US3188275A - Vinyl acetate polyethylene glycol copolymer hair setting composition - Google Patents

Vinyl acetate polyethylene glycol copolymer hair setting composition Download PDF

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Publication number
US3188275A
US3188275A US204038A US20403862A US3188275A US 3188275 A US3188275 A US 3188275A US 204038 A US204038 A US 204038A US 20403862 A US20403862 A US 20403862A US 3188275 A US3188275 A US 3188275A
Authority
US
United States
Prior art keywords
panthenol
ether
weight
vinyl acetate
polyethylene glycol
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
US204038A
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English (en)
Inventor
Erlemann Gustav
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.)
F Hoffmann La Roche AG
Hoffmann La Roche Inc
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Application granted granted Critical
Publication of US3188275A publication Critical patent/US3188275A/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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • 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
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • 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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
    • 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

  • High molecular weight, alcohol-soluble, film-forming compounds such as polyvinyl acetate, maleic ethers, etc., form a deposit when applied to damp or hand toweldried hair. Preparations containing these compounds do not, therefore, form an unbroken film. After combing, a residue is left behind, and, as a result, hair which is treated with such products appears dull and lifeless and it proceeds to lose its resiliency.
  • a mixture comprising (1) a copolymer of vinyl acetate and polyglycols, e.g., polyethylene glycol, copolymerized in a ratio of from about 1 to about 3 parts by weight of polyglycol for each part by weight of vinyl acetate and (2) panthenol or a panthenol ether.
  • compositions of this invention are, however, slightly soluble in mixtures of water and alcohol, for example, in aqueous alcohol solutions containing from about 30% to about 70% by weight of alcohol.
  • Aqeuous alcohol solutions of this nature preferably those containing ethyl alcohol and isopropyl alcohol as the alcohol compo nent, are used in producing the compositions of this invention.
  • the quantity of copolymer which is used in preparing the compositions of this invention may vary. Generally, the copolymer will comprise from about 1% to about of the total weight of products. Similarly, varying amounts of the panthenol component can be used. Broadly, however, panthenol, or a panthenol ether, will comprise from about 0.1% to about 3.0% of the weight of the product.
  • panthenol methyl ether panthenol ethyl ether
  • These ethers are new compounds which can be obtained by the reaction of a,'y-dihydroxy-fifl-dimethylbutyrolactone with a suitable ether of 3-hydroxypropylamine.
  • compositions of this invention can addantageously contain triols, such as 1,2,3-trihydroxy- 3,7-dimethyloctane, l,2,3-trihydroxy-3,7, 1 l-trimethyldodecane, or, preferably, 1,2,3-trihydroxy-3,7,11,15-tetramethylhexadecane.
  • triols such as 1,2,3-trihydroxy- 3,7-dimethyloctane, l,2,3-trihydroxy-3,7, 1 l-trimethyldodecane, or, preferably, 1,2,3-trihydroxy-3,7,11,15-tetramethylhexadecane.
  • triols can advantageously comprise up to about 1.0% of the weight of the present compositions.
  • These triols are also new compounds.
  • dihydrolinalool (3,7-dimethyl-3-hydroxyoctaene-l)
  • isophytol with an organic peracid, for example, performic acid, and by saponifying the reaction product, thus obtained, with an alkali, for example, with sodium hydroxide.
  • Water-alcohol 40:60 to 60:40 parts by weight as needed to make Hair, which is treated with the hair treating compositions of this invention, shows not only the desired strength but also an unexpected resiliency. All other properties such as gloss, combabih'ty, durability and firmness of the witfure are outstanding.
  • the preparations can be applied either to hand towel.- dried hair or damp hair without affecting the uniform formation of the film. After drying, the resulting film is hydrophobic and the coiffure is resistant to the humidity of the atmosphere.
  • Example 1 A hair set was prepared by mixing the following-named ingredients in the proportions hereinafter indicated. All parts given are parts by weight, unless otherwise indicated.
  • Such product was found to be highly suited for use as a hair setting composition for normal hair.
  • Example 2 In this example, a hair setting composition, particularly well suited for use on slightly oily hair, was prepared.
  • composition was obtained by mixing the followingnamed ingredients in the quantities hereinafter indicated. All quantities set forth are parts by weight, unless otherwise stated.
  • Example 3 In this example, a hair setting composition was prepared which is especially suitable for use on dry hair.
  • composition was prepared by mixing the following-named ingredients in the quantities indicated. Unless otherwise stated, all parts given are parts by weight.
  • Example 4 In and of themselves, neither the panthenol ethers used in the preceding examples, nor the process by which they are produced, are part of the present invention. However, for the sake of completeness, a process for the production of the panthenol ethers used in Examples 2 and 3 hereof, as well as for the production of other ethers suitable for use in the present invention, is included herein.
  • organic solvents for example, alcohols, ketones and diethyl ether
  • the 3-methoxy-propylamine (boiling point 114- 116 C./760 mm.), used in this example, was prepared by the catalytic hydrogenation of 3-methoxy-propionitrile in methanol in the presence of ammonia.
  • panthenol phytyl ether From 3-phytyloxy-propylamine (boiling point 168- 170 C./ 0.04 mm.): panthenol phytyl ether,
  • a composition comprising (a) a copolymer of vinyl acetate and polyethylene glycol, (b) a compound selected from the'group consisting of panthenol, panthenol methyl ether, panthenol ethyl ether, panthenol allyl ether, panthenol n-decyl ether, panthenol cetyl ether, panthenol diethylaminoethyl ether, panthenol phytyl ether, panthenol geranyl ether, panthenol tetrahydrofurfuryl ether, panthenol guaicol ether and panthenol ethyl mercapto ether, and (c) a member selected from the group consisting of aqueous ethyl alcohol and aqueous isopropyl alcohol, there being present in said component (a) from about 1 to about 3 parts by weight of polyethylene glycol
  • composition of claim 1 which contains also up to about 1% by weight of a member selected from the group consisting of 1,2,3-trihydroxy-3,7-dimethyloctane, 1,2,3-trihydroxy-3,7,ll-trimethyldodecane and 1,2,3-trihydroxy-3 ,7,11 ,1S-tetramethylhexadecane.
  • composition of claim 1 wherein the ethyl ether of panthenol is employed.
  • composition of claim 1 wherein the phytyl ether of panthenol is employed.
  • a composition comprising (a) from about 2% to 5% by weight of a copolymer of vinyl acetate and polyethylene glycol, (b) from about 0.3% to about 1% by weight of a compound selected from the group consisting of panthenol, panthenol methyl ether, panthenol ethyl ether, panthenol allyl ether, panthenol n-decyl ether, panthenol cetyl ether, panthenol diethylaminoethyl ether, panthenol phytyl ether, panthenol geranyl ether, panthenol tetrahydrofurfuryl ether, panthenol guaicol ether and panthenol ethyl mercapto ether, and (c) a member selected from the group consisting of aqueous ethyl alcohol and aqueous isopropyl alcohol, and being present
  • composition of claim 6 which contains also up to about 1% by weight of a member selected from the group consisting of 1,2,3-trihydroxy-3,7-dimethyloctane, 1,2,3-tril1ydroXy-3,7,1l-trimethyldodecane and 1,2,3-trihydroxy-3,7,1 1,1S-tetramethylhexadecane.
  • composition of claim 6 which contains also from about 0.2% to about 0.5% by weight of 1,2,3-trihydroxy- 3,7,1 1,1S-tetramethylhexadecane.
  • composition of claim 8 wherein panthenol is employed is employed.
  • composition of claim 6 wherein the ethyl ether of panthenol is employed.
  • composition of claim 6 wherein the phytyl ether of panthenol is employed.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
US204038A 1961-06-26 1962-06-21 Vinyl acetate polyethylene glycol copolymer hair setting composition Expired - Lifetime US3188275A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH747061A CH408288A (de) 1961-06-26 1961-06-26 Frisierhilfsmittel und Verfahren zu dessen Herstellung

