GB2468790A - Fluid composition for application to hair ahead of heat styling - Google Patents

Fluid composition for application to hair ahead of heat styling Download PDF

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Publication number
GB2468790A
GB2468790A GB1006419A GB201006419A GB2468790A GB 2468790 A GB2468790 A GB 2468790A GB 1006419 A GB1006419 A GB 1006419A GB 201006419 A GB201006419 A GB 201006419A GB 2468790 A GB2468790 A GB 2468790A
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United Kingdom
Prior art keywords
hair
fluid composition
composition according
styling
water
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GB1006419A
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GB201006419D0 (en
Inventor
Marie Whatmough
Paul Alfred Cornwell
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PZ Cusons PLC
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PZ Cusons PLC
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Publication of GB201006419D0 publication Critical patent/GB201006419D0/en
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/046Aerosols; Foams
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/24Thermal properties
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/20Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30Characterized by the absence of a particular group of ingredients
    • A61K2800/31Anhydrous

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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)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

A fluid composition for application to hair ahead of heat styling with a straightening iron, curling tong, hair dryer or similar type of device, comprises a solvent, where the composition comprises less than 5% by weight of water. Preferably, the solvent is a mixture of ethanol and cyclomethicone. The composition may be used to prevent damage to hair during heat styling. Preferably, the composition comprises an agent selected from silicone polymers; silicone and hydrocarbon block or graft co-polymers; cationic polymers based on a polysaccharide or protein back bone; cationic polymers based on a synthetic hydrocarbon backbone; cationic surfactants; or mixtures thereof.

