US3676546A - Neutralizing compositions for permanent wave operation - Google Patents

Neutralizing compositions for permanent wave operation Download PDF

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Publication number
US3676546A
US3676546A US844645A US3676546DA US3676546A US 3676546 A US3676546 A US 3676546A US 844645 A US844645 A US 844645A US 3676546D A US3676546D A US 3676546DA US 3676546 A US3676546 A US 3676546A
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United States
Prior art keywords
hair
composition
neutralizing
formula
oxidizing agent
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.)
Expired - Lifetime
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US844645A
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English (en)
Inventor
Guilianna Ghilardi
Gregoire Kalopissis
Henry Philippe De Beaulieu
Jean-Louis Abegg
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LOreal SA
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LOreal SA
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Publication of US3676546A publication Critical patent/US3676546A/en
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/04Preparations for permanent waving or straightening the hair
    • AHUMAN NECESSITIES
    • A45HAND OR TRAVELLING ARTICLES
    • A45DHAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
    • A45D7/00Processes of waving, straightening or curling hair
    • A45D7/04Processes of waving, straightening or curling hair chemical
    • 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
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • 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
    • A61K2800/80Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/95Involves in-situ formation or cross-linking of polymers

Definitions

  • ABSTRACT A neutralizing composition to effect the second stage of i I neutralization of a pennanent wave operation on the hair is an [30] Foreign Appucafion Dan aqueous solution containing an N-methylol compound as an July 25, 1968 Luxembourg ..56,584 active compound in amounts of 05-12 percent by weight of July 9, 1969 Luxembourg ..59,672 the composition.
  • An oxidizing agent can also be included in the composition in amounts such that the concentration of ac- 424/71 tive compound and oxidizing agent is less than 1.7 moles/liter.
  • the oxidizing solutions used for the fixation most often contain oxygenated water, although it is possible to use other conventional oxidizing agents for this operation.
  • oxygenated water to effect the fixation phase of the permanent is accompanied by certain inconveniences in some cases.
  • oxygenated water used at full strength is able to produce significant modifications in the keratin fibers which have already been degraded by the disulphide reduction.
  • This inconvenience is particularly limiting in the case where one desires the effect of a permanent wave which is a variant of the permanent procedure. Accordingly, the hair rolled on the permanent hair rollers is dried most often under a hairdryer immediately after the fixation operation.
  • the present invention provides a neutralizing composition to carry out the second phase of the permanent operation which includes a compound having the formula I:
  • Y represents a radical -c, -c-,-c-
  • the neutralizing composition according to the invention may also include an oxidizing agent utilized in a conventional manner for carrying out of the second phase of the permanent.
  • an oxidizing agent utilized in a conventional manner for carrying out of the second phase of the permanent.
  • the quantity of such oxidiz- Iing agent may be very notably less than the quantity of the :same oxidizing agent when used in conventional neutralizing solutions which do not include an N- methvlol compound according to the invention.
  • the neutralizing lotions of the invention may effectively reduce the amount of oxygenated water employed to a concentration of about two volumes.
  • composition which can be used to effect the neutralization of a permanent or a permanent wave set, the composition being characterized by the fact that it contains at least one compound of formula I, particularly one in which Y represents the group and at least one oxidizing compound which is introduced for the purpose of reacting with the compound of formula I so as to give a substantial temperature increase to the composition.
  • oxidizing compounds which may be utilized in the composition according to the invention include, for example, oxygenated water, persalts or peroxides such as urea peroxide or the perborate of sodium or ammonium persulfate, sodium percarbonate or salts such as sodium bromate or potassium chlorate.
  • the quantity of oxidizing compounds which is added at the time the composition according to the invention is used to effect the desired temperature rise is such that the moles of the formula] compound wherein Y represents is between 0.1 and 10 times the number of oxygen molecules added to the composition. It is essential that the mount of oxidizing agent introduced into the composition according to the invention be sufficient to effect an elevation in temperature.
  • the concentration of the compound of formula I and the oxidizing compound less than 1.7 molecules per liter.
  • the quantity of heat released can be regulated by taking into account the conversion of the number of reducing molecules to the number of oxidizing molecules.
  • the pH of the fixing composition generally is between 1.5 and 6. Nevertheless, where the composition contains dimethylol ethylene thiourea, the pH may be between 8.5 and 10.
  • the fixing composition may be an aqueous solution equally containing another solvent such as butyl-glycol, diethyleneglycol, glycerine, ethyl alcohol. Particularly interesting results are obtained when a mixture containing 25 percent water and 75 percent alcohol is used.
  • compositions according to the invention are made up in two separate parts to be mixed at the moment of use, the first part containing the compounds of formula I and the second part containing the oxidizing compound.
  • the first part can be made up of the compounds of formula I in the form of powder while the second part can be made up of a hydroalcoholic solution of the oxidizing compound.
