CN102807835B - A kind of hydrolyzable ultraviolet curing glue and preparation method thereof - Google Patents
A kind of hydrolyzable ultraviolet curing glue and preparation method thereof Download PDFInfo
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- CN102807835B CN102807835B CN201210161040.5A CN201210161040A CN102807835B CN 102807835 B CN102807835 B CN 102807835B CN 201210161040 A CN201210161040 A CN 201210161040A CN 102807835 B CN102807835 B CN 102807835B
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Abstract
The present invention relates to the technical field of ultraviolet curing glue, especially a kind of hydrolyzable ultraviolet curing glue and preparation method thereof.It comprises weight part is 30 ~ 70 performed polymers; 15 ~ 60 reactive thinners; 0 ~ 10 coupling agent; 1 ~ 10 light trigger; 0.1 ~ 2.5 auxiliary agent; And performed polymer has unique structural formula.Preparation method is, reactive thinner is vacuumized dehydration 1 ~ 2h at 110 ~ 120 DEG C of temperature, adds performed polymer and coupling agent, light trigger after being down to room temperature, stirs and makes it to dissolve, finally add auxiliary agent.Mobility of the present invention is strong, is easy to coating, and rapidly, hardening thing has character that is firmly crisp and low-shrinkage, is suitable for mechanical workout, and tool high water absorbing ability, and be easy to dispergation in water, cost is low, and purposes is wide in solidification.Its preparation method has simple, the maneuverable feature of synthesis process.
Description
Technical field
The present invention relates to the technical field of ultraviolet curing glue, especially a kind of hydrolyzable ultraviolet curing glue and preparation method thereof.
Background technology
In the industry grinding manufacturing processedes such as glass, crystal, jewelry, optical mirror slip, high-grade artwork, electronics processing, need a kind of extraordinary sizing agent, require to be easy to coating; Solidification is fast fast, and cured article has character and the good bonding intensity of firmly crisp and low-shrinkage, is suitable for temporarily bonding or covering in the mechanical processing process such as grinding; After machining, cured article tool high water absorbing ability, glued membrane is easy to be hydrolyzed in water, and bonded object is separated; Although traditional ultraviolet curing gluing agent can have good bonding intensity, machine rear bonded object be not easy to be separated or to be separated after glued membrane on object be not easy to remove; Although traditional water-disintegrable sizing agent can realize easily being separated easily after object machines, or bonding strength is not high, or curing speed is very slow, affects the raising of production efficiency and yield rate.
Summary of the invention
Object of the present invention mainly solves the problem of the temporary bonding or covering in the industry grinding manufacturing processedes such as glass, crystal, jewelry, optical mirror slip, high-grade artwork, electronics processing, so a kind of hydrolyzable ultraviolet curing glue is provided, it not only has good bonding intensity, curing speed fast, and after machining, make bonded object be easy to hydrolysis and be separated.
Based on above-mentioned purpose, the present invention is achieved through the following technical solutions: this hydrolyzable ultraviolet curing glue, and comprising weight part is 30 ~ 70 performed polymers; 15 ~ 60 reactive thinners; 0 ~ 10 coupling agent; 1 ~ 10 light trigger; 0.1 ~ 2.5 auxiliary agent; Described performed polymer has following structural formula:
Wherein, one or more of R to be vulcabond be TDI, MDI, HMDI, HDI, IPDI etc. are composite, and m, n, k are natural constant 1,2,3,4 ...
More specifically, described coupling agent is that one or more in γ-aminopropyl triethoxysilane, γ-(2,3-epoxy third oxygen) propyl trimethoxy silicane, γ-(methacryloxypropyl) propyl trimethoxy silicane, vinyl three ('beta '-methoxy oxyethyl group) silane, vinyltrimethoxy silane, vinyltriethoxysilane are composite; Described light trigger be Irgacure 184, darocure 1173, Irgacure819, Irgacure907,369, one or more in TPO, BMF are composite; Described reactive thinner is that one or more in hydroxyethyl methylacrylate, isobornyl methacrylate, lauryl methacrylate(LMA), Isooctyl methacrylate, hexanediol dimethacrylate, polyethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol acrylate trimethyl, monofunctional acrylate are composite; Described auxiliary agent is that one or more in stablizer, adhesion promoter, substrate wetting agents, water suction toughener are composite, wherein stablizer comprises Resorcinol, naphthoquinones, adhesion promoter comprises PM-2, EM39, substrate wetting agents comprises KL245,270, and water suction toughener comprises oxy-compound, starch.
