US3661161A - Process for setting hair with polycondensable urea and thiourea compounds - Google Patents

Process for setting hair with polycondensable urea and thiourea compounds Download PDF

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US3661161A
US3661161A US881903A US3661161DA US3661161A US 3661161 A US3661161 A US 3661161A US 881903 A US881903 A US 881903A US 3661161D A US3661161D A US 3661161DA US 3661161 A US3661161 A US 3661161A
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Prior art keywords
hair
acid
composition
dihydroxyethylene
urea
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US881903A
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Gregoire Kalopissis
Henry Philippe De Beaulieu
Jean-Louis Abegg
Giuliana Ghilardi
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LOreal SA
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LOreal SA
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/95—Involves in-situ formation or cross-linking of polymers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00—Drug, bio-affecting and body treating compositions
    • Y10S424/01—Aerosol hair preparation
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00—Drug, bio-affecting and body treating compositions
    • Y10S424/02—Resin hair settings

Definitions

  • the setting with standard lotions lacks luster and body.
  • the hair in this case has a rather dull appearance and the hold of the coiffure does not resist successive modifications that are imposed on it, either by combing, or by the action of the wind and various atmospheric agents.
  • the present invention relates to a composition and a process for setting hair, particularly suitable for setting difficult" hair (i.e., fine or soft hair) making it possible to obtain improved results, both in regard to the holding of the setting and the luster and body of the hair after setting.
  • difficult hair i.e., fine or soft hair
  • compositions according to the present invention are characterized by the presence of a polycondensable compound that can polymerize in an acid medium, the polymerization being accelerated by adding heat, and giving rise to a resin fixed in a way very close to the keratin of the hair, which increases its body and holding.
  • the present invention has for its object the novel industrial product which constitutes a cosmetic composition making it possible in particular to set hair, characterized by the fact that it contains, in a standard cosmetic vehicle or base, at least one polycondensable compound corresponding to the following formula:
  • X represents an oxygen atom or a sulfur atom
  • R and R represent either a hydrogen atom or a lower alkyl radical and R and R represent either a hydrogen atom or a lower alkyl radical, it being understood that by lower alkyl radical is meant aliphatic chains having from one to four carbon atoms.
  • the polycondensable compounds are present in the composition in the amount of 0.5 to percent by weight and preferably in the amount of 2.4 to 5 percent.
  • composition according to the invention can advantageously be present in the form of an aqueous or hydroalcoholic solution. However, in particular embodiments, it can also be present in the form of a gel, cream or aerosol.
  • the composition also contains resins which are conventionally used in hair setting lotions such as polyvinyl pyrrolidone/vinyl acetate or vinyl acetate/crotonic acid copolymers.
  • resins which are conventionally used in hair setting lotions such as polyvinyl pyrrolidone/vinyl acetate or vinyl acetate/crotonic acid copolymers.
  • resins in the composition can be between 0.5 and 5 percent by weight.
  • the cosmetic composition can also contain an acid reacting compound acting as a catalyst, in a sufficient amount to bring the pH of the composition to a value between 1.5 and 5.
  • the acid reacting compounds can be inorganic acids such as sulfuric, hydrochloric, phosphoric acids, acid salts such as sodium and potassium monophosphates or organic acids such as acetic acid, citric acid,.lactic acid and formic acid.
