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GB1560428A - Cosmetic emulsion and the production thereof - Google Patents

Cosmetic emulsion and the production thereof Download PDF

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Publication number
GB1560428A
GB1560428A GB8983/77A GB898377A GB1560428A GB 1560428 A GB1560428 A GB 1560428A GB 8983/77 A GB8983/77 A GB 8983/77A GB 898377 A GB898377 A GB 898377A GB 1560428 A GB1560428 A GB 1560428A
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Prior art keywords
copolymer
cosmetic
emulsion
bis
dodecylacrylate
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GB8983/77A
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Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Priority claimed from DE19762608875 external-priority patent/DE2608875A1/en
Priority claimed from DE19762608834 external-priority patent/DE2608834A1/en
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of GB1560428A publication Critical patent/GB1560428A/en
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/06Emulsions
    • A61K8/064Water-in-oil emulsions, e.g. Water-in-silicone emulsions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Dermatology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Cosmetics (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Description

(54) COSMETIC EMULSIONS AND THE PRODUCTION THEREOF (71) We, HENKEL KOMMANDIT GESELLSCHAFT AUF AKTIEN, a German Company, of 67 Henkelstrasse, 4000 Duesseldorf-Holthausen, Federal Republic of Germany, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: The present invention relates to cosmetic emulsions of the water-in-oil type.
In contrast to the production of oil-in-water emulsions, only a limited number of emulsifying agents are available for producing cosmetic emulsions of the water-in-oil type and, moreover, the best of these emulsifying agents are becoming increasingly scarce. Even nowadays, lanolin and its derivatives are still some of the most important bases for emulsifying agents for producing creams of the water-inoil type. However, despite their uncontested advantages, lanolin, as well as its derivatives, has certain disadvantages. Thus, conventional water-in-oil emulsifying agents based on lanolin and its derivatives impart a strong characteristic odour to the creams prepared with these substances. This requires strong perfuming which frequently cannot be tolerated by persons having sensitive skin. However, this influencing of the quality of the cream by a strong characteristic odour is not only peculiar to lanolin and its derivatives, but also extends to lanolin-free water-in-oil emulsifying agents based on animal stearols, particularly such emulsifying agents based on cholesterol.
Furthermore, low-molecular weight emulsifying agents, together with the effective substances of the cream, can be absorbed by the skin, this not being desirable in all cases.
In addition to the said emulsifying agents based on wool wax alcohols and sterols the most widely known water-in-oil emulsifiers for cosmetic purposes include the oleic acid esters of various polyols such as glycerine, pentaerythritol, trimethylolpropane, and sorbitol. However, owing to the unsaturated character of their acid component, the oleic acid esters have various disadvantages with respect to their technical use, so that there is a genuine demand for suitable new water-in-oil emulsifying agents.
According to the present invention there is provided a cosmetic emulsion of the waterin-oil type comprising, as emulsifying agent, a quantity of 2 to 20 percent by weight, relative to the total emulsion, of a statistical copolymer of mean molecular weight from 2,000 to 100,000 and which is built up, in the molar ratio of (I) to (IIa) or (rib) of 2:1 to 20:1, from units of the general formula
in which X represents hydrogen or a methyl radical, R1 represents an alkyl radical having 6 to 24 carbon atoms, R2 represents the radicals -CH2-CH2-OH, cH2-CH(OH)-CH,, cH2-CH(OH)CH,OH or -CH,-CH,-O-CH,-CH,OH, tH2V and R, represents the radicals -NH-CH2OH, -NH-CH,-CH,OH or --N(CH,CH,OH),, and containing 20 to 75 percent by weight of water relative to the total emulsion, and at least one vegetable or animal fat, wax, fatty alcohol or hydrocarbon.
The copolymers of alkyl(methvl)acry!ates (I) and hydroxyallyl(meth)acrylates (IIa), usable as emulsifying agents in the cosmetic emulsions in accordance with the present invention, can be manufactured in a generally known manner in one processing step under the conventional conditions of radical polymerization. Polymerization can be effected in non-polar solvents such as benzene or in polar solvents such as methanol, methylethylketone or tetrahydrofuran, by means of peroxides such as dibenzoyl peroxide or lauroyl peroxide and azo compounds such as azobisisobutyronitrile acting as a catalyst.
