US20130118520A1 - Process for semipermanent straightening of curly, frizzy or wavy hair - Google Patents

Process for semipermanent straightening of curly, frizzy or wavy hair Download PDF

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Publication number
US20130118520A1
US20130118520A1 US13/810,995 US201113810995A US2013118520A1 US 20130118520 A1 US20130118520 A1 US 20130118520A1 US 201113810995 A US201113810995 A US 201113810995A US 2013118520 A1 US2013118520 A1 US 2013118520A1
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United States
Prior art keywords
hair
water
drying
acid
reduction
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US13/810,995
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English (en)
Inventor
Alderano Mannozzi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
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 Kao Corp filed Critical Kao Corp
Assigned to ALDERAN S.A.S. DI D'OTTAVI ADELE & C. reassignment ALDERAN S.A.S. DI D'OTTAVI ADELE & C. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MANNOZZI, ALDERANO
Assigned to KAO CORPORATION reassignment KAO CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ALDERAN S.A.S. DI D'OTTAVI ADELE & C.
Publication of US20130118520A1 publication Critical patent/US20130118520A1/en
Abandoned legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A45—HAND OR TRAVELLING ARTICLES
    • A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
    • A45D7/00—Processes of waving, straightening or curling hair
    • A45D7/06—Processes of waving, straightening or curling hair combined chemical and thermal
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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

