CN113081899A - Cosmetic composition and application thereof - Google Patents

Cosmetic composition and application thereof Download PDF

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CN113081899A
CN113081899A CN202110418929.6A CN202110418929A CN113081899A CN 113081899 A CN113081899 A CN 113081899A CN 202110418929 A CN202110418929 A CN 202110418929A CN 113081899 A CN113081899 A CN 113081899A
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cosmetic composition
polyurethane
monomer
alkyl
amphoteric
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CN113081899B (en
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肖蓉
熊晓辉
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Shanghai Bairuimei Brand Management Co ltd
Zhuhai Yatuo Biotechnology Co ltd
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Shanghai Yijin Brand Management Co ltd
Zhuhai Yatuo Biotechnology Co ltd
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/87—Polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions 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
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions 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
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions 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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers

Abstract

The invention relates to the technical field of cosmetics, and discloses a cosmetic composition which comprises at least one polyurethane and at least one amphoteric copolymer; polyurethanes are obtained by reacting at least one water-insoluble, non-water-dispersible isocyanate-functional polyurethane prepolymer, at least one amino-functional compound and an alkyl tin compound; the monomer which participates in copolymerization to obtain the amphoteric copolymer comprises an acrylic group-containing monomer and an amphoteric monomer, wherein the acrylic group-containing monomer is at least one selected from acrylic acid, methacrylic acid, alkyl acrylate and alkyl methacrylate; the amphoteric monomer is an amphoteric monomer selected from at least one of methacryl alkyl betaine and methacryl alkyl amine oxide. The cosmetic composition has good face fixing effect.

Description

Cosmetic composition and application thereof
Technical Field
The invention relates to the technical field of cosmetics, in particular to a cosmetic composition and application thereof.
Background
The epidermis of both humans and animals belongs to the stratum corneum protein. The composition for fixing the skin is one of cosmetic compositions, and can be used for fixing the skin and stabilizing different makeup. The skin make-up composition is primarily in the form of a make-up spray or a make-up lotion. The makeup mist and the makeup water have little difference in their compositions, but are different in their applications. A makeup spray is applied to the moist skin as an aid to model the makeup. In contrast, a make-up spray is sprayed onto dry, already patterned skin to secure the makeup. In addition to the make-up spray or make-up lotion, there are also forms of skin make-up gels.
For a makeup spray or makeup water, the fixing or shaping composition for the makeup is usually in the form of a formulation which can be sprayed from an aerosol container, squeezed from a squeeze bottle or applied by means of a pump, sprayer or foaming device. It consists of alcoholic or hydro-alcoholic solution of film-forming natural or synthetic polymers. These polymers can be chosen from nonionic, cationic, amphoteric or anionic polymers. For skin make-up gels, the formulations described above are adjusted to acceptable viscosities by using conventional thickeners.
The film-forming polymers used in the prior art are preferably anionic or amphoteric polymers based on acrylates. If the content of volatile organic solvents or propellants in the skin makeup remover formulation is small, the use of a common acrylate causes stability problems such as sedimentation, separation, and the like. Furthermore, typical film-forming polymers exhibit low film-forming properties and/or film-forming properties when the skin is in contact with rain or sweat, and/or under the influence of high atmospheric humidity.
In view of this, the invention is particularly proposed.
Disclosure of Invention
The object of the present invention is to provide a cosmetic composition and its use, which aim to ameliorate at least one of the problems mentioned in the background.
The invention is realized by the following steps:
a cosmetic composition comprising: at least one polyurethane and at least one ampholytic copolymer;
polyurethanes are obtained by reacting at least one water-insoluble, non-water-dispersible isocyanate-functional polyurethane prepolymer, at least one amino-functional compound and an alkyl tin compound;
the monomer which participates in copolymerization to obtain the amphoteric copolymer comprises an acrylic group-containing monomer and an amphoteric monomer, wherein the acrylic group-containing monomer is at least one selected from acrylic acid, methacrylic acid, alkyl acrylate and alkyl methacrylate; the method comprises the following steps of; the amphoteric monomer is at least one selected from methacryl alkyl betaine and methacryl alkyl amine oxide;
the structural formula of the methacrylalkyl betaine is as follows:
Figure BDA0003027131180000021
the structural formula of the methacrylalkylamine oxide is as follows:
Figure BDA0003027131180000022
in the above two formulae, R1Optionally H or CH3，R2And R3Each independently a straight or branched chain C1-C10Alkyl, and n represents an integer of 1 to 20.
In an alternative embodiment, the monomers that participate in the copolymerization to give the amphoteric copolymer further include pyrrolidone monomers.