  • composition according to the invention can, in: addition, contain any conventional ingredient that can be used in cosmetics such as a swelling agent, surfactant, dye and perfume.
  • the composition according'. to the invention is made in two parts, one of which contains the polycondensable compound whose formula is indicated above, while the other contains the cosmetic resin and the acid reacting compound.
  • the compositions according to the invention can be made up of a solid part containing. only the polycondensable compound, and a liquid part containing an aqueous or hydroalcoholic solution of an acid reacting compound, these two parts being intended to be mixed at the time of use.
  • said setting composition is in the form of a solution of the polycondensable compound not containing the acid reacting compound, the hair impregnated with said composition being rinsed before or after with an acid solution according to a process that will bedescribed below.
  • the present invention also has for its objecta novel process to set hair characterized by the fact that the hair is impregnated with a composition containing, in a conventional.
  • X represents an oxygen atom or a sulfur atom
  • R and R represent either a hydrogen atom or a lower alkyl radical
  • R 1 and R represent either a hydrogen atom or a lower alkyl radical, and the hair is given an acid rinse, either before or after impregnation with the composition mentioned above, the hair being rolled on setting rollers and dried with heat.
  • the hair is impregnated with a composition containing the polycondensable compounds described above, and whose pH has been brought, at the time of use, to a value between 1.5 and 5, by the addition of a sufficient amount of acid, and the hair is rolled on setting rollers and dried by heat.
  • acetate S 630 copolymer which is a white powder having a ratio of PVP to VA of 60:40 and having a specific gravity (25 C.) of 1.27 i 0.01 determined on the molten copolymer. Its K-value ranges between 30 and 50 wherein the K-value is a function of means molecular weight and is derived from the formula:
  • a cationic shampooing intended to bring its pH to a value close to 2.
  • a shampooing can have the following composition:
  • the hair is then put up in curlers and dried. There is obtained a setting presenting an excellent luster and satisfactory body.
  • oleic acid H moles QB.
  • paraffin oil 23 g. 4,5-dihydroxyethylene dimethylurea 0.5 g. acetic acid q.s.p. pH 3.5
  • R1N/ NRg (BH '1H ()R 6R wherein X is selected from the group consisting of oxygen and sulfur, R, R, R, and R each independently are selected from the group consisting of hydrogen and lower alkyl, said compound being present in amounts of 0.5 to l0 percent by weight of said composition, rinsing said hair with an aqueous acidic solution prior to or subsequent to impregnating the same with said composition, winding said hair on rollers and drying said hair.
  • said acidic aqueous solution consists essentially of an aqueous solution of a member selected from the group consisting of lactic acid, acetic acid, formic acid, citric acid, sulfuric acid, hydrochloric acid, phosphoric acid and sodium and potassium monophosphates, said member being present in amounts effective to polymerize said compound on said hair.
  • a process for setting hair comprising impregnating said hair with an effective amount of a composition comprising an aqueous solution of a polymerizable compound having the formula wherein X is selected from the group consisting of oxygen and sulfur, R, R, R and R each independently are selected from the group consisting of hydrogen and lower alkyl, present in amounts of 0.5 to 10 percent by weight of said composition and an acidic catalyst selected from the group consisting of lactic acid, acetic acid, formic acid, citric acid, sulfuric acid, hydrochloric acid, phosphoric acid and sodium and potassium monophosphates present in amounts sufiicient so that the pH of said composition is between 1.5 and 5, winding said hair on rollers and drying said hairv

