EP0805671A1 - Produits capillaires a base aqueuse contenant des terpolymeres homogenes combinant des proprietes de mise en forme et de traitement du cheveu - Google Patents

Produits capillaires a base aqueuse contenant des terpolymeres homogenes combinant des proprietes de mise en forme et de traitement du cheveu

Info

Publication number
EP0805671A1
EP0805671A1 EP95944239A EP95944239A EP0805671A1 EP 0805671 A1 EP0805671 A1 EP 0805671A1 EP 95944239 A EP95944239 A EP 95944239A EP 95944239 A EP95944239 A EP 95944239A EP 0805671 A1 EP0805671 A1 EP 0805671A1
Authority
EP
European Patent Office
Prior art keywords
hair care
terpolymer
hair
care product
homogeneous
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP95944239A
Other languages
German (de)
English (en)
Other versions
EP0805671A4 (fr
Inventor
Kou-Chang Liu
Robert B. Login
Yakir Reuven
Janice Kay Bees
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ISP Investments LLC
Helene Curtis Industries Inc
Original Assignee
ISP Investments LLC
Helene Curtis Industries Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US08/365,720 external-priority patent/US6299866B1/en
Priority claimed from US08/365,257 external-priority patent/US5523369A/en
Application filed by ISP Investments LLC, Helene Curtis Industries Inc filed Critical ISP Investments LLC
Publication of EP0805671A1 publication Critical patent/EP0805671A1/fr
Publication of EP0805671A4 publication Critical patent/EP0805671A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182—Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen

