CN101096472A - Adhesive property promoter for radiation curing material - Google Patents

Adhesive property promoter for radiation curing material Download PDF

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Publication number
CN101096472A
CN101096472A CNA2006100281176A CN200610028117A CN101096472A CN 101096472 A CN101096472 A CN 101096472A CN A2006100281176 A CNA2006100281176 A CN A2006100281176A CN 200610028117 A CN200610028117 A CN 200610028117A CN 101096472 A CN101096472 A CN 101096472A
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CN
China
Prior art keywords
adhesive property
radiation
property promoter
curing material
radiation curing
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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.)
Pending
Application number
CNA2006100281176A
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Chinese (zh)
Inventor
林际兵
张金山
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FEIKAI PHOTOELECTRIC MATERIAL Co Ltd SHANGHAI
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FEIKAI PHOTOELECTRIC MATERIAL Co Ltd SHANGHAI
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Filing date
Publication date
Application filed by FEIKAI PHOTOELECTRIC MATERIAL Co Ltd SHANGHAI filed Critical FEIKAI PHOTOELECTRIC MATERIAL Co Ltd SHANGHAI
Priority to CNA2006100281176A priority Critical patent/CN101096472A/en
Priority to PCT/CN2006/003385 priority patent/WO2008003191A1/en
Publication of CN101096472A publication Critical patent/CN101096472A/en
Pending legal-status Critical Current

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    • 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

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  • 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

The invention discloses a new adhesive property accelerant in the radiating solidified paint and adhesive, which is characterized by the following: reacting alkoxy silane compound with isocyanate and acrylate with hydroxy or amino or methacrylate ester monomer catalyzed by tin dibutyl dilaurate under 40-60 deg. c; making adhesive promotion function at one end of accelerant and (methyl)acrylate with polymerization activity at the other end; improving the adhesive property with substrate in the paint, ink and adhesive.

