DK163478B - Cosmetic Hair Care Containing A Cationic Polymer - Google Patents
Cosmetic Hair Care Containing A Cationic Polymer Download PDFInfo
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- DK163478B DK163478B DK350875A DK350875A DK163478B DK 163478 B DK163478 B DK 163478B DK 350875 A DK350875 A DK 350875A DK 350875 A DK350875 A DK 350875A DK 163478 B DK163478 B DK 163478B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
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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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
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- 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
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
- A61K2800/5426—Polymers characterized by specific structures/properties characterized by the charge cationic
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Description
iin
DK 163478BDK 163478B
Den foreliggende opfindelse angår et hårplejemiddel til opnåelse af forøget glans og blødhed samt lettere frisering af håret, hvilket middel omfatter 5 (1) en kationisk. polymer filmdanner med en molekylvægt mellem 500 og 15.000 og bestående af gentagelsesenheder med formlen - A - Z - (I) 10 hvori A betegner en gruppe indeholdende aminogrupper, og Z betegner en eller to divalente grupper valgt blandt usub-stituerede alkylengrupper og a 1ky1engrupper, der er substitueret med en eller flere hydroxy 1 grupper, af hvilke divalente 15 grupper mindst én er afbrudt af et eller flere nitrogenatomer, (2) et kvaternært ammoniumsalt af en polymer bestående af gentagelsesenheder med formlen (I), eller 20 (3) en polymer bestående af gentagelsesenheder med formlen (I), hvori aminogruppen er oxideret til dannelse af en ami-noxidgruppe.BACKGROUND OF THE INVENTION The present invention relates to a hair care agent to provide enhanced shine and softness and to easier hair styling, comprising 5 (1) a cationic. polymeric film having a molecular weight between 500 and 15,000 and consisting of repeating units of formula - A - Z - (I) 10 wherein A represents a group containing amino groups and Z represents one or two divalent groups selected from unsubstituted alkylene groups and α 1 alkylene groups, substituted by one or more hydroxy 1 groups, of which divalent groups at least one is interrupted by one or more nitrogen atoms, (2) a quaternary ammonium salt of a polymer consisting of repeat units of formula (I), or 20 (3) a polymer comprising repeating units of formula (I) wherein the amino group is oxidized to form an amine oxide group.
Fra dansk fremlæggelsesskrift nr. 134.141 kendes et hårpleje-25 middel indeholdende polymere, kationiske filmdannere med den almene formel -A-Z-A-Z-A-Z- (I) 30 i hvilken A betegner ^en gruppe med to aminfunktioner, fortrinsvis gruppen -N N-, og Z betegner symbolet B eller B', \_/ hvor B og B', som er ens eller forskellige, betegner en divalent gruppe, som er en alky1engruppe med lige eller forgrenet kæde indeholdende indtil 7 carbonatomer i hovedkæden, og som 35 er usubstitueret eller substitueret med én eller flere hydro-xylgrupper og endvidere kan indeholde oxygen-, nitrogen- og svovlatomer, 1-3 aromatiske og/eller heterocykli ske ringe.From Danish Patent Specification No. 134,141, a hair care agent containing polymeric cationic film formers of the general formula -AZAZAZ- (I) 30 is known in which A represents ^ a group of two amine functions, preferably the group -N N-, and Z represents the symbol B or B ', where B and B', which are the same or different, denote a divalent group which is a straight or branched chain alkyl group containing up to 7 carbon atoms in the main chain and which is unsubstituted or substituted by one or more hydroxyl groups and may further contain oxygen, nitrogen and sulfur atoms, 1-3 aromatic and / or heterocyclic rings.
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idet oxygen-, nitrogen- og svovl atomerne er til stede i form af ether-, thioether-, sulfoxid-, sulfon-, sulfonium-, amin-, alkylamin-, alkenylamin-, benzylamin-, aminoxid-, amid-, imid-, alkohol-, estei— og/eller urethangrupper.the oxygen, nitrogen and sulfur atoms being present in the form of ether, thioether, sulfoxide, sulfone, sulfonium, amine, alkylamine, alkenylamine, benzylamine, amine oxide, amide, imide, , alcohol, estei and / or urethane groups.
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De kendte hårplejemidler kan endvidere indeholde kvaternære ammoniumsalte samt oxidationsproduktet af en polymer med ovennævnte formel .The known hair care agents may further contain quaternary ammonium salts as well as the oxidation product of a polymer of the above formula.
10 Anvendelsen af disse polymere gør det muligt at begrænse eller modificere ulemperne, som resulterer af almentilstanden eller af sensibiliserende behandlinger, såsom affarvninger, perma-nentninger eller farvninger.The use of these polymers makes it possible to limit or modify the disadvantages that result from the general state or from sensitizing treatments, such as decolorization, permeability or staining.
15 Hårplejemidlet ifølge den foreliggende opfindelse er ejendom meligt ved, at A betegner enten gruppen: - N N - V_/ 20 eller en blanding af grupperne: / \ ©ΛΛ -N ,N - og -N N- \_y iv-/ ch2 25 COOØ eller de grupper, der dannes ved kvaternisering, og Z betegner enten gruppen B* eller Bl', og herunder mindst én gang Bl' eller den gruppe, der dannes ved beatinisering eller kvater- 30 nisering af Bl* eller blandingen af disse grupper, hvor Bl' er en divalent gruppe, som er en alky1engruppe med lige eller forgrenet kæde indeholdende indtil 7 carbonatomer i hovedkæden, hvilken gruppe er usubstitueret eller substitueret med en eller flere hydroxylgrupper og afbrudt af et eller flere ni- 35 trogenatomer, som er substitueret med en alkylkæde indeholdende fordelagtigt 1-4 og fortrinsvis 4 carbonatomer, idet alkyl-kæden eventuelt er afbrudt af et oxygenatom og obligatorisk 3The hair care agent of the present invention is property in that A denotes either the group: - NN - V_ / 20 or a mixture of the groups: / N-N, N - and -N N- \ -y iv- / ch 2 COOE or the groups formed by quaternization, and Z represents either the group B * or B1 ', and including at least once B1' or the group formed by beatinization or quaternization of B1 or the mixture of these groups, wherein B1 is a divalent group which is a straight or branched chain alkylene group containing up to 7 carbon atoms in the main chain which is unsubstituted or substituted by one or more hydroxyl groups and interrupted by one or more nitrogen atoms substituted by an alkyl chain advantageously containing 1-4 and preferably 4 carbon atoms, the alkyl chain being optionally interrupted by an oxygen atom and mandatory 3
DK 163478 BDK 163478 B
bærer en eller flere hydroxyl- eller carboxyl funktioner, og Bl betegner en divalent gruppe, som er en alkylengruppe med lige eller forgrenet kæde indeholdende indtil 7 carbonatomer i hovedkæden, der er substitueret med en hydroxy 1 gruppe og for-5 trinsvis en 2-hydroxypropen-l,3-diylgruppe.carries one or more hydroxyl or carboxyl functions, and B1 represents a divalent group which is a straight or branched chain alkylene group containing up to 7 carbon atoms in the main chain substituted with a hydroxy 1 group and preferably a 2-hydroxypropylene -l, 3-diyl group.
Disse polymerer udviser, ligesom de fra ovennævnte fremlæggelsesskrift kendte polymerer, egenskaber, som gør dem egnede til pleje og konditionering af håret. Foruden konditi oner ingsfor-10 dele, såsom forbedret udredning af fugtigt hår, forbedret glans, forbedret blødhed og lettere hårsætning, har polymererne, der anvendes i hårpiejerni diet, ifølge den foreliggende opfindelse imidlertid en forbedret forligelighed med overfladeaktive stoffer, som sædvanligvis benyttes i hårplejemidler, 15 især overfor an i on i ske overf 1adeaktive stoffer.These polymers, like the polymers known from the above disclosure, exhibit properties which make them suitable for care and conditioning of the hair. However, in addition to conditioning benefits, such as improved moisturizing, improved gloss, improved softness and light hair, the polymers used in hair care diets, according to the present invention, have improved compatibility with surfactants commonly used in hair care products. , 15 especially against an in on in surfactants.
Forskellen mellem de polymerer, der anvendes i de fra dansk fremlæggelsesskrift nr. 134.141 kendte hårplejemidler, og polymererne, der anvendes i hårplejemidlerne ifølge opfindelsen, 20 består i, at den i hårplejemidlerne ifølge opfindelsen indeholdte kationiske polymer altid omfatter gruppen βΐ', og ingen af de grupper (A,B og B'), der indgår i den i de nævnte kendte hårplejemidler indeholdte polymer, er lig med gruppen Bl'.The difference between the polymers used in the hair care agents known from Danish Patent Specification No. 134,141 and the polymers used in the hair care agents of the invention consists in the fact that the cationic polymer contained in the hair care agents of the invention always comprises the group βΐ and none of the the groups (A, B and B ') included in the polymer contained in said known hair care agents are equal to the group B1.
25 Bl' er en alkylengruppe, som er usubsti tueret eller er substitueret med en eller flere hydroxy 1 grupper samt afbrudt af et eller flere nitrogenatomer, idet nævnte nitrogenatomer er substituerede med en alkylgruppe, der eventuelt er afbrudt af et oxygenatom og skal indeholde en eller flere hydroxyl- og/eller 30 carboxyl grupper. Dette betyder, at B1' betegner en alkylengruppe, der er afbrudt af mindst et nitrogenatom, som er substitueret med en alkylgruppe, der skal indeholde en eller flere hydroxyl- og/eller carboxyl grupper. I polymererne, kendt fra det nævnte fremlæggelsesskrift, kan nitrogenatomet, der 35 kan afbryde alkylenkæden i gruppen B eller B', være substitueret med en alkylgruppe, men ikke med en alkylgruppe, der skal indeholde en eller flere hydroxyl- og/eller carboxy1 grupper.B 1 'is an alkylene group which is unsubstituted or substituted by one or more hydroxy 1 groups and is interrupted by one or more nitrogen atoms, said nitrogen atoms being substituted by an alkyl group optionally interrupted by an oxygen atom and containing one or more several hydroxyl and / or carboxyl groups. This means that B1 'represents an alkylene group interrupted by at least one nitrogen atom substituted by an alkyl group which must contain one or more hydroxyl and / or carboxyl groups. In the polymers known from said disclosure, the nitrogen atom capable of interrupting the alkylene chain of group B or B 'may be substituted by an alkyl group but not by an alkyl group containing one or more hydroxyl and / or carboxy groups.
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Som følge af tilstedeværelsen af gruppen B*’ har den i hårplejemidlerne ifølge opfindelsen indeholdte kation i ske polymer forbedrede egenskaber i forhold til de kendte polymerer og har specielt forbedret forligelighed med an i on i ske overfladeaktive 5 midler.Due to the presence of the group B * ', the cation contained in the hair care agents according to the invention has improved properties over the known polymers and has especially improved compatibility with other surfactants.
