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MXPA06004640A - Water-soluble polyaminoamides comprising 1,3-diimines as sunscreen agents - Google Patents

Water-soluble polyaminoamides comprising 1,3-diimines as sunscreen agents

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Publication number
MXPA06004640A
MXPA06004640A MXPA/A/2006/004640A MXPA06004640A MXPA06004640A MX PA06004640 A MXPA06004640 A MX PA06004640A MX PA06004640 A MXPA06004640 A MX PA06004640A MX PA06004640 A MXPA06004640 A MX PA06004640A
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MX
Mexico
Prior art keywords
hair
groups
diimine
polyaminoamide
diimine groups
Prior art date
Application number
MXPA/A/2006/004640A
Other languages
Spanish (es)
Inventor
Z Hessefort Yin
M Carlson Wayne
Wei Mingli
Original Assignee
Nalco Company
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Filing date
Publication date
Application filed by Nalco Company filed Critical Nalco Company
Publication of MXPA06004640A publication Critical patent/MXPA06004640A/en

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Abstract

A UV-protective composition comprising a water-soluble polyaminoamide containing 1,3-diimine groups, wherein the polyaminoamide containing 1,3-diimine groups absorbs ultraviolet light radiation having a wavelength of about 200nm to about 420nm, and methods of treating substrates with the UV-protective polyaminoamide containing 1,3-diimine groups.

Description

POLYAMINOAMIDAS HYDROSOLUBLES COMPRISING 1,3-DIAMINES AS AGENTS OF SOLAR FILTER FIELD OF THE INVENTION This invention relates to compositions comprising polyaminoamides containing 1,3-diimine groups and methods of use in the compositions for protecting substrates from the damaging effects of ultraviolet radiation. BACKGROUND OF THE INVENTION Ultraviolet (UV) light radiation is known to be a factor that damages wood, paints and other protective or decorative coatings, plastics, various textiles made from natural and man-made fibers, keratin substrates that They include the skin and human hair. Damage to human skin, for example, may include loss of skin elasticity and appearance of wrinkles, erythema and skin burns and the induction of phototoxic or photoallergic reactions. Damage to hair by UV light is perceived as dryness, reduced strength, rough surface texture, loss of color and luster, stiffness and brittleness. In the case of plastics, exposure to UV radiation can result in loss of tensile strength, generation of a brittle condition and color change. Exposure to UV radiation may also result Ref .: 170891 in diminishing painted surfaces or dyed textiles. To help avoid such degradation, ultraviolet light stabilizers are often incorporated into a polymeric composition, which is used as a protective topcoat for underlying materials. The protection of skin and hair exposed to UV exposure can be carried out by applying directly to the skin and hair a preparation containing a portion that absorbs UV radiation. Generally, sunscreens for hair application require substantivity (adhesion) to hair and compatibility with hair care formulations which are often based on water. However, many sunscreen agents do not fully meet these requirements. In this way, the level of sunscreen agents that can be incorporated into the hair care formulations and / or the concentration of sunscreen agents that can be deposited on the hair are limited. Accordingly, there is a need for new sunscreen agents with improved substantivity and water solubility for incorporation into aqueous formulations. The skin and hair can also be protected by covering it with a garment, and in this way direct exposure of the skin and hair to sunlight is avoided. However, most natural and synthetic textiles are permeable, at least partially to UV radiation components of sunlight. Consequently, the mere fact of using clothing does not necessarily provide the skin under garments with adequate protection against UV radiation damage. Although the garments contain colorants with deep colors and / or have a tight wavy texture and can provide a reasonable level of protection to the skin beneath it, such garments are not practical in hot sunny climates, from the point of view of the personal comfort of the user. Therefore, there is still a need to provide protection against UV radiation for the skin, which is under clothing that includes lightweight summer clothing, which is not stained or dyed only in light tones. The commonly used UV absorbing substances such as benzotriazoles and benzophenones are highly effective in their ability to absorb UV radiation. However, they are very expensive and may prove difficult to incorporate into different objective means. Furthermore, the UV absorbing substances of this type do not show substantivity to the hair and present handling difficulties insofar as they are generally produced and used in pulverized form and have relatively low melting points. On the other hand, a liquid is much easier to handle, does not require fusion or provides more efficient and complete mixing through the target material. Therefore, there is a continuing need for effective liquid compositions that absorb UV radiation which have sufficient versatility to be incorporated into or applied to different media and substrates. SUMMARY OF THE INVENTION This invention is a composition for protecting a substrate from the effect of ultraviolet light, comprising an effective protective amount of UV radiation of one or more water-soluble polyaminoamides containing 1,3-diimine groups, wherein the polyaminoamides which They contain 1,3-diimine groups absorb ultraviolet light radiation having a wavelength of about 200 nm to about 420 nm. This invention is also a method for protecting a substrate from the effect of ultraviolet light comprising applying to the substrate an effective protective amount of UV radiation of a composition comprising an effective protective amount of UV radiation of one or more water-soluble polyaminoamides containing groups. 1,3-diimine, wherein the polyaminoamides containing 1,3-diimine groups absorb ultraviolet light radiation - having a wavelength of about 200 nm to about 420 n. DETAILED DESCRIPTION OF THE INVENTION This invention is a composition for protecting a substrate from the effect of ultraviolet light, comprising an effective protective amount of UV radiation of one or more water-soluble novel polyaminoamides containing 1,3-diimine groups. The term "polyaminoamide containing 1,3-diimine groups" means a polyaminoamide prepared as described herein which contains one or more groups of formula (I) which result from the prolonged heating of a polyaminoamide at elevated temperatures relative to the temperature used in the formation of the polyaminoamide.
The synthesis of the polyaminoamide containing 1,3-diimine groups involves two stages of reactions. The first step is the formation of the polyaminoamide without the targeted formation of imidazoline and imine groups. The second step is the formation of the imidazoline ring and the 1,3-diimine structures by prolonged heating at elevated temperatures (preferably> 180 ° C) which are much higher than the temperatures required for the first stage condensation reaction (usually lower than 160 ° C). Heating to a higher temperature promotes the formation of the imidazoline ring and the imine group. The 1,3-diimine group can be formed by an intramolecular or intermolecular reaction. The formation of a polyaminoamide containing bicyclic 1,3-diimine resulting from the intramolecular reaction of a polyaminoamide comprising repeated groups of diethylenetriamine (DETA) is shown in Reaction Scheme 1. The formation of a polyaminoamide containing units 1, 3-Diimine resulting from the intermolecular reaction of polyaminoamides comprising repeated diethylenetriamine groups (DETA) is shown in reaction scheme 2.
Reaction Scheme 1 UV absorption: 280-350 nm. Reaction Scheme 2 UV absorption: 280-350 nm The formation of the bicyclic and exocyclic 1,3-diimine structures has been confirmed by NMR studies. The difference between the regular polyaminoamide polymers and the polymers containing 1,3-diimine can easily be distinguished by three new peaks in their 13C NMR. The regular polyaminoamide does not show UV absorption at 280-350 nm due to the lack of the 1,3-diimine structure, the existence of 1,3-diimine can also be identified by a strong UV absorption around 300-350 nm due to its tautomeric balance of enamine-imine. The water-soluble polyaminoamides used as starting material for the polyaminoamides containing 1,3-diimine groups are well known in the art and can be prepared by the polycondensation of one or more organic dicarboxylic acid derivatives and one or more diamines. Representative polyaminoamides suitable for conversion to polyaminoamides containing 1,3-diimine groups include those described in the U.S. Patents. Nos. 4,201,776, 4,866,159, 5,350,796, 6,222,006, 6,352,613, EP 0320121 and the document of E.U.A. commonly assigned Serial No. 10 / 665,163, filed September 4, 2003. The organic dicarboxylic acid derivative includes aliphatic or aromatic dicarboxylic acids and corresponding chlorides, anhydrides and diacid esters thereof. Representative organic dicarboxylic acid derivatives include the acids: maleic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebasic, italic, isophthalic, terephthalic, naphthalenedicarboxylic, dimethyl maleate, dimethyl malonate, dimethyl succinate, diethyl glutarate , dimethyl adipate, dimethyl sebacate, dimethyl phthalate, dimethyl isophthalate, dimethyl terephthalate, dimethyl naphthalenedicarboxylate, dibasic esters (DBE), poly (ethylene glycol) bis (carboxymethyl) ether, succinyl chloride, glutaryl dichloride, chloride of adipoyl, sebacoyl chloride, sebacate, phthaloyl chloride, isophthaloyl chloride, terephthaloyl chloride, naphthalenedicarboxylate, maleic anhydride, succinic anhydride, glutaric anhydride, italic anhydride, 1,8-naphthaic anhydride and the like. Preferred are dimethyl terephthalate, adipic acid and dibasic DBE ester. The diamine is selected from aliphatic or aromatic organic compounds having at least two amino groups (~ NH2). Representative diamines include ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,4-diaminobutane, hexamethylenediamine (HMDA), 1,1-diaminodecane, phenylenediamine (all isomers), naphthalenediamine (all isomers), diamines JEFFAMINE1 ^, bis (aminoethyl) -N, N'-piperazine, bis (aminopropyl) -N, N'-piperazine, polyalkyleneamines such as diethylenetriamine (DETA), triethylenetetraamine (TETA), tetraethylenepentamine (TEPA) and the like. Diethylenetriamine