CN101993678A - Ultraviolet curing glue and preparation method thereof - Google Patents
Ultraviolet curing glue and preparation method thereof Download PDFInfo
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- CN101993678A CN101993678A CN2009101896561A CN200910189656A CN101993678A CN 101993678 A CN101993678 A CN 101993678A CN 2009101896561 A CN2009101896561 A CN 2009101896561A CN 200910189656 A CN200910189656 A CN 200910189656A CN 101993678 A CN101993678 A CN 101993678A
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- cured adhesive
- ultraviolet cured
- reactive thinner
- aliphatic urethane
- group reactive
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Abstract
The invention belongs to the technical field of glue and in particular relates to ultraviolet curing glue and a preparation method thereof. The ultraviolet curing glue comprises 50-75 percent of oligomer, 0-13 percent of single functional group active diluent, 20-35 percent of multi-functional group active diluent and 1-5 percent of photoinitiator. The oligomer is aliphatic urethane acrylate resin with the functionality of 2-4; the single functional group active diluent is selected from IBOA, IBOMA, beta-CEA and THFA); the multi-functional group active diluent is selected from HDDA, TPGDA and TMPTA; and the photoinitiator is selected from 1-hydroxyl-cyclohexylbenzophenone and 2,4,6-trimethylbenzoyl-diphenylphosphine oxide. The invention also discloses a preparation method of the ultraviolet curing glue. The ultraviolet curing glue has the advantages of lower brittleness, favorable ultraviolet resistance, no ordor, small shrinkage stress, corrosion resistance and lower manufacture cost, is transparent and is suitable for mass production.
Description
Technical field
The present invention relates to the technical field of glue, be specifically related to a kind of ultraviolet cured adhesive and preparation method thereof.
Background technology
At present, UV Pattern (ultraviolet pattern) technology provides a kind of new button moulding process.
The ultraviolet cured adhesive that this technology utilization is coated on the base material (being generally PC or PET) issues the biochemical crosslinked curing molding that comes in the initiation of UV-light.This technology almost is to carry out at normal temperatures and pressures, has avoided the High Temperature High Pressure of injection moulding; Ultra-thin and the lines of its button is mainly by mould control, and used mould is with respect to injection mold, and its design is comparatively simple, precision is high.Therefore, UV Pattern technology is realizing that the aspects such as transfer printing of seamless combination and meticulous lines are having special advantages between ultra-thin, integrated, the button of Keypad (miniature keyboard).
High-quality Keypad has higher requirement to the ultra-violet resistance and the fragility of ultraviolet cured adhesive.But it is relatively poor to have used its UV resistant performance of ultraviolet cured adhesive of UV Pattern technology now, and the fragility height.
Summary of the invention
Technical problem to be solved by this invention is: ultraviolet cured adhesive ultraviolet resistance of the prior art is poor, and the fragility height.Thereby provide a kind of ultra-violet resistance strong, the ultraviolet cured adhesive that fragility is lower.
A kind of ultraviolet cured adhesive, it comprises by weight percentage:
Oligopolymer 50～75%
Simple function group reactive thinner 0～13%
Polyfunctional group reactive thinner 20～35%
Light trigger 1～5%;
Described oligopolymer is that functionality is the aliphatic urethane acrylate of 2-4;
Described simple function group reactive thinner is selected among iso-bornyl acrylate IBOA, isobornyl methacrylic ester IBOMA, β-propyloic acrylic ester β-CEA, the vinylformic acid tetrahydrofuran ester THFA one or more;
Described polyfunctional group reactive thinner is selected among 1,6 hexanediol diacrylate HDDA, tripropylene glycol diacrylate TPGDA, the Viscoat 295 TMPTA one or more;
Described light trigger is selected from 1-hydroxyl-phenylcyclohexane ketone, 2,4, in 6-trimethylbenzoyl-diphenyl phosphine oxide one or more.
The present invention also provides a kind of preparation method of above-mentioned ultraviolet cured adhesive, and it comprises the steps:
With oligopolymer, simple function group reactive thinner and polyfunctional group reactive thinner, fully mix, add light trigger again, stir, leave standstill or vacuumize the bubble in the system of removing then.
Ultraviolet cured adhesive provided by the present invention has good ultraviolet resistance and lower fragility, and transparent, odorlessness, string stress are little, corrosion-resistant.Cost of manufacture of the present invention is lower, is fit to scale operation.
