EP2686071A2 - Vernis à ongles photodurcissant - Google Patents

Vernis à ongles photodurcissant

Info

Publication number
EP2686071A2
EP2686071A2 EP12709290.6A EP12709290A EP2686071A2 EP 2686071 A2 EP2686071 A2 EP 2686071A2 EP 12709290 A EP12709290 A EP 12709290A EP 2686071 A2 EP2686071 A2 EP 2686071A2
Authority
EP
European Patent Office
Prior art keywords
light
nail
monomer
curing
nail polish
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.)
Withdrawn
Application number
EP12709290.6A
Other languages
German (de)
English (en)
Inventor
Ralf Janda
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.)
Wilde Cosmetics GmbH
Original Assignee
Wilde Cosmetics GmbH
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 Wilde Cosmetics GmbH filed Critical Wilde Cosmetics GmbH
Publication of EP2686071A2 publication Critical patent/EP2686071A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A61Q3/02—Nail coatings
    • A—HUMAN NECESSITIES
    • A45—HAND OR TRAVELLING ARTICLES
    • A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
    • A45D29/00—Manicuring or pedicuring implements
    • A45D29/11—Polishing devices for nails
    • 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
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • 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
    • A61K8/55—Phosphorus compounds
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/81—Preparation or application process involves irradiation