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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)
  • Cosmetics (AREA)

Abstract

Hair is set by impregnating the same, in the presence of an acidic catalyst, with a polymerizable compound having the formula

WHEREIN X is oxygen or sulfur and R, R'', R1 and R2 each are hydrogen or lower alkyl, winding the hair on rollers and drying the hair.

Description

I United States Patent 1151 3,661,161
Kalopissis et al. 1 May 9, 1972 PROCESS FOR SETTING HAIR WITH 1 1 References Cited POLYCONDENSABLE UREA AND UNITED STATES PATENTS THIOUREA COMPOUNDS 3,079,297 2/1963 Van Loo ..8/1 16.2 X
[72] inventors: Gregoire Kalopissis; Henry Philippe De Beaulieui Jean'Louis g; Giuliana Primary Examiner-Jerome D. Goldberg Ghilardi, all f Paris France Assistant Examiner-Vera C. Clarke AtwmeyCushman, Darby & Cushman [73] Assignee: Societe Anonyme dite L'Oreal, Paris,
France [57 ABSTRACT Filedl D 3, 1969 Hair is set by impregnating the same, in the presence of an [21] A 1 No, 881 903 acidic catalyst, with a polymerizable compound having the pp formula X [30] Foreign Application Priority Data Dec. 4, 1968 Luxembourg ..51.454 R -llq 011- 52 us. 01 ..132/7, 8/127.51, 8/127.6, 1 424/010. 1, 424/D1G. 2, 424/47, 424 71 OR 511 1111. c1. ..A61k 7 10 521 Field of Search ..424/47, 71; 8/127.51, 127.6, wherein X en of Sulfur d R R1 an R2 are hydrogen or lower alkyl, winding the hair on rollers and drying the hair.
4 Claims, No Drawings PROCESS FOR SETTING HAIR WITH POLYCONDENSABLE UREA AND THIOUREA COMPOUNDS The present invention has for its object a novel composition and a novel process for setting hair.
It is known that the results obtained when hair is set with standard hair setting lotions often depend on the nature of the hair treated.
In some particular cases, for example, when very fine or soft hair is set, the setting with standard lotions lacks luster and body. The hair in this case has a rather dull appearance and the hold of the coiffure does not resist successive modifications that are imposed on it, either by combing, or by the action of the wind and various atmospheric agents.
The present invention relates to a composition and a process for setting hair, particularly suitable for setting difficult" hair (i.e., fine or soft hair) making it possible to obtain improved results, both in regard to the holding of the setting and the luster and body of the hair after setting.
The compositions according to the present invention are characterized by the presence of a polycondensable compound that can polymerize in an acid medium, the polymerization being accelerated by adding heat, and giving rise to a resin fixed in a way very close to the keratin of the hair, which increases its body and holding.
The present invention has for its object the novel industrial product which constitutes a cosmetic composition making it possible in particular to set hair, characterized by the fact that it contains, in a standard cosmetic vehicle or base, at least one polycondensable compound corresponding to the following formula:
wherein:
X represents an oxygen atom or a sulfur atom,
R and R represent either a hydrogen atom or a lower alkyl radical and R and R represent either a hydrogen atom or a lower alkyl radical, it being understood that by lower alkyl radical is meant aliphatic chains having from one to four carbon atoms.
In a preferred embodiment, the polycondensable compounds are present in the composition in the amount of 0.5 to percent by weight and preferably in the amount of 2.4 to 5 percent.
The composition according to the invention can advantageously be present in the form of an aqueous or hydroalcoholic solution. However, in particular embodiments, it can also be present in the form of a gel, cream or aerosol.
Of the polycondensable compounds that can be used, according to the invention, we can cite:
4,5 dihydroxyethylene urea, of the formula:
ll HN/ NH CH-41H Ha, I 4,5-dihydr0xyethy1ene thiourea, of the formula:
s II o HN NH CIICH no 0 n 4,5-1liliyrlroxyulliylmm tlimntliylurmr, of the formula:
Ulla
C }IN/ \NII ,lI-( )ll (mm (mm 4,5-(1ihydroxyuthylnnu dicthylyurua, of the formula:
In a preferred embodiment, the composition also contains resins which are conventionally used in hair setting lotions such as polyvinyl pyrrolidone/vinyl acetate or vinyl acetate/crotonic acid copolymers. The concentration of "these:
resins in the composition can be between 0.5 and 5 percent by weight.
In a particular embodiment, the cosmetic composition can also contain an acid reacting compound acting as a catalyst, in a sufficient amount to bring the pH of the composition to a value between 1.5 and 5. The acid reacting compounds can be inorganic acids such as sulfuric, hydrochloric, phosphoric acids, acid salts such as sodium and potassium monophosphates or organic acids such as acetic acid, citric acid,.lactic acid and formic acid.
The composition according to the invention can, in: addition, contain any conventional ingredient that can be used in cosmetics such as a swelling agent, surfactant, dye and perfume. g
In a preferred embodiment, the composition according'. to the invention is made in two parts, one of which contains the polycondensable compound whose formula is indicated above, while the other contains the cosmetic resin and the acid reacting compound. Thus the compositions according to the invention can be made up of a solid part containing. only the polycondensable compound, and a liquid part containing an aqueous or hydroalcoholic solution of an acid reacting compound, these two parts being intended to be mixed at the time of use.
