CN102352165A - Monocomponent ultraviolet light self-crosslinking type acrylate copolymer coating, and synthetic method and application thereof - Google Patents

Monocomponent ultraviolet light self-crosslinking type acrylate copolymer coating, and synthetic method and application thereof Download PDF

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CN102352165A
CN102352165A CN2011102012870A CN201110201287A CN102352165A CN 102352165 A CN102352165 A CN 102352165A CN 2011102012870 A CN2011102012870 A CN 2011102012870A CN 201110201287 A CN201110201287 A CN 201110201287A CN 102352165 A CN102352165 A CN 102352165A
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acrylate copolymer
coating
monomer
copolymer coating
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CN102352165B (en
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虞明东
曾兆华
陈嘉
李付亚
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Shanghai Weikai Optoelectronic New Materials Co Ltd
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WEIKAI CHEMICAL-PRODUCT Co Ltd SHANGHAI
Shanghai Chengying New Material Co Ltd
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Abstract

The invention relates to a monocomponent ultraviolet light self-crosslinking type acrylate copolymer coating, and a synthetic method and application thereof. The coating comprises, by weight, 0.02 to 8 of ultraviolet light active monomers, 2 to 20 of photocrosslinking functional monomers, 15 to 40 of other monofunctional monomers, 0.04 to 0.8 of an initiator and 30 to 80 of a solvent. The coating is prepared by stirring the above-mentioned raw materials in a reaction vessel for a reflux reaction at a temperature of 75 to 90 DEG C for 5 to 8 hours so as to evenly mix the raw materials and cooling an obtained mixture. The coating is applied on a substrate of a product to be coated, and the substrate is put in an ultraviolet light curing apparatus for crosslinking by illumination after the solvent is completely volatilized. Compared to the prior art, the coating provided in the invention has the advantages of good temperature tolerance, no inclusion of micromolecular compounds, no generation of toxic byproducts, capability to adapt to different application requirements, stable performance, etc.

Description

Single component UV-light self-crosslinked acrylate copolymer coating and synthesis method and application
Technical field
The present invention relates to a kind of coating, especially relate to a kind of single component UV-light self-crosslinked acrylate copolymer coating and synthesis method and application.
Background technology
Yodo Sol GH 28 coating has excellent photostabilization and outdoor aging performance, and most of Yodo Sol GH 28s are low toxicities or nontoxic, can directly be used for food product pack and medical and hygiene article.Common Yodo Sol GH 28 does not have bridging property, and its coating is softening easily when being heated, and can dissolve when meeting the machine solvent to come off, thereby on using, be restricted.Existing terms of settlement is in Yodo Sol GH 28, to introduce crosslinked function, for example heat cross-linking (Chinese invention patent application CN101724173A; The open CN101338006A of Chinese invention patent), two component normal temperature crosslinked (Chinese invention patent CN100368485C).One Chinese patent application CN101935387 then proposes a kind of modification UV photocuring pure acrylic resin, utilizes the epoxy group(ing) in the Yodo Sol GH 28 on copolymer chain, to introduce acrylic double bond, makes coating curing thereby photopolymerization can take place this pair key.
The ultraviolet light irradiation curing technology has and advantage such as solidifies rapidly, the consolidation zone selectivity is strong and temperature is low, and extremely people pay close attention to.Need to add ultraviolet initiator and UV-light initiation auxiliary agent during traditional ultraviolet light irradiation is coating material solidified, mostly ultraviolet initiator is 2-hydroxy-2-methyl-1-phenyl-acetone, 1-hydroxyl-cyclohexyl benzophenone, UVNUL MS-40, benzoin methyl ether, Benzoin ethyl ether or st-yrax n-butyl ether etc.; UV-light causes auxiliary agent and is mostly triethylamine, diethylamine, trolamine or diethanolamine etc.Solidify the residual ultraviolet initiator in back easily to surface transport; Generate toxic by-products; Has stronger smell; And the easy flavescence of filming, big limitations the development space of UV-curing technology at some expensive goods (like food product pack, medical and hygiene article, cosmetic products and personal-care supplies).
