WO2007060710A1 - Preparation pour manucure et procede pour produire celle-ci - Google Patents

Preparation pour manucure et procede pour produire celle-ci Download PDF

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Publication number
WO2007060710A1
WO2007060710A1 PCT/JP2005/021430 JP2005021430W WO2007060710A1 WO 2007060710 A1 WO2007060710 A1 WO 2007060710A1 JP 2005021430 W JP2005021430 W JP 2005021430W WO 2007060710 A1 WO2007060710 A1 WO 2007060710A1
Authority
WO
WIPO (PCT)
Prior art keywords
monomer
radical polymerizable
polymerizable functional
functional group
group
Prior art date
Application number
PCT/JP2005/021430
Other languages
English (en)
Japanese (ja)
Inventor
Kazunori Kobayashi
Toru Matsunaga
Kenji Uno
Original Assignee
Seed Co., Ltd.
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 Seed Co., Ltd. filed Critical Seed Co., Ltd.
Priority to PCT/JP2005/021430 priority Critical patent/WO2007060710A1/fr
Publication of WO2007060710A1 publication Critical patent/WO2007060710A1/fr

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00Manicure or pedicure preparations
    • 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
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89Polysiloxanes
    • A61K8/896Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00Manicure or pedicure preparations
    • A61Q3/02Nail coatings
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/02Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing phosphorus
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon

Definitions

  • the present invention relates to a nail material and a method for producing the same. More specifically, the present invention relates to a nail polish excellent in film-forming property, transparency and oxygen permeability and having a very small amount of residual monomer, and a method for producing the same.
  • the nail is hard keratin similar to the stratum corneum of the skin, and is composed of thin keratinocytes in close contact.
  • the nail floor is part of the nail plate that is incompletely formed and not sufficiently keratinized, and oxygen permeability is required.
  • Various improvements with little permeability are being considered.
  • Patent Documents 1 to 3 For example, a beautiful nail material having oxygen permeability (see Patent Documents 1 to 3), a beautiful nail material using a silicone-based rosin (see Patent Documents 4 to 5), and a silicone system obtained by emulsion polymerization Water-based nail polish using polymer emulsion (see Patent Document 6), and nail material obtained by solution polymerization of a silicone monomer mixture (see Patent Document 7) have been proposed.
  • Patent Document 1 Japanese Patent Laid-Open No. 5-139931
  • Patent Document 2 Japanese Patent Laid-Open No. 5-255043
  • Patent Document 3 Japanese Patent Laid-Open No. 7-61908
  • Patent Document 4 Japanese Patent Laid-Open No. 59-199621
  • Patent Document 5 JP-A-6-157246
  • Patent Document 6 JP-A-8-92038
  • Patent Document 7 Japanese Patent Laid-Open No. 2003-342128
  • the water-based emulsion nail polish disclosed in Patent Document 6 requires a longer drying time after application than an organic solvent-type nail polish, which is inferior in convenience and further, since it is an emulsion, its transparency is lowered. The appearance after application may be impaired.
  • Patent Document 7 a beautiful nail material excellent in film forming property, transparency and oxygen permeability at the time of application to the nail is obtained, and after the synthesis, it is directly applied to the nail without requiring any post-treatment. As a result, the production process is simplified and the productivity is excellent.
  • the unpolymerized monomer remaining in the nail polish has not been examined, and there is a concern about the effect on the nails and skin.
  • the object of the present invention is excellent in transparency, oxygen permeability and film-forming property, and it is possible to directly use a copolymer at the time of synthesizing a resin.
  • An object of the present invention is to provide a beauty nail material in which polymerization monomers are reduced as much as possible and a method for producing the same.
  • the present invention is a silicone monomer having one radical polymerizable functional group, a monomer having a carboxyl group or a phosphate group and a radical polymerizable functional group in the molecule, and copolymerizable therewith.
  • an oxygen-permeable beauty nail material comprising a copolymer having a monomer power having a radical polymerizable functional group, wherein the residual monomer in the copolymer is 0.5% or less.
  • the present invention also relates to a silicone-based monomer having one radical polymerizable functional group, a monomer having a carboxyl group or a phosphate group and a radical polymerizable functional group in the molecule, and copolymerizable therewith.
  • a polymerization initiator is added to the monomer mixture having a radical polymerizable functional group.
  • Oxygen-permeable nail material having a residual monomer content of 0.5% or less, obtained by solution polymerization performed by adding 3 parts by weight or more to 100 parts by weight of the monomer component I will provide a.
  • the present invention relates to a silicone monomer having one radical polymerizable functional group, a monomer having a carboxyl group or a phosphate group and a radical polymerizable functional group in the molecule, and copolymerizable therewith.
  • a solution polymerization is carried out by adding a polymerization initiator in a mixture of monomer components having radically polymerizable functional groups in a total amount of 3 parts by weight or more in 100 parts by weight of monomer components at least twice or more.
  • the present invention provides a method for producing an oxygen-permeable beauty nail material having a residual monomer content of 0.5% or less in the copolymer.
  • the film has good film-forming properties, transparency and oxygen permeability, and the residual monomer in the copolymer component can be reduced as much as possible, thereby reducing the deterioration of the nails and the feeling of pressure. Higher safety! Amami nails can be provided.
  • the film-forming property that affects the adhesion of the silicone-based nail material is related to the surface free energy of the beauty nail material, and the better the nail material is wet, the better the adhesion.
  • low-polarity polymers such as silicone-based greaves have poor adhesion to the nail surface, that is, film formation, which has low surface free energy. For this reason, film formation can be effectively improved by introducing a polar group, especially a carboxyl group or a phosphate group having a strong polarity into the nail polish.
  • a monomer having a radical polymerizable monomer having a carboxyl group or a phosphate group in the molecule is used in order to improve the film forming property.
  • Specific examples include (meth) acrylic acid, (meth) atariloy oral kichetyl succinic acid, (meth) atariloy oral kichetylphthalic acid, (meth) atariloy oral kichetyl hexahydrophthalic acid, 2-methacryloylloxichelic acid phosphate.
  • at least one or more are selected and used.
  • methacrylic acid methacryloyl oxychetyl succinic acid
  • 2-metathalyl leuloch cetyl acid phosphate are preferably used.
  • the amount used is preferably 3 to 50% by weight, more preferably 5 to 35% by weight in the copolymer component. Less than 3% by weight If the amount exceeds 50% by weight, the oxygen permeability tends to be lowered.
  • a silicone monomer having one radical polymerizable functional group is used in order to impart oxygen permeability.
  • Specific examples include pentamethyldisiloxanylmethyl (meth) atalylate, pentamethyldisiloxalpropyl (meth) atalylate, tris (trimethy
  • the amount of these silicone monomers used is preferably 10 to 80% by weight in the copolymer component, More preferably, it is 20 to 70% by weight, and if it is less than 10% by weight, the oxygen permeability tends to be lowered, and if it is more than 80% by weight, the film forming property tends to be lowered.
  • the amount of these monomers used is preferably 20 to 90% by weight, more preferably 20 to 70% by weight in the copolymer component. If it is less than 20% by weight, it is difficult to obtain sufficient hardness and film forming property, and if it is more than 90% by weight, oxygen permeability tends to be lowered.
  • the amount of the polymerization initiator in this field has not been particularly taken into consideration, and is generally based on 100 parts by weight of the monomer component. Used in the range of 0.5 to 1 part by weight.
  • the amount of the polymerization initiator is 3 parts by weight or more, preferably 3 to 12 parts by weight, more preferably 5 to 10 parts by weight, particularly 100 parts by weight of the monomer component.
  • solution polymerization is performed within the range of 6 to 9 parts by weight.
  • the total amount of the polymerization initiator may be added at the time of preparation of each monomer, but it is divided as the polymerization reaction proceeds, for example, at the time of preparation of each monomer and at a certain time after the start of the reaction. It is effective when added.
