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WO2000020478A1 - Composition de resine liquide polymerisable - Google Patents

Composition de resine liquide polymerisable Download PDF

Info

Publication number
WO2000020478A1
WO2000020478A1 PCT/NL1999/000609 NL9900609W WO0020478A1 WO 2000020478 A1 WO2000020478 A1 WO 2000020478A1 NL 9900609 W NL9900609 W NL 9900609W WO 0020478 A1 WO0020478 A1 WO 0020478A1
Authority
WO
WIPO (PCT)
Prior art keywords
acrylate
meth
compound
composition
liquid curable
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.)
Ceased
Application number
PCT/NL1999/000609
Other languages
English (en)
Inventor
Masanobu Sugimoto
Takashi Ukachi
Zen Komiya
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.)
JSR Corp
Koninklijke DSM NV
Original Assignee
JSR Corp
DSM NV
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 JSR Corp, DSM NV filed Critical JSR Corp
Publication of WO2000020478A1 publication Critical patent/WO2000020478A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
    • C03C25/10—Coating
    • C03C25/104—Coating to obtain optical fibres
    • C03C25/106—Single coatings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen

Definitions

  • a polymerizable monofunctional or polyfunctional compound can be added to the liquid curable resin composition of the present invention.
  • the mono-functional compound which can be used in the composition of the present invention are vinyl group-containing lactams such as N-vinyl pyrrolidone and N-vinyl caprolactam; (meth) acrylates containing an alicyclic structure such as isobornyl (meth) acrylate, bornyl (meth) acrylate, tricyclodecanyl (meth) acrylate, and dicyclopentanyl (meth) acrylate; benzyl (meth) acrylate, 4-butylcyclohexyl (meth) acrylate, acryloylmorpholine, vinyl imidazole, and vinylpyridine .
  • R 6 and R 8 individually represent a hydrogen atoms or methyl group
  • R 7 and R 9 individually represent an alkylene group having 2-8, preferably 2-5, carbon atoms
  • R 10 to R 15 individually represent a hydrogen atom or methyl group
  • p and q individually indicate an integer from 0 to 5 , preferably from 1 to 4,
  • Lucirin TPO manufactured by BASF
  • Ubecryl P36 manufactured by Ubecryl P36
  • the photosensitizer triethylamine, diethylamine, N- methyldiethanoleamine, ethanolamine, 4- dimethylaminobenzoic acid, 4 -methyl dimethylaminobenzoate, 4 -ethyl dimethylaminobenzoate, 4-isoamyl dimethylaminobenzoate, and Ubecryl P102, 103, 104, 105 (manufactured by UCB) can be given.
  • a reaction vessel equipped with a stirrer was charged with 16.98 g of 2,4-tolylene diisocyanate, 0.015 g of 2, 6-di-t-butyl-p-cresol, 0.05 g of dibutyltin dilaurate, and 0.005 g of phenothiazine.
  • the mixture was cooled with ice to 10°C or below while stirring.
  • 11.32 g of 2 -hydroxyethyl acrylate was added dropwise while controlling the temperature of the solution to 20°C or below, following which the mixture was reacted for one hour while stirring.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention porte sur une composition de résine liquide polymérisable utilisable comme revêtement pour les plastiques, les métaux, le bois, les fibres optiques, ou comme constituant de composants optiques. Ladite résine est un urétane (meth)acrylate obtenu en faisant réagir: (a) un diol de formule (1), où X1 et X2 représentent individuellement un atome d'hydrogène ou un groupe méthyle, Y1 à Y16 représentent individuellement un atome d'hydrogène ou un groupe alkyle C¿1-8?, a est un entier de 0 à 5, (b) est un diisocyanate, et (c) un (meth) acrylate comportant un groupe hydroxyle sur un résidu ester.
PCT/NL1999/000609 1998-10-05 1999-09-30 Composition de resine liquide polymerisable Ceased WO2000020478A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP10/282407 1998-10-05
JP28240798A JP3991472B2 (ja) 1998-10-05 1998-10-05 液状硬化性樹脂組成物

