CN102584631B - Urethane polymeric monomer with end groups including vinyl ether and allyl ether and synthetic method thereof - Google Patents
Urethane polymeric monomer with end groups including vinyl ether and allyl ether and synthetic method thereof Download PDFInfo
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Abstract
A urethane photosensitive monomer with end groups including vinyl ether and allyl ether is characterized in that the general formula of the photosensitive monomer is R1OCONH-X-NHCOOR2, wherein R1 refers to a vinyl ether alkyl group, R2 refers to an allyl ether alkyl group, and X shows that the number of carbon atoms in divalent cyclohexyl or a divalent cyclohexyl group with a substitutional group, a divalent aryl group or a divalent aryl group with a substitutional group, divalent diphenylmethane or diphenylmethane with a substitutional group, and a divalent methylene group. The urethane photosensitive monomer has the advantages that the urethane monomer is taken as a polymeric monomer with a photosensitive layer formed through directly platemaking violet laser and a free radical-cation mixed photo-curing coating can improve the adhesive property of the photosensitive layer. The invention further provides a synthetic method which has a simple process, is high in productivity and lower in cost and reduces the environmental pollution.
Description
Technical field
The technical field of the invention is image-forming information recording materials light function field of novel, and namely a kind of end group is the synthetic method of the ammonia ester Type of Collective monomer of vinyl ether and allyl ethers.Specifically, this material is adding under the condition of light trigger, UV-irradiation, and two kinds of two rapid polymerizing curables of key, sensitive layer and the free radical-positively charged ion mixed light that must be used for purple directly laser Graphic are coating material solidified.
Background technology
The mixing cured system of so-called optical free radical-positively charged ion refers to produce simultaneously free radical in same system and two kinds of active grains of positively charged ion are planted, thereby causes simultaneously the system of radical photopolymerization reaction and cationic photopolymerization.Radical photopolymerization has some serious shortcomings: at first, radical photopolymerization is subject to the inhibition of oxygen in air, causes surface cure bad, and state of cure is low, often will solidify inconvenient operation under inert atmosphere; Secondly, low tackiness and to the supersensitivity of skin is arranged; Advantage is: can be applied in widely under suitable initiator, because these monomers and oligopolymer have high polymerizability to produce crosslinked insoluble film, good mechanical property and physical properties be arranged.The cationic photopolymerization system has been compared following advantage with the radical photopolymerization system: be not subjected to oxygen quenching; The active centre life-span is long, and curing reaction is difficult for stopping; The more important thing is that its triggering mechanism does not relate to free radical and excited triplet state, thereby, not by oxygen inhibition, can obtain polymerization fast and completely in air atmosphere.But the cationoid polymerisation system also has the shortcoming of himself, is subjected to influence of moisture large, the impact of environment on every side etc.Make with light positively charged ion-free radical hybrid UV curable paint and can get mutually advantage, give full play to the advantage of free radical and cation photocuring system, thereby improve the photocuring system applicable performance.
With regard to up-to-date documents and materials, do not mix ammonia esters monomer synthetic of type, but second separately
Thiazolinyl ethers monomer and diisocyanate monomer synthesizing cationic type ammonia ester class sensitization monomer (Zeng, Zhaohua; Yang, Jianwen; Pang, Laixing; Chen, Yonglie., Photoinitiated cationic polymerization of urethane vinyl ether crystalline monomers[J] .Polymer International.2006,55 (3), 353-359), perhaps ammonia ester class sensitization monomer (Kayaman-Apohan, the Nilhan of the synthetic free radical type of methyl acrylic ester monomer and vulcabond; Demirci, Ramazan; Cakir, Mustafa; Gungor, Atilla.UV-curable interpenetrating polymer networks based on acrylate/vinylether functionalized urethane oligomers[J] .Radiation Physics and Chemistry.2005,73 (5), 254-262) appear in the newspapers.
Summary of the invention
The present invention proposes the ammonia ester class sensitization monomer that a kind of end group is vinyl ether and allyl ethers, it is characterized in that the general formula of this sensitization monomer is:
R
1OCONH-X-NHCOOR
2
R in formula
1For the vinyl ether alkyl; R
2For the allyl ethers alkyl; X represent the cyclohexyl of divalence or have the aromatic yl group of substituent divalence cyclohexyl groups, divalence or have substituent divalent aryl group, divalence methylene group, divalence ditan or have substituent ditan, the carbonatoms of the methylene group of divalence is 2-6.
