WO2007065522A1 - Hair straightening composition comprising urea - Google Patents

Hair straightening composition comprising urea Download PDF

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Publication number
WO2007065522A1
WO2007065522A1 PCT/EP2006/010714 EP2006010714W WO2007065522A1 WO 2007065522 A1 WO2007065522 A1 WO 2007065522A1 EP 2006010714 W EP2006010714 W EP 2006010714W WO 2007065522 A1 WO2007065522 A1 WO 2007065522A1
Authority
WO
WIPO (PCT)
Prior art keywords
hair
hydroxide
urea
straightening
composition
Prior art date
Application number
PCT/EP2006/010714
Other languages
French (fr)
Inventor
Paul Carpenter
Cheryl Anne Taylor
David Tetard
Original Assignee
Unilever Plc
Unilever Nv
Hindustan Unilever Limited
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
Application filed by Unilever Plc, Unilever Nv, Hindustan Unilever Limited filed Critical Unilever Plc
Priority to DE602006021616T priority Critical patent/DE602006021616D1/en
Priority to US12/086,092 priority patent/US8673273B2/en
Priority to EP06840928A priority patent/EP1960056B1/en
Priority to PL06840928T priority patent/PL1960056T3/en
Priority to AT06840928T priority patent/ATE506989T1/en
Priority to BRPI0620478A priority patent/BRPI0620478B1/en
Publication of WO2007065522A1 publication Critical patent/WO2007065522A1/en
Priority to ZA2008/04202A priority patent/ZA200804202B/en

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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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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
    • A61Q5/04—Preparations for permanent waving or straightening the hair

Definitions

  • hair relaxers which can relax or straighten naturally curly or kinky hair. Hair relaxers may either be applied in a hair salon by a professional or in the home by the individual consumer.
  • Hair fibre a keratinous material, comprises proteins
  • polypeptides (polypeptides) . Many of the polypeptides in hair fibres are bonded together or cross-linked with disulfide bonds
  • a disulfide bond may be formed from the reaction of two sulfhydryl groups (-SH) , one on each of two cysteine residues, which results in the formation of a cystine residue.
  • a cystine residue comprises a cross-link of the formula -CH2-S-S-CH2- between 2 polypeptides.
  • the reaction is generally terminated by rinsing and/or the application of a neutralizing composition.
  • the reaction with the alkaline agent is normally initiated by hydroxide ions.
  • hydroxide ions initiate a reaction in which a cystine cross-link (-CH2-S-S-CH2-) is broken and a
  • lanthionine cross-link (-CH2-S-CH2-) is formed.
  • lanthionizing is used when one skilled in the art refers to the relaxing or straightening of keratin fibres by hydroxide ions.
  • compositions and methods to relax keratin fibres which preserve the relaxing efficiency of hydroxide ion yet do not cause the negative attributes associated with lanthionized hair.
  • the present invention in one aspect, provides an aqueous based hair straightening composition having a pH from 12 to 14 comprising
  • a method for straightening hair comprising applying to the hair a composition described above.
  • a further aspect of this invention is the use of the urea in a hydroxide based straightening system to enhance the straightening activity and/or to mitigate hair damage.
  • the straightening composition comprises urea.
  • the level of the urea compound ranges from 0.5 wt% to 20 wt% of the total composition, more preferably from 1 wt% to 15 wt%, most preferably from 3 to 10 wt%.
  • Any suitable hydroxide generator may be used in the
  • lithium hydroxide preferred are lithium hydroxide, potassium hydroxide and guanidine hydroxide.
  • Sodium hydroxide is particularly preferred. In some cases, such as with - A - guanidine hydroxide, it is preferred if the hydroxide is preferred in situ.
  • the hydroxide generator is preferably present at levels ranging from 0.1 wt% to 8 wt% of the total composition, more preferably from 0.5 wt% to 3 wt%.
  • the weight ratio urea hydroxide generator is from 20:1 to 2:1, more preferably from 12:1 to 3:1.
  • composition is in an aqueous base.
  • base compositions comprising an oil-in-water emulsion.
  • compositions of the invention can be chosen from solvents such as alcohol and water; preservatives; perfumes; UV filters; active hair care agents; plasticizers; anionic, cationic, amphoteric, nonionic, and zwitterionic surfactants; hair conditioning agents such as silicone fluids, fatty esters, fatty alcohol, fatty chain hydrocarbons, emollients, lubricants, and penetrants such as lanolin compounds, protein hydrolysates, and other protein derivatives; anionic, cationic,
  • amphoteric, nonionic, and zwitterionic polymers include butyl-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-styrene-sulfonic-sulfonic, and zwitterionic polymers; dyes;
  • tints bleaches; reducing agents; pH adjusting agents;
  • Products of the invention may further comprise organic nucleophiles chosen from basic amino acids such as lysine, amines, alcohols, and mercaptans and derivatives thereof. Ionic form (such as lysine) and/or in the form of
  • an ammonium form such as lysine hydrochloride
  • a carboxylate form such as sodium lysinate
  • the preferred product form is a cream.
  • the product is in the form of a kit
  • the first part comprises the hydroxide components and is preferably formulated as a cream.
  • the second part comprises the urea/urea based additive and may be in a liquid or solid form.
  • urea/urea based additive could be used either as neat active or as a diluted slurry, dispersion or solution.
  • the two parts of the kit are mixed immediately before application to the hair.
  • immediate before application means approximately 5 minutes or less before application.
  • Polawax GP200 is a mixture of PEG-20 Stearate and
  • Cetearyl alcohol in a 1 to 4 ratio Cetearyl alcohol in a 1 to 4 ratio.
  • a set of switches were treated with the relaxer cream containing 2% sodium hydroxide (Example A) a second set of switches were treated with 1.5% sodium hydroxide and 8 % urea. The switches were treated consecutively for a total of 4 applications. Each cycle consisted of treatment with the relaxer cream for 20-30 minutes, rinsing, shampooing, rinsing, and blot drying. After the fourth application the switches were allowed to dry overnight (18hrs) in controlled conditions 25°C 50% RH.
  • the weight of the switches was recorded.
  • the switches were mounted in an automatic combing device and subjected to a total of 6 hours dry combing, the weight of each switch was recorded after each hour.
  • the % breakage is calculated as the weight at a given time/initial weight x 100.
  • the straightening data was assessed by the mean absolute curvature (mm ) of the hair. The greater the curvature the curlier the hair.

