US3190803A - Pvp-formamidine sulfinic acid color stripping medium - Google Patents

Pvp-formamidine sulfinic acid color stripping medium Download PDF

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Publication number
US3190803A
US3190803A US212157A US21215762A US3190803A US 3190803 A US3190803 A US 3190803A US 212157 A US212157 A US 212157A US 21215762 A US21215762 A US 21215762A US 3190803 A US3190803 A US 3190803A
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Prior art keywords
stripping medium
sulfinic acid
color stripping
formamidine sulfinic
medium
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Expired - Lifetime
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US212157A
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Vogt Gunther
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Individual
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Priority to DEV20069A priority Critical patent/DE1151242B/en
Priority to FR886490A priority patent/FR1316041A/en
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Priority to US212157A priority patent/US3190803A/en
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Publication of US3190803A publication Critical patent/US3190803A/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
    • A61Q5/08Preparations for bleaching the hair
    • 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
    • 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
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • 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
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8176Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/36Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41Compounds containing sulfur bound to oxygen
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/13Fugitive dyeing or stripping dyes
    • D06P5/138Fugitive dyeing or stripping dyes fugitive dyeing
    • 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
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52Stabilizers
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00Drug, bio-affecting and body treating compositions
    • Y10S424/03Hair bleach

Definitions

  • alkaline reducing agents Alkali hyposulfates (alkali salts of dithionic acid) or sultoxylates (derivatives of sulfoxylic acid) have been used as efiective reducing agents, for instance.
  • keratin substrates such as living human hair, are unfavorably affected thereby. It is not possible to use media of a pH in excess of about 11.0 without damaging keratin fibers or hair.
  • a color stripping medium consisting of a weakly alkaline solution of a synergistic combination of about 1 to 2% of formamidine sulfinic acid (thio-urea-dioxide) and 5 to 8% of polyvinyl pyrrolidone, the percentages being by weight of the solution.
  • the pH of the medium preferably does not exceed 9.0 and the pH may be adjusted to this value by adding a buffering agent to the medium, for instance ammonium bicarbonate.
  • a buffering agent for instance ammonium bicarbonate.
  • Any suitable and commercially available buffering agent efiective in a pH range of about 7 to 9 may be used, of course, as will be evident to the skilled in the art, such as any ammonium salt of a weak acid, including ammonium acetate, ammonium citrate, ammonium lactate.
  • the color stripping medium also comprises an agent facilitating the solution of the synergistically combined reducing agents in the alkaline solvent.
  • An eiiective agent for this purpose is, for instance, a glycol mono-alkyl ether, the alkyl being a lower alkyl group, such as butyl.
  • Cellosolve, butyl Cellosolve or methyl Cellosolve may be used for this purpose.
  • the color stripping medium contains a thickening agent to impart a high viscosity to the medium.
  • This agent must be inert to the alkaline and reducing components and a useful agent of this type is, for instance, cellulose sodium glycol monoacetate. Generally, carboxymethyl cellulose, methyl cellulose and their alkali salts may be used as thickening agents.
  • the polyvinyl pyrrolidone component is a known mild bleaching agent in the textile industry but, in the color stripping medium of the invention, it exerts a stabilizing eliect on the mixture and synergistically combines with the formamidine sulfinic acid in effectuating the color stripping.
  • Example 1 1.5 parts of formamidine sulfinic acid, 5.0 parts of polyvinyl. pyrrolidone (commercially available in Germany under the trademark Luviskol K30), 5.0 parts of glycol monobutyl ether, 1.0 part of ammonium bicarbonate, 0.5 part of 25% ammonia and 2.5 parts of cellulose sodium glycol monoacetate (commercially available in Germany-under the trademark Tylose 141N600”) are thoroughly stirred into water to provide parts of the solution. The resultant product is a nearly colorless, highly viscose medium.
  • Dyed human hair is nearly completely stripped of the artificial color when this medium is applied thereto for a period of 15 to 30 minutes at normal body temperature. It the temperature is increased, the duration of the treatment is correspondingly reduced.
  • Example 2 The same medium as in Example 1 is prepared, except that the amount of formamidine sulfinic acid is reduced to one part while the polyvinyl pyrrolidone content is increased to eight parts. The results do not diflier substantially from those of Example 1.
  • a color stripping medium consisting of an aqueous alkaline solution of about 1 to 2 percent of formamidine sulfinic acid and of 5 to 8 percent of polyvinyl pyrrolidone, the percentages being by weight of the solution, and the pH of the solution not exceeding 9.
  • the color stripping medium of claim 1 further comprising 2 to 7%, by weight of the solution, of a glycol mono- (lower) -alkyl ether.
  • glycol mono-(lower)-alkyl ether is glycol monobutyl ether.
  • the color stripping medium of claim 1 further comprising a buffering agent to adjust the pH to a value not exceeding 9.
  • the color stripping medium of claim 1 further comprising a thickening agent which is inert to the other components of the solution.
  • the color stripping medium of claim 1 further comprising about 5% of glycol monobutyl ether and about 2.5% of cellulose sodium glycol monoacetate, both based on the weight of the solution.
  • a method of stripping color from living hair which comprises the step of applying thereto a stripping medium consisting of an aqueous alkaline solution of about 1 to 2 percent of formamidine suifinic acid and 5 to 8 percent of polyvinyl pyrrolidone, the percentages being by weight of the solution, and the pH of the solution not exceeding 9.