A kind of end group is the synthetic method of the ammonia ester class sensitization monomer of vinyl ether and allyl ethers, it is characterized in that its processing step comprises:
Step 1: under the anhydrous and oxygen-free condition, under ice bath, isocyanates monomer and catalyst mix are stirred, and use solvent cut, when system cools to 0-15 ℃, preferred 10 ℃, drip the hydroxyalkyl vinyl ether with solvent cut, after dropwising, be warming up to 20-40 ℃, preferred 30 ℃, continue to stir 1-3h;
Step 2: the product of step 1 is at room temperature continued to stir, drip the hydroxyalkyl allyl ethers solution of solvent cut, after dropwising, be warming up to 40-60 ℃, preferred 50-55 ℃, continue to stir 1-3h, obtains the crude product of the ammonia esters monomer of photo-polymerization type, crude product uses underpressure distillation except desolventizing, obtains containing the ammonia ester class mixed polymerization type sensitization monomer of vinyl ether and allyl ethers.
Catalyzer in step 1 is dibutyl tin laurate.Solvent in step 1 neutralization procedure two is acetone, butanone, toluene, tetrahydrofuran (THF), hexanaphthene, Isosorbide-5-Nitrae-dioxane, methylene dichloride, acetonitrile, and consumption is 1-50 times of raw material.In step 1 catalyst levels be raw material 0.01-0.05 doubly.In step 1, the ratio of the amount of substance of isocyanic ester, hydroxyalkyl vinyl ether and hydroxyalkyl allyl ethers is 1: 1: 1.
Must dewater by purifying before the solvent reaction that uses, namely steam and namely use; The glassware that uses need to dry by the fire and re-use half an hour at 100-110 ℃ of temperature before reaction.
According to the kind of isocyanic ester, catalyzer can add in step 1, also can add in step 2 again.Productive rate is more than 90%.
Obtained following a series of monomeric compounds via above step, concrete structure is as follows:
Monomer A-1 is to A-25:
Monomers B-1 is to B-25:
Monomer C-1 to C-25
Monomer D-1 to D-25:
Monomer E-1 to E-25:
Advantage of the present invention is: contain the ammonia esters monomer of vinyl ether and allyl ethers, under the common existence of radical initiator and cationic initiator, UV-light causes generation cationoid polymerisation and radical polymerization.The final polymerization degree approaches absolutely, has good extent of polymerization and rate of polymerization.Simultaneously, the ammonia esters monomer can improve the tackiness of sensitive layer as polymerization single polymerization monomer and the free radical-positively charged ion hybrid optical solidified coating of the sensitive layer of purple directly laser Graphic.This monomer is stable to visible light, makes storage and transportation comparatively convenient.The present invention introduces same monomer with the two keys of cationic polymerization and free type base polymerisable double bond, has accelerated rate of polymerization, has improved polymerization efficiency, and the advantage of cationoid polymerisation and radical polymerization can be complementary simultaneously.The synthetic method craft that the present invention proposes is simple, and productive rate is high, and cost is lower, has reduced environmental pollution.
Embodiment
[embodiment 1]
The synthetic method of monomer A-2:
16.820g (0.10mol) HDI (hexamethylene diisocyanate) and 0.2ml dibutyl tin laurate are added in the 500mL four-hole bottle, then add the acetone solvent dilution of 100ml, by ice-water bath, stir it is cooled to below 10 ℃.11.616g (0.10mol) 4-hydroxy butyl vinyl ether is dissolved in 50mL acetone, it slowly is added drop-wise in four-hole bottle, remain that the temperature of solution in four-hole bottle, below 10 ℃, approximately dripped off in two hours.After dripping off, remove ice-water bath, be warmed up to 30 ℃ and continue to stir 1.5h, then drip the acetone soln of the 50ml that is dissolved with 5.808g vinyl carbinol (0.10mol), utilize the reaction heat holding temperature 20-40 ℃ of left and right.After dropwising, be warmed up to 50-55 ℃ and continue stirring reaction 2h.Revolve after reaction is completed to steam and remove acetone, obtain colorless transparent viscous liquid, productive rate is about 95%.
[embodiment 2]
The synthetic method of monomer A-7:
With the 4-hydroxy butyl vinyl ether in 3-hydroxypropyl vinyl ether alternative [embodiment 1], all the other reagent and consumption are identical with [embodiment 1].