Summary of the invention
The object of the invention be exactly provide in order to overcome the defective that above-mentioned prior art exists a kind of temperature tolerance good, do not contain micromolecular compound; Toxic by-products can be do not formed, single component UV-light self-crosslinked acrylate copolymer coating and the synthesis method and the application of different application requirement, stable performance can be adapted to.
The object of the invention can be realized through following technical scheme: a kind of single component UV-light self-crosslinked acrylate copolymer coating is characterized in that this coating comprises following component and weight part content:
UV-light reactive monomer 0.02~8;
Photo-crosslinking function monomer 2~20;
Other single functionality monomers 15~40;
Initiator 0.04~0.8;
Solvent 30~80.
Described coating comprises following component and weight part content:
UV-light reactive monomer 2~6;
Photo-crosslinking function monomer 8~16;
Other single functionality monomers 20~30;
Initiator 0.1~0.5;
Solvent 45~70.
Described coating comprises following component and weight part content:
UV-light reactive monomer 2~4;
Photo-crosslinking function monomer 10~12;
Other single functionality monomers 22~28;
Initiator 0.2~0.3;
Solvent 50~60.
Described UV-light reactive monomer is selected from the acrylic ester monomer that contains the UV-light active group or in the vinyl monomer one or more; Described photo-crosslinking function monomer is selected from one or more in acrylic ester monomer or the vinyl monomer; Described other single functionality monomers are selected from 3~8 kinds in acrylic ester monomer or the vinyl monomer.
Described UV-light reactive monomer is selected from one or more in 4-(2-hydroxyl-3-allyloxy-propoxy-) UVNUL MS-40,4-(2-hydroxyl-3-acryloxy-propoxy-) UVNUL MS-40,4-(2-hydroxy-3-methyl acryloxy-propoxy-) UVNUL MS-40,4-(2-acryloxy-ethyl) UVNUL MS-40,4-(2-methacryloxy-ethyl) UVNUL MS-40, the 4-acryloxy UVNUL MS-40; Described photo-crosslinking function monomer is selected from one or more in dimethylaminoethyl methacrylate, vinylformic acid-2-hydroxypropyl acrylate, methacrylic acid-2-hydroxypropyl acrylate, isobutyl acrylate, Propenoic acid, 2-methyl, isobutyl ester, isodecyl acrylate, isodecyl methacrylate, Isooctyl acrylate monomer or the Isooctyl methacrylate; Described other single functionality monomers are selected from vinylformic acid; Methacrylic acid; Vinylformic acid-2-hydroxyl ethyl ester; 2-hydroxyethyl methacrylate; Glycidyl acrylate; Glycidyl methacrylate; Methylene-succinic acid; Dibutyl maleate; Dioctyl maleate; Vinyl-acetic ester; Vinylbenzene; Acrylamide; Methacrylamide; Vinyl cyanide; Methyl acrylate; Methyl methacrylate; Ethyl propenoate; Jia Jibingxisuanyizhi; Bing Xisuandingzhi; Butyl methacrylate; In lauryl acrylate or the lauryl methacrylate(LMA) 3~8 kinds.
Described initiator is selected from benzoyl peroxide or Diisopropyl azodicarboxylate.
Described solvent is selected from one or more in ethanol, Virahol or the ethyl acetate.
A kind of preparation method of single component UV-light self-crosslinked acrylate copolymer coating; It is characterized in that; This method is that UV-light reactive monomer, photo-crosslinking function monomer, other single functionality monomers, initiator and solvent are dropped in the reaction kettle; Mix at 75 ℃~90 ℃ refluxing and stirring 5h~8h, promptly get product after the cooling.
A kind of application of single component UV-light self-crosslinked acrylate copolymer coating; It is characterized in that; Single component UV-light self-crosslinked acrylate copolymer coating is coated on the base material of product to be coated, volatilizes and in the ultraviolet light polymerization device, carry out that illumination is crosslinked to get final product behind the solvent.
