WO2007146909A2 - Azurant optique et stabilisant anti-uv pour des améliorations d'acrylique - Google Patents

Azurant optique et stabilisant anti-uv pour des améliorations d'acrylique Download PDF

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Publication number
WO2007146909A2
WO2007146909A2 PCT/US2007/070950 US2007070950W WO2007146909A2 WO 2007146909 A2 WO2007146909 A2 WO 2007146909A2 US 2007070950 W US2007070950 W US 2007070950W WO 2007146909 A2 WO2007146909 A2 WO 2007146909A2
Authority
WO
WIPO (PCT)
Prior art keywords
artificial nail
nail composition
monomer
composition
stabilizer
Prior art date
Application number
PCT/US2007/070950
Other languages
English (en)
Other versions
WO2007146909A3 (fr
Inventor
Susan C. Sheariss
Anthony Calise
Edward Sobolewski
Phon Malone
Original Assignee
Esschem, 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
Application filed by Esschem, Inc. filed Critical Esschem, Inc.
Publication of WO2007146909A2 publication Critical patent/WO2007146909A2/fr
Publication of WO2007146909A3 publication Critical patent/WO2007146909A3/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • 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
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/38—Percompounds, e.g. peracids
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds

Definitions

  • the invention is in the field of compositions for application to nails, which polymerize on the nail surface to yield an artificial nail structure.
  • the resulting polymerized artificial nail will have improved optical brightness and improved UV stability for making artificial nails.
  • Artificial nails are widely used by women who desire to have long, attractive fingernails which do not break or chip as readily as natural nails. Artificial nails are generally formed directly on the natural nail surface by coating on the nail a layer of a liquid monomer and polymer. The material is shaped to the desired configuration, then the material is allowed to polymerize on the nail surface to yield a hard coating. The resulting artificial nail is then shaped and polished to look like a natural nail.
  • the preparation and application of artificial nails requires a certain level of skill.
  • the monomer composition must exhibit certain properties, which enable easy application and polymerization of the composition on the nails, while at the same time providing a polymerized nail structure, which is strong, yet flexible.
  • Important properties of the polymer are catalyst levels, particle size and, flexibility.
  • S ⁇ mmary of Invention It is an object of the invention to provide an artificial nail polymer composition, which exhibits improved clarity and color brightness, and improved UV stability.
  • a liquid, artificial nail polymer composition comprised of one or more other addition-polymerizable, ethylenically unsaturated monomers, including in the composition a monoethylenically unsaturated vinyl monomer that contains two or more carbonyl groups (hereinafter referred to as a "multicarbonyl vinyl-containing monomer"), and in addition, including in the composition an optical brightener.
  • these objectives can be realized when incorporating this artificial nail polymer composition into an artificial nail structure.
  • the invention comprises a method for improving, optimizing, or enhancing the clarity and color brightness of a nail enhancement structure obtained by polymerizing on the natural nail surface a polymerizable monomer composition, during which polymerization process an effective amount of at least one multicarbonyl-vinyl containing monomer and optical brightener was added to said polymerizable monomer composition.
  • the invention also comprises a method for improving, optimizing, or enhancing the clarity and color brightness of the artificial nail composition by adding an effective amount of optical brightener to said monomer during the polymerization process.
  • nail surface means the natural nail surface, or a natural nail to which a preformed artificial nail or nail tip is adhered.
  • the polymerizable compositions of the invention may be applied directly to the keratinous surface of the natural nail, or to a nail surface having affixed thereto a pre-formed artificial nail or nail tip enhancement.
  • polymerizable means that the composition polymerizes on the nail surface upon exposure to appropriate chemicals, heat, light (such as visibile or ultraviolet light), or other types of stimuli.
  • the polymerization may occur by free radical or cationic mechanisms.
  • the invention comprises a polymerizable monomer composition for application to the nails with an optical brightener, and polymerization thereon to yield an artificial nail structure.
  • the polymerizabie composition is preferably an anhydrous liquid, having the consistency of a semi-mobile gel to freely mobile liquid at room temperature.
  • the polymerizable composition is applied to the nail surface and shaped by the nail technician. After polymerization an artificial nail structure is obtained, which is then shaped and polished.
  • the polymerizable composition of the invention contains at least one multicarbonyl-vinyl containing monomer and optical brightener.
  • the polymerization composition may also contain a UV stabilizer.