Publications (1)

Publication Number Publication Date
US3188275A true US3188275A (en) 1965-06-08

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ID=4325617

Family Applications (1)

Application Number Title Priority Date Filing Date
US204038A Expired - Lifetime US3188275A (en) 1961-06-26 1962-06-21 Vinyl acetate polyethylene glycol copolymer hair setting composition

Country Status (11)

Country Link
US (1) US3188275A (el)
BE (1) BE619352A (el)
CH (1) CH408288A (el)
DE (1) DE1467925A1 (el)
ES (1) ES278639A1 (el)
FI (1) FI42985C (el)
GB (1) GB944834A (el)
IT (1) IT943002B (el)
NL (1) NL278987A (el)
OA (1) OA00928A (el)
SE (1) SE303826B (el)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3346457A (en) * 1963-11-05 1967-10-10 Ciairol Inc Hair treating compositions containing a saturated hydrocarbon as a moisturebarrier material
DE2330957A1 (de) * 1972-06-20 1974-01-10 Oreal Kationische gepfropfte und vernetzte mischpolymerisate, verfahren zu ihrer herstellung und ihre verwendung in kosmetischen zubereitungen
US4001392A (en) * 1969-01-31 1977-01-04 Lever Brothers Company Hairdressings
WO1989001771A1 (en) * 1987-08-27 1989-03-09 S.C. Johnson & Son, Inc. Hot curling hair treatment
US4861583A (en) * 1986-09-04 1989-08-29 S. C. Johnson & Son, Inc. Hot curling hair treatment
US5833998A (en) * 1995-11-06 1998-11-10 The Procter & Gamble Company Topical compositions for regulating the oily/shiny appearance of skin
WO2002015853A1 (de) * 2000-08-21 2002-02-28 Basf Aktiengesellschaft Haarkosmetische formulierungen
CN113227341A (zh) * 2018-12-19 2021-08-06 巴斯夫欧洲公司 包含聚乙二醇接枝共聚物和芳香化学品的成型体