Definitions

  • the present invention relates to a nail polish
  • a light-curing nail varnish for application to a nail, such as a fingernail, toenail, or the like, as well as a method for varnishing a nail with the nail varnish according to the invention.
  • Nail varnish according to the invention allows a simple painting of a nail and provides paint layers that are particularly durable.
  • nail varnishes made from solutions of nitrocellulose in solvents (such as e.g.
  • Ethyl acetate, butyl acetate, methyl ethyl ketone or the like) and other additives pigments, plasticizers, SiO 2 , etc.
  • VOC Directive EU Directive on the limitation of emissions of volatile organic compounds VOC (volatile organic compounds) 1999/13 / EC) emissions from
  • CONFIRMATION COPY To reduce or avoid solvents. In some countries (such as Switzerland) even penalties have to be paid if solvent-based products are imported.
  • nail polishes that can be cured with light (usually UVA light).
  • UVA light usually UVA light.
  • These paints consist for example of mixtures of acrylates, methacrylates, pigments,
  • the fingernail must be roughened large area before application and it must first a special bonding agent
  • Adhesive itself must i.d.R. also be cured with light before application of the paint.
  • these multilayer constructions can not be easily removed with conventional nail polish removers because the monomers used are crosslinkers, such as diioder tri (meth) acrylates, and the resulting polymers are highly crosslinked and thus brittle, as well as insoluble in solvents. They have to be mechanically removed by filing, which with frequent use leads to the natural nail becoming thinner and thinner. Sometimes even low percentages become more monofunctional
  • the present invention provides a nail polish, in particular a light-curing nail polish, which is a photopolymerizable monofunctional
  • Acrylic acid ester monomer and a photoinitiator (Acrylate system).
  • the monofunctional acrylic acid ester monomer comprises at least one monomer which is selected from 2- [[(butylamino) carbonyl] oxy] ethyl acrylate,
  • the present invention provides a method for painting a nail, in which the invention, in particular light-curing nail polish is applied to a nail and brought to polymerization with light.
  • Components must be polymerized quickly and may contain no or only small amounts of crosslinking agents.
  • photohardening has proven to be particularly advantageous.
  • polymerizable conventional monomers are, for example
  • these conventional monomers are not suitable in principle for such a nail polish, especially because they smell very strong and so extremely unpleasant for the user are.
  • these conventional monomers when cross-linked with a photoinitiator, are generally not polymerizable to films, since oxygen-oxygen inhibition is so strong that the products in films do not or only very incompletely cure.
  • Thermoplastic polymers e.g. Polymethyl methacrylate, polystyrene, polyvinyl acetate, polyvinyl butyral or the like can only be dissolved in small amounts (up to about 20%) in conventional monomers because the resulting solution thickens very quickly and becomes extremely viscous, making processing impossible.
  • a monomer such as e.g. Polymethylmethacrylate, usually residual amounts of initiator, e.g. Dibenzoyl peroxide, which results from its synthesis, so that the solutions do not have sufficient storage stability even at room temperature.
  • Methyl methacrylate, ethyl methacrylate, butyl methacrylate, Isobornyl acrylate, tetrahydrofurfuryl methacrylate, or the like with the respective dissolved polymers are used, become very brittle products after curing
  • Monomers in very large amounts can be solved.
  • Such admixed with photoinitiator mixtures can, in particular at optimized content of sucrose benzoate, applied in desired thicknesses on the natural nail and polymerized to high-gloss films. Since both the uncrosslinked polymers, and in particular sucrose benzoate in many solvents are very soluble, the
  • Used skin cleansers that are used to remove oils and other fatty substances from the skin.
  • Plasticizers eg phthalate or citrate-based
  • this approach was also unsuitable, since the large amounts of plasticizer needed (up to about 5%) reduce the intrinsic strength of the material to such an extent that, although in the
  • Unloaded state is no longer brittle, that is, when wearing on the fingernail not immediately splintered, but already after 1 to 2 days of desquamation occur.
  • a nail varnish of the invention which is suitable for solving the problem must contain a monofunctional monomer which polymerizes to give a highly elastic and tear-resistant polymer.
  • this monofunctional monomer should result in films that are high gloss.
  • sucrose benzoate should be soluble in large quantities, and by the monomer
  • the monofunctional monomers are 2- [[(butylamino) carbonyl] oxy] ethyl acrylate (or 2- (((butylamino) carbonyl) oxy) ethyl ester; CAS No. 63225-53-6; 1),
