CN103509162A - Epoxy-modified polyester acrylate and preparation method thereof - Google Patents
Epoxy-modified polyester acrylate and preparation method thereof Download PDFInfo
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- CN103509162A CN103509162A CN201210214969.XA CN201210214969A CN103509162A CN 103509162 A CN103509162 A CN 103509162A CN 201210214969 A CN201210214969 A CN 201210214969A CN 103509162 A CN103509162 A CN 103509162A
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Abstract
The invention discloses an epoxy-modified polyester acrylate and a preparation method thereof, and particularly relates to a polyester acrylate modified by an epoxy group. According to the epoxy-modified polyester acrylate, an acid value is smaller than or equal to 5mg KOH/g; the viscosity is 20000-30000 Mpa.s. Free radical polymerization can be quickly carried out by ultraviolet radiation in coexistence of a photoinitiator, so as to achieve cross-linking solidification. The modified polyester acrylate disclosed by the invention can be applied to preparation of a photocureable coating and photocureable ink, and is suitable for photocuring coating of plastics and papers. Extremely low curing shrinkage rate, and excellent adhesive force and flexibility are provided for an immobilizing membrane; the modified polyester acrylate is photocureable resin with a good prospect and excellent overall performance.
Description
Technical field
The present invention relates to polyester acrylate, be specifically related to a kind of epoxide modified polyester acrylate and preparation method thereof.
Background technology
It is most widely used a kind of curing technology in radiation curing that UV-light (UV) is solidified.Or heat curing coating dry with traditional natural compared, and it is high that ultraviolet-curing paint has capacity usage ratio, is suitable for heat-sensitive substrate material, pollutes feature little, that film forming speed is fast, film quality is high and serialization is produced.Along with the enhancing of people's environmental consciousness and the raising that coating property is required, coating material solidified one of the development trend that become of UV.Zhang Sainan etc. by two step synthesis ultraviolet light polymerization rosinyl polyester acrylate performed polymer for coating, laser curing velocity (thermosetting resin, 2009,24 (6): 22-25) of having improved polyester acrylate.Analogy Lan Ying etc. adopts Multistep feeding method, with oxalic acid, 1,4-butyleneglycol, tetramethylolmethane, dimethylol propionic acid and vinylformic acid are that raw material has synthesized photocuring polyester acrylate performed polymer, by regulating hydroxyl carboxylic than controlling oligopolymer sticking power, improve cured coating film cohesiveness.The preparation technology of existing polyester acrylate, preparation time is long, and curing speed is slow to a certain extent, poor adhesive force.Still needing and develop a kind of novel modified poly ester acrylate and preparation technology thereof in this area, improves curing speed and sticking power.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, a kind of ultraviolet cured epoxy modified poly ester acrylate is provided, curing speed is fast, viscosity is high, snappiness is good, and can shorten process cycle.
Another object of the present invention is to provide a kind of preparation method of epoxide modified polyester acrylate resin.
A first aspect of the present invention, provides a kind of modified poly ester acrylate, is epoxy group(ing) modified poly ester acrylate, has following one or more feature:
(a) acid number≤5mgKOH/g;
(b) viscosity is 20000 ~ 30000Mpa.s.
A second aspect of the present invention, provides the preparation method of the modified poly ester acrylate described in a kind of first aspect face, said method comprising the steps of:
1) diprotic acid of the epoxy resin of 40～60 weight parts and 10～30 weight parts is added in reactor, at 100 ~ 105 ℃, react 1 ~ 3h;
2) to the vinylformic acid that adds 20～40 weight parts in reactor, at 105～110 ℃, react 1 ~ 2h;
3) to step 2) add the catalyzer of 0.5～1 weight part in reacted product, then under nitrogen protection, add the promoter of 0.8～1.5 weight part, in temperature, be to react 1～2h at 110～112 ℃;
4) to the oil of mirbane that adds 0.1～0.5 weight part in the reacted product of step 3), in temperature, be to react 1～2h at 110～115 ℃, then add the acrylate monomer of 10 ~ 30 weight parts, stir, vacuumize, react 1 ~ 2h and obtain described modified poly ester acrylate.