Definitions

  • This invention relates to hair care products, and, particularly to hair care compositions which provide both hair styling and conditioning for the user, characterized by the presence therein of a homogeneous terpolymer of predetermined composition.
  • Multifunctional hair care products such as hair styling and conditioning compositions have become popular with the public.
  • Such compositions have been made available in the form of gels, lotions, sprays, mousses and glazes, which can be removed after use either immediately, for example, in the so-called “rinse-off” application, where, however, some of the composition remains on the hair after treatment with water, or by the "leave-on” application, where some time later, a majority of the composition is removed with water, or all of it is removed with shampoo.
  • Hair styling and conditioning compositions in the form of gels are provided by the inclusion of a suitable amount of a gelling agent, generally to provide a 7-10,000 cps formulation which can be dispensed by hand or by pump application.
  • Lotion hair care products are hydroalcoholic (3-15%) formulations which can be applied by hand.
  • Sprays are formulations for application by pump action.
  • Mousses are compositions which can be dispensed easily and conveniently from an aerosol can as a pressure sensitive foam. Glazes are thin gel formulations. Mousse and gel hair styling compositions have become particularly popular with the public.
  • a mousse gives an appearance of penetration of the hair as the foam collapses and has ingredients that perform functions that are needed for the improved styling of hair.
  • these ingredients add body to the hair, thereby making it appear fuller on the head of the user, and enhance the combability of the hair in order to make it more manageable.
  • some of the collapsed foam may be designed to be combed out of the hair during the process of styling.
  • hair care products which is reduced or alcohol-free, is desired in the hair care industry.
  • hair care polymers which are also suitable for use in water-based, multifunctional hair care products, and, which can perform the dual functions of styling and conditioning effectively.
  • a further object herein is to provide such hair care products in the form of gels, lotions, sprays, mousses and glazes which can be removed after use either immediately or some time thereafter.
  • Another object of the invention is to provide multifunctional hair styling and conditioning compositions containing homogeneous polymers of a plurality of monomers, including a vinyl lactam, preferably vinyl pyrrolidone (VP) , a quaternary amino monomer, preferably 3-methacrylamidopropyl trimethylammonium chloride (MAPTAC) , and a hydrophobic monomer, preferably a C 4 -C 32 alkyl methacrylate, most preferably octadecyl methacrylate (ODMA) .
  • VP vinyl lactam
  • VP vinyl pyrrolidone
  • MAAC 3-methacrylamidopropyl trimethylammonium chloride
  • ODMA octadecyl methacrylate
  • Yet another object of this invention is to provide a water-based, rinse-off, hair care product which can provide both hair styling and conditioning functions, containing a homogeneous terpolymer of predetermined composition, which can be deposited onto hair as a clear film.
  • a particular object herein is to provide a hair care product including a positively charged fixative homogeneous terpolymer which has a predetermined ratio of hydrophilic-to-hydrophobic monomers therein, with predominately hydrophilic components, and which can be formulated into a 100% water-based hair care product.
  • the polymers in such composition are made by polymerizing a plurality of monomers while adjusting the feeding rates for the faster reacting monomers relative to the precharged slowest reacting monomer so that all the monomers ca react at substantially the same rate during the polymerization.
  • the water-based, hair care product of the invention contains a homogeneous terpolymer of predetermined composition having both hair styling and conditioning properties.
  • the homogeneous terpolymer of the invention comprises, by weight, about 55-99%, preferably 65-95%, of a vinyl lactam, preferably vinyl pyrrolidone (VP) , about 0.5-49%, preferably 5-25%, of a quaternary amino monomer, e.g., (3-methacrylamidopropyl) trimethylammoniu chloride (MAPTAC) , and about 0.5-49%, preferably 1-25%, of a hydrophobic monomer, having the formula RMA, where R is C 4 -C 32 alkyl, preferably C 12 -C 32 alkyl, and, most preferably, octadecyl methacrylate (ODMA) .
  • the homogeneous terpolymer suitably is present in the hair care product in an amount of about 0.2-20%, preferably 1-10%, most preferably 2-8%, by weight of the product.
  • the terpolymer of the invention furnishes a positive charge (MAPTAC) and a predetermined blend of hydrophilic components (VP/MAPTAC) to its hydrophobic component (RMA) , to provide both styling and conditioning functions.
  • MATAC positive charge