Målingen af denne forbedrede forligelighed foretages på følgende måde.The measurement of this improved compatibility is done as follows.
10 Man fremstiller en opløsning I indeholdende 3,5 g polymer og 125 g af en 40% laurylsulfatopløsning af tri ethanolamin, og man fylder op til 250 g ved tilsætning af destilleret vand.A solution I containing 3.5 g of polymer and 125 g of a 40% lauryl sulfate solution of tri-ethanolamine is prepared, and up to 250 g is made up by the addition of distilled water.
Man udtager 25 g af denne opløsning I og tilsætter dråbevis en 15 10% opløsning af natriumchlorid i vand indtil fremkomst af en uklarhed.25 g of this solution I are taken and a 10% solution of sodium chloride in water is added dropwise, until a cloudiness occurs.
Man noterer derefter antallet af tilsatte ml natriumchloridopløsning. Jo større denne mængde er, jo større er polymerens 20 forligelighed med det anioniske overfladeaktive middel.The number of ml of sodium chloride solution added is then noted. The greater this amount, the greater the compatibility of the polymer 20 with the anionic surfactant.
Som kontrol forbi ndel se anvendes forbindelsen ifølge eksempel 1 i dansk fremlæggelsesskrift nr. 134.141, hvilken forbindelse er den foretrukne forbindelse (og den mest benyttede i udfø-25 relseseksemplerne).As a control example, the compound of Example 1 is used in Danish Patent Specification No. 134,141, which compound is the preferred compound (and the one most commonly used in the embodiments).
Med denne kendte forbindelse har man sammenlignet forbindelserne ifølge de efterfølgende eksempler 3, 6 og 7.With this known compound, the compounds of the following Examples 3, 6 and 7 have been compared.
30 De ved sammenligningen opnåede resultater fremgår af nedenstående tabel .30 The results obtained by comparison are shown in the table below.
Måling af forligeligheden med anionisk overfladeaktivt middel.Measurement of compatibility with anionic surfactant.
35 535 5
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Forbindelse ml tilsat NaC1-op 1øsningCompound ml added NaCl solution
Forbindelse ifølge eksempel 1 i fremlæggelsesskrift 5 nr. 134.141 (kontrolforbindelse) 4,1Compound of Example 1 of Presentation 5 No. 134,141 (control compound) 4.1
Forbindelser indeholdt i hårplejemidlet ifølge opf i ndel sen: 10 Forbindelse ifølge eks. 3 20Compounds contained in the hair care agent of the invention: Compound of Example 3 20
Forbindelse ifølge eks. 6 17Compound of Example 6 17
Forbindelse ifølge eks. 7 15 15Compound of Example 7 15 15
Disse sammenligningsforsøg viser, at forbindelserne indeholdt i hårplejemidlet ifølge opfindelsen har en forligelighed med anioniske overfladeaktive midler, der er fire til fem gange så stor som den forligelighed, foretrukne forbindelser omhandlet 20. i fremlæggelsesskrift nr. 134.141 udviser.These comparative tests show that the compounds contained in the hair care agent of the invention have a compatibility with anionic surfactants which is four to five times as high as the compatibility preferred compounds of 20 in presentation specification No. 134,141.
Det kosmetiske hårplejemiddel kan endvidere indeholde oxidationsproduktet af en polymer bestående af gentagelsesenheder med formlen I, der fortrinsvis er opnået ved hjælp af hydro-25 genperoxid eller ved hjælp af en persyre, eller det kvaternære ammoniumsalt af en polymer bestående af gentagelsesenheder med formlen I.The cosmetic hair care agent may further contain the oxidation product of a polymer consisting of repeating units of formula I, preferably obtained by hydrogen peroxide or by a peracid, or the quaternary ammonium salt of a polymer consisting of repeating units of formula I.
Det har endvidere vist sig, at kosmetiske hårplejemidler inde-30 holdende en polymer bestående af gentagelsesenheder med formlen - A - Z - (I) kan forbedres ved anvendelse af kvaternære ammoniumsalte af de 35 nævnte polymere opnået ved kvaterniseri ng af de basiske grupper med ch1oreddikesyre eller et chloracetat, f.eks. natrium-chloracetat.Furthermore, it has been found that cosmetic hair care agents containing a polymer consisting of repeating units of formula - A - Z - (I) can be improved by using quaternary ammonium salts of the said polymers obtained by quaternizing the basic groups with chloroacetic acid or a chloroacetate, e.g. sodium chloroacetate.
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Det har vist sig, at forligeligheden af de således kvaternise-rede polymerer er forbedret overfor de anioniske overfladeaktive stoffer, som sædvanligvis benyttes i de nævnte hårplejemidler.It has been found that the compatibility of the thus quaternized polymers has improved with the anionic surfactants commonly used in said hair care agents.
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De foretrukne polymerer til anvendelse i hårplejemidlet ifølge opfindelsen er navnlig polymerer bestående af gentagelsesenheder med formlen - A - Z - (I) 10 ,__ / \ hvor A betegner gruppen - N N, og Z betegner B* eller B* og mindst én gang betegner gruppen Bl', herunder polymerer bestående af gentagelsesenheder med formlen (I), hvor nitrogenatomet i B11 er substitueret med en carboxymethy 1 gruppe, en 2—/5 — 15 hydroxyethoxyethylgruppe, en 1,3dihydroxy-2-methy1-2-propyl-gruppe eller en l-hydroxy-2-methyl-2-propylgruppe.In particular, the preferred polymers for use in the hair care agent of the invention are polymers consisting of repeating units of the formula - A - Z - (I) 10, where A represents the group - NN and Z represents B * or B * and at least once represents group B1, including polymers consisting of repeating units of formula (I), wherein the nitrogen atom of B11 is substituted by a carboxymethyl group, a 2-5-15 hydroxyethoxyethyl group, a 1,3 dihydroxy-2-methyl-2-propyl group or a 1-hydroxy-2-methyl-2-propyl group.
De kation i ske polymerer indeholdt i hårplejemidlet ifølge opfindelsen kan fremstilles ved direkte eller indirekte polykon-20 densation.The cation in spherical polymers contained in the hair care agent of the invention can be prepared by direct or indirect polycondensation.
Den direkte polykondensation består i at omsætte piperazin og en hydroxyleret amin, såsom diglycolamin eller 2-amino-2-me-thy1-propan-1,3-diol, eller en aminosyre, såsom aminoeddikesy-25 re, med en epihalogenhydrin, såsom epichlorhydrin eller epi -bromhydri n, i vandigt medium under til sætning af natrium til optagelse af den frigjorte hydrogensyre, hvorefter der opvarmes til en temperatur mellem 80 og 90°C.The direct polycondensation consists of reacting piperazine and a hydroxylated amine such as diglycolamine or 2-amino-2-methyl-1-propane-1,3-diol, or an amino acid such as aminoacetic acid with an epihalohydrin such as epichlorohydrin or epi -bromohydri n, in aqueous medium, under addition of sodium to take up the released hydrogen acid, and then heated to a temperature between 80 and 90 ° C.
30 Den indirekte polykondensation består i til at begynde med at fremstille et mellemprodukt X, som opnås ved omsætning af epihalogenhydrin med enten piperazin, den hydroxy1erede amin og/eller aminosyren. Dette mellemprodukt X bringes derpå til omsætning med en anden amin. Man tilsætter derpå eventuelt 3 5 epi halogenhydri nen, til sætter en base, såsom natri umhydroxid, og varmer til en temperatur mellem 80 og 90°C.The indirect polycondensation consists initially of preparing an intermediate X, which is obtained by reaction of epihalogen hydrin with either piperazine, the hydroxylated amine and / or amino acid. This intermediate X is then reacted with another amine. Optionally, the epi halo hydrogen is added, a base such as sodium hydroxide added, and heated to a temperature between 80 and 90 ° C.
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De anvendelige mængder piperazin, epihalogenhydrin og hydroxy-leret amin og/eller aminosyre afhænger af den rækkefølge af temaet Af B* og B*', som man ønsker at opnå i den endelige po1 ymer.The usable amounts of piperazine, epihalohydrin and hydroxylated amine and / or amino acid depend on the order of the theme of B * and B * 'which one wishes to obtain in the final polymer.
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Epihalogenhydrinen og blandingen af piperazin, hydroxyleret amin og/eller aminosyre er fortrinsvis til stede i ækvimolære mængder. Med hensyn til blandingen piperazin-hydroxyleret amin og/eller aminosyre omfatter denne molære mængder indeholdende 10 mellem 90 og 50¾ piperazin og 10 til 50% hydroxyleret amin og/eller aminosyre.The epihalohydrin and the mixture of piperazine, hydroxylated amine and / or amino acid are preferably present in equimolar amounts. For the mixture piperazine-hydroxylated amine and / or amino acid, this molar amount containing 10 contains between 90 and 50¾ piperazine and 10 to 50% hydroxylated amine and / or amino acid.
De således opnåede polymerer kan på kendt måde, således som anført i ovennævnte danske fremlæggelsesskrift, oxideres med 15 hydrogenperoxid eller persyrer eller kvaterniseres med kendte kvaterniseringsmidler, såsom lavere alkylbromid, -chlorid, -jodid, -sulfat, -mesylat eller -tosylat, fortrinsvis methyl-eller ethylforbindelsen, eller benzylchlorid eller benzy1 -bromid.The polymers thus obtained can be oxidized by hydrogen peroxide or peracids, or as quaternized with known quaternizing agents, such as lower alkyl bromide, chloride, iodide, sulfate, mesylate or tosylate, preferably methyl, as described in the aforementioned Danish publication specification. -or the ethyl compound, or benzyl chloride or benzyl bromide.
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En kvaternisering, som har vist sig særlig fordelagtig i henseende til den resulterende polymers forligelighed overfor anioniske overfladeaktive stoffer, er "betaini sering" af forbindelserne med formlen I, som består i kvaternisering af 25 0-66% af de basiske, kvaterniserbare grupper med natrium- chloracetat eller ch1oreddikesyre. Udbyttet ved omsætningen er generelt mellem 60 og 100%.A quaternization which has proved particularly advantageous in terms of the compatibility of the resulting polymer with anionic surfactants is the "betainization" of the compounds of formula I, which consists in the quaternization of 25 to 66% of the basic quaternizable groups with sodium. chloroacetate or chloroacetic acid. The yield from the turnover is generally between 60 and 100%.