is preferred. In one aspect of this invention, terminal amino groups (-NH2) in the starting material of polyaminoamide or polyaminoamide containing 1,3-diimine groups may be capped at the end with molecules containing portions that absorb UV radiation. Representative molecules containing portions that absorb UV radiation include acyl or sulfonyl aromatic derivatives such as cinnamoyl, optionally substituted with one or more alkoxy groups, p-dialkylaminobenzoyl, salicyloyl, acyl residues that originate from a carboxylic or sulfonic acid derived from benzylidiencamphor, sulfonyl residues that originate from isophthalidenecamphor, acyl residues that originate from a carboxylic or sulphonic acid that is derived from 2-arylbenzimidazoles, 2-arylbenzoxazoles, 2-arylbenzotriazoles, 2-arylbenzofranes, 2-arylindoles, acyl residues derived from an absorber of coumarin carboxylic structure, sulfonyl residues originating from terephthalidene camphor, sulfonyl residues derived from benzylidenecamphor, substituted on the aromatic ring with one or more lower alkoxy radicals, acyl residues originating from a carboxylic or sulphonic acid derived from 2-arylbenzotriazoles, residues acyl derived from an abso monofenylcyanoacrylic or diphenylcyanoacrylic structure, acyl residues derived from an optionally substituted dibenzoylmethane structure absorber and the like. Preferred molecules containing portions that absorb UV radiation include the substituted and unsubstituted forms of cinnamoyl, salicyloyl and p-dialkylaminobenzoyl. In a preferred aspect of this invention, the portion that absorbs UV radiation absorbs UV radiation having a wavelength of about 280 nm to about 400 nm. If desired, the initial polyaminoamide material or the polyaminoamide containing 1,3-diimine groups can be crosslinked using one or more crosslinking agents. Preferred crosslinking agents include diepoxides, dianhydrides, dihalogen derivatives, diesters, diacids, epihalo-idrins and epihalohydrin / amine oligomers. More preferred crosslinking agents include poly (ethylene glycol) diglycidyl ether, poly (propylene glycol) diglycidyl ether, epichlorohydrin and epichlorohydrin / dimethylamine oligomers. The polyaminoamide containing 1,3-diimine groups can also be reacted with one or more modifiers that are selected from the group consisting of the portions containing cationic functional groups, portions containing anionic functional groups and portions containing substituted aliphatic hydrocarbons or not substituted in order to impart anionic, cationic or amphoteric properties to the polymer. The term "portions containing cationic functional groups" includes any molecule that contains a cationic functional group and also a group that is sufficiently reactive to form a covalent bond with one or more secondary amino groups of the polyaminoamide. Preferred portions containing cationic functional groups include glycidyltrimethylammonium chloride, N- (3-chloro-2-hydroxypropyl) trimethylammonium chloride, and the like. The term "portions containing anionic functional groups" includes any molecule that contains an anionic functional group and also a group that is sufficiently reactive to form a covalent bond with one or more of the aminosecundaries of the polyaminoamide. Preferred portions containing anionic functional groups include chloroacetic acid and the salts thereof, 1,3-propanesultone, 1,4-butanesultone and the like. Portions containing the substituted or unsubstituted forms of aliphatic hydrocarbons typically have the formula R-Xwherein X is halogen, epoxide, acyl, anhydride, acid, ester, halohydrin and R is any linear or branched, saturated or unsaturated, substituted or unsubstituted aliphatic hydrocarbon. Preferred portions containing the substituted or unsubstituted aliphatic hydrocarbons include glycidyl ethers of aliphatic alcohols of 6 to 18 carbon atoms. In another aspect, this invention is a composition for protecting a substrate from the effect of ultraviolet light, comprising an effective protective amount of UV radiation of one or more water-soluble polyaminoamides containing 1,3-diimine groups, wherein the polyaminoamides containing 1,3-diimine groups absorb ultraviolet light radiation having a wavelength of about 200 nm to about 420 nm. In a preferred aspect of this invention, the polyaminoamide is combined with one or more cosmetically acceptable excipients to prepare a composition for application to keratin substrates including hair, skin and nails. Typical compositions for application to keratin substrates comprise from about 0.1 to about 10% by weight of water-soluble polyaminoamide, based on the weight of the composition. In a preferred aspect of this invention, the keratin substrate is the skin. In another preferred aspect, the keratin substrate is hair. One advantage of polyaminoamide of this invention is that the polymer can alternatively contain cationic, anionic and / or ampholytic (or amphoteric) characteristics resulting in a "multifunctional" nature that offers hair and skin conditioning benefits and that improves the operation of the polymer for conditioning, dye retention, etcetera. The term "cosmetically acceptable excipient" means a non-toxic and non-irritating substance which, when mixed with the UV absorbing polymer of this invention, renders the polymer more suitable to be applied to the skin or hair. In another preferred aspect, the excipients are selected from the group consisting of saccharides, surfactants, humectants, petrolatum, mineral oil, fatty alcohols, fatty ester emollients, waxes and waxes containing silicone, silicone oil, silicone fluid, surfactants silicone, volatile hydrocarbon oils, quaternary nitrogen compounds, silicones with functionalized amine, conditioning polymers, rheology modifiers, antioxidants, sunscreen active agents, long chain diamines from about 10 to 22 carbon atoms, chain fatty amines long from about 10 to 22 carbon atoms, fatty alcohols, ethoxylated fatty alcohols and dicola phospholipids. Representative saccharides include nonionic or cationic saccharides such as agarose, amylopectins, amylose, arabinans, arabinogalactans, arabinoxylenes, carrageenans, gum arabic, carboxymethyl guar gum, carboxymethyl (hydroxypropyl) guar gum, hydroxyethyl guar gum, carboxymethyl cellulose, cationic guar gum, ethers of cellulose including methylcellulose, chondroitins, chitins, chitosan, chitosan pyrrolidone carboxylate, chitosan-glycolate-lactose-lactate, cocodimonium hydroxypropyloxyethylcellulose, colominic acid ([poly-N-acetyl-neuraminic acid]), corn starch, curdlan, dermatin sulfate, dextrans , furcellarans, dextrans, crosslinked dextrans, dextrin, emulsan, ethylhydroxyethylcellulose, flax seed saccharides (acid), galactoglucomannans, galactomannans, glucomannans, glycogens, guar gum, hydroxyethylstarch, hydroxypropylmethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylstarch, hydrogenated guar gums oxypropylates, gelano gum, ghatti gum, karaya gum, tragacanth gum (tragacanthine), heparin, hyaluronic acid, inulin, keratin sulfate, konjac's morning, modified starches, laminar, laurdimonium hydroxypropyloxyethylcellulose, okra gum, oxidized starch, pectic acids, pectin, polydextrose, polyquaternium-4, polyquaternium-10, polyquaternium-28, potato starch, protepectins, psyllium seed gum, pullulan, sodium hyaluronate, starch diethylaminoethyl ether, hydroxyethylcellulose stearimonium, raffinose, ramsano, tapioca starch, velano, levane, scleroglucan, sodium alginate, stanquilose, succinoglucan, wheat starch, xanthan gum, xylans, xyloglucans and mixtures thereof. Microbial saccharides can be found in Kirk-Othmer Encyclopedia of Chemical Technology, Fourth Edition, Vol. 16, John Wiley and Sons, NY p. 578-611 (1994) which is incorporated completely as a reference. Complex carbohydrates are found in Encyclopedia of Chemical Technology, Fourth Edition, vol. 4, John Wiley and Sons, NY pp. 930-948, 1995, which is incorporated herein by reference. Typical compositions for application to keratin substrates comprise about 1 to about 3 weight percent, based on the polymer active of the polyaminoamide containing 1,3-diimine groups of this invention. The cosmetically acceptable composition of this invention may include surfactants. Surfactants include surfactants, which typically provide detersive functionality to a formulation or act simply as wetting agents. Surfactants can generally be classified as anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants and zwitterionic surfactants and dispersion polymers. Anionic surfactants useful herein include those described in the U.S. Pat. No. 5,573,709, incorporated herein by reference. Examples include alkyl and alkyl ether sulfates. Specific examples of alkyl ether sulfates which can be used in this invention are sodium and ammonium salts of lauryl sulfate, lauryl ether sulfate, alkyltriethylene glycol ether sulfate coconut; tallow alkyltriethylene glycol ether sulphate and tallow alkyl hexamethylene sulphate. Highly preferred alkyl ether sulfates are those which comprise a mixture of individual compounds, the mixture has an average alkyl chain length of from about 12 to about 16 carbon atoms and an average degree of ethoxylation of from about 1 to about 6 moles of ethylene. Another suitable class of anionic surfactants are the salts of alkylsulfuric acid. Important examples are the salts of a reaction product of organic sulfuric acid of a hydrocarbon of the methane series including isoparaffins, neoparaffins, inesoparaffins and n-paraffins, having about 8 to about 24 carbon atoms, preferably about 12 to about 18 carbon atoms and a sulfonating agent, for example, S03, H2SO4, fuming sulfuric acid, which is obtained according to known sulfonating methods including bleaching and hydrolysis. Preferred are n-paraffins of 12 to 38 sulfated carbon atoms of alkali metal and ammonium. Additional synthetic anionic surfactants include the olefin sulfonates, the β-alkyloxy alkane sulphonates and the reaction products of fatty acids esterified with isethionic acid and neutralized with sodium hydroxide as well as succinamates. Specific examples of succinamates include disodium N-octadecylsulfosuccinamate; N- (1,2-dicarboxyethyl) -N-octadecylsulfosuccinamate tetrasodium; diamyl ester of sodium sulfosuccinic acid; sodium sulfosuccinic acid diethyl ester; dioctyl esters of sodium sulfosuccinic acid. Preferred anionic surfactants for use in a cosmetically acceptable composition of this invention include ammonium lauryl sulfate, ammonium laureth sulfate, triethylamine lauryl sulfate, triethylamine laureth sulfate, triethanolamine lauryl sulfate, triethanolamine laureth sulfate, monoethanolamine lauryl sulfate, monoethanolamine laureth sulfate, lauryl sulfate. of diethanolamine, diethanolamine laureth sulfate, lauryl onoglyceride sodium sulfate, sodium lauryl sulfate, sodium laureth sulfate, potassium lauryl sulfate, potassium laureth sulfate, sodium lauryl sarcosinate, sodium lauroyl sarcosinate, lauryl sarcosine, cocoyl sarcosine, ammonium cocoyl sulfate, Ammonium lauroylsulfate, sodium cocoylsulfate, sodium lauroylsulfate, potassium cocoylsulfate, potassium lauryl sulfate, triethanolamine lauryl sulfate, triethanolamine lauryl sulfate, monoethanolamine cocoylsulfate, monoethanolamine lauryl sulfate, tridecylbenzenesulfonate hatred and sodium dodecylbenzenesulfonate. Amphoteric surfactants which can be used in a cosmetically acceptable composition of this invention include derivatives of aliphatic secondary and tertiary amines in which the aliphatic substituent contains from about 8 to 18 carbon atoms and an anionic water solubilizing group, for example carboxy, sulfonate, sulfate, phosphate or phosphonate. Representative examples include sodium 3-dodecylaminopropionate, sodium 3-dodecylaminopropanesulfonate, sodium lauryl sarcosinate, iV-alkyl taurines such as one prepared by reacting dodecylamine with sodium isethionate as described in US Pat. No. 2,658,072, N-higher alkylapartic acid, as described in the U.S. Patent. 