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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)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

An aqueous based hair straightening composition having a pH from 12 to 14 comprising i)an hydroxide ion generator; and ii) from 0.5 wt% to 20 wt% of the total composition of urea in which the weight ratio of urea to hydroxide generator is greater than 1:1.

Description

HAIR STRAIGHTENING COMPOSITION COMPRISING UREA
Field of the Invention The present invention relates to compositions for
straightening hair.
Background and Prior Art Straightening or relaxing the curls of very curly hair is thought to increase the manageability and ease of styling of such hair. There is an increasing demand for the hair care products referred to as "hair relaxers, " which can relax or straighten naturally curly or kinky hair. Hair relaxers may either be applied in a hair salon by a professional or in the home by the individual consumer.
Hair fibre, a keratinous material, comprises proteins
(polypeptides) . Many of the polypeptides in hair fibres are bonded together or cross-linked with disulfide bonds
(-S-S-) . A disulfide bond may be formed from the reaction of two sulfhydryl groups (-SH) , one on each of two cysteine residues, which results in the formation of a cystine residue. A cystine residue comprises a cross-link of the formula -CH2-S-S-CH2- between 2 polypeptides.
While there are other types of bonds which occur between the polypeptides in hair fibres, such as ionic (salt) bonds, the permanent curling or the shape of the hair is essentially dependent on the disulfide bonds of cystine residues. As a result, relaxing or straightening of hair can be achieved by disrupting the disulfide bonds of the hair fibres with an alkaline agent or a -2 reducing agent. The chemical disruption of disulfide bonds by an alkaline agent is usually combined with mechanical straightening of the hair, such as combing, and straightening generally occurs due to changes of the relative positions of opposite
polypeptide chains within the hair fibre. The reaction is generally terminated by rinsing and/or the application of a neutralizing composition. The reaction with the alkaline agent is normally initiated by hydroxide ions.
Specifically, hydroxide ions initiate a reaction in which a cystine cross-link (-CH2-S-S-CH2-) is broken and a
lanthionine cross-link (-CH2-S-CH2-) is formed.
Consequently, the term "lanthionizing" is used when one skilled in the art refers to the relaxing or straightening of keratin fibres by hydroxide ions.
Hair that has been lanthionized using hydroxide ion
generating compositions frequently feels harsh and can break during grooming. Thus, there is still a need for compositions and methods to relax keratin fibres which preserve the relaxing efficiency of hydroxide ion yet do not cause the negative attributes associated with lanthionized hair. Description of the Invention
The present invention, in one aspect, provides an aqueous based hair straightening composition having a pH from 12 to 14 comprising
i) an hydroxide ion generator; and
ii) from 0.5 wt% to 20 wt% of the total composition of urea in which the weight ratio of urea to hydroxide generator is greater than 1:1.
In another aspect of the invention, there is provided a method for straightening hair comprising applying to the hair a composition described above. A further aspect of this invention is the use of the urea in a hydroxide based straightening system to enhance the straightening activity and/or to mitigate hair damage.
Detailed Description of the invention
The straightening composition comprises urea.
The level of the urea compound ranges from 0.5 wt% to 20 wt% of the total composition, more preferably from 1 wt% to 15 wt%, most preferably from 3 to 10 wt%.
