CN105754541A - UV/moisture dual-cured organic silicon resin composition - Google Patents
UV/moisture dual-cured organic silicon resin composition Download PDFInfo
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Abstract
The invention discloses a UV/moisture dual-cured organic silicon resin composition. The composition comprise, by weight, 0.1-50 parts of hydrogen-containing silicone oil, 0.1-2 parts of a moisture curing catalyst and 4-20*10<-6> parts of a UV photoinitiator. The UV/moisture dual-cured organic silicon resin composition has good transparency, can be dual-cured through UV and moisture and needs low curing energy of 1500mJ/cm<2>. Compared with a dealcoholization-type dual-cured organic silicon resin, the de-ketoxime type dual-cured organic silicon resin can be preserved for one year at the normal temperature and has a faster moisture curing rate under the same conditions.
Description
Technical field
The invention belongs to optical adhesive/fluid sealant preparation field, be specifically related to a kind of optically transparent, there is the double; two organic siliconresin constituent solidified of ultraviolet/dampness.
Background technology
Current smart mobile phone and flat board market mostly adopt direct coating technique (DirectBondingorfulllamination) to eliminate the space between LCM and touch screen glass.Many contact panel factories are when carrying out glass gluing, custom adopts the optical adhesive tape OCA(OpticalClearAdhesive that production efficiency is higher, thickness is homogeneous) coating technique, but this technology is when laminating, easily produce bubble and increase fraction defective, and the micro-bubble that cannot find during laminating also expands such as the time.Bubble removing problem can affect outside yield, and owing to optical adhesive tape (OCA) can not be reprocessed, therefore faulty materials can only be scrapped mostly, causes productivity effect lowly and increases laminating factory cost pressure.
Compare OCA, ultraviolet curing optics of liquids transparent resin LOCA(LiquidOpticalClearAdhesive) due to abutted equipment simple, it is possible to reprocess, it is easy to deaeration, the features such as the cost of material is low, be subject to the welcome of increasing touch-control manufacturer.But simultaneously because contact panel frame portion is printed with lighttight ink, ultraviolet can not pass through ink and be irradiated to these places, thus producing uncured region, these regions need to be additionally carried out side light source irradiation and just can ensure that completion of cure, considerably increase equipment cost, reduce production efficiency.
Can not the problem of ultraviolet curing for shadow region, publication number is the optics of liquids transparent resin that the patent of invention of CN102925062A proposes a kind of ultraviolet/add heat dual curing, solving contact panel frame portion can not the difficult problem of ultraviolet curing, but adding heat curing process, production efficiency is not still improved.
Henkel Corp of the U.S. in 2005 discloses that a kind of fast wet is curing and UV-dampness dual cure compositions (publication number is CN1705684A).The compositions provided contains the alpha-carbon being keyed to silicon atom, and reactivity is strong, and moisture-curable speed is fast, and its structure is as follows:
Ultraviolet/dampness the double cured resin adopting this invention is fitted, and contact panel light transmission part can carry out ultraviolet curing, and frame portion can rely on the moisture-curable in air without increasing extra firing equipment, substantially increases production efficiency.Although moisture-curable speed is quickly, but owing to ultraviolet curing mechanism is the radical polymerization by methacryl functional group, photopolymerizable reactive is low, it is necessary to bigger exposure dose could solidify.Additionally radical polymerization system cure shrinkage is big, produces bigger stress, be unsuitable for the laminating purposes of large scale touch screen when causing solidifying.
Within 2012, Beijing University of Chemical Technology Zhang Junying also discloses that a kind of dual-curable polysiloxane acrylate resin and preparation method thereof (publication number is CN102408569A).At N2Under protection, hydroxyl-terminated injecting two methyl siloxane and methacryloxypropyl trimethoxy silane being mixed, add solvent and catalyst, ester exchange reaction obtains pre-product.Rotation is evaporated off solvent, obtains mixture.At room temperature, extract with absolute methanol, be centrifuged and remove solvent, obtaining dual-curable polysiloxane acrylate resin.The same with the patent of Henkel Corp of the U.S., its ultraviolet curing mechanism is the radical polymerization by methacryl functional group, and cure shrinkage is big, and photopolymerizable reactive is low, it is necessary to bigger exposure dose could solidify.