  • the timing of addition of the polymerization initiator and the number of divisions vary depending on the polymerization temperature, the half-life of the initiator used, etc., but are usually added at regular intervals from the preparation of each monomer and after the start of the reaction. It is preferable.
  • the number of additions per fixed time can be any number of times depending on the conditions of the polymerization reaction, preferably about 1 to 4 times, and the desired effect can be obtained by this division.
  • radical polymerization initiator examples include 2, 2'-azobisisobutyoxy-tolyl, 1, 1'-azobis (cyclohexane mono 1-carbo-tolyl), 2, 2'-azobis (2 -Methylbutyrate-tolyl), 2,2'-azobis (2,4 dimethylvale-tolyl), 2,2'-azobis (4-methoxy-2,4 dimethylvale-tolyl), 2, 2,- Azo compounds such as dimethyl azobisisobutyrate, 2,2'-azobis (2, 4, 4 trimethylpentane), benzoyl peroxide, lauroyl peroxide, stearoyl peroxide, bis (4 tertiary butyl cyclohexyl) Peroxydicarbonate, ⁇ - ⁇ 'bis (tertiarybutylperoxy) diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5bis (tertiarybutyl
  • 2,2,1-azobisisobutyrate-tolyl, tertiary butyl peroxybivalate, and tertiary monobutyl peroxyneodecanoate which can carry out the polymerization reaction relatively moderately, are preferably used.
  • Solution polymerization in the present invention is carried out according to a conventional method, in which a monomer is dissolved in a solvent, a polymerization initiator is added, and the temperature is 40 to 80 ° C in a nitrogen atmosphere for about 6 to 25 hours. It is preferable to heat and stir. Furthermore, before the polymerization reaction is completed, the reaction temperature is raised by about 10 to 40 ° C within a range where the maximum temperature does not exceed 120 ° C, and in that state for a while, for example, about 1 to 10 hours. This is preferable because it can effectively reduce the amount of residual monomer.
  • Solvents used include alcohols such as methanol, ethanol, propanol, and butanol, ketones such as acetone, methyl ethyl ketone, and jetyl ketone, esters such as ethyl acetate and butylacetate, and aromatics such as benzene, toluene, and xylene.
  • alcohols such as methanol, ethanol, propanol, and butanol
  • ketones such as acetone, methyl ethyl ketone, and jetyl ketone
  • esters such as ethyl acetate and butylacetate
  • aromatics such as benzene, toluene, and xylene.
  • family solvents silicone solvents used in cosmetics, light liquid paraffin, and the like.
  • the amount and type of these organic solvents affect the effect at the time of use after synthesizing the nail polish. That is, when the amount used is small, the viscosity of the nail polish is high and the applicability to the nail is inferior, and the resin does not pull the thread at the time of application, and the surface after application does not become smooth. When the amount is too large, it is difficult to obtain a film having a sufficient thickness. Therefore, the amount of the organic solvent used is preferably such that the concentration of rosin in the nail polish is 15 to 70% by weight.
  • solvents with low molecular weight are highly volatile and can cause uneven thickness of the coating during application, and the solvent odor is strong, which may cause discomfort to the user, and relatively low molecular weight.
  • the solvent causes inconvenience such as long drying time of the membrane. Therefore, in consideration of these, it is desirable to use them in an appropriate combination according to the solubility of the resin used and the properties of the nail polish after synthesis.
  • a coloring agent or the like can be added to the nail material of the present invention.
  • a nacreous powder with nacreous or Z and dyed nacreous powder with nacreous can be blended. It is possible to make a nail polish by adding pigments such as Sarako, Titanium and Bengala, UV absorbers, etc., but the blending amount is not inconsistent with the gist of the present invention.
  • tertiary butyl peroxybivalate (initiator B) was divided into 4 parts, 7 parts, 2 hours and 5 hours after the start of the reaction and after the reaction, and 10 hours later.
  • the nail polish was obtained in the same manner as in Example 1, except that the polymerization reaction was performed for 15 hours, and then the temperature was raised to 20 ° C and maintained at 80 ° C for 5 hours. It was.
  • Example 7 To the composition shown in Table 1, add 6 parts of tertiary butyl peroxyneodecanoate (initiator C), divided into 2 portions at the time of preparation and 10 hours after the start of the reaction. 15 hours A nail polish was obtained in the same manner as in Example 1, except that a polymerization reaction was performed over the course of the reaction, followed by a step of raising the temperature by 20 ° C. and holding at 80 ° C. for 5 hours. [0030] (Example 7)
  • tertiary butyl peroxyneodecanoate (initiator C) was added in two parts, divided into 3 portions at the time of preparation and 3 hours and 10 hours after the start of the reaction.
  • the nail polish was obtained in the same manner as in Example 1, except that the polymerization reaction was performed for 15 hours, and then the temperature was raised to 20 ° C and maintained at 80 ° C for 5 hours. .
  • the nail polish synthesized in the example was applied on a glass plate, and the solvent was dried at room temperature to produce a 0.2 mm film. Using this membrane, measurement was performed at 36 ° C using OX-TRAN 100A manufactured by MOCON.
  • the unit is DK value X 10 "(cmVsec) ⁇ (mLO X mmHg).
  • a sensory evaluation was conducted by visual inspection to determine whether the film peeled off or cracked when applied to the nail o
  • the transparency of the film applied to the nail was subjected to visual sensory evaluation.
  • the amount of the residual monomer contained in the synthesized nail polish was measured by the following procedure using high performance liquid chromatography (Zo, manufactured by JASCO Corporation, HPLC).
  • Residual monomer amount (wZv%) AX 50 X 10 " 4
  • Table 1 shows the compositions of the examples and the evaluation results.
  • Initiator A 2,2'-azobisiso tyronizilyl Initiator B: Tertiary tilperoxy bivalerate Initiator C: Tertiary butyl peroxyneodecano :! :
  • the present invention has good film-forming properties, transparency and oxygen permeability, and can reduce the residual monomer in the copolymer component as much as possible. High! / Amami nail can be provided.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne des préparations pour manucure qui sont excellentes en terme de transparence, de perméabilité à l'oxygène et de pouvoir filmogène, et qui permettent l'utilisation directe d'un copolymère obtenu par synthèse de résine et ont une proportion de monomère non polymérisé contenue dans le copolymère réduite au minimum ; et un procédé pour produire celles-ci. La présente invention concerne des préparations pour manucure perméables à l'oxygène caractérisées en ce qu'elles contiennent un copolymère produit à partir d'un monomère de silicone ayant un groupe fonctionnel polymérisable par voie radicalaire, un monomère ayant un groupe carboxyle ou phosphate et un groupe fonctionnel polymérisable par voie radicalaire dans chaque molécule et un monomère ayant un groupe fonctionnel polymérisable par voie radicalaire copolymérisable avec ceux-ci, le taux de monomère résiduel étant de 0,5 % ou moins.
PCT/JP2005/021430 2005-11-22 2005-11-22 Preparation pour manucure et procede pour produire celle-ci WO2007060710A1 (fr)

