CN101096473A - 辐射固化材料粘接性能促进剂 - Google Patents

辐射固化材料粘接性能促进剂 Download PDF

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CN101096473A
CN101096473A CNA2006100281180A CN200610028118A CN101096473A CN 101096473 A CN101096473 A CN 101096473A CN A2006100281180 A CNA2006100281180 A CN A2006100281180A CN 200610028118 A CN200610028118 A CN 200610028118A CN 101096473 A CN101096473 A CN 101096473A
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林际兵
张金山
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FEIKAI PHOTOELECTRIC MATERIAL Co Ltd SHANGHAI
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Priority to PCT/CN2006/003384 priority patent/WO2008003190A1/en
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    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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    • C08F220/18Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1811C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
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    • C09DCOATING 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
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    • C09D11/10Printing inks based on artificial resins
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    • C09D4/00Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16

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Abstract

本发明涉及一种新型的粘接性能促进剂,尤其是一种可以在辐射可固化的涂料和胶粘剂中应用的粘接性能促进剂。该粘接性能促进剂由含巯基的烷氧基硅烷与含两个或两个以上的丙烯酸酯官能团或甲基丙烯酸酯官能团的单体在有机胺的催化下在温和的条件下快速反应完成,该粘接性能促进剂的分子一端含有粘接性能促进官能团,如烷氧基硅烷,另一端含具有聚合活性的(甲基)丙烯酸酯官能团。本发明应用在涂料、油墨和胶粘剂中增加其固化后与底材的粘接性能。

Description

辐射固化材料粘接性能促进剂
技术领域
本发明涉及一种辐射固化材料粘接性能促进剂,可应用在涂料、油墨和胶粘剂中增加其固化后与底材的粘接性能。尤其可以应用在辐射可固化的涂料或胶粘剂中提高其固化后与底材的粘接性能。
背景技术
在过去的20年之内,辐射可固化材料(其中包含紫外可固化材料及电子束可固化材料)得到了飞速的发展。因为辐射可固化材料具有生产效率高、能耗低及无环境污染等优点,在涂料、油墨、胶粘剂等方面得到了十分广泛的应用。辐射固化材料一般由四大组分组成:低聚物、活性单体、光引发剂及其他助剂。辐射固化材料一般是先涂覆在底材上之后,然后在辐射源下(紫外光或电子束)固化。辐射固化材料在固化后,其与底材的粘接力也因体系的不同而有较大的差别。粘接性能促进剂就是最为常见的可用来增加材料固化后与底材的粘接性能的助剂。最为常见的粘接性能促进剂是烷氧基硅烷。
烷氧基硅烷粘接性能促进剂一般不具有聚合活性——不能参与固化过程中的单体、低聚物之间发生的聚合反应,因此其在配方中的用量受到相当的限制。工业上唯一常用的具有聚合反应活性的烷氧基硅烷粘接性能促进剂是甲基丙烯酰基丙基三甲氧基硅烷。但其中一般含有一定量的用来合成该化合物的原材料——丙烯基甲基丙烯酸甲酯,丙烯基甲基丙烯酸甲酯挥发性较高,气味也较大,其适用性受到限制(Waldman,Silane Coupling Agents Improving Performance,Modern Paints and Coatings,Feb.,1996)。
1996年05月02日世界知识产权组织公布的国际专利申请WO96/12749公开了一种含烷氧基硅烷的低聚物及含此低聚物光纤涂料。这类硅烷低聚物的分子量一般较高(500-11000),而且该类低聚物在配方中的含量一般也需较高(5-99%),这一类低聚物一般是聚氨酯类的材料。
另外,美国专利US6391463B1公开了一种新型的具有聚合反应活性的烷氧基硅烷单体,该单体是通过硅氢化反应制得。
发明内容
针对现有技术的上述不足,本发明的所要解决的技术问题是提供一种简便,易工业化生产的新型的粘接性能促进剂,该新型的粘接性能促进剂具有聚合反应活性,可以在辐射可固化的涂料、油墨、胶粘剂中广泛应用,而且其用量也可以比较大。
为了解决上述技术问题,本发明提出的辐射固化材料粘接性能促进剂,由含巯基的烷氧基硅烷与含两个或两个以上的丙烯酸酯官能团或甲基丙烯酸酯官能团的单体在有机胺的催化下在温和的条件下快速反应完成(例如:温度65℃下,1小时内),如反应式1所示。
Figure A20061002811800041
反应式1
上述辐射固化材料粘接性能促进剂的一端为(甲基)丙烯酸酯,具有聚合反应活性,另一端的烷氧基硅烷基团具有粘接促进性能。
相对于现有技术,本发明的辐射固化材料粘接性能促进剂,因其同时具有聚合反应活性,因而在涂料、油墨、胶粘剂中的用量可以不受限制,尤其在辐射可固化的涂料,油墨及胶粘剂中的大量应用可以大幅度改变材料固化后对底材的附着力。
具体实施方式
下面结合实施例对本发明作进一步详细描述。
实施例1
根据反应式1,将19.6g 3-巯基丙基三甲氧基硅烷,22.6g己二醇丙烯酸二酯,0.1g二乙胺加入干净、干燥的反应釜内,在均匀搅拌的情况下,加热至65℃。根据气相色谱测定,1小时后巯基丙基三甲氧基硅烷已完全反应完毕,所得无色液体为辐射可固化粘接性能促进剂A。
实施例2--紫外可固化涂覆材料
50%芳香族聚氨酯丙烯酸低聚物(RMAT 650)
42%己二醇丙烯酸二酯(HDDA)
3%1-羟基环己基苯基酮(Irgacure 184)
1%2,4,6-三甲基苯酚
4%辐射可固化粘接性能促进剂A
将以上组分按顺序加入反应釜内,在60C°下搅拌两小时后过滤可得紫外固化涂料,其在25℃下粘度为:2100cps。此紫外可固化涂覆材料对玻璃、金属及一些塑料材料具有良好的粘接性能。
实施例3--紫外可固化油墨
45%芳香族聚氨酯丙烯酸低聚物(RMAT 650)
12%己二醇丙烯酸二酯(HDDA)
20%三羟甲基丙烷丙烯酸三酯(TMPTA)
15%白色色浆(55%二氧化钛分散在45%TMPTA中)
3%1-羟基环己基苯基酮(Irgacure 184)
1%2,4,6-三甲基苯酚(Irganox 1010)
4%辐射可固化粘接性能促进剂A
将以上组分按顺序加入反应釜内,在60C°下搅拌两小时后过滤可得紫外固化油墨,其在25℃下粘度为:1600cps。此紫外可固化白色油墨对玻璃、金属及一些塑料材料具有良好的粘接性能。其它颜色的油墨也可类似配制。
实施例4--辐射可固化胶粘剂
50%辐射可固化粘接性能促进剂A
47%丙烯酸异冰片酯(IBOA)
3%1-羟基环己基苯基酮(Irgacure 184)
将以上组分按顺序加入反应釜内,在60C°下搅拌两小时后过滤可得紫外固化胶粘剂,其在25℃下粘度为:400cps。以上粘接剂可用来粘接金属、玻璃等。粘结十分牢固。