Description

' United States Patent 3,190,803 PVP-FORMIDINE SULFINIC ACID QQLGR STRIPPENG MEDIUM Giinther Vogt, Am Muhiweg, Schitrerstadt, Pfalz, Germany No Drawing. Filed July 24, 1962, Ser. No. 212,157 9 (llaims. (Cl. 167-83) The present invention relates to improvements in stripping or bleaching colored keratin substrates, particularly living hair.
It is conventional to strip or bleach dyed textile fibers by treating them with alkaline reducing agents. Alkali hyposulfates (alkali salts of dithionic acid) or sultoxylates (derivatives of sulfoxylic acid) have been used as efiective reducing agents, for instance. However, if such agents are used at their conventional high alkalinity, keratin substrates, such as living human hair, are unfavorably affected thereby. It is not possible to use media of a pH in excess of about 11.0 without damaging keratin fibers or hair.
It is accordingly the primary object of the present invention to overcome this disadvantage and to provide a color stripping medium and method for colored keratin substrates, which is highly eflicient in bleaching the substrates without damaging the same.
This and other objects are accomplished in accordance with this invention by applying to colored keratin substrates, such as living hair, a color stripping medium consisting of a weakly alkaline solution of a synergistic combination of about 1 to 2% of formamidine sulfinic acid (thio-urea-dioxide) and 5 to 8% of polyvinyl pyrrolidone, the percentages being by weight of the solution.
The pH of the medium preferably does not exceed 9.0 and the pH may be adjusted to this value by adding a buffering agent to the medium, for instance ammonium bicarbonate. Any suitable and commercially available buffering agent efiective in a pH range of about 7 to 9 may be used, of course, as will be evident to the skilled in the art, such as any ammonium salt of a weak acid, including ammonium acetate, ammonium citrate, ammonium lactate.
In a preferred embodiment, the color stripping medium also comprises an agent facilitating the solution of the synergistically combined reducing agents in the alkaline solvent. An eiiective agent for this purpose is, for instance, a glycol mono-alkyl ether, the alkyl being a lower alkyl group, such as butyl. For instance, Cellosolve, butyl Cellosolve or methyl Cellosolve may be used for this purpose.
Also, a more uniform application to the substrate will be facilitated if the color stripping medium contains a thickening agent to impart a high viscosity to the medium. This agent must be inert to the alkaline and reducing components and a useful agent of this type is, for instance, cellulose sodium glycol monoacetate. Generally, carboxymethyl cellulose, methyl cellulose and their alkali salts may be used as thickening agents.
It has been found that formamidine sulfinic acid prepared according to the process of US. Patent No. 2,150,- 921 remains stable in the medium for extended periods of time. Therefore, the color stripping medium of this invention may be bottled ready for use and stored in this condition. This is a considerable advantage over conventional bleaching media whose components are stored in separate containers and are mixed only immediately before use.
3,19,8h3 Patented June 22, 1 965 The melting point of the formamidine sulfinic acid prepared in the indicated manner lies between about 126128 C.
