# US 4,400,295 A · Emulsifier composition

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- Number: US 4,400,295 A
- Document ID: US4400295A
- Status: Granted
- Kind: A
- Application number: 06/130,858
- Filed: 1980-03-17
- Granted: 1983-08-23
- Earliest claimed: 1979-03-24
- Assignees: Loire Cosmetics Co., Ltd.
- Inventors: Yoshiro Ootsu; Yaeno Arima
- Web page: https://patentgrep.com/patent/US4400295A

## CPC

- A61K 8/361: {Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof}
- A61K 8/06: Emulsions
- A61K 8/342: {Alcohols having more than seven atoms in an unbroken chain}
- A61K 8/345: {containing more than one hydroxy group}
- A61K 8/365: Hydroxycarboxylic acids; Ketocarboxylic acids
- A61K 8/375: {the alcohol moiety containing more than one hydroxy group}
- A61K 8/43: Guanidines
- A61K 8/44: Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K 8/553: {Phospholipids, e.g. lecithin}
- A61K 8/60: Sugars; Derivatives thereof
- A61K 8/63: Steroids; Derivatives thereof
- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61K 47/14: Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
- A61K 47/183: {Amino acids, e.g. glycine, EDTA or aspartame}
- A61K 47/24: containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
- A61K 47/28: Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
- A61Q 19/00: Preparations for care of the skin
- C09K 23/017: {Mixtures of compounds}
- A61K 2800/75: Anti-irritant
- A61Q 1/02: Preparations containing skin colorants, e.g. pigments (preparations in powder form A61Q1/12)
- A61Q 1/14: Preparations for removing make-up
- A61Q 17/00: Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q 19/10: Washing or bathing preparations
- Y10S 516/06: Protein or carboxylic compound containing
- Y10S 516/07: Organic amine, amide, or n-base containing
- Y10S 516/907: The agent contains organic compound containing phosphorus, e.g. lecithin
- Y10S 516/915: The compound contains -C[=O]NHH where substitution may be made for the hydrogen
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Emulsifier composition which comprises a condensation product of a fatty acid and a basic amino acid, and at least one secondary compound selected from the group consisting of a sterol compound, a fatty acid ester of polyhydric alcohol, a diol compound having hydroxyl groups at .alpha. and .beta. positions, a glycerophosphoric acid ester and a higher alcohol. Various creams and lotions can readily be prepared using the emulsifier composition.

## Claims

### Claim 1

A stable emulsifier composition which comprises an interfacial complex comprising the reaction product of (a) a condensation product of a fatty acid selected from the group consisting of stearic acid, oleic acid, and myristic acid, and a basic amino-acid selected from the group consisting of arginine, lysine, .beta.-lysine, and hydroxylsine, and (b) a secondary compound selected from the group consisting of a sterol compound, a fatty acid ester of a polyhydric alcohol, a diol compound having hydroxyl groups at the .alpha. and .beta. positions, a glycerophosphoric acid ester, a higher alcohol and mixtures thereof, said condensation products and said secondary compound being at a weight ratio ranging from 20:1 to 1:20, and said composition being non-irritating to the skin.

### Claim 2 (depends on 1)

The emulsifier composition according to claim 1, wherein the sterol compound is selected from the group consisting of cholesterol, cholestanol, phytosterols, phytostanol obtained by hydrogenation of phytosterol, ergosterol, brassicasterol, spinasterol, fucosterol, and sterol mixtures contained in unsaponifiable matter of lanolin, and mixtures thereof.

### Claim 3 (depends on 2)

The emulsifier composition according to claim 2, wherein the glycerophosphoric acid ester is a compound having the following formula ##STR2## wherein R.sub.1 and R.sub.2 are hydrogen, saturated hydrocarbon having 8 to 40 carbon atoms or unsaturated hydrocarbon having 8 to 40 carbon atoms respectively, and R.sub.3 is hydrogen, choline, ethanolamine, serine, inositol, glycerol, N-methylethanolamine or N,N-dimethylethanolamine.

### Claim 4 (depends on 3)

The emulsifier composition according to claim 3 wherein the glycerophosphoric acid ester is selected from the group consisting of phosphatidic acid, phosphatidyl choline, phosphatidyl ethanolamine, phosphatidyl serine, phosphatidyl-N-methylethanolamine, phosphatidyl-N,N-dimethylethanolamine, phosphatidyl glycerol, phosphatidyl inositol, lysophosphatidyl choline, and mixtures thereof.