Graden af "betainiseringen" kan defineres som forholdet mellem 30 antallet af kvaterniserede nitrogenækvivalenter og det samlede antal kvaterniserbare nitrogenækvivalenter ganget med 100.The degree of "betaineization" can be defined as the ratio of the number of quaternized nitrogen equivalents to the total number of quaternizable nitrogen equivalents multiplied by 100.
Kvaterniseringsudbyttet ved reaktionen kan defineres ved forholdet mellem antallet af faktisk kvaterniserede nitrogenækvi-35 valenter og antallet af benyttede ækvivalenter kvaternise-ringsmiddel ganget med 100.The quaternization yield of the reaction can be defined by the ratio of the number of actually quaternized nitrogen equivalents to the number of equivalents used quaternizing agent multiplied by 100.
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Det har vist sig, at kun de to tertiære nitrogenatomer i grupperne A er let kvaterniserbare. Man opnår ved betainisering sekvenser svarende til formlen 5 - A' - Z' - (II) / \ /—\ i hvilken A' er en blanding af grupperne -N N- og -+N N-, V_/ |V_7' ch2 10 co°" og Z' betegner eller βΐ', eller gruppen opnået ved betainisering af B1', eftersom denne indeholder ét eller flere basiske nitrogenatomer, der kan have formlenIt has been found that only the two tertiary nitrogen atoms in group A are readily quaternizable. By betainization sequences corresponding to the formula 5 - A '- Z' - (II) / \ / - \ in which A 'is a mixture of the groups -N N- and - + N N-, V_ / | V_7' ch 2 are obtained And Z 'represents or βΐ', or the group obtained by betainization of B1 ', since it contains one or more basic nitrogen atoms which may have the formula
15 L15 L
-N©- ch2 C00” 20-N © - ch2 C00 ”20
Det har vist sig, at polymererne indeholdt i hårpiejemidlet i-følge opfindelsen og fremstillet ifølge en hvilken som helst af de ovenfor anførte fremgangsmåder er filmdannere og har en relativt lav molekylvægt, dvs. en molekylvægt på mindre end 15.000.It has been found that the polymers contained in the hair care agent of the invention and prepared according to any of the above methods are film-forming and having a relatively low molecular weight, i.e. a molecular weight of less than 15,000.
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De er opløselige i vand eller i vandigt-alkoholisk medium.They are soluble in water or in aqueous-alcoholic medium.
De er navnlig nyttige til hår, som er gjort følsomt efter behandlinger, såsom affarvninger, permanentninger eller farvninger, men kan ligeledes fordelagtigt benyttes til normalt hår.They are especially useful for hair that is made sensitive after treatments, such as dyes, perms or stains, but can also be advantageously used for normal hair.
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Polymererne inkorporeres i mængder på 0,1 til 5% og fortrinsvis 0,2 til 3 vægt% af midlet i forskellige kosmetiske midler, såsom lotioner, cremer eller hårsætningsgeler, regnet som hovedbestanddel, og desuden i shampoo, ondu1 er ingsmid1 er, per-3 5 manentningsfiksativer, farvningsmidler, etc., regnet som hjælpemidler i nærværelse af andre forbindelser, såsom anioniske, kationiske, ikke-ioniske, amfotere eller zwitterioniske over- 9The polymers are incorporated in amounts of 0.1 to 5% and preferably 0.2 to 3% by weight of the agent in various cosmetic agents, such as lotions, creams or hair gels, as the main ingredient, and furthermore in shampoos, cosmetics, cosmetics and cosmetics. 35 fixative fixatives, staining agents, etc., counted as auxiliaries in the presence of other compounds such as anionic, cationic, nonionic, amphoteric or zwitterionic supernatants.
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fladeaktive stoffer, oxidationsmidler, synergi sti sk virkende midler, skumstabilisatorer, sekvenstreringsmidler, overfedt-ningsmidler, tykkelsesmidler, blødgøringsmidler, antiseptiske • midler, konserver ingsmid1 er , farvestoffer , parfumer og germi-5 cider. De kan benyttes i blanding med andre anioniske, katio-niske, amfotere eller ikke-ioniske polymere.surfactants, oxidizing agents, synergistic active agents, foam stabilizers, sequencing agents, fats, thickeners, plasticizers, antiseptics, preservatives, dyes, perfumes and germicides. They can be used in admixture with other anionic, cationic, amphoteric or nonionic polymers.
Alt efter pH-værdien under anvendelse, som ligger mellem 3 og 11, kan polymererne foreligge i forskellige midler i form af 10 salte af uorganiske eller organiske syrer eller i form af frie eller kvaternære baser.Depending on the pH value in use, which is between 3 and 11, the polymers may be present in various agents in the form of 10 salts of inorganic or organic acids or in the form of free or quaternary bases.
De kosmetiske hårplejemidler ifølge opfindelsen kan endvidere foreligge i form af vandige, vandige-alkoholiske eller alkohols liske opløsninger, cremer, pastaer, geler eller puddere. De kan endvidere indeholde et drivmiddel og være indeholdt i en aerosolbeholder.Furthermore, the cosmetic hair care agents of the invention may be in the form of aqueous, aqueous-alcoholic or alcoholic solutions, creams, pastes, gels or powders. They may further contain a propellant and be contained in an aerosol container.
Det omhandlede hårplejemiddel i form af en hårshampoo kan for-20 uden et anionisk, kationisk, ikke-ionisk, amfotert og/eller zwitterionisk overfladeaktivt stof indeholde én eller flere forbindelser bestående af gentagelsesenheder med formlen I samt eventuelt synergistiske skumstabilisatorer, sekvestreringsmid-ler, overfedtningsmidler, tykkelsesmidler, én eller flere kos-25 met i ske harpikser, blødgøringsmidler, farvestoffer, parfumer, baktericider, konserveringsmidler samt et hvilket som helst andet hjælpestof, der sædvanligvis benyttes i kosmetiske midler.The hair care agent in the form of a hair shampoo may contain, without an anionic, cationic, nonionic, amphoteric and / or zwitterionic surfactant, one or more compounds consisting of repeating units of formula I as well as optionally synergistic foam stabilizers, sequestering agents, superficial agents. , thickeners, one or more cosmetics in spoon resins, plasticizers, dyes, perfumes, bactericides, preservatives and any other adjuvant commonly used in cosmetics.
Polymererne med formlen (I) muliggør endvidere fremstilling af 30 ondulationsvæsker, behandlingscremer, hårkonditioneringsmid-ler, anti-skællotioner og andre lignende midler, der er karakteriseret ved, at de indeholder én eller flere polymerer med formlen I og med en molekylvægt, som bestemt ved damptrykssænkning ligger mellem 500 og 15.000.The polymers of formula (I) further enable the preparation of 30 oncotic fluids, treatment creams, hair conditioners, anti-scaling lotions and other similar agents, characterized in that they contain one or more polymers of formula I and having a molecular weight as determined by vapor pressure lowering is between 500 and 15,000.
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De følgende eksempler Al - A14 belyser opfindelsen nærmere, med-dens eksemplerne 1-11 belyser fremstilling af polymererne, der 10The following Examples A1 - A14 illustrate the invention further, while Examples 1-11 illustrate the preparation of the polymers which
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anvendes i midlet ifølge opfindelsen. De anførte dele er vægtdele.used in the composition of the invention. The parts listed are parts by weight.
Eksempel 1 5 Eørste trin - fremstilling af mellemproduktet: E,E-bis/|3-hydroxy-y-ehlor-propyl/diglycolamin med formlen.Example 1 First Step - Preparation of the Intermediate: E, E-Bis / β-hydroxy-γ-ehloro-propyl / diglycolamine of the formula.
C1CH2 - CHOH - CH2 - E - CHg - CHOH - CH2C1 CH9 10 1 2C1CH2 - CHOH - CH2 - E - CHg - CHOH - CH2C1 CH9 10 1 2
ch2 - 0 - CH2 - CH20Hch2 - 0 - CH2 - CH20H
i det følgende omtalt som mellemprodukt X.hereinafter referred to as intermediate X.
Til en opløsning af 420 g diglycolamin (4 mol) i 2700 g vand sættes 15 dråbevis under omrøring 740 g (8 mol) epichlorhydrin i løbet af 1 time ved 10-15°C.To a solution of 420 g of diglycolamine (4 moles) in 2700 g of water is added dropwise with stirring 740 g (8 moles) of epichlorohydrin over 1 hour at 10-15 ° C.
Efter 4 timers omrøring af reaktionsblandingen ved 20°C er epoxid= grupperne praktisk taget forsvundet.After 4 hours of stirring the reaction mixture at 20 ° C, the epoxide = groups have virtually disappeared.
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Man opnår således en klar, meget svagt grønlig opløsning med 30$ tørstof.Thus, a clear, very faint greenish solution with 30 $ solids is obtained.
.Andet trin - fremstilling af en polymer af typen 25 - A - Z - / v i i* i hvor A betegner -E_E-, Z betegner B eller B , B betegner -CH2-CH0H-CH2-, B1' betegner -CH2-CH0H-0H2-E-CH2-CH0H-CH2-, og i hvil- 30 CH? I 2 ch2-o-ch2-ch2oh ken forholdet mellem grupperne A/B^ /B^ er 4/1/3 (de molære forhold piperazin/diglycolamin/epichlorhydrin er 4/1/5).The second step - preparing a polymer of type 25 - A - Z - / vii * wherein A represents -E_E-, Z represents B or B, B represents -CH2-CHOH-CH2-, B1 'represents -CH2-CHOH -0H2-E-CH2-CHOH-CH2-, and in which CH? In 2 ch2-o-ch2-ch2oh the ratio of the groups A / B ^ / B ^ is 4/1/3 (the molar ratios piperazine / diglycolamine / epichlorohydrin are 4/1/5).
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Til 775 g piperazinhexahydrat (4 mol) sættes under opretholdelse af temperaturen 20°C 965 g (1 mol) af en opløsning af mellemproduktet X fremstillet som ovenfor anført. Man tilsætter derpå 277 g (3 mol) epichlorhydrin, stadig ved temperaturen 20°C. Man tilsætter derpå iTo 775 g of piperazine hexahydrate (4 moles) is added while maintaining the temperature 20 ° C 965 g (1 mole) of a solution of the intermediate X prepared as above. 277 g (3 moles) of epichlorohydrin are then added, still at a temperature of 20 ° C. One is then added in
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løbet af 1 time 500 g (5 mol) af en 40$ natriumhydroxidopløsning.over 1 hour 500 g (5 moles) of a 40 $ sodium hydroxide solution.
Der varmes derpå til 80-90°C, og denne temperatur holdes i 1 time.It is then heated to 80-90 ° C and kept at this temperature for 1 hour.
Ved tilsætning af 1130 g vand opnås en opløsning med 20$ aktivt mate-5 riale.By adding 1130 g of water, a solution of 20 $ of active material is obtained.