  • Ethoxylated (4) nonylphenol acrylate (CAS No. 50974-47-5; Formula 2) and ethoxylated (8) nonylphenol acrylate (CAS No. 50974-47-5; Formula 3) all have the desired properties: a high dissolving power for sucrose benzoate, as well as for
  • thermoplastic polymers such as polyvinyl acetate or
  • Ethoxylated (8) onylphenol acrylate Sucrose benzoate refers to a sucrose molecule, as it is preferably completely esterified with benzoic acid (CAS N 12738-64-6, Formula 4).
  • acrylate / methacrylate systems whether cross-linked or uncross-linked, exhibit more or less strong atmospheric oxygenation after photohardening
  • oils in oils and oils are isopropyl myristate, castor oil, jojoba oil, almond oil and sunflower oil
  • the monomer 2- [[(butylamino) carbonyl] oxy] ethyl acrylate can be obtained, for example, under the trade name "Genomer 1122" from Rahn AG, Zurich, Switzerland.
  • Ethoxylated (8) nonylphenol acrylate can be obtained, for example, under the trade names Miramer M164 and Miramer M166 from Miwon Ltd., Kyonggi, Korea.
  • These monomers may be used alternatively or in mixture.
  • the photoinitiator can be any conventional photoinitiator used to initiate a photoinitiator
  • Polymerization reaction of an acrylate system is suitable.
  • Preferred examples of suitable photoinitiators are:
  • Lucirin TPO-L ethyl (2, 6-trimethylbenzoyl) phenylphosphinate.
  • a light-curing nail varnish in the sense of this invention comprises a photopolymerizable acrylate system which comprises
  • photoinitiator Includes or consists of photoinitiator.
  • light-curing or “photopolymerizable” used to indicate that the photoinitiator contained in the systems described by irradiation with light (electromagnetic radiation), in particular light in the UV range with a
  • Wavelength of 340 to 430 nm (UVA light) can be reacted, resulting in a polymerization reaction (chain-forming reaction) of the monofunctional
  • Acrylic acid ester monomers is started, which leads to the formation of a polymer from monomer units.
  • the polymerization of the acrylate / methacrylate monomers takes place radically.
  • the nail varnish according to the invention preferably comprises from 30 to 99% (unless stated otherwise, all data are% by weight) of monomer and from 1 to 10% photoinitiator, more preferably from 39 to 85% monomer and from 1 to 7% photoinitiator.
  • Sucrose benzoate and / or a thermoplastic polymer particularly preferably polyvinyl acetate and / or polyvinyl butyral. Particularly preferred is a polyvinyl acetate having a molecular weight of 10,000 to 100,000.
  • a polyvinyl butyral having a molecular weight of 50,000 to 120,000.
  • the molecular weight or molecular weight of the polymers can be determined, for example, by size exclusion chromatography using a small-angle laser scattering detector (size exclusion
  • thermoplastic polyvinyl butyrals used are taken, for example, from the product group Butvar from Solutia Europe, Belgium. Preference is given to Products B-90, molecular weight 70000-100000, B-79, molecular weight 50000-800000, B-98, molecular weight 40000-70000 and B-76, molecular weight 90000- 120000 used.
  • the extensibilities of these products are given as values of 100 to 110% and the glass transition temperatures as 62 to 78 ° C.
  • the extensibility of the polymers can be determined, for example, by standard tensile testing, and the glass transition temperature can be determined, for example, by differential scanning calorimetry (DSC), for example in accordance with DIN 53765 / ISO 11357-5.
  • DSC differential scanning calorimetry
  • thermoplastic polyvinyl acetates used (CAS no.
  • B 5 sp molar mass 20000-25000
  • B 14 sp molar mass 25000-33000
  • B 17 sp molar mass 35000-45000
  • B 30 sp 45000-55000 molar mass B 60 sp, molar mass 55000-70000 and B 100 .
  • Glass transition temperature can be determined, for example, by Differential Scanning Calometry (DSC), e.g. according to DIN 53765 / ISO 11357-5.
  • DSC Differential Scanning Calometry
  • the nail varnish according to the invention preferably comprises from 10 to 70%, more preferably from 30 to 45%, and especially from 34 to 41% sucrose benzoate, and / or from 2 to 20%
  • thermoplastic polymer preferably from 1 to 11%, and more preferably from 1 to 5% of a thermoplastic polymer.
  • methacrylate monomers for example, isobornyl methacrylate, 2-hydroxyethyl methacrylate (HEMA; CAS No. 868-77-9),
  • 3-hydroxypropyl methacrylate (HPMA; CAS No. 27813-02-1) or tetrahydrofurfuryl methacrylate may be added in amounts of up to 15%, without any of this for the purpose; too high brittleness occurs.
  • HPMA 3-hydroxypropyl methacrylate
  • tetrahydrofurfuryl methacrylate may be added in amounts of up to 15%, without any of this for the purpose; too high brittleness occurs.
  • nail polish according to the invention preferably from 30 to 99%
  • Acrylate / methacrylate monomer more preferably from 39 to 85% monomer.
  • crosslinking monomers Preferably, it is also possible to add small amounts of crosslinking monomers to the preparations. Particularly preferred are:
  • Abrasion resistance of the films if necessary, be improved.