The method preparing this hydrolyzable ultraviolet curing glue is that reactive thinner is vacuumized dehydration 1 ~ 2h at 110 ~ 120 DEG C of temperature, adds performed polymer and coupling agent, light trigger after being down to room temperature, stirs and makes it to dissolve, finally add auxiliary agent; It needs to be noted that the method for prefabricating of described performed polymer comprises two steps:
A) performed polymer in the middle of the urethane that one end is NCO group is synthesized: hydroxy acrylate is vacuumized 1 ~ 2 hour at 100 ~ 120 DEG C, with removing moisture wherein, then 15 ~ 35 DEG C are cooled to, add vulcabond at 50-70 DEG C, react 2 ~ 3.5 hours, obtain the middle performed polymer of urethane that one end is NCO group; The mol ratio of described hydroxy acrylate and vulcabond is 1: 1 ~ 1.1;
B) performed polymer is synthesized: polyvinyl alcohol dissolution is vacuumized 1 ~ 2 hour in reactive thinner at 110 ~ 130 DEG C, with removing moisture wherein, then 15 ~ 40 DEG C are cooled to, add middle performed polymer at 70 ~ 85 DEG C, react 2 ~ 5 hours, obtain the performed polymer that polyvinyl alcohol modification urethane acrylate is namely described; The mol ratio of described polyvinyl alcohol and the middle performed polymer of urethane is 1: 1 ~ 2.5.
Further, A) hydroxy acrylate described in step is that one or more in hydroxyethyl methylacrylate, Rocryl 410, Hydroxyethyl acrylate are composite.
Also further, A) vulcabond described in step is that one or more in IPDI, MDI, HMDI, HDI, TDI are composite.
Again further, B) to be molecular weight be in the polyvinyl alcohol of 18000,120000,200000 that one or more are composite for polyvinyl alcohol described in step.
Feature of the present invention is: hydrolyzable ultraviolet curing glue mobility is strong, be easy to coating, hardening thing has character that is firmly crisp and low-shrinkage, fast setting is suitable for mechanical workout, hardening thing tool high water absorbing ability, be easy to dispergation in water, cost is low, purposes is wide, is applicable to the temporary bonding or covering in the industry grinding manufacturing processedes such as glass, crystal, jewelry, optical mirror slip, high-grade artwork, electronics processing.Its preparation method has simple, the maneuverable feature of synthesis process.
Embodiment
The preparation of performed polymer A: take 72g Rocryl 410 and be placed in there-necked flask, be warming up to 110 DEG C vacuumize dehydration 2h after, be down to 30 DEG C, add 116.6g3-isocyanic ester methylene-3,5,5-trimethylcyclohexylisocyanate (IPDI), heats to 55 degree of reaction 2.5h, obtains performed polymer in the middle of urethane.
Take 100g polyethylene glycol dimethacrylate and be placed in there-necked flask, it is 12000 polyvinyl alcohol that stirring adds 200g molecular weight, after stirring makes it to mix, be warming up to 110 DEG C vacuumize dehydration 2h after, be down to 35 DEG C, add performed polymer in the middle of 29g, stir after making it to mix, add and heat to 75 DEG C of reaction 3.5h, obtain polyvinyl alcohol modification urethane acrylate A.
The preparation of performed polymer B: take 79.2g Rocryl 410 and be placed in there-necked flask, be warming up to 110 DEG C vacuumize dehydration 2h after, be down to 30 DEG C, add 116.6g3-isocyanic ester methylene-3,5,5-trimethylcyclohexylisocyanate (IPDI), heats to 55 degree of reaction 2.5h, obtains performed polymer in the middle of urethane.
Take 300g polyethylene glycol dimethacrylate and be placed in there-necked flask, it is 120000 polyvinyl alcohol that stirring adds 600g molecular weight, after stirring makes it to mix, be warming up to 130 DEG C vacuumize dehydration 1h after, be down to 35 DEG C, add performed polymer in the middle of 43g, stir after making it to mix, add and heat to 75 DEG C of reaction 3.5h, obtain polyvinyl alcohol modification urethane acrylate B.
The preparation of performed polymer C: take 84.5g hydroxyethyl methylacrylate and be placed in there-necked flask, be warming up to 110 DEG C vacuumize dehydration 2h after, be down to 30 DEG C, add 144.3g3-isocyanic ester methylene-3,5,5-trimethylcyclohexylisocyanate (IPDI), heats to 55 degree of reaction 2.5h, obtains performed polymer in the middle of urethane.