  • VP/MAPTAC hydrophilic components
  • RMA hydrophobic component
  • the homogeneous polymerization process of the invention includes precharging VP, and solvent, and introducing the MAPTAC and ODMA monomers incrementally at rates corresponding to the rate of disappearance of VP, over a given period of time.
  • FIGURE 1 is a graphical representation of a conventional non-homogeneous ("one-pot") polymerization process for making a terpolymer of vinylpyrrolidone (VP) , 3-methacrylamidopropyl tri ethylammonium chloride (MAPTAC) , and octadecyl methacrylate (ODMA) monomers from precharged amounts of the monomers.
  • VP vinylpyrrolidone
  • MAAC 3-methacrylamidopropyl tri ethylammonium chloride
  • ODMA octadecyl methacrylate
  • FIGURE 2 is a graphical representation of the homogeneous process of the invention for making the same terpolymer.
  • Vinylpyrrolidone is the most preferred vinyl lactam.
  • the vinyl lactam monomer is present in an amount of about 55-99%, and, preferably, 65-95%, by weight of the terpolymer.
  • the quaternary amino acrylamide or acrylate monomer in the terpolymer of the invention has the formula:
  • R is C 2 -C 20 alkyl or , where n is 0-10 ,
  • X and X A are independently H, or C A to C 8 alkyl
  • R 1# R 2 and R 3 are independently C ⁇ C ⁇ alkyl
  • Z is a halide, sulfate or sulfonate.
  • Suitable examples of amino acrylamides, acrylates, methacrylamides, or methacrylates which are employed as monomers in the terpolymer of the invention include quaternized salts of
  • N-[ (dimethylamino)alkyl]methacrylamides or acrylamides, methacrylates and acrylates of their quaternized halide, sulfate and sulfonate salts are preferred.
  • MATAC 3-methacrylamidopropyl) trimethylammonium chloride
  • quaternized amino acrylamide is (3-methacrylamidopropyl)trimethylammonium chloride
  • the formula is represented by X and X j being CH 3 ; Y being NH; R being C 3 alkyl; R 1# R 2 and R 3 being methyl; and Z being chloride.
  • the quaternary amino monomer suitably is present in the terpolymer in an amount of about 0.5-49%, and, preferably 1-25%, by weight of the terpolymer.
  • the vinyl lactam and quaternary amino acrylamide or acrylate monomers constitute the hydrophilic portion of the terpolymer of the invention.
  • hydrophobic monomer in the terpolymer of the invention suitably has the formula: RMA where R is a C 4 -C 32 alkyl, preferably C 12 -C 32 alkyl, or a mixture thereof; and MA is an acrylate, methacrylate, acrylamide or methacrylamide.
  • Suitable hydrophobic monomers include 2-ethylhexyl methacrylate, dodecyl acrylate, tetradecyl acrylate, octadecyl methacrylate (ODMA) , octadecyl methacrylamide, dodecyl acrylamide and 2-ethylhexyl methacrylamide.
  • a preferred hydrophobic monomer is octadecyl methacrylate.
  • the hydrophobic monomer is present in an amount of about 0.5-49%, preferably 1-25%, by weight of the terpolymer.
  • the homogeneous polymerization process of the invention is illustrated by making substantially homogeneous terpolymers of VP, MAPTAC and ODMA in a predetermined composition.
  • the least reactive monomer of the terpolymer (VP) is precharged into a reactor at a suitable reaction temperature, generally about 50-80°C. , and preferably 55-75°C.
  • the more reactive monomers (MAPTAC and ODMA) then are introduced incrementally into the VP-charged reactor at a rate which corresponds to the observed rate of disappearance of VP, over the period of polymerization.
  • the entire predetermined amount of the MAPTAC and ODMA monomers are added before substantially all the VP monomer has been consumed so that all monomers can react to form a substantially homogeneous terpolymer in a desired compositional ratio of VP:MAPTAC:ODMA. Consequently, a substantially homogeneous terpolymer is obtained whose composition approaches the nominal monomer ratio of the desired terpolymer composition and whose structure has the three individual monomeric units of the copolymer distributed substantially uniformly in a homogeneous chain along the backbone of the polymer.
  • the precharge in the process of the invention may include some MAPTAC and ODMA therein, generally in an amount of up to about 15% of the total amount of MAPTAC and ODMA required for a predetermined terpolymer composition without affecting the homogeneous polymerization process. However, it is still necessary that the rate of addition of MAPTAC and ODMA after any precharge be carried out at substantially the rate of disappearance of VP during polymerization.
  • the schedule of addition of MAPTAC and ODMA to accomplish the desired matched rate of reaction of VP is determined in the following manner.
  • the MAPTAC and ODMA monomers react much more rapidly than VP. Accordingly, after 100 minutes, for example, all the MAPTAC and ODMA monomers are consumed while residual VP monomer still is available for homopolymerization.
  • the terpolymer formed is of a composition different from the desired monomer ratios selected by the precharged amounts of the two monomers.