  • Particularly preferred diacrylates and dimethacrylates are:
  • Bis-GMA 2, 2-bis [4 (3'-methacryloyl-oxy-2'-hydroxy) propoxyphenyl] propane (CAS No. 1565-94-2);
  • Bis-EDMA 2, 2-bis [4 (3'-methacryloyl-oxy) ethoxyphenyl)] propane;
  • TEGDMA triethylene glycol dimethacrylate
  • adhesion promoters may preferably be added. These may preferably be added up to an amount of 10%, more preferably up to an amount of 5%. Preferred examples of adhesion promoters are:
  • PMGD bis (glyceryl dimethacrylate) pyromellitate (CAS no.
  • 4-meta 4-methacryloyl-oxypropyltrimellitic anhydride
  • MDP 10-methacryloyl-oxy-decyl dihydrogen phosphate
  • the nail varnish according to the invention can advantageously be applied to a nail and then brought to polymerization with light.
  • the polymerization is particularly preferably carried out with light having a wavelength of 340 to 430 nm.
  • a conventional polymerization light device can be used, the light source as UV fluorescent tubes whose
  • Emission maximum is about 370 nm, or an LED device with an emission maximum at about 400 nm.
  • the polymerized lacquer layers are shiny and can easily with conventional, even acetone-free
  • Nail polish removers to be removed again.
  • nail polish according to the invention after application and polymerization compared to conventional solvent-based nail polishes, depending on the stress, about 5 to 10 times greater.
  • the Application of a nail polish according to the invention must therefore be renewed 5 to 10 times less frequently.
  • the nail varnish according to the invention has an immediate strength by light curing.
  • Coating layers are characterized by a very good removability.
  • the inventive nail polish may preferably also comprise further additives, for example a colorant and / or a filler.
  • Preferred colorants are dyes, such as
  • Food colors Preferred examples include:
  • Examples include:
  • Preferred fillers are, for example, fumed silicas (silica), as used, for example, under the trade name
  • the inventive nail polish may also comprise other additives, such as an optical brightener or whitening agent, e.g. 2, 5-Thiophenediylbis (5-tert-butyl-1,3-benzoxazole) (Formula 5).
  • an optical brightener or whitening agent e.g. 2, 5-Thiophenediylbis (5-tert-butyl-1,3-benzoxazole) (Formula 5).
  • 5-Thiophenediylbis (5-tert-butyl-1,3-benzoxazole) is available, for example, under the trade name Tinopal OB from Ciba Spezialitätenchemie, Germany.
  • the color consistency is advantageously ensured when curing in different polymerization light devices. For example, curing in a UV fluorescent tube device with tubes whose emission maximum is about 370 nm, as is currently the most commonly used in the market, or in an LED device whose
  • a suitable whitening agent is, for example, the 2,5-thiophenediylbis (5-tert-butyl-1,3-benzoxazole) shown in formula 5.
  • the curing in the UV fluorescent tube device can be adversely affected in deeper material layers or
  • the nail varnish of the present invention comprises 0.10% or less of a whitening agent, more preferably 0.05% or less, more preferably 0.0005 to 0.01%, and particularly preferably 0.0008 to 0.005%.
  • a whitening agent more preferably 0.05% or less, more preferably 0.0005 to 0.01%, and particularly preferably 0.0008 to 0.005%.
  • nail polish according to the invention 0.001% 2, 5-thiophenediylbis (5-tert-butyl-1,3-benzoxazole).
  • Lucirin TPO-L ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate
  • the formulations of all examples are liquid and can be easily applied to a nail where they adhere well. After polymerization with light in the wavelength range of 350 to 420 nm, they produce glossy coating layers which adhere very well to the nail and are particularly impact-resistant.
  • lacquer layers can be easily removed with conventional, even acetone-free nail polish remover.
  • Loss total loss of nail polish coating. The practical test was carried out for each material version with 15 test persons in such a way that the nails of one hand were coated with one version and those of the other hand with a different version. Thus, two material versions could be tested simultaneously on one subject group.
  • the observation time was 1, 3 and 5 days.
  • Fingernail refers.
  • 7 observations in the category "lifting" mean that at 7 coated fingernails for the material concerned detachments at the edges
  • nail polish remover used is as follows: 60% ethyl acetate, 37% isopropyl alcohol, 2% butylene glycol, 1% Ricinus Communis (Castor) Seed Oil.
  • the nail varnish of the respective example was applied to a slide with a brush of application-relevant layer thickness (about 0.1 mm) and area (about 1 ⁇ 1 cm).
  • the cellulose cloth was soaked with the nail polish remover and placed on the varnish layer for about 10 seconds. Then, similar to the actual removal of a nail polish from the finger, the pulp cloth impregnated with nail polish remover was moved under pressure over the varnish layer under rubbing motion. The time was stopped until the entire nail polish layer had been removed from the slide.