2,438,091 and the products sold under the trade name MIRAN0LMR as described in the U.S. Patent. 2,528,378. Other sarcosinates and sarcosinate derivatives can be found in the CTFA Cosmetic Ingredient Handbook, Fifth Edition, 1988, page 42, incorporated herein by reference. The quaternary ammonium compounds can also be used in a cosmetically acceptable composition of this invention insofar as they are compatible in the compositions of the invention, wherein the structure is provided in the CTFA Cosmetic Ingredient Handbook, Fifth Edition, 1988, page 40. Cationic surfactants generally include, but are not limited to, fatty quaternary ammonium compounds containing from about 8 to about 18 carbon atoms. . The anion of the quaternary ammonium compound can be a common ion such as chloride, ethfate, methfate, acetate, bromide, lactate, nitrate, phosphate or tosylate and mixtures thereof. The long chain alkyl groups may include a carbon or additional or substituted hydrogen atoms, or ether linkages. Other substitutions of the quaternary nitrogen may be hydrogen, hydrogen, benzyl or short chain alkyl or hydroxyalkyl groups such as methyl, ethyl, hydroxymethyl or hydroxyethyl, hydroxypropyl or combinations thereof. Examples of quaternary ammonium compounds include but are not limited to: behentrimonium chloride, cocotrimonium chloride, cetethyldimonium bromide, dibehenyldimonium chloride, dihydrogenated tallow benzylmonium chloride, disoyadimonium chloride, disodivimonium chloride, hydroxyethylhydroxyethyldimonium chloride, chloride of hydroxyethylbehenamidopropildimonium, hydroxyethyl ketaltylammonium chloride, hydroxyethylbutyboimonum chloride, myristallium chloride, PEG-2 oleammonium chloride, PEG-5 stearmonium chloride, PEG-15 cocoylquaternium 4, PEG-2 stearalkonium 4, lauryltrimonium chloride; quaternium-16; quaternium-18, lauralconium chloride, olealconium chloride, cetylpyridinium chloride, polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium-10, polyquaternium-22, polyquaternium-37, polyquaternium-39, polyquaternium-47, cetyltrimonium, dilaurildimonium chloride, ketalconium chloride, dicetildimonium chloride, soyatrimonium chloride, stearylctyldimonium methosulfate and mixtures thereof. Other quaternary ammonium compounds are included in the CTFA Cosmetic Ingredient Handbook, First Edition, pages 41-42, incorporated herein by reference. Cosmetically acceptable compositions may include long chain diamines of about 10 to 22 carbon atoms, long chain fatty amines of about 10 to 22 carbon atoms and mixtures thereof. Specific examples include dipalmitylamine, lauramidopropyldimethyl, stearamidopropyldimethylamine. The cosmetically acceptable compositions of this invention can also include fatty alcohols (typically monohydric alcohols), ethoxylated fatty alcohols and di-cola phospholipids which can be used to stabilize the emulsion or dispersion forms of the cosmetically acceptable compositions. They also provide a cosmetically acceptable viscosity. The selection of fatty alcohol is not critical, although some alcohols are characterized by having fatty chains of 10 to 32 carbon atoms, preferably 14 to 22 carbon atoms, which are substantially saturated alkanols, are those that will generally be used. Examples include stearyl alcohol, cetyl alcohol, ketostearyl alcohol, myristyl alcohol, behenyl alcohol, arachidonic alcohol, isostearyl alcohol and isocetyl alcohol. Cetyl alcohol is preferred and can be used alone or in combination with other fatty alcohols, preferably with stearyl alcohol. When the fatty alcohol is used it is preferably included in the formulations of this invention in a concentration within the range of from about 1 to about 8 weight percent, more preferably from about 2 to about 6 weight percent. The fatty alcohols can also be ethoxylated. Specific examples include cetereth-20, steareth-20, steareth-21 and mixtures thereof. Phospholipids such as phosphatidylserine and phosphatidylcholine and mixtures thereof may also be included. When used, the fatty alcohol component is included in the formulations in a concentration of about 1 to about 10 weight percent, more preferably about 2 to about 7 weight percent. The nonionic surfactants which may be used in the cosmetically acceptable composition of this invention include those generally defined as compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with an organic hydrophobic compound, which may be aliphatic or alkylaromatic in nature. Examples of preferred classes of nonionic surfactants are: long-chain alkalonamides, polyethylene oxide condensates of alkylphenols; the condensation product of aliphatic alcohols having from about 8 to about 18 carbon atoms, either in a straight chain or in a branched chain configuration, with ethylene oxide; the long chain tertiary amine oxides;the long chain tertiary phosphine oxides; the long chain dialkyl sulfoxides containing a short chain alkyl or a hydroxyalkyl radical of about 1 to about 3 carbon atoms; and alkyl polysaccharide surfactants (APS) such as alkyl polyglycosides; glyceryl fatty esters of polyethylene glycol (PEG). Zwitterionic surfactants such as betaines may also be useful in the cosmetically acceptable composition of this invention. Examples of betaine useful herein include the high alkyl betaines such as cocodimethylcarboxymethylbetaine, cocoamidopropylbetaine, cocobetaine, laurylamidopropylbetaine, oleylbetaine, lauryldimethylcarboxymethylbetaine, lauryldimethyl-a-carboxyethylbetaine, cetyldimethylcarboxymethylbetaine, lauryl bis (2-hydroxyethyl) carboxymethylbetaine, stearyl bis (2- hydroxypropyl) carboxymethylbetaine, oleyldimethyl-α-carboxypropylbetaine and lauryl bis (2-hydroxypropyl-α-carboxyethylbetaine) The sulfobetaines may be represented by cocodimethylsulfopropylbetaine, stearyldi ethylsulfopropylbetaine, lauryldimethylsulfoethylbetaine, lauryl bis (2-hydroxyethyl) sulfopropylbetaine and the like, aminobetaines and amidosulfobetaines wherein the radical RCONH (CH2) 3 is bonded to the nitrogen atom of betaine, also useful in this invention are the anionic, cationic, nonionic, amphoteric or zwitterionic surfactants used in the composition The cosmetically acceptable composition of this invention is typically used in an amount of about 0.1 to 50 weight percent, preferably about 0.5 to about 40 weight percent, more preferably about 1 to about 20 weight percent . The cosmetically acceptable composition of this invention may include humectants, which act as hygroscopic agents, which increase the amount of water absorbed, captured or retained. Suitable humectants for the formulations of this invention include but are not limited to: acetamide MEA, ammonium lactate, chitosan and its derivatives, colloidal wheat flour, galactoarabinone, glucose glutamate, glerecyth-7, glygeryth-12, glycereth-26 , glyceryth-31, glycerin, lactamide MEA, lactamide DEA, lactic acid, methyl gluceth-10, methyl gluceth-20, panthenol, propylene glycol, sorbitol, polyethylene glycol, 1,3-butanediol, 1,2,6-hexanotriol, hydrolyzed hydrogenated starch, inositol, mannitol, PEG-5, pentaerythritol ether, polyglyceryl sorbitol, xylitol, sucrose, sodium hyaluronate, sodium PCA and combinations thereof. Glycerin is a particularly preferred humectant. The humectant is present in the composition in concentrations of from about 0.5 to about 40 weight percent, preferably from about 0.5 to about 20 weight percent, and more preferably from about 0.5 to about 12 weight percent. The cosmetically acceptable composition of this invention may include petrolatum or mineral oil components, which, when selected, will generally be USP or NF grade. The petrolatum can be white or yellow. The viscosity or degree of consistency of the petrolatum is not narrowly critical. The petrolatum can be partially replaced with mixtures of hydrocarbon materials which can be formulated to remind the petrolatum in appearance and consistency. For example, mixtures of petrolatum and mineral oil with different waxes and the like can be combined. Preferred waxes include laurel berry wax, candelilla wax, ceresin, jojoba butter, lanolin wax, mountain wax, ozokerite, polyglyceryl-3-beeswax, polyglyceryl-6-penta-stearate, microcrystalline wax, paraffin wax, isoparaffin, solid petrolatum paraffin, squalene, oligomeric olefins, beeswax, synthetic candelilla wax, synthetic carnauba, synthetic beeswax and the like which can be combined together. Alkylmethylsiloxanes with varying degrees of substitution can be used to increase the water retained by the skin. Siloxanes such as stearyldimethicone, known as 2503 Wax, alkylmethane of 30 to 45 carbon atoms, known as AMS-C30 Wax and stearoxytrimethylsilane (and) stearyl alcohol, known as 580 Wax, each available from Dow Corning "11, Midland, MI, USA. Additional alkyl and phenylsilicones can be used to improve the wetting properties Resins such as dimethicone (and) trimethylsiloxysilicate known as Dow Corning ™ 593 or cyclomethicone (and) trimethylsiloxysilicate, known as Dow Corning ™ 749 fluid, can be used to improve the formation of film of skin care products When used, the petrolatum the wax or the hydrocarbon or oil component is included in the formulations in a concentration of about 1 to about 20 