  • the polymer product obtained is a complex mixture of a homopolymer which is polyvinylpyrrolidone, various copolymers, and a terpolymer of the several monomers of uncertain composition.
  • the curve of rate of reaction vs. time for both MAPTAC and ODMA substantially coincide or match the rate of reaction curve for VP.
  • the VP is precharged and substantially all the MAPTAC and RMA monomers are fed external to the precharge at a feeding schedule determined by analysis of the data of FIGURE 1.
  • the % MAPTAC and ODMA monomers to be fed at time t of the polymerization is determined from the Asymmetric Double Sigmoidal Distribution formula, A j ., below, which has four adjustable parameters, a l t a , a 3 and a 4 : At - 1 -
  • t time in minutes during copolymerization
  • a_ is a parameter which determines the center of the distribution
  • a 2 is a parameter which affects the width of the distribution
  • a 3 is a parameter which determines the ascending portion of the distribution
  • a 4 is a parameter which determines the descending portion of the distribution.
  • N time when the polymerization is completed.
  • % unreacted MAPTAC or ODMA at time t is too large, then the value of a 3 (ascendency) in the - ⁇ formula is increased, a 4 (descendency) is decreased, a j ⁇ (center) is decreased, and a 2 (width) is decreased. Conversely, if the initial guess values of a ⁇ through a give a reaction rate for MAPTAC or ODMA which is too fast, then changes in the values of a ⁇ through a 4 are made in a direction opposite to those discussed above.
  • the matched curves of VP, MAPTAC and ODMA in FIGURE 2 will have at least one set of values for a x , a 2 , a 3 and a 4 (the last set of the iterative fitting process) for suitable feeding of MAPTAC and ODMA over the entire period of polymerization.
  • One such set is:
  • VP (303.6 g) , MAPTAC (7.8 g) , ODMA (3.1 g) , and ethanol (1001.0 g) are charged into a 2-liter resin pot equipped with a gas inlet, a liquid inlet, a thermometer and a condenser.
  • the pH of the solution is adjusted to about 7.5 with KOH.
  • a stream of nitrogen is introduced which bubbles through the solution during the reaction.
  • the solution is gradually heated to 65°C.
  • MAPTAC (63.2 g) and octadecyl methacrylate (ODMA) (51.4 g) are introduced incrementally into the pot with vigorous stirring over a period of 5 hours so that the relative concentrations of the monomeric VP, MAPTA and ODMA monomer remain practically constant throughout the reaction at predetermined levels.
  • Lupersol 11 t-butylperoxy pivalate in mineral spirits
  • the rate of the addition of the catalyst is such that 2 ml of Lupersol is completely delivered in 4 hours.
  • the solution is held for an additional 3 hours at the 68°C.
  • the product is an alcoholic solution of the homogeneous terpolymer of VP, MAPTAC and ODMA.
  • the homogeneous terpolymer of the invention contains a predetermined dominant blend of a hydrophilic part, i.e. VP/MAPTAC, and a small proportion of a hydrophobic monomer, i.e. RMA.
  • This homogeneous terpolymer composition enables the terpolymer to be readily adsorbed onto the negatively charged hair in high amounts as clear films, and to provide both styling and conditioning functions, while still being capable of being readily rinsed or washed-off with water or shampoo after use.
  • the homogeneous terpolymer of the invention comprises about 0.2-20%, preferably 1-10%, and, most preferably, about 2-8%, by weight of the hair care product, the rest being water, and, optionally including an organic solvent such as ethanol, and/or other acceptable adjuvant components such as silicones, surface active agents, viscosity modifiers, dyes, chelating agents, distributing aids, pearlescent aids, opacifiers, perfumes, fatty alcohols, pH adjusting agents, and the like.
  • an organic solvent such as ethanol
  • other acceptable adjuvant components such as silicones, surface active agents, viscosity modifiers, dyes, chelating agents, distributing aids, pearlescent aids, opacifiers, perfumes, fatty alcohols, pH adjusting agents, and the like.
  • the homogeneous terpolymer of the invention finds particular utility in multifunctional hair care products such as water-based, rinse-off hair styling and conditioning products, and in leave-on hair care products such as a mousse, and may be included as a concentrate, or as a gel, and applied as a self-actuated pump hair spray, or in an aerosol product with a propellant.
  • Various actuator and packaging devices known in the art may be used therewith.
  • Representative hair care compositions including the homogeneous terpolymer of the invention are given below.
  • Stabileze® 06 (Crosslinked 1. . 00 maleic anhydride- methyl vinyl ether - ISP)
  • Triethanolamine 98% 1. . 00 Sodium Cocoyl Isethionate 2 . . 50 Color (Pigment) 4 . . 00 Hydroxylated Lecithin 1. . 00 Preservative/Fragrance qs Propellant A-46 5 . 00

