US3171786A - Opaque aqueous polyvinyl pyrrolidone hair setting composition - Google Patents

Opaque aqueous polyvinyl pyrrolidone hair setting composition Download PDF

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US3171786A
US3171786A US302450A US30245063A US3171786A US 3171786 A US3171786 A US 3171786A US 302450 A US302450 A US 302450A US 30245063 A US30245063 A US 30245063A US 3171786 A US3171786 A US 3171786A
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polyvinyl pyrrolidone
hair
setting
amide
solution
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US302450A
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Shausky Albert
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Turner Hall Corp
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Turner Hall Corp
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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
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—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 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)
    • A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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 present invention relates to compositions for setting hair on the human head, and more particularly to an improved setting solution.
  • an altered wave shape is imparted to the hair strands so as to maintain some desired selected hair style.
  • Such alteration may be permanent as in cold permanent Waving or temporary, i.e., transient, as in setting.
  • Hair setting lotions are usually comprised of aqueous or hydro-alcoholic solutions of polymeric materials. Said polymeric materials by reason of their large molecular size form films on the hair strands after drying. In some cases the materials may penetrate the hair and form internal deposits in addition to outer films. Such films and deposits have a stiffening action which tends to hold the hair in place temporarily.
  • Polyvinyl pyrrolidone setting solutions have, conventionally, been clear. This has been so despite the fact that from an esthetic point of view it would be desirable for the setting solutions to be opaque since the public and beauty trade regard opacity as good for the hair and as an indication of softness and mildness and, conversely, believe that clear solutions dry out the hair and are bad for it.
  • a specifically selected opacifying agent is employed to produce an opaque condition in polyvinyl pyrrolidone setting solutions.
  • Said agent constitutes a primary amide produced by the reaction of ammonia and a saturated higher fatty acid the carbon chain of which has a length of from 14 to 22 carbon atoms and includes an even number of carbon atoms.
  • a primary amide is an amide with an amino group attached directly to the carbon atom of the carbonyl group. It has the structural formula:
  • reaction of ammonia and the fatty acid is generally as follows:
  • the amides employed pursuant to the instant invention are relatively insoluble in most conventional solvents including those used in polyvinyl pyrrolidone formulations. Accordingly, stock solutions of the amides in a suitable solvent are first prepared and suitable amounts of the stock solutions are incorporated in the basic polyvinyl pyrrolidone solution.
  • An excellent solvent for the amides involved herein is Igepal CO-430 sold by the Antara Division of the General Aniline and Film Corporation, 435 Hudson Street, New York, New York. This solvent is nonylphenoxypoly-(ethyleneoxy)-ethanol which is a 100% active non-ionic oil-soluble surface active agent made with four moles of ethylene oxide.
  • 10% stock solutions of the amides usable pursuant hereto are prepared with Igepal CO-430 as the solvent. These range from clear to hazy solutions in appearance. Aliquot portions of a stock solution rangingfrom 1 to 10% by weight of the basic PVP solution are added to the polyvinyl pyrrolidone formulations until the desired degree of opacity is obtained.
  • the opacifying agents disclosed herein impart opacity to the final product in the following manner.
  • the PVP solution is itself an aqueous one.
  • the amide solution is added to the basic polyvinyl pyrrolidone solution, the amide is insolubilized from the Igepal CO-430 due to the presence of an aqueous phase.
  • Example I Grams Stearamide 10 Igepal CO-430
  • Example II Behenamide 10 Igepal (IO-430 90
  • Example III Palmitamide l0 Igepal CO-430 90
  • Example IV Arachidamide l0 Igepal CO-430 90 3
  • Mytristamide Igepal CO430 90 This solution gives a turbidity of transmission with water asthe reference, using a 520m filter in Brociner-mass spectrophotometer. i i
  • Example VIII water as the reference, using a 520,1nufilterinaBroeinen- Grams Polyvinyl pyrrolidone 2:50 Urea V 1.25 Triethandlaniine 1.25 Water 88.00 10% by weight stearamide in Igepal CID-1430 7 .00.
  • An opaque alkaline composition for setting hair cold on the human head said composition essentially consistingot an aqueous carrier, urea, triethanolamine, polyvinylpyrrolidone and a stable dispersion in the carrier of from 0. 1 to, 1.0%v by weight, of an opacifying agent consisting of a primary amide which, is the reaction product of ammonia; and, a saturated higher fatty acid, .said amide being selected. from the group consistingof benhenamide, arachidamide, stearamide, palrnitamide. and. myristamide.
  • a methodv offsetting. hair on thehuman head" comprising applying cold; to the. hair, an. opaque alkaline composition essentially consisting of an aqueous carrier, urea, triethanolamine, polyvinyl pyrrolidone anda stable dispersion in the, carrier. of from. 0.1 to 1.0% by weight of. an opacifying agent consisting of a primary amide which is, the reactionproduct' of ammonia and a saturated higher 'fatty acid, said, amide. beingselected; from the group consisting of behenamide, aracliidamide, stearamide, palrnitamide, and myristamide.
  • a method of setting hair on the human. head comprising applying coldto the hair, an'opaque alkaline composition essentially consisting of an aqueous carrier, urea, triethanolamine, polyvinyl pyrrolidone, a stable dispersion in the carrier of from,0.1 to 1.0%. by weight of an opacifying agent consisting of a primary amide This. solution gives a turbidity of. 28% transmission with 7 mass spectrophotometer,