Technical production is effected to best advantage in the forum of solution polymerization in solvents which only dissolve the monomers but do not dissolve the polymers (precipitation polymerization), especially since this results in satisfactorily precipitable polymers which are virtually free from monomers (J. Scheiber, Chemie and Technologie der künstlichen Harze, Volume I, page 362 ff.
(1961)). Monomeric starting compounds of the mono- or polyhydroxyalkyl(meth)acrylates (IIa) type are the esters of acrylic acid and methacrylic acid respectively with ethyleneglycol, 1,2 - propyleneglycol, glycerine or diethyleneglycol. Some of these monomers are commercially available, such as 2 - hydroxyethylacrylate, 2 - hydroxyethylmethacrylate, 2 - hydroxypropylacrylate, 2 hydroxypropylmethacrylate or products known in the literature, such as 2,3 - dihydroxypropylacrylate (C.
A 72, P 56 787r, US-Patent 3,488,327), 2,3dihydroxypropylmethacrylate (J. Appl. Polym.
Sci. 9, 3162/63).
In addition to the mono- or polyhydroxy alkylacrylates (IIa), monomeric starting compounds of the polymers which may be mentioned are, for example, hexylacrylate, octylacrylate, 2 - ethylhexylacrylate, nonylacrylate, decylacrylate, laurylacrylate, myristylacrylate, cetylacrylate, stearylacrylate, behenylacrylate, hexylmethacrylate, octylmethacrylate, nonylmethacrylate, decylmethacrylate, laurylmethacrylate, myristylmethacrylate, cetylmethacrylate, stearylmethacrylate, behenylmethacrylate. Particular importance is attached to monomers having 8 to 14 carbon atoms in the alkyl radical, such as octylacrylate, nonyl acrylate, decylacrylate, laurylacrylate, myristyl acrylate, octylmethacrylate, nonylmethacrylate, decylmethacrylate, laurylmethacrylate, my ristylmethacrylate.
In the copolymers usable in accordance with the present invention, the molar ratios of the monomers mono- or polyhydroxyalkyl(meth) acrylate aIa):alkyl(meth)acrylate (I) are 1: 2 to 1:20, preferably 1:2 to 1:8 in the co polymers having units of monohydroxyalkyl (meth)acrylates, and preferably 1:4 to 1:12 in the copolymers having units of polyhydroxy alkyl(meth)acrylates.
The copolymers of alkyl(meth)acrylates (I) and mono - (N) - hydroxyalkyl)- or bis - (N hydroxyalkyl)(meth)acrylamides (IIb), usable as emulsifying agents in the cosmetic emul sions in accordance with the present inven tion, can be manufactured in generally known manner in one procesing step under the con ventional conditions of radical polymerization.
Polymerization may be effected in non-polar solvents such as benzene or toluene or in polar solvents such as methanol, methylethyl ketone or tetrahydrofuran, by means of per oxides, such as dibenzoyl - peroxide or lauroyl peroxide, and azo compounds, such as azo bisisobutyronitrile, as a catalyst.
Technical production is effected to best advantage in the form of a solution polymerization in solvents which only dissolve the monomers but do not dissolve the polymers (precipitation polymerization), especially since this results in satisfactorily predpitatable polymers which are virtually free from monomers (J. Scheiber, Chemie und Technologie der kiinstlichen Harze, Volume I, page 362 ff. (1961)).
Some of the monomeric starting compounds of the mono- or bis - (N - hydroxyalkyl) (meth)acrylamides type (IIb) are commer cially available, such as N - hydroxymethyl acrylamide or products known in the litera ture such as N - hydroxymethyl - methacryl amide (C.A. 66, P 66 705 c), N - 2 - hydroxy ethylacrylamide (C.A. 66, P 29 497 r), N 2 - hydroxyethylmethacrylamide (C.A. 64, P 1970 g), bis - (N - 2 - hydroxyethyl)acryl amide (C.A. 66, P 29 497 r), bis - (N - 2 hydroxyethyl)methacrylamide (C.A. 56, P 1616 i).