However, it is also possible that said setting composition is in the form of a solution of the polycondensable compound not containing the acid reacting compound, the hair impregnated with said composition being rinsed before or after with an acid solution according to a process that will bedescribed below.
The present invention also has for its objecta novel process to set hair characterized by the fact that the hair is impregnated with a composition containing, in a conventional.
cosmetic vehicle or base, at least one polycondensable compound corresponding to the following formula:
l 0 R o R wherein:
X represents an oxygen atom or a sulfur atom, R and R represent either a hydrogen atom or a lower alkyl radical,
R 1 and R represent either a hydrogen atom or a lower alkyl radical, and the hair is given an acid rinse, either before or after impregnation with the composition mentioned above, the hair being rolled on setting rollers and dried with heat.
According to a variation in the process described above, the hair is impregnated with a composition containing the polycondensable compounds described above, and whose pH has been brought, at the time of use, to a value between 1.5 and 5, by the addition of a sufficient amount of acid, and the hair is rolled on setting rollers and dried by heat.
For a better understanding of the invention, there will now be described, by way of non-limiting illustration, some examples of the compositions and their use.
EXAMPLE 1 At the time of use, the solid part and liquid part of the following composition, made separately, are mixed:
acetate S 630 copolymer which is a white powder having a ratio of PVP to VA of 60:40 and having a specific gravity (25 C.) of 1.27 i 0.01 determined on the molten copolymer. Its K-value ranges between 30 and 50 wherein the K-value is a function of means molecular weight and is derived from the formula:
log nrel/C (75K."/l+l.5l(.C) K.
wherein K 1,000 K., C conc. in g/lOO m1 soln. and 1; rel viscosity of the solution compared to the solvent. Its Gardner l-laldt viscosity at 25 C. in 25 percent ethanol is 50 centipoises lactic acid q.s.p. pl-l2 water q.s.p.
EXAMPLE 2 By operating as indicated in Example 1, a setting is performed with a composition made in the two following solid and liquids parts:
solid part:
4,5-dihydroxyethylene dimethylurea 4 g. liquid part:
polyvinylpyrrolidone/vinyl acetate S 630 copolymer 2 g. HCI q.s.p. pH l.5 water q.s.p. 100 cc,
EXAMPLE 3 To set soft hair on which standard setting lotions do not give satisfactory results, the following operations are performed:
First, the hair is given a cationic shampooing intended to bring its pH to a value close to 2. Such a shampooing can have the following composition:
Then the hair is dried and impregnated with a composition containing:
dihydroxyethylene urea water q.s.p.
4 g. cc.
The hair is then put up in curlers and dried. There is obtained a setting presenting an excellent luster and satisfactory body.
EXAMPLE 4 To achieve a setting of fine and brittle hair, previously washed and dried, there is applied to the head of hair a gel having the following composition:
oleic acid H) moles QB. 27 g. paraffin oil 23 g. 4,5-dihydroxyethylene dimethylurea 0.5 g. acetic acid q.s.p. pH 3.5
water 50 cm.
R1N/ NRg (BH '1H ()R 6R wherein X is selected from the group consisting of oxygen and sulfur, R, R, R, and R each independently are selected from the group consisting of hydrogen and lower alkyl, said compound being present in amounts of 0.5 to l0 percent by weight of said composition, rinsing said hair with an aqueous acidic solution prior to or subsequent to impregnating the same with said composition, winding said hair on rollers and drying said hair.
2. The process of claim 1 wherein said compound is selected from the group consisting of 4,5-dihydroxyethylene urea, 4,5- dihydroxyethylene thiourea, 4,5 -dihydroxyethylene dimethylurea, 4,5-dimethoxyethylene urea and 4,5-dihydroxyethylene diethylurea.
3. .The process of claim 1 wherein said acidic aqueous solution consists essentially of an aqueous solution of a member selected from the group consisting of lactic acid, acetic acid, formic acid, citric acid, sulfuric acid, hydrochloric acid, phosphoric acid and sodium and potassium monophosphates, said member being present in amounts effective to polymerize said compound on said hair.
4. A process for setting hair comprising impregnating said hair with an effective amount of a composition comprising an aqueous solution of a polymerizable compound having the formula wherein X is selected from the group consisting of oxygen and sulfur, R, R, R and R each independently are selected from the group consisting of hydrogen and lower alkyl, present in amounts of 0.5 to 10 percent by weight of said composition and an acidic catalyst selected from the group consisting of lactic acid, acetic acid, formic acid, citric acid, sulfuric acid, hydrochloric acid, phosphoric acid and sodium and potassium monophosphates present in amounts sufiicient so that the pH of said composition is between 1.5 and 5, winding said hair on rollers and drying said hairv

