WO2006083343A1 - Resines sequencees a acrylate/ether de vinyle, compositions et procedes de fabrication - Google Patents

Resines sequencees a acrylate/ether de vinyle, compositions et procedes de fabrication Download PDF

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Publication number
WO2006083343A1
WO2006083343A1 PCT/US2005/040856 US2005040856W WO2006083343A1 WO 2006083343 A1 WO2006083343 A1 WO 2006083343A1 US 2005040856 W US2005040856 W US 2005040856W WO 2006083343 A1 WO2006083343 A1 WO 2006083343A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
block copolymer
vinyl ether
composition
acrylate
Prior art date
Application number
PCT/US2005/040856
Other languages
English (en)
Inventor
John G. Woods
Joel D. Schall
Steven T. Nakos
Anthony F. Jacobine
Original Assignee
Henkel Corporation
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 Henkel Corporation filed Critical Henkel Corporation
Priority to US11/814,584 priority Critical patent/US20080139687A1/en
Publication of WO2006083343A1 publication Critical patent/WO2006083343A1/fr

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Classifications

    • 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
    • C08G18/3212—Polyhydroxy compounds containing cycloaliphatic 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • 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
    • C08G18/6715—Unsaturated monofunctional alcohols or amines
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds

Definitions

  • polyurethane block copolymer including the structure:
  • composition including: (a) a polyurethane block copolymer including the structure:
  • a method for using the compositions of the present invention to seal together two substrates including the steps of: (a) applying the composition to at least one of two substrate surfaces; (b) mating the substrate surfaces in abutting relationship to form an assembly; (c) exposing the composition to an energy source selected from radiation, heat and combinations thereof; and (d) maintaining the abutting relationship for a time sufficient to allow the composition to cure.
  • soft segment a segment that may contain primarily linear aliphatic moieties.
  • the linear aliphatic moieties may include an aliphatic ether or ester or a linear aliphatic moiety containing internal unsaturation, such as hydrocarbon elastomers derived from polybutadienes.
  • Pendant functional groups, including aromatic, heterocyclic and cycloaliphatic, among others, may be present in the soft segment, provided that there is no substantial interference with the desired flexible nature of the segment nor degradation of the cured resin properties disclosed herein.
  • UV initiators include, but are not limited to: phosphine oxides, benzophenone and substituted benzophenones, acetophenone and substituted acetophenones, benzoin and its alkyl ethers and combinations thereof.
  • compositions of the present invention may be used, for example, to seal or bond substrates, such as, but not limited to, gaskets.
  • substrates such as, but not limited to, gaskets.
  • Ihe composition maybe applied to one of the substrates which will form part of the gasket, cured or at least partially cured, and then joined to a second substrate to form the gasket assembly.
  • gasketing applications include, for example, form-in-place gaskets.
  • Coatings, adhesive joints and potting compositions may also be made from the inventive compositions.
  • the compositions may be applied to a substrate and subjected to curing conditions.
  • H 2 C CHCOCH 2 CH 2 O- 2,4-TDI — HMTD — 2,4-TDI — pTHF— 2,4-TDI — HMTD — 2,4-TD
  • —OCH 2 CH 2 OCCH CH 2
  • Reaction scheme 2 is not limited to (meth)acrylate functionality and may be used to prepare vinyl ether terminated block copolymers as well as block copolymers having both (meth)acrylate and vinyl ether functionality.
  • HMTD and pTHF variables used in the schemes above encompass radicals of these components.
  • the reaction mixture was titrated to determine the quantity of hydroxyethyl methacrylate to be added. Then the calculated amount of hydroxyethyl methacrylate (' ⁇ EMA”) and bismuth octoate were added in the amounts provided in Table 1. The temperature was maintained at 75°C while stirring for three hours, which yielded 411.7g of the methacrylate capped polyurethane block copolymer ("C" Stage Product) in the vinyl ether diluent.
  • ' ⁇ EMA hydroxyethyl methacrylate
  • C methacrylate capped polyurethane block copolymer
  • the reaction mixture was titrated to determine the quantity of poly(tetramethylene ether) diol (pTHF) to be added. Then the calculated amount of poly(tetramethylene ether) diol and dibutyl tin dilaurate (DBTDL (H)) were added in the amounts provided in Table 5 and the reaction mixture was stirred for three hours. This yielded 452.9g of the acrylate capped polyurethane block copolymer ("C" Stage Product) in the 2-(2'-vinyloxyethoxy)ethyl acrylate diluent. This block copolymer contains 0.05 weight % isocyanate, as was determined by infrared spectroscopy.
  • a trifunctional block copolymer is prepared in accordance with the following. To a 5L reaction flask fitted with a mechanical stirrer is added 196.3 g (1 mole; 2 equivalents OH) of HMTD, 348.4 g (2 moles; 4 equivalents NCO) of 2,4-TDI and 700 g of reactive diluent FX- VEEA. The mixture is heated at 70°C until the isocyanate levels become constant at about half of the original value ( ⁇ 3 hours).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Macromonomer-Based Addition Polymer (AREA)