  • the present patent application for industrial invention relates to a process used to straighten curly, frizzy or wavy hair semipermanently, which is based on the combined use of glyoxylic acid and a temperature higher than 150° C.
  • the structure of human hair fiber (or hair) is well described in. US 6517822B1.
  • the techniques that are currently used to straighten curly or frizzy hair can be grouped in three families:
  • FR 1 323 640 discloses a hair straightening composition that contains vaselina and vegetal resins and also rhodinol to avoid hair breakage and ionone and coumarin to perfume.
  • FR 2 845 903 discloses a hair straightening composition that contains bisulphilketone.
  • EP 1 900 393 discloses the use of a dione, in particular diacetyl, to improve hair dying and reduce irritation caused by dyes.
  • DE 198 20 894 discloses a dye that contains tiobarbituric acid and carbonyl compounds, such as diacetyl.
  • GB 1416564 uses mercaptoderivatives to obtain permanent hair deformation based on the principle of breakage of cystine disulphide bridges using also glyoxilyc acid salts (not glyoxylic acid) in the mixture with evident purpose of pH buffering agents.
  • the declared concentrations of glyoxylic acid salts are all lower than 4% by weight and moreover the process disclosed in GB 1416564 excludes the use of temperatures higher than 150° C. Such low glyoxylic acid concentrations and such temperatures are not effective for hair straightening.
  • U.S. Pat. No. 6,086,861 uses glyoxylic acid and its salts to treat hair dandruff.
  • WO 2007/135299 and FR 2901472 disclose a method to treat keratine fibers using high temperature and special families of carboxylic acids (alpha-hydroxylic and alpha-ketone acids) and derivatives, and in particular pyruvic acid. Moreover, the concentration ranges of pyruvic acids (2-8 Molar) are excessively high, making the acid ineffective in the following hair washings.
  • the purpose of the present invention is to eliminate the drawbacks of the prior art, by disclosing a hair straightening process that is efficient, effective and time-lasting for at least six washings.
  • Another purpose of the present invention is to provide such a hair straightening process that is not harmful for hair and for the health of the person applying it.
  • the object of the invention is a process based on the combined use of glyoxylic acid and a high-temperature mechanical treatment.
  • Said mechanical treatment provides for mechanical straightening with iron at a temperature of about 200° C. (+/ ⁇ 30° C.).
  • the process comprises the following steps:
  • the process of the invention allows for obtaining straight, soft, glossy hair (with strong volume reduction in case of frizzy hair) from curly and/or frizzy hair, maintaining such properties also after repeated washings with water and shampoo (semipermanent effect).
  • the process of the invention modifies the spatial conformation of hair, reducing volume and number of curves.
  • Glyoxylic acid is dissolved in water to obtain an aqueous solution of glyoxylic acid.
  • glyoxylic acid is dissolved in water with concentration comprised between 4.5 and 14.5% by weight. Said range has given the best results in terms of efficiency to obtain straight hair.
  • the aqueous solution of glyoxylic acid can be added with a mixture of Diacetyl and Acetoin.
  • the addition of said mixture has given remarkable effects in terms of hair straightening.
  • the mixture of Diacetyl and Acetoin is dissolved in said aqueous solution of glyoxylic acid in concentration comprised between 1 and 5% by weight.
  • the aqueous solution of glyoxylic acid can be dissolved in a cosmetic hair composition containing one or more ingredients that are commonly used in cosmetics.
  • said cosmetic ingredients can be the ones describes in the Decision of the European Commission dated 8 May 1996 published on the Official Journal of the European Community (DUCE L 132 dated 01/06/1996).
  • the process of the invention allows for changing the conformation of hair so that it acquires a straight shape, if originally curly and frizzy, and maintains it for at least six hair washings.
  • said process has proved to induce semipermanent modifications in hair conformation, which remain such also after repeated hair washings in common use conditions.
  • composition examples of aqueous solutions of glyoxylic acid used for the tests Following are composition examples of aqueous solutions of glyoxylic acid used for the tests,
  • hair was straightened with hair-straightening iron heated at average temperature of approximately 210° C.
  • the solution described in example 3 of WO 2007/135299 was prepared, consisting in a solution of pyruvic acid 4 Molar (35.2% by weight) in water. Said solution was used according to the instructions contained in WO 2007/135299, that is hair temperature of 40° C., 25 minute contact time and iron temperature of 180°.
  • Tables 1 to 4 show the results obtained with the composition of the invention for 60 minute contact time.
  • table 5 shows the results obtained with the composition of the invention for 30 and 120 minute contact time.
  • the efficacy of the treatment of the invention in the modification of the shape of hair, has proved to be stable over time for at least six washings, rinsings and dryings in common use conditions of hair shampoo.
  • the method of the invention has given the best results with the solution of glyoxylic acid described in example 2 for 60 minute contact time on hair.
  • the ponderal ratio between Diacetyl and Acetoin can change according to the purity of substances.
  • 1:10, 1:1 and 10:1 diacetyl/acetoin ponderal ratios were considered in examples 4, 5 and 6.
  • Glyoxilyc Acid (CAS number: 563-96-2 or, in aqueous solution, CAS number: 298-12-4). Its use in the cosmetic sector as buffering substance is considered to be safe and is permitted without restrictions.
  • Diacetyl (CAS number 431-03-8). It is an organic substance produced by lactic bacteria in presence of carbohydrates and oxigen (see EPO430406). In the production of Diacetyl by means of bacterial fermentation also Acetoin is produced by the same bacteria. Diacetyl is normally used as aroma in the food industry.
  • Acetoin (CAS number 513-86-0). It is an organic substance produced by lactic bacteria in presence of carbohydrates and oxigen (see EPO430406). In the production by means of bacterial fermentation of Acetoin, Diacetyl is produced by the same bacteria. Acetoin is normally used as aroma in the food industry.
  • Buffering agent when dissolved in water, it reduces the pH variation of the solution to the addition of acid or alkalinesubstances.
  • Semipermanent treatment treatment in acid environment (pH lower than 7) of curly or frizzy hair to straighten it, with permanence in such a condition for at least six washings with water and shampoo, without using substances able to react with cystine disulphide bridges or by means of alkali
  • Permanent treatment hair treatment to bring it to curly or straight condition with permanence in such a condition for at least six washings by means of oxido-reduction process of disulphide bridges of the cystine contained in hair or by means of hydrolysis of peptidic bonds with alkali (pH higher than 7).
  • the technique is well known and described in WO 2007/135299 A1 and U.S. Pat. No. 4,409,204.
  • Hair-straightening iron Electrical heating device that is used by associating heat and pressure to straighten hair. It is generally composed of two flat heating elements, covered with various materials, between which a lock of hair is pressed at a time. Said hair-straightening irons are commonly found on the market.
  • Hair dryer ordinary hair-drying device with heating resistance and fan.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US13/810,995 2010-07-20 2011-05-24 Process for semipermanent straightening of curly, frizzy or wavy hair Abandoned US20130118520A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
ITMC2010A000079 2010-07-20
ITMC2010A000079A IT1401087B1 (it) 2010-07-20 2010-07-20 Uso di alfa cheto acidi, o loro derivati, per rendere liscio il capello riccio, crespo od ondulato.
PCT/EP2011/058509 WO2012010351A2 (en) 2010-07-20 2011-05-24 Process for semipermanent straightening of curly, frizzy or wavy hair.

