EP0000890B1 - Strahlenhärtbare Urethanacrylat-Bindemittel - Google Patents

Strahlenhärtbare Urethanacrylat-Bindemittel Download PDF

Info

Publication number
EP0000890B1
EP0000890B1 EP78100602A EP78100602A EP0000890B1 EP 0000890 B1 EP0000890 B1 EP 0000890B1 EP 78100602 A EP78100602 A EP 78100602A EP 78100602 A EP78100602 A EP 78100602A EP 0000890 B1 EP0000890 B1 EP 0000890B1
Authority
EP
European Patent Office
Prior art keywords
groups
thio
acid
polyol
und
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
Application number
EP78100602A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0000890A2 (de
EP0000890A3 (en
Inventor
Karl-Ernst Dr. Schuster
Hans Jürgen Dr. Rosenkranz
Hans Dr. Rudolph
Karl Dr. Fuhr
Bruno Dr. Zorn
Harro Dr. Träubel
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of EP0000890A2 publication Critical patent/EP0000890A2/de
Publication of EP0000890A3 publication Critical patent/EP0000890A3/xx
Application granted granted Critical
Publication of EP0000890B1 publication Critical patent/EP0000890B1/de
Expired legal-status Critical Current

Links

Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
    • 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
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3863—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
    • C08G18/4676—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing sulfur
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5072—Polyethers having heteroatoms other than oxygen containing sulfur
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
    • C08G18/6453—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having sulfur
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable

Definitions

  • polyisocyanates are understood to mean di- and higher-functional isocyanates, preferably di- and trifunctional, in particular difunctional. Examples include: tolylene diisocyanates, diphenylmethane diisocyanates, isophorone diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate.
  • reaction products according to the invention can be used without the addition of copolymerizable monomers or solvents. However, since in many cases the products are viscous, it is advisable to mix them with copolymerizable monomers in order to obtain viscosities suitable for processing and / or to vary the properties of the curing products.
  • the coating agents can be applied to suitable substrates by means of methods customary in the paint industry, such as spraying, rolling, knife coating, printing, dipping, flooding, brushing, brushing.
  • the mixture is stirred at 60 ° C. under dry air until the NCO value is 0.1% by weight. A colorless and odorless, medium-viscosity resin is created.
  • a prepolymeric urethane acrylate according to Example 1 is produced, but with the change that instead of 6.1 g of thiodiglycol, 22.4 g of a polyester made from triethylene glycol and methylene bisthioglycolic acid (OH number: 250) are used.
  • 35 g of a bisepoxide based on hexahydrophthalic acid bisglycidyl ester (epoxy equivalent weight: 175) are reacted with 40 g undecane carboxylic acid at 90 ° C. to an acid number of 0.
  • the reaction product is then reacted with 34.8 g of tolylene diisocyanate and then with 23 g of hydroxyethyl acrylate.
  • the result is a resin with an NCO content of ⁇ 0.1% by weight.
  • a customary, red-colored primer consisting of a soft polyacrylate binder (approx. 25 Shore A), albumin and a medium-hard butadiene-acrylonitrile binder (approx. 40 Shore A) sprayed on, dried, ironed, embossed and then uniformly sprayed on the UV-light-curable mixture mentioned in Example 4 and diluted 1: 1 with ethyl acetate. After curing (polymerizing) using a Hanovia lamp, a glossy, rubbing and solvent-resistant finish was obtained.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Paints Or Removers (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
EP78100602A 1977-08-19 1978-08-07 Strahlenhärtbare Urethanacrylat-Bindemittel Expired EP0000890B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772737406 DE2737406A1 (de) 1977-08-19 1977-08-19 Strahlenhaertbare bindemittel
DE2737406 1977-08-19

Publications (3)

Publication Number Publication Date
EP0000890A2 EP0000890A2 (de) 1979-03-07
EP0000890A3 EP0000890A3 (en) 1979-05-16
EP0000890B1 true EP0000890B1 (de) 1980-10-01

Family

ID=6016785

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100602A Expired EP0000890B1 (de) 1977-08-19 1978-08-07 Strahlenhärtbare Urethanacrylat-Bindemittel