Priority Applications (1)

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PCT/JP2005/021430 WO2007060710A1 (fr) 2005-11-22 2005-11-22 Preparation pour manucure et procede pour produire celle-ci

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018140945A (ja) * 2017-02-27 2018-09-13 ピアス株式会社 人工爪用組成物、人工爪、除去液、及び人工爪用キット
CN109715135A (zh) * 2016-09-23 2019-05-03 株式会社目立康 美甲用化妆品组合物、其使用方法和美甲用化妆品树脂

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0225411A (ja) * 1988-07-12 1990-01-26 Kobayashi Kose Co Ltd 化粧料
JPH06166859A (ja) * 1992-12-01 1994-06-14 Sekisui Chem Co Ltd アクリル系粘着剤の製造方法
JPH0948718A (ja) * 1995-08-03 1997-02-18 Kao Corp 水性ネイルエナメル用香料組成物
JPH09183711A (ja) * 1995-12-29 1997-07-15 Kose Corp 美爪料
JP2001151642A (ja) * 1999-11-22 2001-06-05 Kose Corp 美爪料
JP2001172310A (ja) * 1999-12-16 2001-06-26 Wako Pure Chem Ind Ltd 新規な重合方法
JP2002265390A (ja) * 2001-03-13 2002-09-18 Nitto Denko Corp 医療用アクリル系粘着剤の製造方法
JP2003342128A (ja) * 2002-05-29 2003-12-03 Mikimoto Pharmaceut Co Ltd 美爪料及びその製造方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0225411A (ja) * 1988-07-12 1990-01-26 Kobayashi Kose Co Ltd 化粧料
JPH06166859A (ja) * 1992-12-01 1994-06-14 Sekisui Chem Co Ltd アクリル系粘着剤の製造方法
JPH0948718A (ja) * 1995-08-03 1997-02-18 Kao Corp 水性ネイルエナメル用香料組成物
JPH09183711A (ja) * 1995-12-29 1997-07-15 Kose Corp 美爪料
JP2001151642A (ja) * 1999-11-22 2001-06-05 Kose Corp 美爪料
JP2001172310A (ja) * 1999-12-16 2001-06-26 Wako Pure Chem Ind Ltd 新規な重合方法
JP2002265390A (ja) * 2001-03-13 2002-09-18 Nitto Denko Corp 医療用アクリル系粘着剤の製造方法
JP2003342128A (ja) * 2002-05-29 2003-12-03 Mikimoto Pharmaceut Co Ltd 美爪料及びその製造方法

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109715135A (zh) * 2016-09-23 2019-05-03 株式会社目立康 美甲用化妆品组合物、其使用方法和美甲用化妆品树脂
US11278489B2 (en) 2016-09-23 2022-03-22 Menicon Co., Ltd. Cosmetic composition for nails, method of using same, and cosmetic resin for nails
CN109715135B (zh) * 2016-09-23 2023-01-24 株式会社目立康 美甲用化妆品组合物、其使用方法和美甲用化妆品树脂
JP2018140945A (ja) * 2017-02-27 2018-09-13 ピアス株式会社 人工爪用組成物、人工爪、除去液、及び人工爪用キット

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