weight percent, more preferably about 1 to 20 weight percent. about 12 weight percent When used, the silicone resins may be included from about 0.1 to about 10.0 po r cent in weight. Emollients are defined as agents that help maintain the smoothness, smoothness and flexible appearance of the skin. Emollients work by their ability to remain on the surface of the skin or in the corneal extract. The cosmetically acceptable composition of this invention may include fatty ester emollients, which are included in the International Cosmetic Ingredient Dictionary, Eighth Edition, 2000, p. 1768 to 1773. Specific examples of fatty esters suitable for use in the formulation of this invention include isopropyl myristate, isopropyl palmitate, caprylic / capric triglycerides, cetyl lactate, cetyl palmitate, hydrogenated castor oil, glyceryl esters, hydroxyethyl isostearate, hydroxyethyl phosphate, isopropyl isostearate, isostearyl isostearate, diisopropyl sebacate, PPG-5-Ceteth-20, 2-ethylhexyl isononoate, 2-ethylhexyl stearate, fatty alcohol lactate of 12 to 16 carbon atoms carbon, isopropyl lanolate, 2-ethylhexyl salicylate and mixtures thereof. Currently preferred fatty esters are isopropyl myristate, isopropyl palmitate, PPG-5-Ceteth-20 and caprylic / capric triglycerides. When used, the fatty ester emollient is preferably included in the formulations of this invention in a concentration of about 1 to about 8 weight percent, more preferably about 2 to about 5 weight percent. The compositions of this invention may also include silicone compounds. Preferably, the viscosity of the silicone component at a temperature of 25 ° C is from about 0.5 to about 12,500 cps. Examples of suitable materials are dimethylpolysiloxane, diethylpolysiloxane, dimethylpolysiloxane-diphenylpolysiloxane, cyclomethicone, trimethylolpolysiloxane, diphenylpolysiloxane and mixtures thereof. Dimethicone and dimethylpolysiloxane blocked at the ends with trimethyl units is a preferred example. Dimethicone having a viscosity between 50 and 1,000 cps is particularly preferred. When used, silicone oils are preferably included in the formulations of this invention and at a concentration of 0.1 to 5 weight percent, more preferably 1 to 2 weight percent. The cosmetically acceptable compositions of this invention can include volatile and non-volatile silicone oils or fluids. The silicone compounds can be linear or cyclic polydimethylsiloxanes with a viscosity of about 0.5 to about 100 centistokes. The most preferred linear polydimethylsiloxane compounds have a range of about 0.5 to 50 centistokes. An example of a volatile, low molecular weight, linear polydimethylsiloxane is octamethyltrisiloxane, available under the tradename Dow Corning ™ 200 fluid having a viscosity of about 1 centistoque. When they used, silicone oils are preferably included in the formulations of this invention in a concentration of 0.1 to 30 weight percent, more preferably 1 to 20 weight percent. The cosmetically acceptable compositions of this invention may include low molecular weight, cyclic, volatile polydimethylsiloxanes (cyclomethicones). Preferred cyclic volatile siloxanes can be polydimethylcyclosiloxanes having an average repeat unit of 4 to 6, and a viscosity of about 2.0 to about 7.0 centistokes, and mixtures thereof. Preferred cyclomethicones are available from Dow Corning ™ Midland, MI, USA under the trade names Dow Corning ™ 244 fluid, Dow Corning ™ 245 fluid, Dow Corning ™ 246, Dow Corning ™ 344 fluid and Dow Corning ™ 345 fluid and Silicone SF- 1173 and Silicone SF-1202 from General Electric, Waterford, NY, USA. When used, silicone oils are preferably included in the formulations of this invention in a concentration of 0.1 to 30 weight percent, more preferably 1 to 20 weight percent. Silicone surfactants or emulsifiers with polyoxyethylene or polyoxypropylene side chains can also be used in compositions of the present invention. Preferred examples include dimethicone copolyols, Dow Corning ™ 3225C and 5225C Formulation Aids, available from Dow Corning, Midland, MI, USA and Silicone SF-1528, available from General Electric, Waterford, NY, USA. The side chains may also include alkyl groups such as lauryl or cetyl. Preferred is the laurylmethicone copolyol known as Dow Corning ™ 5200 Formulation Aid, and the cetyldimethicone copolyol known as Abil EM-90, available from Goldschmidt Chemical Corporation, Hopewell, VA. 'Lauryldimethicone, known as Belsil LDM 3107 VP, available from Wacker-Chemie, Munich Germany, is also preferred. When used, silicone surfactants are preferably included in the formulations of this invention in a concentration of 0.1 to 30 weight percent, more preferably 1 to 15 weight percent. Amine-functionalized silicones and emulsions can be used in the present invention. Preferred examples include Dow Corning ™ 8220, Dow Corning ™ 939, Dow Corning ™ 949, Dow Corning ™ 2-8194, all available from Dow Corning, Midland, MI, USA. Silicone SM 253 available from General Electric, Waterford, NY, USA is also preferred. When used, amine-functionalized silicones are preferably included in the formulations of this invention at a concentration of 0.1 to 5 weight percent, more preferably 0.1 to 2.0 weight percent. The cosmetically acceptable compositions of this invention can include volatile hydrocarbon oils.
The volatile hydrocarbon comprises from about 6 to 22 carbon atoms. A preferred volatile hydrocarbon is an aliphatic hydrocarbon having a chain length of about 6 to 16 carbon atoms. An example of such a compound includes isohexadecane, under the tradename Permethyl 101A, available from Presperse, South Plainfield, NJ. USA Another example of a preferred volatile hydrocarbon is isoparaffin of 12 to 14 carbon atoms, under the trade name Isopar M, available from Exxon, Baytown, TX. When used, volatile hydrocarbons are preferably included in the formulations of this invention at a concentration of 0.1 to 30 weight percent, more preferably 1 to 20 weight percent. The cosmetically acceptable compositions of this invention may include cationic and ampholytic conditioning polymers. Examples thereof include, but are not limited to, those indicated by the International Cosmetic Ingredient Dictionary published by the Cosmetic, Toiletry and Fragrance Association (CTFA), 1101-17th Street, N.W. , Suite 300, Washington D.C. 20036. General examples include quaternary derivatives of cellulose ethers, guar quaternary derivatives, homopolymers and copolymers of DADMAC, MAPTAC homopolymers and copolymers and quaternary derivatives of starches. Specific examples, using the CTFA designation include, but are not limited to polyquaternium-10, guar hydroxypropyltrimonium chloride, hydroxypropyltrimonium starch chloride, polyquaternium-4, polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium-14, polyquaternium -15, polyquaternium-22, polyquaternium-24, polyquaternium-28, polyquaternium-32, polyquaternium-33, polyquaternium-36, polyquaternium-37, polyquaternium-39, polyquaternium-45, polyquaternium-47 and polymethacrylamidopropyltrimonium chloride, and mixtures of the same. When used, conditioning polymers are preferably included in the cosmetically acceptable composition of this invention in a concentration of 0.1 to 10 weight percent, preferably 0.2 to 6 weight percent, and more preferably 0.2 to 5 weight percent. cent in weight. The cosmetically acceptable composition of this invention can include one or more rheology modifiers. The rheological modifiers which can be used in this invention include, but are not limited to, high molecular weight crosslinked homopolymers of acrylic acid and cross-linked acrylates / alkyl acrylate polymers of 10 to 30 carbon atoms such as the Carbopol ™ series and Pemulen ™, both available from BF Goodrich, Akron, OH, USA; anionic acrylate polymers such as Saleare ™ AST and cationic acrylate polymers such as Saleare ™ SC96, available from Ciba Specialties, High Point, NC. USA; acrylamidopropyl trimonium chloride / acrylamide; polymers of hydroxyethyl methacrylate, Steareth-10 allyl ether / acrylate copolymer; acrylates / methacrylate copolymer of Beheneth-25, known as Aculyn ™ 28, available from International Specialties, Wayen, NJ. USA; glyceryl polymethacrylate, acrylates / methacrylate copolymer of steareth-20; bentonite; gums such as alginates, carrageenans, acacia gum, gum arabic, ghatti gum, karaya gum, tragacanth gum, guar gum; hydroxypropyltrimonguar chloride, xanthan gum or gellan gum; cellulose derivatives such as sodium carboxymethylcellulose, hydroxyethylcellulose, hydroxymethylcarboxyethylcellulose, hydroxymethylcarboxypropylcellulose, ethylcellulose, sulphated cellulose, hydroxypropylcellulose, methylcellulose, hydroxypropylmethylcellulose, microcrystalline cellulose; agar; pectin; jelly; starch and its derivatives; chitosan and its derivatives such as hydroxyethyl chitosan; polyvinyl alcohol, PVM / MA copolymer, PVM / MA decadiene cross polymer, thickeners based on poly (ethylene oxide), sodium carbomer and mixtures thereof. When used, rheology modifiers are preferably included in the cosmetically acceptable composition of this invention in a concentration of 0.01 to 12 weight percent, preferably from 0.05 to 10 weight percent and more preferably from 0.1 to 6 weight percent. The cosmetically acceptable composition of this invention may include one or more antioxidants which include, but are not limited to, ascorbic acid, BHT, BHA, erythorbic acid, bisulfite, thioglycolate, tocopherol, sodium metabisulfite, vitamin E acetate and ascorbyl palmitate. . Antioxidants will be present from 0.01 to 5 weight percent, preferably 0.1 to 3 weight percent, and more preferably from 0.2 to 2 weight percent of the cosmetically acceptable composition. The cosmetically acceptable composition of this invention may include one or more sunscreen active agents. Examples of sunscreen active agents include but are not limited to octyl methoxymynamate (ethylhexyl p-methoxycinnamate), octyloxybenzone salicylate (benzophenone-3), benzophenone-4, methyl anthranilate, dioxybenzone, aminobenzoic acid, amildimethyl PABA, diethanolamine p-methoxy cyanamate, ethyl 4-bis (hydroxypropyl) aminobenzoate, 2-ethylhexyl 1-2 cyano-3, 3-diphenylacrylate, homomenthyl salicylate, glyceryl aminobenzoate, dihydroxyacetone, octyl dimethyl PABA, 2-phenylbenzimidazole-5 acid -sulfonic, triethanolamine salicylate, zinc oxide and titanium oxide, and mixtures thereof. The amount of sunscreen used in the cosmetically acceptable composition of this invention will vary depending on one or more of the UV radiation absorption wavelengths specific to one or