### Claim 5 (depends on 2)

The emulsifier composition according to claim 2, wherein the higher alcohol is selected from the group consisting of straight chain saturated higher alcohols having 8 to 40 carbon atoms, branched chain saturated higher alcohols having 8 to 40 carbon atoms, straight chain unsaturated higher alcohols having 8 to 40 carbon atoms, branched chain unsaturated higher alcohols having 8 to 40 carbon atoms, and mixtures thereof.

### Claim 6 (depends on 5)

The emulsifier composition according to claim 5 wherein the higher alcohol is selected from the group consisting of lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, behenyl alcohol, beef tallow alcohol, sperm alcohol, oleyl alcohol, cetostearyl alcohol, isostearyl alcohol, 2-octyldodecanol, 2-hexyldecanol, octyl alcohol, decyl alcohol, arachidic alcohol, coconut alcohol, lanolin alcohol, isocetyl alcohol, octadecenol glycol, and mixtures thereof.

### Claim 7 (depends on 2)

The emulsifier composition according to claim 2, where the polyhydric alcohol used for production of the fatty acid ester of polyhydric alcohol is selected from the group consisting of glycerol, tetraglycerol, pentaglycerol, hexaglycerol, decaglycerol, pentaerythritol, sorbitan, sorbitol, mannitol, sucrose and mixtures thereof.

### Claim 8 (depends on 7)

The composition of claim 7 where the fatty acid used for production of the fatty acid ester of polyhydric alcohol is selected from the group consisting of straight-chain saturated fatty acids, branched chain saturated fatty acids, straight chain unsaturated fatty acids, branched chain unsaturated fatty acids, and mixtures thereof.

### Claim 9 (depends on 8)

The composition of claim 8 where the fatty acid used for production of the fatty acid ester of polyhydric alcohol is selected from the group consisting of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, linolenic acid, ricinoleic acid, isostearic acid, undecylenic acid, hydroxystearic acid, cerotic acid, abietic acid, isooctanoic acid, isohexadecanoic acid, 2-ethylhexadecanoic acid, lanolin fatty acid, 12-methyl-9,11-octadecadienoic acid and mixtures thereof.

### Claim 10 (depends on 2)

The composition according to claim 2 wherein the diol compound having groups at .alpha. and .beta. positions is selected from the group consisting of 1,2-long chain alkane diols having 10 to 40 carbon atoms, glycerol monoalkyl ethers having 8 to 40 carbon atoms, and mixtures thereof.

### Claim 11 (depends on 10)

The composition according to claim 10 where the 1,2-long chain alkane diols are selected from the group consisting of reaction products obtained by hydroxylation of .alpha.-olefinic compounds, straight chain iso-1,2-long chain alkane diols present in unsaponifiable matters of natural lanolin, straight chain antiiso-1,2-long chain alkane diols present in unsaponifiable matters of natural lanolin, and mixtures thereof.

### Claim 12 (depends on 10)

The composition according to claim 10 where the glycerol monoalkyl ethers are selected from the group consisting of glycerol monomyristyl ether obtained by reacting glycerol monosodium with myristyl sulfate, glycerol monolauryl ether obtained by reacting glycerol monosodium with lauryl sulfate, chimyl alcohol C.sub.16 H.sub.33 OCH.sub.2 CH(OH)CH.sub.2 OH, batyl alcohol C.sub.18 H.sub.37 OCH.sub.2 CH(OH)CH.sub.2 OH, celakyl alcohol C.sub.18 H.sub.35 OCH.sub.2 CH(OH)CH.sub.2 OH, and mixtures thereof.

### Claim 13

A method of preparing a stable emulsifier composition which comprises reacting a fatty acid selected from the group consisting of stearic acid, oleic acid and myristic acid, and a basic amino-acid selected from the group consisting of arginine, lysine, .beta.-lysine, and hydroxylysine, to form a condensation product, and reacting the condensation product with a secondary compound selected from the group consisting of a sterol compound, a fatty acid ester of a polyhydric alcohol, a diol compound having hydroxyl groups at the .alpha. and .beta. positions, a glycerophosphoric acid ester, a higher alcohol and mixtures thereof, said condensation product and said secondary compound being at a weight ratio ranging from 20:1 to 1:20, to form an interfacial complex, said emulsifier composition being non-irritating to the skin.