The irradiation energy of described UV-light self-crosslinking is 500mJ, and through test, the degree of crosslinking of coating is 80% behind the ultraviolet light irradiation, and heat resistance improves 40 ℃.
The degree of crosslinking of ultraviolet light cross-linking coating is pressed the test of Suo Shi extraction process.
The heat resistance of coating is with the test of heat-sealing gradometer.
Compared with prior art, the mode with covalent linkage in polymerization process of the UV-light active group in the coating of the present invention combines with polymer chain, has avoided adding ultraviolet initiator and UV-light and has caused micromolecular that auxiliary agent causes and separate out and move.After the coating drying, coating forms cross-linked network fast under uv light irradiation.Diphenyl ketone type UV-light active group in the coating and the reaction of the non-pair of of bonding photo-crosslinking functional group form covalent linkage and produce crosslinkedly, and product of the present invention has the following advantages:
(1) through the design to the composition and the molecular structure of coating, form cross-linked network fast through ultraviolet light irradiation, heat resistance is significantly improved; (2) do not contain micromolecular compound, can not form toxic by-products; (3) can obtain suitable degree of crosslinking through the consumption of regulating the UV-light reactive monomer, the consumption and the monomeric consumption of other single functionalities of photo-crosslinking function monomer, to adapt to the different application requirement; (4) because the stable performance in coating of UV-light active group, under the lucifuge condition not can with other group generation crosslinking reactions, just self-crosslinking can take place only under action of ultraviolet light, at room temperature lucifuge was stored 6 months, it is stable that performance still keeps.
Embodiment
Below in conjunction with specific embodiment the present invention is elaborated.
Embodiment 1
The single component UV-light self-crosslinked acrylate copolymer coating of present embodiment is synthetic for raw material by following component (weight part):
Figure BDA0000076625680000041
Concrete building-up process is: mix stirring to make in UV-light reactive monomer, photo-crosslinking function monomer, other single functionality monomers, initiator and the solvent input reaction kettle; Agitation condition is at 80 ℃ of backflow 6h, obtains single component UV-light self-crosslinked acrylate copolymer coating after the cooling.
Above-mentioned gained single component UV-light self-crosslinked acrylate copolymer coating is coated with on base material, volatilizes that in the ultraviolet light polymerization device, to carry out illumination behind the solvent crosslinked, and the irradiation energy of UV-light self-crosslinking is 500mJ.Through test, the degree of crosslinking of coating is 80% behind the ultraviolet light irradiation, and heat resistance improves 40 ℃.
Embodiment 2
The single component UV-light self-crosslinked acrylate copolymer coating of present embodiment is synthetic for raw material by following component (weight part):
Figure BDA0000076625680000042
Building-up process is identical with embodiment 1.Gained single component UV-light self-crosslinked acrylate copolymer coating is coated with on base material, volatilizes that in the ultraviolet light polymerization device, to carry out illumination behind the solvent crosslinked, and the irradiation energy of UV-light self-crosslinking is 500mJ.Through test, the degree of crosslinking of coating is 60% behind the ultraviolet light irradiation, and heat resistance improves 20 ℃.
Embodiment 3
The single component UV-light self-crosslinked acrylate copolymer coating of present embodiment is synthetic for raw material by following component (weight part):
Figure BDA0000076625680000051
Building-up process is identical with embodiment 1.Gained single component UV-light self-crosslinked acrylate copolymer coating is coated with on base material, volatilizes that in the ultraviolet light polymerization device, to carry out illumination behind the solvent crosslinked, and the irradiation energy of UV-light self-crosslinking is 500mJ.Through test, the degree of crosslinking of coating is 90% behind the ultraviolet light irradiation, and heat resistance improves 40 ℃.
Embodiment 4
The single component UV-light self-crosslinked acrylate copolymer coating of present embodiment is synthetic for raw material by following component (weight part):
Figure BDA0000076625680000052
Building-up process is identical with embodiment 1.Gained single component UV-light self-crosslinked acrylate copolymer coating is coated with on base material, volatilizes that in the ultraviolet light polymerization device, to carry out illumination behind the solvent crosslinked, and the irradiation energy of UV-light self-crosslinking is 500mJ.Through test, the degree of crosslinking of coating is 69% behind the ultraviolet light irradiation, and heat resistance improves 30 ℃.