more of the specific sunscreen active ingredients used and may be 0.1 at 10 percent by weight, from 2 to 8 percent by weight. The cosmetically acceptable composition of this invention may include one or more preservatives. Examples of preservatives that may be used include, but are not limited to, 1,2-dibromo-2,4-dicyanobutane (Methyldibro or Glutaronitrile, known as MERGUARD ™, Ondeo Nalco Company, Naperville, IL, USA), benzyl alcohol , imidazolidinylurea, 1,3-bis (hydroxymethyl) -5,5-dimethyl-2,3-imidazolidinedione (for example DMDM hydantoin, known as GLYDANT ™, Lonza, Fairlawn, NJ, USA), methylchloroisothiazolinone and methylisothiazolinone (eg Kathon ™, Rohm &; Haas Co. , Philadelphia, PA, USA), methylparaben, propylparaben, phenoxyethanol and sodium benzoate, and mixtures thereof. The cosmetically acceptable composition of this invention may include any other ingredients commonly used in cosmetics. Examples of such ingredients include, but are not limited to, buffering agents, fragrance ingredients, chelating agents, color additives or dyeing materials which may serve to color the composition itself or the keratin, sequestering agents, softeners, synergistic agents. of foam, foam stabilizers, sunscreens and peptizing agents. The surface of the pigments such as titanium dioxide, zinc oxide, talcum, calcium carbonate or kaolin can be treated with the unsaturated quaternary ammonium compounds described herein and then used for the cosmetically acceptable composition of this invention. The treated pigments are then more effective as sunscreen active substances and for use in color cosmetics such as makeup and mascara. The cosmetically acceptable composition of this invention may be present in various forms. Examples of such forms include, but are not limited to a solution, liquid, cream, emulsion, dispersion, gel or thickening lotion. The cosmetically acceptable composition of this invention may contain water and also any cosmetically acceptable solvent. Examples of acceptable solvents include, but are not limited to monoalcohols such as alcandés having 1 to 8 carbon atoms (like ethanol, isopropanol, benzyl alcohol and phenylethyl alcohol), polialcoles such as alkylene (such as glycerol, ethylene glycol and propylene glycol), glycol teres such as mono-, di- and tri-ethylene glycol monoalkyl ethers, for example ethylene glycol monomethyl ether and diethylene glycol monomethyl ether, used alone in a mixture. These solvents can be present in proportions of up to 70% by weight, for example from 0.1 to 70 percent by weight, based on the weight of the total composition. The cosmetically acceptable composition of this invention can also be packaged as an aerosol, in which case it can be applied either in the form of an aerosol spray or in the form of an aerosol foam. As the propellant gas for these aerosols it is possible to use, in particular, dimethyl ether, carbon dioxide, nitrogen, nitrous oxide, air and volatile hydrocarbons such as butane, isobutane and propane. The cosmetically acceptable composition of this invention may also contain electrolytes such as aluminum chlorohydrate, alkali metal salts, for example sodium, potassium or lithium salts, these salts preferably being halides, such as chloride, bromide, and sulfate, or salts with organic acids such as acetates or lactates, and also salts of metalalcalinoterreo, preferably the carbonates, silicates, nitrates, acetates, gluconates, pantotenates and lactates of calcium, magnesium and strontium. In a preferred aspect, the cosmetically acceptable composition of this invention is selected from products for treating hair, including shampoos, sunscreens, conditioners, permanent waving, hair straighteners, hair whiteners, hair untangling lotion, styling g styling glass, foam spray, creams styling, styling waxes, styling lotions, mousses, gspray, ointments, preparations for coloring hair colors for temporary and permanent hair conditioners color, brighteners hair rinses hair , colored or non-colored, hair dyes, wavy sets for hair, permanent waves, curling, hair straighteners, hair styling aids, hair toners, hair accessories and oxidizing products, liquid sprays, styling waxes and balms. In another preferred aspect, the cosmetically acceptable composition is selected from skin care compositions including skin care products that are left on or rinsed off such as lotions., hand and body creams, liquid soaps, soap bars, bath oil bars, facial cleansers, aftershave lotions, shaving gels or shaving creams, mascara, eye gel, eye lotion body wash, deodorants, antiperspirants, tanning lotions, gels for after sun exposure, bubble baths, compositions for hand or mechanically washing dishes, and the like. In addition to the polymer, skin care compositions may include components conventionally used in skin care formulations. Such components include, for example: (a) humectants, (b) petrolatum or mineral oil, (c) fatty alcohols, (d) fatty ester emollients, (e) silicone oils or fluids and (f) preservatives. These components in general must be safe for application on human skin and must be compatible with the other components of the formulation. The selection of these components is generally within the skills of the technique. The skin care compositions may also contain other conventional additives used in cosmetic formulations for skin care. Such additives include cosmetic enhancers, fragrance oils, colorants and medicaments such as menthol and the like. The skin care compositions of this invention can be prepared either as oil in water, water in oil emulsions, triple emulsions or dispersions. Preferred oil-in-water emulsions are prepared by first forming an aqueous mixture of water-soluble components, for example unsaturated ammonium-quaternary compounds, the humectant, the water-soluble preservatives, followed by the addition of the water-insoluble components. Water-insoluble components include the emulsifier, water-insoluble preservatives, petrolatum component or mineral oil, fatty alcohol component, fatty ester emollient and silicone oil component. The mixing energy input will be high and will be maintained for a sufficient time to form a water-in-oil emulsion having a uniform appearance (indicating the presence of relatively small micelles in the emulsion). Preferred dispersions are generally prepared by forming an aqueous mixture of water-soluble components, followed by the addition of thickener with suspending power for water-insoluble materials. Compositions for treating hair include bath preparations such as bubble baths, soaps and oils, shampoos, conditioners, hair bleaches, hair coloring preparations, temporary and permanent hair colors, color conditioners, hair brighteners, color and non-coloring hair rinses, hair dyes, wavy sets for hair, permanent wavy, curly, hair straighteners, hair preparation, hair tonics, hair accessories and oxidizing products. Dispersion polymers can also be used in the styling of products that are left on such as gels, foams, liquid sprays, styling creams, styling waxes, ointments, balms and the like, alone or in combination with other polymers or structuring agents for the purpose to provide control and manageability of hair with a clean, natural and non-sticky feeling. The hair care compositions of this invention provide a slippery feel and can be easily rinsed from the hair due to the presence of the dispersion polymer, volatile silicones, other polymers, surfactants or other compounds that can alter the deposition of the material on the hair. hair. In the case of cleaning formulations such as shampoo for washing the hair, or a liquid hand soap, a shower gel for washing the skin, the compositions contain anionic surfactants, cationic, non-ionic, amphoteric zwitterionic typically in an amount of about 3 to about 50% by weight, preferably about 3 to about 20% by weight and their pH in general is in the range of about 3 to about 10. The preferred shampoos of this invention contain combinations of anionic surfactants with zwitterionic surfactants and / or amphoteric surfactants. Especially preferred shampoos contain from about 0 to about 16% alkyl sulfate active substances, from 0 to about 50% by weight ethoxylated alkyl sulfates and from 0 to about 50% by weight of optional surfactants which are selected from agents non-ionic, amphoteric and zwitterionic surfactants with at least 5% by weight of either alkyl sulfate, ethoxylated alkyl sulfate or a mixture thereof, and a total surfactant concentration of from about 10 by weight to about 25 percent. The hair washing shampoo may also contain other conditioning additives such as silicones and conditioning polymers typically used in shampoos. The Patent of E.U.A. No. 5,573,709 provides a list of non-volatile silicone conditioning agents that can be used in shampoos. The conditioning polymers for use in the present invention are included in the Cosmetic, Toiletries and Fragrance Associations (CTFA) dictionary. Specific examples include polyquaternials (eg polyquaternium-1 to polyquaternium-50), hydroxypropyltrimonguar chloride, hydroxypropyltrimonium starch chloride and polymetracrylamidopropyltrimonium chloride. Other preferred embodiments consist of the use in the form of a rinse lotion to be applied primarily before or after shampooing. These lotions are typically aqueous or aqueous-alcoholic solutions, emulsions, thickened lotions or gels. If the compositions are in the form of an emulsion, they can be non-ionic, anionic or cationic. Nonionic emulsions consist mainly of a mixture of oil and / or a fatty alcohol with a polyoxyethylenated alcohol such as stearyl alcohol or cetyl / stearyl polyethoxyethylenated and cationic surfactants which can be added to these compositions. Anionic emulsions are formed essentially from soap. If the compositions are in the form of a thickened lotion or a gel, they contain thickeners in the presence or absence of a solvent. The thickeners which can be used are especially resins, thickeners of acrylic acid available from B.F. Goodrich; xanthan gums; sodium alginates; gum arabic; cellulose derivatives and thickeners based on poly (ethylene oxide) and it is also possible to obtain thickeners by means of a mixture of polyethylene glycol stearate or distearate or by means of a mixture of a phosphoric acid ester and an amide. The concentration of the thickener is generally 0.05 to 15 weight percent. If the compositions are in the form of a styling lotion, a shaving lotion or a setting lotion, they generally comprise, in an aqueous, alcoholic or aqueous solution of an alcoholic, the amphiphilic polymers defined in the foregoing.