The polyvinyl pyrrolidone component is a known mild bleaching agent in the textile industry but, in the color stripping medium of the invention, it exerts a stabilizing eliect on the mixture and synergistically combines with the formamidine sulfinic acid in effectuating the color stripping.
While the invention is not limited thereby, it will be illustrated in connection with the following examples, wherein all parts are by weight:
Example 1 1.5 parts of formamidine sulfinic acid, 5.0 parts of polyvinyl. pyrrolidone (commercially available in Germany under the trademark Luviskol K30), 5.0 parts of glycol monobutyl ether, 1.0 part of ammonium bicarbonate, 0.5 part of 25% ammonia and 2.5 parts of cellulose sodium glycol monoacetate (commercially available in Germany-under the trademark Tylose 141N600") are thoroughly stirred into water to provide parts of the solution. The resultant product is a nearly colorless, highly viscose medium.
Dyed human hair is nearly completely stripped of the artificial color when this medium is applied thereto for a period of 15 to 30 minutes at normal body temperature. It the temperature is increased, the duration of the treatment is correspondingly reduced.
Physical and chemical examination of the stripped hair show no appreciable damage.
Example 2 The same medium as in Example 1 is prepared, except that the amount of formamidine sulfinic acid is reduced to one part while the polyvinyl pyrrolidone content is increased to eight parts. The results do not diflier substantially from those of Example 1.
Also, substantially the same results are obtained when diiferent Cellosolves are used, including methyl and ethyl Cellosolve.
What I claim is: V
1. A color stripping medium consisting of an aqueous alkaline solution of about 1 to 2 percent of formamidine sulfinic acid and of 5 to 8 percent of polyvinyl pyrrolidone, the percentages being by weight of the solution, and the pH of the solution not exceeding 9.
2. The color stripping medium of claim 1, further comprising 2 to 7%, by weight of the solution, of a glycol mono- (lower) -alkyl ether.
3. The color stripping medium of claim 2, wherein the glycol mono-(lower)-alkyl ether is glycol monobutyl ether.
4. The color stripping medium of claim 1, further comprising a buffering agent to adjust the pH to a value not exceeding 9.
5. The color stripping medium of claim 5, wherein said buitering agent is ammonium bicarbonate.
6. The color stripping medium of claim 1, further comprising a thickening agent which is inert to the other components of the solution.
7. The color stripping medium of claim 6, wherein said thickening agent is cellulose sodium glycol monoacetate.
8. The color stripping medium of claim 1, further comprising about 5% of glycol monobutyl ether and about 2.5% of cellulose sodium glycol monoacetate, both based on the weight of the solution.
9. A method of stripping color from living hair which comprises the step of applying thereto a stripping medium consisting of an aqueous alkaline solution of about 1 to 2 percent of formamidine suifinic acid and 5 to 8 percent of polyvinyl pyrrolidone, the percentages being by weight of the solution, and the pH of the solution not exceeding 9.
References Cited by the Examiner UNITED STATES PATENTS 12/51 Samel et a1 16788 X 9/59 Matlin 8-102 X OTHER REFERENCES Carbide and Carbon Chemicals Corp, Synthetic Organic Chemicals (1942), page 32.
JULIAN S. LEVITT, Primary Examiner.
F. CACCIAPAGLIA in, LEWIS GOTTS, Examiners.