Description

Heat protection spray The present invention aims to protect hair from heat generated during styling.
Exposure to thermal stresses, through the very high temperatures created by styling apparatus such as blow driers, curling tongs and straightening irons, can cause serious damage to hair structures. The effects of such heat styling damage are documented as being more structural than chemical, although some chemical changes have also been described.
In detail, the combined combing and blow-drying of hair can produce deep ovoidal (or bubble) cuticle cracks. These cracks are attributed to a combination of cyclic extension actions and the rapid escape of water whilst drying (Robbins, C. R. (2002), Chemical and physical behaviour of human hair. 4th Ed., Springer). Cycles of wetting and blow-drying hair can also result in the formation of multiple cracks in the cuticle, aligned parallel to the longitudinal axis of the hair fibre (Gamez-Garcia, M.
S
(1998), "The cracking of human hair cuticles by cyclical thermal stresses" Journal of *.S.** * S Cosmetic Science 49(3): 141-153). The authors suggest that the cracks form when the *.S* external portions of the cuticles undergo drastic dehydration. In other words, an
S *.S
* 20 expanded, hydrated cortex surrounded by dry, stretched cuticle, makes the cuticle S.....
* . crack. S * * S.
SEM studies have shown that repeated blow drying or use of curling tongs/flat irons can cause cuticular compression, cuticular disintegration, radial and axial cracking and scale edge chipping (Schweid. B. and G. Martino (2004), "How thermal protection is made possible with sodium polystyrene sulfonate" S.O.F.W.-Journal 130(8): 36-40). Heat exposed hair has also been shown to have a lower dynamic contact angle as cuticle lipids are damaged and removed (Schweid, and Martino (2004).
The effects of thermal treatments, such as curling tongs and straightening irons, on human hair were investigated by McMullen and Jachowicz (McMullen, R. and J. Jachowicz (1998), "Thermal degradation of hair I. Effect of curling irons", and "Thermal degradation of hair II. Effect of selected polymers and surfactants", Journal of Cosmetic Science 49(4): 223-256). Their work showed that heat treatments of between 130 and 164°C resulted in: a decomposition of chromophores, specifically tryptophan and its oxidation products (kynurenines); an increase in yellowness of white hair or a simultaneous yellowing and darkening of bleached hair; and an increase in combing forces. The knock-on' consequences of heat styling damage are also reduced moisture regain, secondary grooming damage (i.e. from brushing and S...
S *SSS
combing), increased fibre stiffness and decreased fibre mechanical strength (Streuli, * .55 * S *: D. C., L. C. Foltis, et al. (2002), "Style savers" Global Cosmetic Industry (January): *SS* * 30-32). *
S SS*S
Many substances have been investigated as heat protection agents, for example humectants able to retard water evaporation, such as glycerine, propylene glycol and hydrolysed wheat protein polysiloxane copolymer. These have been claimed to be able to reduce cuticle cracking on blow-drying (Gamez-Garcia 1998). Interestingly, however, simple occlusive agents oil and silicone oil had no effect, despite being widely known to slow water loss on blow drying.
Hydrolysed wheat protein (Hydrotriticum 2000, Croda) has been shown by fluorescence spectroscopy, combing analysis, and texture analysis with a dual-cantilever bending accessory, to reduce damage from curling irons (McMullen and Jachowicz 1998). Further, hydrolysed wheat protein PG.-propyl silanetriol (Crodazone W), applied in shampoo or conditioner, has been shown to reduce cuticle crack formation caused by blow-drying (Crodazone W: "Prevention of hair cutical damage from thermal stresses (formulated systems)" Croda technical note).
Sodium Polystyrene Sulfonate (Flexan II) has been shown to reduce heat damage from a curling iron as determined by SEM of the cuticle surface and dynamic contact angle measurements (Schweid and Martino 2004). It is believed to form a protective film on the hair surface, which is stable to well above 150°C.
Quaternium-70 (Ceraphyl 70) and polyquaternium-11 (Gafquat 75 SN) have been * shown to protect hair from damage from blow drying whilst brushing the hair (Streuli, *.S.
Foltis et al. 2002). The authors speculate that the quats provide a barrier film coating
S *.
* 20 and lubricating the hair. Quaternium-70 and the cationic polymer PVPIDMAPA :: acrylates copolymer (Styleze CC-b, ISP) have also been shown by fluorescence * spectroscopy, combing analysis, and texture analysis to prevent damage from curling irons (McMullen and Jachowicz 1998).
The styling polymer sodium PEG-40 maleate/styrene sulfonate copolymer (MiruStyle X-HP, Croda) has been claimed to prevent damage from heating up to 220°C.
Protection effects are supported with 3D-SEM, combing and flexabrasion data.
The conditioning agent triquatemary polydimethyl siloxane (Abil T Quat 60, Evonik) 5. is claimed to provide heat protection. Protection effects are supported with DSC data which show a reduced change in keratin denaturation temperature after treatment with a rinse-off conditioner containing Abil T Quat 60 (supplier data).
Many of the marketed heat protection sprays contain at least one of the ingredients listed above, and therefore offer some degree of protection to the hair. However, each one is formulated as either an aqueous spray or an ethanol/water spray.
A limited number of patent applications exist covering heat styling protection. For example, Croda and ISP disclose polymers for added heat protection of hair WO 2008/009907-A and WO 2000/78269-A. Henkel WO 2002/07686-A describes the use of carbohydrates (mono-, poly-or oligosaccharides) for heat protection of S.* ** hair. L'Oreal WO 2002/03937-A describes the use of monosaccharide sugars and *.* S..
* derivatives for heat protection. * sSS