Any suitable hydroxide generator may be used in the
composition, preferred are lithium hydroxide, potassium hydroxide and guanidine hydroxide. Sodium hydroxide is particularly preferred. In some cases, such as with - A - guanidine hydroxide, it is preferred if the hydroxide is preferred in situ.
The hydroxide generator is preferably present at levels ranging from 0.1 wt% to 8 wt% of the total composition, more preferably from 0.5 wt% to 3 wt%.
It is preferred if the weight ratio urea hydroxide generator is from 20:1 to 2:1, more preferably from 12:1 to 3:1.
Other Constituents
It is preferred if the composition is in an aqueous base. Particularly preferred are base compositions comprising an oil-in-water emulsion.
Other constituents which can be used in the compositions of the invention can be chosen from solvents such as alcohol and water; preservatives; perfumes; UV filters; active hair care agents; plasticizers; anionic, cationic, amphoteric, nonionic, and zwitterionic surfactants; hair conditioning agents such as silicone fluids, fatty esters, fatty alcohol, fatty chain hydrocarbons, emollients, lubricants, and penetrants such as lanolin compounds, protein hydrolysates, and other protein derivatives; anionic, cationic,
amphoteric, nonionic, and zwitterionic polymers; dyes;
tints; bleaches; reducing agents; pH adjusting agents;
sunscreens; and thickening agents. Products of the invention may further comprise organic nucleophiles chosen from basic amino acids such as lysine, amines, alcohols, and mercaptans and derivatives thereof. Ionic form (such as lysine) and/or in the form of
derivatives thereof, e.g., an ammonium form (such as lysine hydrochloride) and/or a carboxylate form (such as sodium lysinate) .
The preferred product form is a cream.
In one aspect the product is in the form of a kit
consisting of two parts. The first part comprises the hydroxide components and is preferably formulated as a cream. The second part comprises the urea/urea based additive and may be in a liquid or solid form. The
urea/urea based additive could be used either as neat active or as a diluted slurry, dispersion or solution. The two parts of the kit are mixed immediately before application to the hair. In the context of this invention the term
"immediately before application" means approximately 5 minutes or less before application.
The invention will now be illustrated by the following non- limiting Examples. Examples of the invention are
illustrated by a number, comparative examples are
illustrated by a letter. -Relaxer Formulation With 2% Hydroxide
Figure imgf000007_0001
* Polawax GP200 is a mixture of PEG-20 Stearate and
Cetearyl alcohol in a 1 to 4 ratio.
Table 2
Figure imgf000008_0001
A set of switches were treated with the relaxer cream containing 2% sodium hydroxide (Example A) a second set of switches were treated with 1.5% sodium hydroxide and 8 % urea. The switches were treated consecutively for a total of 4 applications. Each cycle consisted of treatment with the relaxer cream for 20-30 minutes, rinsing, shampooing, rinsing, and blot drying. After the fourth application the switches were allowed to dry overnight (18hrs) in controlled conditions 25°C 50% RH.
The weight of the switches was recorded. The switches were mounted in an automatic combing device and subjected to a total of 6 hours dry combing, the weight of each switch was recorded after each hour. The % breakage is calculated as the weight at a given time/initial weight x 100.
Figure imgf000009_0001
The straightening data was assessed by the mean absolute curvature (mm ) of the hair. The greater the curvature the curlier the hair.
Figure imgf000010_0001
It is thus demonstrated that urea increases the
effectiveness of a hydroxide based relaxing system while mitigating the damage caused by the hydroxide.