In the case of hair fixatives, the composition may also contain one or more additional hair setting polymers. When present, additional hair setting polymers are present in a total amount from about 0.25 to about 10 weight percent. The additional hair setting resin can be selected from the following group insofar as it is compatible with a given dispersion polymer: acrylamide copolymer, acrylamide / sodium acrylate copolymer, acrylate / ammonium methacrylate copolymer, an acrylate copolymer , an acrylic / acrylate copolymer, a copolymer of adipic acid / dimethylaminohydroxypropyl diethylenetriamine, adipic acid / epoxypropyl diethylenetriamine copolymer, allyl stearate / VA copolymer, aminoethylacrylate / acrylate phosphate copolymer, an ammonium acrylate copolymer, a copolymer of vinylammonium acetate / acrylate, an AMP / diacetoneacrylamide acrylate copolymer, an AMPD acrylate / diacetoneacrylamide copolymer, a copolymer of ethylene butyl ester / maleic anhydride, PVM / MA copolymer butyl ester, calcium / sodium copolymer of PVM / MA, corn starch copolymer / acrylamide / sodium acrylate, diethyl copolymer eno glycolamine / epichlorohydrin / piperazine, copolymer of dodecanedioic acid / cetearyl alcohol / glycol, PVM / MA ethyl ester copolymer, PVM / MA isopropyl ester copolymer, karaya gum, methacryloylethylbetaine / methacrylate copolymer, octylacrylamide copolymer / acrylate / butylaminoethylmethacrylate, octylacrylamide / acrylate copolymer, a phthalic anhydride / glycerin / glycidyl decanoate copolymer, a phthalic / trimellitic / glycol copolymer, polyacrylamide, polyacrylamidomethylpropanesulfonic acid, polybutylene terephthalate, polyethylacrylate, polyethylene, polyquaternium-1, polyquaternium 2, polyquaternium-4, polyquaternium-5, polyquaternium-6, polyquaternium-7, polyquaternium-8, polyquaternium-9, polyquaternium-10, polyquaternium-11, polyquaternium-12, polyquaternium-13, polyquaternium-14, polyquaternium-15, polyquaternium-39, polyquaternium-47, polyvinyl acetate, polyvinyl butyral, polyvinyl imidazolinium acetate, polyvinyl methyl ether, cop PVM / MA olimer, PVP, PVP / dimethylaminoethyl methacrylate copolymer, PVP / eicosene copolymer, PVP / ethyl methacrylate / methacrylic acid copolymer, PVP / hexadecene copolymer, PVP / VA copolymer, PVP / vinyl acetate copolymer / itaconic acid, shellac, sodium acrylate copolymer, sodium acrylate / acrylonitrile copolymer, sodium acrylate / vinyl alcohol copolymer, sodium carrageenan, diethylaminoethyl ether starch, ethersaryl vinyl ether / maleic anhydride copolymer, sucrose benzoate copolymer / acetate sucrose isobutyrate / butylbenzyl phthalate, sucrose benzoate copolymer / sucrose acetate isobutyrate / butylbenzylphthalate / methyl methacrylate, sucrose benzoate copolymer / sucrose acetate isobutyrate, a vinyl acetate / crotonate copolymer, copolymer vinyl acetate / crotonic acid, vinyl acetate / crotonic acid / methacryloxybenzophenone-1 copolymer, copolymer of vinyl acetate / crotonic acid / vinyl neodecanoate, and mixtures thereof. The synthetic polymers used to create the auxiliaries in the style are described in "The History of Polymers in Haircare" Cosmetics and Toiletries, 103 (1988), incorporated herein by reference. Other synthetic polymers that can be used in the present invention can be found as a reference in the CTFA dictionary, fifth edition, 2000, incorporated herein by reference. If the compositions of the present invention are intended to be used in the dyeing of keratin fiber, and in particular of human hair, they generally contain at least one precursor of dyeing oxidation material and / or a direct dyeing material, in addition to the unsaturated quaternary ammonium compounds. It also contains any other adjuvant normally used in this type of composition. The pH of the dyeing compositions is generally from 7 to 11 and can be adjusted to a desired value by adding an alkylating agent.
The compositions according to this invention can also be used for crimping or for straightening hair. In this case, the composition generally contains, in addition to these unsaturated quaternary ammonium compounds, one or more reducing agents and, if appropriate, other adjuvants normally used in this type of compositions; such compositions are designed for use in conjunction with a neutralizing composition. As discussed above, the novel polyaminoamides containing 1,3-diimine groups of this invention are also useful as ultraviolet absorbent agents for stabilizing a wide variety of materials including, for example, various polymers (cross-linked and thermoplastic), photographic materials and dyeing solutions for textile materials, as well as ultraviolet light filter agents. Polyaminoamides containing 1,3-diimine groups can be incorporated into said material in any of a variety of conventional ways including, for example, blended or physically combined, optionally with a chemical bond to the material (typically a polymer), such as a component in a light stabilizing composition such as a coating or solution, or as a component in a sunscreen composition for UV radiation. The polyaminoamides containing 1,3-diimine groups of this invention can be used to stabilize polymeric materials as well as a variety of both natural and synthetic organic materials which are subject to degradation by ultraviolet radiation by incorporation of the polyaminoamides containing groups 1, 3 -diimine in polymeric materials, either chemically or physically. Representative polymers which can be stabilized include, but are not limited to, polyolefins; polyesters; polyethers; polyketones; polyamides; natural and synthetic rubbers; polyurethanes; polystyrenes; high impact polystyrenes; polyacrylates; polymethacrylates; polyacetals; polyacrylonitriles; polybutadienes; polystyrenes; ABS; SAN (styrene acrylonitrile); ASA (styrene acrylonitrile acrylate); cellulose acetate butyrate; cellulosic polymers; polyimides; polyamidoimides; polyetherimides; polyphenyl sulfides; PPO; polysulfones; polyethersulfones; polyvinyl chloride; polycarbonates; polyketones; aliphatic polyketones; TPO thermoplastics; polyacrylates and polyesters cross-linked with aminoresin; polyesters and polyacrylates crosslinked with polyisocyanate; phenol / formaldehyde resins, urea / formaldehyde and melamine / formaldehyde; alkylating resins drying and not drying; alkylary resins; polyester resins; acrylate resins crosslinked with melamine resins, urea resins, isocyanates, isocyanurates, carbamates and epoxy resins; crosslinked epoxy resins derived from aliphatic, cycloaliphatic, heterocyclic and aromatic glyceryl compounds which are crosslinked with anhydrides or amines; polysiloxanes; Michael addition polymers of blocked amines or amines with activated unsaturated compounds and methylene, ketimines with activated unsaturated compounds and methylene, polyketimines in combination with unsaturated acrylic polyacetoacetate resins and polyketimines in combination with unsaturated acrylic resins; radiation curable compositions and epoxymelamine resins. The novel 1,3-diimine-containing polyaminoamides of this invention can be used in amounts that vary widely in such applications, which depend on things like the material to be stabilized and particular application. However, when used as a stabilizing additive for materials such as organic polymers, the polyaminoamide UV radiation absorbers of the present invention are typically used in amounts of from about 0.01 to about 20% by weight, preferably from about 0.1 to about 10% by weight and more preferably from about 0.1 to about 5% by weight, based on the weight of the material to be stabilized. In filtering applications, such sunscreen compositions, the polyaminoamide UV absorbers are used in the same relative amounts but are based on the total weight of the filtering agent. Polyaminoamides containing 1,3-diimine groups can also be added to the polymers to be stabilized in the form of a master batch which comprises these compounds, for example, in a concentration of about 2.5 to about 25%, so preferably from about 5 to about 20% by weight of the polymer. Polyaminoamides containing 1,3-diimine groups can be incorporated into the polymeric material by any of a large number of methods including those conventionally used in the art, including, for example: a) as an emulsion or dispersion (e.g. to reticles or emulsion polymers); (b) as a dry mixture during the mixing of additional components or polymer blends; (c) by direct addition to the processing equipment (for example extruders, internal mixers, etc); or (d) as a solution or cast. The incorporation can be effected efficiently before or during shaping, for example by mixing the powdery components or by adding the stabilizer to the melt or the polymer solution, by applying the dissolved or dispersed compounds to the polymer, with or without subsequent evaporation. of the solvent. Polymers incorporating the 1,3-diimine-containing polyaminoamide of this invention can be incorporated into articles of manufacture by any method conventional in the art including molding, extrusion and the like. The polyaminoamides containing 1,3-diimine groups of this invention are also suitable for photochemical stabilization of non-dyed, dyed or printed fiber materials including silk, leather, wool, polypropylene, polyester, polyethylene, polyolefins, polyamide or polyurethanes and especially fiber materials that contain cellulose of all kinds. Examples of such fiber materials are natural cellulose fibers such as cotton, linen, jute and hemp, and also short fibers of viscose and regenerated cellulose. The polyamides I are also suitable for the photochemical stabilization of hydroxyl-containing fibers in combined fabrics, for example combinations of cotton with polyester fibers or polyamide fibers. A further preferred application area relates to the blocking or reduction of UV radiation which passes through the aforementioned textiles (UV cut) and the increased sun protection which such textiles offer to human skin. A further preferred area includes applications in automobiles such as seat belts, head coverings, carpeting and upholstery. The polyaminoamide containing 1,3-diimine groups is applied to the textile fiber material by any of the usual dyeing methods, typically in an amount of 0. 01 to 5 percent by weight, based on the weight of the fiber material. The polyaminoamide containing 1,3-diimine groups can be applied to the fiber material in various ways and can be fixed to the fiber, especially in the form of aqueous dispersions or printing pastes. The textile fiber materials terminated with the polyaminoamide containing the 1,3-diimine group of this invention possesses an improved protection against photochemical fiber breakage and yellowing phenomenon and, in the case of dyed fiber material, are of a Improved resistance to light. Particular emphasis must be placed on the photoprotective effect greatly improved on the treated textile fiber material and, in particular, on the good protective effect with respect to short-wave UV-B rays. This is manifested by the fact that the textile fiber material finished with the polyaminoamide containing 1,3-diimine groups have a very high sun protection factor (SPF) in relation to the untreated fabric. The sun protection factor is defined as the quotient of the dose of UV radiation that damages the protected skin with respect to which it damages the unprotected skin. Accordingly, a sun protection factor is also a measure of the degree to which untreated fiber materials and fiber materials treated with the polyaminoamide containing 1,3-diimine groups are permeable to UV radiation. The determination of the sun protection factor of textile fiber materials is explained, for example, in WO94 / 04515 or in J. Soc. Cosmet. Chem. 40, 127-133 (1989) which can be carried out analogously thereto. The polyaminoamide containing 1,3-diimine groups of this invention can be used in coating compositions and can be applied to any desired substrate, for example to metal, wood, plastic, fiberglass or ceramic materials. The coating compositions can be pigmented as monocoats or as multi-layered systems (sizing / basecoat / clearcoat) typical of automotive finishes. The coating compositions can be applied to the substrates by the usual methods, for example, by brushing, spraying, pouring, inversion or electrophoresis; see also Ullmann's Encyclopedia of Industrial Chemistry, fifth edition, volume A18, pages 491-500. The polyaminoamide containing 1,3-diimine groups can also be applied topically by polishing a surface with a composition comprising the polyaminoamide containing the 1,3-diimine group and an inert carrier such as solvent, silicone oil or aqueous emulsions, or a car paint wax, for example carnauba wax. These topical treatment compositions can be used to stabilize coating films, fabrics, leather, vinyl and other plastics and wood. Mixtures comprising polyaminoamides containing 1,3-diimine groups of this invention can also be used as stabilizers for film-forming binders for coatings, for example, for paints as described, for example, in US Patent Nos. 4,619,956, 4,740,542, 4,826,978, 4,962,142, 5,106,891, 5,198,498, 5,298,067, 5,322,868, 5,354,794, 5,369,140, 5,420,204, 5,461,151 and 5,476,937, EP-0434608 and EP-A-0444323), particularly coatings and paints for the automotive industry. Such film-forming compositions typically comprise about 0.01 to about 20 weight percent of the polyaminoamide containing 1,3-diimine groups of this invention. The polyaminoamides containing 1,3-diimine groups of this invention can also be used for photosensitive materials of all kinds. For example, they can be used for color paper, reverse color paper, positive direct color material, negative color film, positive color film, color inversion film and other materials. Preferably they are used, for example, for photosensitive color material which comprises a reverse substrate or which forms positive. Polyaminoamides containing 1,3-diimine groups can be combined with other UV absorbers especially those which can be dispersed in aqueous gelatin, for example with hydroxyphenylbenzotriazoles (see, for example, US Patent Nos. 4,853,471, 4,973,702, 4,921,966 and 4,973,701), benzophenones, bisbenzophenones as described in US Pat. No. 6,537,670, oxanilides, cyanoacrylates, salicylates or acrylonitriles or thiazolines. In this context, it is advantageous to use these additional UV absorbers in the photographic material in layers different from those comprising the polyaminoamides containing 1,3-diimine groups. the polyaminoamides containing 1,3-diimine groups of this invention can also be used in cellulose-based paper formulations, for example in new printing, cards, posters, packaging, labels, advertisements, paper for books and magazines, typing paper bond, multipurpose and office paper, computer paper, xerographic paper, paper for laser and inkjet printer, offset paper, paper money, etc. The polyaminoamides containing 1,3-diimine groups of this invention are also suitable for ink stabilization. Based on the proposed final use, the polyaminoamides containing 1,3-diimine groups of this invention can be combined with one or more of a variety of additives conventionally used in the UV stabilization technique including antioxidants, ultraviolet light absorbers, ultraviolet light stabilizers, metal deactivators, phosphites, phosphonites, hydroxylamines, nitrones, thiosynergists, peroxide scavengers, polyamide stabilizers, nucleating agents, fillers, reinforcing agents, plasticizers, lubricants, emulsifiers, pigments, rheological additives, agents flame retardants, antistatic agents, blowing or expanding agents, benzofuranones and indolinones. The foregoing can be better understood with reference to the following examples which are presented for purposes of illustration and are not intended to limit the scope of this invention.