United States Patent (USP) 4510094 has been reported for work and has been had photoactive platinum group catalyst and prepare mould release for hydrosilylation.How cheap and easy to get containing hydrogen silicone oil kind is, and it is good that Si-H addition reaction product has the transparency, and the features such as high-low temperature resistant color inhibition is outstanding are particularly suitable for touch screen laminating purposes, but only have ultraviolet curing function and can't tackle the defect that dash area does not solidify.
The patent application that publication number is CN103992650A discloses the double; two cured silicone resin combination of a kind of ultraviolet/dampness, this constituent is by percentage to the quality, including 100 parts of silicone terminated polydimethylsiloxane of vinyl alkoxy, 0.1-50 part sulfydryl silicone oil, 0.1-2 part moisture-curable catalyst and 0.1-2 part ultraviolet initiator, but it does not disclose that the storage stability of this constituent is how.The problem easily occurring gel in order to solve fluid sealant when storage, prior art is frequently with adding dehydrant in fluid sealant.Research shows, adds dehydrant and can improve the storge quality of fluid sealant, but make the surface drying time of fluid sealant extend, makes the transparent phase strain differential of fluid sealant simultaneously.
Summary of the invention
It is an object of the invention to provide a kind of storage stability good, optically transparent, can the double; two organic siliconresin constituent solidified of ultraviolet/dampness that solidifies of rapid ultraviolet line.
The technical solution realizing the object of the invention is: the double; two cured silicone resin combination of a kind of ultraviolet/dampness, described constituent by weight percentage, including 100 parts of silicone terminated polydimethylsiloxane of vinyl ketone oximido, 0.1-50 part containing hydrogen silicone oil, 0.1-2 part moisture-curable catalyst and 4 × 10-6-20×10-6Part ultraviolet initiator.
Wherein, the described silicone terminated polydimethylsiloxane of vinyl ketone oximido is structured with:
X1, X2, X3 and X4 represent any one group in methyl, ethyl, butanone oximido, and n is the integer of 100-10000.
X1, X2, X3, X4 are preferably all butanone oximido.
Described containing hydrogen silicone oil is structured with:
R1, R2 represent arbitrary group in methyl, ethyl, propyl group, vinyl, phenyl.R1, R2 can be identical, it is also possible to different.The preferred methyl of R1, R2, m and n is the integer of 4-1000.
By weight percentage, in described containing hydrogen silicone oil, hydrogen content is 0.1-10wt%, it is preferable that 0.2-2wt%.
Described ultraviolet initiator is platinum family acetylacetonate complex, it is preferable that acetylacetone,2,4-pentanedione platinum.
Described moisture-curable catalyst is organo-tin compound, titanate ester compound, α silane coupler, Louis's acids or lewis base compounds, it is preferable that organo-tin compound or titanate ester compound.
Compared with prior art, the invention have the advantage that
1, the transparency is good, it is possible to ultraviolet/dampness is double; two to be solidified.
2, required energy is solidified low, 1500mJ/cm2Namely curable.
3, the double; two cured silicone resin of the ketoxime removing type that the present invention selects, compares the double; two cured silicone resin keeping quality of dealcoholized type better, can preserve 1 year under room temperature；And under equal conditions, the moisture-curable speed of the double; two cured silicone resin of the ketoxime removing type of the present invention is faster than the double; two cured silicone resin of dealcoholized type.
Detailed description of the invention
Below in conjunction with embodiment and comparative example, the present invention is described further.
The present invention provides a kind of optically transparent, can the double; two organic siliconresin constituent solidified of ultraviolet/dampness that solidifies of rapid ultraviolet line.