[embodiment 3]
The synthetic method of monomer A-17:
Substitute the vinyl carbinol in [embodiment 1] with 3-(allyloxy) propane-1-alcohol, the Diethylene Glycol mono vinyl ether substitutes the 4-hydroxy butyl vinyl ether in [embodiment 1], and all the other reagent and consumption are identical with [embodiment 1].
[embodiment 4]
The synthetic method of monomer A-22:
16.820g (0.10mol) HDI (hexamethylene diisocyanate) and 0.2ml dibutyl tin laurate are added in the 500mL four-hole bottle, then add the petroleum ether solvent of 100ml, by stirring ice-water bath, it is cooled to below 10 ℃.8.8105g (0.10mol) 2-hydroxyethyl vinyl ether is dissolved in the 50mL sherwood oil, it slowly is added drop-wise in four-hole bottle, remain that the temperature of solution in four-hole bottle, below 10 ℃, approximately dripped off in two hours.After dripping off, remove ice-water bath, be warmed up to 30 ℃ and continue to stir 1.5h, then drip the petroleum ether solution of the 50ml that is dissolved with 11.6158g 3-(allyloxy) propane-1-alcohol, utilize the reaction heat holding temperature 20-40 ℃ of left and right.After dropwising, be warmed up to 50-55 ℃ and continue stirring reaction 1.5h.Revolve after reaction is completed to steam and remove sherwood oil, obtain colorless transparent viscous liquid, productive rate is about 95%.
[embodiment 5]
The synthetic method of monomers B-3:
22.29g (0.10mol) IPDI (isophorone diisocyanate) and 0.5ml dibutyl tin laurate are added in the 500mL four-hole bottle, then add the acetone solvent dilution of 100ml, mechanical stirring is cooled to below 10 ℃ it by ice-water bath.With 11.616g (0.10mol) 4-hydroxy butyl vinyl ether and being dissolved in 50mL acetone, it slowly is added drop-wise in four-hole bottle, remain that the temperature of solution in four-hole bottle, below 10 ℃, approximately dripped off in two hours.After dripping off, remove ice-water bath, be warmed up to 30 ℃ and continue to stir 2h, then drip the acetone soln of the 50ml that is dissolved with 5.808g (0.10mol) vinyl carbinol, utilize the reaction heat holding temperature 20-40 ℃ of left and right.After dropwising, be warmed up to 50-55 ℃ and continue stirring reaction 1.5h.Revolve after reaction is completed to steam and remove acetone, obtain colorless transparent viscous liquid, productive rate is about 95%.
[embodiment 6]
The synthetic method of monomers B-9:
With the vinyl carbinol in 2-(allyloxy) ethanol alternative [embodiment 5], 3-hydroxypropyl vinyl ether substitutes the 4-hydroxy butyl vinyl ether in [embodiment 5], and all the other reagent and consumption are identical with [embodiment 5].
[embodiment 7]
The synthetic method of monomers B-16:
Substitute the vinyl carbinol in [embodiment 5] with 3-(allyloxy) propane-1-alcohol, all the other reagent and consumption are identical with [embodiment 5].
[embodiment 8]
The synthetic method of monomers B-20:
22.29g (0.10mol) IPDI (isophorone diisocyanate) and 0.5ml dibutyl tin laurate are added in the 500mL four-hole bottle, then add the petroleum ether solvent dilution of 100ml, by the mechanical stirring ice-water bath, it is cooled to below 10 ℃.With 8.816g (0.10mol) 2-hydroxyethyl vinyl ether and being dissolved in the 50mL sherwood oil, it slowly is added drop-wise in four-hole bottle, remain that the temperature of solution in four-hole bottle, below 10 ℃, approximately dripped off in two hours.After dripping off, remove ice-water bath, be warmed up to 30 ℃ and continue to stir 1.8h, then drip the petroleum ether solution of the 50ml that is dissolved with 11.6158g3-(allyloxy) propane-1-alcohol, utilize the reaction heat holding temperature 20-40 ℃ of left and right.After dropwising, be warmed up to 50-55 ℃ and continue stirring reaction 2.5h hour.Revolve after reaction is completed to steam and remove sherwood oil, obtain colorless transparent viscous liquid, productive rate is about 95%.