Abstract

La présente invention se rapporte à des résines séquencées à terminaison acrylate ou éther de vinyle, aux compositions dans lesquelles elles sont incluses et à leurs procédés de préparation. En particulier, les compositions de la présente invention peuvent contenir une résine séquencée à terminaison acrylate ou éther de vinyle telle qu'un copolymère séquencé de polyuréthane, un diluant réactif ayant une fonctionnalité de (méth)acrylate et d'éther de vinyle ou d'éther 1-alkénylique et un initiateur de durcissement. Les compositions peuvent être exposées à une source d'énergie, par exemple une irradiation laser, qui assure un durcissement superficiel hors poisse.
PCT/US2005/040856 2005-02-01 2005-11-10 Resines sequencees a acrylate/ether de vinyle, compositions et procedes de fabrication WO2006083343A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US11/814,584 US20080139687A1 (en) 2005-11-10 2005-11-10 Vinyl Ether/Acrylate Block Resins, Compositions and Methods of Making Same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US64889805P 2005-02-01 2005-02-01
US60/648,898 2005-02-01

Publications (1)

Publication Number Publication Date
WO2006083343A1 true WO2006083343A1 (fr) 2006-08-10

Family

ID=36777549

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/040856 WO2006083343A1 (fr) 2005-02-01 2005-11-10 Resines sequencees a acrylate/ether de vinyle, compositions et procedes de fabrication

Country Status (1)

Country Link
WO (1) WO2006083343A1 (fr)

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100104776A1 (en) * 2007-04-16 2010-04-29 Kim Hee-Jung Optical film and liquid crystal display comprising the same
WO2010090715A1 (fr) * 2009-02-06 2010-08-12 Eastman Chemical Company Compositions de revêtement en polyester thermodurcissable contenant du tétraméthyl-cyclobutanediol
US8168721B2 (en) 2009-02-06 2012-05-01 Eastman Chemical Company Coating compositions containing tetramethyl cyclobutanediol
CN102532930A (zh) * 2011-12-31 2012-07-04 株洲时代电气绝缘有限责任公司 一种改性乙烯基树脂及其制备方法
US8324316B2 (en) 2009-02-06 2012-12-04 Eastman Chemical Company Unsaturated polyester resin compositions containing 2,2,2,4-tetramethyl-1,3-cyclobutanediol and articles made therefrom
JPWO2011021363A1 (ja) * 2009-08-19 2013-01-17 株式会社ブリヂストン 光硬化性組成物
CN104292141A (zh) * 2014-08-18 2015-01-21 华南理工大学 含硫醚和氨基甲酸酯基团的大分子受阻酚抗氧剂及其制备方法与应用
US9029461B2 (en) 2009-02-06 2015-05-12 Eastman Chemical Company Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol
US9029460B2 (en) 2009-02-06 2015-05-12 Stacey James Marsh Coating compositions containing acrylic and aliphatic polyester blends
US9487619B2 (en) 2014-10-27 2016-11-08 Eastman Chemical Company Carboxyl functional curable polyesters containing tetra-alkyl cyclobutanediol
US9598602B2 (en) 2014-11-13 2017-03-21 Eastman Chemical Company Thermosetting compositions based on phenolic resins and curable poleyester resins made with diketene or beta-ketoacetate containing compounds
US9650539B2 (en) 2014-10-27 2017-05-16 Eastman Chemical Company Thermosetting compositions based on unsaturated polyesters and phenolic resins
US20170369737A1 (en) * 2016-06-28 2017-12-28 Prc-Desoto International, Inc. Urethane/urea-containing bis(alkenyl) ethers, prepolymers prepared using urethane/urea-containing bis(alkenyl) ethers, and uses thereof
US9988553B2 (en) 2016-02-22 2018-06-05 Eastman Chemical Company Thermosetting coating compositions
US10011737B2 (en) 2016-03-23 2018-07-03 Eastman Chemical Company Curable polyester polyols and their use in thermosetting soft feel coating formulations
CN109661412A (zh) * 2016-08-08 2019-04-19 Prc-迪索托国际公司 可光化辐射固化的含氨基甲酸酯/脲的航天涂料和密封剂
CN110643273A (zh) * 2019-08-14 2020-01-03 萍乡高恒材料科技有限公司 一种高性能水性聚氨酯组合物及制法
US10526444B2 (en) 2015-09-25 2020-01-07 Eastman Chemical Company Polymers containing cyclobutanediol and 2,2-bis(hydroxymethyl)alkylcarboxylic acid
US10676565B2 (en) 2015-05-19 2020-06-09 Eastman Chemical Company Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol
CN111601783A (zh) * 2017-11-01 2020-08-28 艾弗里斯国际私人有限公司 包衣农业化学品组合物
US11098222B2 (en) 2018-07-03 2021-08-24 Prc-Desoto International, Inc. Sprayable polythioether coatings and sealants