The double; two organic siliconresin constituent solidified of ultraviolet/dampness is made up of four kinds of compositions, the silicone terminated polydimethylsiloxane of vinyl ketone oximido, containing hydrogen silicone oil cross-linking agent, moisture-curable catalyst and ultraviolet initiator.But the constituent of the present invention is not limited to these four composition, transparent inorganic filler, response type or non-reactive plasticizer, diluent, heat stabilizer, levelling agent, defoamer, thixotropic agent, preservative, light stabilizer etc. can be added as required.
Wherein, the silicone terminated polydimethylsiloxane of vinyl ketone oximido in the present invention is structured with:
X1, X2, X3, X4 represent any one group in methyl, ethyl, butanone oximido, and n is the integer of 100-10000.
X1, X2, X3, X4 are preferably all butanone oximido.
The silicone terminated polydimethylsiloxane of vinyl ketone oximido in the present invention can adopt hydroxyl-terminated injecting two methyl siloxane and vinyl ketone oximino silane coupling agent to react and prepare under catalyst exists, it would however also be possible to employ the silicone terminated polydimethylsiloxane of commercially available vinyl ketone oximido is as the raw material of constituent.
During preparation, vinyl ketone oximino silane coupling agent for terminating can be vinyl tributyl ketoximyl silane coupling agent, can also be vinyl two diacetylmonoxime base silane coupling agent or with methyl three diacetylmonoxime, four diacetylmonoxime mix according to a certain percentage to be made to solidify or moisture-curable speed and crosslink density for adjusting UV.
Containing hydrogen silicone oil structure in the present invention is as follows:
R1, R2 are methyl, and m and n is the integer of 4-1000.Wherein, by weight percentage, in containing hydrogen silicone oil, hydrogen content is 0.1-10wt%, it is preferable that 0.1-2wt%.
Ultraviolet initiator in the present invention is platinum family acetylacetonate complex, the mixing of one or more in the acetylacetonate complex of the metals such as platinum (Pt), palladium (Pd), osmium (Os), iridium (Ir), ruthenium (Ru), rhodium (Rh).
The moisture-curable catalyst that the present invention adopts has five big classes, organo-tin compound, titanate ester compound, α-silane coupler, Louis's acids and lewis base compounds.
Conventional organic tin moisture-curable catalyst includes: dibutyl tin laurate, dibutyltin diacetate, dibutyl tin diethyl hexaoate, two sad dibutyl tins, dimethyl maleic acid dibutyl tin, dibutyitin maleate, dioctyl tin diacetate, distearyl acid dioctyl tin, tin dilaurate dioctyl tin, dimethyl dibutyl tin, two phenoxy group dibutyl tins, dimethoxy dibutyl tin, dibutyl tin diacetyl acetonate, ethyl diacetoacetate dibutyl tin, double, two triethoxy silicic acid dibutyl tins, the product of double, two triethoxy silicic acid dioctyl tins and dialkoxy stannum oxide and silicate compound etc. tetravalent tin compounds；The Bivalent Tin compounds such as tin octoate, aphthenic acids stannum, stearic acid stannum；Three sad Monobutyltins, three isopropoxies but butyl tin etc. but butyl tin or single tin octylate compound, or the one of which of above-mentioned organotin or several mixing.
Conventional titanate ester compound includes: tetra isopropyl titanate, tetra-n-butyl titanate esters, tetra-tert titanate esters, isopropyl three (dioctylphyrophosphoric acid acyloxy) titanate esters, sec.-propyl three (dioctyl phosphoric acid acyloxy) titanic acid ester, isopropyl two oleic acid acyloxy (dioctyl phosphoric acid acyloxy) titanate esters, monoalkoxy unsaturated fatty acid titanate esters, the chelate of Di(dioctylpyrophosphato) ethylene titanate and triethanolamine, Di(dioctylpyrophosphato) ethylene titanate, pyrophosphoric acid type monoalkoxy class titanate esters, two (octyl phenol polyoxyethylene ether) phosphide, tetra isopropyl two (dioctyl phosphito acyloxy) titanate esters, or one or more mixing of above-claimed cpd etc..