In an alternative embodiment, the acrylic group-containing monomer includes a first monomer and a second monomer, the first monomer being selected from at least one of acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, isopropyl acrylate, and isopropyl methacrylate; the second monomer is at least one of octadecyl acrylate and octadecyl methacrylate;
in an alternative embodiment, the acrylic group-containing monomer further comprises a third monomer selected from at least one of lauryl acrylate and lauryl methacrylate.
In an alternative embodiment, in the methacrylalkylamine oxide formula, R1、R2And R3Are all CH3And n is 2.
In alternative embodiments, the amino-functional compound is selected from at least one of primary amines, secondary amines, and diamines;
in an alternative embodiment, the amino-functional compound is selected from at least one of diamines.
In an alternative embodiment of the method of the present invention,
in an alternative embodiment, the prepolymer is obtained by reacting at least one of a polyether polyol, a polycarbonate polyol, a polyether polycarbonate polyol and a polyester polyol with at least one polyisocyanate;
in an alternative embodiment, the polyisocyanate includes at least one of hexamethylene diisocyanate and isophorone diisocyanate.
In an optional embodiment, the polyurethane accounts for 0.1-20% of the cosmetic composition by mass;
in an optional embodiment, the weight ratio of the amphoteric copolymer in the cosmetic composition is 0.1-20%;
in an alternative embodiment, the total mass of polyurethane and ampholyte copolymer is 0.1% to 30% of the total mass of the cosmetic composition;
in an alternative embodiment, the weight ratio of the polyurethane to the amphoteric copolymer is 1-30: 1-30; more preferably, the ratio of the two is 1-10: 1-10; further preferably, the ratio of the two is 3-5: 1.
In an alternative embodiment, at least one of a polyol, a surfactant, a preservative, a fragrance, a humectant, and an active is also included.
The application of the cosmetic composition provided by the embodiment of the application in skin makeup fixation.
The invention has the following beneficial effects:
the polyurethane and the amphoteric copolymer are mutually interwoven to form a net structure, and respective groups have good acting force on grease, powder, pigment, emulsifier and the like, so that the polyurethane and the amphoteric copolymer can be fixedly adsorbed on the surface of the net. When the cosmetic composition provided by the application is applied to skin, a hard film with certain softness and elasticity can be formed, the makeup fixing capacity of the cosmetic composition is durable due to the interaction of polyurethane and the amphoteric copolymer, and the cosmetic composition has excellent film-forming property and the makeup maintaining property under normal environment. In addition, the shampoo has excellent washing-off property.
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In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the embodiments will be briefly described below, it should be understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and for those skilled in the art, other related drawings can be obtained according to the drawings without inventive efforts.
FIG. 1 is a statistical chart generated from the data of Table 1.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The cosmetic composition and its use provided by the present invention are specifically described below.
A cosmetic composition comprising: at least one polyurethane and at least one ampholytic copolymer;
the polyurethane is obtained by reacting at least one water-insoluble, non-water-dispersible isocyanate-functional polyurethane prepolymer, at least one amino-functional compound, and an alkyl tin compound;
the monomers participating in the copolymerization to obtain the amphoteric copolymer comprise acrylic group-containing monomers and amphoteric monomers, wherein the acrylic group-containing monomers are selected from at least one of acrylic acid, methacrylic acid, alkyl acrylate and alkyl methacrylate; the amphoteric monomer is at least one selected from methacryl alkyl betaine and methacryl alkyl amine oxide;
the structural formula of the methacryl alkyl betaine is as follows:
Figure BDA0003027131180000051
the structural formula of the methacrylalkylamine oxide is as follows:
Figure BDA0003027131180000052
in the above two formulae, R1Optionally H or CH3，R2And R3Each independently a straight or branched chain C1-C10Alkyl, and n represents an integer of 1 to 20.
In the context of the present invention, the term "water-insoluble, water-non-dispersible polyurethane prepolymer" means that the solubility of the prepolymer in water at 23 ℃ is less than 10 g/l, preferably less than 5 g/l, and that the prepolymer does not give rise to sedimentation-stable dispersions in water (in particular deionized water) at 23 ℃. In other words, in any experiment in which it was dispersed in water, the prepolymer precipitated out. Water here refers to deionized water without added surfactant.
In some embodiments, it is preferred that the polyurethane prepolymers used in the present invention have terminal isocyanate groups, i.e., the isocyanate groups are at the chain ends of the prepolymer. Further preferably, all chain ends of the prepolymer have an isocyanate group.
Further, the polyurethane prepolymer used in the present invention preferably has substantially neither an ionic group nor an ionogenic group, that is, the content of the ionic group and the ionogenic group is suitably less than 15 milliequivalents (Mil1iequivalent)/100g of the polyurethane prepolymer, preferably less than 5 milliequivalents, further preferably less than 1 milliequivalents, particularly preferably less than 0.1 milliequivalents/l 00g of the polyurethane prepolymer.
