CN105754541B - The double cured silicone resin combinations of ultraviolet light/moisture - Google Patents
The double cured silicone resin combinations of ultraviolet light/moisture Download PDFInfo
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Abstract
The invention discloses a kind of double cured silicone resin combinations of ultraviolet light/moisture.The constituent by weight percentage, including 100 parts, 0.1-50 parts of containing hydrogen silicone oils, 0.1-2 parts of moisture-curable catalyst and 4-20 × 10‑6Part ultraviolet initiator.The double cured silicone resin combination transparencys of ultraviolet light/moisture of the invention are good, can be with the double solidifications of ultraviolet light/moisture；And the energy needed for solidifying is low, 1500mJ/cm2It is i.e. curable.The double cured silicone resins of the ketoxime removing type that the present invention selects, it is more preferable compared to the double cured silicone resin keeping qualities of dealcoholized type, it can be saved under room temperature 1 year；And under equal conditions, the moisture-curable speed of the double cured silicone resins of ketoxime removing type of the invention cured silicone resins more double than dealcoholized type are fast.
Description
Technical field
The invention belongs to optical adhesive/sealant preparation fields, and in particular to one kind is optically transparent, it is ultraviolet to have
The double cured organic siliconresin constituents of line/moisture.
Background technique
Smart phone and plate market, which mostly use, at present directly fits technology (Direct Bonding or full
Lamination) gap between LCM and touched panel glass is eliminated.Many touch panel factories practise when carrying out glass gluing
It is used to use the optical adhesive tape OCA(Optical Clear Adhesive that production efficiency is higher, thickness is uniform) coating technique, but this
Technology is easy to produce bubble and increases fraction defective in fitting, and when being bonded the micro-bubble that can not find also may with when
Between and expand.Bubble removing problem will affect outside yield, and since optical adhesive tape (OCA) cannot be reprocessed, faulty materials mostly can only
It scraps, cause productivity effect low and increases fitting factory's cost pressure.
Compared to OCA, ultraviolet curing optics of liquids transparent resin LOCA(Liquid Optical Clear Adhesive)
It since abutted equipment is simple, can reprocess, be easy deaeration, the features such as the cost of material is low, by more and more touch-control factories
The welcome of family.But simultaneously because touch panel frame portion is printed with lighttight ink, ultraviolet light cannot be irradiated through ink
To these places, to generate uncured region, these regions, which need to be additionally carried out side light source irradiation, just can ensure that completion of cure,
Equipment cost is considerably increased, production efficiency is reduced.
Aiming at the problem that shadow region is unable to ultraviolet curing, the patent of invention of Publication No. CN102925062A is proposed
A kind of double cured optics of liquids transparent resins of ultraviolet light/heating, solve touch panel frame portion and are unable to ultraviolet curing
Problem, but increase heat curing process, production efficiency is not improved still.
Henkel Corp, the U.S. in 2005 discloses a kind of quick moisture-curable and UV- moisture dual cure compositions are (public
The number of opening is CN1705684A).Provided composition contains the α-carbon for being keyed to silicon atom, and reactivity is strong, moisture-curable speed
Degree is fast, and structure is as follows:
It is bonded using the ultraviolet light/moisture double cured resin of the invention, touch panel light transmission part can carry out purple
Outside line solidification, frame portion can be substantially increased by the moisture-curable in air without increasing additional heating equipment
Production efficiency.Although moisture-curable speed is quickly, due to ultraviolet curing mechanism be by methacryl functional group from
It is polymerize by base, photopolymerizable reactive is low, needs biggish exposure dose that could solidify.In addition free radical polymerization system cure shrinkage
Greatly, cause to generate larger stress when solidification, be unsuitable for the fitting purposes of large scale touch screen.
Beijing University of Chemical Technology Zhang Junying in 2012 also disclose a kind of dual-curable polysiloxane acrylate resin and its
Preparation method (Publication No. CN102408569A).In N2Under protection, by hydroxyl-terminated injecting two methyl siloxane and methacryl
The mixing of oxygroup propyl trimethoxy silicane, is added solvent and catalyst, ester exchange reaction obtain pre-product.Revolving removes solvent,
Obtain mixture.At room temperature, it is extracted with anhydrous methanol, is centrifuged and removes solvent, obtaining can double solidification polysiloxanes third
Alkene acid ester resin.As the patent of Henkel Corp, the U.S., ultraviolet curing mechanism is by methacryl functional group
Free radical polymerization, cure shrinkage is big, and photopolymerizable reactive is low, needs biggish exposure dose that could solidify.