  • the composition preferably contains at least one multicarbonyl-vinyl containing monomer, preferably in the range of about 0.1-98.5%, more preferably 0.5-95%, most preferably 1-15%.
  • the multicarbonyl-vinyl containing monomer includes those having the following general formula:
  • R 3 is H, a C 1 . 30 straight or branched chain alkyl, aryl, aralkyl; and O O
  • X C i- 3 o straight or branched chain alkyl, m is 1 to 5, n is 1 to 30, y is 0 to 50; and Z-H or a C 1 . 30 straight or branched chain alkyl.
  • R 3 is hydrogen or a Cs.g alkyl, preferably methyl, and R 4 is
  • R 3 is hydrogen or methyl
  • the multicarbonyl-vinyl containing monomer is a methacrylate, such as acetoacetoxyethyl methacrylate, which has the formula:
  • Dicarboxylic acids including, but not limited to lactic, oxalic, malonic, glutaric, adipic, maleic, fumeric, tartaric, and phthalic acids are useful as UV stabilizers.
  • Preferred carboxylic acid stabilizers are alpha-hydroxy acids.
  • Preferred carboxylic acids are acetic, oxalic and lactic acids.
  • the polymerizable compositions contain oxybenzone, also known as 2-hydroxy-4- methoxybenzophenone, (2-hydroxy-4-methoxyphenyl) phenylmethanone, and benzophenone-3, CAS #: 131-57-7, which has the formula:
  • a polymerization initiator should be added which initiates or otherwise promotes the polymerization of the monomer.
  • the initiator may be a thermal initiator, photo-initiator, or a chemical initiator.
  • the Applicants do not limit their invention to any particular type of initiator.
  • Photo polymerization initiators or photo-initiators are known in the art and are described in U.S. Patent No. 4,474,868.
  • Preferred photo polymerization initiators for the purposes of this invention include UV initiators, gamma, and electron initiators.
  • Thermal initiators and chemical initiators are also known in the art.
  • Common chemical initiators include free radical initiators and ion initiators such as cationic or anionic initiators.
  • Preferred initiators for purposes of the present invention include peroxy initiators, barbituric acid, peroxide, or benzoyl acids. Most preferably, the initiator is benzyl peroxide.
  • other polymerization promoting materials such as free radical promoters and initiators, redox initiators, or metal catalysts may also be employed suitable to the chosen monomer and/or polymerizable composition.
  • optical brightener should be added to the polymerizable composition in its liquid or suspension phase prior to solidification.
  • Optical brighteners are known in the art, for example those described in U.S. Patent No. 6,890,454. The Applicants do not limit their invention to any particular type of optical brightener.
  • the optical brightener is bis(t-butyl benzoxazolyl) thiophene.
  • Other examples of optical brighteners which may be used in the present invention include 2,5-thiophenediylbis (5-tert-butyl- 1-3-benzoxazole) and 4, 4-bis(2-benzoxazoly l)sti lbenzene .
  • the polymerizable compositions may additionally contain a variety of other ingredients, such as another ethylenically unsaturated monomer, a polymerization accelerator, plasticizer, U. V. absorber, polymerization regulator, pigments and/or polymer powder.
  • Pigments include organic and inorganic pigments.
  • Other useful pigments are pearlants such as mica, bismuth oxychloride and treated micas, such as titanated micas and lecithin modified micas.
  • the organic pigments include natural colorants and synthetic monomeric and polymeric colorants. Exemplary are phthalocyanine blue and green pigment, diarylide yellow and orange pigments, and azo-type red and yellow pigments such as toluidine red, litho red, naphthol red and brown pigments. Also useful are lakes, which are pigments formed by the precipitation and absorption of organic dyes on an insoluble base, such as alumina, barium, or calcium hydrates.
  • Polymeric colorants include nylon powder, polyethylene, and polyesters. The polyesters can include linear, thermoplastic, crystalline or amorphous materials produced using one or more diols and one or more dicarboxylic acids copolymerized with colorants.
  • colorants other than the fluorescent brightener will normally constitute from about 0.1% to about 30% by weight of the composition, the amounts varying depending upon the color desired.
  • the inorganic pigments can include iron oxides (yellow, red, brown or black), ferric ammonium ferrocyanide(blue), manganese violet, ultramarine blue, chrome oxide(green), talc, lecithin modified talc, zeolite, kaolin, lecithin modified kaolin, titanium dioxide(white), and combinations thereof.
  • the polymerization composition may additionally contain a variety of antioxidants for protection against UV exposure.
  • Antioxidants are described in Kirk- Othmers (vol. 3, pg. 424) and in Uhlmanns Encyclopedia (vol. 3, pg. 91) and several types of antioxidants suitable for this purpose are described in detail in U.S. Patent No. 7,038,046. The Applicants do not limit their invention to any particular type of antioxidant.
  • the polymerizable compositions of the current invention may be used in extrusion molding processes, and may also be used in injection molding.