In some embodiments, preferably, the amino-functional compound is selected from at least one of primary amines, secondary amines, and diamines; further preferably, the amino-functional compound is selected from at least one of diamines.
In some embodiments, it is preferable that the alkyl tin compound has a primary structure having a mono-substituent, a di-substituent, a tri-substituent and a tetra-substituent (referring to the number of R). The structural general formula of the compound is RnSnX4-n, and R is alkyl. The total is methyl, ethyl, propyl, butyl and octyl. When n is 1-4, there are one, two, three and four alkyl tin compounds. X can be oxygen, sulfur, chlorine, bromine, iodine and organic acids.
The present invention provides cosmetic compositions, especially aqueous (i.e. water-based) compositions, wherein the polyurethane is present in dispersed form, i.e. substantially in non-dissolved form. Water generally constitutes the major constituent of the dispersion medium, in addition to other liquid media such as solvents that may be present, and is greater than 50% by weight based on the total amount of liquid dispersion medium in the cosmetic composition.
In some embodiments, preferably, the cosmetic composition of the present invention preferably has a Volatile Organic Compound (VOC) content of less than 80 wt%, more preferably less than 55 wt%, even more preferably less than 40 wt%, based on the cosmetic composition.
In some embodiments, it is further preferred that the aqueous polyurethane dispersion used to prepare the cosmetic composition has a Volatile Organic Compound (VOC) content of less than 10 wt%, preferably less than 3 wt%, more preferably less than 1 wt%, based on the aqueous polyurethane dispersion.
The acid number of the prepolymer is suitably below 30mg KOH/g, preferably below 10mg KOH/g, in respect of the acidic ionic groups and/or ionogenic groups. The acid number represents the mass (mg) of potassium hydroxide required to neutralize 1g of the investigated sample (measured according to DIN EN ISO 211). The neutralized acid (i.e., the corresponding salt) naturally has no acid value or has a reduced acid value. Lower acid numbers ensure film hardness within the appropriate range.
In some embodiments, preferably, the prepolymer used in the preparation of the polyurethane is obtained by reacting at least one of a polyether polyol, a polycarbonate polyol, a polyether polycarbonate polyol, and a polyester polyol with at least one polyisocyanate.
In some embodiments, more preferably, each of the above-described polymer polyols has a number average molecular weight of preferably about 400-6000g/mol (as determined by gel permeation chromatography in tetrahydrofuran at 23 ℃ C. relative to polystyrene standards here and for the molecular weight data below). Their use in the preparation of polyurethanes or polyurethane prepolymers will, as a result of reaction with polyisocyanates, lead to the formation of corresponding polyether and/or polycarbonate and/or polyether-polycarbonate segments or polyester segments in the polyurethanes having the corresponding molecular weights of these segments. Further preferably, the various polymer polyols described above are polymer polyols having a linear structure.
In some embodiments, it is still further preferred that the polyurethane is preferably a substantially linear molecule. Of course, in other embodiments, it may be branched.
In some embodiments, the number average molecular weight of the polyurethane used is about 1000-.
In some preferred embodiments herein, the polyurethane is added to the cosmetic composition, especially in the form of an aqueous dispersion.
The polyurethanes or polyurethane dispersions used in the examples herein may be obtained by methods known in the art using known components, such as, for example, U.S. patent publication No. US 2011/0027211, which is incorporated herein by reference in its entirety; this application is based on this publication and is otherwise identical except that the amine having an ionic group or an ionogenic group is replaced with an alkyltin compound. The corresponding steps are briefly described as follows:
a) preparation of an isocyanate-functional polyurethane prepolymer formed from
An organic polyisocyanate, wherein the polyisocyanate is selected from the group consisting of,
the polymer polyols preferably have a number average molecular weight of 400-8000g/mol (determined here and for the following molecular weight data by gel permeation chromatography in tetrahydrofuran at 23 ℃ relative to polystyrene standards), more preferably 400-6000g/mol and particularly preferably 600-3000g/mol, and an OH functionality of preferably 1.5 to 6, more preferably 1.8 to 3, particularly preferably 1.9 to 2.1, optionally hydroxy-functional compounds having a molecular weight of preferably 62 to 399g/mol, and optionally nonionic hydrophilicizing agents.
b) Some or all of their free NCO groups are then reacted with one or more amino-functional compounds A2), such as primary and/or secondary amines and/or diamines, and also with alkyltin compounds. The polyurethane used according to the invention is preferably dispersed in water before, during or after step b).
The reaction with the diamine or two or more diamines in step b) is particularly preferably carried out with chain extension. In this regard, monofunctional amines can additionally be added as chain terminators to control molecular weight.
The alkyl tin compound has a basic structure of mono-, di-, tri-and tetra-substituted (referring to the number of R) ═ by.