  • the compounds according to the present invention may also contain polymers for hair setting and particularly cationic polymers.
  • the present invention also provides a new procedure to effeet the second stage of a permanent operation or permanent wave set, characterized by soaking the hair after it has been set with the help of a composition such as described above.
  • the neutralizing composition is applied to the hair which has been previously set on rollers after which the hair is dried on the rollers with help of heat, for example, by means of a hairdryer.
  • This method presents important advantages over the permanent setting technique previously used. First of all, it is not necessary to rinse the neutralizing mixture before drying the hair.
  • the methylol compounds present in the mixture are capable of polymerizing with or in the keratinic fibers which as a result strengthens the fibers and augments the hold of the set.
  • the neutralizing composition is applied on the hair before it is set on the rollers, then it is dried with heat under a hairdryer.
  • This method presents the advantage of being more simple, since it is easier to impregnate the hair with the fixing lotion before the hair is rolled on the rollers.
  • Another important method contemplated by the present invention for effecting the second stage of the neutralization of the hair permanent wave operation is characterized by impregnating previously reduced hair with a mixture including at least one compound of the formula I in which Y represents to which there is added at the time of use an oxidizing compound which reacts with the compound of formula I in which Y represents to give a notable rise in temperature of the mixture with the advantages indicated above.
  • neutralization of the permanent wave set may be carried out in an equally effective manner by applying first the mixture having the compound of formula I in which Y represents and then applying immediately after a mixture having an oxidizing agent.
  • the mixture was left on the hair, free of hair covering for 15 minutes.
  • the hair was then rinsed and the following neutralizing lotion was then applied:
  • the technique of setting described in this example has the advantage over the others of being easier since the hair is not rolled on the rollers until after it has been soaked with the neutralizing solution.
  • dimethylolethylene urea 5 g silicone oil (blun) 0.3 g peptisant 0.5 g perfume 0.1 g acetic acid g.s.p. pH l.5
  • EXAMPLE 5 The hair is shampooed and then rolled on the rollers. Each roller is then saturated with a reducing composition of the following formula:
  • ammonium thioglycolate 9.5 g ammonium bicarbonate 12 g perfume 0.2 g water q.s.p. 100 cc
  • This mixture is left on the hair (under a plastic hair covering) for 15 minutes.
  • the hair is rinsed and then a neutralizing composition is applied that has been prepared at the moment of use by dissolving l g of dimethylol ethylene thiourea or a solution containing:
  • cetyl-trimethyl-ammonium bromide 0.3 g
  • the reducing solution used for the first phase of the permanent is as follows:
  • ammonium thioglycolate 9 g mono-ethanolamine q.s.p. pH 9.5 perfume 0.3 g water q.s.p. I00 cc This solution is left in contact with the hair rolled on the adequate rollers for 15 minutes. After rinsing, a neutralizing composition is applied to the rollers, this solution being prepared at the moment of use by mixing a powder containing:
  • cetyl trimethylammonium bromide 0.7 g formic acid 1 water q.s.p.
  • EXAMPLE 7 A permanent for hair dyed with the help of an oxidizing agent coloring follows the conventional treatment.
  • the reducing solution used for the first phase of the permanent has the following composition:
  • ammonium thioglycolate 5.5 g ammonium bicarbonate 5 g perfume 0.2 g water q.s.p. cc
  • the fixing solution is prepared at the moment of use, using 4 g of dimethylol ethylene thiourea in a solution containing:
  • cetyl trimethylammonium bromide 0.7 g
  • EXAMPLE 8 The same procedure as indicated in example 6 is used, a hair permanent utilizing a neutralizing composition that is prepared at the moment of use by dissolving 8 g of dimethylol ethylene thiourea in a solution containing:
  • a neutralizing composition to effect the second stage of neutralization of a permanent wave operation on the hair comprising an aqueous solution of an active compound selected from the group consisting of dimethylol ethylene urea, dimethylol ethylene thiourea, trimethylol melamine, dimethylol urea, N,N'-dimethylol (2-methyl 2- propyl) propylene bis carbamate, dimethylol methylene bis ethyl carbamate, dimethylol succinamide, dimethylol adipamide, dimethylol ethyl carbamate, tetramethylol diethylene urea, monomethylol urea, monomethylol thiourea, monomethylol dimethylhydantoin, monomethylol ethylene urea, monomethylolethylene thiourea, monomethylol dicyandiamide, monomethylol guanidine, monomethylolethyl carbamate, monomethylol die
  • oxidizing agent is selected from the group consisting of hydrogen peroxide, urea peroxide, sodium perborate, ammonium persulfate, sodium percarbonate, sodium bromate and potassium chlorate.
  • a neutralizing composition to effect the second stage of neutralization of a permanent wave operation on the hair comprising an aqueous solution of dimethylol 10 ethylene thiourea present in amounts of 05-12 percent by weight of said composition, said composition having a pH between -10.
  • the neutralizing composition of claim 3 including an oxygen-containing oxidizing agent present in amounts such that the concentration of said dimethylol ethylene thiourea and said oxidizing agent is less than 1.7 moles/liter.
  • the neutralizing composition of claim 4 wherein said oxidizing agent is selected from the group consisting of hydrogen peroxide, urea peroxide, sodium perborate, ammonium persulfate, sodium percarbonate, sodium bromate and potassium chlorate.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
US844645A 1968-07-25 1969-07-24 Neutralizing compositions for permanent wave operation Expired - Lifetime US3676546A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
LU56584 1968-07-25
LU59672 1969-07-09