According to the present invention, the molecular weight of the epoxy resin described in described step 1) is 500～1000, and described diprotic acid is Tetra hydro Phthalic anhydride.
According to the present invention, the molecular weight of epoxy resin described in described step 1) is preferably 600, and described epoxy resin is preferably bisphenol A type epoxy resin (E-51).
According to the present invention, the catalyzer described in described step 3) is triethylamine, and described promoter is 2,6 ditertiary butyl p cresol.
According to the present invention, the acrylate monomer described in described step 4) is tripropylene glycol diacrylate or Propylene glycol monoacrylate.
According to the present invention, the acrylate monomer described in described step 4) is Propylene glycol monoacrylate.
A third aspect of the present invention, provides a kind of ultraviolet-curing paint, and described ultraviolet-curing paint comprises the modified poly ester acrylate described in first aspect.
According to the present invention, described coating also comprises thinner, light trigger and flow agent.
According to the present invention, described coating comprises modified poly ester acrylate described in 10-50 weight part; Thinner described in 5-10 weight part; 0.1-10 weight part light trigger; 0.1-1 weight part flow agent.
Modified poly ester acrylate resin of the present invention can be used in preparation photo-cured coating, and light-curable ink, is suitable for plastic cement, the photocuring application of paper.For cured film provides extremely low cure shrinkage, excellent adhesive attraction and snappiness, be that a class has good prospect and the superior light-cured resin of over-all properties.
In should be understood that within the scope of the present invention, above-mentioned each technical characterictic of the present invention and can combining mutually between specifically described each technical characterictic in below (eg embodiment), thus form new or preferred technical scheme.As space is limited, at this, tire out and state no longer one by one.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment are only not used in and limit the scope of the invention for the present invention is described.The experimental technique of unreceipted actual conditions in the following example, conventionally according to normal condition or the condition of advising according to manufacturer.
Each raw material that preparation method of the present invention adopts is commercially available prod, epoxy resin as used in embodiment can adopt Guangzhou Hong Chang E-51 product, Tetra hydro Phthalic anhydride can adopt the 85-44-9 product of Nanjing Hong Cheng company, vinylformic acid can adopt the 15445-01 product of Beijing Orient petro-chemical corporation, and Propylene glycol monoacrylate can adopt the 25584-83-2 product of Beijing Orient chemical company.
Embodiment 1
The preparation of the epoxide modified polyester acrylate resin of ultraviolet light polymerization:
1) Tetra hydro Phthalic anhydride of the epoxy resin that is 600 by the molecular weight of 60 weight parts and 30 weight parts adds in reactor, at 100 ℃, reacts 3h;
2) to the vinylformic acid that adds 20 weight parts in reactor, at 105 ℃, react 2h;
3) to step 2) add the triethylamine of 0.5 weight part in reacted product, then under nitrogen protection, add the 2,6 ditertiary butyl p cresol of 0.8 weight part, in temperature, be to react 2h at 111 ℃;
4) to the oil of mirbane that adds 0.1 weight part in the reacted product of step 3), in temperature, be to react 2h at 110 ℃, then add the Propylene glycol monoacrylate reaction 1h of 10 weight parts, stir and vacuumize and obtain product.
Embodiment 2
The preparation of the epoxide modified polyester acrylate resin of ultraviolet light polymerization:
1) Tetra hydro Phthalic anhydride of the epoxy resin that is 600 by the molecular weight of 50 weight parts and 20 weight parts adds in reactor, at 105 ℃, reacts 2h;
2) to the vinylformic acid that adds 40 weight parts in reactor, at 108 ℃, react 1.5h;
3) to step 2) add the triethylamine of 0.7 weight part in reacted product, then under nitrogen protection, add the 2.6-ditertbutylparacresol of 1.2 weight parts, in temperature, be to react 1.5h at 112 ℃;
4) to the oil of mirbane that adds 0.5 weight part in the reacted product of step 3), in temperature, be to react 2h at 112 ℃, then add the Propylene glycol monoacrylate reaction 1h of 30 weight parts to stir and vacuumize and obtain product.