Claims

1. An aqueous based hair straightening composition having a pH from 12 to 14 comprising
i) an hydroxide ion generator; and
ii) from 0.5 wt% to 20 wt% of the total composition of urea in which the weight ratio of urea to hydroxide generator is greater than 1:1.
2. A hair straightening composition according to any
preceding claim in which the hydroxide ion generator is sodium hydroxide.
3. A hair straightening composition according to any
preceding claim in which the levels of compound ii) range from 1 wt% to 15 wt% of the total composition.
4. A hair straightening composition according to any
preceding claim in which the levels of hydroxide ion generator range from 0.5 wt% to 3 wt% of the total composition.
5. A hair straightening composition according to any
preceding claim in which weight ratio of compound ii) to hydroxide generator is from 12:1 to 3:1.
6. A method for lanthionizing keratin fibres to achieve
relaxation of said keratin fibres in which a composition according to any preceding claim is applied to the hair.
7. Use of urea:
Figure imgf000012_0001
in a hydroxide based straightening system to enhance the straightening of hair.
Use of urea:
'N N
I I
R 2 R3 in a hydroxide based straightening system to mitigate hair damage.
PCT/EP2006/010714 2005-12-07 2006-11-06 Hair straightening composition comprising urea WO2007065522A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
DE602006021616T DE602006021616D1 (en) 2005-12-07 2006-11-06 Urea-containing hair straightening composition
US12/086,092 US8673273B2 (en) 2005-12-07 2006-11-06 Hair straightening composition comprising urea
EP06840928A EP1960056B1 (en) 2005-12-07 2006-11-06 Hair straightening composition comprising urea
PL06840928T PL1960056T3 (en) 2005-12-07 2006-11-06 Hair straightening composition comprising urea
AT06840928T ATE506989T1 (en) 2005-12-07 2006-11-06 HAIR STRAIGHTENING COMPOSITION CONTAINING UREA
BRPI0620478A BRPI0620478B1 (en) 2005-12-07 2006-11-06 hair straightening composition and method for lantionizing keratin fibers
ZA2008/04202A ZA200804202B (en) 2005-12-07 2008-05-15 Hair straightening composition comprising urea

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP05257519.8 2005-12-07
EP05257519 2005-12-07

Publications (1)

Publication Number Publication Date
WO2007065522A1 true WO2007065522A1 (en) 2007-06-14

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PCT/EP2006/010714 WO2007065522A1 (en) 2005-12-07 2006-11-06 Hair straightening composition comprising urea

Country Status (9)

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US (1) US8673273B2 (en)
EP (1) EP1960056B1 (en)
AT (1) ATE506989T1 (en)
BR (1) BRPI0620478B1 (en)
DE (1) DE602006021616D1 (en)
PL (1) PL1960056T3 (en)
RU (1) RU2424790C2 (en)
WO (1) WO2007065522A1 (en)
ZA (1) ZA200804202B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2939285A1 (en) * 2008-12-10 2010-06-11 Oreal Human or animal keratin fiber i.e. dry hair, treating method, involves exposing portion of keratin fiber to light pulse to provide residual deformation to fiber portion, which conserves cross-section in which fiber is drawn
WO2015090802A1 (en) * 2013-12-19 2015-06-25 Henkel Ag & Co. Kgaa Method for the shaping of keratin fibers