Take 500g polyethylene glycol dimethacrylate and be placed in there-necked flask, it is 180000 polyvinyl alcohol that stirring adds 300g molecular weight, after stirring makes it to mix, be warming up to 120 DEG C vacuumize dehydration 1.5h after, be down to 35 DEG C, add performed polymer in the middle of 35g, stir after making it to mix, add and heat to 75 DEG C of reaction 3.5h, obtain polyvinyl alcohol modification urethane acrylate C.
The sizing agent embodiment be mixed with by the polyvinyl alcohol modification urethane acrylate made above is as follows:
Embodiment 1: according to following recipe preparation ultraviolet curing adhesive.Get 16g hydroxyethyl methylacrylate and 25g polyethylene glycol dimethacrylate in there-necked flask, dehydration 2h is vacuumized at being warming up to 115 DEG C, be cooled to room temperature, add 42g polyvinyl alcohol modification urethane acrylate A, 15g urethane acrylate, 4g light trigger 184 and 1gTPO stirring to make it to dissolve, finally add 2g starch to stir, obtain polyvinyl alcohol modification urethane acrylate ultraviolet curing adhesive.
Embodiment 2: according to following recipe preparation polyvinyl alcohol modification urethane acrylate UV tackiness agent.Compound method is with embodiment 1.
Embodiment 3: according to following recipe preparation polyvinyl alcohol modification urethane acrylate UV tackiness agent.Compound method is with embodiment 1.
Embodiment 4: according to following recipe preparation polyvinyl alcohol modification urethane acrylate UV tackiness agent.Compound method is with embodiment 1.
Embodiment 5: according to following recipe preparation polyvinyl alcohol modification urethane acrylate UV tackiness agent.Compound method is with embodiment 1
Embodiment 6: according to following recipe preparation polyvinyl alcohol modification urethane acrylate UV tackiness agent.Compound method is with embodiment 1
By the following method bonding experiment is carried out to embodiment 1--6, line correlation performance test of going forward side by side.The glue of the glass-filled 100 μm that test sample 1mm is thick is solidify under the ultraviolet light intensity of 1000jm/cm2 through energy, and the results listed in the following table.
Test result shows, hydrolyzable ultraviolet curing glue mobility is strong, is easy to coating; Hardening thing has character that is firmly crisp and low-shrinkage, and fast setting is suitable for mechanical workout; Hardening thing tool high water absorbing ability, is easy to dispergation in water.Be applicable to the temporary bonding or covering in the industry grinding manufacturing processedes such as glass, crystal, jewelry, optical mirror slip, high-grade artwork, electronics processing.
The above, it is only preferred embodiment of the present invention, not any pro forma restriction is done to the present invention, every above embodiment is done according to technical spirit of the present invention any simple modification, equivalent variations and modification, all still belong in the scope of technical solution of the present invention.
Claims (21)
1. a hydrolyzable ultraviolet curing glue, comprising weight part is 30 ~ 70 performed polymers; 15 ~ 60 reactive thinners; 0 ~ 10 coupling agent; 1 ~ 10 light trigger; 0.1 ~ 2.5 auxiliary agent; Described performed polymer has following structural formula:
wherein, R be selected from TDI, MDI, HMDI, HDI, IPDI one or more composite vulcabond removing-NCO outside structure, m and m ' is for integer and m+m ' is natural constant, and n is natural constant.
2. a kind of hydrolyzable ultraviolet curing glue according to claim 1, is characterized in that m+m ' is 1,2,3 or 4.
3. a kind of hydrolyzable ultraviolet curing glue according to claim 2, is characterized in that n is 1,2,3 or 4.
4. a kind of hydrolyzable ultraviolet curing glue according to claim 1, it is characterized in that the value of m+m ' make in structural formula derived from the molecular weight of the part of polyvinyl alcohol be 18000,120000,200000 one or more are composite.
5. a kind of hydrolyzable ultraviolet curing glue according to claim 2, it is characterized in that the value of m+m ' make in structural formula derived from the molecular weight of the part of polyvinyl alcohol be 18000,120000,200000 one or more are composite.
6. a kind of hydrolyzable ultraviolet curing glue according to claim 3, it is characterized in that the value of m+m ' make in structural formula derived from the molecular weight of the part of polyvinyl alcohol be 18000,120000,200000 one or more are composite.