In addiction to the mono- or bis - (N hydroxyallyl)(meth)acrylamides (IIb), monomeric starting compounds of the polymers which may be mentioned are, for example, hexylacrylate, octylacrylate, 2 - ethylhexyl- acrylate, nonoylacrylate, decylacrylate, lauryl acrylate, myristylacrylate, cetylacrylate, stearylacrylate, behenylacrylate, hexylmeth acrylate, octylmethacrylate, nonylmethacrylate, decyimethacrylate, laurylmethacrylate, myristylmethacrylate, cetylmethacrylate, stearylmeth acrylate, behenylmethacrylate. Particular im portance is attached to the acrylic- or methacrylic acid esters of fatty alcohols having 8 to 14 carbon atoms, such as octylacrylate, nonylacrylate, decylacrylate, laurylacrylate, myristylacrylate, octylmethacrylate, nonylmethacrylate, decylmethacrylate, laurylmethacrylate, myristylmethacrylate.
In the copolymers usable in accordance with the present invention the molar ratios of the monomers mono- bis - (N - hydroxyalkyl) (meth)acrylamide (IIb): alkyl(meth)acrylate (I) are 1:2 to 1:20, preferably 1:3 to 1:12.
The copolymers which are usable in accordance with the present invention have mean molecular weights of from 2000 to 100,000; those having mean molecular weights of from 2000 to 20,000 being particularly suitable in view of the ready processability and the nature of the emulsions obtained. These molecular weights can be adjusted in a known manner by the quantity of catalyst, the nature and quantity of the solvent, and by the addition of polymerization regulators.
The emulsions in accordance with the present invention are produced in a simple and known manner by dissolving the copolymers, acting as emulsifying agents, in the oily phase at an increased temperature of approximately 60 to 700C, subsequently adding the desired quantity to water heated to approximately 60 to 650C and cold-agitating the emulsion obtained. Further contents of thejoosmetic emulsion to be produced, such as skin moisture regulators, vegetable extracts of effective substances, vitamins, hormones, pigments, salts, perfume oil, UV filtering substances or dyes, are, advantageously, dissolved or distributed in the phase which absorbs these substances to best advantage. The quantity of emulsifying agent required is 2 to 20 percent by weight, preferably 5 to 10 percent by weight, relative to the total cosmetic emulsion. The quantity of water to be incorporated is from 20 to 75 per cent by weight relative to the total cosmetic emulsion.
The products conventionally used, such as animal and vegetable oils and fats, synthetic esters of fatty acids with aliphatic alcohols.
higher fatty alcohols, waxes, so-called mineral fats and oils such as paraffin oil, Vaseline (Registered Trade Mark), ceresine, silicon oils and silicon fats are suitable as the oily phase of the cosmetic emulsions in accordance with the present invention.
German Offenlegungsschrift 2,116,787 has already described the use of sequence polymers, which at the same time have at least one lipophilic sequence and one hydrophilic sequence, as water-in-oil emulsifying agents.
Each sequence should have the characteristics of the corresponding homopolymer. These sequence polymers are obtained by anionic polymerization which makes extreme demands on the purity of the substances used, and which requires work to be carried out at low temperatures under a protective gas and increased safety precautions when handling spontaneously combustible catalysts. In contrast to this, the emulsifying agents required for producing the emulsions in accordance with the present invention can be manufactured by the simplest method.
In accordance with German Offenlegungsschrift 1,745,216, copolymers comprising a monomer having a lipophilic chain and a monomer having a carboxylic acid anhydride function are proposed as emulsifying agents for water-in-oil emulsions. However, such products are sensitive to hydrolysis and, in order to avoid this disadvantage, a further processing step is required in addition to polymerization in order to convert them into a more stable form.
The emulsions in accordance with the present invention can, in general, also be used by persons having a sensitive skin. Since they do not have any appreciable characteristic odour, they do not require any heavy perfuming which, in turn, is advantageous with respect to compatibility and also reduces costs.
Furthermore, the emulsions in accordance with the present invention are distinguished by low acid sensitivity, thus permitting the incorporation of acid raw materials such as organic acids. A further very favourable property of the emulsions in accordance with the present invention is their high resistance to temperature which allows them to withstand a thermal stress of 50 C for a period of 6 weeks without any detrimental effect.