Conventional α silane coupler includes: chloromethyl triethoxysilane, dichloromethyl triethoxysilane, Diethylaminomethyl triethoxysilane, Diethylaminomethyl methyldiethoxysilane, second bis aminomethyl triethoxysilane, n-butylaminomethyl triethoxysilane, n-butylaminomethyl methyldiethoxysilane, two n-butylaminomethyl triethoxysilanes, own bis aminomethyl methyldiethoxysilane, hexamethylene diamine ylmethyl triethoxysilane, aminopropyltriethoxysilane triethoxysilane, aminopropyltriethoxysilane trimethoxy silane, aminopropyltriethoxysilane methyldiethoxysilane, methacryloxy triethoxysilane, acetoxyl group amino methyl triethoxysilane, iso-cyanatomethyl triethoxysilane, or one or more mixing of above-mentioned coupling agent.
Conventional lewis acid compound includes: long-chain fatty acid, alkyl benzene sulphonate, acid phosphatase ester type compound, boron trifluoride etherate, boron trifluoride acetic acid complex, boron trifluoride tetrahydrofuran complex, boron trifluoride methanol complex, Boron Trifluoride Ethylamine complex, boron trifluoride acetonitrile complex, boron trifluoride-phenol complex, boron trifluoride p-methyl phenol complex, boron trifluoride benzylamine complex, boron trifluoride methyl ether complex, boron trifluoride ether complex, boric carbonic acid dimethyl ester complex trifluoride or corresponding Boron tribromide, triiodide boron complex, or one or more mixing in above-claimed cpd.Particularly preferably boron trifluoride etherate, Boron Trifluoride Ethylamine complex, boron trifluoride acetonitrile complex, boric carbonic acid dimethyl ester complex trifluoride one or more mixing.
Conventional lewis base compound includes: the primary amines such as propylamine, butylamine, amylamine, hexylamine, octylame, 2 ethyl hexylamine, nonyl amine, decyl amine, dodecyl amine, cetylamine, octadecylamine, cyclohexylamine；The alkyl such as diethylamine, di-n-propylamine, dibutyl amine, diamylamine, didecylamine, two (dodecyl amines), two (cetylamines), two (octadecylamines) replace secondary-amine compound；The aliphatic tertiary amine compounds such as triethylamine, trihexylamine, trioctylamine；The aromatic nitrile base compounds such as dodecyl polyaniline, octadecyl aniline, triphenylamine；Ethanolamine, diethanolamine, triethanolamine, diethyl triamine, trientine, cyclohexylamine, benzyl amine, hexamethylene diamine, guanidine compound, agate beautiful jade compounds, glyoxaline compound, 1,8-diazabicyclo (5,4,0) endecatylene-7(DBU) etc. other ring-type or with replace functional group aminated compounds, or in above-claimed cpd one or more mixing.
The preferred organo-tin compound of moisture-curable catalyst of the present invention and titanate ester compound.
Illustrate below in conjunction with instantiation.
The test of surface drying time adopts GB GB/T13477.5-2002, is a common counter of quantitatively characterizing moisture-curable adhesive solidification speed.Surface drying time is more short, and moisture-curable speed is more fast.
The hardness test of solidfied material adopts Shore-OO durometer.
The double; two concrete formula of organic siliconresin constituent solidified of ultraviolet/dampness of the present invention is as follows:
【Example-1] polydimethylsiloxanes resin 100 parts silicone terminated for vinyl two butanone oximido that viscosity is 1000mPas is added in planetary mixer, add 2 parts of containing hydrogen silicone oils (in containing hydrogen silicone oil, hydrogen content is 2.0wt%) and stir.Add 4 × 10-6Part acetylacetone,2,4-pentanedione platinum, 0.5 part of tetra-tert titanate esters, stirs 30min under vacuum conditions, is filled in 330ml silica gel bucket and takes care of, then carry out the hardness test after surface drying time, UV solidification, moisture-curable and double; two solidification.
【Example 2-10] same to example-1 of preparation method, formula and physical property are in Table 1 and 2.