7. a kind of hydrolyzable ultraviolet curing glue according to any one of claim 1 to 6, it is characterized in that described coupling agent is that one or more in γ-aminopropyl triethoxysilane, γ-(2,3-epoxy third oxygen) propyl trimethoxy silicane, γ-(methacryloxypropyl) propyl trimethoxy silicane, vinyl three ('beta '-methoxy oxyethyl group) silane, vinyltrimethoxy silane, vinyltriethoxysilane are composite; Described light trigger be Irgacure184, darocure1173, Irgacure819, Irgacure907,369, one or more in TPO are composite; Described reactive thinner is that one or more in hydroxyethyl methylacrylate, hexanediol dimethacrylate, polyethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol acrylate trimethyl, monofunctional acrylate are composite; Described auxiliary agent is that one or more in stablizer, adhesion promoter, substrate wetting agents, water suction toughener are composite, wherein stablizer comprises Resorcinol, naphthoquinones, adhesion promoter comprises PM-2, EM39, substrate wetting agents comprises KL245,270, and water suction toughener comprises oxy-compound, starch.
8. a kind of hydrolyzable ultraviolet curing glue according to claim 7, is characterized in that described monofunctional acrylate is isobornyl methacrylate, lauryl methacrylate(LMA), Isooctyl methacrylate.
9. the method for a kind of hydrolyzable ultraviolet curing glue of preparation according to any one of claim 1 to 8, reactive thinner is vacuumized dehydration 1 ~ 2h at 110 ~ 120 DEG C of temperature, add performed polymer and coupling agent, light trigger after being down to room temperature, stir and make it to dissolve, finally add auxiliary agent; It is characterized in that the method for prefabricating of described performed polymer comprises following steps:
A) performed polymer in the middle of the urethane that one end is NCO group is synthesized: hydroxy acrylate is vacuumized 1 ~ 2 hour at 100 ~ 120 DEG C, with removing moisture wherein, then 15 ~ 35 DEG C are cooled to, add vulcabond at 50-70 DEG C, react 2 ~ 3.5 hours, obtain the middle performed polymer of urethane that one end is NCO group;
The mol ratio of described hydroxy acrylate and vulcabond is 1: 1 ~ 1.1;
B) performed polymer is synthesized: polyvinyl alcohol dissolution is vacuumized 1 ~ 2 hour in reactive thinner at 110 ~ 130 DEG C, to remove moisture wherein, is then cooled to 15 ~ 40 DEG C, add middle performed polymer at 70 ~ 85 DEG C,
React 2 ~ 5 hours, obtain the performed polymer that polyvinyl alcohol modification urethane acrylate is namely described; The mol ratio of described polyvinyl alcohol and the middle performed polymer of urethane is 1: 1 ~ 2.5.
10. the method preparing hydrolyzable ultraviolet curing glue according to claim 9, is characterized in that A) hydroxy acrylate described in step is that one or more in hydroxyethyl methylacrylate, Rocryl 410 are composite.
11. methods preparing hydrolyzable ultraviolet curing glue according to claim 9, is characterized in that A) vulcabond described in step is that one or more in IPDI, MDI, HMDI, HDI, TDI are composite.
12. methods preparing hydrolyzable ultraviolet curing glue according to claim 9, is characterized in that B) to be molecular weight be in the polyvinyl alcohol of 18000,120000,200000 that one or more are composite for polyvinyl alcohol described in step.
13. 1 kinds of hydrolyzable ultraviolet curing glues, comprising weight part is 30 ~ 70 performed polymers; 15 ~ 60 reactive thinners; 0 ~ 10 coupling agent; 1 ~ 10 light trigger; 0.1 ~ 2.5 auxiliary agent; Described performed polymer has following structural formula:
wherein, R be selected from TDI, MDI, HMDI, HDI, IPDI one or more composite vulcabond removing-NCO outside structure, m and m ' is for integer and m+m ' is natural constant, and n is 2.
14. a kind of hydrolyzable ultraviolet curing glues according to claim 13, is characterized in that m+m ' is 1,2,3 or 4.
15. a kind of hydrolyzable ultraviolet curing glues according to claim 13, it is characterized in that the value of m+m ' make in structural formula derived from the molecular weight of the part of polyvinyl alcohol be 18000,120000,200000 one or more are composite.
16. a kind of hydrolyzable ultraviolet curing glues according to claim 14, it is characterized in that the value of m+m ' make in structural formula derived from the molecular weight of the part of polyvinyl alcohol be 18000,120000,200000 one or more are composite.