The present invention will now be further described by, but is not limited to, the following examples: Examples In the first instance, the production of the copolymers which are usable in the cosmetic emulsions in accordance with the present invention will be described.
2 - hydroxyethylacrylate(IIa) - dodecylacrylate (I) - copolymer (1:6) 11.6 g (0.1 mol) of 2 - hydroxyethylacrylate and 144 g (0.6 mol) of dodecylacrylate were dissolved in 360 g of methylethylketone.
3.1 g of dibenzoylperoxide were added as a catalyst to the solution obtained. The reaction mixture was maintained at a temperature of 800C for 5 hours under agitation. After the reaction had been completed, the solvent was distilled off and the reaction product was washed a few times with methanoL 148 g, that is 95% of theory, of 2 - hydroxyethylacrylate - dodecylacrylate copolymer 1:6 were obtained.
The other copolymers used in the Examples given hereinafter were manufactured in an analogous manner.
N - hydroxymethylacrylamide(IIb) - dodecyl acrylate(I) copolymer (1:6) 10.1 g (0.1 mol) of N - hydroxymethylacrylamide and 144 g !0.6 mol) of dodecylacrylate were dissolved in 360 g of methylethylketone. 3.1 g of dibenzoyl peroxide were added to the solution as a catalyst. The reaction mixture was agitated for 5 hours at a temperature of 800C. After the reaction had been completed, the solvent was distilled off and the reaction product was washed a few times with methanol. 147 g, that is 95% of theory, of N - hydroxymethylacrylamide dodecylacrylate copolymer (1:6) were obtained.
The other copolymers used in the Examples given hereinafter were produced in an analogous manner.
1 Cosmetic emulsion based on Vaseline A mixture of 10 g of 2 - hydroxyethylacrylate - dodecyl acrylate copolymer (1:6) 40 g of Vaseline were fused by heating to 65oC. 50 g of water, heated to 650C, were added to the melt, and the compound was allowed to cool under constant agitation. The emulsion can be readily produced by manual agitation. The cream obtained is stable for several months and did not exhibit any change even after 6 weeks at 500 C. This basic cream can be used to manufacture various skin creams by adding various effective substances and perfume oils.
The 2 - hydroxyethylacrylate - dedocylacrylate copolymer (1:6) may be replaced with equally satisfactory results by, for example, the following copolymers: 2 - hydroxyethylacrylate - cetyl acrylate copolymer (1:4) 2 - hydroxyethylacrylate - behenyl acrylate copolymer (1 2) 2 - hydroxyethylacrylate - octyl acrylate copolymer (1:12) 2 - hydroxyethylmethacrylate decylacrylate copolymer (1:6) 2 - hydroxyethylmethacrylate octylmethacrylate copolymer (1:8) 2 - hydroxypropylacrylate myristylacrylate copolymer (1:6) 2 - hydroxypropylacrylate stearylacrylate copolymer (1:4) 2 - hydroxypropylmethacrylate decylmethacrylate copolymer (1:8) 2 - hydroxypropylmethacrylate dodecylacrylate copolymer (1 4) 2,3 - dihydroxypropylacrylate hexylacrylate polymer (1:20) 2,3 - dihydroxypropylacrylate octylacrylate copolymer (1: 15) 2,3 - dihydroxypropylacrylate dodecylacrylate copolymer (1:12) 2,3 - dihydroxypropylmethacry late - nonylmethacrylate copoly mer (1: 8 2,3 - dihydroxypropylmethacry late - cetylmethacrylate copoly mer (1:6) 2. Cosmetic emulsion based on groundnut hard fat/oleic acid decylester A mixture of 4 g of 2 - hydroxylethylacrylate - dodecyl acrylate copolymer (1:6) 40 g of groundnut hard fatjoleic acid decyl ester mixture (90:10) 3 g of beeswax 3 g of glycerine monooleate were fused by heating to 700C. 50 g of water, heated to 650C, were added to the melt under constant agitation, and the compound was allowed to cool under further agitation.