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US4309526A (en) * 1975-03-12 1982-01-05 Loctite Corporation Unsaturated curable poly(alkylene)ether polyol-based resins having improved properties
US4587313A (en) * 1984-11-20 1986-05-06 Hitachi Chemical Company, Ltd. Radiation curable pressure-sensitive adhesive composition
US5139872A (en) * 1990-08-29 1992-08-18 Allied-Signal Inc. Vinyl ether based optical fiber coatings
WO2003082945A1 (fr) * 2002-04-03 2003-10-09 Kyowa Hakko Cmemical Co., Ltd. Resine de polyalcenyle ether
US20030199655A1 (en) * 2002-04-19 2003-10-23 Nippon Shokubai Co., Ltd. Reactive diluent and curable resin composition

Patent Citations (5)

* Cited by examiner, † Cited by third party
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US4309526A (en) * 1975-03-12 1982-01-05 Loctite Corporation Unsaturated curable poly(alkylene)ether polyol-based resins having improved properties
US4587313A (en) * 1984-11-20 1986-05-06 Hitachi Chemical Company, Ltd. Radiation curable pressure-sensitive adhesive composition
US5139872A (en) * 1990-08-29 1992-08-18 Allied-Signal Inc. Vinyl ether based optical fiber coatings
WO2003082945A1 (fr) * 2002-04-03 2003-10-09 Kyowa Hakko Cmemical Co., Ltd. Resine de polyalcenyle ether
US20030199655A1 (en) * 2002-04-19 2003-10-23 Nippon Shokubai Co., Ltd. Reactive diluent and curable resin composition