[embodiment 9]
The synthetic method of monomer C-3:
17.416g (0.10mol) TDI (2,6-toluene-2,4-diisocyanate) and 0.5ml dibutyl tin laurate are added in the 500mL four-hole bottle, then add the acetone solvent of 100ml, mechanical stirring is cooled to below 10 ℃ it by ice-water bath.With 11.616g (0.10mol) 4-hydroxy butyl vinyl ether and being dissolved in 50mL acetone, it slowly is added drop-wise in four-hole bottle, remain the temperature of solution in four-hole bottle below 10 ℃, approximately 2h drips off.After dripping off, remove ice-water bath, be warmed up to 30 ℃ and continue to stir 1.8h hour, then drip the acetone soln of the 50ml that is dissolved with 5.808g (0.10mol) vinyl carbinol, utilize the reaction heat holding temperature 20-40 ℃ of left and right.After dropwising, be warmed up to 50-55 ℃ and continue stirring reaction 2h.Revolve after reaction is completed to steam and remove acetone, obtain colorless transparent viscous liquid, productive rate is about 95%.
[embodiment 10]
The synthetic method of monomer C-9:
With the vinyl carbinol in 2-(allyloxy) ethanol alternative [embodiment 9], 3-hydroxypropyl vinyl ether substitutes the 4-hydroxy butyl vinyl ether in [embodiment 9], and all the other reagent and consumption are identical with [embodiment 9].
[embodiment 11]
The synthetic method of monomer C-16:
Substitute the vinyl carbinol in [embodiment 9] with 3-(allyloxy) propane-1-alcohol, all the other reagent and consumption are identical with [embodiment 9].
[embodiment 12]
The synthetic method of monomer C-20:
17.416g (0.10mol) TDI (2,6-toluene-2,4-diisocyanate) and 0.5ml dibutyl tin laurate are added in the 500mL four-hole bottle, then add the dilution of 100ml petroleum ether solvent, by ice-water bath, stir it is cooled to below 10 ℃.8.816g (0.10mol) 2-hydroxyethyl vinyl ether is dissolved in the 50mL sherwood oil, it slowly is added drop-wise in four-hole bottle, remain that the temperature of solution in four-hole bottle, below 10 ℃, approximately dripped off in 2 hours.After dripping off, remove ice-water bath, be warmed up to 30 ℃ and continue to stir 1.5h, then drip the petroleum ether solution of the 50ml that is dissolved with 11.6158g 3-(allyloxy) propane-1-alcohol, utilize the reaction heat holding temperature 20-40 ℃ of left and right.After dropwising, be warmed up to 50-55 ℃ and continue stirring reaction 1.5h.Revolve after reaction is completed to steam and remove sherwood oil, obtain colorless transparent viscous liquid, productive rate is about 95%.
[embodiment 13]
The synthetic method of monomer D-3:
17.416g (0.10mol) TDI (2,4-toluene-2,4-diisocyanate) and 0.5ml dibutyl tin laurate are added in the 500mL four-hole bottle, then add the acetone solvent of 100ml, mechanical stirring is cooled to below 10 ℃ it by ice-water bath.11.616g (0.10mol) 4-hydroxy butyl vinyl ether is dissolved in 50mL acetone, it slowly is added drop-wise in four-hole bottle, remain that the temperature of solution in four-hole bottle, below 10 ℃, approximately dripped off in two hours.After dripping off, remove ice-water bath, be warmed up to 30 ℃ and continue to stir 1.5h, then drip the acetone soln of the 50ml that is dissolved with 5.808g (0.10mol) vinyl carbinol, utilize the reaction heat holding temperature 20-40 ℃ of left and right.After dropwising, be warmed up to 50-55 ℃ and continue stirring reaction 1.5h.Revolve after reaction is completed to steam and remove acetone, obtain colorless transparent viscous liquid, productive rate is about 95%.
[embodiment 14]
The synthetic method of monomer D-9:
With the vinyl carbinol in 2-(allyloxy) ethanol alternative [embodiment 13], 3-hydroxypropyl vinyl ether substitutes the 4-hydroxy butyl vinyl ether in [embodiment 13], and all the other reagent and consumption are identical with [embodiment 13].
[embodiment 15]
The synthetic method of monomer D-16:
Substitute the vinyl carbinol in [embodiment 13] with 3-(allyloxy) propane-1-alcohol, all the other reagent and consumption are identical with [embodiment 13].
