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WO2008003191A1 - Promoteur d'adhésion durcissant sous rayonnement - Google Patents

Promoteur d'adhésion durcissant sous rayonnement Download PDF

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Publication number
WO2008003191A1
WO2008003191A1 PCT/CN2006/003385 CN2006003385W WO2008003191A1 WO 2008003191 A1 WO2008003191 A1 WO 2008003191A1 CN 2006003385 W CN2006003385 W CN 2006003385W WO 2008003191 A1 WO2008003191 A1 WO 2008003191A1
Authority
WO
WIPO (PCT)
Prior art keywords
radiation curable
adhesion promoter
adhesion
acrylate
amino groups
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/CN2006/003385
Other languages
English (en)
Inventor
Jibing Lin
Jinshan Zhang
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.)
SHANGHAI PHICHEM Corp
Original Assignee
SHANGHAI PHICHEM Corp
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 SHANGHAI PHICHEM Corp filed Critical SHANGHAI PHICHEM Corp
Publication of WO2008003191A1 publication Critical patent/WO2008003191A1/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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8083—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen
    • C08G18/809—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with compounds containing at least one heteroatom other than oxygen or nitrogen containing silicon
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/81—Unsaturated isocyanates or isothiocyanates
    • C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
    • C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
    • C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
    • C08G18/8175—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with esters of acrylic or alkylacrylic 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • 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

  • This invention relates to a new type of radiation curable adhesion promoters, which can be applied to coatings, inks and adhesives to improve adhesion between cured materials and substrates. In particular they can be applied to radiation curable coatings and adhesives to promote adhesion between cured materials and substrates.
  • Radiation curable materials have been developed rapidly in the past 20 years. They have been widely used in coatings, inks and adhesives etc since they provide high productivity, low energy consumption and zero environment pollution. Radiation curable materials are in general composed of four ingredients: oligomers, reactive monomers, photoinitiators and additives. Radiation curable materials are commonly first coated on the substrates, and cured via radiation resources (ultraviolet light or electron beam). The adhesion between the substrates and the cured radiation curable materials varies considerably from system to system. Adhesion promoters are the most common additives that improve adhesion between cured materials and substrates. The most common adhesion promoters are alkoxysilanes.
  • Alkoxysilane adhesion promoters are generally polymerization inactive-can not participate in polymerization reactions of monomers and oligomers during curing. As a result, their levels in formulations are considerably limited.
  • the only commonly used polymerizable alkoxysilane adhesion promoter in industry is methacryloxypropyl trimethoxysilane. However it contains a certain level of starting material-allylmethacrylate, which is a volatile and odorous compound. Therefore its applicability is limited. See Waldman, Silane Coupling Agents Improving Performance, Modern Paints and Coatings, February, 1996.
  • WO 96/12749 discloses an oligomer containing alkoxysilanes and optical fiber coating containing the oligomer.
  • the silane oligomers are high in molecular weight (500-11000) and a high level of silane oligomers in the composition is needed (5-99%).
  • Such oligomers are typically polyurethane materials.
  • this invention provides a radiation curable adhesion promoter, which is obtained by fast reaction of alkoxysilane containing isocyanate, with acrylate or methacrylate monomers containing hydroxy or amino groups, at 40-60 0 C in the presence of dibutyltion dilaurate catalyst, as shown in Equation 1 :
  • the second radiation curable adhesion promoter put forward in this invention was obtained by reaction of acrylate or methacrylate containing hydroxy or amino groups, with diisocyanate, followed by reaction with alkoxysilane containing mercapto or amino groups, as shown in Equation 2.
  • above two radiation curable adhesion promoters in this invention due to polymerization activity, are unrestricted in quantity in their application to coatings, inks, and adhesives.
  • Particularly in radiation curable coatings, inks and adhesives use of above adhesion promoters in large quantities can greatly change adhesion power between cured materials and substrates.
  • Equation 1 20.5 g of 3-isocyanate propyl trimethylsilane and 0.02 g of dibutyltion dilaurate (DBTDL) were added into a dry and clean reactor, and 13.0 g of 2-hydroxyethyl methyl methacrylate was added dropwise under uniform stirring. After complete addition the mixture was kept at 40 0 C for an hour and the content of isocyanate was below 0.1% obtained by chemical titration. The resulting light yellow liquid was radiation curable adhesion promoter A.
  • DBTDL dibutyltion dilaurate
  • Equation 2 22.3 g of isophorone diisocyanate (IPDI) and 0.03 g of dibutyltion dilaurate (DBTDL) were added into a dry and clean reactor, and 17.4 g of 2-hydroxyethyl acrylate was added dropwise under uniform stirring. After complete addition the mixture was kept at 40 0 C for an hour and then 19.6 g of 3-mercapto propyl trimethoxysilane was added. After heating to 80 0 C for 12 hours the resulting viscous and colorless liquid was radiation curable adhesion promoter B. Its viscosity was 34000 cps (60 0 C).
  • IPDI isophorone diisocyanate
  • DBTDL dibutyltion dilaurate
  • HDDA 12% hexane-l,6-diol diacrylate
  • trimethlolpropane triacrylate (TMPTA)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