Specific embodiments
A kind of ultraviolet cured adhesive, it comprises by weight percentage:
Oligopolymer 50～75%
Simple function group reactive thinner 0～13%
Polyfunctional group reactive thinner 20～35%
Light trigger 1～5%;
Described oligopolymer is that functionality is the aliphatic urethane acrylate of 2-4;
Described simple function group reactive thinner is selected among iso-bornyl acrylate IBOA, isobornyl methacrylic ester IBOMA, β-propyloic acrylic ester β-CEA, the vinylformic acid tetrahydrofuran ester THFA one or more;
Described polyfunctional group reactive thinner is selected among 1,6 hexanediol diacrylate HDDA, tripropylene glycol diacrylate TPGDA, the Viscoat 295 TMPTA one or more;
Described light trigger is selected from 1-hydroxyl-phenylcyclohexane ketone, 2,4, in 6-trimethylbenzoyl-diphenyl phosphine oxide one or more.
Functionality among the present invention is known in those skilled in the art, and the functionality of urethane acrylate is meant and contains the mole number that can participate in polyreaction carbon-carbon double bond group in every mole of polyurethane acrylate resin.
Wherein, functionality is that the aliphatic urethane acrylate of 2-4 is meant that functionality is in 2 to 4 aliphatic urethane acrylate resin.Aliphatic urethane diacrylate resin (functionality 2) for example, aliphatic polyurethane triacrylate resin (functionality 3), the U680H that also has bayer company be exactly functionality be 3.8 aliphatic urethane acrylate resin.
Wherein, functionality of the present invention is the aliphatic urethane acrylate of 2-4, preferably chooses following material:
Functionality be 3.8 aliphatic urethane acrylate resin,
In the time of 25 ℃ viscosity be 120000-260000cps aliphatic polyurethane triacrylate resin,
Elongation the aliphatic urethane diacrylate resin more than 400%,
Second-order transition temperature is-25 ℃ of aliphatic urethane diacrylate resins.
Wherein, simple function group reactive thinner of the present invention, polyfunctional group reactive thinner all belong to reactive thinner, and its common effect is dissolving or is dispersed into membrane substance, and participates in film formation reaction.Each molecule of simple function group reactive thinner only contains a group that can participate in curing reaction, and each molecule of polyfunctional group reactive thinner contains at least two groups that can participate in curing reaction.
The preferred vinylformic acid tetrahydrofuran ester of simple function group reactive thinner of the present invention THFA; The preferred 1,6 hexanediol diacrylate HDDA of polyfunctional group reactive thinner.
More preferably, the concrete composition of ultraviolet cured adhesive of the present invention is preferably as follows:
Functionality is 3.8 aliphatic urethane acrylate resin 40～46%
Second-order transition temperature is-25 ℃ of aliphatic urethane diacrylate resins 15～20%
Vinylformic acid tetrahydrofuran ester 8～13%
1,6 hexanediol diacrylate 24～29%
1-hydroxyl-phenylcyclohexane ketone 1.8～2.1%
2,4,6-trimethylbenzoyl-diphenyl phosphine oxide 0.4～0.6%
Another concrete composition of the present invention is preferably as follows:
Functionality is 3.8 aliphatic urethane acrylate resin 35～40%
Viscosity is the aliphatic polyurethane triacrylate resin 25～30% of 120000～260000cps (25 ℃)
Elongation is at the aliphatic urethane diacrylate more than 400% 4～8%
1,6 hexanediol diacrylate 25～30%
1-hydroxyl-phenylcyclohexane ketone 1.8～2.2%.
The flow agent that ultraviolet cured adhesive of the present invention can also contain is to increase the levelling property of ultraviolet cured adhesive.
Described flow agent is conventionally known to one of skill in the art, EFKA3883, EFKA3886, the EFKA3600 of for example Dutch Ai Fuka company, the BYK366 of BYK company, BYK333, BYK307, the DEGO410 of German Di Gao company, the F41 of German Cognis.The preferred DEGO410 of the present invention.
The preferred flow agent addition of the present invention is: the gross weight with oligopolymer, reactive thinner and light trigger is a benchmark, and the addition of flow agent is 0.1-1.5%
In the actual production process, chemical substance all can adopt the Chemicals that are purchased among the present invention.
Satisfy functionality among the present invention and be 3.8 aliphatic urethane acrylate resin, can select the U680H resin of bayer company for use, perhaps the identical product of other companies.
Satisfying viscosity is the aliphatic polyurethane triacrylate resin of 120000-260000cps (25 ℃), can select the 1527B of bayer company for use, perhaps the identical product of other companies.
Satisfy elongation at the aliphatic urethane diacrylate resin more than 400%, can select 2491 of bayer company for use, perhaps the identical product of other companies.