Eksempel 2Example 2
Direkte fremstilling af en polymer af typen - A - z i hvilken sym-10 bolerne A og Z har samme betydning som i eksempel 1, men hvor fordelingen af piperazin og diglycolamin er statistisk.Direct preparation of a polymer of type - A - z in which the symbols A and Z have the same meaning as in Example 1, but where the distribution of piperazine and diglycolamine is statistical.
Eorholdet mellem grupperne A/B^'/B1 er 4/1/3 som ovenfor anført.The ratio of the groups A / B1 / B1 is 4/1/3 as stated above.
15 Man benytter samme molære mængder af piperazin, diglycolamin og epi= chlorhydrin som i eksempel 1, d.v.s. 4/1/5.The same molar amounts of piperazine, diglycolamine and epi = chlorohydrin are used as in Example 1, i.e. 4/1/5.
Til 161 g piperazinhexahydrat (0,83 mol) og 21 g diglycolamin (0,2 mol) dispergeret i 140 ml vand sættes i løbet af 1 time og ved 20°C 20 92,5 g epichlorhydrin (1 mol). 1 time efter tilsætningen tilsættes dråbevis og stadig ved 20°C 100 g 40$ natriumhydroxid (1 mol). Man opvarmer derpå til 80-90°C, som holdes i 1 time.To 161 g of piperazine hexahydrate (0.83 mol) and 21 g of diglycolamine (0.2 mol) dispersed in 140 ml of water are added over one hour and at 20 ° C 92.5 g of epichlorohydrin (1 mol). One hour after the addition, 100 g of 40 $ sodium hydroxide (1 mol) is added dropwise and still at 20 ° C. It is then heated to 80-90 ° C, which is kept for 1 hour.
Man fortynder derpå reaktionsmediet med 227 ml vand til opnåelse af 25 en 20$’s opløsning af aktivt materiale.The reaction medium is then diluted with 227 ml of water to give 25 a 20 $ solution of active material.
Den således opnåede opløsning er farveløs, og dens viskositet målt ved 25°C er 0,07 Pa.s.The solution thus obtained is colorless and its viscosity measured at 25 ° C is 0.07 Pa.s.
30 Eksempel 3Example 3
Eremstilling af en polymer af typen - A - Z -, i hvilken A betegner og Z betegner B1', B1' betegner -CH2-CH0H-CH2-N-CH2-CH0H-CH2- 0Ho 35 I ά ch2-o-ch2-ch2oh.Preparation of a polymer of the type - A - Z - in which A represents and Z represents B1 ', B1' represents -CH2-CHOH-CH2-N-CH2-CHOH-CH2-OOH in ά ch2-o-ch2- CH 2 OH.
Eorholdet mellem grupperne A/B^' er 1/1.The ratio of the groups A / B ^ 'is 1/1.
Molforholdet piperazin/diglycolamin/epichlorhydrin er 1/1/2.The mole ratio of piperazine / diglycolamine / epichlorohydrin is 1/1/2.
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Til en opløsning af 1 mol (194 g) piperazinhexahydrat i 742 g vand sættes dråbevis i løbet af 1 time ved 20°C under omrøring og under en nitrogenatmosfære 1 mol mellemprodukt X fremstillet ifølge eksempel 1 i form af en 30$'s opløsning (970 g).To a solution of 1 mole (194 g) of piperazine hexahydrate in 742 g of water is added dropwise over 1 hour at 20 ° C with stirring and under a nitrogen atmosphere 1 mole of intermediate X prepared according to Example 1 in the form of a 30 $ solution ( 970 g).
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Efter afsluttet tilsætning boldes reaktionsblandingen -under omrøring ved 20°C i 1 time.After completion of the addition, the reaction mixture is bubbled with stirring at 20 ° C for 1 hour.
Der tilsættes derpå ved samme temperatur og i løbet af 1 time 167,5 g 10 48$ natriumhydroxid (2 mol).Then, at the same temperature and over 1 hour, 167.5 g of 10 $ 48 sodium hydroxide (2 moles) are added.
Omrøring fortsættes i endnu 1 time ved denne temperatur, hvorefter blandingen opvarmes i 2 timer til 80-90°C.Stirring is continued for another hour at this temperature, after which the mixture is heated for 2 hours to 80-90 ° C.
15 Ved tilsætning af 1026,5 g vand opnås en klar og praktisk taget farveløs polyaminopløsning med 10$ aktivt materiale.By adding 1026.5 g of water, a clear and practically colorless polyamine solution with 10 $ active material is obtained.
Eksempel 4 20 Eørste trin - fremstilling af en præpolymer P, som hovedsagelig tillægges formlen:Example 4 First Step - Preparation of a prepolymer P, mainly assigned to the formula:
- CH2 - CH0H - CH2 - Ή - CH2 - CH0H - 0Η£ - jTjIH- CH2 - CH0H - CH2 - Ή - CH2 - CH0H - 0Η £ - jTjIH
0Ho I 20Ho I 2
25 CH2 - 0 - CH2 - CH20HCH2 - O - CH2 - CH2OH
Til en opløsning af 776 g (4 mol) piperazinhexahydrat i 500 g vand sættes under anvendelse af fremgangsmåden ifølge eksempel 3 2 mol af mellemproduktforbindelsen X ifølge eksempel 1 i form af en 30$'s op-30 løsning (1955 g).To a solution of 776 g (4 moles) of piperazine hexahydrate in 500 g of water is added using the procedure of Example 3 2 moles of the intermediate compound X of Example 1 in the form of a 30 $ solution (1955 g).
Efter afsluttet tilsætning holdes reaktionsblandingen under omrøring ved 20°C i 1 time.After completion of the addition, the reaction mixture is kept under stirring at 20 ° C for 1 hour.
35 Man tilsætter derpå ved samme temperatur og i løbet af 1 time 4 mol natriumhydroxid i form af en 48$'s opløsning (335 g). Omrøring fortsættes i endnu 1 time ved denne temperatur, hvorefter blandingen opvarmes i 2 timer til 80-90°C.35 Moles of sodium hydroxide in the form of a 48 $ solution (335 g) are then added at the same temperature and over 1 hour. Stirring is continued for another hour at this temperature, after which the mixture is heated for 2 hours to 80-90 ° C.
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Man opnår således en klar opløsning af en præpolymer P med den ovennævnte formel.Thus, a clear solution of a prepolymer P of the above formula is obtained.
Andet trin - fremstilling af en polymer af typen - A - Z i hvilken 5 A' betegner -IT IT-, Z "betegner B*^ eller B"*" , B^ "betegner -CH2-CH0H-CH2-, og B1' betegnet- CH2 - CHOH - CH2 - ΪΤ - CH2 - CHOH - CHg gh2 ch2 - o - ch2 - ch2oh 1 * 1 10 Porholdet mellem grupperne A/B /B er 2/1/1.Second Step - Preparation of a Polymer of the Type - A - Z in Which 5 A 'represents -IT IT-, Z "represents B *' or B" * ", B ^" represents -CH2-CHOH-CH2-, and B1 denoted- CH2 - CHOH - CH2 - ΪΤ - CH2 - CHOH - CHg gh2 ch2 - o - ch2 - ch2oh 1 * 1 10 The pore ratio between groups A / B / B is 2/1/1.
Molforholdet piperazin/diglycolamin/epichlorhydrin er 2/1/3.The mole ratio of piperazine / diglycolamine / epichlorohydrin is 2/1/3.
Til halvdelen af opløsningen af præpolymeren P fremstillet som oven-15 for anført (1835 g) (svarende til 2 ækvivalenter sekundær amin) sættes dråbevis og under omrøring 92,5 g epichlorhydrin (1 mol).To half of the solution of prepolymer P prepared as above (1835 g) (corresponding to 2 equivalents of secondary amine) is added dropwise and with stirring, 92.5 g of epichlorohydrin (1 mole).
Efter afsluttet tilsætning holdes reaktionsblandingen under omrøring ved 20°C i 1 time.After completion of the addition, the reaction mixture is kept under stirring at 20 ° C for 1 hour.
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Man tilsætter derpå ved samme temperatur og i løbet af 1 time 83 g (1 mol) 48$ natriumhydroxid.Then 83 g (1 mole) of 48 $ sodium hydroxide are added at the same temperature and over 1 hour.
Omrøringen fortsættes i endnu 1 time ved denne temperatur, hvorefter 25 man opvarmer blandingen i 1 time til 80-90°C.Stirring is continued for another hour at this temperature, then the mixture is heated for 1 hour to 80-90 ° C.
Ved tilsætning af 2625 g vand opnås en klar og praktisk taget farveløs polyaminopløsning indeholdende 10$ aktivt materiale.By adding 2625 g of water, a clear and virtually colorless polyamine solution containing 10 $ of active material is obtained.
30 Eksempel 5 /—\Example 5
Eremstilling af en polymer af typen - A - Z -, hvor A betegner -IT_!T-, Z betegner B1 eller B1’, B1' betegner -CH2-CH0H-CH2-1T-CH2-CH0H-CH2-, 35 \E2Preparation of a polymer of the type - A - Z - wherein A represents -IT_T-, Z represents B1 or B1 ', B1' represents -CH2-CHOH-CH2-1T-CH2-CHOH-CH2-, 35 \ E2
CH2-0-CH2-CH20HCH2-0-CH2-CH20H
og B1 betegner -CH2-CHOH-CH2-.and B1 represents -CH2-CHOH-CH2-.
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Forholdet mellem grupperne A/B3" /B^ er 4/1/3.The ratio of groups A / B3 "/ B ^ is 4/1/3.
Det relative molforhold piperazin/diglycolamin/epihalogenhydrin er 4/1/5.The relative molar ratio of piperazine / diglycolamine / epihalohydrin is 4/1/5.
55
Til 394,5 g opløsning af præpolymeren P beskrevet ovenfor og indeholdende 0,43 ækvivalenter sekundær amin sættes under omrøring 51 g 1,3-bis-piperazino-propan-2-ol med formlen indeholdende 0,43 ækvivalenter sekundær amin, d.v.s. svarende til 0,215 mol. 1,3-bis-piperazino-2-propan-2-olen kan fremstilles ved fremgangsmåden beskrevet i eksempel 15 i det tidligere nævnte danske 15 fremlæggelsesskrift.To 394.5 g of solution of the prepolymer P described above and containing 0.43 equivalents of secondary amine are added with stirring 51 g of 1,3-bis-piperazino-propan-2-ol of the formula containing 0.43 equivalents of secondary amine, i.e. corresponding to 0.215 mol. The 1,3-bis-piperazino-2-propan-2-olene can be prepared by the method described in Example 15 of the previously mentioned Danish publication.