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100104776A1 (en) * 2007-04-16 2010-04-29 Kim Hee-Jung Optical film and liquid crystal display comprising the same
US8519055B2 (en) 2009-02-06 2013-08-27 Eastman Chemical Company Thermosetting polyester coating compositions containing tetramethyl cyclobutanediol
US9029461B2 (en) 2009-02-06 2015-05-12 Eastman Chemical Company Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol
US8163850B2 (en) 2009-02-06 2012-04-24 Eastman Chemical Company Thermosetting polyester coating compositions containing tetramethyl cyclobutanediol
US8168721B2 (en) 2009-02-06 2012-05-01 Eastman Chemical Company Coating compositions containing tetramethyl cyclobutanediol
US8524834B2 (en) 2009-02-06 2013-09-03 Eastman Chemical Company Coating compositions containing tetramethyl cyclobutanediol
US8324316B2 (en) 2009-02-06 2012-12-04 Eastman Chemical Company Unsaturated polyester resin compositions containing 2,2,2,4-tetramethyl-1,3-cyclobutanediol and articles made therefrom
CN102307961A (zh) * 2009-02-06 2012-01-04 伊士曼化工公司 含有四甲基环丁二醇的热固性聚酯涂料组合物
WO2010090715A1 (fr) * 2009-02-06 2010-08-12 Eastman Chemical Company Compositions de revêtement en polyester thermodurcissable contenant du tétraméthyl-cyclobutanediol
US9029460B2 (en) 2009-02-06 2015-05-12 Stacey James Marsh Coating compositions containing acrylic and aliphatic polyester blends
JP5836123B2 (ja) * 2009-08-19 2015-12-24 株式会社ブリヂストン 光硬化性組成物
JPWO2011021363A1 (ja) * 2009-08-19 2013-01-17 株式会社ブリヂストン 光硬化性組成物
CN102532930A (zh) * 2011-12-31 2012-07-04 株洲时代电气绝缘有限责任公司 一种改性乙烯基树脂及其制备方法
CN104292141A (zh) * 2014-08-18 2015-01-21 华南理工大学 含硫醚和氨基甲酸酯基团的大分子受阻酚抗氧剂及其制备方法与应用
CN104292141B (zh) * 2014-08-18 2016-03-02 华南理工大学 含硫醚和氨基甲酸酯基团的大分子受阻酚抗氧剂及其制备方法与应用
US9650539B2 (en) 2014-10-27 2017-05-16 Eastman Chemical Company Thermosetting compositions based on unsaturated polyesters and phenolic resins
US9487619B2 (en) 2014-10-27 2016-11-08 Eastman Chemical Company Carboxyl functional curable polyesters containing tetra-alkyl cyclobutanediol
US9598602B2 (en) 2014-11-13 2017-03-21 Eastman Chemical Company Thermosetting compositions based on phenolic resins and curable poleyester resins made with diketene or beta-ketoacetate containing compounds
US10676565B2 (en) 2015-05-19 2020-06-09 Eastman Chemical Company Aliphatic polyester coating compositions containing tetramethyl cyclobutanediol
US10526444B2 (en) 2015-09-25 2020-01-07 Eastman Chemical Company Polymers containing cyclobutanediol and 2,2-bis(hydroxymethyl)alkylcarboxylic acid
US9988553B2 (en) 2016-02-22 2018-06-05 Eastman Chemical Company Thermosetting coating compositions
US10011737B2 (en) 2016-03-23 2018-07-03 Eastman Chemical Company Curable polyester polyols and their use in thermosetting soft feel coating formulations
CN109415512A (zh) * 2016-06-28 2019-03-01 Prc-迪索托国际公司 含氨基甲酸酯/脲的双(烯基)醚，使用含氨基甲酸酯/脲的双(烯基)醚制备的预聚物，及其用途
US10370561B2 (en) 2016-06-28 2019-08-06 Prc-Desoto International, Inc. Urethane/urea-containing bis(alkenyl) ethers, prepolymers prepared using urethane/urea-containing bis(alkenyl) ethers, and uses thereof
US20170369737A1 (en) * 2016-06-28 2017-12-28 Prc-Desoto International, Inc. Urethane/urea-containing bis(alkenyl) ethers, prepolymers prepared using urethane/urea-containing bis(alkenyl) ethers, and uses thereof
WO2018005633A1 (fr) * 2016-06-28 2018-01-04 Prc-Desoto International, Inc. Bis(alcényl)éthers contenant de l'uréthane/urée, prépolymères préparés au moyen des bis(alcényl)éthers contenant de l'uréthane/urée, et leurs utilisations
CN109661412A (zh) * 2016-08-08 2019-04-19 Prc-迪索托国际公司 可光化辐射固化的含氨基甲酸酯/脲的航天涂料和密封剂
CN109661412B (zh) * 2016-08-08 2021-06-08 Prc-迪索托国际公司 可光化辐射固化的含氨基甲酸酯/脲的航天涂料和密封剂
US11898054B2 (en) 2016-08-08 2024-02-13 Prc-Desoto International, Inc. Actinic radiation-curable urethane/urea-containing aerospace coatings and sealants
CN111601783A (zh) * 2017-11-01 2020-08-28 艾弗里斯国际私人有限公司 包衣农业化学品组合物
CN111601783B (zh) * 2017-11-01 2023-09-05 艾弗里斯国际私人有限公司 包衣农业化学品组合物
US11098222B2 (en) 2018-07-03 2021-08-24 Prc-Desoto International, Inc. Sprayable polythioether coatings and sealants
CN110643273A (zh) * 2019-08-14 2020-01-03 萍乡高恒材料科技有限公司 一种高性能水性聚氨酯组合物及制法

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