Country Status (6)

Country Link
US (1) US4225695A (it)
EP (1) EP0000890B1 (it)
JP (1) JPS5448888A (it)
DE (2) DE2737406A1 (it)
ES (1) ES472667A1 (it)
IT (1) IT1106885B (it)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2822190A1 (de) * 1978-05-20 1979-11-22 Hoechst Ag Photopolymerisierbares gemisch
DE2945549A1 (de) 1979-11-10 1981-05-21 Röhm GmbH, 6100 Darmstadt Fluesiges, durch uv-strahlung haertbares ueberzugs- und bindemittel
IE50670B1 (en) * 1979-12-24 1986-06-11 Agfa Gevaert Ag Process for the production of forgery-proof documents
US4305996A (en) * 1980-03-10 1981-12-15 The B. F. Goodrich Company Hydroxyl-containing liquid polymers and adhesives made therefrom
US4349656A (en) * 1980-07-23 1982-09-14 American Cyanamid Company Thiodiethanol based polyurethane elastomers having improved dynamic properties and method for production thereof
DE3048502A1 (de) * 1980-12-22 1982-07-22 Hoechst Ag, 6000 Frankfurt Durch strahlung polymerisierbares gemisch und daraus hergestelltes strahlungsempfindliches aufzeichnungsmaterial
US4435497A (en) * 1981-06-19 1984-03-06 Ciba-Geigy Corporation Carboxyl-containing compositions and their polymerization
US4484204A (en) * 1982-04-10 1984-11-20 Kanzaki Paper Manufacturing Co., Ltd. Heat-sensitive record material
DE3235610A1 (de) * 1982-09-25 1984-03-29 Bayer Ag, 5090 Leverkusen Strahlenhaertbares grundiermittel und seine verwendung
FR2540131B1 (fr) * 1983-01-28 1986-04-04 Atochem Compositions et procede pour le traitement oleophobe et hydrophobe des materiaux de construction
JPS60101532A (ja) * 1983-11-09 1985-06-05 Nippon Soda Co Ltd メツキ用レジスト樹脂組成物
JPS61179216A (ja) * 1985-02-04 1986-08-11 Sanyo Kokusaku Pulp Co Ltd 光硬化性樹脂組成物
AU2280888A (en) * 1987-10-12 1989-04-13 Takeda Chemical Industries Ltd. Polyurethane resins having mercapto groups, use in magnetic recording medium
DE4026885A1 (de) * 1990-08-25 1992-02-27 Bayer Ag (meth)acryloylgruppen enthaltende polyurethane, ein verfahren zu ihrer herstellung und ihre verwendung
DE4027743A1 (de) * 1990-09-01 1992-03-05 Bayer Ag Acryloylgruppen enthaltende, aliphatische polyurethane, ein verfahren zu ihrer herstellung und ihre verwendung
DE4027971A1 (de) * 1990-09-04 1992-03-05 Bayer Ag Acryloylgruppen enthaltende, aliphatische polyurethane, ein verfahren zu ihrer herstellung und ihre verwendung
JPH04311714A (ja) * 1991-04-09 1992-11-04 Nippon Paint Co Ltd 光硬化性樹脂組成物
DE4141720A1 (de) * 1991-12-18 1993-06-24 Bayer Ag Verfahren zur herstellung von acryloylgruppen enthaltenden, aliphatischen polyurethanen und ihre verwendung
DE4232013A1 (de) * 1992-09-24 1994-03-31 Bayer Ag Acryloylgruppen aufweisende Polyurethane, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Bindemittel für Überzugsmassen
DE4305162A1 (de) * 1993-02-19 1994-08-25 Bayer Ag Olefinisch ungesättigte Isocyanate
DE4343885A1 (de) * 1993-12-22 1995-06-29 Hoechst Ag Wäßrige, strahlenhärtbare Bindemitteldispersionen
JP3292657B2 (ja) * 1995-04-10 2002-06-17 キヤノン株式会社 薄膜トランジスタ及びそれを用いた液晶表示装置の製造法
US5744514A (en) * 1996-10-31 1998-04-28 Borden Chemical, Inc. Coated optical fibers having a reduced content of extractable and volatile material
US6986132B1 (en) 2000-04-28 2006-01-10 Sun Microsytems, Inc. Remote incremental program binary compatibility verification using API definitions
EP2051251A1 (en) 2007-10-19 2009-04-22 Bayer MaterialScience AG Disc shaped high density recording medium
EP2212366A1 (en) * 2007-11-19 2010-08-04 Cytec Surface Specialties, S.A. Radiation curable compositions
DE102008004622A1 (de) 2008-01-16 2009-07-23 Bayer Materialscience Ag Silikahaltige UV-vernetzbare Hardcoatbeschichtungen mit Urethanacrylaten
CN102549081A (zh) 2009-10-16 2012-07-04 拜尔材料科学股份公司 单层和多层的高折射、耐刮擦的TiO2 涂层
JP2014526958A (ja) * 2011-07-14 2014-10-09 ディーアイシー・イメージング・プロダクツ・ユーエスエー・エルエルシー 高屈折率の紫外線硬化型コーティングを利用する、損傷した光学基板を復元するための方法及び組成物
JP5321721B2 (ja) * 2011-08-19 2013-10-23 富士ゼロックス株式会社 樹脂材料
DE102011053030A1 (de) 2011-08-26 2013-02-28 Bayer Materialscience Aktiengesellschaft Solarmodul und Verfahren zu seiner Herstellung
WO2016160410A1 (en) 2015-04-02 2016-10-06 E I Du Pont De Nemours And Company Polymeric gravure printing form and process for preparing the same with curable composition having a multifunctional urethane
US20200122448A1 (en) 2017-05-22 2020-04-23 Covestro Deutschland Ag Films having a scratch-resistant coating as a cover layer and layered composites comprising such films
EP4043502B1 (de) 2021-02-11 2023-10-04 Xetos AG Photopolymerisierbare hoe-zusammensetzung