Satisfying second-order transition temperature is-25 ℃ of aliphatic urethane diacrylate resins, can select 4529 of bayer company for use, perhaps the identical product of other companies.
The vinylformic acid tetrahydrofuran ester can adopt the SR285 of Sartomer company.
1,6 hexanediol diacrylate can adopt the EM221 of Changxing, Taiwan company.
1-hydroxyl-phenylcyclohexane ketone can adopt Irgacure 184.
2,4,6-trimethylbenzoyl-diphenyl phosphine oxide can adopt the TPO of Ciba company.
Ultraviolet light polymerization glue provided by the present invention, wherein to adopt functionality be the polyurethane acrylate resin of 2-4 to oligopolymer, it has good weather, yellowing resistance, and sticking power and scraping and wiping resistance performance preferably.
A kind of preparation method of above-mentioned ultraviolet cured adhesive, it comprises the steps: urethane acrylate and simple function group reactive thinner, polyfunctional group reactive thinner are fully mixed, and adds light trigger again, stir, leave standstill or vacuumize the bubble in the system of removing then.
Be specially and proportionally in container, add oligopolymer, simple function group reactive thinner, polyfunctional group reactive thinner, stir 10min with electric mixer and mix; Add light trigger then, stir 10min with electric mixer again and mix; Left standstill 24 hours or vacuumized 2 hours at last to remove the bubble in the ultraviolet cured adhesive.
The present invention is further elaborated below in conjunction with specific embodiment.
Embodiment 1
The composition of ultraviolet cured adhesive such as following table:
In container according in the table ratio add oligopolymer, simple function group reactive thinner, polyfunctional group reactive thinner, stir 10min with electric mixer and mix; Add light trigger then in proportion, stir 10min with electric mixer again and mix; Left standstill 24 hours or vacuumized 2 hours at last to remove the bubble in the ultraviolet cured adhesive.
Embodiment 2
The composition of ultraviolet cured adhesive such as following table:
Method preparation according to embodiment 1.
Embodiment 3
The composition of ultraviolet cured adhesive such as following table:
Method preparation according to embodiment 1.
Embodiment 4
The composition of ultraviolet cured adhesive such as following table:
Method preparation according to embodiment 1.
Embodiment 5
The composition of ultraviolet cured adhesive such as following table:
Method preparation according to embodiment 1.
Embodiment 6
Different is with embodiment 1: adding flow agent DEGO410 again in its prescription, is benchmark with the total amount of oligopolymer, reactive thinner and light trigger, and the addition of flow agent is 0.2%.
Method preparation according to embodiment 1 adds flow agent at last again, mixes.
Comparative Examples 1
The composition of ultraviolet cured adhesive such as following table:
Method preparation according to embodiment 1.
Comparative Examples 2
The composition of ultraviolet cured adhesive such as following table:
Method preparation according to embodiment 1.
Performance test:
The QUV test: the ultraviolet exposure of first 4h (UV-A, 340nm, 60 ℃), back 4h moisture exposure (50 ℃) is an one-period, repeats the above-mentioned cycle.Bad phenomenon such as variable color or yellowing appear when certain cycle product, then the cycle of its front be product can the cycle life of anti-QUV.Measure product can the cycle life of anti-QUV.
The fragility test: load the power of 7N, frequency is 4 times/s, and the test ultraviolet cured adhesive does not occur ftractureing or the phenomenon maximum of crackle can be born number of times.It is many more that it bears number of times, and expression fragility is low more.
SaltSprayTest: temperature+35 ℃, the brine spray 2h of NaCl 5%.Temperature+40 ℃, the fate of its storage is calculated in relative humidity 95% storage.
The thermal shock test :-40 ℃ /+85 ℃, the time=3min of variation, 1 circulation=2h/2h, test UV glue can bear cycle index.
Pencil hardness test:
Press GB6739-86 hardness of film pencil assay method and measure, represent with pencil hardness.
Table 1
As can be seen from Table 1, the UV resistant cycle of the relative Comparative Examples 1-2 of embodiment 1-6 has had significantly improves, and illustrates that ultraviolet performance of the ultraviolet cured adhesive of embodiment 1-6 significantly improves.And the number of times that fragility test is born obviously increases, and represents that its fragility obviously reduces.
It can also be seen that from table 1 performance at aspects such as SaltSprayTest, thermal shock and pencil hardnesss also shows good.
