WO2002009656A2 - Reshapable hair styling composition comprising acrylic emulsions - Google Patents
Reshapable hair styling composition comprising acrylic emulsions Download PDFInfo
- Publication number
- WO2002009656A2 WO2002009656A2 PCT/IB2001/001568 IB0101568W WO0209656A2 WO 2002009656 A2 WO2002009656 A2 WO 2002009656A2 IB 0101568 W IB0101568 W IB 0101568W WO 0209656 A2 WO0209656 A2 WO 0209656A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition according
- hair
- composition
- reshapable
- monomers
- Prior art date
Links
Classifications
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
Definitions
- the present invention relates to a reshapable hair styling composition.
- Fixing the hairstyle is an important element in hair styling, and involves maintaining a
- the term "hair styling composition” relates to
- any kind of hair composition that can be used to effect hair styling, for example fixing
- compositions shampoos, conditioners, permanent waving compositions, hair care
- compositions comprising a
- solution usually alcohol- or water-based, and one or more materials, generally
- polymer resins One of the functions of polymer resins is to form links between the
- This solution is generally packaged either in an appropriate aerosol
- hair styling compositions include styling gels and mousses, which are known hair styling compositions.
- compositions are essentially aqueous and their application wets the hair
- the hairstyle has a tendency to take on an
- hair conditioning benefits such as ease of combing and soft
- a subject of the invention is a reshapable hair styling composition comprising,
- At least acrylic polymer comprising: (a)
- Another subject of the invention is a reshapable hair styling composition
- the term "reshapable" hair styling composition means a hair styling
- composition providing hair styling that can be restored or modified without new
- “reshapable” effect means to provide a hair styling that can be restored or modified
- composition without new material or heat being applied.
- efficacy of the composition can be any organic compound or without new material or heat being applied.
- reshapable include repositionable, remoldable,
- emulsion means a stable mixture of two or more
- All emulsions comprise a continuous phase
- polyfunctional crosslinking agents means a
- crosslinking agent having an average functionality greater than 1 , such as greater
- the at least one emulsion comprises at least
- At least one acrylic polymer comprising: (a) about 50 to about 90% by weight, such as
- polymer further comprising up to about 50% by weight units derived from at least one
- the at least one co-polymerizable monomer may be any co-polymerizable monomer.
- the at least one co-polymerizable monomer may be any co-polymerizable monomer.
- Alkylacrylate monomers may
- methyl methacrylate examples include methyl methacrylate, isobomyl acrylate, ethyl acrylate, methyl acrylate,
- Useful polar monomers include acrylic acid;
- (meth)acrylamides such as N,N, -dimethyl acrylamides and N-octylacrylamide; dimethylaminoethyl methacrylate; acrylonitrile; 2-carboxyethyl acrylate; maleic
- methoxypolyethylene glycol 550 monoacrylate available from Sartomer Co. under the
- monomers include styrene and C1 -C4 vinyl esters such as vinyl acetate, vinyl
- co-polymerizable ethylenically unsaturated free radically polymerizable monomers are present in the range up to about 30% by weight.
- Polyfunctional crosslinking agents if included, may be copolymerizable with
- the monomeric components of the acrylic polymer or may by added to the
- copolymerizable crosslinking agents examples include
- alkyl triacrylates and tetracrylates such as trimethylol propane triacrylate
- copolymerizable crosslinking agent is 1 ,6-hexanediol diacrylate.
- Post-additive crosslinking agents may also be used. Examples of
- post-additive crosslinking agents include but are not limited to multifunctional
- aziridine amides such as 1 ,1'-(1 ,3-phenylenedicarbonyl)bis[2-methyl aziridine],
- the metal ion is copper, zinc, zirconium, and chromium.
- the metal ion is copper, zinc, zirconium, and chromium.
- crosslinkers are chosen from chelated esters of ortho-titanic acid sold under the
- the TYZOR is TYZOR AA, which is titanium acetyl acetonate.
- Crosslinking agents when used, comprise up to about 10 parts by weight,
- emulsions of the present invention are initiators that, on exposure to heat, generate
- water soluble initiators are preferred.