Til denne opløsning sættes i løbet af 1 time og ved 20°C 39,7 g (0,43 mol) epichlorhydrin. Blandingen omrøres i 1 time ved denne temperatur. Man tilsætter derpå ved 20°G og i løbet af 1 time 35,8 g · (0,43 20 mol) 48$ natriumhydroxid.To this solution, 39.7 g (0.43 mole) of epichlorohydrin are added over 1 hour and at 20 ° C. The mixture is stirred for 1 hour at this temperature. It is then added at 20 ° G and over one hour 35.8 g · (0.43 20 moles) of 48 $ sodium hydroxide.
Efter 1 times omrøring ved samme temperatur opvarmes reaktionsblandingen i løbet af 1 time til 80-90°C.After stirring for 1 hour at the same temperature, the reaction mixture is heated to 80-90 ° C over 1 hour.
25 Ved tilsætning af 1099 g vand opnås en klar polyaminopløsning indeholdende 10$ aktivt materiale.By adding 1099 g of water a clear polyamine solution containing 10 $ of active material is obtained.
Eksempel 6 30 Fremstilling af en polymer af typen - A - Z i hvilken A betegner -ff ff-, Z betegner B1 eller B3-', B3- betegner - CH2 - CHOH - CH2 - ff - CH2 - CHOH - CH2 -,Example 6 Preparation of a Polymer of the Type - A - Z wherein A represents -ff ff-, Z represents B1 or B3- ', B3- represents - CH2 - CHOH - CH2 - ff - CH2 - CHOH - CH2 -,
CHo0H - C - CHo0HCHOOH - C - CHOHOH
2 i 2 35 ch2 og B^ betegner - CH2 - CHOH - CH2~.2 in CH 2 and B 2 represent - CH 2 - CHOH - CH 2 ~.
Forholdet mellem grupperne A/B^/B1 er 1/0,42/0,56, idet grupperne B1 oa B^ er statistisk fordelt.The ratio of groups A / B ^ / B1 is 1 / 0.42 / 0.56, with groups B1 and B ^ being statistically distributed.
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5 Denne polymer fremstilles ved den direkte fremgangsmåde ifølge eksempel 2 ved at gå ud fra piperazin (1,07 mol), 2-amino-2-methylpropan- 1,3-diol (0,45 mol) og epichlorhydrin (1,5 mol).This polymer is prepared by the direct procedure of Example 2 starting from piperazine (1.07 mol), 2-amino-2-methylpropane-1,3-diol (0.45 mol) and epichlorohydrin (1.5 mol) ).
Man "blander 209 g piperazinhexahydrat (1,07 mol) og 47,2 g 2-amino-2-10 methylpropan-1, 3-diol i 250 ml vand. Man tilsætter i'løbet af 1 time ved 20°C 139 g (1,5 mol) epichlorhydrin. Derpå tilsættes endvidere 150 g 40$ natriumhydroxid (1,5 mol), og der varmes til 80-90°C, hvilken temperatur holdes i 1 time.209 g of piperazine hexahydrate (1.07 mol) and 47.2 g of 2-amino-2-10-methylpropane-1,3-diol are mixed in 250 ml of water. 139 g are added over a period of 1 hour at 20 ° C. (1.5 mole) of epichlorohydrin, then 150 g of 40 $ sodium hydroxide (1.5 mole) is added and heated to 80-90 ° C, which is kept for 1 hour.
15 yed afslutningen af omsætningen fortyndes der med 760 ml vand, og der opnås således en klar opløsning indeholdende 20$ tørstof.After completion of the reaction, dilute with 760 ml of water, thus obtaining a clear solution containing 20 $ dry matter.
Eksempel 7 20 Eremstilling af en polymer af typen - A - Z -, i hvilken A betegner -ff ff-, Z betegner B1 eller B1', B1' betegner - CH2 - CHOH - CH2 - N - CH2 - CHOH - 0¾ -, og B1 betegnerExample 7 Preparation of a polymer of the type - A - Z - in which A represents -ff ff-, Z represents B1 or B1 ', B1' represents - CH2 - CHOH - CH2 - N - CH2 - CHOH - 0¾ -, and B1 represents
CH2 - COOHCH2 - COOH
25 - 0H2 - CHOH - CH2 -.- 0H2 - CHOH - CH2 -.
Gruppeforholdet A/B^'/33^ er 1,2/0,8/0,4, idet grupperne B^ og B^ er statistisk fordelt.The A / B ^ / 33 ^ group ratio is 1.2 / 0.8 / 0.4, with the groups B ^ and B ^ being statistically distributed.
30 Det relative molforhold piperazin/aminoeddikesyre/epichlorhydrin er 1,2/0,8/2.The relative molar ratio of piperazine / aminoacetic acid / epichlorohydrin is 1.2 / 0.8 / 2.
60 g (0,8 mol) amino eddike syre med formlen H2ff-CH2-C00H dispergeret i 218 g vand neutraliseres med 80 g 40$ natriumhydroxid (0,8 mol).60 g (0.8 mole) of amino acetic acid of the formula H2ff-CH2-C00H dispersed in 218 g of water are neutralized with 80 g of 40 $ sodium hydroxide (0.8 mole).
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Til ovennævnte opløsning sættes 233 g (1,2 mol) piperazinhexahydrat. Derpå tilsættes under omrøring i løbet af 1 time og ved 15-20°C 185 g (2 mol) epichlorhydrin.To the above solution is added 233 g (1.2 moles) of piperazine hexahydrate. Then, with stirring over 1 hour and at 15-20 ° C, 185 g (2 moles) of epichlorohydrin are added.
Efter 1 times omrøring ved denne temperatur sættes, stadig ved den samme temperatur, 200 g (2 mol) 40$ natriumhydroxid.After 1 hour of stirring at this temperature, 200 g (2 moles) of 40 $ sodium hydroxide are still added at the same temperature.
Omrøring fortsættes i endnu 1 time ved 20°C og derpå i 1 time ved 80°C. Opløsningen køles og indstilles på 25$ aktivt materiale ved tilsætning af 124 g vand.Stirring is continued for another hour at 20 ° C and then for 1 hour at 80 ° C. The solution is cooled and adjusted to $ 25 active material by the addition of 124 g of water.
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Man opnår således en klar, meget svagt gulfarvet opløsning.Thus, a clear, very faint yellow-colored solution is obtained.
Ved inddampning af en fortyndet opløsning opnås en holdbar og en smule klæbrig film.Evaporating a dilute solution gives a durable and slightly sticky film.
55
Eksempel 8Example 8
Fremstilling af en betainiseret polymer af typen - Al - Ζ» hvor APreparation of a Betainized Polymer of the Type - Al - Ζ »Where A
/“Λ +Λ~\ betegner en blanding af grupperne -N_If- og - E_I-, og Z’ betegner 10 CH0 i 2 coo" B1, d.v.s. - CH9 - CHOH - CEL og grupperne opnået ved betainise- 1 i ^ ^ ring af B , d.v.s. en blanding af grupperne 15 - CH2 - CHOH - CH2 - N - CH2 - CHOH - CH£ - ch2 - ch2 - 0 - ch2 - ch2oh ch2 - COO" og - CH2 - CHOH - CH2 - +H - CH2 - CHOH - CH2 --· 20 ch2 - ch2 - 0 - ch2 - ch2oh./ "Λ + Λ ~ \ represents a mixture of the groups -N_If- and - E_I-, and Z 'represents 10 CHO in 2 COO" B1, ie - CH9 - CHOH - CEL and the groups obtained by betaineise of B, i.e. a mixture of groups 15 - CH2 - CHOH - CH2 - N - CH2 - CHOH - CH2 - ch2 - ch2 - 0 - ch2 - ch2oh ch2 - COO "and - CH2 - CHOH - CH2 - + H - CH2 - CHOH - CH2 - · 20 ch2 - ch2 - 0 - ch2 - ch2oh.
Man betainiserer en polymer opnået ved kondensation af en opløsning af 483 g (2,49 mol) piperazinhexahydrat, 63 g (0,6 mol) diglycolamin, 277,5 g (3 mol) epichlorhydrin og 120 g (3 mol) natriumhydroxid. Op-25 løsningen har en viskositet på 0,075 Pa.s ved 25°C.A polymer obtained by condensing a solution of 483 g (2.49 mole) of piperazine hexahydrate, 63 g (0.6 mole) of diglycolamine, 277.5 g (3 mole) of epichlorohydrin and 120 g (3 mole) of sodium hydroxide. The solution has a viscosity of 0.075 Pa.s at 25 ° C.
/ \/ \
Denne udgangspolymer er af typen - A - Z -, hvor A betegner -Η H-, Z betegner B1 eller B1', B1’ betegner - CH« - CHOH - 0Ho - S - CH0 - CHOH - CH« -, og B1 betegner 30 2 2 i 2 2 CH0 I d ch2 - 0 - ch2 - ch2oh og betegner 35 - CH2 - CHOH - CH2 : Gruppeforholdet A/B^ /B^ er 2,4/0,6/1,8.This starting polymer is of the type - A - Z - where A represents -Η H-, Z represents B1 or B1 ', B1' represents - CH '- CHOH - OHo - S - CH0 - CHOH - CH' -, and B1 represents 30 2 2 in 2 2 CH0 I d ch2 - 0 - ch2 - ch2oh and denotes 35 - CH2 - CHOH - CH2: The group ratio A / B ^ / B ^ is 2.4 / 0.6 / 1.8.
Til 1005 g af nævnte polymer indeholdende 20% aktivt materiale med ialt 2,5 nitrogenækvivalenter sættes 157,4 g (1,34 mol) natriummono-To 1005 g of said polymer containing 20% of active material with a total of 2.5 nitrogen equivalents is added 157.4 g (1.34 mole) of sodium monomer.
17 DK 163478 B17 DK 163478 B
Kvaterniseringsomfanget er 70-71$, og viskositeten af den resulterende forbindelse er 0,067 Pa.s ved 25°C. Betainiseringsgraden er 37,5%, d.v.s. at 37,5% af de basiske nitrogenatomer foreligger i form ch2 - C00" 5 af -The quaternization range is 70-71 $ and the viscosity of the resulting compound is 0.067 Pa.s at 25 ° C. The degree of betaineization is 37.5%, i.e. that 37.5% of the basic nitrogen atoms are in the form ch2 - C00 "5 of -
Eksempel 9 10 Til 1005 g kationisk polymer med 20$ aktivt materiale, benyttet i eksempel 8 , indeholdende ialt 2,5 nitrogenækvivalenter sættes 78,8 g (0,67 mol) natriummonochloracetat, og der opvarmes til 85-100°C i løbet af 5-6 timer. Kvaterniseringsomfanget er 71$, og viskositeten efter omsætningen er 0,06 Pa.s ved 25°C. Betainiseringsgraden er 15 19%.Example 9 To 1005 g of cationic polymer with 20 $ active material used in Example 8 containing a total of 2.5 nitrogen equivalents is added 78.8 g (0.67 mole) of sodium monochloroacetate and heated to 85-100 ° C over 5-6 hours. The quaternization range is $ 71 and the viscosity after the reaction is 0.06 Pa.s at 25 ° C. The degree of betaineization is 15 19%.