A cream was obtained whose stability proper ties are largely similar to those of the cream of Example 1. Various skin creams can be built up on this basic cream by incorporating further active substances such as skin moisture regulators, vegetable extracts, and perfume oils.
The hydroxyethylacrylate - dodecylacrylate copolymer (1:6) can be replaced with equally good results by, for example, the following copolymers: 2 - hydroxyethylacrylate - stearyl- acrylate copolymer (1:2) 2 - hydroxyethylmethacrylate dodecylacrylate copolymer (1:4) 2 - hydroxyethylmethacrylate octylmethacrylate copolymer (1:8) 2 - hydroxypropylacrylate decylacrylate copolymer (1:10) 2 - hydroxypropylacrylate myristylacrylate copolymer (1:6) 2,3 - dihydroxypropylacrylate myristylmethacrylate copolymer (1:8) 2,3 - dihydroxypropylacrylate octylacrylate copolymer (1:12) 2,3 - dihydroxypropylacrylate cetylacrylate copolymer (1:4) 2,3 - dihydroxypropylmeth acrylate - cetylmethacrylate co polymer (1:6) 2,3 - dihydroxypropylmeth acrylate - hexylmethylacrylate copolymer (1:12) 3. Cosmetic emulsion based on Vaseline/oleic acid decylester A mixture of 7 g of 2 - hydroxyethylacrylate - dodecyl acrylate copolymer (1:6) 10 g of Vaseline 15 g of oleic acid decylester 3 g of beeswax 2 g of calcium stearate were fused by heating to 650C. 63 g of water heated to 650C were stirred into this mixture and agitation was continued until the emulsion had cooled. A cream was obtained whose stability properties are largely similar to those of the two above-mentioned creams Cosmetic creams can be built up on this basic cream by incorporating cosmetic active substances and perfume oils.
The 2 - hydroxyethylacrylate - dodecylacrylate copolymer (1: 6) acting as an emulsifying agent can be replaced with equally good results by the same quantity of 2 - hydroxyethylacrylate - octylacrylate copolymer (1:8), 2,3 - dihydroxypropylacrylate - octylacrylate copolymer (1:12) and other of the copolymers which have been mentioned.
4. Cosmetic emulsions based on groundnut hard fat A mixture of 6 g of 2 - hydroxyethylacrylate - dodecyl acrylate copolymer (1:6) 44 g of ground nut hard fat were fused by heating to 650C. 50 g of water, heated to 650C, were stirred into this mixture. After agitation until cold, a cream was obtained whose stability properties are largely similar to those of the above-mentioned creams. The cream can be used as a basic cream for various cosmetic preparations.
5. Cosmetic emulsion based on Vaseline A mixture of 10 g of N - hydroxymethylacrylamide dodecylacrylate copolymer (1:6) 40 g of Vaseline were fused by heating to 650C. 50 g of water, heated to 650C, were added to the melt, and the compound was allowed to cool under constant agitation. The emulsion can be readily produced by manual agitation. The cream obtained is stable for several months and did not exhibit any change even after 6 weeks at 500 C. This basic cream can be used to manufacture various skin creams by adding various effective substances and perfume oils.