- Suitable water-soluble initiators include but are not limited to those chosen from
- potassium persulfate ammonium persulfate, sodium persulfate, and mixtures thereof;
- persulfates and reducing agents such as those chosen from sodium metabisulfite and
- the water-soluble initiator is potassium
- Suitable oil-soluble initiators include but are not limited to those chosen from
- the oil-soluble thermal initiator is (2,2'-azobis(isobutyronitrile)).
- initiators may comprise from about 0.05 to about 1 part by weight, also
- the copolymerizable mixture may optionally further comprise a chain transfer
- useful chain transfer agents include but are not limited to those
- the chain transfer agent is chosen from isooctylthioglycolate and carbon tetrabromide.
- the emulsion mixture may further comprise up to about 0.5
- a chain transfer agent typically about 0.01 weight percent to about
- Polymerization via emulsion techniques may require the presence of an
- emulsifier (which may also be called an emulsifying agent or a surfactant).
- emulsifiers for the present invention include those chosen from anionic surfactants,
- nonionic surfactants and mixtures thereof.
- Useful anionic surfactants include but are not limited to those whose molecular
- structure includes at least one hydrophobic moiety chosen from about C6 - to about
- Said salts are chosen from alkali metal salts, ammonium salts, tertiary amino salts, and the like.
- Representative commercial examples of useful anionic surfactants are chosen from alkali metal salts, ammonium salts, tertiary amino salts, and the like.
- Useful nonionic surfactants include but are not limited to those whose
- molecular structure comprises a condensation product of an organic aliphatic or alkyl
- HLB Hydrophilic-Lipophilic Balance
- the HLB of a surfactant is an
- Rhone-Poulenc available from Rhone-Poulenc as the IGEPAL CA or CO series, respectively;
- the emulsion polymerization of this invention is carried out
- a useful range of emulsifier concentration is from about 0.5 to about 8 weight percent, preferably from about 1 to about 5 weight
- the acrylic emulsions of the invention may also contain one or more
- Preferred additives include plasticizers, dyes, fillers,
- antioxidants and UV stabilizers.
- Such additives can be used if they do not adversely
- the acrylic emulsions of the present invention are prepared by a semi-continuous emulsion polymerization process. In the process, a
- surfactant n-butyl acrylate monomers, hydroxyalkyl (meth)acrylate (b) monomers, and the optional components such as co-polymerizable monomers, polyfunctional
- crosslinking agents chain transfer agents, pH modifiers, and other additives.
- induction temperature typically about 50 °C to about
- the first initiator is added to initiate the polymerization and the reaction is
- the monomer pre-emulsion comprising Dl water, surfactant,
- n-butyl acrylate monomers hydroxyalkyl (meth)acrylate (b) monomers, and the
- optional components such as co-polymerizable monomers, polyfunctional crosslinking agents, chain transfer agents, and other additives is added to the stirred flask over a period of time, typically 2 to 4 hours, while the temperature is maintained.
- the second initiator charge if used, is added to the
- the mixture is cooled to room temperature (about 23 °C.) and the latex is
- the pH of the latex prepared using this method is typically about 2 to about 3.
- the acidity of the latex can be modified following latex formation using a pH modifier
- a basic solution e.g., solutions of sodium hydroxide, ammonium hydroxide
- buffer solutions e.g., sodium bicarbonate and the like
- buffer solutions e.g., sodium bicarbonate and the like
- the pH is 7 or less. In another embodiment, the pH is in
- the acrylic polymers may be neutralized in one embodiment of the invention.
- Suitable neutralizing agents may be chosen
- organic, inorganic, and organomineral bases such as amino methyl propanols, sodium and potassium hydoxides, primary, secondary and tertiary amines, ammoniacs, derivatives thereof, and combinations thereof.
- the acrylic has a glass transition
- Tg temperature ranging from about -100 to about 15°C.