These alkyltin compounds are incorporated into the polyurethane A) via the A2 component reacted in step b). The polyurethanes of the invention optionally additionally have nonionic components for hydrophilization. Particularly preferred are groups in the polyurethane to achieve hydrophilization.
In order to achieve good sedimentation stability, the number-average particle size of the polyurethane dispersions of the invention is preferably below 750nm, particularly preferably below 500nm, as determined by laser correlation spectroscopy after dilution with deionized water (instrument: Malvern Zetasizer 1000, Malverer Inst.Limited).
Suitable organic polyisocyanates are the aliphatic, aromatic or cycloaliphatic polyisocyanates known to the person skilled in the art having an NCO functionality of greater than or equal to 2.
Non-limiting examples of such polyisocyanates are 1, 4-butylidene diisocyanate, 1, 6-Hexamethylene Diisocyanate (HDI), isophorone diisocyanate (IPDI), 2,2, 4-and/or 2,4, 4-trimethylhexamethylene diisocyanate, the bis (4, 4' -isocyanatocyclohexyl) methane isomer or mixtures of these isomers, 1, 4-cyclohexylidene diisocyanate, 4-isocyanatomethyl-1, 8-octane diisocyanate (nonane triisocyanate), 1, 4-phenylene diisocyanate, 2, 4-and/or 2, 6-toluene diisocyanate, 1, 5-naphthylidene diisocyanate, 2,2' -and/or 2,4' -and/or 4,4' -diphenylmethane diisocyanate, 1, 3-and/or 1, 4-bis (2-isocyanatoprop-2-yl) benzene (TMXDI), 1, 3-bis (isocyanatomethyl) benzene (XDI), and alkyl 2, 6-diisocyanatohexanoate (lysine diisocyanate) having a C1-C8-alkyl group.
In addition to the polyisocyanates mentioned above, it is also possible to use modified diisocyanates having a functionality of 2 or more with the structure uretdione, isocyanurate, urethane, allophanate, biuret, iminooxadiazinedione or oxadiazinetrione, and also mixtures of these components in proportions.
Hexamethylene diisocyanate, isophorone diisocyanate and mixtures of the foregoing diisocyanates are particularly preferred.
The polymer polyols have number-average molecular weights Mn in the range preferably from 400-8000g/mol, more preferably from 400-6000g/mol and particularly preferably from 600-3000g/mol, and preferably have OH functionalities of from 1.5 to 6, particularly preferably from 1.8 to 3 and very particularly preferably from 1.9 to 2.1.
The term "polymer" polyol here means, inter alia, that the polyol has at least two, more preferably at least three, repeating units linked together.
Such polymer polyols are the polyester polyols, polyacrylate polyols, polyurethane polyols, polycarbonate polyols, polyether polyols, polyester polyacrylate polyols, polyurethane polyester polyols, polyurethane polyether polyols, polyurethane polycarbonate polyols and polyester polycarbonate polyols known in polyurethane coating technology. They can be used alone or in a mixture in the preparation of the polyurethanes of the invention.
The polymer polyol in the present invention is preferably polytetramethylene glycol polyether, polycarbonate polyol and a mixture thereof, and polytetramethylene glycol polyether is particularly preferred.
The hydroxy-functional compound having a molecular weight of 62 to 399mol/g may be a non-polymeric polyol having up to 20 carbon atoms, such as ethylene glycol, diethylene glycol, triethylene glycol, 1, 2-propanediol, 1, 3-propanediol, 1, 4-butanediol, 1, 3-butanediol, cyclohexanediol, 1, 4-cyclohexanedimethanol, 1, 6-hexanediol, neopentyl glycol, hydroquinone dihydroxyethyl ether, bisphenol A (2, 2-bis (4-hydroxyphenyl) propane), hydrogenated bisphenol A (2, 2-bis (4-hydroxycyclohexyl) propane), trimethylolpropane, trimethylolethane, glycerol, pentaerythritol, and any mixture thereof.
Also suitable are ester diols having the stated molecular weight range, such as α -hydroxybutyl epsilon-hydroxycaproate, ω -hydroxyhexyl gamma-hydroxybutyrate, β -hydroxyethyl adipate or bis (β -hydroxyethyl) terephthalate.
In addition, monofunctional isocyanate-reactive hydroxyl group-containing compounds having the molecular weight range described above can also be used. Examples of such monofunctional compounds are ethanol, n-butanol, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, dipropylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monobutyl ether, tripropylene glycol monobutyl ether, 2-ethylhexanol, 1-octanol, 1-dodecanol, 1-hexadecanol.