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Produits capillaires à base aqueuse contenant des terpolymères homogènes combinant des propriétés de mise en forme et de traitement du cheveu.
EP95944239A 1994-12-28 1995-12-27 Produits capillaires a base aqueuse contenant des terpolymeres homogenes combinant des proprietes de mise en forme et de traitement du cheveu Withdrawn EP0805671A4 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US365720 1994-12-28
US08/365,720 US6299866B1 (en) 1994-12-28 1994-12-28 Water-based, hair care products containing homogeneous terpolymers having both hair styling and conditioning properties
US08/365,257 US5523369A (en) 1994-12-28 1994-12-28 Homogeneous polymerization process for making substantially homogeneous terpolymers
US365257 1994-12-28
PCT/US1995/016891 WO1996019966A1 (fr) 1994-12-28 1995-12-27 Produits capillaires a base aqueuse contenant des terpolymeres homogenes combinant des proprietes de mise en forme et de traitement du cheveu

Publications (2)

Publication Number Publication Date
EP0805671A1 true EP0805671A1 (fr) 1997-11-12
EP0805671A4 EP0805671A4 (fr) 1999-02-10

Family

ID=27002843

Family Applications (1)

Application Number Title Priority Date Filing Date
EP95944239A Withdrawn EP0805671A4 (fr) 1994-12-28 1995-12-27 Produits capillaires a base aqueuse contenant des terpolymeres homogenes combinant des proprietes de mise en forme et de traitement du cheveu

Country Status (6)

Country Link
EP (1) EP0805671A4 (fr)
JP (1) JPH11500417A (fr)
CN (1) CN1171044A (fr)
AU (1) AU703824B2 (fr)
CA (1) CA2203401A1 (fr)
WO (1) WO1996019966A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19838196A1 (de) 1998-08-24 2000-03-02 Basf Ag Kationische Polymerisate und ihre Verwendung
DE19907715A1 (de) * 1999-02-23 2000-08-24 Schwarzkopf Gmbh Hans Zubereitungen zur Behandlung keratinischer Fasern
US6207778B1 (en) * 1999-05-07 2001-03-27 Isp Investments Inc. Conditioning/styling terpolymers
DE10008263A1 (de) 2000-02-23 2001-08-30 Basf Ag Kosmetisches Mittel
DE10160991A1 (de) * 2001-12-12 2003-06-18 Beiersdorf Ag Haarfestiger mit kationischer Substanz
EP2039338A1 (fr) * 2007-09-20 2009-03-25 Rhodia Opérations Composition fortement mousseuse
JP6487641B2 (ja) * 2014-06-30 2019-03-20 中野製薬株式会社 スタイリング化粧料

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU463915B2 (en) * 1972-10-12 1975-08-07 Gaf Corporation Copolymers of vinyl pyrrolidone containing quaternary ammonium groups and methods therefor
US3910862A (en) * 1970-01-30 1975-10-07 Gaf Corp Copolymers of vinyl pyrrolidone containing quarternary ammonium groups
US3954960A (en) * 1970-01-30 1976-05-04 Gaf Corporation Hair and similar cosmetic preparations containing a quaternized copolymer of vinyl pyrrolidone
WO1990001920A1 (fr) * 1988-08-25 1990-03-08 Gaf Chemicals Corporation Polymeres vinyle lactame amino-acrylamide resistant a l'hydrolyse

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4039734A (en) * 1966-03-24 1977-08-02 Imperial Chemical Industries Limited Production of random or homogeneous copolymers
JPS5849715A (ja) * 1981-08-13 1983-03-24 ジ−・エ−・エフ・コ−ポレ−シヨン ビニルカプロラクタム／ビニルピロリドン／アクリル酸アルキルを含有する毛髪調合剤

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3910862A (en) * 1970-01-30 1975-10-07 Gaf Corp Copolymers of vinyl pyrrolidone containing quarternary ammonium groups
US3954960A (en) * 1970-01-30 1976-05-04 Gaf Corporation Hair and similar cosmetic preparations containing a quaternized copolymer of vinyl pyrrolidone
AU463915B2 (en) * 1972-10-12 1975-08-07 Gaf Corporation Copolymers of vinyl pyrrolidone containing quaternary ammonium groups and methods therefor
WO1990001920A1 (fr) * 1988-08-25 1990-03-08 Gaf Chemicals Corporation Polymeres vinyle lactame amino-acrylamide resistant a l'hydrolyse

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO9619966A1 *

Also Published As

Publication number Publication date
JPH11500417A (ja) 1999-01-12
AU703824B2 (en) 1999-04-01
WO1996019966A1 (fr) 1996-07-04
CN1171044A (zh) 1998-01-21
CA2203401A1 (fr) 1996-07-04
EP0805671A4 (fr) 1999-02-10
AU4608996A (en) 1996-07-19

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