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8324858D0 (en) * 1983-09-16 1983-10-19 Unilever Plc Hair conditioning preparation
DE3479187D1 (en) * 1984-03-21 1989-09-07 Richardson Vicks Ltd Hair treating composition
GB2216003B (en) * 1988-02-18 1992-06-10 Toyama Chemical Co Ltd Hair restorer
DE3817623A1 (de) * 1988-05-25 1989-11-30 Bayer Ag Kosmetisches praeparat auf basis von retinolpalmitat
DE4234743A1 (de) * 1992-10-15 1994-04-21 Wella Ag Mittel zur Festigung der Haare
DE4234744A1 (de) * 1992-10-15 1994-04-21 Wella Ag Mittel zur Pflege der Haare
EP0616800A3 (en) * 1993-03-22 1995-02-15 Givaudan Roure Int Rieck fabric agent with extended diffusion.
DE19903459A1 (de) 1999-01-28 2000-08-03 Basf Ag Verfahren zur Herstellung von hochreinem Phytantriol

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH238597A (de) * 1942-09-29 1945-07-31 Hoffmann La Roche Verfahren zur Herstellung eines kosmetischen Mittels.
US2964570A (en) * 1958-02-14 1960-12-13 Rohm & Haas 1, 9-dihydroxy-2, 8-dimethyl-5-hydroxymethylnonane
US2983650A (en) * 1958-07-31 1961-05-09 Hoffmann La Roche Panthenol aerosol hair spray
US3033841A (en) * 1958-01-03 1962-05-08 Shawinigan Chem Ltd Vinyl acetate-polyoxyalkylene compound copolymers and method of preparation

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH238597A (de) * 1942-09-29 1945-07-31 Hoffmann La Roche Verfahren zur Herstellung eines kosmetischen Mittels.
US3033841A (en) * 1958-01-03 1962-05-08 Shawinigan Chem Ltd Vinyl acetate-polyoxyalkylene compound copolymers and method of preparation
US2964570A (en) * 1958-02-14 1960-12-13 Rohm & Haas 1, 9-dihydroxy-2, 8-dimethyl-5-hydroxymethylnonane
US2983650A (en) * 1958-07-31 1961-05-09 Hoffmann La Roche Panthenol aerosol hair spray

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3346457A (en) * 1963-11-05 1967-10-10 Ciairol Inc Hair treating compositions containing a saturated hydrocarbon as a moisturebarrier material
US4001392A (en) * 1969-01-31 1977-01-04 Lever Brothers Company Hairdressings
DE2330957A1 (de) * 1972-06-20 1974-01-10 Oreal Kationische gepfropfte und vernetzte mischpolymerisate, verfahren zu ihrer herstellung und ihre verwendung in kosmetischen zubereitungen
US3946749A (en) * 1972-06-20 1976-03-30 L'oreal Hair cosmetic compositions based on grafted and crosslinked copolymers
US3990459A (en) * 1972-06-20 1976-11-09 Societe Anonyme Dite: L'oreal Cationic graft and cross-linked copolymers in wavesetting lotions
US4861583A (en) * 1986-09-04 1989-08-29 S. C. Johnson & Son, Inc. Hot curling hair treatment
WO1989001771A1 (en) * 1987-08-27 1989-03-09 S.C. Johnson & Son, Inc. Hot curling hair treatment
US5833998A (en) * 1995-11-06 1998-11-10 The Procter & Gamble Company Topical compositions for regulating the oily/shiny appearance of skin
WO2002015853A1 (de) * 2000-08-21 2002-02-28 Basf Aktiengesellschaft Haarkosmetische formulierungen
US20030180245A1 (en) * 2000-08-21 2003-09-25 Michael Gotsche Hair cosmetic formulations
CN113227341A (zh) * 2018-12-19 2021-08-06 巴斯夫欧洲公司 包含聚乙二醇接枝共聚物和芳香化学品的成型体

Also Published As

Publication number Publication date
OA00928A (fr) 1968-03-22
CH408288A (de) 1966-02-28
NL278987A (el)
FI42985B (el) 1970-09-02
DE1467925A1 (de) 1969-01-16
IT943002B (it) 1973-04-02
BE619352A (el)
GB944834A (el)
ES278639A1 (es) 1963-03-01
FI42985C (fi) 1970-12-10
SE303826B (el) 1968-09-09

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