[embodiment 16]
The synthetic method of monomer D-20:
17.416g (0.10mol) TDI (2,4-toluene-2,4-diisocyanate) and 0.5ml dibutyl tin laurate are added in the 500mL four-hole bottle, then add the dilution of 100ml petroleum ether solvent, by ice-water bath, stir it is cooled to below 10 ℃.8.816g (0.10mol) 2-hydroxyethyl vinyl ether is dissolved in the 50mL sherwood oil, it slowly is added drop-wise in four-hole bottle, remain that the temperature of solution in four-hole bottle, below 10 ℃, approximately dripped off in two hours.After dripping off, remove ice-water bath, be warmed up to 30 ℃ and continue to stir 1.5h, then drip the petroleum ether solution of the 50ml that is dissolved with 11.6158g 3-(allyloxy) propane-1-alcohol, utilize the reaction heat holding temperature 20-40 ℃ of left and right.After dropwising, be warmed up to 50-55 ℃ and continue stirring reaction 1.5h.Revolve after reaction is completed to steam and remove sherwood oil, obtain colorless transparent viscous liquid, productive rate is about 95%.
[embodiment 17]
The synthetic method of monomer E-3:
25.026g (0.10mol) (diphenylmethanediisocyanate) and 0.4ml dibutyl tin laurate are added in the 500mL four-hole bottle, then add the acetone solvent dilution of 100ml, mechanical stirring is cooled to below 10 ℃ it by ice-water bath.11.616g (0.10mol) 4-hydroxy butyl vinyl ether is dissolved in 50mL acetone, it slowly is added drop-wise in four-hole bottle, remain that the temperature of solution in four-hole bottle, below 10 ℃, approximately dripped off in two hours.After dripping off, remove ice-water bath, be warmed up to 30 ℃ and continue to stir 1.5h, then drip the acetone soln of the 50ml that is dissolved with 5.808g (0.10mol) vinyl carbinol, utilize the reaction heat holding temperature 20-40 ℃ of left and right.After dropwising, be warmed up to 50-55 ℃ and continue stirring reaction 1.5h.Revolve after reaction is completed to steam and remove acetone, obtain colorless transparent viscous liquid, productive rate is about 95%.
[embodiment 18]
The synthetic method of monomer E-10:
With the vinyl carbinol in 2-(allyloxy) ethanol alternative [embodiment 17], 3-hydroxypropyl vinyl ether substitutes the 4-hydroxy butyl vinyl ether in [embodiment 17], and all the other reagent and consumption are identical with [embodiment 17].
[embodiment 19]
The synthetic method of monomer E-16:
Substitute the vinyl carbinol in [embodiment 17] with 3-(allyloxy) propane-1-alcohol, all the other reagent and consumption are identical with [embodiment 17].
[embodiment 20]
The synthetic method of monomer E-20:
25.026g (0.10mol) TDI (diphenylmethanediisocyanate) and 0.4ml dibutyl tin laurate are added in the 500mL four-hole bottle, then add the 100ml petroleum ether solvent, by ice-water bath, stir it is cooled to below 10 ℃.8.816g (0.10mol) 2-hydroxyethyl vinyl ether is dissolved in the 50mL sherwood oil, it slowly is added drop-wise in four-hole bottle, remain that the temperature of solution in four-hole bottle, below 10 ℃, approximately dripped off in two hours.After dripping off, remove ice-water bath, be warmed up to 30 ℃ and continue to stir 1.5h, then drip the petroleum ether solution of the 50ml that is dissolved with 11.6158g 3-(allyloxy) propane-1-alcohol, utilize the reaction heat holding temperature 20-40 ℃ of left and right.After dropwising, be warmed up to 50-55 ℃ and continue stirring reaction 1.5h.Revolve after reaction is completed to steam and remove sherwood oil, obtain colorless transparent viscous liquid, productive rate is about 95%.
Conclusion
The present invention has designed and synthesized the ammonia ester Type of Collective monomer that a series of end groups are vinyl ether and allyl ethers.This monomer adds initiator that positively charged ion and radical polymerization occur under UV-light.Rate of polymerization is fast, and the polymerization degree is high.Mix the good polymerization of type ammonia esters monomer, the light sensitive layer and the free radical-positively charged ion mixed light that can be used for purple directly laser Graphic are coating material solidified.Synthesis technique is simple, and output is high, has potential using value.
Claims (1)
1.