S 5.5 S..
* 20 Further applications disclose full compositions, e.g. Playtex Prod Inc disclose a two **.* phase heat protection product in US 5756106-A. Schwartzkopf (Henkel) disclose a * heat protection product that contains a fibre active (e.g. panthenol) and a conditioning agent in WO 99/11224-A. Unilever disclose a shampoo with heat styling protection ingredients in WO 99/ 17713-A. Again, however, all of these compositions contain water.
According to a first aspect, the invention provides a fluid composition for application to hair ahead of heat styling with a straightening iron, curling tong, hair dryer or similar device, said composition comprising a solvent, wherein the composition comprises less than 5% by weight of water.
According to a second aspect, the invention provides a hair product comprising the above-described fluid composition, wherein the hair product comprises less than 5% by weight of water.
According to third and fourth aspects, the invention provides for use of a fluid composition as a hair product, and for use of a fluid composition or hair product to prevent damage to hair during heat styling.
*. According to a fifth aspect, the invention provides a method of styling hair
S
* comprising the sequential steps of (i) applying a fluid composition or a hair product to **** the (preferably dry) hair, and (ii) styling hair by application of heat. *.S * 20
The above-described invention reduces damage caused to hair by heat styling, * particularly with straightening irons, curling tongs and hair dryers. Without wishing to be bound by theory, it is believed that this is due to the reduction in the amount of water in the fluid composition and/or hair product, such that styling is effected on dry hair. This effect has not previously been recognised or harnessed.
In detail, it has now been evidenced that heat styling damage (created by straightening irons, hair dryers, curling tongs and the like) is significantly greater in wet' hair versus dry' hair. In our experiments, hair swatches were either dried for 48h over calcium chloride (dessicant) ahead of treatment with straightening irons, or immersed in tap water for 15 minutes. Swatches were heat treated with a GHD straightening iron (175-185°C) for 5 seconds. Treatments were repeated 12 times. Analysis of the treated hair with a light microscope clearly showed that structural damage was greatest in the wet' hair. Changes in the medulla and cortex of hair fibres were clearly visible in wet' hair, whilst they were absent in dry' hair.
The insight that water can accelerate heat styling damage has provided the stimulus for this invention, a dry' heat protection spray.
Additional advantages provided by the present invention include fast evaporation after * : application. This means that there is less crackling' when straightening irons or the like are applied. A nasty crackling' sound is common with aqueous products and is * *** * 20 caused by the boiling and steaming of the water under the hot irons. Another advantage is easier style generation. Water is well known to make hair more flexible * and to break-down style. A dry' heat protection spray, unlike a traditional aqueous product, would, therefore, not destroy any style created in the blow-drying step, immediately before the heat styling.
Looking at the present invention in more detail, it is preferred that the fluid composition is liquid. Most preferably it is able to be sprayed onto the hair. Spray devices suitable for use in the hair product could be, for example, a pump spray or an aerosol spray.
The composition is for example used to prevent damage from heated styling appliances such as straightening irons, hair dryers, curling tongs and the like. The composition should preferably be able to protect against damage caused by heating hair to temperatures ranging from 60°C to 300°C, more preferably to temperatures ranging from 170-230°C.
Preferably the composition comprises a non-volatile hair conditioning agent, and this is preferably included from 0.1% to 20% by weight of the fluid composition (excluding propellants in the case of aerosol products), more preferably from 1% to 5% by weight. *
* The non-volatile hair conditioning agent should enhance hair smoothness, softness and shine, and/or reduce hair fizz and flyaway. Ideally, it should also have heat styling and/or heat protection benefits. It could also have hair style hold benefits.
: ;: The non-volatile hair conditioning agent is preferably a silicone polymer, a silicone polymer derivative (e.g. with cationic side chains, or polyethoxylate side chains), silicone and hydrocarbon block or graft co-polymer, a cationic polymer based on a polysaccharide or protein back-bone, a cationic polymer based on a synthetic hydrocarbon back-bone, a cationic surfactant, or mixtures thereof.
The non-volatile hair conditioning agent would preferably be a cationic surfactant (e.g. quaternium-70), and/or a cationic silicone polymer derivative (e.g amodimethicone), and/or a silicone and hydrocarbon block or graft co-polymer (e.g. triquatemary polydimethyl siloxane and/or Bis PEGIPPG 20/20 dimethicone).
Preferably, blends of these ingredients would be used.
Preferably the composition comprises a hair styling polymer, and this is preferably included from 0.0 1% to 20% by weight of the fluid composition (excluding propellants in the case of aerosol products), more preferably from 1% to 10% by weight, most preferably from 2% to 6% by weight.
The hair styling polymer should hold hair in style after straightening. Preferably, it should also have heat protection benefits, and/or resistance to environmental humidity. The styling polymer is preferably a polysaccharide or protein based * . polymer, a synthetic hydrocarbon based polymer, a synthetic hydrocarbon based block copolymer, or mixtures thereof.
S *sS