Embodiment 3
The preparation of the epoxide modified polyester acrylate resin of ultraviolet light polymerization:
1) Tetra hydro Phthalic anhydride of the epoxy resin that is 600 by the molecular weight of 40 weight parts and 10 weight parts adds in reactor, at 103 ℃, reacts 2.5h;
2) to the vinylformic acid that adds 20 weight parts in reactor, at 110 ℃, react 2h;
3) to step 2) add the triethylamine of 1 weight part in reacted product, then under nitrogen protection, add the 2,6 ditertiary butyl p cresol of 1.5 weight parts, in temperature, be to react 2h at 110 ℃;
4) to the oil of mirbane that adds 0.3 weight part in the reacted product of step 3), in temperature, be to react 1.5h at 115 ℃, then add the Propylene glycol monoacrylate reaction 1h of 20 weight parts to be uniformly mixed and to vacuumize and obtain product.
Embodiment 4
The performance test of the product that embodiment 1 ~ 3 is made, contrast adopts 6606 products of Jiangsu San Mu company according to GB/T 264-83 method test acid number; Rotational viscosimeter tested viscosity, contains admittedly according to the test of GB/T7193.3-1987 method.Concrete detected result is as shown in table 1.
The performance of table 1 polyester acrylate
Embodiment 5
Adopt epoxide modified polyester acrylate resin (10 weight part), thinner (5 weight part), light trigger (0.2 weight part), auxiliary agent (0.1 weight part) the preparation ultraviolet-curing paint of embodiment 1 preparation.Wherein, thinner is Changxing, the Taiwan EM223 of company product, and light trigger is Changsha company of Sunyu 1173 products, and auxiliary agent is the German BYK BYK-333 of company flow agent product.
Wherein, light trigger is for can produce the material of free radical further initiated polymerization through illumination, in photocuring system, comprise UV glue, UV coating, UV ink etc., after acceptance or absorption outside energy, itself there is chemical transformation, be decomposed into free radical or positively charged ion, thus initiated polymerization.Preparation ultraviolet-curing paint light trigger used can adopt ，Ru Changsha, commercially available prod company of Sunyu 1173 products.
Thinner is a kind of in order to reduce resin viscosity, improves its processing performance and the liquid substance good with resin compatibility that add, can adopt ，Ru Taiwan, the various commercially available prod EM223 of Changxing company product.
The auxiliary agent adopting in the present embodiment is flow agent, a kind of conventional coatings additive(s), can impel coating in drying and forming-film process, form one smooth, smooth, film uniformly, can adopt various commercially available prod, as the German BYK BYK-333 of company flow agent product.
Embodiment 6
Adopt epoxide modified polyester acrylate resin (50 weight part), thinner (10 weight part), light trigger (8 weight part), auxiliary agent (1 weight part) the preparation ultraviolet-curing paint of embodiment 1 preparation.Wherein, thinner is Changxing, the Taiwan EM223 of company product, and light trigger is Changsha company of Sunyu 1173 products, and auxiliary agent is the German BYK BYK-333 of company flow agent product.
Embodiment 7
Adopt epoxide modified polyester acrylate resin (25 weight part), thinner (7 weight part), light trigger (3 weight part), auxiliary agent (0.6 weight part) the preparation ultraviolet-curing paint of embodiment 1 preparation.Wherein, thinner is Changxing, the Taiwan EM223 of company product, and light trigger is Changsha company of Sunyu 1173 products, and auxiliary agent is the German BYK BYK-333 of company flow agent product.
Embodiment 8
The performance test of ultraviolet-curing paint
Adopt the method shown in table 2 to test the performance of the ultraviolet-curing paint of embodiment 5 ~ 7 preparations, result is as shown in table 2.
The performance of table 2 ultraviolet-curing paint
Under light trigger coexists, through ultraviolet radiation, can there is rapidly radical polymerization in epoxide modified polyester acrylate resin of the present invention, thus crosslinking curing.Result shows, the present invention improves the fragility of polyester acrylate resin to a certain extent, and it is fast that the ultraviolet-curing paint that preparation obtains has curing speed, and viscosity is high, the feature that snappiness is good.And improved the chemical resistance of UV curing system, resistance to acids and bases, water tolerance, paint film is bubble not, and any variation does not occur.Product has good coating film gloss degree more than 90.And snappiness, environment-protecting asepsis, production cost is low.