  • Extrusion molding techniques are well known in the art. Extrusion molding involves extruding a molten polymer through a die to create long objects of a fixed cross-section.
  • the injection molding of molten thermoplastic polymer is also well-known in the art.
  • the conventional method of injection molding is to first inject the polymer melt into the closed mold and, subsequently, to pack additional melt into the cavity to compensate for the densification of the melt during the cooling stage.
  • the polymerizab ⁇ e compositions may also be used in blow molding, compression molding, thermoforming, and rotational molding.
  • the current invention is not limited to a particular molding process.
  • the monomers described herein undergo addition polymerization generally at a temperature of about 50-125 0 C, and most preferably, at a temperature of about 70-
  • the invention is also directed to an artificial nail structure, having the physical properties disclosed in U.S. Patent No. 6,818,207.
  • the artificial nail structure contains optical brightener.
  • the artificial nail structure comprises a copolymer of an ethylenically unsaturated monomer, and a rnulticarbonyl-vinyl containing monomer having the general formula set forth above.
  • the artificial nail structure comprises a copolymer of one or more monofunctional ethylenically unsaturated monomers, one or more difunctional ethylenically unsaturated monomers, and one or more tri- or polyfunctional ethylenically unsaturated monomers and the di-carbonyl vinyl containing monomer.
  • the artificial nail structure comprises a methacrylate copolymer, such as ethyl methacrylate, methyl methacrylate s hydroxpropyl methacrylate, acetoacetoxyethyl methacrylate, tetraethylene glycol dimethacrylate, or trimethylolpropane trimethacrylate ester.
  • the artificial nail structure may also comprise a UV stabilizer.
  • the artificial nail structure of the invention may also be made in a mold, and attached to the fingernail by adhesive or other similar means.
  • the invention also comprises a method for improving, optimizing, or enhancing the clarity and color brightness of a nail enhancement structure obtained by polymerizing on the natural nail surface a polymerizable monomer composition, during which polymerization process an effective amount of at least one multicarbonyl-vinyl containing monomer is added to said polymerizable monomer composition.
  • the multicarbonyl-vinyl containing monomer is as mentioned herein, and the polymerizable monomer composition comprises at least one ethylenically unsaturated monomer, preferably acetoacetoxyethyl methacrylate.
  • An optical brightener is added during the polymerization process.
  • bis(t-butyl benzoxazolyl) thiophene is the optical brightener added.
  • the amount of optical brightener which will improve clarity and color brightness ranges from about 0.001% - 0.5%. The greater the amount of optical brightener, the greater the clarity and color brightness imparted.
  • the invention also comprises a method for improving, optimizing, or enhancing the UV stability of a nail enhancement structure obtained by polymerizing on the natural nail surface a polymerizable monomer composition, during which polymerization process an effective amount of at least one multicarbonyl-vinyl containing monomer is added to said polymerizable monomer composition.
  • the multicarbonyl- vinyl containing monomer is as mentioned herein, and the polymerizable monomer composition comprises at least one ethylenically unsaturated monomer, preferably acetoacetoxyethyl methacrylate.
  • UV stabilizer is also added during the polymerization process. In a prederred embodiment, oxybenzone is the UV stabilizer added.
  • the amount of UV stabilizer which will improve UV stability ranges from about 0.001% - 1%.
  • EXAMPLE 1 An artificial nail composition was made as follows: w.w%
  • An artificial nail composition was made as follows: w.w%
  • MMA Methyl methacrylate 30% (monomer)
  • BPO Benzyl peroxide
  • An artificial nail composition was made as follows: w.w%
  • MMA Methyl methacrylate 30% (monomer)
  • BPO Benzyl peroxide
  • An artificial nail composition was made as follows: w.w%
  • MMA Methyl methacrylate 30% (monomer)
  • BPO Benzyl peroxide
  • EXAMPLE 5 An artificial nail composition was made as follows: w.w%
  • MMA Methyl methacrylate
  • BPO Benzyl peroxide
  • An artificial nail composition was made as follows: w.w%
  • BPO Benzyl peroxide
  • EXAMPLE 7 An artificial nail composition was made as follows: w.w%
  • An artificial nail composition was made as follows: w.w% Methyl methacrylate (MMA) 100% (monomer)
  • BPO Benzyl peroxide
  • An artificial nail composition was made as follows: w.w%
  • BPO Benzyl peroxide
  • An artificial nail composition was made as follows: w.w% Ethyl methacrylate (EMA) 65% (monomer)
  • MMA Methyl methacrylate
  • BPO Benzyl peroxide
  • EXAMPLE 11 An artificial nail composition was made as follows: w,w%
  • An artificial nail composition was made as follows: w,w%
  • BPO Benzyl peroxide 1,10 % (polymerization initiator/accelerator)
  • An artificial nail composition was made as follows: w.w%
  • MMA Methyl methacrylate 30% (monomer)
  • BPO B enzy 1 peroxide
  • An artificial nail composition was made as follows: w.w%
  • MMA Methyl methacrylate 30% (monomer)
  • BPO Benzyl peroxide