Cette invention concerne un nouveau type de promoteur d'adhésion qui peut s'utiliser dans des revêtements, des colles et des encres durcissant sous rayonnement. Ce promoteur d'adhésion s'obtient par une réaction rapide d'alcoxysilanes contenant un isocyanate avec des monomères d'acrylate ou de méthacrylate contenant des groupes hydroxyle ou amino, en présence d'un catalyseur au dibytyltine-dilaurate à une température de 40-60°C. Ce promoteur d'adhésion comporte des groupes fonctionnels promoteurs tels que des alcoxysilanes à une extrémité, et des groupes polymérisables de (méth)acrylate à l'autre extrémité. L'invention peut s'appliquer à des revêtements, des colles et des encres pour améliorer l'adhésion entre les matériaux durcis et les substrats.
PCT/CN2006/003385 2006-06-26 2006-12-13 Promoteur d'adhésion durcissant sous rayonnement Ceased WO2008003191A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN200610028117.6 2006-06-26
CNA2006100281176A CN101096472A (zh) 2006-06-26 2006-06-26 辐射固化材料粘接性能促进剂

Publications (1)

Publication Number Publication Date
WO2008003191A1 true WO2008003191A1 (fr) 2008-01-10

Family

ID=38894171

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2006/003385 Ceased WO2008003191A1 (fr) 2006-06-26 2006-12-13 Promoteur d'adhésion durcissant sous rayonnement

Country Status (2)

Country Link
CN (1) CN101096472A (fr)
WO (1) WO2008003191A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011023409A1 (fr) 2009-08-31 2011-03-03 Byk-Chemie Gmbh Promoteur d'adhérence pour revêtements de différentes surfaces de support
CN102516907A (zh) * 2011-12-13 2012-06-27 烟台德邦电子材料有限公司 一种可紫外光固化有机硅改性压敏胶的制备方法
US8784947B2 (en) * 2008-10-15 2014-07-22 Kansai Paint Co., Ltd. Silsesquioxane compound having polymerizable functional group
US9856392B2 (en) 2010-12-28 2018-01-02 Akzo Nobel Coatings International B.V. Radiation curable coating compositions for metal
CN110734713A (zh) * 2019-11-27 2020-01-31 上海蒂姆新材料科技有限公司 一种胶粘剂用粘接促进剂、合成方法及应用
US11028214B2 (en) 2018-01-22 2021-06-08 Corning Incorporated Synthesis of oligomer for optical fiber coating
JP2021531359A (ja) * 2018-06-12 2021-11-18 ダウ シリコーンズ コーポレーション 水性ハイブリッド感圧粘着剤組成物およびその製造方法