The hair styling polymer would preferably be a block copolyrner, more preferably a * I * II. . copolymer of a vinylpyrrolidone and 1-2 other monomer umts, most preferably vinylacetate and one or both of a dimethylaminopropylamide (DMAPA) acrylate (e.g N-(3-(dimethylamino)propyl)-2-methyl-2-propenamjde) or a DMAPA acrylate derivative (e.g. I -dodecanaminium N,N dimethyl-N-(3-((2-methyl-1 -oxo-2-propenyl)amino)propyl)-chloride). Preferably, blends of these ingredients would be used.
The solvent should be volatile, approved for cosmetic use, and should dry rapidly after application to the hair. The solvent would, preferably, be ethanol and/or a cyclomethicone (e.g. cyclopentasiloxane), but could also be propylene glycol, isopropyl alcohol, dimethoxymethane, petroleum distillate, isoparaffin, isododecane, isohexadecane, PPG-3 benzyl ether myristate, isostearyl neopentanoate, isotridecyl isononanoate and the like. In the case of aerosol products, highly volatile liquids and gases would be used as propellants.
The water content of the formulation (i.e. the fluid composition and/or the hair product) should be as low as possible, preferably below 5% by weight of the fluid composition, more preferably below 3%, even more preferably below 1% and most preferably below 0.5% by weight. Ideally the formulation contains substantially no ** water, i.e. no water is detectable immediately after manufacture using standard * measurement techniques. S... *5S* S..
* 20 Optionally, the product would also contain IJV filters to provide protection against hair damage and colour fade. The UV filters might include ethylhexyl methoxycinnamate, benzophenones, zinc oxide, polysilicone-19, polyamide-2, polyquaternium-15, dimethylpabamidopropyl laurdimonium tosylate, natural sunscreens or similar materials.
Optionally, the product would also contain antioxidants to provide protection against chemical damage to the hair from UV radiation and heat styling. Antioxidants might include vitamins C and E, derivative forms of vitamins C and E (e.g. tocophereol acetate or ascorbyl palmitate), polyphenols, chinones, flavonoides, rosemary extract, oregano extract, green tea extract, thyme extract, celery extract, coriander extract, sage extract and rosehip extract or similar materials.
Optionally, the product would also contain one or more fragrances as known in the art.
The present invention is illustrated by reference to the example formulations A and B, as shown in table 1. The formulations A and B are preferably presented as a pump-spray product but could also be presented as an aerosol product. As is known in the art, aerosol products would require an added propellant in order to function. * I I...
S
S..... * 20 S... S... S..
S
S
**Ss*S * . S. S
S S S 5.
* . S S S * . S. * .. S S S S S * S S * S S*S *S* S S S * . . . . I * S.. *SS * SS* S
Table 1
________________________________________ _________________________ ____________ _____________________ _____________________
INCI name Trade Name (supplier) %w/w active Example Formula A Example Formula B as supplied %w/w % w/w %wlw % wiw ___________________________________ ______________________ __________ added active added acve VPNA Copolymer and ethanol PVPNA E-735 (ISP) 50 8.00 4.00 8.00 4.00 Quatemium-70 and propylene glycol Ceraphyl 70 (ISP) 50 2.40 1.20 0.00 0.00 Bis PEG/PPG 20/20 dimethicone ABIL B 8832 (Evonik) 100 1.00 1.00 0.00 0.00 Amcdimethicorie DC 2-8566(00w Coming) 100 0.00 0.00 2.00 2.00 Frrance ____________________ 100 1.00 1.00 1.00 1.00 Ethanol ____________________ 100 87.60 ________ 89.00 ________ The benefits of the present invention are proven through a comparison of the thermal damage created by straightening irons on hair pretreated with formulation A (from Table 1), or a water-based version of formulation A (Awet). This is illustrated in Figure 1.
Aet was made by replacing ethanol with water, and adding 0.07% Kathon CG� (methylchloroisothiazolinone and methylisothiazolinone, 1.5%, in water) as a preservative.
For this experiment fine density, light brown, virgin hair (20 cm in length) was purchased from International Hair Importers & Products Inc. (Glendale, New York, USA). Hair was cut into 1.5 cm wide tresses (approximately 1-2 g in weight, including the bindings). Hair tresses were dried for 2 days in a glass dessicator over calcium chloride at room-temperature before starting the study.
0.lmJ of product was applied to each hair tress before heat treatment. Tresses were S...
***. then left to dry for 2 minutes before applying the straightening irons. Tresses were * heat treated with ghd TV� straightening irons with 2 cm wide ceramic plates at 175-S...
*..: 185°C (ghd UK, Silsden, West Yorkshire, UK). The hair was treated with S..
straightening irons for 5 seconds. After each heat treatment, tresses were washed with a standard shampoo (Charles Worthington Brilliant Shine� Shampoo, PZ Cussons * (UK) Ltd, Stockport, Cheshire, UK). Cleaned tresses were air dried, and then put back into the dessicator. Treatments were repeated 12 times. Each tress, therefore, was heat treated, in total, for 60 seconds.
For tensile testing, fibres were permanently mounted with a 10 mm gauge length in PVC-lined brass crimps. The cross-sectional area of each fibre was measured using the Fiber Dimensional Analysis System (FDAS), which incorporates a Mitituyo laser scanner (Dia-Stron Ltd, Andover, Hampshire, UK). Crimped fibres were loaded into the MTT675 cassette (Dia-Stron Ltd) and then equilibrated at 80% R.H. overnight.
The fibres were then extended to break at 12.5 mm/minute (40% strain rate/minute), using the MTT675 Automated Tensile Tester (Dia-Stron Ltd).
As shown in Figure 1, the change in Young's modulus caused by heat treatment was much greater in hair treated in the presence of the water-based heat protection spray, in comparison to the ethanol based product, A. These data confirm that a water-free product provides better protection for the hair. * * ****
S
S..... * . S... S... a
S
S..... * S *5 S
S S S