Visible, modified poly ester acrylate resin of the present invention can be used in preparation photo-cured coating, and light-curable ink, is suitable for plastic cement, the photocuring application of paper.Can be cured film extremely low cure shrinkage is provided, excellent adhesive attraction and snappiness, be that a class has good prospect and the superior light-cured resin of over-all properties.
All documents of mentioning in the present invention are all quoted as a reference in this application, just as each piece of document, are quoted as a reference separately.In addition should be understood that those skilled in the art can make various changes or modifications the present invention after having read above-mentioned teachings of the present invention, these equivalent form of values fall within the application's appended claims limited range equally.
Claims (10)
1. a modified poly ester acrylate, is characterized in that, is epoxy group(ing) modified poly ester acrylate, has following one or more feature:
(a) acid number≤5mgKOH/g;
(b) viscosity is 20000 ~ 30000Mpa.s.
2. a preparation method for modified poly ester acrylate as claimed in claim 1, is characterized in that, said method comprising the steps of:
1) diprotic acid of the epoxy resin of 40～60 weight parts and 10～30 weight parts is added in reactor, at 100 ~ 105 ℃, react 1 ~ 3h;
2) to the vinylformic acid that adds 20～40 weight parts in reactor, at 105～110 ℃, react 1 ~ 2h;
3) to step 2) add the catalyzer of 0.5～1 weight part in reacted product, then under nitrogen protection, add the promoter of 0.8～1.5 weight part, in temperature, be to react 1～2h at 110～112 ℃;
4) to the oil of mirbane that adds 0.1～0.5 weight part in the reacted product of step 3), in temperature, be to react 1～2h at 110～115 ℃, then add the acrylate monomer of 10 ~ 30 weight parts, stir, vacuumize, react 1 ~ 2h and obtain described modified poly ester acrylate.
3. preparation method as claimed in claim 2, is characterized in that, the molecular weight of the epoxy resin described in described step 1) is 500～1000, and described diprotic acid is Tetra hydro Phthalic anhydride.
4. preparation method as claimed in claim 2, is characterized in that, the epoxy resin described in described step 1) is bisphenol A type epoxy resin E-51.
5. preparation method as claimed in claim 2, is characterized in that, the catalyzer described in described step 3) is triethylamine, and described promoter is 2,6 ditertiary butyl p cresol.
6. preparation method as claimed in claim 2, is characterized in that, the acrylate monomer described in described step 4) is tripropylene glycol diacrylate or Propylene glycol monoacrylate.
7. preparation method as claimed in claim 2, is characterized in that, the acrylate monomer described in described step 4) is Propylene glycol monoacrylate.
8. a ultraviolet-curing paint, is characterized in that, described ultraviolet-curing paint comprises modified poly ester acrylate claimed in claim 1.
9. coating as claimed in claim 8, is characterized in that, described coating also comprises thinner, light trigger and flow agent.
10. coating as claimed in claim 9, is characterized in that, described coating comprises modified poly ester acrylate described in 10-50 weight part; Thinner described in 5-10 weight part; 0.1-10 weight part light trigger; 0.1-1 weight part flow agent.