Suitable nonionically hydrophilizing agents are, for example, polyoxyalkylene ethers having isocyanate-reactive groups, such as hydroxyl, amino or thiol groups. Preference is given to monohydroxy-functionalized polyoxyalkylene polyether alcohols having (on a statistical average) from 5 to 70, preferably from 7 to 55, ethylene oxide units per molecule, which polyoxyalkylene polyether alcohols are obtainable by alkoxylation of suitable starter molecules in a manner known per se (for example in the case of
Figure BDA0003027131180000091
der technischen Chemie,4th edition, Volume 19, VerlaggChemie, Weinheim pp.31-38). The abovementioned nonionically hydrophilicizing agents are pure polyoxyethylene ethers or mixed polyoxyalkylene ethers, where they contain at least 30 mol%, preferably at least 40 mol%, of ethylene oxide units, based on the total alkylene oxide units present.
Component A2) is preferably selected from primary or secondary amines and/or diamines. It comprises especially diamines.
Component a2), alkyltin compounds may be used. The basic structure thereof has mono-, di-, tri-and tetra-substituents (referring to the number of R) (the following component A2-II)). Preference is given to reacting a mixture of component A2-I) and component A2-II).
For example, organic diamines or polyamines, such as 1, 2-ethylenediamine, 1, 2-and 1, 3-diaminopropane, 1, 4-diaminobutane, 1, 6-diaminohexane, isophoronediamine, isomer mixtures of 2,2, 4-and 2,4, 4-trimethylhexamethylenediamine, 2-methylpentamethylenediamine, diethylenetriamine, 4, 4-diaminodicyclohexylmethane, hydrazine hydrate, and/or dimethylethylenediamine can be used as component A2-I).
Furthermore, compounds which have secondary amino groups in addition to primary amino groups or OH groups in addition to amino groups (primary or secondary) can also be used as component A2-I). Examples thereof are primary/secondary amines, such as diethanolamine, 3-amino-1-methylaminopropane, 3-amino-1-ethylaminopropane, 3-amino-1-cyclohexylaminopropane, 3-amino-1-methylaminobutane, alkanolamines, such as N-aminoethylethanolamine, ethanolamine, 3-aminopropanol, neopentanolamine.
In addition, monofunctional isocyanate-reactive amine compounds can also be used as component A2-I), for example methylamine, ethylamine, propylamine, butylamine, octylamine, laurylamine, stearylamine, isononyloxypropylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, N-methylaminopropylamine, diethyl (methyl) aminopropylamine, morpholine, piperidine, and suitable substituted derivatives thereof, amidoamines formed from diprimary amines and monocarboxylic acids, monoketimines (monoketimin) of diprimary amines, primary/tertiary amines, such as N, N-dimethylaminopropylamine.
As component A2-I), preference is given to using 1, 2-ethylenediamine, bis (4-aminocyclohexyl) methane, 1, 4-diaminobutane, isophoronediamine, ethanolamine, diethanolamine and diethylenetriamine.
Component A2) particularly preferably comprises at least one component A2-II). Suitable alkyl tin compounds as component A2-II). The basic structure of the compound has a primary substituent, a secondary substituent, a tertiary substituent and a quaternary substituent (the number of R is indicated).
The preparation of the polyurethane dispersions can be carried out in one or more stages in homogeneous phase or, for multistage reactions, partly in dispersed phase. In this connection, all processes known in the art can be used, for example, prepolymer mixing processes, acetone processes or melt dispersion processes. Preferably, the acetone process is used.
In the production of the polyurethane prepolymers, the mass ratio of isocyanate groups to isocyanate-reactive groups (NCO index) is generally in the range from 1.05 to 3.5, preferably in the range from 1.1 to 3.0 and particularly preferably in the range from 1.1 to 2.5.
The solids content of the polyurethane dispersions preferably used for preparing the cosmetic compositions according to the invention is generally from 10 to 70% by weight, preferably from 30 to 65% by weight, particularly preferably from 40 to 60% by weight. The solids content is determined by heating the weighed sample to constant weight at 125 ℃. The solids content was calculated by reweighing the sample at constant weight. The solids content is substantially equal to the content of polyurethane in the polyurethane dispersion.
Preferably, these polyurethane dispersions have less than 5% by weight, particularly preferably less than 0.2% by weight, based on the mass of the dispersion, of unbound organic amines. The content in the cosmetic composition is correspondingly low.
The polyurethane dispersion used for preparing the cosmetic composition of the present invention is preferably produced by COTRUNE
Figure BDA0003027131180000101
M100，
Figure BDA0003027131180000102
M170，
Figure BDA0003027131180000103
M170K，
Figure BDA0003027131180000111
M170M. In particularIt is preferable that
Figure BDA0003027131180000112
M170K。
The copolymer of the present invention comprises polymer units mainly introduced by the acrylic group-containing monomer and the amphoteric monomer described above, and polymer units introduced by other monomers are not more than 5% by weight, preferably not more than 1% by weight of the copolymer. More preferably, the copolymer is prepared from only the acrylic group-containing monomer and the amphoteric monomer described above.