Den betainiserede polymer er af samme type som den i eksempel 8 fremstillede og adskiller sig kun ved, at 19$ af de basiske nitrogenato- i + mer foreligger i form af - Ir -The betaine polymer is of the same type as that of Example 8 and differs only in that $ 19 of the basic nitrogen atoms is in the form of - Ir -
20 I20 I
ch2 - cooch2 - coo
Eksempel 10Example 10
Kvaternisering med dimethylsulfatet af forbindelsen ifølge eksempel 2, 25 / \ ί 1*1 i hvilken A betegner -H IT-, Z betegner B eller B , B betegner - CH2 - CHOH - CH2 -, og B1 betegner - CH2 - CHOH - CH2 - N - CH2 - CHOH - CHg - .Quaternization with the dimethyl sulfate of the compound of Example 2, 25/1 in which A represents -H IT-, Z represents B or B, B represents - CH2 - CHOH - CH2 -, and B1 represents - CH2 - CHOH - CH2 - N - CH2 - CHOH - CHg -.
CHp - CHp - 0 - CH« - CH« - OH 30CHp - CHp - 0 - CH «- CH« - OH 30
Den kvaterniserede polymer består i det væsentlige af de to efterfølgende grupper i forholdet 80/20: — if~H+ - 0Eo - CHOH - CH0— \_Λ 2 2 35 ηττ _The quaternized polymer consists essentially of the two following groups in the ratio 80/20: - if ~ H + - 0Eo - CHOH - CH0— \ _Λ 2 2 35 ηττ _
Uil3 S04CH3Owl3 S04CH3
18 DK 163478 B18 DK 163478 B
ψ-3 S04CH3" —±1 - CHo - CHOH - 0Ho-- I 2 2 CHrj I 2±-3 SO 4 CH 3 "- ± 1 - CHo - CHOH - O
5 CH2 - 0 - CH2 - CH2 - OH5 CH2 - 0 - CH2 - CH2 - OH
Til 1082 g vandig opløsning indeholdende 27$ af polymeren fremstillet ifølge eksempel 2, hvori 80$ af natriumchloridet er blevet fjernet ved hjælp af dialyse, og indeholdende 3,37 nitrogenaékvivalenter, tilsættes 10 under omrøring og ved en lavere temperatur end 30°C 254,5 g (2,02 mol) dimethylsulfat. Efter 3 timers omrøring ved denne temperatur indstilles opløsningen på 30$ aktivt materiale ved tilsætning af 485 g vand.To 1082 g of aqueous solution containing 27 $ of the polymer prepared according to Example 2, wherein 80 $ of the sodium chloride has been removed by dialysis and containing 3.37 nitrogen equivalents, is added with stirring and at a temperature lower than 30 ° C 254. 5 g (2.02 mol) of dimethyl sulfate. After 3 hours of stirring at this temperature, the solution of 30 $ active material is adjusted by the addition of 485 g of water.
Den ved inddampning af en vandig opløsning opnåede film er holdbar og 15 en smule klæbrig.The film obtained by evaporation of an aqueous solution is durable and slightly sticky.
Eksempel 11Example 11
Fremstilling af en polymer, der er kvaterniseret ved hjælp af dime-20 thylsulfat og består af følgende to grupper: CHjCH^ S04CH5" ^H3 S04CH3" —/""V - CH0 - CH - CH0— — - CH0 - CHOH - CH9—Preparation of a Polymer Quaternized by Dimethyl 20 Sulfate and Consists of the Following Two Groups: CH 2 CH 2 SO 4 CH 5 - H 3 SO 4 CH 3 - / - V - CH
-p—/ -r c- i c. i c. C-p— / -r c- i c. i c. c
0H CH0 25 S04CH3 I ά0H CH0 25 S04CH3 I ά
L ^ -5 J 0H2 - 0 - CH2 - CH£0HL ^ -5 J 0H2 - 0 - CH2 - CH £ 0H
i forholdet ca. 80/20.in the ratio approx. 80/20.
Til en blanding af 141 g (1,64 mol) pipsrazin og 42 g (0,4 mol) di= 30 glycolamin opløst i 300 ml methanol sættes under omrøring og i løbet af 1 time ved 20°C 185 g (2 mol) epichlorhydrin, hvorefter reaktionsblandingen opvarmes i 30 minutter under tilbagesvaling af opløsningsmidlet.To a mixture of 141 g (1.64 mole) of pipsrazine and 42 g (0.4 mole) of di = 30 glycolamine dissolved in 300 ml of methanol is added with stirring and over 1 hour at 20 ° C 185 g (2 mole) epichlorohydrin, after which the reaction mixture is heated for 30 minutes under reflux of the solvent.
35 i løbet af 2 timer under stadig opvarmning under tilbagesvaling af methanol tilsættes 360 g (2 mol) af en 30$ natriummethylatopløsning i methanol. Hatriumchloridet fjernes ved filtrering.During 2 hours while still warming under reflux of methanol, 360 g (2 moles) of a 30 $ sodium methylate solution in methanol are added. The sodium chloride is removed by filtration.
iin
19 DK 163478 B19 DK 163478 B
261 g af ovennævnte opløsning indeholdende 0,942 nitrogenækvivalenter opvarmes under reduceret tryk til fjernelse af methanolen. Der tilsættes 200 ml dimethylformamid.261 g of the above solution containing 0.942 nitrogen equivalents is heated under reduced pressure to remove the methanol. 200 ml of dimethylformamide are added.
5 Til denne nye opløsning sættes 119 g (0,942 mol) methylsulfat, hvorefter reaktionsblandingen opvarmes under omrøring i 4 -timer ved 90°C.To this new solution is added 119 g (0.942 mol) of methyl sulfate and then the reaction mixture is heated with stirring for 4 hours at 90 ° C.
Ved dråbevis at sætte denne opløsning til et stort overskud af acetone isoleres polymeren i form af et meget hygroskopisk pulver.By dropwise adding this solution to a large excess of acetone, the polymer is isolated in the form of a very hygroscopic powder.
1010
Pilmen opnået ved inddampning af en vandig opløsning er transparent, holdbar og ikke klæbrig.The pill obtained by evaporation of an aqueous solution is transparent, durable and non-sticky.
Eksempel A 1 15Example A 1 15
Anionisk shampoo:Anionic Shampoo:
Forbindelse ifølge eksempel 5 .......................... 1 g laurylsulfat af triethanolamin ......................... 15 g 20 diethanolamid af kokosolie ............................. 3 g mælkesyre indtil pH 7,4 vand indtil ............................................ 100 gCompound of Example 5 .......................... 1 g of lauryl sulfate of triethanolamine ............... .......... 15 g 20 diethanolamide of coconut oil ............................. 3 g lactic acid up to pH 7.4 water until ............................................ 100 g
Eksempel A 2 25 Anionisk shampoo:Example A 2 Anionic Shampoo:
Forbindelse ifølge eksempel 4 .......................... 1>2 g dinatriumhalvestersulfosuccinatet af modificeret alkano lamid ............................................ 10 g natriumlaurylethersulfat kondenseret med 2,2 mol 30 ethylenoxid.......................................... 15 g diethanolamid af kokosolie ............................. 4 g vand indtil ............................................ 100 g pH-værdien er 7.Compound of Example 4 .......................... 1> 2 g disodium halvestersulfosuccinate of modified alkanoamide ........... ................................. 10 g of sodium lauryl ether sulfate condensed with 2.2 moles of ethylene oxide ...... .................................... 15 g of diethanolamide of coconut oil ......... .................... 4 g of water until .......................... .................. 100 g of pH is 7.