Embodiment 5
The single component UV-light self-crosslinked acrylate copolymer coating of present embodiment is synthetic for raw material by following component (weight part):
Figure BDA0000076625680000061
Building-up process is identical with embodiment 1.Gained single component UV-light self-crosslinked acrylate copolymer coating is coated with on base material, volatilizes that in the ultraviolet light polymerization device, to carry out illumination behind the solvent crosslinked, and the irradiation energy of UV-light self-crosslinking is 500mJ.Through test, the degree of crosslinking of coating is 65% behind the ultraviolet light irradiation, and heat resistance improves 30 ℃.
Embodiment 6
The single component UV-light self-crosslinked acrylate copolymer coating of present embodiment is synthetic for raw material by following component (weight part):
Figure BDA0000076625680000062
Concrete building-up process is: mix stirring to make in UV-light reactive monomer, photo-crosslinking function monomer, other single functionality monomers, initiator and the solvent input reaction kettle; Agitation condition is at 75 ℃ of backflow 5h, obtains single component UV-light self-crosslinked acrylate copolymer coating after the cooling.
Above-mentioned gained single component UV-light self-crosslinked acrylate copolymer coating is coated with on base material, volatilizes that in the ultraviolet light polymerization device, to carry out illumination behind the solvent crosslinked, and the irradiation energy of UV-light self-crosslinking is 200mJ.Through test, the degree of crosslinking of coating is 80% behind the ultraviolet light irradiation, and heat resistance improves 40 ℃.
Embodiment 7
The single component UV-light self-crosslinked acrylate copolymer coating of present embodiment is synthetic for raw material by following component (weight part):
Figure BDA0000076625680000071
Concrete building-up process is: mix stirring to make in UV-light reactive monomer, photo-crosslinking function monomer, other single functionality monomers, initiator and the solvent input reaction kettle; Agitation condition is at 90 ℃ of backflow 8h, obtains single component UV-light self-crosslinked acrylate copolymer coating after the cooling.
Above-mentioned gained single component UV-light self-crosslinked acrylate copolymer coating is coated with on base material, volatilizes that in the ultraviolet light polymerization device, to carry out illumination behind the solvent crosslinked, and the irradiation energy of UV-light self-crosslinking is 2000mJ.Through test, the degree of crosslinking of coating is 80% behind the ultraviolet light irradiation, and heat resistance improves 40 ℃.
Embodiment 8
The single component UV-light self-crosslinked acrylate copolymer coating of present embodiment is synthetic for raw material by following component (weight part):
Figure BDA0000076625680000072
Concrete building-up process is: mix stirring to make in UV-light reactive monomer, photo-crosslinking function monomer, other single functionality monomers, initiator and the solvent input reaction kettle; Agitation condition is at 75~80 ℃ of 5~6h that reflux, and obtains single component UV-light self-crosslinked acrylate copolymer coating after the cooling.
Above-mentioned gained single component UV-light self-crosslinked acrylate copolymer coating is coated with on base material, volatilizes that in the ultraviolet light polymerization device, to carry out illumination behind the solvent crosslinked, and the irradiation energy of UV-light self-crosslinking is 500~600mJ.Through test, the degree of crosslinking of coating is 85% behind the ultraviolet light irradiation, and heat resistance improves 45 ℃.
Embodiment 9
The single component UV-light self-crosslinked acrylate copolymer coating of present embodiment is synthetic for raw material by following component (weight part):
Figure BDA0000076625680000081
Concrete building-up process is: mix stirring to make in UV-light reactive monomer, photo-crosslinking function monomer, other single functionality monomers, initiator and the solvent input reaction kettle; Agitation condition is at 85~90 ℃ of 7~8h that reflux, and obtains single component UV-light self-crosslinked acrylate copolymer coating after the cooling.