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102140110A (zh) * 2010-09-08 2011-08-03 上海飞凯光电材料股份有限公司 高附着力辐射固化活性单体及其制备方法和用途
CN101921511B (zh) * 2010-09-16 2012-04-25 珠海保税区天然宝杰数码科技材料有限公司 喷墨打印用墨水组合物
CN102167925A (zh) * 2011-03-02 2011-08-31 中国科学院长春应用化学研究所 一种光纤涂料附着力促进剂及其制备方法
CN103172830A (zh) * 2013-02-25 2013-06-26 淮南联合大学 一种有机硅改性丙烯酸酯的方法
TWI527863B (zh) * 2014-12-17 2016-04-01 奇美實業股份有限公司 可剝膠組成物與可剝膠帶
CN109868107B (zh) * 2017-12-01 2021-04-20 万华化学（宁波）有限公司 一种粘合剂及其制备方法和应用
JP2022511422A (ja) * 2018-11-20 2022-01-31 アグフア－ゲヴエルト，ナームローゼ・フエンノートシヤツプ プリント回路基板を製造するための放射線硬化性インクジェットインク
CN115340783B (zh) * 2022-08-31 2023-07-04 武汉镱得飞光电技术有限公司 一种光纤涂料附着力促进剂及其制备方法
CN115785850B (zh) * 2022-11-30 2024-05-28 成都硅宝科技股份有限公司 一种增粘促进剂及其制备方法和应用以及耐水粘接单组分聚氨酯密封胶及其制备方法和应用

Citations (3)

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US5041494A (en) * 1987-11-03 1991-08-20 Bayer Aktiengesellschaft Aqueous solutions or dispersions of polyurethanes, a process for their preparation and their use in coating compositions
US5854338A (en) * 1997-04-14 1998-12-29 Bayer Aktiengesellschaft Aqueous two-component binders and their use in coating and sealing compositions
CN1487982A (zh) * 2001-01-24 2004-04-07 用作粘结促进剂的双组分聚氨酯粘合剂

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5041494A (en) * 1987-11-03 1991-08-20 Bayer Aktiengesellschaft Aqueous solutions or dispersions of polyurethanes, a process for their preparation and their use in coating compositions
US5854338A (en) * 1997-04-14 1998-12-29 Bayer Aktiengesellschaft Aqueous two-component binders and their use in coating and sealing compositions
CN1487982A (zh) * 2001-01-24 2004-04-07 用作粘结促进剂的双组分聚氨酯粘合剂

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8784947B2 (en) * 2008-10-15 2014-07-22 Kansai Paint Co., Ltd. Silsesquioxane compound having polymerizable functional group
WO2011023409A1 (fr) 2009-08-31 2011-03-03 Byk-Chemie Gmbh Promoteur d'adhérence pour revêtements de différentes surfaces de support
US8778458B2 (en) 2009-08-31 2014-07-15 Byk-Chemie Gmbh Adhesion promoter for coatings on different substrate surfaces
US9593246B2 (en) 2009-08-31 2017-03-14 Byk-Chemie Gmbh Object or an article whose surface is provided with a coating produced using and adhesion promoter
US9856392B2 (en) 2010-12-28 2018-01-02 Akzo Nobel Coatings International B.V. Radiation curable coating compositions for metal
CN102516907A (zh) * 2011-12-13 2012-06-27 烟台德邦电子材料有限公司 一种可紫外光固化有机硅改性压敏胶的制备方法
US11028214B2 (en) 2018-01-22 2021-06-08 Corning Incorporated Synthesis of oligomer for optical fiber coating
JP2021531359A (ja) * 2018-06-12 2021-11-18 ダウ シリコーンズ コーポレーション 水性ハイブリッド感圧粘着剤組成物およびその製造方法
JP7193553B2 (ja) 2018-06-12 2022-12-20 ダウ シリコーンズ コーポレーション 水性ハイブリッド感圧粘着剤組成物およびその製造方法
US12024658B2 (en) 2018-06-12 2024-07-02 Dow Silicones Corporation Water-based hybrid pressure sensitive adhesive composition and method of producing the same
CN110734713A (zh) * 2019-11-27 2020-01-31 上海蒂姆新材料科技有限公司 一种胶粘剂用粘接促进剂、合成方法及应用

Also Published As

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