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1492078A1 (en) * 1964-11-19 1969-10-09 Oreal Process for permanent water-waving of hair and means for carrying out the process
DE1955823A1 (en) * 1969-11-06 1971-05-13 Wella Ag Method of stretching human hair
EP0200208A2 (en) * 1985-04-29 1986-11-05 Richardson-Vicks, Inc. Pantethine component for hair permanent waving
DE3543453A1 (en) * 1985-12-09 1987-06-11 Wella Ag METHOD FOR SIMULTANEOUSLY COLORING AND PERMANENTLY DEFORMING HAIR
JP2000229819A (en) * 1999-02-05 2000-08-22 Shiseido Co Ltd Composition for treating hair
EP1321124A2 (en) * 2001-12-22 2003-06-25 Henkel Kommanditgesellschaft auf Aktien Use of selected short-chain carboxylic acids
JP2003212737A (en) * 2002-01-22 2003-07-30 Hoyu Co Ltd Hair treatment composition

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3650280A (en) * 1969-12-03 1972-03-21 David Roberts Cosmetic treatment of hair with thiourea or urea and glyoxal
US5338540A (en) * 1985-02-04 1994-08-16 Conopco, Inc. Hair waving and straightening composition
US4793994A (en) * 1986-06-27 1988-12-27 Gaf Corporation Compositions used in permanent structure altering of hair
US4992267A (en) * 1988-04-28 1991-02-12 Johnson Products Co., Inc. Hair straightening composition and system
US5206385A (en) * 1992-01-24 1993-04-27 Isp Investments Inc. Urea-hydrogen peroxide-polyvinylpyrrolidone process
US7468180B2 (en) * 2001-08-20 2008-12-23 L'oreal, S.A. Compositions comprising at least one hydroxide compound and at least one oxidizing agent, and methods to straighten curly hair

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1492078A1 (en) * 1964-11-19 1969-10-09 Oreal Process for permanent water-waving of hair and means for carrying out the process
DE1955823A1 (en) * 1969-11-06 1971-05-13 Wella Ag Method of stretching human hair
EP0200208A2 (en) * 1985-04-29 1986-11-05 Richardson-Vicks, Inc. Pantethine component for hair permanent waving
DE3543453A1 (en) * 1985-12-09 1987-06-11 Wella Ag METHOD FOR SIMULTANEOUSLY COLORING AND PERMANENTLY DEFORMING HAIR
JP2000229819A (en) * 1999-02-05 2000-08-22 Shiseido Co Ltd Composition for treating hair
EP1321124A2 (en) * 2001-12-22 2003-06-25 Henkel Kommanditgesellschaft auf Aktien Use of selected short-chain carboxylic acids
JP2003212737A (en) * 2002-01-22 2003-07-30 Hoyu Co Ltd Hair treatment composition

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 2000, no. 11 3 January 2001 (2001-01-03) *
PATENT ABSTRACTS OF JAPAN vol. 2003, no. 11 5 November 2003 (2003-11-05) *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2939285A1 (en) * 2008-12-10 2010-06-11 Oreal Human or animal keratin fiber i.e. dry hair, treating method, involves exposing portion of keratin fiber to light pulse to provide residual deformation to fiber portion, which conserves cross-section in which fiber is drawn
WO2015090802A1 (en) * 2013-12-19 2015-06-25 Henkel Ag & Co. Kgaa Method for the shaping of keratin fibers

Also Published As

Publication number Publication date
EP1960056B1 (en) 2011-04-27
US8673273B2 (en) 2014-03-18
BRPI0620478A2 (en) 2011-11-16
RU2424790C2 (en) 2011-07-27
ZA200804202B (en) 2009-09-30
PL1960056T3 (en) 2011-09-30
RU2008127399A (en) 2010-01-20
EP1960056A1 (en) 2008-08-27
BRPI0620478B1 (en) 2015-09-15
DE602006021616D1 (en) 2011-06-09
ATE506989T1 (en) 2011-05-15
US20090252696A1 (en) 2009-10-08

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