Description

Adhesive property promoter for radiation curing material
Technical field
The present invention relates to a kind of adhesive property promoter for radiation curing material, can be applicable to increases the adhesiveproperties that it solidifies back and ground in coating, printing ink and the tackiness agent.Especially can be applied in and improve the adhesiveproperties that it solidifies back and ground in the coating of radiation-curable or the tackiness agent.
Background technology
Within in the past 20 years, radiation adjustable curing material (wherein comprising ultraviolet curable material and electron beam curable material) has obtained development at full speed.Because radiation adjustable curing material has the production efficiency height, energy consumption is hanged down advantages such as reaching non-environmental-pollution, obtained at aspects such as coating, printing ink, tackiness agent very using widely.Radiation curing material generally is made up of four big components: oligopolymer, reactive monomer, light trigger and other auxiliary agents.Radiation curing material generally be coated on the ground earlier after, (UV-light or electron beam) solidifies under source of radiation then.Radiation curing material is after curing, and it also has bigger difference because of system different with the bonding force of ground.Adhesive property promoter is exactly that the most common can be used to increases after the material cured auxiliary agent with the adhesiveproperties of ground.The most common adhesive property promoter is an organoalkoxysilane.
The organoalkoxysilane adhesive property promoter does not generally have polymerization activity---can not participate in the polyreaction that takes place between the monomer, oligopolymer in the solidification process, so its consumption in prescription is subjected to suitable restriction.Industrial unique organoalkoxysilane adhesive property promoter with polymerization activity commonly used is the methacryloyl propyl trimethoxy silicane.But wherein generally contain a certain amount of starting material---propenyl methyl methacrylate that is used for synthesizing this compound, propenyl methyl methacrylate volatility is higher, smell is also bigger, its suitability is restricted (Waldman, Silane Coupling Agents Improving Performance, Modern Paints and Coatings, Feb., 1996).
The International Patent Application WO 96/12749 that on 05 02nd, 1996 World Intellectual Property Organization announces discloses and has a kind ofly contained the oligopolymer of organoalkoxysilane and contain this oligopolymer optical fiber coatings.The molecular weight of this one type of silane oligopolymer generally higher (500-11000), and the content of this quasi-oligomer in prescription generally also needs higher (5-99%), and this quasi-oligomer generally is the material of polyurethanes.
In addition, U.S. Pat 6391463B1 discloses a kind of novel organoalkoxysilane monomer with polymerization activity, and this monomer is to make by hydrosilation reaction.
Summary of the invention
Above-mentioned deficiency at prior art, technical problem to be solved of the present invention provide two kinds easy, the novel adhesive property promoter of easy suitability for industrialized production, these novel adhesive property promoters have polymerization activity, can widespread use in the coating of radiation-curable, printing ink, tackiness agent, and its consumption also can be bigger.
In order to solve the problems of the technologies described above, first kind of adhesive property promoter for radiation curing material that the present invention proposes, by the alkoxysilane compound containing trialkylsilyl group in molecular structure that contains isocyanic ester and hydroxyl or amino acrylate or methacrylate monomer under the catalysis of dibutyl tin laurate (DBTDL), form 40-60 ℃ of following rapid reaction, shown in reaction formula 2.
Figure A20061002811700041
Reaction formula 2
Second kind of adhesive property promoter for radiation curing material that the present invention proposes behind the acrylate or methacrylic ester and di-isocyanate reaction by hydroxyl or amino, forms with the organoalkoxysilane reaction that contains sulfydryl or amino, shown in reaction formula 3 again.
Figure A20061002811700051
Reaction formula 3
With respect to prior art, the above-mentioned two kinds of adhesive property promoter for radiation curing material of the present invention, because of it has polymerization activity simultaneously, thereby the consumption in coating, printing ink, tackiness agent can be unrestricted, especially at the coating of radiation-curable, the extensive application in printing ink and the tackiness agent can change after the material cured sticking power to ground significantly.
Embodiment
Below in conjunction with embodiment the present invention is described in further detail.
Embodiment 1
According to reaction formula 2, with 20.5g 3-isocyanic ester propyl trimethoxy silicane, 0.02g dibutyl tin laurate (DBTDL) adds in dry, the clean reactor, evenly stirs down, to wherein dripping 13.0g 2-hydroxyethyl methyl acrylate, after dropwising, be incubated 1 hour down at 40 ℃, through chemistry titration, isocyanate content＜0.1%, reaction finishes, and the gained light yellow liquid is radiation-curable adhesive property promoter A.
Embodiment 2
According to reaction formula 3, with 22.2g isophorone diisocyanate (IPDI), 0.03g dibutyl tin laurate (DBTDL), add in dry, the clean reactor, evenly stir down, to wherein dripping the 17.4g2-hydroxyethylmethacry,ate, after dropwising, 40 ℃ are incubated 1 hour down, then to wherein adding 19.6g3-sulfydryl propyl trimethoxy silicane, 80 ℃ were heated 12 hours down, and gained thickness colourless liquid is radiation-curable adhesive property promoter B, and its viscosity is: 34000cps (60 ℃).
Embodiment 3
According to reaction formula 3, with 22.2g isophorone diisocyanate (IPDI), 0.03g dibutyl tin laurate (DBTDL) adds in dry, the clean reactor, evenly stir down, to wherein dripping 2-hydroxyethylmethacry,ate 11.6g, after dropwising, 40 ℃ of following temperature controls 1 hour, then to wherein adding 22.1gN-ethyl-3-ammonia isobutyl-trimethyl-silicane alkane, and to add 14g isobornyl acrylate (IBOA) monomer be thinner.Stirred 1 hour down at 60 ℃, obtain very heavy-gravity yellow liquid, this is adhesive property promoter for radiation curing material C, and its viscosity is 8300cps (25 ℃).
Embodiment 4--radiation-curable tackiness agent
50% radiation-curable adhesive property promoter B
47% isobornyl acrylate (IBOA)
3%1-hydroxycyclohexylphenylketone (Irgacure 184)
Above component is sequentially added in the reactor, stirs two hours after-filtration down at 60C ° and can get the ultra-violet curing tackiness agent, it 25 ℃ of following viscosity is: 400cps.Above caking agent can be used to bonded metal, glass etc.It is very firm to bond.
Embodiment 5--ultraviolet curable printing ink
45% aromatic urethane acrylic acid oligomer (RMAT 650)
12% hexylene glycol diester acrylates (HDDA)
20% TriMethylolPropane(TMP) vinylformic acid, three esters (TMPTA)
15% white colorant (55% titanium dioxide is dispersed among the 45%TMPTA)
3%1-hydroxycyclohexylphenylketone (Irgacure 184)
1%2,4,6-pseudocuminol (Irganox 1010)
4% radiation-curable adhesive property promoter B
Above component is sequentially added in the reactor, stirs two hours after-filtration down at 60C ° and can get uv curing ink, it 25 ℃ of following viscosity is: 1720cps.This ultraviolet curable white ink has good adhesiveproperties to glass, metal and some plastic materials.The printing ink of other color also can similarly be prepared.

