US3257361A - Hair straightening compositions and method of use - Google Patents

Hair straightening compositions and method of use Download PDF

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Publication number
US3257361A
US3257361A US216957A US21695762A US3257361A US 3257361 A US3257361 A US 3257361A US 216957 A US216957 A US 216957A US 21695762 A US21695762 A US 21695762A US 3257361 A US3257361 A US 3257361A
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US
United States
Prior art keywords
hair
mercaptoethylamine
acid
straightening
compositions
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
Application number
US216957A
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English (en)
Inventor
John J Miskel
Philip J Breivogel
Teresa M Etlinger
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.)
White Laboratories Inc
Original Assignee
White Laboratories Inc
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
Priority to BE636204D priority Critical patent/BE636204A/xx
Application filed by White Laboratories Inc filed Critical White Laboratories Inc
Priority to US216957A priority patent/US3257361A/en
Priority to GB28930/63A priority patent/GB996279A/en
Priority to DO1963001063A priority patent/DOP1963001063A/es
Priority to US329288A priority patent/US3247067A/en
Application granted granted Critical
Publication of US3257361A publication Critical patent/US3257361A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • 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
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • 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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/34—Introducing sulfur atoms or sulfur-containing groups

Definitions

  • compositions comprising a means for altering the physical :form and shape of hair (and other keratin-containing substances such as wool) and to processes [for making and using such compositions.
  • the invention sought to be patented in its composition aspect is described as residing in the concept of a salt of a mercapto lower alkyl amine with a film-forming, linear polymer of a water-soluble ethylenically unsaturated monomeric acid.
  • composition of matter comprising a salt of a mercapto lower alkyl amine with a film-forming, linear, polymer of a Water-soluble, ethylenically unsaturated monomeric acid by applying Such a composition to human hair or other keratin-containing substance, for
  • Formulations containing the tangible embodiments of our invention provide, as will lbe described later, an improved means for straightening hair without the disadately following the straightening operation.
  • film-forming, linear polymer of a water-soluble, ethylenically unsaturated monomeric acid means and includes those polymeric acids characterized as described and which are capable of forming salts with weak b ases suchas amines.
  • a polymer is specifically and preferably represented by polyacrylic acid but also includes for the purpose of illustration, but without limiting the generality of the descriptive term, other polymeric acids such polymethacrylic acid, polyu-ethylacrylic acid, polymaleic acid, sulfonated polystyrene, polyvinylsul'fu-ric acid, polyitaconic acid, and the like.
  • lower alkyl includes carbon chains having up to 3 or 4 atoms separating the mercapto group from the amino group.
  • the amino group may be primary, secondary or tertiary, and when tertiary, the amino group may be part of a cyclicamino structure such as a piperidino, pyrrolidino or morpholino.
  • mercapto lower alkyl amines contemplated by the foregoing in addition to the preferred species are N-methyl-Z-mercaptoethylamine, N- ethyl 2 mercaptoethylamine, NN-dimethyl-Z-mercaptoethylamine, NN-diethyl-2-mercaptoethylamine, N-lauryl- 2 mercaptoethylamine, N-(Z-mercaptoethyl)morpholine, N-(Z-mercarptoethyl)piperidine, N-(Z-mer-captoethyl) -pyrrolidine, the corresponding mer'capto propyl analogs represented by Z-mercaptopropylamine, B-mercaptopropylamine .and the like.
  • the tangible embodiments of our invention are safier from the aspect of hair and scalp damage since they are effectively applied at a pH of 3.06.8. It is indeed surprising thathair straightening is efiiciently induced at a pH less than 7 since the art tends 'to contraindicate such action.
  • Mercaptans such as thioglycollic acid and Z-mercaptoethylamine are known to #alter the physical form of hair but require a pH in the range of 9 to 10 wherein excessive damage and depilation occurs.
  • the straightening is made to occur at about room temperature.
  • compositions In animal tests, our compositions have been found to be free of irritation and sensitization. Indeed, no hair damage has been observed after application to living human hair over a prolonged period of time. As will be shown, our compositions require no mechanical holding device during the straightening period'nor do they require any independent neutralization step since they are automatically oxidized by air. Our compositions are indeed designed for self-application and home use. We do not claim novelty in-any particular mercapto lower alkyl amine or the use of such alone as a keratin-reducing agent. This polyacrylate.