【Comparative example 1] polydimethylsiloxanes resin 100 parts silicone terminated for vinyl two butanone oximido that viscosity is 1000mPas is added in planetary mixer, 2 parts of containing hydrogen silicone oils (hydrogen content 2.0%), 0.5 part of tetra-tert titanate esters, without acetylacetone,2,4-pentanedione platinum, stir 30min under vacuum conditions, it is filled in 330ml silica gel bucket and takes care of, then carry out the hardness test after surface drying time, UV solidification, moisture-curable and double; two solidification.
【Comparative example 2-5] same to comparative example-1 of preparation method, formula and physical property are in Table-3.
Table-1
Table-2
Table-3
| Comparative example-1 | Comparative example-2 | Comparative example-3 | Comparative example-4 | Comparative example-5 | |
| The silicone terminated polydimethylsiloxane viscosity 1000mPas of vinyl two butanone oximido | 100 | 100 | |||
| The silicone terminated polydimethylsiloxane viscosity 10000mPas of vinyl two butanone oximido | 100 | 100 | |||
| The silicone terminated polydimethylsiloxane viscosity 80000mPas of vinyl two butanone oximido | 100 | ||||
| Containing hydrogen silicone oil (hydrogen content 2.0%) | 2 | 1 | |||
| Containing hydrogen silicone oil (hydrogen content 0.76%) | 6 | 4 | |||
| Containing hydrogen silicone oil (hydrogen content 0.1%) | 20 | ||||
| Acetylacetone,2,4-pentanedione platinum | 10×10-6Part | ||||
| Acetylacetone,2,4-pentanedione rhodium | 4×10-6Part | ||||
| Palladium acetylacetonate | 10×10-6Part | ||||
| Tetra-tert titanate esters | 0.5 | ||||
| Tetra-n-butyl titanate esters | 2 | ||||
| Dibutyl tin laurate | |||||
| Outward appearance | Transparent | Transparent | Transparent | Transparent | Transparent |
| Surface drying time (min) | 12 | Do not solidify | Do not solidify | Do not solidify | 17 |
| UV irradiates 1500mJ/cm2Hardness Shore-OO | Do not solidify | 58 | 45 | 30 | Do not solidify |
| Independent moisture-curable (25 degree, 50%RH*7 days) hardness | 47 | Do not solidify | Do not solidify | Do not solidify | 42 |
| UV+ moisture-curable (25 degree, 50%RH*7 days) hardness | 49 | 60 | 49 | 34 | 48 |
The vinyl two butanone silicone terminated polydimethylsiloxane of oximido that embodiment 1 adopts viscosity to be 1000mPas, containing hydrogen silicone oil, ultraviolet initiator acetylacetone,2,4-pentanedione platinum, tetra-tert titanate esters, water white transparency can be obtained, there is UV curable and moisture-curable gets both double; two solidifies constituents, it is possible to solving dash area preferably can not the problem that solidifies of UV.It is relatively low that UV solidifies required exposure dose, drastically increases production efficiency.
Embodiment 2-10 adopts the polydimethylsiloxane of different viscosities ketoxime base end-blocking, and different containing hydrogen silicone oils and different catalyst respectively obtain has a UV curable and moisture-curable gets both double; two solidifies constituents.
As a comparison, comparative example 1 and comparative example 5 give the constituent without ultraviolet initiator, although the two constituent can moisture-curable, but all can not carry out UV solidification.Comparative example 2-4 gives the constituent without moisture-curable catalyst, although these constituents can carry out UV solidification, but does not have moisture-curable.
Claims (10)
1. the double; two cured silicone resin combination of ultraviolet/dampness, it is characterized in that, described constituent by weight percentage, including 100 parts of silicone terminated polydimethylsiloxane of vinyl ketone oximido, 0.1-50 part containing hydrogen silicone oil, 0.1-2 part moisture-curable catalyst and 4 × 10-6-20×10-6Part ultraviolet initiator.