- the Tg of the acrylic is obtained following the application of the acrylic
- the glass transition temperature is determined by
- DSC Differential Scanning Calorimetric method
- composition according to the invention may comprise at least one other
- perfumes perfumes; UV filters; active haircare agents; plasticizers; anionic, cationic,
- amphoteric, nonionic, and zwitterionic surfactants such as
- silicone fluids fatty esters, fatty alcohol, long chain hydrocarbons, emollients,
- lubricants such as lanolin compounds, protein hydrolysates, and
- polymers ; dyes; tints; bleaches; reducing agents; pH adjusting agents; sunscreens;
- the appropriate cosmetically acceptable vehicle is adapted to the method of
- the vehicle preferably comprises an appropriate solvent to
- compositions according to the invention can be provided in any form
- a vaporizable composition including in the form of a vaporizable composition, mousse, gel, or lotion.
- composition may be in any of the conventional form including, but not
- compositions hair dye compositions, hair straightening compositions, hair fixing
- composition according to the invention may be vaporizable, for example
- a pump or may be a pressurized aerosol composition. It may be vaporizable by
- a dispensing valve controlled by a dispensing head, which in turn comprises a nozzle
- a vaporizable composition according to the
- the appropriate solvent comprises an appropriate solvent.
- the appropriate solvent is selected from any solvent.
- lower alcohol means a C1-C4 aliphatic alcohol, preferably
- the vaporizable composition according to the invention is an aerosol
- composition it additionally comprises an appropriate amount of propellant.
- propellant comprises compressed or liquefied gases, which are normally employed
- Suitable gasses include compressed air,
- carbon dioxide nitrogen, and gases, which are soluble or otherwise in the composition, such as dimethyl ether, fluorinated or non-fluorinated hydrocarbons, and
- the present invention additionally provides an aerosol device comprising a
- an aerosol composition which comprises on the one hand a liquid phase (or juice) comprising at least one hair styling material as described above in an appropriate medium and on the other hand a propellant, and a dispenser for dispensing said aerosol composition.
- the present invention additionally provides a method of treating keratinous
- fibers, especially hair in which the composition according to the invention as defined above is applied to the hair before, during, or after the shaping of the hairstyle.
- compositions according to the invention can be rinsed off or not rinsed off the hair.
- present invention additionally provides the use of a composition as
- composition according to the invention can be provided in any form known
- a vaporizable composition a mousse, a gel, or a lotion.
- hair styling composition can be determined by an in vivo test. Specifically, a
- composition comprising the acrylic emulsion and a cosmetically
- composition is in the form of a lotion
- the in vivo test proceeds as follows. The hair of the model is washed and then divided into two
- composition is applied to one
- the reference composition may, for example, be chosen from
- the hairdresser dries and styles both sides of the head.
- the two sides of the head are
- the hair is brushed in different directions to remove
- composition is a reshapable hair styling composition.
- a reshapable hair styling composition is a reshapable hair styling composition.
- composition permits (1) the original hair styling to be restored after brushing and (2)
- composition to be evaluated is in another form, such as a shampoo
- the in vivo test can be appropriately modified by one skilled in the art.
- in vivo testing may require testing on 10-20 different individuals.
- HOA methyl methacrylate
- MMA methyl methacrylate
- RHODACAL DS- 10 sodium dodecyl benzene sulfonate surfactant
- reaction mixture was then heated to 70 °C and maintained at this temperature for 20
- This pre-emulsified mixture contained 345.6 grams of BA, 69.12 grams of
- Example 2 To a 2000ml reactor was added 37.0 grams of n-butyl acrylate (BA), 7.68
- HOA 2-hydroxyethyl acrylate
- MMA methyl methacrylate
- reaction mixture was then heated to 70 °C and maintained at this temperature for 20
- This pre-emulsified mixture contained 295.8 grams of BA, 69.12 grams of
- mousse or lotion were prepared using the components and amounts in weight percent listed hereafter. The testing was conducted on several models with one part
- compositions were applied to wet hair after shampooing. In some instances, the composition was rinsed off after
- the hair was then dried, brushed, and evaluated.
- Example 1 4 % active material
- Example 2 8 % active material
- Example 1 8 % active material
- Example 1 1 % active material
- Formulation D imparted very good reshapable effect much better than the reference with very good cosmetic properties (soft hair with good touch).