  • the acid polymer component is not limited by molecular structure but principally by its physical properties. As a linear polymer the carboxyl (or other acid group) is repeated in each monomeric unit. Substantially each of these acid groups is neutralized by the mercapto lower alkyl amine. We prefer to employ polyacrylic acid as the polymeric component for reasons of its easy availability and utilizations; however, other equivalent polymers as described heretofore may be so utilized.
  • the salt itself may be employed as the essential active ingredient. This would entail separate preparation and purification of the salt, for example, Z-mercaptoethyl ammonium
  • the salt is generated in situ in the hair-treating formulation by admixing, for example, Z-mercaptoethylamine hydrochloride with polyacrylic acid in the presence of alkali at an appropriate pH.
  • a sodium polyacrylate may be employed as described hereinbelow.
  • the formulations are aqueous in nature and may contain a perfume or other odorant in order to make a more elegant composition.
  • compositions containing only Z-mercaptoethylammonium polyacrylate as the actice ingredient are more than satisfactory, we prefer to have an excess of polyacrylic acid present in order to maintain the pH 6.5 and to provide a more efficient film which holds the hair in a straightened position during the softening reaction.
  • Other Water-soluble or water-dispersible polymers may similarly be employed such as polyvinyl alcohol, polyvinylalcohol-polyvinyl acetate emulsions, methyl acrylate emulsions, sodium carboxymethyl cellulose, hydroxyethyl cellulose, methyl cellulose and the like.
  • humectants such as-sorbitol, glycerine and polyglycols may be added as plasticizers.
  • plasticizers such as -Also, there may be employed water-dispersible fats such as glyceryl monostearate, polyethylene glycol monostearate, stearyl dimethyl benzylammonium chloride and the like.
  • the solution is concentrated in vacuo under nitrogen. When solids, appear, concentration is halted and the mixture cooled and filtered to yield the salt of this example.
  • mercaptoalkylamine salts of polyacrylic acid are prepared in situ in the same manner as mercaptoethyl ammonium polyacrylate described above.
  • the desired product is formed in situ.
  • the corresponding di-2-mercaptoethyl ammonium polyacrylate is prepared in situ.
  • N-methyl N 2 mercaptoethylamine hydrochloride the analogous salts of this secondary amine is prepared in situ.
  • These and others are utilized in preparing formulations such as described below in the same manner as that set forth for mercaptoethyl ammonium polyacrylate.
  • Example 2 To 52.6 ml. of the solution prepared in Example 1 (13.3% mercaptoethylamine salt of polyacrylic acid) add 12.7 g. of glycerine and 2.5 g. of the monooleate. Under an atmosphere of nitrogen, stir until the mixture be- 4 comes clear and homogeneous. Dilute to g. with distilled water.
  • Formulation B Weight percent 2-mercaptoethylamine hydrochloride 10.0 Polyacrylic acid (Acrysol A3, Rohm and Hass) 70.0
  • the following formulation utilizes the salt prepared in situ from sodium polyacrylate and 2-mercaptoethylamine hydrochloride Formulation C Weight percent Mercaptoethylamine hydrochloride 7.0 Sodium polyacrylate (12.5% )Acrysol GSRohm and Haas 45.5
  • Glycerine 25.0 Isopropyl palmitate 0.5 Distilled water 22.0 pH 6.4
  • any one of the foregoing formulations or an equivalent thereof may be applied to tightly curled or kinky hair for altering its physical'form and shape such as straightening. It is preferable to cleanse the hair by shampooing, followed by a rinse and then blocking the hair in sections. The hair straightener formulation is then applied with a stiff brush to each portion of the hair. After the entire head has been covered with the hair straightening compound, it is desirable to comb the hair with a fine comb so as to stretch the hair fibres. The hair straightening action is allowed to Work for two or three hours or until the hair feels dry after which time the hair straightener is removed such as by rinsing. Hair straightened in this manner does not revert to its normal state. New growth hair will be tightly curled at the scalp portion and may be straightened as desired. In this case, however, the entire head need not be treated.
  • the foregoing formulations may be applied in a manner to produce a wave.
  • These waves in the hair may be produced by winding the hair around supports such as mandrels prior to the application of the formulation.
  • the chemical linkages in the hair are broken down and reformed while the hair is in the broadly curled position, said position resulting in soft waves.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Cosmetics (AREA)
US216957A 1962-08-15 1962-08-15 Hair straightening compositions and method of use Expired - Lifetime US3257361A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE636204D BE636204A (enrdf_load_stackoverflow) 1962-08-15
US216957A US3257361A (en) 1962-08-15 1962-08-15 Hair straightening compositions and method of use
GB28930/63A GB996279A (en) 1962-08-15 1963-07-22 Hair straightening compositions and method of use
DO1963001063A DOP1963001063A (es) 1962-08-15 1963-08-19 Composiciones que comprenden medios para alterar la forma fisica del cabello.
US329288A US3247067A (en) 1962-08-15 1963-12-09 Compositions and method for straightening hair