Description

United States Patent York No Drawing. Filed Aug. 15, 1963, Ser. No. 302,450 4 Claims. (43]. 167-87.1)
The present invention relates to compositions for setting hair on the human head, and more particularly to an improved setting solution.
In dressing a womans hair, customarily an altered wave shape is imparted to the hair strands so as to maintain some desired selected hair style. Such alteration may be permanent as in cold permanent Waving or temporary, i.e., transient, as in setting.
Hair setting lotions are usually comprised of aqueous or hydro-alcoholic solutions of polymeric materials. Said polymeric materials by reason of their large molecular size form films on the hair strands after drying. In some cases the materials may penetrate the hair and form internal deposits in addition to outer films. Such films and deposits have a stiffening action which tends to hold the hair in place temporarily.
Conventionally, materials of a resinous nature are employed in setting solutions, polyvinyl pyrrolidone being one of the most Widely used of such materials. A process and composition for temporarily setting hair with this substance is set forth in United States Patent No. 2,793,980.
Polyvinyl pyrrolidone setting solutions have, conventionally, been clear. This has been so despite the fact that from an esthetic point of view it would be desirable for the setting solutions to be opaque since the public and beauty trade regard opacity as good for the hair and as an indication of softness and mildness and, conversely, believe that clear solutions dry out the hair and are bad for it.
Despite the need for an opaque polyvinyl pyrrolidone setting solution, none has previously been made. One reason is that PVP is not compatible with conventional resinous oil-emulsion opacifiers such as urea formaldehyde resins, melamine formaldehyde resins, and abietic acid resins. Also, the over plasticizing (softening) action inherent in such opacifiers adversely affects the film forming properties of the polyvinyl pyrrolidone, to the detriment of the setting solution functionally.
It is a principal object of the present invention to provide an opaque PVP setting solution having setting abilities at least equal to those of conventional clear polyvinyl pyrrolidone setting solutions.
It is another object of the present invention to provide a solution of the character described having setting abilities superior to those of conventional polyvinyl pyrrolidone setting solutions.
It is another object of the present invention to provide a solution of the character described which is inexpensive and simple to manufacture.
Other objects of the invention in part will be obvious and in part will be pointed out hereinafter.
The invention accordingly consists of the compositions'of matter hereinafter described and of which the scope of application will be indicated in the appended claims.
Pursuant to the instant invention, a specifically selected opacifying agent is employed to produce an opaque condition in polyvinyl pyrrolidone setting solutions. Said agent constitutes a primary amide produced by the reaction of ammonia and a saturated higher fatty acid the carbon chain of which has a length of from 14 to 22 carbon atoms and includes an even number of carbon atoms. A primary amide is an amide with an amino group attached directly to the carbon atom of the carbonyl group. It has the structural formula:
The reaction of ammonia and the fatty acid is generally as follows:
R-OOOH NH n-(l-NHZ H2O Where R is a fatty acid chain.
The following is a list of amides usable pursuant to the instant invention:
Behenamide (docosanamide)CH (CH CONH Arachidamide (eicosanamide)CH (CH CONH Stearamide (octadecanamide)CH (CH CONH Palmitamide (heXadecanamide)CH (CH CONH Myristamide (tetradecanamide)CH (CH CONH It has been found pursuant to the present invention that 0.1% to 1.0% by weight of the amide in the PVP solution gives a range of opacity coming within the desires of the beauty trade.
The amides employed pursuant to the instant invention are relatively insoluble in most conventional solvents including those used in polyvinyl pyrrolidone formulations. Accordingly, stock solutions of the amides in a suitable solvent are first prepared and suitable amounts of the stock solutions are incorporated in the basic polyvinyl pyrrolidone solution. An excellent solvent for the amides involved herein is Igepal CO-430 sold by the Antara Division of the General Aniline and Film Corporation, 435 Hudson Street, New York, New York. This solvent is nonylphenoxypoly-(ethyleneoxy)-ethanol which is a 100% active non-ionic oil-soluble surface active agent made with four moles of ethylene oxide.
10% stock solutions of the amides usable pursuant hereto are prepared with Igepal CO-430 as the solvent. These range from clear to hazy solutions in appearance. Aliquot portions of a stock solution rangingfrom 1 to 10% by weight of the basic PVP solution are added to the polyvinyl pyrrolidone formulations until the desired degree of opacity is obtained.
'The opacifying agents disclosed herein impart opacity to the final product in the following manner. The PVP solution is itself an aqueous one. When the amide solution is added to the basic polyvinyl pyrrolidone solution, the amide is insolubilized from the Igepal CO-430 due to the presence of an aqueous phase. The amide be comes dispersed in the aqueous phase, and it is held in stable dispersion therein by the surface activity of the Igepal CO-430 in the system.