The N - hydroxymethylacrylamide - dodecylacrylate copolymer (1:6) can be replaced with equally good results by, for example, the following copolymers: N - hydroxymethylacrylamide decyl acrylate copolymer (1:3) N - hydroxymethylacrylamide behenylacrylate copolymer (1:2) N - hydroxymethylacrylamide octylacrylate copolymer (1:12) N - hydroxymethylacrylamide hexylacrylate copolymer (1:15) N - hydroxymethylacrylamide cetylacrylate copolymer (1:8) N - hydroxymethylmethacryl amide - decylacrylate copolymer (1:10) N - hydroxymethylmethacryl amide - ocetylmethacrylate co polymer (1: 8) N - 2 - hydroxyethylacrylamide dodecylmethacrylate copolymer (1:6) N - 2 - hydroxyethylacrylamide myristylacrylate copolymer (1:4) N - 2 - hydroxyethylmethacryl amide - stearylacrylate copolymer (1: 2) amide - decylmethacrylate co polymer (1:8) bis - (N - 2 - hydroxyethyl)acryl amide - hexylacrylate copolymer (1:20) bis (N - 2 - hydroxyethyl)octyl acrylate copolymer (1:12) bis - (N - 2 - hydroxyethyl)dodecyl methacrylate copolymer (1: 8) bis - (N - 2 - hydroxyethyl) methacrylamide - myristylacry late copolymer (1:6) bis - (N - 2 - hydroxyethyl) methacrylamide - nonylmeth acrylate copolymer (1:10) 6. Cosmetic emulsion based on groundnut hard fat/oleic acid decylester A mixture of 4 g of N - hydroxymethylacrylamide dodecyl acrylate copolymer (1:6) 40 g of groundnut hard fat/oleic acid decylester mixture 90:10 3 g of beeswax 3 g of glycerine monooletate were fused by heating to 700C. 50 g of water, heated to 650C, were added to the melt under constant agitation, and the compound was allowed to cool under further agitation. A cream was obtained whose stability characteristics are largely similar to those of the cream of Example 1. Various skin creams can be built up on this basic cream by in corporating further effective substances such as skin moisture regulators, vegetable extracts and perfume oils.
The N - hydroxymethylacrylamide decylacrylate copolymer (1:6) can be replaced with equally good results by, for example, the following copolymers: N - hydroxymethylacrylamide cetyl acrylate copolymer (1:4) N - 2 - hydroxyethylacrylamide dodecylacrylate copolymer (1: 8) N - 2 - hydroxyethylacrylamide octylmethacrylate copolymer (1:10) N - hydroxymethylmethacryl amide - stearylacrylate copoly mer (1:3) N - 2 - hydroxyethylmethacryl amide - octylacrylate copoly mer (1:8) N - 2 - hydroxyethylmethacryl amide - myristylacrylate copoly mer (1:6) bis - (N - 2 - hydroxyethyl) acrylamide- octylmethacrylate copolymer (1:12) bis - (N - 2 - hydroxyethyl) acrylamide - dodecylacrylate copolymer (1: 8) bis - (N - 2 - hydroxyethyl) methacrylate - decylacrylate copolymer (1:10) bis - (N - 2 - hydroxyethyl) methacrylate - decylacrylate copolymer (1 :4) 7. Cosmetic emulsion based on Vaseline/oleic acid decylester A mixture of 7 g of N - hydroxymethylacrylamide dodecylacrylate copolymer (1:6) 10 g of Vaseline 15 g of oleic acid decylester 3 gof bees-wax 2 g of calcium stearate were fused by heating to 650C. 63 g of water, heated to 650C, were stirred into this mixture and agitation was continued until the emulsion had cooled. A cream was obtained whose stability properties are largely similar to those of the two above-mentioned creams.
A large number of cosmetic creams can be built up on this basic cream by incorporating cosmetic effective substances and perfume oils.
The N - hydroxymethylacrylamide - dodecylacrylate copolymer (1:6) acting as an emulsifying agent can be replaced with equally good results by the same quantity of N - 2 hydroxyethylacrylamide - octylmethacrylate copolymer (1:10), bis (N - 2 - hydroxyethyl)- acrylamide - octylacrylate copolymer (1: 12) and others of the said copolymers.
8. Cosmetic emulsion based on groundnut hard fat A mixture of 6 g of N - hydroxymethylacrylamide dodecylacrylate copolymer (1:6) 44 g of groundnut hard fat were fused by heating to 650C. 50 g of water, heated to 650C, were stirred into this mixture. After agitating until cold, a cream was obtained whose stability properties are largely similar to the above-mentioned creams.
The cream can act as a basic cream for various cosmetic preparations.
It is readily possible to exchange the N hydroxymethylacrylamide - dodecylacrylate copolymer (1:6), acting as an emulsifying agent, for others of the above-mentioned copolymers.