Claims (10)
1. ultraviolet cured adhesive, it comprises by weight percentage:
Oligopolymer 50～75%
Simple function group reactive thinner 0～13%
Polyfunctional group reactive thinner 20～35%
Light trigger 1～5%;
Described oligopolymer is that functionality is 2～4 aliphatic urethane acrylate resin;
Described simple function group reactive thinner is selected from iso-bornyl acrylate, isobornyl methacrylic ester, β-propyloic acrylic ester, the vinylformic acid tetrahydrofuran ester one or more;
Described polyfunctional group reactive thinner is selected from 1,6 hexanediol diacrylate, tripropylene glycol diacrylate, the Viscoat 295 one or more;
Described light trigger is selected from 1-hydroxyl-phenylcyclohexane ketone, 2,4, in 6-trimethylbenzoyl-diphenyl phosphine oxide one or more.
2. ultraviolet cured adhesive according to claim 1 is characterized in that: described functionality is that 2～4 aliphatic urethane acrylate resin is selected from: the aliphatic polyurethane triacrylate resin that functionality is 3.8 aliphatic urethane acrylate resin, viscosity is 120000～260000cps 25 ℃ time the, elongation the aliphatic urethane diacrylate more than 400%, second-order transition temperature for-25 ℃ of aliphatic urethane diacrylate resins in one or more.
3. ultraviolet cured adhesive according to claim 1 is characterized in that: described simple function group reactive thinner is the vinylformic acid tetrahydrofuran ester.
4. ultraviolet cured adhesive according to claim 1 is characterized in that: described polyfunctional group reactive thinner is a 1,6 hexanediol diacrylate.
5. ultraviolet cured adhesive according to claim 2 is characterized in that: described ultraviolet cured adhesive comprises:
Functionality is 3.8 aliphatic urethane acrylate resin 40～46%
Second-order transition temperature is-25 ℃ of aliphatic urethane diacrylate resins 15～20%
Vinylformic acid tetrahydrofuran ester 8～13%
1,6 hexanediol diacrylate 24～29%
1-hydroxyl-phenylcyclohexane ketone 1.8～2.1%
2,4,6-trimethylbenzoyl-diphenyl phosphine oxide 0.4～0.6%
6. ultraviolet cured adhesive according to claim 2 is characterized in that: described ultraviolet cured adhesive comprises:
Functionality is 3.8 aliphatic urethane acrylate resin 35～40%
Viscosity is the aliphatic polyurethane triacrylate resin 25～30% of 120000～260000cps in the time of 25 ℃
Elongation is at 400% above aliphatic urethane diacrylate 4～8%
1,6 hexanediol diacrylate 25～30%
1-hydroxyl-phenylcyclohexane ketone 1.8～2.2%
7. ultraviolet cured adhesive according to claim 1 is characterized in that: also contain flow agent.
8. ultraviolet cured adhesive according to claim 1 is characterized in that: described flow agent is a polysiloxane-polyether copolymer.
9. ultraviolet cured adhesive according to claim 1 is characterized in that: the total amount with oligopolymer, reactive thinner and light trigger is a benchmark, and the addition of flow agent is 0.1-1.5%
10. the preparation method of the described ultraviolet cured adhesive of claim 1, it comprises: with oligopolymer, simple function group reactive thinner and polyfunctional group reactive thinner, fully mix, add light trigger again, stir, leave standstill or vacuumize the bubble in the system of removing then.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN 200910189656 CN101993678B (en) | 2009-08-26 | 2009-08-26 | Ultraviolet curing glue and preparation method thereof |
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| CN 200910189656 CN101993678B (en) | 2009-08-26 | 2009-08-26 | Ultraviolet curing glue and preparation method thereof |
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| CN101993678A true CN101993678A (en) | 2011-03-30 |
| CN101993678B CN101993678B (en) | 2013-08-07 |
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Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103436213A (en) * | 2013-09-09 | 2013-12-11 | 烟台德邦科技有限公司 | Ultraviolet-curing type optical resin adhesive and preparation method thereof |
| CN103725204A (en) * | 2012-10-10 | 2014-04-16 | 第一毛织株式会社 | Anisotropic conductive adhesive composition, film and semiconductor device |
| CN104893594A (en) * | 2015-06-04 | 2015-09-09 | 王行柱 | Glass laminated UV-curing protection glue and preparation method thereof |