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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)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne une composition pour ongles artificiels contenant un monomère contenant un multicarbonyl-vinyle, un initiateur de polymérisation, et un azurant optique. L'invention concerne en outre un procédé de préparation de la composition pour ongles.
PCT/US2007/070950 2006-06-12 2007-06-12 Azurant optique et stabilisant anti-uv pour des améliorations d'acrylique WO2007146909A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US81285806P 2006-06-12 2006-06-12
US60/812,858 2006-06-12

Publications (2)

Publication Number Publication Date
WO2007146909A2 true WO2007146909A2 (fr) 2007-12-21
WO2007146909A3 WO2007146909A3 (fr) 2008-03-06

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Application Number Title Priority Date Filing Date
PCT/US2007/070950 WO2007146909A2 (fr) 2006-06-12 2007-06-12 Azurant optique et stabilisant anti-uv pour des améliorations d'acrylique

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018170086A1 (fr) * 2017-03-16 2018-09-20 Sun Chemical Corporation Compositions de revêtement durcissables par del uv

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4104333A (en) * 1976-03-09 1978-08-01 Lee Pharmaceuticals Self-curing artificial fingernails
US6803394B2 (en) * 1999-12-17 2004-10-12 Gel Products, Inc. Radiation curable nail coatings and artificial nail tips and methods of using same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4104333A (en) * 1976-03-09 1978-08-01 Lee Pharmaceuticals Self-curing artificial fingernails
US6803394B2 (en) * 1999-12-17 2004-10-12 Gel Products, Inc. Radiation curable nail coatings and artificial nail tips and methods of using same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018170086A1 (fr) * 2017-03-16 2018-09-20 Sun Chemical Corporation Compositions de revêtement durcissables par del uv

Also Published As

Publication number Publication date
WO2007146909A3 (fr) 2008-03-06

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