In some preferred embodiments, the polymer units comprised by the copolymer may also be introduced by pyrrolidone monomers, i.e. the monomers involved in the copolymerization to obtain the amphoteric copolymer also include pyrrolidone monomers.
Preferably, the acrylic group-containing monomer includes acrylic acid, methacrylic acid, acrylic acid C1-20Alkyl esters and methacrylic acid C1-20At least one alkyl ester.
More preferably, it is selected from acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, isopropyl acrylate, isopropyl methacrylate, lauryl acrylate, lauryl methacrylate, cetyl acrylate, cetyl methacrylate, stearyl acrylate, stearyl methacrylate. Particularly preferred are acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, lauryl acrylate, lauryl methacrylate, stearyl acrylate and stearyl methacrylate.
Further preferably, the acrylic group-containing monomer includes a first monomer selected from at least one of acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, isopropyl acrylate, and isopropyl methacrylate; the second monomer is at least one selected from octadecyl acrylate and octadecyl methacrylate.
Still more preferably, the acrylic group-containing monomer further includes a third monomer selected from at least one of lauryl acrylate and lauryl methacrylate.
In some preferred embodiments, the preferred amphoteric monomer comprises at least one of a methacrylalkyl betaine and a methacrylalkylamine oxide, wherein R is2And R3In each case independently of one another from methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl, particularly preferably methyl.
More preferably, n in the structural formula is an integer of 1 to 5, preferably an integer of 1 to 3, and particularly preferably 2.
Further selected, R in the structural formula1Represents CH3。
In a particularly preferred embodiment, the acrylic group-containing monomer includes a first monomer selected from at least one of acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, isopropyl acrylate, and isopropyl methacrylate; the second monomer is at least one selected from octadecyl acrylate and octadecyl methacrylate. The third monomer is at least one of lauryl acrylate and lauryl methacrylate. The amphoteric monomer is a methacrylalkylamine oxide.
The amphoteric copolymers which meet the above conditions can be provided by the known products known in the art, including those manufactured by Mitsubishi under the trade designation
Figure BDA0003027131180000121
Z-611，
Figure BDA0003027131180000122
Z-612，
Figure BDA0003027131180000123
Z-631，
Figure BDA0003027131180000124
Z-632，
Figure BDA0003027131180000125
Z-651，
Figure BDA0003027131180000126
Z-711N and
Figure BDA0003027131180000127
Z-731N, and the like, and those produced by Lubrizol
Figure BDA0003027131180000128
G-100，
Figure BDA0003027131180000129
plus,
Figure BDA00030271311800001210
Superhold and
Figure BDA00030271311800001211
RSP, etc. Wherein the content of the first and second substances,
Figure BDA00030271311800001212
z-631 is preferred.
The cosmetic compositions provided herein comprise, in addition to the polyurethane or polyurethane dispersion described above and at least one amphoteric copolymer, a cosmetically acceptable medium, including in particular water and optionally a cosmetically suitable solvent. Wherein the solid component (polyurethane) in the polyurethane dispersion is 0.1 to 20% by weight, preferably 0.1 to 5% by weight, of the cosmetic composition. The solid component (ampholyte copolymer) in the ampholyte copolymer product is 0.1% to 20% by weight of the cosmetic composition. The weight of the solid component was determined by heating the weighed sample to a constant weight at 125 ℃. The weight of the solid component was calculated by reweighing the sample at constant weight.
In a preferred embodiment of the present invention, the weight ratio of the polyurethane to the amphoteric copolymer in the cosmetic composition is 1 to 30:1 to 30, preferably 1 to 10:1 to 10, and more preferably 3 to 5: 1.
In a preferred embodiment of the invention, the total mass of polyurethane and amphoteric copolymer is 0.1% to 30% of the total mass of the cosmetic composition.
As mentioned above, the cosmetically acceptable medium comprises, in particular, water and optionally cosmetically suitable solvents. Preferred solvents are aliphatic alcohols having C2-4 carbon atoms, such as ethanol, isopropanol, tert-butanol, n-butanol; polyols, such as propylene glycol, glycerol, ethylene glycol and polyol ethers; acetone; unbranched or branched hydrocarbons, such as pentane, hexane, isopentane and cyclic hydrocarbons, such as cyclopentane and cyclohexane; and mixtures thereof.
In a preferred embodiment of the invention, the solvent is typically ethanol.
For low VOC skin make-up compositions, such solvents are preferably present in an amount of less than 80 wt%, more preferably less than 55 wt%, even more preferably less than 40 wt%, with the remainder being water, based on the total weight of the composition.
In addition to the polyurethanes described above, the compositions according to the invention can comprise other suitable film formers which can also contribute to the make-up and styling of the skin.