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| CN201210214969.XA CN103509162A (en) | 2012-06-27 | 2012-06-27 | Epoxy-modified polyester acrylate and preparation method thereof |
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| CN201210214969.XA CN103509162A (en) | 2012-06-27 | 2012-06-27 | Epoxy-modified polyester acrylate and preparation method thereof |
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Cited By (4)
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| CN106752749A (en) * | 2016-12-30 | 2017-05-31 | 澳达树熊涂料(惠州)有限公司 | A kind of UV white primer coating sprayed on MDF and preparation method thereof |
| CN107189022A (en) * | 2017-06-30 | 2017-09-22 | 华仁药业股份有限公司 | A kind of non-PVC peritoneal dialysis bag transfusion membrane material and preparation method thereof |
| CN108912941A (en) * | 2017-03-22 | 2018-11-30 | 比亚迪股份有限公司 | 3D glass decoration coating composition and 3D glass and preparation method thereof |
| CN109863189A (en) * | 2016-10-13 | 2019-06-07 | 巴斯夫欧洲公司 | Radiation-hardenable composition containing polyester acrylate |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109863189A (en) * | 2016-10-13 | 2019-06-07 | 巴斯夫欧洲公司 | Radiation-hardenable composition containing polyester acrylate |
| CN109863189B (en) * | 2016-10-13 | 2021-05-28 | 巴斯夫欧洲公司 | Radiation curable compositions containing polyester acrylates |
| CN106752749A (en) * | 2016-12-30 | 2017-05-31 | 澳达树熊涂料(惠州)有限公司 | A kind of UV white primer coating sprayed on MDF and preparation method thereof |
| CN108912941A (en) * | 2017-03-22 | 2018-11-30 | 比亚迪股份有限公司 | 3D glass decoration coating composition and 3D glass and preparation method thereof |
| CN108912941B (en) * | 2017-03-22 | 2019-12-10 | 比亚迪股份有限公司 | coating composition for 3D glass decoration, 3D glass and preparation method thereof |
| CN107189022A (en) * | 2017-06-30 | 2017-09-22 | 华仁药业股份有限公司 | A kind of non-PVC peritoneal dialysis bag transfusion membrane material and preparation method thereof |
| CN107189022B (en) * | 2017-06-30 | 2019-08-09 | 华仁药业股份有限公司 | A kind of non-PVC peritoneal dialysis bag infusion membrane material and preparation method thereof |
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Address after: 8555 No. 201707 Shanghai city Qingpu District Songze Avenue Applicant after: Shanghai Zhanchen Paint Co., Ltd. Applicant after: Zhanchen Coatings Group Co., Ltd. Applicant after: Beijing Zhanchen Chemical Industry Co., Ltd. Applicant after: Qingdao Zhan Chen novel material company limited Applicant after: Chengdu Zhanchen Chemical Co., Ltd. Address before: 8555 No. 201707 Shanghai city Qingpu District Songze Avenue Applicant before: Shanghai Fuchen Chemical Co., Ltd. Applicant before: Zhanchen Coatings Group Co., Ltd. Applicant before: Beijing Zhanchen Chemical Industry Co., Ltd. Applicant before: Qingdao Fuchen Chemical Co., Ltd. Applicant before: Chengdu Zhanchen Chemical Co., Ltd. |
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Free format text: CORRECT: APPLICANT; FROM: SHANGHAI FUCHEN CHEMICAL CO. LTD. TO: SHANGHAI ZHANCHEN PAINT CO., LTD. Free format text: CORRECT: APPLICANT; FROM: ZHANCHEN COATINGS GROUP CO., LTD. BEIJING ZHANCHEN CHEMICAL INDUSTRY CO., LTD. QINGDAO VISION CHEMICAL CO., LTD. CHENGDU ZHANCHEN CHEMICAL CO., LTD. TO: ZHANCHEN COATINGS GROUP CO., LTD. BEIJING ZHANCHEN CHEMICAL INDUSTRY CO., LTD. QINGDAO ZHANCHEN NEW MATERIAL CO., LTD. CHENGDU ZHANCHEN CHEMICAL CO., LTD. |
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Address after: 8555 No. 201707 Shanghai city Qingpu District Songze Avenue Applicant after: Shanghai Zhanchen Paint Co., Ltd. Applicant after: CHINA ZHANCHEN PAINTS GROUP LTD. Applicant after: Beijing Zhan Chen novel material company limited Applicant after: Qingdao Zhan Chen novel material company limited Applicant after: Chengdu Zhan Chen coating company limited Address before: 8555 No. 201707 Shanghai city Qingpu District Songze Avenue Applicant before: Shanghai Zhanchen Paint Co., Ltd. Applicant before: Zhanchen Coatings Group Co., Ltd. Applicant before: Beijing Zhanchen Chemical Industry Co., Ltd. Applicant before: Qingdao Zhan Chen novel material company limited Applicant before: Chengdu Zhanchen Chemical Co., Ltd. |
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Application publication date: 20140115 |