Example 1 Polyaminoamide of diethylenetriamine-DBE-2 dibasic ester containing 1,3-diimine groups. In a 1000 ml two-piece resin 5-neck reactor equipped with a mechanical stirrer, nitrogen purge, a temperature controller and a condenser are charged 208.0 g diethylenetriamine (DETA, 2.0 moles), 327 g (2.0 moles) of dibasic ester of DBE-2 and 5.0 g of sulfuric acid. The mixture is heated to 150 ° C and methanol is collected through a condenser. The temperature is increased to 180 ° C once there is no additional methanol extracted by distillation. The temperature is maintained at at least 180 ° C for several hours until approximately 15.0 g of water by-product is collected. The heating is then stopped and 395 g of water are slowly added to the reactor at a temperature below about 140 ° C to produce an aqueous polymer solution.
Example 2 Polyaminoamide of dibasic ester of dibasic diethylenetriaminadimethylterephthalate-DBE-2 containing 1,3-diimine groups. To a reactor as described in Example 1, 87.3 g (0.45 mol) of dimethyl terephthalate are charged and the reactor purged with nitrogen for 15 minutes. DETA (156.4 g, 1.5 mol), dibasic ester of DBE-2 and 5.0 g of sulfuric acid are charged to the reactor. The mixture is heated at 150 ° C for about 2 hours until methanol is no longer distilled off. Then the temperature is increased to 190 ° C. The temperature is maintained at 190 ° C or higher for several hours until about 15.0 g of the water by-product is collected. The heating is then stopped and 300 g of water is slowly added to the reactor at a temperature below about 140 ° C to produce an aqueous polymer solution.
Example 3 Polyaminoamide of dibasic methyl ester salicylate of diethylenetriaminadimethylterephthalate-DBE-2 containing 1,3-diimine groups. 58.3 g (0.3 moles) of dimethyl terephthalate are charged to a reactor as described in Example 1. The reactor is purged with nitrogen for 15 minutes. Charged in the DETA reactor (171.6 g, 1.65 mol), 196.2 g (1.2 mol) of dibasic ester of DBE-2 and 5.0 g of sulfuric acid. The mixture is heated to 150 ° C until no methanol is distilled off. 45.3 g (0.3 moles) of methyl salicylate are added to the reactor. The mixture is further heated to 150 ° C until methanol is not removed by distillation. The temperature is then increased to 190 ° C and maintained at 190 ° C or higher until approximately 15 g of water by-product is collected. The heating is then stopped and 300 g of water in the reactor is added very slowly to a temperature below about 140 ° C to produce an aqueous polymer solution.
Example 4 Polyaminoamide of diethylenetriamineadipic acid containing 1,3-diimine groups. To a reactor as described in example 1, 208.0 g (2.0 moles) of DETA and 292 g (2.0 moles) of adipic acid are charged. The mixture is heated to 160 ° C and water is collected through a condenser. The temperature is increased to 185 ° C after approximately 72.0 g of water (4.0 moles) are collected. The temperature is maintained at least at 185 ° C until approximately 15.0 g of water by-product are collected. The heating is then stopped and 410 g of water is slowly added to the reactor at a temperature below about 140 ° C to produce an aqueous polymer solution.
Example 5 Polyaminoamide of tetraethylenepentamineadipic acid containing 1,3-diimine groups. To a reactor as described in example 1 330.0 g (1.65 mol) of tetraethylenepentamine (TEPA) and 219.0 g (1.50 mol) of adipic acid are charged. The mixture is heated to 190 ° C and the by-product of water is collected through a condenser. The temperature is maintained at at least 190 ° C for several hours until 72.0 g (4.0 moles) or more of water byproduct are collected. The heating is then stopped and 410 g of water is slowly added to the reactor at a temperature below about 140 ° C to produce an aqueous polymer solution.
Example 6 Comparative example In this example, DETA is condensed with dibasic ester of DBE-2 or adipic acid using procedures similar to those described in examples 1-5, except for heating for the times and temperatures indicated in table 1. records the UV absorbance (measured in a 100 ppm polymer solution in a 1 cm cell and? ax = 313 nm) of the polymer after heating for 2 hours at 150 ° C. The polymer is then heated for an additional period at the temperatures shown in column 4 and the UV absorbance of the polymer is recorded again. Table 1 UV Absorbance and Synthetic Conditions of Polyamino Amides Containing 1,3-Diimine Groups Table 1 shows the emergence of UV absorbance after the preformed polymers at lower temperatures are heated at higher temperatures. Conventional polyaminoamides do not show a significant UV absorbance at 280-350 nm due to the lack of the 1,3-diimine structure, the existence of 1,3-diimine is easily identified by a strong 'UV absorbance at approximately 300 nm - 350 nm, due to the equilibrium of enamine-imine tautism. Example 7 Representative formulation of surfactant treatment A representative solution of surfactant test is shown in Table 2. The formulation is prepared by mixing water with sodium lauryl sulfate. The polymer is then added into the surfactant solution. The pH of the surfactant solution is adjusted to 5.0 +/- 0.2 with citric acid.
Table 2 Representative solution of surfactant test Example 8 Representative hair conditioner formulation. A representative sheet of a conditioning formulation for hair is shown in Table 3. The conditioner is prepared by dispersing Natrosol in water, adding polymer and mixing until uniform. Then they are added with mixed, after each addition, potassium chloride and cetrimonium chloride. The parabens are combined with glycerin and the mixture is stirred until uniform and then added to the batch. The Polysorbate 20 and any fragrance are combined, mixed until uniform and the mixture is added to the batch. Finally, the pH of the batch is adjusted to approximately 5.3.
Table 3 Representative conditioner formulation that is left on Example 9 Shampoo representative formulation. The ingredients shown in Table 4 are added to water in the sequence shown with mixing at a moderate mixing rate. Then the polymeric solar filter is added, the pH is adjusted to approximately 6 with citric acid (0.25-0.4% by weight) and sodium chloride is added with mixing to obtain the desired viscosity. Table 4 Representative Shampoo Example 10 Preparation of hair strands for testing. The experiments described herein were performed on 20 cm (eight inches) long Virgin / Blonde hair, available from International Hair Importers and Products Inc., Bellerose, New York. The hair of hair (1.5 g each), are grouped and moistened with water. One gram of sodium laureth sulfate is massaged into the hair from top to bottom for 1 minute. The hair locks are then rinsed under running water at 40 ° C for 1 minute, rinsed in deionized water overnight and air dried.
Example 11 Preparation of colored hair strands for testing. Brown-haired, bleached hair of average length of 20 cm (8 inches) is used from International Hair Importers and Products Inc., Bellerose, New York. The hair is dyed reddish brown using a level 3 commercial dyeing equipment from L'Oreal. The dyeing procedures follow the instructions of the dyeing equipment.
Example 12 UV irradiation. Before the exposure with UV irradiation, the hair strands are treated with formulations of the examples shown in the above, for 5 minutes and then rinse under deionized water for 30 seconds. The treated hair is air dried. The treatment is repeated three times. After treatment, the hair strands will detach from the set and disperse in sample holders, in a single layer. Samples are placed 10 cm apart from UV bulbs and exposed to simulated half-day summer sunlight on the Q-Panel Accelerated Weathering Tester (Q-Panel Lab Products, 26200 First Street Cleveland, OH 44145) at 45 ° C and 30% relative humidity for 400 to 600 hours.
Example 13 Colorimetric measurement. The hair samples collected from the UV environment exposure test are grouped. The colorimeter (LabScan XE, HunterLab, Reston, VA) is standardized before the test. A hair set is placed on the top of the scan port and the hair samples are read. The values of three Hunter, L, a and b stimuli are measured by using the Hunter Colorimeter LabScan XE instrument. The data presented, in terms of total color difference,? E = ~ (9? 12 +? A2 +? B2) and the chromaticity difference? C = ^ f (? A2 +? B2) between the exposed and non-exposed sections exposed hair hair under UV irradiation are the average of measurements made in various positions. The coloring index is calculated as Cl =? E /? C.