Claims (5)

1, a kind of adhesive property promoter for radiation curing material, it is characterized in that, this adhesive property promoter, is formed 40-60 ℃ of following rapid reaction under dibutyl tin laurate catalysis by the alkoxysilane compound containing trialkylsilyl group in molecular structure that contains isocyanic ester and hydroxyl or amino acrylate or methacrylate monomer.
2, a kind of adhesive property promoter for radiation curing material is characterized in that, behind the acrylate or methacrylic ester and di-isocyanate reaction of this adhesive property promoter by hydroxyl or amino, forms with the organoalkoxysilane reaction that contains sulfydryl or amino again.
3, a kind of coating material of radiation-curable is characterized in that, this coating material contains right and requires 1 and/or 2 described adhesive property promoter for radiation curing material, and content is 0.1-60%.
4, a kind of tackiness agent of radiation-curable is characterized in that, this tackiness agent contains right and requires 1 and/or 2 described adhesive property promoter for radiation curing material, and content is 0.1-99%.
5, a kind of printing ink of radiation-curable is characterized in that, this printing ink contains right and requires 1 and/or 2 described adhesive property promoter for radiation curing material, and content is 0.1-10%.
CNA2006100281176A 2006-06-26 2006-06-26 Adhesive property promoter for radiation curing material Pending CN101096472A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CNA2006100281176A CN101096472A (en) 2006-06-26 2006-06-26 Adhesive property promoter for radiation curing material
PCT/CN2006/003385 WO2008003191A1 (en) 2006-06-26 2006-12-13 Radiation curable adhesion promoter

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CN101921511A (en) * 2010-09-16 2010-12-22 珠海保税区天然宝杰数码科技材料有限公司 Ink composition for ink-jet printing
CN102140110A (en) * 2010-09-08 2011-08-03 上海飞凯光电材料股份有限公司 High-adhesive force radiation curable activated monomer and preparation method and use thereof
CN102167925A (en) * 2011-03-02 2011-08-31 中国科学院长春应用化学研究所 Adhesion promoter of optical fiber coating and preparation method thereof
CN103172830A (en) * 2013-02-25 2013-06-26 淮南联合大学 Method for modifying acrylic ester by using organic silicon
CN103443209A (en) * 2010-12-28 2013-12-11 阿克佐诺贝尔国际涂料股份有限公司 Radiation curable coating compositions for metal
CN106189878A (en) * 2014-12-17 2016-12-07 奇美实业股份有限公司 Peelable adhesive composition and peelable adhesive tape
CN109868107A (en) * 2017-12-01 2019-06-11 万华化学（宁波）有限公司 A kind of adhesive and its preparation method and application
CN112996867A (en) * 2018-11-20 2021-06-18 爱克发-格法特公司 Radiation curable inkjet inks for the manufacture of printed circuit boards
CN115340783A (en) * 2022-08-31 2022-11-15 武汉镱得飞光电技术有限公司 Optical fiber coating adhesion promoter and preparation method thereof
CN115785850A (en) * 2022-11-30 2023-03-14 成都硅宝科技股份有限公司 Tackifying promoter, preparation method and application thereof, waterproof bonding single-component polyurethane sealant, preparation method and application thereof

