (1) of the dipeptide compound in the present invention
The O- group is at least one selected from residues of saturated fatty acids and unsaturated fatty acids having 8 to 22 carbon atoms, preferably 8 to 18 carbon atoms. This saturated fat r? Examples include caprylic acid, capric acid, lauric acid,
Examples include myristic acid, normitic acid, stearic acid, erucic acid, and instearic acid. The unsaturated fatty acids that are produced include tadoebori nolic acid, lylunic acid, and oleic acid. Further, the RCO- group may be a residue of a mixed fatty acid, and examples of this mixed fatty acid include coconut oil fatty acid,
Examples include palm oil fatty acids, palm kernel oil fatty acids, beef tallow fatty acids, and bran oil fatty acids.

M in the general formula (1) of the dipeptide compound of the present invention represents a hydrogen atom, an alkali metal atom, an ammonium radical, or an alkanolamine cation residue ff. Examples of alkali metals include (s)IJum, potassium, etc.;
, fc include heptanoethanolamine, jetanolamine, and triethanolamine.

The dipeptide compound of the present invention can be easily obtained according to a known method for acylating amino acids. for example,! N-
The dipeptide compound of the present invention is obtained by adding a chloride of a fatty acid and acylating at 30° C. or lower. Note that N, which is the starting material for the dipeptide compound of the present invention,
-Glycylglycine is obtained from lyglycine by a common manufacturing method.

The dipeptide compound in the composition of the present invention is usually 3-4Q
By blending 11A%, preferably 5 to 30wt, the skin is free from turbidity and has no peculiar odor.
In addition, a liquid detergent composition with detergency can be obtained.

The composition of the present invention can be used for various purposes such as
It can be used in applications such as body washes, hard surface cleansers, shampoos, liquid facial cleansers, Lixodone soups, and laxative cleansers. The composition of the present invention includes fragrances, colorants, humectants, such as those commonly used in liquid cleaning agents,
Auxiliary agents such as virgoo, hydrotropes, preservatives, etc. can be added as appropriate.

Furthermore, there is no problem in adding other types of anionic surfactants, cationic surfactants, amphoteric surfactants, and nonionic surfactants for the purpose of fully adjusting detergency and foaming. These include fatty acid soap A, high M alcohol sulfate ester salt, polyoxyethylene higher alcohol sulfate ester salt, higher alcohol phosphate ester and its salt, polyoxyethylene higher alcohol phosphate ester and its salt, and polyoxyethylene higher alcohol phosphate ester and its salt. Ethylene product count Fatty acid phosphate ester and its salt, sulfonated higher fatty acid salt, sulfonated higher fatty acid alcohol ester salt, higher alcohol sulfosuccinate ester salt, isethionic acid higher fatty acid ester salt, α-sulfo higher-y alcohol acetate ester salt, higher grade Alkylolamines and higher fatty acids such as alkyl dimethylbenzylammonium km-, higher alkyl amines, higher algyl trimethyl ammonium salts, lauric acid jetanolamide, stearic acid jetanolamide, lauric acid monoethanolamide, and stearic acid monoethanolamide condensate and part 1
Chin L/Nogizide example additives, boriogyshiethylene higher fatty acid monoethanolamide phosphoric acid sprue, N-long chain acyl acidic amino? Salt ′-゛sarcosine salt, N-
N- with long chain acyl-N-alkyl-β-alanine salts
Long-chain acyl-γmino acid salts, higher alkylaminopropionate salts such as lauryl aminopropionic acid, higher alkyliminodiacids such as lauryl imino di t1r salts/Th
, i, <% p6 k2 Alkyl dimethyl betaine, higher alkyl dihydroxyethyl betaine, N-fulkyloyl-N'-(2-hydroxyethyl)-N'-hydroxymethylethylenediamine salt, N-alkyloyl-N~(2- Examples include, but are not limited to, amine amide compounds such as (hydroxyethyl)N/, N/-biscarboxymethylethylenediamine, and the like.

The composition of the present invention is mild to the skin and highly biodegradable, and has the effect of being less cloudy even at low temperatures and having no peculiar odor compared to conventional detergents containing N-acyl peptides. do. It is not clear why the composition of the present invention has such an effect, but unlike, for example, an acylated peptide derived from the natural protein collagen, the N-(N-acylglycyl)glycine of the composition of the present invention contains lipids, It should not contain decomposition products such as polysaccharides, and therefore, cloudiness and peculiar odors caused by these impurities and volatile components such as aldehydes, tetra, keto acids, and sulfides generated by oxidation of impurities will occur. It seems that there is no such thing.

Further, the misfire #J:c will be explained in detail using an example.

Synthesis of Synthesis N-glycylglycyl 30.0f (0,234 mol) and sodium hydroxide 16.6F (0,415 mol) were dissolved in a mixed solvent of 7240 tdO of tetrahedral oxide and 240 tdO of water, and incubated at 25°C to 30°C. 1-・ta. Add lauric acid chloride 39.
4F (0.18 mol) was added between 211;'+.

After further aging at the same temperature for 1 hour, 1E1) salting was added to bring the pIl to 1, and the powder was dried. -(N-fluoroylglycine)glycine 517 was obtained. Yield is 91.
4, the free fatty acid content in the product was 9.1. Analysis of the total infrared content of this product revealed that the infrared absorption spectrum showed the occurrence of amide absorption at 1640 tyn-', the occurrence of absorption due to -COOI (group) at 1730 cn+-'', and 1800 Crn- Acylation was confirmed by the disappearance of absorption by coca group of fatty acid chloride.