Example 14 Test of tensile strength. The tensile strength of the hair is a direct reflection of the degree of photonic damage to the hair. The resistance of the hair can be measured using a suitable traction determination instrument. Individual hairs are placed in a work assembly and pulled at a fixed speed until break occurs. A load is applied under computer control and the extension against load is recorded for each hair. Using measured hair diameters and a fixed calibrated length, this data can be converted to the total amount of work needed to break the hair fiber. The instrument used to measure the tensile strength of the hair is DiaStron Miniature Tensile Testers 170/670 (DiaStron limited Hampshire, United Kingdom).
Example 15 Analysis of FT-IR. FTIR is used to determine the degree of UV damage to the hair. Damage by UV radiation can be observed via the SO band as a result of oxidation of the S-S bond in cysteine or cystine. By taking the proportion in band of SO and the amide band that is located in (1041 cm "1) at different points in time, one can measure quantitatively the increase in the intensity of the SO band.The intensity of the SO band is directly proportional to the duration of UV exposure at the first 800 hours, reaching a plateau between 800 and 1200 hours of exposure.The study has shown that the FTIR method is a viable technique to quantitatively measure the relative change of the SO band. The FT-IR study is performed by pressing virgin hair on a single reflectance cell with a presser along the same axis as the beam path, scanning the hair 128 times using a Nicolet Avatar 360 FTIR device. used is DTGS.The spectrum collected is designated as exposure at 0 hours.The subsequent FTIR analysis is performed on the hair in the same way after exposure to UV radiation during 400, 800 and 12 00 hours The peak height of the SO band at 1041 cm "1 is measured and compared with the band I amide (1633 cm "1) A higher peak ratio means more hair oxidation damaged by UV radiation, each hair is analyzed in triplicate to obtain an average value.
Example 16 Demonstration of hair coloring deduction. In order to demonstrate the effectiveness of polymers that absorb UV radiation in reducing hair coloration after exposure to UV radiation, quantitative changes in the total color difference between exposed and unexposed hair and between scalps are measured treated with a representative UV absorbing polymer of this invention and hair treated with a comparative product using polyquaternium 59 and butylene (Comparative Solar Filter A). The results are shown in Tables 5 and 6 for hair treated with the formulations of Examples 7 and 8, respectively.
Table 5 Measurement of the coloring index As shown in Table 5, the polymeric sunscreens prepared using the UV absorbing polymers of this invention show a much smaller total color difference (ΔE) compared to an untreated hair sample. The result indicates that the polymeric sunscreens of this invention provide superior protection to hair by preventing color change after exposure to UV radiation.
Table 6 Measurement of coloring index As shown in Table 6, a conditioner formulated with a representative polymer solar filter of this invention provides better protection against the sun compared to the comparative sunscreen A, as becomes evident by the lower overall color change in the hair hair treated with conditioner.
Example 17 Demonstration of the hair coloring deduction for dyed hair. The quantitative changes in the total color difference of hair dyed between 'exposed and unexposed hair and hair treated with a representative UV-absorbing polymer of this invention and with comparative products, particularly polyquaternium 59 and butylene, are measured. (comparative solar filter A), a commercial product Biolage ™ and Clariol Hydrience ™. The results are shown in Table 7.
Table 7 Measurement of total color change for dyed hair In Table 7, commercial products for protection of disappearance of hair color are used as reference values. The results presented in Table 7 clearly indicate that the hair dyed manually treated with the polymeric solar filter show a value? And much lower compared to the comparative sunscreen A and commercial products, which means that the polymeric sunscreen provides better protection to the removal of color for the dyeing of artificial hair.
Example 18 Results of tensile strength. The resistance to breakage of fibers alone directly reflects the degree of damage to the hair caused by sunlight. The greater the force that is required to break a single fiber, the less damage the hair fiber will experience. The following table summarizes the test results of the single fiber analysis which uses 70 pieces of hair fibers for each study in order to generate statistically adequate data. Table 8 Analysis of tensile strength As shown in Table 8, the polymeric sunscreens 1 and 2 show a significantly higher breaking force compared to the comparative sunscreen A. The results also show that the polymeric sunscreens 1 and 2 provide better sun protection in the sun. comparison with the control (damaged) and with the reference values. Example 19 FT-IR analysis. Oxidation of the disulphide bond is an indication of the degree to which the hair keratin is degraded.
The FT-IR analysis measures the absorbance of the S-0 bond using amide of the hair protein as an internal standard. The results (Tables 9 and 10) show that the hair locks protected by the polymeric sunscreens of this invention have lower SO / amide ratios compared to the comparative sunscreen A and the control. Two sets of hair strands treated with conditioning formulation are tested for duplicity. The results shown in Tables 9 and 10 confirm that the polymeric sunscreen of this invention works better than the control and comparative sunscreen A. Table 9 FT-IR Analysis Table 10 FT-IR analysis Changes can be made in the composition, operation and distribution of the method of the invention described herein without departing from the concept and scope of the invention as defined in the claims. It is noted that in relation to this date, the best method known to the applicant to carry out the aforementioned invention, is that which is clear from the present description of the invention.

Claims (20)

CLAIMS Having described the invention as above, the content of the following claims is claimed as property:
1. A composition for protecting a substrate from the effect of ultraviolet light, characterized in that it comprises an effective protective amount of UV radiation, of one or more water-soluble polyaminoamides containing 1,3-diimine groups, wherein the polyaminoamides containing 1,3-groups -diimine absorb ultraviolet light radiation having a wavelength of about 200 nm to about 420 nm.
2. The composition according to claim 1, characterized in that the polyaminoamides containing 1,3-diimine groups absorb UV radiation having a wavelength of about 280 nm to about 350 nm.
3. The composition according to claim 1, characterized in that the polyaminoamide containing 1,3-diimine groups further comprises 1 or more additional UV-absorbing portions.
4. The composition according to claim 3, characterized in that the additional UV-absorbing portions are selected from the substituted and unsubstituted forms of cinnamoyl, salicyloyl and p-dialkylaminobenzoyl.
The composition according to claim 1, characterized in that the polyaminoamide containing 1,3-diimine groups is cross-linked with one or more cross-linking agents.
6. The cross-linked polyaminoamide containing 1,3-diimine groups, according to claim 5, characterized in that the crosslinking agents are selected from the group consisting of diepoxides, dianhydrides, dihalogen derivatives, diesters, diacids, epihalohydrins or oligomers of epihalohydrin /amine.
7. The crosslinked polyaminoamide containing 1,3-diimine groups, according to claim 6, characterized in that the crosslinking agent is selected from the group consisting of poly (ethylene glycol) diglycidyl ether, poly (propylene glycol) diglycidyl ether, epichlorohydrin, epichlorohydrin oligomers / dimethylamine.
8. A modified polyaminoamide characterized in that it contains 1,3-diimine groups prepared by reacting a polyaminoamide containing 1,3-diimine groups according to claim 1, with one or more modifiers that are selected from the group consisting of the containing cationic functional groups, portions containing anionic functional groups and portions containing substituted and unsubstituted aliphatic hydrocarbons.
9. The modified polyaminoamide containing 1,3-diimine groups, according to claim 8, characterized in that the portion containing cationic functional groups is selected from glycidyltrimethylammonium chloride and N- (3-chloro-2-hydroxypropyl) chloride. trimethylammonium.
10. The modified polyaminoamide containing 1,3-diimine groups, according to claim 8, characterized in that the portion containing anionic functional groups is selected from chloroacetic acid and salts thereof, 1,3-propanesultone, 1, 4 -Butanosultone.
11. The modified polyaminoamide containing 1,3-diimine groups, according to claim 8, characterized in that the portion containing aliphatic hydrocarbon groups is selected from the group consisting of glycidyl ethers of aliphatic alcohols of 6 to 18 carbon atoms .
12. The composition according to claim 1, characterized in that it also comprises one or more cosmetically acceptable excipients.
The composition according to claim 12, characterized in that the excipients are selected from the group consisting of saccharides, surfactants, humectants, petrolatum, mineral oil, fatty alcohols, fatty ester emollients, waxes and waxes containing silicone, oil silicone, silicone fluid, silicone surfactants, volatile hydrocarbon oils, quaternary nitrogen compounds, silicones with amine functionality, conditioning polymers, rehology modifiers, antioxidants, sunscreen active agents, long chain diamines of approximately 10 to 22 carbon atoms, long chain fatty amines of approximately 10 to 22 carbon atoms, fatty alcohols , ethoxylated fatty alcohols and dicola phospholipids.
14. The composition according to claim 12, characterized in that it is selected from the group consisting of shampoos, sunscreens, conditioners, permanent wavy, hair straighteners, hair whiteners, hair untangling lotion, styling gel, styling glasses , spray foams, styling creams, styling waxes, styling lotions, foams, spray gels, ointments, hair coloring preparations, temporary and permanent hair colors, color conditioners, hair lighteners, dyes and hair rinses without dye, hair dyes, sets of wavy hair, permanent waves, curly hair, hair straighteners, auxiliary to fix the hair, hair tonic, hair accessories and oxidizing products, liquid spray, waxes for styling and balsams.
15. The composition according to claim 12, characterized in that it is selected from the group consisting of lotions, hand and body creams, liquid soaps, bar soaps, bath oil bars, facial cleansers, lotions for after shaving, shaving gels, shaving creams, mascara, eye gel, eye lotion, body washes, deodorants, antiperspirants, sunscreens, tanning lotions, gels to be used after sun exposure, bubble baths and compositions for washing both manual and mechanical frets.
16. A method of protecting a substrate from the effects of ultraviolet light characterized in that it comprises applying to the substrate an effective ultraviolet light protecting amount of the polyaminoamide containing 1,3-diimine groups according to claim 1.
17. The method according to claim 16, characterized in that the substrate is a keratin substrate.
18. The method according to claim 17, characterized in that the keratin substrate is skin.
19. The method according to claim 17, characterized in that the keratin substrate is hair. The method according to claim 16, characterized in that the substrate is selected from the group consisting of materials of textile fibers, metal, wood, ceramic materials, plastics and paint.
MXPA/A/2006/004640A 2003-10-30 2006-04-26 Water-soluble polyaminoamides comprising 1,3-diimines as sunscreen agents MXPA06004640A (en)

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