Examples of stock solutions of the amides usable pursuant to the instant invention are set forth below.
Example I Grams Stearamide 10 Igepal CO-430 Example II Behenamide 10 Igepal (IO-430 90 Example III Palmitamide l0 Igepal CO-430 90 Example IV Arachidamide l0 Igepal CO-430 90 3 Example V Mytristamide Igepal CO430 90 This solution gives a turbidity of transmission with water asthe reference, using a 520m filter in Brociner-mass spectrophotometer. i i
The above example has the maximum opacity desirable. An ex ample of a solution having the minimum opacity desirable would be as follows:
E l t Grams Polyvinyl, pyrrolidone 2.50 Urea 1.25 Triethanolamine 1.25 Water 94.00 10% by weight. stearamide in IgepaLCO -430 1 1.00 I
This solution gives aturhidity of 60% transmission with mass spectrophotometer. V. r
The optimum opacity is somewhat less than themakimum and c an bestbe determined by trial.-
example of a solution having apreferred opacity is as' follows:
Example VIII water as the reference, usinga 520,1nufilterinaBroeinen- Grams Polyvinyl pyrrolidone 2:50 Urea V 1.25 Triethandlaniine 1.25 Water 88.00 10% by weight stearamide in Igepal CID-1430 7 .00.
invention and. arewell adapted to meet the conditions of practical use..-
As variouspossible embodiments might be made of the above invention and as various changes might be made in the embodiments above set fo rth, it is to be understood that all matterl'her einabove described is to be interpreted as illustrative and not in a limiting sense.
Having thus described the invention, there is claimed as new and desiredto be secured by Letters Patent:
1. An opaque alkaline composition for setting hair cold on the human head, said composition essentially consistingot an aqueous carrier, urea, triethanolamine, polyvinylpyrrolidone and a stable dispersion in the carrier of from 0. 1 to, 1.0%v by weight, of an opacifying agent consisting of a primary amide which, is the reaction product of ammonia; and, a saturated higher fatty acid, .said amide being selected. from the group consistingof benhenamide, arachidamide, stearamide, palrnitamide. and. myristamide.
2. An opaque alkaline composition for setting. hair cold; on the human head, said, composition essentiallyconsisting of anaqueous carrier, urea, triethanolamine, polyvinyl; pyrrolidone, a stable. dispersion 'in the carrier of from 0.1 to 1.0% by weight of an. opacitlyingagent consisting ofa primary amide. whichis the reaction product of ammonia and a saturated higher fatty acid, said amide being selectedfromthe group consisting of benhenamide, arachidamide, stearamide, palmitamide. andmyristamide, and a solvent for said. opacifying. agent which solvent consists ofnonylphenoxypoly (ethyleneoxy) ethanol includingfour moles of ethylene oxide.
3. A methodv offsetting. hair on thehuman head" comprising applying cold; to the. hair, an. opaque alkaline composition essentially consisting of an aqueous carrier, urea, triethanolamine, polyvinyl pyrrolidone anda stable dispersion in the, carrier. of from. 0.1 to 1.0% by weight of. an opacifying agent consisting of a primary amide which is, the reactionproduct' of ammonia and a saturated higher 'fatty acid, said, amide. beingselected; from the group consisting of behenamide, aracliidamide, stearamide, palrnitamide, and myristamide.
4. A method of setting hair on the human. head comprising applying coldto the hair, an'opaque alkaline composition essentially consisting of an aqueous carrier, urea, triethanolamine, polyvinyl pyrrolidone, a stable dispersion in the carrier of from,0.1 to 1.0%. by weight of an opacifying agent consisting of a primary amide This. solution gives a turbidity of. 28% transmission with 7 mass spectrophotometer,
Examples VI, VII and, VIII water. as the reference, using a 520 mu filter, in a Brociner.-.
are typical and; hold true for the other primary amides listed, as: usable pursuant to the instant invention. t
The solutions embodying, the'present invention are hair or combing into thehair, They exhibiti'a. creamy which is the reaction product. of ammonia and. a saturated higher fatty acid, said, amide being selected from the group consisting of behenamide, arachidamide, stearamide, 'palmitamide and myristamide, and Y a: solvent for said opacityingagent whichJsolvent consists of nonylapplied in the conventional manner as, by spraying ohthe I or milky apperance, buttheirisetting functionshave not 2 been impaired, Indeed, it=has beenufoundpthat the famides have a hair conditioningproperty which causes solutions embodying the instant invention to be superior functionally to conventional polyvinyl pyrrolidonei's etting solutions. V g V It'thus will be seengtha t there are provided compositions of matter whichachieve the several objects of the phenoxypoly (ethyleneoxy). ethanol including four moles of ethylene oxide. 7
References Citedby the Examiner UNITED STATES PATENTS 2,418,664- 4/47 Ramsey V 16 7 87.1 2,793,980 5/57 'Mamlok et al." 1 678 .7.2
T ER E ERE E 1 Sagarin: Cosmetics;.-Science and Technology, Inter- 1 ience PubliSh6IS,.NQW, York (1957 pp. 403406.