Publications (1)

Publication Number Publication Date
WO2000020478A1 true WO2000020478A1 (fr) 2000-04-13

Family

ID=17652019

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NL1999/000609 Ceased WO2000020478A1 (fr) 1998-10-05 1999-09-30 Composition de resine liquide polymerisable

Country Status (2)

Country Link
JP (1) JP3991472B2 (fr)
WO (1) WO2000020478A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130284262A1 (en) * 2010-12-02 2013-10-31 Nissan Chemical Industries, Ltd. Film-forming material

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4821175B2 (ja) * 2005-05-26 2011-11-24 Ｊｓｒ株式会社 ウレタン（メタ）アクリレート、放射線硬化性組成物、及びその硬化膜
JP5297030B2 (ja) * 2006-12-25 2013-09-25 大阪瓦斯株式会社 フルオレン骨格を有するウレタン（メタ）アクリレート
JP2014062195A (ja) * 2012-09-21 2014-04-10 Ksm Kk 光硬化性組成物、及び、光硬化性組成物の製造方法
JP6270513B2 (ja) * 2013-02-13 2018-01-31 大阪ガスケミカル株式会社 フルオレン骨格を有するポリウレタン樹脂
JP2017132859A (ja) * 2016-01-26 2017-08-03 アイカ工業株式会社 プリズム形成用光硬化性樹脂組成物

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4663412A (en) * 1984-10-31 1987-05-05 Ecoplastics Limited Fluorene containing compounds and negative photoresist compositions therefrom
WO1992003483A1 (fr) * 1990-08-16 1992-03-05 Minnesota Mining And Manufacturing Company Melanges polymeres et procedes relatifs a ceux-ci
US5109097A (en) * 1990-09-07 1992-04-28 Minnesota Mining And Manufacturing Company Radiation curable coating
EP0598552A2 (fr) * 1992-11-16 1994-05-25 Sola International Holdings, Ltd. Composition polymérique durcissable
JPH1017632A (ja) * 1996-07-04 1998-01-20 Nippon Kayaku Co Ltd 樹脂組成物、注型用組成物及びその硬化物
JPH1067977A (ja) * 1996-08-28 1998-03-10 Nippon Steel Chem Co Ltd 光ディスク用接着剤及び光ディスク

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4663412A (en) * 1984-10-31 1987-05-05 Ecoplastics Limited Fluorene containing compounds and negative photoresist compositions therefrom
WO1992003483A1 (fr) * 1990-08-16 1992-03-05 Minnesota Mining And Manufacturing Company Melanges polymeres et procedes relatifs a ceux-ci
US5109097A (en) * 1990-09-07 1992-04-28 Minnesota Mining And Manufacturing Company Radiation curable coating
EP0598552A2 (fr) * 1992-11-16 1994-05-25 Sola International Holdings, Ltd. Composition polymérique durcissable
JPH1017632A (ja) * 1996-07-04 1998-01-20 Nippon Kayaku Co Ltd 樹脂組成物、注型用組成物及びその硬化物
JPH1067977A (ja) * 1996-08-28 1998-03-10 Nippon Steel Chem Co Ltd 光ディスク用接着剤及び光ディスク

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 128, no. 14, 6 April 1998, Columbus, Ohio, US; abstract no. 168179, "Urethane (meth)acrylate polymer casting composition" XP002122970 *
CHEMICAL ABSTRACTS, vol. 128, no. 3, 19 January 1998, Columbus, Ohio, US; abstract no. 24966, "adhesives containing polyurethane acrylates with diphenylfluorene structures" XP002122971 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130284262A1 (en) * 2010-12-02 2013-10-31 Nissan Chemical Industries, Ltd. Film-forming material
US9761741B2 (en) * 2010-12-02 2017-09-12 Nissan Chemical Industries, Ltd. Film-forming material

Also Published As

Publication number Publication date
JP3991472B2 (ja) 2007-10-17
JP2000109528A (ja) 2000-04-18

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