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/058509 A-371-Of-International WO2012010351A2 (en) 2010-07-20 2011-05-24 Process for semipermanent straightening of curly, frizzy or wavy hair.

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US14/947,394 Continuation US10952516B2 (en) 2010-07-20 2015-11-20 Process for semipermanent straightening of curly, frizzy or wavy hair

Publications (1)

Publication Number Publication Date
US20130118520A1 true US20130118520A1 (en) 2013-05-16

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Family Applications (2)

Application Number Title Priority Date Filing Date
US13/810,995 Abandoned US20130118520A1 (en) 2010-07-20 2011-05-24 Process for semipermanent straightening of curly, frizzy or wavy hair
US14/947,394 Active US10952516B2 (en) 2010-07-20 2015-11-20 Process for semipermanent straightening of curly, frizzy or wavy hair

Family Applications After (1)

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US14/947,394 Active US10952516B2 (en) 2010-07-20 2015-11-20 Process for semipermanent straightening of curly, frizzy or wavy hair

Country Status (11)

Country Link
US (2) US20130118520A1 (ru)
EP (1) EP2595705B1 (ru)
JP (1) JP5919267B2 (ru)
CN (1) CN103002765B (ru)
AU (1) AU2011281867B8 (ru)
BR (1) BR112013001235A2 (ru)
HK (1) HK1177585A1 (ru)
IT (1) IT1401087B1 (ru)
RU (1) RU2563233C2 (ru)
SG (2) SG187147A1 (ru)
WO (1) WO2012010351A2 (ru)

Cited By (16)

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PT107337A (pt) * 2013-12-03 2014-04-29 Alessandra Ferreira Santos Ponces Método para alisamento do cabelo
EP2883535A1 (en) 2013-12-13 2015-06-17 Alfa Parf Group S.p.a. Compositions and methods for simultaneous reshaping and direct coloring of hair
WO2017041903A1 (en) * 2015-09-08 2017-03-16 Kao Germany Gmbh Process for semipermanent straightening and permanent shaping hair
US9844500B2 (en) 2010-02-24 2017-12-19 Kao Corporation Process for semi-permanent straightening of curly, frizzy or wavy hair
US10434051B2 (en) 2014-12-19 2019-10-08 The Procter And Gamble Company Shaping keratin fibers using arabinose and ethylene carbonate
US10568826B2 (en) 2014-12-19 2020-02-25 The Procter And Gamble Company Shaping keratin fibres using a pretreatment and a protein crosslinking composition
US10729630B2 (en) 2013-12-19 2020-08-04 The Procter & Gamble Company Shaping keratin fibres using an active agent comprising at least two functional groups selected from: —C(OH)- and —C(=O)OH
US10912726B2 (en) 2013-12-19 2021-02-09 The Procter And Gamble Company Shaping keratin fibres using a reducing composition and a fixing composition
US10945931B2 (en) 2015-06-18 2021-03-16 The Procter And Gamble Company Shaping keratin fibres using dialdehyde compounds
US11096879B2 (en) 2013-12-19 2021-08-24 The Procter And Gamble Plaza Shaping keratin fibres using an active agent comprising a functional group selected from the group consisting of: -C(=O)-, -C(=O)-H, and -C(=O)-O-
US11103434B2 (en) 2013-12-19 2021-08-31 The Procter And Gamble Company Shaping keratin fibres using carbonate ester
US11110046B2 (en) 2013-12-19 2021-09-07 The Procter And Gamble Company Shaping keratin fibres using 2-hydroxypropane-1,2,3-tricarboxylic acid and/or 1,2,3,4-butanetetracarboxylic acid
US11129784B2 (en) 2013-12-19 2021-09-28 The Procter And Gamble Company Shaping keratin fibres using oxoethanoic acid and/or derivatives thereof
US11129781B2 (en) 2014-12-05 2021-09-28 Kao Corporation Agent for hair deforming treatment
US11154480B2 (en) 2013-12-19 2021-10-26 The Procter And Gamble Company Shaping keratin fibres using a sugar
US11324685B2 (en) 2016-06-07 2022-05-10 Kao Germany Gmbh Process for treating hair