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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 un vernis à ongles, en particulier un vernis à ongles photodurcissant, à appliquer sur des ongles, comme par exemple des ongles de mains, des ongles de pieds ou similaires, ainsi qu'un procédé pour appliquer ledit vernis à ongles sur des ongles. Le vernis à ongles selon l'invention est aisé à appliquer et permet d'obtenir des couches de vernis qui tiennent particulièrement bien.
EP12709290.6A 2011-03-16 2012-03-15 Vernis à ongles photodurcissant Withdrawn EP2686071A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102011014149A DE102011014149B4 (de) 2011-03-16 2011-03-16 Lichthärtender Nagellack
PCT/EP2012/001166 WO2012123123A2 (fr) 2011-03-16 2012-03-15 Vernis à ongles photodurcissant

Publications (1)

Publication Number Publication Date
EP2686071A2 true EP2686071A2 (fr) 2014-01-22

Family

ID=45852511

Family Applications (1)

Application Number Title Priority Date Filing Date
EP12709290.6A Withdrawn EP2686071A2 (fr) 2011-03-16 2012-03-15 Vernis à ongles photodurcissant

Country Status (4)

Country Link
US (1) US20140000640A1 (fr)
EP (1) EP2686071A2 (fr)
DE (1) DE102011014149B4 (fr)
WO (1) WO2012123123A2 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2998787B1 (fr) * 2012-12-05 2015-01-16 Oreal Composition adhesive photoreticulable pour le maquillage et/ou le soin des ongles
FR3048609B1 (fr) 2016-03-08 2019-06-14 Fiabila Sas Compositions pour vernis a ongles
JP6886302B2 (ja) * 2016-06-01 2021-06-16 ミネベアミツミ株式会社 紫外線硬化性樹脂組成物及び摺動部材
US10167439B2 (en) * 2016-06-01 2019-01-01 Minebea Mitsumi Inc. Ultraviolet curable resin composition and sliding member
LU100763B1 (fr) * 2018-04-10 2019-10-11 Int Lacquers S A Compositions améliorées applicables sur les ongles
TWM568066U (zh) * 2018-04-19 2018-10-11 鄭國章 Manicure device with light absorbing chamber
JP7541416B1 (ja) 2023-12-27 2024-08-28 株式会社ネイルセレクト 爪用組成物

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JPS60215607A (ja) * 1984-04-11 1985-10-29 Shiseido Co Ltd 美爪料
US5456905A (en) * 1988-08-23 1995-10-10 Ultraset Limited Partnership Quick-drying nail coating method and composition
GB9603667D0 (en) * 1996-02-21 1996-04-17 Coates Brothers Plc Ink composition
EP1375618A1 (fr) * 2002-06-19 2004-01-02 3M Innovative Properties Company Présurseur sans solvant imprimable d'un adhésif réticulable par radiation
DE102005045441A1 (de) * 2005-09-22 2007-05-03 Henkel Kgaa Beschichtungsmittel für Metalloberflächen mit antiadhäsiven Eigenschaften
EP1790696B1 (fr) * 2005-11-28 2013-04-10 Agfa Graphics N.V. Dispersions de pigment non-aqueuses contenant des synergistes de dispersion spécifiques

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Also Published As

Publication number Publication date
DE102011014149A1 (de) 2012-09-20
WO2012123123A3 (fr) 2013-10-17
US20140000640A1 (en) 2014-01-02
WO2012123123A2 (fr) 2012-09-20
DE102011014149B4 (de) 2013-04-04

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