3535
Eksempel A 3Example A 3
Shampoo:Shampoo:
20 DK 163478 BDK 163478 B
Forbindelse ifølge eksempel 5 ......................... 0,75 g 5 laurylalkohol polyethoxyleret med 12 mol ethylenoxid .. 12 g diethanolamid af kokosolie ............................ 4 g trimethylcetylammoniumbromid.......................... 0,5 g citronsyre indtil pH 4 10 vand indtil ........................................... 100 gCompound of Example 5 ......................... 0.75 g of 5 lauryl alcohol polyethoxylated with 12 moles of ethylene oxide .. 12 g of diethanolamide of coconut oil ... ......................... 4 g trimethylcetylammonium bromide ...................... .... 0.5 g citric acid up to pH 4 10 water until ................................... ........ 100 g
Eksempel A 4 Shampoo: 15 Forbindelse ifølge eksempel 3......................... 1 g natriumlaurylethersulfat kondenseret med 2,2 mol ethylenoxid ........................................... 10 g alkylimidazolin med formlen °**0Η2 - COO Ha 20 ΟίίΗ07 - C-TS( j'j oH 0^2 - ch2 - 0 - CH2 - COOTa 2 25 solgt under betegnelsen "Miranol C2M" ................. 2 g monoethanolamid af kokosolie .......................... 1,5 g mælkesyre indtil pH 7,5 vand indtil ........................................... 100 g 30Example A 4 Shampoo: Compound of Example 3 ......................... 1 g of sodium lauryl ether sulfate condensed with 2.2 moles of ethylene oxide ..... ...................................... 10 g of alkylimidazoline of the formula ° ** 0Η2 - COO Ha 20 ΟίίΗ07 - C-TS (j'j oH 0 ^ 2 - ch2 - 0 - CH2 - COOTa 2 25 sold under the designation "Miranol C2M" ................. 2 g monoethanolamide of coconut oil ......................... 1.5 g lactic acid up to pH 7.5 water until ......... .................................. 100 g 30
Eksempel A 5 Shampoo:Example A 5 Shampoo:
Forbindelse ifølge eksempel 4 ......................... 1,5 g 35 laurylalkohol polyethoxyleret med 12 mol ethylenoxid .. 8 g n natriumsaltet af H-(H’,H'-diethylaminopropyl)-N -dodecylasparagin...................................... 4 g diethanolamid af kokosolie ............................ 2 g mælkesyre indtil pH 5Compound of Example 4 ......................... 1.5 g of lauryl alcohol polyethoxylated with 12 moles of ethylene oxide. 8 g of the sodium salt of H- (H ', H'-diethylaminopropyl) -N-dodecylasparagine ...................................... 4 g of coconut oil diethanolamide ............................ 2 g of lactic acid up to pH 5
21 DK 163478 B21 DK 163478 B
Eksempel A 6Example A 6
Anionisk shampoo:Anionic Shampoo:
Forbindelse ifølge eksempel 2 ......................... lg 5 laurylsulfat af triethanolamin ........................ 10 g natriumlaurylethersulfat ethoxyleret med 2,2 mol ethylenoxid ........................................... 10 g diethanolamid af kokosolie ............................ 3 g 10 vand indtil ........................................... 100 g pH = 8Compound of Example 2 ......................... and 5 lauryl sulfate of triethanolamine ................ ........ 10 g of sodium lauryl ether sulfate ethoxylated with 2.2 moles of ethylene oxide ................................ ........... 10 g diethanolamide of coconut oil ............................ 3 g 10 water until. .......................................... 100 g pH = 8
Eksempel A 7 15 Anionisk shampoo:Example A 7 15 Anionic Shampoo:
Forbindelse ifølge eksempel 8 1 g laurylsulfat af triethanolamin ........................ 10 g natriumlaurylethersulfat ethoxyleret med 2,2 mol 20 ethylenoxid........................................... 10 g diethanolamid af kokosolie ............................ 3 g vand indtil ........................................... 100 g pH =7,5 25Compound of Example 8 1 g of lauryl sulfate of triethanolamine ........................ 10 g of sodium lauryl ether sulfate ethoxylated with 2.2 moles of 20 ethylene oxide ...... ..................................... 10 g of diethanolamide of coconut oil ........ .................... 3 g of water until .......................... ................. 100 g pH = 7.5 25
Eksempel A 8 Anionisk shampoo:Example A 8 Anionic Shampoo:
Forbindelse ifølge eksempel 8 ........................ 0,75 g 30 natriumlaurylethersulfat ethoxyleret med 2,2 mol ethylenoxid ........................................... 10 g oxid af lauryldimethylamin (solgt under betegnelsen (Ammonyx 10") ......................................... 2 g 35 diethanolamid af kokosolie ............................ 2,5 g vand indtil ........................................... 100 g pH = 7,5Compound of Example 8 ........................ 0.75 g of sodium lauryl ether sulfate ethoxylated with 2.2 moles of ethylene oxide ......... .................................. 10 g oxide of lauryl dimethylamine (sold under the designation (Ammonyx 10 ") .. ....................................... 2 g 35 diethanolamide of coconut oil ..... ....................... 2.5 g of water until ..................... ...................... 100 g pH = 7.5
22 DK 163478 B22 DK 163478 B
Eksempel A 9Example A 9
Eationisk shampoo:Eationic shampoo:
Forbindelse ifølge eksempel 2 ......................... 1,2 g 5 laurylalkohol polyethoxyleret med 12 mol ethylenoxid .. 12 g trimethylcetylammoniumbromid (solgt under betegnelsen "Cetavlon") ........................................... 1 g diethanolamid af kokosolie .....................-....... 2 g 10 mælkesyre indtil pH 5 vand indtil ........................................... 100 gCompound of Example 2 ......................... 1.2 g of 5 lauryl alcohol polyethoxylated with 12 moles of ethylene oxide. 12 g of trimethylcetylammonium bromide (sold under the designation " Cetavlon ") ........................................... 1 g of diethanolamide off coconut oil ..................... 2 g 10 lactic acid up to pH 5 water until ........... ................................ 100 g
Eksempel A 10 15 Shampoo:Example A 10 Shampoo:
Forbindelse ifølge eksempel 7 ......................... 1,5 g forbindelse med formlen 0^^25^2¾°....... -6 g forbindelse med formlen R-CHOH-CH^/CHg-CHOH-C^O?^- H 20 hvor R betegner en alkylgruppe med 9-12 carbonatomer .. 5 g oxid af lauryldimethylamin (solgt under betegnelsen "Ammonyx: 10”) ......................................... 2 g mælkesyre indtil β 4 25 vand indtil ........................................... 100 gCompound of Example 7 ......................... 1.5 g Compound of Formula 0 ^^ 25 ^ 2¾ ° ....... -6 g of compound of formula R-CHOH-CH 2 / CH 3 -CHOH-C 2 O 2 - H 20 where R represents an alkyl group of 9-12 carbon atoms. 5 g of oxide of lauryl dimethylamine (sold under the designation "Ammonyx: 10 ”) ......................................... 2 g of lactic acid until β 4 25 water until ........................................... 100 g
Eksempel A 11 Shampoo: 30 Forbindelse ifølge eksempel 7 ......................... 1 g laurylsulfat af triethanolamin........................ 15 g lauryldiethanolamid................................... 3 g vand indtil ........................................... 100 g 35 pH =7,5 23Example A 11 Shampoo: Compound of Example 7 ......................... 1 g lauryl sulfate of triethanolamine .......... .............. 15 g lauryl diethanolamide ................................ .. 3 g of water until ........................................... 100 g pH = 7.5 23
Eksempel A12Example A12
Anionisk shampoo:Anionic Shampoo:
DK 163478 BDK 163478 B
Forbindelse ifølge eksempel 10 ........................ 1>5 g 5 laurylmyristylethersulfat af monoethanolamin ethoxyle- ret med 2,2 mol ethylenoxid ........................... 12 g diethanolamid af kokosolie ............................ 2,5 g vand indtil ........................................... 100 g 10 pH = 8Compound of Example 10 ........................ 1> 5 g of 5 lauryl myristyl ether sulfate of monoethanolamine ethoxylated with 2.2 moles of ethylene oxide ..... ...................... 12 g of diethanolamide of coconut oil ....................... ..... 2.5 g of water until ....................................... .... 100 g 10 pH = 8
Eksempel A 13 Anionisk shampoo: 15 Forbindelse ifølge eksempel 10 ........................ Ig oxid af lauryldimethylamin med formlen CH* I 3 C12H25 “ ......................................... g 20 ch5 diethanolamider af kokosoliefedtsyrer ................. 2 g natriumlanrylmyris tylethersulfat ethoxyleret med 2,2 mol ethylenoxid ....................................... 8,5 g 25 vand indtil ........................................... 100 g pH = 7,5Example A 13 Anionic Shampoo: Compound of Example 10 ........................ Ig oxide of lauryl dimethylamine of formula CH * I 3 C12H25 "... ...................................... g 20 ch5 diethanolamides of coconut oil fatty acids ...... ........... 2 g of sodium lanrylmyris tyl ether sulfate ethoxylated with 2.2 moles of ethylene oxide ............................ ........... 8.5 g 25 water until ................................ ........... 100 g pH = 7.5
Eksempel A 14 30 Kationisk shampoo:Example A 14 30 Cationic Shampoo:
Forbindelse ifølge eksempel 10 ........................ 2 g laurylalkohol ethoxyleret med 12 mol ethylenoxid ...... 10 g diethanolamider af kokosfedtsyrer ..................... 5 g 35 lauryldimethylaminoxid ................................ 2,5 g vand indtil ........................................... 100 g pH = 5Compound of Example 10 ........................ 2 g lauryl alcohol ethoxylated with 12 moles of ethylene oxide ...... 10 g diethanolamides of coconut fatty acids ... .................. 5 g of 35 lauryl dimethyl amine oxide ............................ .... 2.5 g of water until ........................................ ... 100 g pH = 5
Claims (14)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK161280A DK161280A (en) | 1974-08-02 | 1980-04-16 | hair care |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7427030A FR2280361A2 (en) | 1974-08-02 | 1974-08-02 | HAIR TREATMENT AND CONDITIONING COMPOSITIONS |