Above-mentioned gained single component UV-light self-crosslinked acrylate copolymer coating is coated with on base material, volatilizes that in the ultraviolet light polymerization device, to carry out illumination behind the solvent crosslinked, and the irradiation energy of UV-light self-crosslinking is 1000~1200mJ.Through test, the degree of crosslinking of coating is 90% behind the ultraviolet light irradiation, and heat resistance improves 50 ℃.

Claims (10)

1. single component UV-light self-crosslinked acrylate copolymer coating is characterized in that this coating comprises following component and weight part content:
UV-light reactive monomer 0.02~8;
Photo-crosslinking function monomer 2~20;
Other single functionality monomers 15~40;
Initiator 0.04~0.8;
Solvent 30~80.
2. a kind of single component UV-light self-crosslinked acrylate copolymer coating according to claim 1 is characterized in that described coating comprises following component and weight part content:
UV-light reactive monomer 2~6;
Photo-crosslinking function monomer 8~16;
Other single functionality monomers 20~30;
Initiator 0.1~0.5;
Solvent 45~70.
3. a kind of single component UV-light self-crosslinked acrylate copolymer coating according to claim 1 is characterized in that described coating comprises following component and weight part content:
UV-light reactive monomer 2~4;
Photo-crosslinking function monomer 10~12;
Other single functionality monomers 22~28;
Initiator 0.2~0.3;
Solvent 50~60.
4. according to each described a kind of single component UV-light self-crosslinked acrylate copolymer coating in the claim 1~3; It is characterized in that described UV-light reactive monomer is selected from the acrylic ester monomer that contains the UV-light active group or in the vinyl monomer one or more; Described photo-crosslinking function monomer is selected from one or more in acrylic ester monomer or the vinyl monomer; Described other single functionality monomers are selected from 3~8 kinds in acrylic ester monomer or the vinyl monomer.
5. according to each described a kind of single component UV-light self-crosslinked acrylate copolymer coating in the claim 4; It is characterized in that described UV-light reactive monomer is selected from one or more in 4-(2-hydroxyl-3-allyloxy-propoxy-) UVNUL MS-40,4-(2-hydroxyl-3-acryloxy-propoxy-) UVNUL MS-40,4-(2-hydroxy-3-methyl acryloxy-propoxy-) UVNUL MS-40,4-(2-acryloxy-ethyl) UVNUL MS-40,4-(2-methacryloxy-ethyl) UVNUL MS-40, the 4-acryloxy UVNUL MS-40; Described photo-crosslinking function monomer is selected from one or more in dimethylaminoethyl methacrylate, vinylformic acid-2-hydroxypropyl acrylate, methacrylic acid-2-hydroxypropyl acrylate, isobutyl acrylate, Propenoic acid, 2-methyl, isobutyl ester, isodecyl acrylate, isodecyl methacrylate, Isooctyl acrylate monomer or the Isooctyl methacrylate; Described other single functionality monomers are selected from vinylformic acid; Methacrylic acid; Vinylformic acid-2-hydroxyl ethyl ester; 2-hydroxyethyl methacrylate; Glycidyl acrylate; Glycidyl methacrylate; Methylene-succinic acid; Dibutyl maleate; Dioctyl maleate; Vinyl-acetic ester; Vinylbenzene; Acrylamide; Methacrylamide; Vinyl cyanide; Methyl acrylate; Methyl methacrylate; Ethyl propenoate; Jia Jibingxisuanyizhi; Bing Xisuandingzhi; Butyl methacrylate; In lauryl acrylate or the lauryl methacrylate(LMA) 3~8 kinds.
6. according to each described a kind of single component UV-light self-crosslinked acrylate copolymer coating in the claim 1~3, it is characterized in that described initiator is selected from benzoyl peroxide or Diisopropyl azodicarboxylate.
7. according to each described a kind of single component UV-light self-crosslinked acrylate copolymer coating in the claim 1~3, it is characterized in that described solvent is selected from one or more in ethanol, Virahol or the ethyl acetate.