A kind of end group is the synthetic method of the ammonia ester class sensitization monomer of vinyl ether and allyl ethers, and it is characterized in that: the structural formula of this sensitization monomer is
Synthetic method is:
25.026g diphenylmethanediisocyanate and 0.4ml dibutyl tin laurate are added in the 500mL four-hole bottle, then add the 100ml petroleum ether solvent, by ice-water bath, stir it is cooled to below 10 ℃; The 2-hydroxyethyl vinyl ether of 8.816g is dissolved in the 50mL sherwood oil, it slowly is added drop-wise in four-hole bottle, remain that the temperature of solution in four-hole bottle, below 10 ℃, dripped off in two hours; After dripping off, remove ice-water bath, be warmed up to 30 ℃ and continue stir 1.5h, then drip the petroleum ether solution of the 50ml of 3-(allyloxy) propane that is dissolved with 11.6158g-1-alcohol, utilize the reaction heat holding temperature at 20-40 ℃; After dropwising, be warmed up to 50-55 ℃ and continue stirring reaction 1.5h; Revolve after reaction is completed to steam and remove sherwood oil, obtain the colorless transparent viscous liquid product.
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| CN103224458A (en) * | 2013-04-16 | 2013-07-31 | 沈阳化工大学 | Preparation method of HMA-HDI-HMA diacrylate macromonomer |
| CN103275249B (en) * | 2013-05-24 | 2015-04-22 | 郑州大学 | Free radical photoinitiator containing single vinyl ether group or single propenyl ether group, and preparation method thereof |
| EP3170848A1 (en) * | 2015-11-23 | 2017-05-24 | Henkel AG & Co. KGaA | Cationic photo transfer polymerization |
| CN111484595B (en) * | 2020-05-29 | 2022-05-10 | 广州五行材料科技有限公司 | Low-viscosity polyurethane acrylate and preparation method and application thereof |
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| US4775732A (en) * | 1988-01-11 | 1988-10-04 | Allied-Signal Inc. | Vinyl ether terminated ester and urethane resins from bis(hydroxyalkyl)cycloalkanes |
| CN101165075A (en) * | 2007-09-07 | 2008-04-23 | 香港生产力促进局 | Polyurethane-acrylic ester composite emulsion and preparation method thereof |
| CN101550093A (en) * | 2009-05-15 | 2009-10-07 | 北京化工大学 | Method for preparing dyadic vinyl ethers monomer |
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| EP1491565A1 (en) * | 2002-04-03 | 2004-12-29 | Kyowa Hakko Chemical Co., Ltd. | Polyalkenyl ether resin |
| EP2089445A1 (en) * | 2006-10-09 | 2009-08-19 | Basf Se | Radiation-curable compounds |
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|---|---|---|---|---|
| US4775732A (en) * | 1988-01-11 | 1988-10-04 | Allied-Signal Inc. | Vinyl ether terminated ester and urethane resins from bis(hydroxyalkyl)cycloalkanes |
| CN101165075A (en) * | 2007-09-07 | 2008-04-23 | 香港生产力促进局 | Polyurethane-acrylic ester composite emulsion and preparation method thereof |
| CN101550093A (en) * | 2009-05-15 | 2009-10-07 | 北京化工大学 | Method for preparing dyadic vinyl ethers monomer |
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| Title |
|---|
| Kayaman-Apohan等.UV-curable interpenetrating polymer networks based on acrylate/vinylether functionalized urethane oligomers.《Radiation Physics and Chemistry》.2005,第5卷(第73期),第254-262页. |
| Photoinitiated cationic polymerization of urethane vinyl ether crystalline monomers;Zhaohua Zeng等;《Polym Int》;20051230(第55期);第353-359页 * |
| UV-curable interpenetrating polymer networks based on acrylate/vinylether functionalized urethane oligomers;Kayaman-Apohan等;《Radiation Physics and Chemistry》;20050831;第5卷(第73期);第254-262页 * |
| Zhaohua Zeng等.Photoinitiated cationic polymerization of urethane vinyl ether crystalline monomers.《Polym Int》.2005,(第55期),第353-359页. |
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Denomination of invention: The invention relates to an urethane polymerization monomer with vinyl ether and allyl ether as end groups and a synthesis method thereof Effective date of registration: 20211210 Granted publication date: 20131113 Pledgee: China Construction Bank Jingmen jinlongquan sub branch Pledgor: HUBEI GURUN TECHNOLOGY Co.,Ltd. Registration number: Y2021420000138 |