Claims (1)

1. AN OPAQUE ALKALINE COMPOSITION FOR SETTING HAIR COLD ON THE HUMAN HEAD, SAID COMPOSITION ESSENTIALLY CONSISTING OF AN AQUEOUS CARRIER, UREA, TRIETHANOLAMINE, POLYVINYL PYRROLIDONE AND A STABLE DISPERSION IN THE CARRIER OF FROM 0.1 TO 1.0% BY WEIGHT OF AN OPACIFYING AGENT CONSISTING OF A PRIMARY AMIDE WHICH IS THE REACTION PRODUCT OF AMMONIA AND A SATURATED HIGHER FATTY ACID, SAID AMIDE BEING SELECTED FROM THE GROUP CONSISTING OF BENHENAMIDE, ARACHIDAMIDE, STEARAMIDE, PALMITAMIDE AND MYRISTAMIDE.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2528701A1 (en) * 1982-06-16 1983-12-23 Sanofi Sa ANTISEBORRHEIC COMPOSITIONS FOR COSMETIC USE COMPRISING AT LEAST ONE ALKYLPHENOL POLYOXYETHYLENE
US4767617A (en) * 1986-07-31 1988-08-30 A-Veda Corporation Opacifying composition and hair treating composition with process of using same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2418664A (en) * 1946-06-10 1947-04-08 Harry R Ramsey Hair treating cream
US2793980A (en) * 1956-01-16 1957-05-28 Dresset Corp Process and composition for setting hair on the human head

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2418664A (en) * 1946-06-10 1947-04-08 Harry R Ramsey Hair treating cream
US2793980A (en) * 1956-01-16 1957-05-28 Dresset Corp Process and composition for setting hair on the human head

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2528701A1 (en) * 1982-06-16 1983-12-23 Sanofi Sa ANTISEBORRHEIC COMPOSITIONS FOR COSMETIC USE COMPRISING AT LEAST ONE ALKYLPHENOL POLYOXYETHYLENE
EP0097567A2 (en) * 1982-06-16 1984-01-04 Sanofi S.A. Use of polyethoxylated alkyl phenols as antiseborrheic agents
EP0097567A3 (en) * 1982-06-16 1984-08-29 Sanofi, Societe Anonyme Antiseborrhoeic compositions for cosmetic use, comprising at least one polyethoxylated alkyl phenol
US4767617A (en) * 1986-07-31 1988-08-30 A-Veda Corporation Opacifying composition and hair treating composition with process of using same

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