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JP5579072B2 (en) * 2008-10-15 2014-08-27 関西ペイント株式会社 Silsesquioxane compound having a polymerizable functional group
CN102482514B (en) 2009-08-31 2015-09-23 比克化学股份有限公司 Coating tackifier on different substrate materials surface
CN102516907B (en) * 2011-12-13 2013-06-19 烟台德邦科技有限公司 Preparation method of ultraviolet-curable organosilicone-modified pressure-sensitive adhesive
US11028214B2 (en) 2018-01-22 2021-06-08 Corning Incorporated Synthesis of oligomer for optical fiber coating
JP7193553B2 (en) * 2018-06-12 2022-12-20 ダウ シリコーンズ コーポレーション Aqueous hybrid pressure-sensitive adhesive composition and method for producing the same
CN110734713B (en) * 2019-11-27 2020-09-25 上海蒂姆新材料科技有限公司 Adhesion promoter for adhesive, synthesis method and application

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DE3737245A1 (en) * 1987-11-03 1989-05-18 Bayer Ag AQUEOUS SOLUTIONS OR DISPERSIONS OF POLYURETHANES, A METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS COATING AGENTS OR FOR THE PRODUCTION OF COATING AGENTS
DE19715427A1 (en) * 1997-04-14 1998-10-15 Bayer Ag Aqueous 2-component binders and their use
DE10103027A1 (en) * 2001-01-24 2002-07-25 Bayer Ag Adhesion promoter, e.g. for improving adhesion of silicon-based protective coatings to polymeric substrates, comprising two-component polyurethane binder based on alkoxysilane-modified polyisocyanate

Cited By (16)

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CN102140110A (en) * 2010-09-08 2011-08-03 上海飞凯光电材料股份有限公司 High-adhesive force radiation curable activated monomer and preparation method and use thereof
CN101921511B (en) * 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 Ink composition for ink-jet printing
CN101921511A (en) * 2010-09-16 2010-12-22 珠海保税区天然宝杰数码科技材料有限公司 Ink composition for ink-jet printing
US9856392B2 (en) 2010-12-28 2018-01-02 Akzo Nobel Coatings International B.V. Radiation curable coating compositions for metal
CN103443209A (en) * 2010-12-28 2013-12-11 阿克佐诺贝尔国际涂料股份有限公司 Radiation curable coating compositions for metal
CN103443209B (en) * 2010-12-28 2016-04-27 阿克佐诺贝尔国际涂料股份有限公司 For the radiation-curable coating composition of metal
CN102167925A (en) * 2011-03-02 2011-08-31 中国科学院长春应用化学研究所 Adhesion promoter of optical fiber coating and preparation method thereof
CN103172830A (en) * 2013-02-25 2013-06-26 淮南联合大学 Method for modifying acrylic ester by using organic silicon
CN106189878A (en) * 2014-12-17 2016-12-07 奇美实业股份有限公司 Peelable adhesive composition and peelable adhesive tape
CN106189878B (en) * 2014-12-17 2019-08-27 奇美实业股份有限公司 Peelable adhesive composition and peelable adhesive tape
CN109868107A (en) * 2017-12-01 2019-06-11 万华化学（宁波）有限公司 A kind of adhesive and its preparation method and application
CN109868107B (en) * 2017-12-01 2021-04-20 万华化学（宁波）有限公司 Adhesive and preparation method and application thereof
CN112996867A (en) * 2018-11-20 2021-06-18 爱克发-格法特公司 Radiation curable inkjet inks for the manufacture of printed circuit boards
CN115340783A (en) * 2022-08-31 2022-11-15 武汉镱得飞光电技术有限公司 Optical fiber coating adhesion promoter and preparation method thereof
CN115785850A (en) * 2022-11-30 2023-03-14 成都硅宝科技股份有限公司 Tackifying promoter, preparation method and application thereof, waterproof bonding single-component polyurethane sealant, preparation method and application thereof
CN115785850B (en) * 2022-11-30 2024-05-28 成都硅宝科技股份有限公司 Adhesion promoter, preparation method and application thereof, and waterproof adhesive single-component polyurethane sealant, and preparation method and application thereof

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