| CN105925238A (en) * | 2016-06-28 | 2016-09-07 | 烟台信友新材料股份有限公司 | UV-curing adhesive with low Tg point and high permeability and preparation method thereof |
| CN106497387A (en) * | 2016-10-20 | 2017-03-15 | 连云港华海诚科电子材料有限公司 | Photochromic nano silver metal grid nesa coating ultraviolet photocureable material |
| CN107987786A (en) * | 2017-12-14 | 2018-05-04 | 黑龙江省科学院石油化学研究院 | A kind of lower glass transition temperatures ultraviolet photo-curing cementing agent and preparation method thereof |
| CN109575764A (en) * | 2018-11-09 | 2019-04-05 | 宁波激智科技股份有限公司 | A kind of coating composition for spreading the composite membrane laminating layer that adds lustre to and a kind of diffusion add lustre to composite membrane and preparation method thereof |
| CN110845986A (en) * | 2018-08-20 | 2020-02-28 | 纳晶科技股份有限公司 | Glue composition, quantum dot composite material and application thereof |
| CN110964476A (en) * | 2018-09-30 | 2020-04-07 | 惠州比亚迪实业有限公司 | Ultraviolet light curing adhesive composition, transfer curing adhesive and preparation method |
| CN111164176A (en) * | 2017-10-05 | 2020-05-15 | 昭和电工株式会社 | Adhesive composition and adhesive sheet |
| CN111592853A (en) * | 2020-06-15 | 2020-08-28 | 歌尔股份有限公司 | Preparation method and application method of ultraviolet light curing glue and ultraviolet light curing glue |
| CN111690368A (en) * | 2020-07-06 | 2020-09-22 | 东莞市派乐玛新材料技术开发有限公司 | UV sealant and preparation method and application thereof |
| CN114773982A (en) * | 2021-12-13 | 2022-07-22 | 华东理工大学 | UV-cured polyurethane acrylate coating and preparation method thereof |
| CN114989779A (en) * | 2022-07-22 | 2022-09-02 | 浙江至格科技有限公司 | Ultraviolet curing glue for manufacturing nano-imprint template and preparation method thereof |
| CN115572572A (en) * | 2022-09-30 | 2023-01-06 | 江苏康进医疗器材有限公司 | Medical UV adhesive for peripherally placing central venous catheter and preparation method thereof |
| CN115825200A (en) * | 2022-11-07 | 2023-03-21 | 叶绿体(北京)生物医药有限公司 | Micro solid calcium ion selective electrode and preparation method thereof |
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| CN103725204A (en) * | 2012-10-10 | 2014-04-16 | 第一毛织株式会社 | Anisotropic conductive adhesive composition, film and semiconductor device |
| CN103725204B (en) * | 2012-10-10 | 2015-10-14 | 第一毛织株式会社 | Anisotropic-electroconductive adhesive composition, film and semiconductor device |
| US9437346B2 (en) | 2012-10-10 | 2016-09-06 | Cheil Industries, Inc. | Semiconductor device connected by anisotropic conductive adhesive film |
| CN103436213A (en) * | 2013-09-09 | 2013-12-11 | 烟台德邦科技有限公司 | Ultraviolet-curing type optical resin adhesive and preparation method thereof |
| CN103436213B (en) * | 2013-09-09 | 2014-11-19 | 烟台德邦科技有限公司 | Ultraviolet-curing type optical resin adhesive and preparation method thereof |
| CN104893594A (en) * | 2015-06-04 | 2015-09-09 | 王行柱 | Glass laminated UV-curing protection glue and preparation method thereof |
| CN105925238A (en) * | 2016-06-28 | 2016-09-07 | 烟台信友新材料股份有限公司 | UV-curing adhesive with low Tg point and high permeability and preparation method thereof |
| CN105925238B (en) * | 2016-06-28 | 2019-01-29 | 烟台信友新材料有限公司 | A kind of ultraviolet cured adhesive and preparation method thereof of low Tg high osmosis |
| CN106497387A (en) * | 2016-10-20 | 2017-03-15 | 连云港华海诚科电子材料有限公司 | Photochromic nano silver metal grid nesa coating ultraviolet photocureable material |
| CN106497387B (en) * | 2016-10-20 | 2018-11-27 | 连云港华海诚科电子材料有限公司 | Photochromic nano silver metal grid transparent conductive film ultraviolet photocureable material |
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| CN110964476A (en) * | 2018-09-30 | 2020-04-07 | 惠州比亚迪实业有限公司 | Ultraviolet light curing adhesive composition, transfer curing adhesive and preparation method |
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| CN114773982A (en) * | 2021-12-13 | 2022-07-22 | 华东理工大学 | UV-cured polyurethane acrylate coating and preparation method thereof |
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| CN115572572A (en) * | 2022-09-30 | 2023-01-06 | 江苏康进医疗器材有限公司 | Medical UV adhesive for peripherally placing central venous catheter and preparation method thereof |
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| CN101993678B (en) | 2013-08-07 |
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