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JP5777083B2 (ja) * 2010-05-28 2015-09-09 株式会社ミルボン 毛髪変形処理方法
ITAP20120007A1 (it) 2012-07-25 2014-01-26 D Ottavi Adele Modifica semipermanente della struttura delle fibre cheratinose dei capelli mediante l'uso combinato di calore e di miscele di sostanze organiche
AU2013339733B2 (en) * 2012-11-05 2016-09-15 Kao Corporation Process for straightening and dyeing hair
DE202013011965U1 (de) 2012-11-05 2015-01-15 Kao Corporation Zusammensetzungen zum Glätten und Bleichen von Haar
DE202013011967U1 (de) 2012-11-05 2015-02-09 Kao Corporation Zusammensetzungen zum Färben und Glätten von Haaren
FR2997849B1 (fr) * 2012-11-09 2015-01-16 Oreal Composition comprenant un derive dicarbonyle et procede de lissage des cheveux a partir de cette composition
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FR2997848B1 (fr) * 2012-11-09 2015-01-16 Oreal Composition comprenant un derive dicarbonyle et procede de lissage des cheveux a partir de cette composition
FR2997845B1 (fr) * 2012-11-09 2015-03-06 Oreal Procede de lissage des cheveux a partir d'une composition contenant de l'acide glyoxylique et/ou un de ses derives
FR2997846B1 (fr) * 2012-11-09 2023-10-20 Oreal Composition comprenant un derive dicarbonyle et un acide, le procede de lissage des fibres keratiniques a partir de cette composition
FR2997851B1 (fr) * 2012-11-09 2014-11-28 Oreal Composition comprenant un derive dicarbonyle et procede de lissage des cheveux a partir de cette composition
FR2997844B1 (fr) * 2012-11-09 2014-12-05 Oreal Composition comprenant un compose dicarbonyle et procede de lissage des cheveux a partir de cette composition
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BR112015020478B1 (pt) * 2013-02-28 2021-05-25 Kao Corporation processo para alisamento semipermanente do cabelo
US10383805B2 (en) 2013-02-28 2019-08-20 Kao Corporation Composition and process for semi-permanent straightening of hair
SG11201509247SA (en) * 2013-05-10 2015-12-30 Kao Corp Process for one-step colouring and straightening hair
US10449132B2 (en) 2013-09-16 2019-10-22 Kao Corporation Process for treating hair
WO2015036052A1 (en) 2013-09-16 2015-03-19 Kao Corporation Process for semi-permanent hair straightening and aftercare of the hair
EP3046631B1 (en) * 2013-09-16 2017-06-07 Kao Corporation Hair treatment process
DE102013225915A1 (de) * 2013-12-13 2015-06-18 Henkel Ag & Co. Kgaa Haarglättung mit Glyoxylsäure
JP5947340B2 (ja) * 2014-07-11 2016-07-06 株式会社 資生堂 毛髪処理剤
JP6293718B2 (ja) * 2014-12-05 2018-03-14 花王株式会社 毛髪変形処理剤
JP6316790B2 (ja) * 2014-12-05 2018-04-25 花王株式会社 毛髪変形処理剤
JP2016108322A (ja) * 2014-12-05 2016-06-20 花王株式会社 毛髪変形処理剤
EA033701B1 (ru) * 2015-07-21 2019-11-18 Unilever Nv Композиция для придания формы волосам
EP3346975B1 (en) 2015-09-08 2020-05-20 Kao Germany GmbH Process for semipermanent straightening and dyeing hair
EP3225229A1 (en) 2016-03-29 2017-10-04 Kao Germany GmbH Process for treating hair
JP2019026574A (ja) * 2017-07-27 2019-02-21 株式会社 資生堂 毛髪強化剤
JPWO2019155968A1 (ja) * 2018-02-09 2021-01-28 株式会社 資生堂 毛髪処理組成物
JP2019142798A (ja) * 2018-02-20 2019-08-29 アドバンス株式会社 毛髪処理剤および毛髪処理方法
DE202018006763U1 (de) 2018-11-29 2022-08-18 Kao Germany Gmbh Zusammensetzung zum Glätten von Keratinfasern
EP3659577A1 (en) 2018-11-29 2020-06-03 Kao Germany GmbH Keratin fiber straightening composition, process, and kit-of-parts
CN114340593A (zh) 2019-08-29 2022-04-12 花王株式会社 用于角蛋白纤维半永久拉直和卷曲的组合物、方法和套件
RU2730486C1 (ru) * 2019-10-09 2020-08-24 Общество с ограниченной ответственностью "ЮНИКОСМЕТИК" Косметические процедуры, связанные с нагревом кератиновых волокон
EP3973945A1 (en) 2020-09-25 2022-03-30 Kao Germany GmbH Composition, process and kit for semi-permanent straightening keratin fibers
EP3973944A1 (en) 2020-09-25 2022-03-30 Kao Germany GmbH Composition, process and kit for semi-permanent straightening keratin fibers
WO2022218535A1 (en) 2021-04-15 2022-10-20 Ramade Lorente Natalia Hair-straightening-filler complex and compositions thereof