Claims (13)

  1. Claims 1. A fluid composition for application to hair ahead of heat styling with a straightening iron, curling tong, hair dryer or similar type of device, said composition comprising a solvent, wherein the composition comprises less than 5% by weight of water.
  2. 2. A fluid composition according to claim 1, wherein said composition comprises less than 1% by weight of water.
  3. 3. A fluid composition according to claim 1, wherein said composition comprises less than 0.5% by weight of water.
  4. 4. A fluid composition according to any preceding claim, wherein said solvent is selected from the group consisting of ethanol, a cyclomethicone, propylene glycol, isopropyl alcohol, dimetboxymethane, petroleum distillate, isoparaffin, isododecane, isohexadecane, PPG-3 benzyl ether myristate, isostearyl neopentanoate, isotridecyl isononanoate and mixtures thereof.
  5. 5. A fluid composition according to claim 4, wherein the solvent is a mixture of ethanol and a cyclomethicone.
    *
  6. 6. A fluid composition according to any preceding claim, wherein the *..: 20 composition additionally comprises a non-volatile hair conditioning agent selected * from the group consisting of silicone polymers, silicone polymer derivatives, silicone and hydrocarbon block or graft co-polymers, cationic polymers based on a * polysaccharide or protein back bone, cationic polymers based on a synthetic hydrocarbon backbone, cationic surfactants, or mixtures thereof.
  7. 7. A fluid composition according to any preceding claim, wherein the composition additionally comprises a hair styling polymer selected from a polysaccharide or protein based polymer, a synthetic hydrocarbon based polymer, a synthetic hydrocarbon based block-copolymer, or mixtures thereof.
  8. 8. A fluid composition according to any preceding claim wherein the composition additionally comprises UV filters, antioxidants and/or fragrance.
  9. 9. A hair product comprising the fluid composition according to any preceding claim, wherein the hair product comprises less than 5% by weight of water.
  10. 10. Use of a fluid composition according to any of claims 1-8 as a hair product.
  11. 11. Use of a fluid composition according to any of claims 1-8, or a hair product according to claim 9, to prevent damage to hair during heat styling.
  12. 12. Use according to claim 10, wherein said hair is dry hair.
  13. 13. A method of styling hair comprising the sequential steps of: (i) applying a fluid composition according to any of claims 1-8, or a hair product according to claim 9, to hair (ii) styling this hair by application of heat. *.SS * * ****S..... * SS I... * *.*SS * *SS S S S *�
GB1006419A 2009-04-22 2010-04-16 Fluid composition for application to hair ahead of heat styling Withdrawn GB2468790A (en)