8. the preparation method of a single component UV-light self-crosslinked acrylate copolymer coating as claimed in claim 1; It is characterized in that; This method is that UV-light reactive monomer, photo-crosslinking function monomer, other single functionality monomers, initiator and solvent are dropped in the reaction kettle; Mix at 75 ℃~90 ℃ refluxing and stirring 5h~8h, promptly get product after the cooling.
9. the application of a single component UV-light self-crosslinked acrylate copolymer coating as claimed in claim 1; It is characterized in that; Single component UV-light self-crosslinked acrylate copolymer coating is coated on the base material of product to be coated, volatilizes and in the ultraviolet light polymerization device, carry out that illumination is crosslinked to get final product behind the solvent.
10. the application of single component UV-light self-crosslinked acrylate copolymer coating according to claim 9; It is characterized in that the irradiation energy of described UV-light self-crosslinking is 500mJ, through test; The degree of crosslinking of coating is 80% behind the ultraviolet light irradiation, and heat resistance improves 40 ℃.
CN 201110201287 2011-07-18 2011-07-18 Monocomponent ultraviolet light self-crosslinking type acrylate copolymer coating, and synthetic method and application thereof Expired - Fee Related CN102352165B (en)

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CN103012665A (en) * 2012-12-26 2013-04-03 河北智生环保科技有限公司 Ultraviolet cross-linked organosilicone modified acrylate copolymer emulsion
CN103013268A (en) * 2012-12-26 2013-04-03 河北智生环保科技有限公司 Photo-crosslinking white board coating
CN103289009A (en) * 2013-05-15 2013-09-11 浙江吉利汽车研究院有限公司杭州分公司 Composition for preparing coating, coating and preparation method of coating
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CN103012665A (en) * 2012-12-26 2013-04-03 河北智生环保科技有限公司 Ultraviolet cross-linked organosilicone modified acrylate copolymer emulsion
CN103013268A (en) * 2012-12-26 2013-04-03 河北智生环保科技有限公司 Photo-crosslinking white board coating
CN103013268B (en) * 2012-12-26 2015-05-13 河北智生环保科技有限公司 Photo-crosslinking white board coating
CN103012665B (en) * 2012-12-26 2015-07-15 河北智生环保科技有限公司 Ultraviolet cross-linked organosilicone modified acrylate copolymer emulsion
CN103289009A (en) * 2013-05-15 2013-09-11 浙江吉利汽车研究院有限公司杭州分公司 Composition for preparing coating, coating and preparation method of coating
CN104559505A (en) * 2014-12-23 2015-04-29 刘骏 Waterproof paint
CN104673143A (en) * 2015-02-05 2015-06-03 河北智生环保科技有限公司 Ionic cross-linked pressure-sensitive adhesive capable of being cross-linked by ultraviolet and preparation method thereof
CN105153775A (en) * 2015-09-14 2015-12-16 上海维凯光电新材料有限公司 Photo-curing aluminum-foil anticorrosive paint composition
CN108138020A (en) * 2015-09-30 2018-06-08 3M创新有限公司 Curable and cured adhesive composition
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CN109957072A (en) * 2017-12-25 2019-07-02 万华化学(宁波)有限公司 A kind of elastic emulsion and its preparation method and application with high density surface UV crosslinking effect
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CN109233664A (en) * 2018-06-12 2019-01-18 哈尔滨工业大学无锡新材料研究院 A kind of UV curing type adhesive, preparation method and application
CN111574867B (en) * 2020-06-05 2021-03-12 中国科学院兰州化学物理研究所 Composite antifogging coating and application thereof, composite antifogging coating and preparation method and application thereof
CN116333672A (en) * 2023-03-13 2023-06-27 东莞市德聚胶接技术有限公司 UV (ultraviolet) binder suitable for camera module and preparation method thereof
CN116333672B (en) * 2023-03-13 2023-11-17 广东德聚技术股份有限公司 UV (ultraviolet) binder suitable for camera module and preparation method thereof

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