WHAT WE CLAIM IS: 1. A cosmetic emulsion of the water-in-oil type, which comprises, as emulsifying agent, 2 to 20 percent by weight, relative to the total emulsion, of a statistical copolymer having a mean molecular weight of from 2,000 to 100,000 and which is built up, in the molar ratio of (I) to (II) of 2:1 to 20:1, from units of the general formulae
in which X represents hydrogen or a methyl radical, R1 represents an alkyl radical having 6 to 24 carbon atoms, R2 represents the radicals -CH2-CH2-OH, -CH2-CH(OH)-CH,, CH2CH(OH)CH20H or -CH,-CH,-O-CH2-CH20H, and R, represents the radicals -NH-CH2OH, --NHH-CHH,-CH,OH or --N(CH,CH-OH),, and contains 20 to 75 percent by weight of
**WARNING** end of DESC field may overlap start of CLMS **.

Claims (1)

  1. **WARNING** start of CLMS field may overlap end of DESC **.
    N - hydroxymethylmethacryl amide - stearylacrylate copoly mer (1:3) N - 2 - hydroxyethylmethacryl amide - octylacrylate copoly mer (1:8) N - 2 - hydroxyethylmethacryl amide - myristylacrylate copoly mer (1:6) bis - (N - 2 - hydroxyethyl) acrylamide- octylmethacrylate copolymer (1:12) bis - (N - 2 - hydroxyethyl) acrylamide - dodecylacrylate copolymer (1: 8) bis - (N - 2 - hydroxyethyl) methacrylate - decylacrylate copolymer (1:10) bis - (N - 2 - hydroxyethyl) methacrylate - decylacrylate copolymer (1 :4) 7. Cosmetic emulsion based on Vaseline/oleic acid decylester A mixture of
    7 g of N - hydroxymethylacrylamide dodecylacrylate copolymer (1:6)
    10 g of Vaseline
    15 g of oleic acid decylester
    3 gof bees-wax
    2 g of calcium stearate were fused by heating to 650C. 63 g of water, heated to 650C, were stirred into this mixture and agitation was continued until the emulsion had cooled. A cream was obtained whose stability properties are largely similar to those of the two above-mentioned creams.
    A large number of cosmetic creams can be built up on this basic cream by incorporating cosmetic effective substances and perfume oils.
    The N - hydroxymethylacrylamide - dodecylacrylate copolymer (1:6) acting as an emulsifying agent can be replaced with equally good results by the same quantity of N - 2 hydroxyethylacrylamide - octylmethacrylate copolymer (1:10), bis (N - 2 - hydroxyethyl)- acrylamide - octylacrylate copolymer (1: 12) and others of the said copolymers.
    8. Cosmetic emulsion based on groundnut hard fat A mixture of
    6 g of N - hydroxymethylacrylamide dodecylacrylate copolymer (1:6)
    44 g of groundnut hard fat were fused by heating to 650C. 50 g of water, heated to 650C, were stirred into this mixture. After agitating until cold, a cream was obtained whose stability properties are largely similar to the above-mentioned creams.
    The cream can act as a basic cream for various cosmetic preparations.
    It is readily possible to exchange the N hydroxymethylacrylamide - dodecylacrylate copolymer (1:6), acting as an emulsifying agent, for others of the above-mentioned copolymers.
    WHAT WE CLAIM IS: 1. A cosmetic emulsion of the water-in-oil type, which comprises, as emulsifying agent, 2 to 20 percent by weight, relative to the total emulsion, of a statistical copolymer having a mean molecular weight of from 2,000 to 100,000 and which is built up, in the molar ratio of (I) to (II) of 2:1 to 20:1, from units of the general formulae
    in which X represents hydrogen or a methyl radical, R1 represents an alkyl radical having 6 to 24 carbon atoms, R2 represents the radicals -CH2-CH2-OH, -CH2-CH(OH)-CH,, CH2CH(OH)CH20H or -CH,-CH,-O-CH2-CH20H, and R, represents the radicals -NH-CH2OH, --NHH-CHH,-CH,OH or --N(CH,CH-OH),, and contains 20 to 75 percent by weight of
    water relative to the total emulsion, and at least one vegetable or animal fat, wax fatty alcohol or hydrocarbon.
    2. A cosmetic emulsion as claimed in Claim 1, in which the alkyl radical Rl has a chain length of 8 to 14 carbon atoms.
    3. A cosmetic emulsion as claimed in Claim 1 or Claim 2, in which the molar ratio of the monomers monohydroxyalkyl(meth)acrylate (IIa):alkyl(methBacrylate (I) is 1:2 to 1:8.