Claims (3)

  1. 2. The process of claim 1 wherein said compound is selected from the group consisting of 4,5-dihydroxyethylene urea, 4,5-dihydroxyethylene thiourea, 4,5-dihydroxyethylene dimethylurea, 4,5-dimethoxyethylene urea and 4,5-dihydroxyethylene diethylurea.
  2. 3. The process of claim 1 wherein said acidic aqueous solution consists essentially of an aqueous solution of a member selected from the group consisting of lactic acid, acetic acid, formic acid, citric acid, sulfuric acid, hydrochloric acid, phosphoric acid and sodium and potassium monophosphates, said member being present in amounts effective to polymerize said compound on said hair.
  3. 4. A process for setting hair comprising impregnating said hair with an effective amount of a composition comprising an aqueous solution of a polymerizable compound having the formula
US881903A 1968-12-04 1969-12-03 Process for setting hair with polycondensable urea and thiourea compounds Expired - Lifetime US3661161A (en)

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4278659A (en) * 1978-12-22 1981-07-14 The Gillette Company Hair setting and bodying composition and method
US4338295A (en) * 1980-11-12 1982-07-06 The Gillette Company Hair setting and bodying composition and method
US20080066773A1 (en) * 2006-04-21 2008-03-20 Anderson Daniel G In situ polymerization for hair treatment
US20080187506A1 (en) * 2007-02-05 2008-08-07 Jose Antonio Carballada Hair care composition
US20090022681A1 (en) * 2007-02-05 2009-01-22 Jose Antonio Carballada Hair Care Composition
US20100028286A1 (en) * 2008-07-31 2010-02-04 Jose Antonio Carballada Method and Composition for Stabilizing Hair Moisture Levels
US20100028279A1 (en) * 2008-07-31 2010-02-04 Jose Antonio Carballada Method and Composition for Maintaining Hair Dye Color
US20100120871A1 (en) * 2008-11-10 2010-05-13 Dawson Jr Thomas Larry Hair care compositions, methods, and articles of commerce that can increase the appearance of thicker and fuller hair
US9358197B2 (en) 2012-06-15 2016-06-07 The Procter & Gamble Company Method employing polyols when chemically modifying the internal region of a hair shaft
US9986809B2 (en) 2013-06-28 2018-06-05 The Procter & Gamble Company Aerosol hairspray product comprising a spraying device
US10024841B2 (en) 2014-08-29 2018-07-17 The Procter & Gamble Company Device for testing the properties of fibres
US10131488B2 (en) 2015-06-01 2018-11-20 The Procter And Gamble Company Aerosol hairspray product comprising a spraying device
US11311749B2 (en) 2011-09-15 2022-04-26 The Procter And Gamble Company Aerosol hairspray for styling and/or shaping hair
US12128118B2 (en) 2021-07-29 2024-10-29 The Procter & Gamble Company Aerosol dispenser containing a hairspray composition and a nitrogen propellant

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3079297A (en) * 1960-05-31 1963-02-26 Bayer Ag Method of combating gastropods

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3079297A (en) * 1960-05-31 1963-02-26 Bayer Ag Method of combating gastropods

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4278659A (en) * 1978-12-22 1981-07-14 The Gillette Company Hair setting and bodying composition and method
US4338295A (en) * 1980-11-12 1982-07-06 The Gillette Company Hair setting and bodying composition and method
US20080066773A1 (en) * 2006-04-21 2008-03-20 Anderson Daniel G In situ polymerization for hair treatment
US20080187506A1 (en) * 2007-02-05 2008-08-07 Jose Antonio Carballada Hair care composition
US20090022681A1 (en) * 2007-02-05 2009-01-22 Jose Antonio Carballada Hair Care Composition
US20100028279A1 (en) * 2008-07-31 2010-02-04 Jose Antonio Carballada Method and Composition for Maintaining Hair Dye Color
US20100028286A1 (en) * 2008-07-31 2010-02-04 Jose Antonio Carballada Method and Composition for Stabilizing Hair Moisture Levels
US7981167B2 (en) 2008-07-31 2011-07-19 The Procter & Gamble Company Method and composition for maintaining hair dye color
US20100120871A1 (en) * 2008-11-10 2010-05-13 Dawson Jr Thomas Larry Hair care compositions, methods, and articles of commerce that can increase the appearance of thicker and fuller hair
US11311749B2 (en) 2011-09-15 2022-04-26 The Procter And Gamble Company Aerosol hairspray for styling and/or shaping hair
US9358197B2 (en) 2012-06-15 2016-06-07 The Procter & Gamble Company Method employing polyols when chemically modifying the internal region of a hair shaft
US9986809B2 (en) 2013-06-28 2018-06-05 The Procter & Gamble Company Aerosol hairspray product comprising a spraying device
US10024841B2 (en) 2014-08-29 2018-07-17 The Procter & Gamble Company Device for testing the properties of fibres
US10131488B2 (en) 2015-06-01 2018-11-20 The Procter And Gamble Company Aerosol hairspray product comprising a spraying device
US12128118B2 (en) 2021-07-29 2024-10-29 The Procter & Gamble Company Aerosol dispenser containing a hairspray composition and a nitrogen propellant

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