Publications (1)

Publication Number Publication Date
US3676546A true US3676546A (en) 1972-07-11

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US844645A Expired - Lifetime US3676546A (en) 1968-07-25 1969-07-24 Neutralizing compositions for permanent wave operation

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US (1) US3676546A (enrdf_load_stackoverflow)
BE (1) BE736388A (enrdf_load_stackoverflow)
FR (1) FR2013680A1 (enrdf_load_stackoverflow)
GB (1) GB1279144A (enrdf_load_stackoverflow)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4109365C1 (enrdf_load_stackoverflow) * 1991-03-22 1992-01-23 Goldwell Ag, 6100 Darmstadt, De
US5132107A (en) * 1986-07-07 1992-07-21 Lange Bouke J Two-phase cleansing, conditioning and medicinal treatment shampoo
US5277206A (en) * 1991-06-10 1994-01-11 Goldwell Ag Process for permanent waving of human hair
WO2008070566A1 (en) * 2006-12-01 2008-06-12 Alberto-Culver Company Method for inhibiting fading and enhancing color intensity of color-treated hair
EP1889602A3 (de) * 2006-07-24 2009-07-08 Beiersdorf AG Kosmetische Zubereitungen zur Restrukturierung von Haaren mit besonderen Harnstoffderivaten
US20230071444A1 (en) * 2020-01-21 2023-03-09 Nutech Ventures Continuous production of keratin fibers

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2912427A1 (de) * 1979-03-29 1980-10-09 Wella Ag Mittel zur nachbehandlung von dauerverformten haaren
GB8333431D0 (en) * 1983-12-15 1984-01-25 Unilever Plc Hair treatment composition
JP4722561B2 (ja) * 2005-05-27 2011-07-13 昭和電工株式会社 ヘテロ環状メルカプト化合物を含有するパーマネントヘア加工用薬剤

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3349000A (en) * 1963-01-24 1967-10-24 Joos Bernhard Process for treating human nails and hair with dimethylol thiourea compositions

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3349000A (en) * 1963-01-24 1967-10-24 Joos Bernhard Process for treating human nails and hair with dimethylol thiourea compositions

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5132107A (en) * 1986-07-07 1992-07-21 Lange Bouke J Two-phase cleansing, conditioning and medicinal treatment shampoo
DE4109365C1 (enrdf_load_stackoverflow) * 1991-03-22 1992-01-23 Goldwell Ag, 6100 Darmstadt, De
US5401497A (en) * 1991-03-22 1995-03-28 Goldwell Ag Composition for permanent waving of human hair and use of ammonium carbamate in such compositions
US5277206A (en) * 1991-06-10 1994-01-11 Goldwell Ag Process for permanent waving of human hair
US20100068164A1 (en) * 2006-06-06 2010-03-18 Alberto-Culver Company Method for inhibiting fading and enhancing color intensity of color-treated hair
US8277790B2 (en) 2006-06-06 2012-10-02 Conopco, Inc. Method for inhibiting fading and enhancing color intensity of color-treated hair
AU2007329526B2 (en) * 2006-06-06 2012-10-04 Alberto-Culver Company Method for inhibiting fading and enhancing color intensity of color-treated hair
EP1889602A3 (de) * 2006-07-24 2009-07-08 Beiersdorf AG Kosmetische Zubereitungen zur Restrukturierung von Haaren mit besonderen Harnstoffderivaten
WO2008070566A1 (en) * 2006-12-01 2008-06-12 Alberto-Culver Company Method for inhibiting fading and enhancing color intensity of color-treated hair
US20230071444A1 (en) * 2020-01-21 2023-03-09 Nutech Ventures Continuous production of keratin fibers

Also Published As

Publication number Publication date
BE736388A (enrdf_load_stackoverflow) 1970-01-22
DE1937947B2 (de) 1977-06-08
FR2013680A1 (enrdf_load_stackoverflow) 1970-04-03
GB1279144A (en) 1972-06-28
DE1937947A1 (de) 1970-09-03

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