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- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2003-7001084A KR20030017652A (en) | 2000-07-27 | 2001-07-12 | Reshapable hair styling composition comprising acrylic emulsions |
CA002416907A CA2416907A1 (en) | 2000-07-27 | 2001-07-12 | Reshapable hair styling composition comprising acrylic emulsions |
AU2001280017A AU2001280017B2 (en) | 2000-07-27 | 2001-07-12 | Reshapable hair styling composition comprising acrylic emulsions |
BR0113020-0A BR0113020A (en) | 2000-07-27 | 2001-07-12 | Removable hair styling composition, aerosol device and method for cosmetic hair treatment |
AU8001701A AU8001701A (en) | 2000-07-27 | 2001-07-12 | Reshapable hair styling composition comprising acrylic emulsions |
MXPA03000701A MXPA03000701A (en) | 2000-07-27 | 2001-07-12 | Reshapable hair styling composition comprising acrylic emulsions. |
JP2002515211A JP2004521860A (en) | 2000-07-27 | 2001-07-12 | Hair reforming hair styling composition containing acrylic emulsion |
EP01958297A EP1353627A2 (en) | 2000-07-27 | 2001-07-12 | Reshapable hair styling composition comprising acrylic emulsions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US62705500A | 2000-07-27 | 2000-07-27 | |
US09/627,055 | 2000-07-27 |
Publications (3)
Publication Number | Publication Date |
---|---|
WO2002009656A2 true WO2002009656A2 (en) | 2002-02-07 |
WO2002009656A8 WO2002009656A8 (en) | 2002-05-30 |
WO2002009656A3 WO2002009656A3 (en) | 2003-08-28 |
Family
ID=24512992
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/IB2001/001568 WO2002009656A2 (en) | 2000-07-27 | 2001-07-12 | Reshapable hair styling composition comprising acrylic emulsions |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1353627A2 (en) |
AU (1) | AU2001280017B2 (en) |
CA (1) | CA2416907A1 (en) |
PL (1) | PL365575A1 (en) |
WO (1) | WO2002009656A2 (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1321130A2 (en) * | 2001-12-20 | 2003-06-25 | L'oreal | Reshapable hair styling composition comprising (meth)acrylic copolymers |
EP1336401A1 (en) * | 2001-12-20 | 2003-08-20 | L'oreal | Reshapable hair styling non rinsed compositions comprising (meth)acrylic copolymers |
US6645478B2 (en) | 2001-06-22 | 2003-11-11 | L'oreal S.A. | Reshapable hair styling composition comprising (meth)acrylic copolymers of four or more monomers |
US6667378B2 (en) | 2001-06-22 | 2003-12-23 | L'oreal, S.A. | Reshapable hair styling composition comprising heterogeneous (meth)acrylic copolymer particles |
US6689346B1 (en) | 2000-10-25 | 2004-02-10 | L'oreal | Reshapable hair styling composition comprising acrylic copolymers |
AU2001280017B2 (en) * | 2000-07-27 | 2004-07-08 | L'oreal | Reshapable hair styling composition comprising acrylic emulsions |
EP1495749A2 (en) | 2003-07-07 | 2005-01-12 | Beiersdorf AG | Fixing cosmetic composition allowing multiple reshaping of the hair |
WO2007003784A1 (en) | 2005-07-01 | 2007-01-11 | L'oreal | Neutralised cationic polymer, composition containing said polymer and a cosmetic treatment method |
FR2924336A1 (en) * | 2007-11-30 | 2009-06-05 | Oreal | HAIR COMPOSITION COMPRISING (METH) ACRYLIC COPOLYMERS AND AT LEAST ONE OIL. |
FR2924341A1 (en) * | 2007-11-30 | 2009-06-05 | Oreal | Reshapable hair styling composition comprises (meth)acrylic copolymers comprising butyl (meth)acrylate monomer units, hydroxyalkyl (meth)acrylate monomer units and other copolymerizable monomer units, and fillers |
US8691199B2 (en) | 2004-07-13 | 2014-04-08 | L'oreal | Ethylenic copolymers, compositions and methods of the same |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5919439A (en) * | 1993-08-23 | 1999-07-06 | The Procter & Gamble Company | Silicone grafted thermoplastic elastomeric copolymers and hair and skin care compositions containing the same |