Claims (1)

1. A COLOR STRIPPING MEDIUM CONSISTING OF AN AQUEOUS ALKALINE SOLUTION OF ABOUT 1 TO 2 PERCENT OF FORMAMIDINE SULFINIC ACID AND OF 5 TO 8 PERCENT OF POLYVINYL PYRROLIDONE, THE PERCENTAGES BEING BY WEIGHT OF THE SOLUTION, AND THE PH OF THE SOLUTION NOT EXCEEDING 9.
US212157A 1961-01-31 1962-07-24 Pvp-formamidine sulfinic acid color stripping medium Expired - Lifetime US3190803A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DEV20069A DE1151242B (en) 1961-01-31 1961-01-31 Removal agent for colored keratin fiber material, especially for living hair
FR886490A FR1316041A (en) 1962-01-31 1962-01-31 Bleach for colored substances made from keratin fibers, especially for healthy hair
US212157A US3190803A (en) 1962-07-24 1962-07-24 Pvp-formamidine sulfinic acid color stripping medium

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3726967A (en) * 1970-05-14 1973-04-10 Oreal Dry, free-flowing hair bleaching composition
US3997659A (en) * 1971-03-30 1976-12-14 The Procter & Gamble Company Hair bleaching compositions containing an arginine compound
US4775527A (en) * 1986-06-27 1988-10-04 Gaf Corporation Compositions used in permanent alteration of hair color
EP1166780A2 (en) * 2000-07-01 2002-01-02 Beiersdorf AG Use of physiologically acceptable sulfinic acid as antioxidant or radical scavenger in cosmetic or dermatologic preparations
US20040034944A1 (en) * 2000-08-21 2004-02-26 Frederic Legrand Bleaching composition for dyed keratinous fibers
US20140190508A1 (en) * 2011-07-29 2014-07-10 Perachem Limited Method
EP2502613A3 (en) * 2008-03-10 2015-04-01 Perachem Limited Hair treatment composition and methods
AU2013254956B2 (en) * 2008-09-16 2015-08-20 Hsnf Limited Hair treatment methods
EP2502614A3 (en) * 2008-09-16 2016-06-15 Perachem Limited Hair treatment methods
GB2565615A (en) * 2017-03-15 2019-02-20 Henkel Ag & Co Kgaa Agent for decolorizing dyed keratinous fibers
US11406578B2 (en) 2010-11-25 2022-08-09 L'oreal Process for stripping keratin fibres using a composition comprising a sulfinic acid derivative and an acidic aqueous composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3726967A (en) * 1970-05-14 1973-04-10 Oreal Dry, free-flowing hair bleaching composition
US3997659A (en) * 1971-03-30 1976-12-14 The Procter & Gamble Company Hair bleaching compositions containing an arginine compound
US4775527A (en) * 1986-06-27 1988-10-04 Gaf Corporation Compositions used in permanent alteration of hair color
EP1166780A2 (en) * 2000-07-01 2002-01-02 Beiersdorf AG Use of physiologically acceptable sulfinic acid as antioxidant or radical scavenger in cosmetic or dermatologic preparations
EP1166780A3 (en) * 2000-07-01 2002-07-24 Beiersdorf AG Use of physiologically acceptable sulfinic acid as antioxidant or radical scavenger in cosmetic or dermatologic preparations
JP2004527457A (en) * 2000-08-21 2004-09-09 ロレアル Composition for decolorizing dyed keratin fibers
US20040034944A1 (en) * 2000-08-21 2004-02-26 Frederic Legrand Bleaching composition for dyed keratinous fibers
US20050132505A9 (en) * 2000-08-21 2005-06-23 Frederic Legrand Bleaching composition for dyed keratinous fibers
EP2502613A3 (en) * 2008-03-10 2015-04-01 Perachem Limited Hair treatment composition and methods
AU2013254956B2 (en) * 2008-09-16 2015-08-20 Hsnf Limited Hair treatment methods
EP2502614A3 (en) * 2008-09-16 2016-06-15 Perachem Limited Hair treatment methods
US11406578B2 (en) 2010-11-25 2022-08-09 L'oreal Process for stripping keratin fibres using a composition comprising a sulfinic acid derivative and an acidic aqueous composition
US20140190508A1 (en) * 2011-07-29 2014-07-10 Perachem Limited Method
GB2565615A (en) * 2017-03-15 2019-02-20 Henkel Ag & Co Kgaa Agent for decolorizing dyed keratinous fibers
GB2565615B (en) * 2017-03-15 2022-05-11 Henkel Ag & Co Kgaa Agent for decolorizing dyed keratinous fibers

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