The concentration of the one or more other film formers can be from 0 to 20 wt%, especially from 0 to 10 wt%, based on the total weight of the composition.
The film-forming agent may be selected from water-soluble or water-dispersible polyurethanes, other than the polyurethanes used in the present invention, polyureas, silicone resins and/or polyesters, and nonionic, anionic, amphoteric and/or cationic polymers and mixtures thereof.
The cosmetic compositions of the invention can furthermore advantageously comprise thickeners. Advantageous thickeners are: crosslinked or uncrosslinked acrylic or methacrylic acid homopolymers or copolymers; a natural thickening polymer; nonionic, anionic, cationic or amphoteric associative polymers, for example based on polyethylene glycols and their derivatives or polyurethanes; and crosslinked or uncrosslinked homopolymers or copolymers based on acrylamide or methacrylamide.
If thickeners are used, they constitute from 0 to 2% by weight, preferably from 0 to 1% by weight, of the total weight of the cosmetic composition.
The cosmetic composition according to the invention may furthermore comprise a propellant gas. The concentration of the propellant gas here is from 0 to 40% by weight, preferably from 0 to 20% by weight, based on the total weight of the formulation.
Preferably, the propellant gas is a hydrocarbon such as propane, isobutane and n-butane, and mixtures thereof. However, in embodiments of the present invention, compressed air, carbon dioxide, nitrogen dioxide and dimethyl ether, and mixtures of all of these gases can also be advantageously used.
In addition, both skin care actives and conventional additives can be used in the cosmetic compositions of the present invention. Such additives include silicones or silicone derivatives, wetting agents, humectants, emollients such as glycerin, glycols and phthalates and ethers, perfumes and fragrances, UV absorbers, dyes, pigments, and other colorants, anti-corrosion agents, neutralizers, antioxidants, anti-adhesion agents, binders and conditioners, antistatic agents, shine agents, preservatives, proteins and their derivatives, amino acids, vitamins, emulsifiers, surfactants, viscosity modifiers, thickeners and rheology modifiers, gelling agents, opacifiers, stabilizers, surfactants, sequestrants, complexing agents, pearlescers, reinforcing agents, fatty acids, fatty alcohols, triglycerides, botanical extracts, clarifying aids and film formers.
These additives are generally present in concentrations of about 0.001% to 15%, preferably 0.01% to 10% by weight, based on the total weight of the cosmetic composition.
The cosmetic compositions according to the invention, in particular the skin-setting compositions, can be in the form of gels, emulsions, solutions or creams, for example in the form of setting mousses, setting fluids, styling gels, styling creams, aerosol mousses, etc. The cosmetic composition of the present invention can be applied to the skin or the like by spraying or painting to perform a shaping and/or fixing effect.
A preferred embodiment of the skin make-up composition according to the invention is in the form of a spray, which additionally comprises one or more of the following ingredients: cosmetically suitable solvents, aliphatic alcohols having 2 to 4 carbon atoms, preferably ethanol, polyols, acetone, unbranched or branched hydrocarbons, cyclic hydrocarbons and mixtures thereof, and propellant gases, such as hydrocarbons, compressed air, carbon dioxide, nitrogen dioxide, dimethyl ether, fluorocarbons or chlorofluorocarbons, preferably dimethyl ether and/or propane/butane mixtures.
The invention is illustrated by the following examples, which should not be construed as limiting. Unless otherwise indicated, all quantitative data, fractions and percentages are by weight or based on the total weight of the composition.
The features and properties of the present invention are described in further detail below with reference to examples.
Examples
Raw materials and reagents
Figure BDA0003027131180000141
Figure BDA0003027131180000151
The examples and comparative examples of the present invention can be prepared as follows: adding butanediol, propylene glycol and rheological agent into water at a stirring speed of 500-600rpm until the mixture is uniformly dispersed; if VPVA or K-30 is required to be heated to 50 ℃ to be completely dissolved, the polyurethane (the polyurethane of the invention) is continuously added respectively
Figure BDA0003027131180000152
M170K) and ampholytic copolymer(s) ((R)
Figure BDA0003027131180000153
Z-631) and continuously stirring to uniformly disperse the mixture; at 200-300rmAnd (3) stirring and adding other raw materials at the speed of p until the raw materials are uniformly dispersed to obtain the facial make-up fixing product.
The examples or comparative examples in the present invention all have the compositions as listed in the following table:
Figure BDA0003027131180000154
by adjusting the components and the ratio of the polyurethane to the amphoteric copolymer, the example components (%) shown in the following table were obtained:
Figure BDA0003027131180000155
Figure BDA0003027131180000161
the proportions of the components in the above table refer to the percentage of the solid components in the various products used to make up the entire facial make-up. The weight ratio of the solid component in the polyurethane dispersion and the solid component in Z-631 is preferably kept in the range of 4:1 to 1: 4.