| FR7427030 | 1974-08-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK350875A DK350875A (en) | 1976-02-03 |
| DK163478B true DK163478B (en) | 1992-03-09 |
| DK163478C DK163478C (en) | 1992-07-27 |
Family
ID=9142077
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK350875A DK163478C (en) | 1974-08-02 | 1975-08-01 | Cosmetic Hair Care Containing A Cationic Polymer |
Country Status (12)
| Country | Link |
|---|---|
| JP (3) | JPS5151528A (en) |
| AT (1) | AT355727B (en) |
| BE (1) | BE832063R (en) |
| BR (1) | BR7504935A (en) |
| CA (1) | CA1066449A (en) |
| CH (1) | CH579909A5 (en) |
| DE (2) | DE2534514C2 (en) |
| DK (1) | DK163478C (en) |
| FR (1) | FR2280361A2 (en) |
| GB (2) | GB1510488A (en) |
| IT (1) | IT1050594B (en) |
| NL (1) | NL177730C (en) |
Families Citing this family (259)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2280361A2 (en) * | 1974-08-02 | 1976-02-27 | Oreal | HAIR TREATMENT AND CONDITIONING COMPOSITIONS |
| LU76955A1 (en) * | 1977-03-15 | 1978-10-18 | ||
| FR2460133B1 (en) * | 1979-07-02 | 1986-11-07 | Bristol Myers Co | COMPOSITION FOR HAIR CARE AND METHOD OF APPLICATION |
| FR2470596A1 (en) * | 1979-11-28 | 1981-06-12 | Oreal | COMPOSITION FOR THE TREATMENT OF KERATIN FIBERS BASED ON AMPHOTERIC POLYMERS AND CATIONIC POLYMERS |
| DE3044738C2 (en) * | 1979-11-28 | 1994-09-15 | Oreal | Preparations and methods for the treatment of human hair |
| FR2486394A1 (en) * | 1979-11-28 | 1982-01-15 | Oreal | COMPOSITION FOR THE TREATMENT OF KERATIN FIBERS BASED ON AMPHOTERIC POLYMERS AND ANIONIC POLYMERS |
| DE3044754C2 (en) * | 1979-11-28 | 1995-06-01 | Oreal | Agents and processes for the treatment of keratin fibers |
| LU83020A1 (en) * | 1980-12-19 | 1982-07-07 | Oreal | OIL COMPOSITION FOR THE TREATMENT OF KERATINIC MATERIALS AND THE SKIN |
| LU83349A1 (en) * | 1981-05-08 | 1983-03-24 | Oreal | AEROSOL FOAM COMPOSITION BASED ON CATIONIC POLYMER AND ANIONIC POLYMER |
| LU86599A1 (en) * | 1986-09-19 | 1988-04-05 | Oreal | COSMETIC COMPOSITIONS BASED ON CATIONIC POLYMERS AND ALKYLOXAZOLINE POLYMERS |
| FR2718960B1 (en) * | 1994-04-22 | 1996-06-07 | Oreal | Compositions for the treatment and protection of hair, based on ceramide and polymers with cationic groups. |
| FR2718961B1 (en) * | 1994-04-22 | 1996-06-21 | Oreal | Compositions for washing and treating hair and skin based on ceramide and polymers with cationic groups. |
| FR2729852A1 (en) | 1995-01-30 | 1996-08-02 | Oreal | REDUCTIVE COMPOSITION COMPRISING BASIC AMINO ACID AND CATIONIC POLYMER |
| FR2749506B1 (en) | 1996-06-07 | 1998-08-07 | Oreal | DETERGENT COSMETIC COMPOSITIONS FOR HAIR USE AND USE |
| FR2749507B1 (en) * | 1996-06-07 | 1998-08-07 | Oreal | DETERGENT COSMETIC COMPOSITIONS AND USE |
| FR2751532B1 (en) * | 1996-07-23 | 1998-08-28 | Oreal | WASHING AND CONDITIONING COMPOSITIONS BASED ON SILICONE AND DIALKYLETHER |
| FR2767473B1 (en) | 1997-08-25 | 2000-03-10 | Oreal | COSMETIC COMPOSITIONS CONTAINING A POLYOXYALKYLENE AMINE SILICONE BLOCK COPOLYMER AND A CONDITIONING AGENT AND USES THEREOF |
| FR2773069B1 (en) | 1997-12-29 | 2001-02-02 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE AMIDOETHERCARBOXYLIC ACID SURFACTANT AND AT LEAST ONE ASSOCIATION OF AN ANIONIC POLYMER AND A CATIONIC POLYMER |
| FR2785799B1 (en) | 1998-11-12 | 2002-11-29 | Oreal | COSMETIC CONDITIONING AND DETERGENT COMPOSITION COMPRISING A CARBOXYLIC SURFACTANT, A SILICONE AND A CATIONIC POLYMER, USE AND METHOD. |
| FR2788975B1 (en) | 1999-01-29 | 2002-08-09 | Oreal | AQUEOUS READY-TO-USE KERATIN FIBER DECOLORING COMPOSITION COMPRISING THE ASSOCIATION OF A WATER-SOLUBLE SOLVENT AND A NON-IONIC OR ANIONIC AMPHIPHILIC POLYMER COMPRISING AT LEAST ONE FAT CHAIN |
| FR2788976B1 (en) | 1999-01-29 | 2003-05-30 | Oreal | KERATIN FIBER DECOLORING ANHYDROUS COMPOSITION COMPRISING THE ASSOCIATION OF A WATER-SOLUBLE THICKENING POLYMER AND A NON-IONIC AMPHIPHILIC POLYMER COMPRISING AT LEAST ONE FAT CHAIN |
| FR2788974B1 (en) | 1999-01-29 | 2001-03-30 | Oreal | KERATINIC FIBER DECOLORING ANHYDROUS COMPOSITION COMPRISING THE ASSOCIATION OF ANIONIC AND / OR NON-IONIC AMPHIPHILIC POLYMERS COMPRISING AT LEAST ONE FATTY CHAIN AND CATIONIC OR AMPHOTERIC SUBSTANTIVE POLYMERS |
| FR2788972B1 (en) | 1999-02-03 | 2001-04-13 | Oreal | HAIR COMPOSITION COMPRISING A WASHING BASE, A CATIONIC POLYMER AND AN ANIONIC POLYURETHANE AND USE THEREOF |
| FR2788973B1 (en) | 1999-02-03 | 2002-04-05 | Oreal | COSMETIC COMPOSITION COMPRISING AN ANIONIC SURFACTANT, AN AMPHOTERIC SURFACTANT, A POLYOLEFIN OIL, A CATIONIC POLYMER AND A WATER-SOLUBLE SALT OR ALCOHOL, USE AND METHOD |
| FR2795310B1 (en) | 1999-06-25 | 2003-02-14 | Oreal | COSMETIC COMPOSITIONS CONTAINING AN AMPHOTERIC POLYMER AND A FIXING / CONDITIONING POLYMER AND USES THEREOF |
| FR2795316B1 (en) | 1999-06-28 | 2004-12-24 | Oreal | PERMANENT PROCESS COMPRISING THE PRELIMINARY APPLICATION OF A COMPOSITION COMPRISING AT LEAST ONE ANIONIC POLYMER |
| FR2795634A1 (en) | 1999-06-30 | 2001-01-05 | Oreal | MASCARA COMPRISING FILM-FORMING POLYMERS |
| FR2795635B1 (en) | 1999-06-30 | 2006-09-15 | Oreal | MASCARA COMPRISING FILMOGENIC POLYMERS |
| FR2799971B1 (en) | 1999-10-20 | 2001-12-07 | Oreal | COSMETIC COMPOSITIONS CONTAINING A VINYLDIMETHICONE / DIMETHICONE COPOLYMER AND A CATIONIC POLYMER AND USES THEREOF |
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| WO2023120389A1 (en) | 2021-12-20 | 2023-06-29 | L'oreal | Composition comprising hydrophobicized cationic polymer |
| FR3131847A1 (en) | 2022-01-20 | 2023-07-21 | L'oreal | COMPOSITION COMPRISING A HYDROPHOBIZED CATIONIC POLYMER |
| FR3131846A1 (en) | 2022-01-19 | 2023-07-21 | L'oreal | COMPOSITION COMPRISING A HYDROPHOBIZED POLYION COMPLEX PARTICLE |
| KR20240093864A (en) | 2021-12-20 | 2024-06-24 | 로레알 | Composition Comprising Hydrophobized Polyion Complex Particles |
| WO2023228870A1 (en) | 2022-05-25 | 2023-11-30 | L'oreal | Composition for coloring keratin fibers |
| FR3137835A1 (en) | 2022-07-15 | 2024-01-19 | L'oreal | Composition for coloring keratinous fibers |
| FR3141342A1 (en) | 2022-10-28 | 2024-05-03 | L'oreal | COMPOSITION COMPRISING A POLYIONIC COMPLEX BASED ON HYALURONIC ACID AND A SUPERABSORBENT POLYMER |
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| WO2024097256A1 (en) | 2022-10-31 | 2024-05-10 | L'oreal | Systems and methods for stabilizing compositions, and compositions comprising the systems |
| FR3142896A1 (en) | 2022-12-09 | 2024-06-14 | L'oreal | SYSTEMS AND METHODS FOR STABILIZING COMPOSITIONS, AND COMPOSITIONS INCLUDING THE SYSTEMS |
| WO2024135301A1 (en) | 2022-12-19 | 2024-06-27 | L'oreal | Composition comprising hyaluronic acid-including hydrophobicized nanoparticles |
| FR3145282A1 (en) | 2023-01-30 | 2024-08-02 | L'oreal | COMPOSITION COMPRISING HYALURONIC ACID, INCLUDING HYDROPHOBIC NANO PARTICLES |
| FR3145279A1 (en) | 2023-01-30 | 2024-08-02 | L'oreal | COMPOSITION COMPRISING A POLYIONIC COMPLEX BASED ON HYALURONIC ACID AND A LIPOPHILIC ANTIOXIDANT |
| FR3145281A1 (en) | 2023-01-27 | 2024-08-02 | L'oreal | COMPOSITION COMPRISING A POLYIONIC COMPLEX BASED ON HYALURONIC ACID AND A HYDROPHILIC ANTIOXIDANT |
| WO2024135424A1 (en) | 2022-12-20 | 2024-06-27 | L'oreal | Composition comprising hyaluronic acid-based polyion complex and hydrophilic or lipophilic antioxidant |
| FR3145278A1 (en) | 2023-01-30 | 2024-08-02 | L'oreal | STABLE DISPERSION COMPOSITION COMPRISING A RETINOID |
| WO2024135577A1 (en) | 2022-12-23 | 2024-06-27 | L'oreal | Stable dispersion composition comprising retinoid |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE791128A (en) * | 1971-11-12 | 1973-05-09 | Bayer Ag | POLYAMINES CONTAINING ACID GROUPS AND THEIR PREPARATION PROCESS |
| LU64371A1 (en) * | 1971-11-29 | 1973-06-21 | ||
| FR2280361A2 (en) * | 1974-08-02 | 1976-02-27 | Oreal | HAIR TREATMENT AND CONDITIONING COMPOSITIONS |
-
1974
- 1974-08-02 FR FR7427030A patent/FR2280361A2/en active Granted
-
1975
- 1975-07-31 JP JP9367675A patent/JPS5151528A/en active Pending
- 1975-08-01 DE DE19752534514 patent/DE2534514C2/en not_active Expired
- 1975-08-01 CH CH1010375A patent/CH579909A5/xx not_active IP Right Cessation
- 1975-08-01 GB GB3228575A patent/GB1510488A/en not_active Expired
- 1975-08-01 CA CA232,769A patent/CA1066449A/en not_active Expired
- 1975-08-01 NL NL7509188A patent/NL177730C/en active Search and Examination
- 1975-08-01 IT IT6902175A patent/IT1050594B/en active
- 1975-08-01 BR BR7504935A patent/BR7504935A/en unknown
- 1975-08-01 GB GB42977A patent/GB1510489A/en not_active Expired
- 1975-08-01 AT AT598575A patent/AT355727B/en not_active IP Right Cessation
- 1975-08-01 BE BE158890A patent/BE832063R/en not_active IP Right Cessation
- 1975-08-01 DK DK350875A patent/DK163478C/en active
- 1975-08-01 DE DE19752560488 patent/DE2560488C2/de not_active Expired
-
1984
- 1984-11-09 JP JP23538684A patent/JPS60142910A/en active Granted
- 1984-12-10 JP JP26060984A patent/JPS60142909A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CH579909A5 (en) | 1976-09-30 |
| DE2534514A1 (en) | 1976-02-12 |
| CA1066449A (en) | 1979-11-13 |
| GB1510488A (en) | 1978-05-10 |
| AU8359675A (en) | 1977-02-03 |
| DK163478C (en) | 1992-07-27 |
| NL7509188A (en) | 1976-02-04 |
| BE832063R (en) | 1976-02-02 |
| DE2534514C2 (en) | 1988-12-22 |
| DE2560488C2 (en) | 1987-12-03 |
| JPS5151528A (en) | 1976-05-07 |
| AT355727B (en) | 1980-03-25 |
| JPS6335607B2 (en) | 1988-07-15 |
| FR2280361A2 (en) | 1976-02-27 |
| NL177730B (en) | 1985-06-17 |
| ATA598575A (en) | 1979-08-15 |
| IT1050594B (en) | 1981-03-20 |
| JPS60142909A (en) | 1985-07-29 |
| NL177730C (en) | 1985-11-18 |
| GB1510489A (en) | 1978-05-10 |
| BR7504935A (en) | 1976-07-27 |
| DK350875A (en) | 1976-02-03 |
| JPS6335608B2 (en) | 1988-07-15 |
| FR2280361B2 (en) | 1981-11-13 |
| JPS60142910A (en) | 1985-07-29 |
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