Production example 2. Fu--1 (N22J Mi Ilguri/Ka-),
//'-+7. Synthesis of N-glycylglycine 66.59 (0,!52 mol)
and sodium hydroxide 40.69 (1,01 mol) Kechitrahydrofuran 567 tne 1 water 5 (i 7 me 6
Dissolve in the mixed solvent of 14 and heat from 20℃ to 30℃. Cocoyl chloride 91.6
f (0.42 mol) was added dropwise over 2 hours. After further aging at the same temperature for 1 hour, concentrated hydrochloric acid was added to 1) H gold 1
When the precipitated solid KP was taken and dried, N
-(N financial V was less than 10 cm. This product was analyzed by total infrared spectroscopy, and it was found that the infrared absorption spectrum was 1640/M-', the occurrence of absorption due to the amide group, 1
Acylation was confirmed from the occurrence of absorption by the -COOIi group of 730 tyn-' and the slight loss of absorption by the -coc and a groups of 1800 tyn-''.

N-glycylglycine 66.5F (0.52 mol) and sodium hydroxide 40.61 (1.01 mol) were added to 600 ml of tetrahydrofuran. The mixture was dissolved in a mixed solvent of 600-g of water, and 98.69 (0.4 mol) of myristoyl chloride was added dropwise to this solution kept at 25-30° C. over 2.5 hours while stirring. After aging for a further 1 hour, the same treatment as in Example 1 was carried out until the content was less than 10.

When this product was analyzed by total infrared spectroscopy, it was found that in the infrared absorption spectrum, absorption occurred due to the amide group at 1.640 cm-'', absorption occurred due to the -coon group at 1,730 cm-'', and absorption occurred at 1800 cm-''. It was confirmed that the fatty acid chloride of ``-Coci'' had been alylated due to the disappearance of its absorption by -Coci.

Mix 1g of Example 1 to create a hypoallergenic shampoo total of 1li
1. ! 11',? did.

ON -(N'-lauroylglycyl)glycine *Midazolinium vequin (38% aqueous solution) 200 Polyoxyethylene argyl ether sulfate (30% aqueous solution) 15 0 Laurin 1° Diethanolamide 20 Ethylenediaminetetraacetic acid tetrasodium salt 0.5C) Citric acid (amount to adjust pH to 7) Appropriate amount 100 parts*, obtained by neutralizing the product obtained in Production Example 1 with sodium hydroxide.

Example 2 A kitchen detergent was prepared by mixing the following ingredients.

0N-(N'-cocoylglycyl)glycine sodium salt (25% aqueous solution) 50 parts Sodium alkanesulfonate (30%) 300 Urea 20 Lauric acid diethanolamide 2100 parts **The product obtained in Production Example 2 was mixed with water. Neutralized with sodium oxide.

Example 3 A furniture cleaning agent was manufactured by mixing the following components.

・N-(N'-Myristoylglycyl)glyol Sodium lauryl sulfate 150 Lauric acid diethanolamide 20 Water
53100 j'l+! *** + Total sodium hydroxide obtained in H Preparation Example 3,
neutralized with.

It was observed that each of the liquid detergents of Examples 1 to 3 had good detergency9 and caused little irritation to the skin.

Comparative Examples 1 to 3 All liquid cleaning agents were manufactured in the same manner as in Examples 1 to 3 except that the acylated product of Tido was used (Comparative Examples 1 to 3).

Each liquid cleaning agent'(i
The samples were left at 740°C and 0°C for one week, respectively, and checked for turbidity. The results are shown in Table 1.

From the results shown in Table 1, it can be seen that the liquid detergent containing the dipeptide compound of the present invention has improved odor and turbidity compared to the conventional liquid detergent containing the acylated product of natural peptide. It's obvious.

l MochiπF Applicant Kawaω■ Fine Chemical Co., Ltd. 66
3-

Claims (1)

[Claims] 1. General formula (1) % formula % (1) (wherein I<, CO represents all fatty acid residues having 8 to 22 carbon atoms, M is a hydrogen atom, an alkali metal atom, 1. A liquid detergent composition comprising a dipeptide compound (representing an ammonium group or an alkanolamine cationic residue). 2. The composition according to claim 1, wherein the compound represented by general formula (1) is N-(N'-cocoylglycyl)glycine sodium salt. 3. The composition according to claim 1, wherein the compound represented by the general formula (1) is N-1N-lauroylglycyl)glycine sodium salt. 4. The composition according to claim 1, wherein the compound represented by general formula (1) is N-(N-cabroylglycyl)glycine sodium salt. 5. The composition according to claim 1, wherein the compound represented by the general formula CI) is N-(N-stearoylglycyl)glycine sodium salt. 6. The composition according to claim 1, wherein the compound represented by the general formula (I) is N-(N-oleoylglycol)glycine sodium salt. 7. The #ll composition according to claim 1, wherein the compound represented by the general formula (I) is N-(N'-cocoylglycyl)glycine ammonium salt. 8. The composition according to claim 1, wherein the compound represented by general formula (1) is N-(N-cocoylglycyl)glycine triethanolamine salt. 9. The t11 product according to claim 1, wherein the compound represented by general formula (1) is N-(N'-permoylglycyl)glycine sodium salt.