Evaluation experiment:
the prepared products are respectively smeared on the skin, after the products are completely dried, five trained people respectively smear evaluation groups of a comparative example and an embodiment to score each item, wherein 1 score is the lowest and the worst, and 10 scores are the best and the strongest. Since the scores are relative, there is no comparability between the scores of the respective groups.
TABLE 1 evaluation results of comparative example Components
Figure BDA0003027131180000162
Figure BDA0003027131180000171
FIG. 1 is plotted from the above table data.
It is demonstrated by table 1 and fig. 1 that the formulations of polyurethane and ampholyte copolymer B provided in the present application have a better overall effect than the formulations of VPVA alone or with K-30 or bauscusan C1004 in combination with Z631, especially when the mass ratio of polyurethane to ampholyte copolymer is 4:1 has the best film-forming feeling, makeup-fixing ability, easy-to-wash-off property and hardness.
When the cosmetic composition provided by the invention is applied to skin, a hard film with certain softness and elasticity can be formed, and the cosmetic composition has lasting makeup fixing capacity, excellent film-forming property and long-lasting makeup retention property under normal environment. In addition, the shampoo has excellent washing-off property.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (10)

1. A cosmetic composition, comprising: at least one polyurethane and at least one ampholytic copolymer;
the polyurethane is obtained by reacting at least one water-insoluble, non-water-dispersible isocyanate-functional polyurethane prepolymer, at least one amino-functional compound, and an alkyl tin compound;
the monomers participating in the copolymerization to obtain the amphoteric copolymer comprise acrylic group-containing monomers and amphoteric monomers, wherein the acrylic group-containing monomers are selected from at least one of acrylic acid, methacrylic acid, alkyl acrylate and alkyl methacrylate; the amphoteric monomer is selected from at least one of methacryl alkyl betaine and methacryl alkyl amine oxide;
the structural formula of the methacryl alkyl betaine is as follows:
Figure FDA0003027131170000011
the structural formula of the methacrylalkylamine oxide is as follows:
Figure FDA0003027131170000012
in the above two formulae, R1Is H or CH3，R2And R3Each independently a straight or branched chain C1-C10Alkyl, and n is an integer from 1 to 20.
2. The cosmetic composition of claim 1, wherein the monomers that participate in the copolymerization to provide the amphoteric copolymer further comprise pyrrolidone monomers.
3. The cosmetic composition according to claim 1, wherein the acrylic group-containing monomer comprises a first monomer and a second monomer, the first monomer being selected from at least one of acrylic acid, methacrylic acid, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, isopropyl acrylate, and isopropyl methacrylate; the second monomer is at least one of octadecyl acrylate and octadecyl methacrylate;
preferably, the acrylic group-containing monomer further includes a third monomer selected from at least one of lauryl acrylate and lauryl methacrylate.
4. The cosmetic composition according to claim 1, wherein R in the formula of the methacrylalkylamine oxide is1、R2And R3Are all CH3And n is 2.
5. The cosmetic composition of claim 1, wherein the amino-functional compound is selected from at least one of primary amines, secondary amines, and diamines;
preferably, the amino-functional compound is selected from at least one of diamines.
6. Cosmetic composition according to claim 1, characterized in that the polyurethane is added to the cosmetic composition in the form of a polyurethane dispersion selected from those produced by the company COTRUNE
Figure FDA0003027131170000021
M100，
Figure FDA0003027131170000022
M170、
Figure FDA0003027131170000023
M170K and
Figure FDA0003027131170000024
at least one of M170M.
7. The cosmetic composition according to any one of claims 1 to 6, wherein the prepolymer is obtained by reacting at least one of polyether polyol, polycarbonate polyol, polyether polycarbonate polyol and polyester polyol with at least one polyisocyanate;
preferably, the polyisocyanate includes at least one of hexamethylene diisocyanate and isophorone diisocyanate.
8. The cosmetic composition according to any one of claims 1 to 6, wherein the polyurethane is present in the cosmetic composition in an amount of 0.1 to 20% by mass;
preferably, the amphoteric copolymer accounts for 0.1-20% of the cosmetic composition by mass;
preferably, the total mass of the polyurethane and the amphoteric copolymer accounts for 0.1-30% of the total mass of the cosmetic composition;
preferably, the weight ratio of the polyurethane to the amphoteric copolymer is 1-30: 1-30; more preferably, the ratio of the two is 1-10: 1-10; further preferably, the ratio of the two is 3-5: 1.
9. The cosmetic composition of any one of claims 1 to 6, further comprising at least one of a polyol, a surfactant, a preservative, a fragrance, a humectant, and an active.
10. Use of the cosmetic composition according to any one of claims 1 to 9 for skin makeup fixation.
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