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US216957A US3257361A (en) 1962-08-15 1962-08-15 Hair straightening compositions and method of use

Publications (1)

Publication Number Publication Date
US3257361A true US3257361A (en) 1966-06-21

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Family Applications (1)

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US216957A Expired - Lifetime US3257361A (en) 1962-08-15 1962-08-15 Hair straightening compositions and method of use

Country Status (4)

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US (1) US3257361A (enrdf_load_stackoverflow)
BE (1) BE636204A (enrdf_load_stackoverflow)
DO (1) DOP1963001063A (enrdf_load_stackoverflow)
GB (1) GB996279A (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3484417A (en) * 1962-03-28 1969-12-16 Oreal Polysulfhdrylated polymers prepared from the reaction of maleic acid anhydride copolymers and aminothiols
US3875125A (en) * 1972-07-12 1975-04-01 Mobil Oil Corp Sorbent for heavy metals
US5985253A (en) * 1997-03-14 1999-11-16 Wella Ag Hair shaping compositions containing mercaptoethylamines and methods for the permanent shaping of hair using same
WO2009027238A1 (de) * 2007-08-28 2009-03-05 Henkel Ag & Co. Kgaa Stylingverfahren

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2925406A (en) * 1957-04-08 1960-02-16 Minnesota Mining & Mfg Polythiaalkylacrylates
US2944942A (en) * 1956-08-04 1960-07-12 Oreal Methylsilyl mercaptoacetates and their use in treating hair
US2976216A (en) * 1959-11-04 1961-03-21 Gillette Co Permanent waving agent
US3070581A (en) * 1960-02-25 1962-12-25 Lubrizol Corp Process for the preparation of organic phosphorus- and sulfur-containing compositions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2944942A (en) * 1956-08-04 1960-07-12 Oreal Methylsilyl mercaptoacetates and their use in treating hair
US2925406A (en) * 1957-04-08 1960-02-16 Minnesota Mining & Mfg Polythiaalkylacrylates
US2976216A (en) * 1959-11-04 1961-03-21 Gillette Co Permanent waving agent
US3070581A (en) * 1960-02-25 1962-12-25 Lubrizol Corp Process for the preparation of organic phosphorus- and sulfur-containing compositions

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3484417A (en) * 1962-03-28 1969-12-16 Oreal Polysulfhdrylated polymers prepared from the reaction of maleic acid anhydride copolymers and aminothiols
US3875125A (en) * 1972-07-12 1975-04-01 Mobil Oil Corp Sorbent for heavy metals
US5985253A (en) * 1997-03-14 1999-11-16 Wella Ag Hair shaping compositions containing mercaptoethylamines and methods for the permanent shaping of hair using same
WO2009027238A1 (de) * 2007-08-28 2009-03-05 Henkel Ag & Co. Kgaa Stylingverfahren

Also Published As

Publication number Publication date
BE636204A (enrdf_load_stackoverflow)
DOP1963001063A (es) 1968-08-30
GB996279A (en) 1965-06-23

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