2. the double; two cured silicone resin combination of ultraviolet/dampness according to claim 1, it is characterised in that the described silicone terminated polydimethylsiloxane of vinyl ketone oximido is structured with:
,
X1, X2, X3 and X4 represent any one group in methyl, ethyl, butanone oximido, and n is the integer of 100-10000.
3. the double; two cured silicone resin combination of ultraviolet/dampness according to claim 2, it is characterised in that: X1, X2, X3, X4 are all butanone oximido.
4. the double; two cured silicone resin combination of ultraviolet/dampness according to claim 1, it is characterised in that described containing hydrogen silicone oil is structured with:
,
R1, R2 represent arbitrary group in methyl, ethyl, propyl group, vinyl, phenyl, and m and n is the integer of 4-1000.
5. the double; two cured silicone resin combination of ultraviolet/dampness according to claim 4, it is characterised in that R1, R2 are methyl.
6. the double; two cured silicone resin combination of ultraviolet/dampness according to claim 1 or 4, it is characterised in that in described containing hydrogen silicone oil, hydrogen content is 0.1-10wt%.
7. the double; two cured silicone resin combination of ultraviolet/dampness according to claim 1 or 4, it is characterised in that in described containing hydrogen silicone oil, hydrogen content is 0.1-2.0wt%.
8. the double; two cured silicone resin combination of ultraviolet/dampness according to claim 1, it is characterised in that described ultraviolet initiator is platinum family acetylacetonate complex.
9. the double; two cured silicone resin combination of ultraviolet/dampness according to claim 1, it is characterised in that described ultraviolet initiator is acetylacetone,2,4-pentanedione platinum.
10. the double; two cured silicone resin combination of ultraviolet/dampness according to claim 1, it is characterised in that described moisture-curable catalyst is organo-tin compound, titanate ester compound, α silane coupler, Louis's acids or lewis base compounds.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107674640A (en) * | 2017-09-21 | 2018-02-09 | 深圳市新纶科技股份有限公司 | A kind of ultraviolet curing organic silicon optics of liquids glue composition and preparation method thereof |
| CN113604190A (en) * | 2021-08-11 | 2021-11-05 | 佛山(华南)新材料研究院 | Ultraviolet-curing heat-conducting pouring sealant and preparation method and application thereof |
| CN115433540A (en) * | 2022-09-28 | 2022-12-06 | 江苏矽时代材料科技有限公司 | Photo-thermal curing organic silicon LOCA adhesive and preparation method and application thereof |
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| CN101511943A (en) * | 2006-08-30 | 2009-08-19 | Sika技术股份公司 | Silicone composition |
| CN103992650A (en) * | 2014-04-11 | 2014-08-20 | 郝建强 | Ultraviolet ray/wet gas double curing organosilicon resin composition |
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| CN101511943A (en) * | 2006-08-30 | 2009-08-19 | Sika技术股份公司 | Silicone composition |
| CN103992650A (en) * | 2014-04-11 | 2014-08-20 | 郝建强 | Ultraviolet ray/wet gas double curing organosilicon resin composition |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107674640A (en) * | 2017-09-21 | 2018-02-09 | 深圳市新纶科技股份有限公司 | A kind of ultraviolet curing organic silicon optics of liquids glue composition and preparation method thereof |
| CN107674640B (en) * | 2017-09-21 | 2020-06-05 | 深圳市新纶科技股份有限公司 | Ultraviolet-curing organic silicon liquid optical adhesive composition and preparation method thereof |
| CN113604190A (en) * | 2021-08-11 | 2021-11-05 | 佛山(华南)新材料研究院 | Ultraviolet-curing heat-conducting pouring sealant and preparation method and application thereof |
| CN113604190B (en) * | 2021-08-11 | 2023-11-24 | 佛山(华南)新材料研究院 | Ultraviolet light curing type heat conduction pouring sealant and preparation method and application thereof |
| CN115433540A (en) * | 2022-09-28 | 2022-12-06 | 江苏矽时代材料科技有限公司 | Photo-thermal curing organic silicon LOCA adhesive and preparation method and application thereof |
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