    4. A cosmetic emulsion as claimed in Claim 1 or Claim 2, in which the molar ratio of the monomers polyhydroxyalkyl(meth)acrylate (IIa): alkyl(meth)acrylate (I) is 1:4 to 1:12.
    5. A cosmetic emulsion as claimed in Claim 1 or Claim 2, in which the molar ratio of the monomers mono- or bis - (N - hydroxyalkyl)(meth)acrylamide (IIb): alkyl(meth)acryl- ate (I) is 1:3 to 1:12.
    6. A cosmetic emulsion as claimed in any of Claims 1 to 5, in which the copolymer, used as emulsifying agent, has a mean molecular weight of 3000 to 20,000.
    7. A cosmetic emulsion as claimed in any of Claims 1 to 6, in which the copolymer is present in an amount from 5 to 10 percent by weight relative to the total emulsion.
    8. A cosmetic emulsion as claimed in Claim 1 and substantially as hereinbefore described with reference to any of the Examples.
GB8983/77A 1976-03-04 1977-03-03 Cosmetic emulsion and the production thereof Expired GB1560428A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19762608875 DE2608875A1 (en) 1976-03-04 1976-03-04 WATER-IN-OIL TYPE COSMETIC EMULSIONS AND THEIR PRODUCTION
DE19762608834 DE2608834A1 (en) 1976-03-04 1976-03-04 WATER-IN-OIL TYPE COSMETIC EMULSIONS AND THEIR PREPARATION

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GB1560428A true GB1560428A (en) 1980-02-06

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JP (1) JPS52108030A (en)
AT (1) AT345984B (en)
BR (1) BR7701296A (en)
FR (1) FR2342784A1 (en)
GB (1) GB1560428A (en)
IT (1) IT1075300B (en)
NL (1) NL7701484A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2123290A (en) * 1982-06-17 1984-02-01 Oreal Composition based on cationic polymers anionic polymers and waxes intended for use in cosmetics
US11510860B2 (en) 2017-11-15 2022-11-29 L'oreal Composition comprising a UV-screening agent, an acrylic polymer and a fatty acid ester of dextrin
US11839668B2 (en) 2017-11-15 2023-12-12 L'oreal Composition comprising photonic particles, a UV-screening agent and an acrylic polymer

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6591777B2 (en) * 2014-05-28 2019-10-16 三洋化成工業株式会社 Cosmetics having a copolymer
FR3073408B1 (en) * 2017-11-15 2019-10-11 L'oreal COMPOSITIONS COMPRISING AT LEAST ONE ACRYLIC POLYMER AND AT LEAST ONE INSOLUBLE ORGANIC FILTER
FR3073410B1 (en) * 2017-11-15 2019-10-11 L'oreal EMULSION COMPRISING ANIONIC ACRYLIC COPOLYMER AND LIPOPHILIC POLYMER
FR3073411B1 (en) * 2017-11-15 2024-08-02 Oreal COMPOSITION COMPRISING A FATTY PHASE, A LIPOPHILIC POLYMER AND A VOLATILE HYDROCARBON OIL

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2123290A (en) * 1982-06-17 1984-02-01 Oreal Composition based on cationic polymers anionic polymers and waxes intended for use in cosmetics
US4871536A (en) * 1982-06-17 1989-10-03 L'oreal Composition based on cationic polymers, anionic polymers and waxes for use in cosmetics
US11510860B2 (en) 2017-11-15 2022-11-29 L'oreal Composition comprising a UV-screening agent, an acrylic polymer and a fatty acid ester of dextrin
US11839668B2 (en) 2017-11-15 2023-12-12 L'oreal Composition comprising photonic particles, a UV-screening agent and an acrylic polymer

Also Published As

Publication number Publication date
NL7701484A (en) 1977-09-06
JPS52108030A (en) 1977-09-10
IT1075300B (en) 1985-04-22
AT345984B (en) 1978-10-10
FR2342784A1 (en) 1977-09-30
FR2342784B1 (en) 1978-10-20
BR7701296A (en) 1978-01-03
ATA141677A (en) 1978-02-15

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