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PT107337A (pt) * 2013-12-03 2014-04-29 Alessandra Ferreira Santos Ponces Método para alisamento do cabelo
EP2883535A1 (en) 2013-12-13 2015-06-17 Alfa Parf Group S.p.a. Compositions and methods for simultaneous reshaping and direct coloring of hair
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US11096879B2 (en) 2013-12-19 2021-08-24 The Procter And Gamble Plaza Shaping keratin fibres using an active agent comprising a functional group selected from the group consisting of: -C(=O)-, -C(=O)-H, and -C(=O)-O-
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US10568826B2 (en) 2014-12-19 2020-02-25 The Procter And Gamble Company Shaping keratin fibres using a pretreatment and a protein crosslinking composition
US10434051B2 (en) 2014-12-19 2019-10-08 The Procter And Gamble Company Shaping keratin fibers using arabinose and ethylene carbonate
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RU2013107409A (ru) 2014-08-27
US10952516B2 (en) 2021-03-23
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US20160073756A1 (en) 2016-03-17
WO2012010351A3 (en) 2012-06-28
IT1401087B1 (it) 2013-07-12
JP2013531046A (ja) 2013-08-01
AU2011281867B2 (en) 2014-09-18
AU2011281867B8 (en) 2014-10-16
RU2563233C2 (ru) 2015-09-20
JP5919267B2 (ja) 2016-05-18
HK1177585A1 (zh) 2013-08-23

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