Claims (4)

1、一种辐射固化材料粘接性能促进剂,其特征在于,该粘接性能促进剂由含巯基的烷氧基硅烷与含两个或两个以上的丙烯酸酯官能团或甲基丙烯酸酯官能团的单体在有机胺的催化下在温和的条件下快速反应完成。
2、一种辐射可固化的涂覆材料,其特征在于,该涂覆材料含权利要求1所述的辐射固化材料粘接性能促进剂,含量为0.1-60%。
3、一种辐射可固化的胶粘剂,其特征在于,该胶粘剂含权利要求1所述的辐射固化材料粘接性能促进剂,含量为0.1-99%。
4、一种辐射可固化的油墨,其特征在于,该油墨含权利要求1所述的辐射固化材料粘接性能促进剂,含量为0.1-10%。
CNA2006100281180A 2006-06-26 2006-06-26 辐射固化材料粘接性能促进剂 Pending CN101096473A (zh)

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Cited By (4)

* Cited by examiner, † Cited by third party
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CN102140109A (zh) * 2010-09-08 2011-08-03 上海飞凯光电材料股份有限公司 高附着力的辐射固化活性单体及其用途
CN112996867A (zh) * 2018-11-20 2021-06-18 爱克发-格法特公司 用于制造印刷电路板的可辐射固化的喷墨油墨
CN114616294A (zh) * 2019-11-07 2022-06-10 爱克发-格法特公司 用于制造印刷电路板的可辐射固化的喷墨油墨
KR20230081423A (ko) * 2021-11-30 2023-06-07 한국생산기술연구원 점착소재 및 이의 이용

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US11028214B2 (en) 2018-01-22 2021-06-08 Corning Incorporated Synthesis of oligomer for optical fiber coating

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US5318850A (en) * 1991-11-27 1994-06-07 General Electric Company UV curable abrasion-resistant coatings with improved weatherability
EP0985443B1 (de) * 1998-09-10 2010-10-27 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Semipermeable Membranen
JP4814412B2 (ja) * 2000-03-16 2011-11-16 関西ペイント株式会社 硬化組成物およびその被膜形成方法
US6703433B1 (en) * 2000-05-12 2004-03-09 Dow Corning Corporation Radiation curable compositions containing alkenyl ether functional polyisobutylenes

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CN102140109A (zh) * 2010-09-08 2011-08-03 上海飞凯光电材料股份有限公司 高附着力的辐射固化活性单体及其用途
CN112996867A (zh) * 2018-11-20 2021-06-18 爱克发-格法特公司 用于制造印刷电路板的可辐射固化的喷墨油墨
CN114616294A (zh) * 2019-11-07 2022-06-10 爱克发-格法特公司 用于制造印刷电路板的可辐射固化的喷墨油墨
KR20230081423A (ko) * 2021-11-30 2023-06-07 한국생산기술연구원 점착소재 및 이의 이용
KR102661529B1 (ko) 2021-11-30 2024-04-26 한국생산기술연구원 점착소재 및 이의 이용

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