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Cited By (1)

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Publication number Priority date Publication date Assignee Title
DE102010048056A1 (en) * 2010-10-12 2012-04-12 Beiersdorf Ag Hair treatment agent, which gives particularly long-lasting shine

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Publication number Priority date Publication date Assignee Title
DE102011089404A1 (en) * 2011-12-21 2013-06-27 Henkel Ag & Co. Kgaa Use of at least one anteiso (C8-C30) carboxylic acid for moisture resistant heat styling
DE102013224869A1 (en) 2013-12-04 2015-06-11 Henkel Ag & Co. Kgaa Longer Lasting Hairspray
DE102022202842A1 (en) * 2022-03-23 2023-09-28 Henkel Ag & Co. Kgaa Hair conditioning agent for straightening hair

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US20020155962A1 (en) * 2001-01-17 2002-10-24 Cincotta Joseph J. Nonaqueous hair styling composition and method of use
US20030143180A1 (en) * 2000-07-18 2003-07-31 L'oreal Hairstyling composition which makes possible remodelling of the hairstyle and process for remodelling the hairstyle using such a composition
JP2007051078A (en) * 2005-08-17 2007-03-01 Kanebo Home Products Kk Non-aqueous hair cosmetic
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US20030143180A1 (en) * 2000-07-18 2003-07-31 L'oreal Hairstyling composition which makes possible remodelling of the hairstyle and process for remodelling the hairstyle using such a composition
US20020155962A1 (en) * 2001-01-17 2002-10-24 Cincotta Joseph J. Nonaqueous hair styling composition and method of use
JP2007051078A (en) * 2005-08-17 2007-03-01 Kanebo Home Products Kk Non-aqueous hair cosmetic
WO2008061985A1 (en) * 2006-11-23 2008-05-29 L'oreal Cosmetic composition comprising at least one aprotic hydrocarbon-based volatile solvent
WO2008112200A1 (en) * 2007-03-13 2008-09-18 Carson Product Development, Inc. Cationic protein and silicone polymers
WO2010080482A2 (en) * 2008-12-18 2010-07-15 Momentive Performance Materials Inc. Composition comprising at least two different cycloalkylmethicones and use thereof

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Publication number Priority date Publication date Assignee Title
DE102010048056A1 (en) * 2010-10-12 2012-04-12 Beiersdorf Ag Hair treatment agent, which gives particularly long-lasting shine

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GB0906962D0 (en) 2009-06-03
GB201006419D0 (en) 2010-06-02
WO2010122286A2 (en) 2010-10-28
WO2010122286A3 (en) 2011-11-03

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