Family Cites Families (11)

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Publication number Priority date Publication date Assignee Title
US2806836A (en) 1952-10-14 1957-09-17 Bayer Ag Diisocyanate modified polyester copolymer and process of making same
US3297745A (en) * 1962-04-05 1967-01-10 Robertson Co H H Ethylenically unsaturated di-and tetra-urethane monomers
US3509234A (en) * 1965-08-13 1970-04-28 Ford Motor Co Radiation curable paint binders containing vinyl monomers and a hydroxylated polymer reacted with a polyisocyanate and an hydroxyl alkyl acrylate
US3396210A (en) * 1965-09-20 1968-08-06 Ashland Oil Inc Compositions made from: (a) isocyanateterminated prepolymers; and (b) polyesters prepared from polyols and alpha, beta-ethylenically unsaturated monocarboxylic acids
US3600359A (en) * 1968-11-21 1971-08-17 Brien Corp O Novel thiourethane-urethane acrylates
US3700643A (en) * 1970-09-02 1972-10-24 Union Carbide Corp Radiation-curable acrylate-capped polycaprolactone compositions
JPS5034964B1 (it) * 1970-03-30 1975-11-12
JPS529234B2 (it) * 1973-05-10 1977-03-15
DE2433908A1 (de) * 1974-07-15 1976-02-05 Basf Ag Strahlungshaertbare ueberzugsmassen
GB1495004A (en) * 1974-09-06 1977-12-14 Shell Int Research Uv-curable resinous compounds and compositions
UST951007I4 (it) 1975-10-20 1976-10-05

Also Published As

Publication number Publication date
DE2860194D1 (en) 1981-01-08
IT7850755A0 (it) 1978-08-17
US4225695A (en) 1980-09-30
EP0000890A2 (de) 1979-03-07
JPS5448888A (en) 1979-04-17
EP0000890A3 (en) 1979-05-16
DE2737406A1 (de) 1979-02-22
ES472667A1 (es) 1979-02-16
JPS6315293B2 (it) 1988-04-04
IT1106885B (it) 1985-11-18

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