EP0985405A2 (en) * | 1998-09-11 | 2000-03-15 | Rohm And Haas Company | Stiff-feel hair styling compositions |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PL365575A1 (en) * | 2000-07-27 | 2005-01-10 | L'oreal | Reshapable hair styling composition comprising acrylic emulsions |
-
2001
- 2001-07-12 PL PL01365575A patent/PL365575A1/en unknown
- 2001-07-12 AU AU2001280017A patent/AU2001280017B2/en not_active Ceased
- 2001-07-12 WO PCT/IB2001/001568 patent/WO2002009656A2/en not_active Application Discontinuation
- 2001-07-12 CA CA002416907A patent/CA2416907A1/en not_active Abandoned
- 2001-07-12 EP EP01958297A patent/EP1353627A2/en not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5919439A (en) * | 1993-08-23 | 1999-07-06 | The Procter & Gamble Company | Silicone grafted thermoplastic elastomeric copolymers and hair and skin care compositions containing the same |
EP0985405A2 (en) * | 1998-09-11 | 2000-03-15 | Rohm And Haas Company | Stiff-feel hair styling compositions |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2001280017B2 (en) * | 2000-07-27 | 2004-07-08 | L'oreal | Reshapable hair styling composition comprising acrylic emulsions |
US6689346B1 (en) | 2000-10-25 | 2004-02-10 | L'oreal | Reshapable hair styling composition comprising acrylic copolymers |
US6645478B2 (en) | 2001-06-22 | 2003-11-11 | L'oreal S.A. | Reshapable hair styling composition comprising (meth)acrylic copolymers of four or more monomers |
US6667378B2 (en) | 2001-06-22 | 2003-12-23 | L'oreal, S.A. | Reshapable hair styling composition comprising heterogeneous (meth)acrylic copolymer particles |
US7048916B2 (en) | 2001-06-22 | 2006-05-23 | L'oreal S.A. | Reshapable hair styling composition comprising heterogeneous (meth)acrylic copolymer particles |
US7122175B2 (en) | 2001-06-22 | 2006-10-17 | L'oreal S.A. | Reshapable hair styling composition comprising (meth)acrylic copolymers of four or more monomers |
EP1321130A2 (en) * | 2001-12-20 | 2003-06-25 | L'oreal | Reshapable hair styling composition comprising (meth)acrylic copolymers |
EP1336401A1 (en) * | 2001-12-20 | 2003-08-20 | L'oreal | Reshapable hair styling non rinsed compositions comprising (meth)acrylic copolymers |
EP1321130A3 (en) * | 2001-12-20 | 2003-07-02 | L'oreal | Reshapable hair styling composition comprising (meth)acrylic copolymers |
EP1495749A2 (en) | 2003-07-07 | 2005-01-12 | Beiersdorf AG | Fixing cosmetic composition allowing multiple reshaping of the hair |
US8691199B2 (en) | 2004-07-13 | 2014-04-08 | L'oreal | Ethylenic copolymers, compositions and methods of the same |
US8722028B2 (en) | 2004-07-13 | 2014-05-13 | L'oreal | Ethylenic copolymers, compositions and methods of the same |
WO2007003784A1 (en) | 2005-07-01 | 2007-01-11 | L'oreal | Neutralised cationic polymer, composition containing said polymer and a cosmetic treatment method |
FR2924336A1 (en) * | 2007-11-30 | 2009-06-05 | Oreal | HAIR COMPOSITION COMPRISING (METH) ACRYLIC COPOLYMERS AND AT LEAST ONE OIL. |
FR2924341A1 (en) * | 2007-11-30 | 2009-06-05 | Oreal | Reshapable hair styling composition comprises (meth)acrylic copolymers comprising butyl (meth)acrylate monomer units, hydroxyalkyl (meth)acrylate monomer units and other copolymerizable monomer units, and fillers |
Also Published As
Publication number | Publication date |
---|---|
AU2001280017B2 (en) | 2004-07-08 |
CA2416907A1 (en) | 2002-02-07 |
WO2002009656A3 (en) | 2003-08-28 |
PL365575A1 (en) | 2005-01-10 |
EP1353627A2 (en) | 2003-10-22 |
WO2002009656A8 (en) | 2002-05-30 |
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