17. according to claim 13 to a kind of hydrolyzable ultraviolet curing glue according to any one of 16, it is characterized in that described coupling agent is that one or more in γ-aminopropyl triethoxysilane, γ-(2,3-epoxy third oxygen) propyl trimethoxy silicane, γ-(methacryloxypropyl) propyl trimethoxy silicane, vinyl three ('beta '-methoxy oxyethyl group) silane, vinyltrimethoxy silane, vinyltriethoxysilane are composite; Described light trigger be Irgacure184, darocure1173, Irgacure819, Irgacure907,369, one or more in TPO are composite; Described reactive thinner is that one or more in hydroxyethyl methylacrylate, hexanediol dimethacrylate, polyethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol acrylate trimethyl, monofunctional acrylate are composite; Described auxiliary agent is that one or more in stablizer, adhesion promoter, substrate wetting agents, water suction toughener are composite, wherein stablizer comprises Resorcinol, naphthoquinones, adhesion promoter comprises PM-2, EM39, substrate wetting agents comprises KL245,270, and water suction toughener comprises oxy-compound, starch.
18. a kind of hydrolyzable ultraviolet curing glues according to claim 17, is characterized in that described monofunctional acrylate is isobornyl methacrylate, lauryl methacrylate(LMA), Isooctyl methacrylate.
The method of a kind of hydrolyzable ultraviolet curing glue of 19. preparations according to any one of claim 13 to 18, reactive thinner is vacuumized dehydration 1 ~ 2h at 110 ~ 120 DEG C of temperature, performed polymer and coupling agent, light trigger is added after being down to room temperature, stirring makes it to dissolve, and finally adds auxiliary agent; It is characterized in that the method for prefabricating of described performed polymer comprises following steps:
A) performed polymer in the middle of the urethane that one end is NCO group is synthesized: Hydroxyethyl acrylate is vacuumized 1 ~ 2 hour at 100 ~ 120 DEG C, with removing moisture wherein, then 15 ~ 35 DEG C are cooled to, add vulcabond at 50-70 DEG C, react 2 ~ 3.5 hours, obtain the middle performed polymer of urethane that one end is NCO group;
The mol ratio of described Hydroxyethyl acrylate and vulcabond is 1: 1 ~ 1.1;
B) performed polymer is synthesized: polyvinyl alcohol dissolution is vacuumized 1 ~ 2 hour in reactive thinner at 110 ~ 130 DEG C, to remove moisture wherein, is then cooled to 15 ~ 40 DEG C, add middle performed polymer at 70 ~ 85 DEG C,
React 2 ~ 5 hours, obtain the performed polymer that polyvinyl alcohol modification urethane acrylate is namely described; The mol ratio of described polyvinyl alcohol and the middle performed polymer of urethane is 1: 1 ~ 2.5.
20. methods preparing hydrolyzable ultraviolet curing glue according to claim 19, is characterized in that A) vulcabond described in step is that one or more in IPDI, MDI, HMDI, HDI, TDI are composite.
21. methods preparing hydrolyzable ultraviolet curing glue according to claim 19, is characterized in that B) to be molecular weight be in the polyvinyl alcohol of 18000,120000,200000 that one or more are composite for polyvinyl alcohol described in step.
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| CN103396754B (en) * | 2013-08-02 | 2014-08-20 | 深圳市安立新材料有限公司 | Moisture-proof yellowing-resistant liquid optical clear adhesive |
| CN104530991B (en) * | 2014-12-24 | 2016-08-24 | 湖北固润科技股份有限公司 | A kind of aqueous photo-curing binding agent and the application in glass-cutting is processed thereof |
| CN104910853B (en) * | 2015-05-25 | 2017-09-29 | 广州市尤特新材料有限公司 | A kind of UV rapid curings warm water rapid water dispergation and preparation method thereof |
| CN105462537B (en) * | 2015-07-31 | 2020-08-11 | 湖南工业大学 | A UV-curable fast-bonding biomass water-based adhesive |
| EP3424971A1 (en) * | 2017-07-03 | 2019-01-09 | HILTI Aktiengesellschaft | Urethane methacrylate compounds containing reactive resins, and reactive resin systems and their use |
| CN114790376A (en) * | 2021-01-26 | 2022-07-26 | 无锡昊斯特科技有限公司 | Preparation method of UV (ultraviolet) adhesive |
| CN115044344A (en) * | 2022-07-29 | 2022-09-13 | 浙江国能科技有限公司 | UV hydrolysis adhesive for temporary fixing of microelectronic device and preparation method thereof |
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| US6838516B2 (en) * | 2002-07-26 | 2005-01-04 | Great Eastern Resins Industrial Co., Ltd. | Water dispersible polyisocyanate composition and its uses |
| CN102236113B (en) * | 2010-05-01 | 2015-02-11 | 中国航天科技集团公司第四研究院第四十二所 | Ultraviolet-cured hard coating and application thereof |
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