United States Patent (USP) 4510094 registered have photoactive platinum group catalyst for hydrosilylation prepare it is release
Agent.The features such as how cheap and easy to get containing hydrogen silicone oil type is, and Si―H addition reaction product has the transparency good, and high-low temperature resistant color inhibition is outstanding is special
It is not suitable for touch screen fitting purposes, but it is not cured scarce only to have the function of that ultraviolet curing can't cope with dash area
It falls into.
The patent application of Publication No. CN103992650A discloses a kind of double cured silicone resin groups of ultraviolet light/moisture
At object, the constituent by percentage to the quality, including the silicone terminated dimethyl silicone polymer of 100 parts of vinyl alkoxies, 0.1-50
Part sulfydryl silicone oil, 0.1-2 parts of moisture-curable catalyst and 0.1-2 parts of ultraviolet initiators, but it does not disclose that the constituent
How is storage stability.In order to solve the problems, such as that sealant is easy to appear gel in storage, the prior art is frequently with sealing
Dehydrating agent is added in glue.Studies have shown that addition dehydrating agent can improve the storge quality of sealant, but make the surface drying of sealant
Time extends, while making the transparent phase strain differential of sealant.
Summary of the invention
That the object of the present invention is to provide a kind of storage stabilities is good, optically transparent, can rapid ultraviolet line it is cured ultraviolet
The double cured organic siliconresin constituents of line/moisture.
Realizing the technical solution of the object of the invention is: a kind of double cured silicone resin combinations of ultraviolet light/moisture,
The constituent by weight percentage, including the silicone terminated dimethyl silicone polymer of 100 parts of vinyl ketone oximidos, 0.1-50 parts contain
Hydrogen silicone oil, 0.1-2 parts of moisture-curable catalyst and 4 × 10-6-20×10-6Part ultraviolet initiator.
Wherein, the silicone terminated dimethyl silicone polymer of vinyl ketone oximido has the following structure:
X1, X2, X3 and X4 represent methyl, ethyl, any one group in butanone oximido, and n is the integer of 100-10000.
X1, X2, X3, X4 are preferably all butanone oximido.
The containing hydrogen silicone oil has the following structure:
R1, R2 represent methyl, ethyl, propyl, vinyl, any group in phenyl.R1, R2 can be identical, can also not
Together.The preferred methyl of R1, R2, m and n are the integer of 4-1000.
By weight percentage, hydrogen content is 0.1-10wt%, preferably 0.2-2wt% in the containing hydrogen silicone oil.
The ultraviolet initiator is platinum family acetylacetonate complex, preferably acetylacetone,2,4-pentanedione platinum.
The moisture-curable catalyst is organo-tin compound, titanate ester compound, α silane coupling agent, lewis acid
Class or Louis's alkaloid compound, preferably organo-tin compound or titanate ester compound.
Compared with prior art, the invention has the advantages that
1, the transparency is good, can be with the double solidifications of ultraviolet light/moisture.
2, the energy needed for solidifying is low, 1500mJ/cm2It is i.e. curable.
3, the double cured silicone resins of the ketoxime removing type that the present invention selects are saved compared to the double cured silicone resins of dealcoholized type
Property is more preferable, can save under room temperature 1 year；And under equal conditions, ketoxime removing type of the invention double cured silicone resins
Moisture-curable speed cured silicone resins more double than dealcoholized type are fast.
Specific embodiment
The present invention is described further below in conjunction with embodiment and comparative example.
The present invention provide it is a kind of optically transparent, can the double cured organosilicons of the cured ultraviolet light/moisture of rapid ultraviolet line
Resin combination.
The double cured organic siliconresin constituents of ultraviolet light/moisture are made of four kinds of ingredients, and vinyl ketone oximido is silicone terminated
Dimethyl silicone polymer, containing hydrogen silicone oil crosslinking agent, moisture-curable catalyst and ultraviolet initiator.But constituent of the invention
Be not limited to these four ingredients, can add as needed transparent inorganic filler, response type or non-reactive plasticizer, diluent,
Heat stabilizer, levelling agent, defoaming agent, thixotropic agent, preservative, light stabilizer etc..
Wherein, the silicone terminated dimethyl silicone polymer of vinyl ketone oximido in the present invention has the following structure:
X1, X2, X3, X4 represent methyl, ethyl, any one group in butanone oximido, and n is the integer of 100-10000.
X1, X2, X3, X4 are preferably all butanone oximido.
The silicone terminated dimethyl silicone polymer of vinyl ketone oximido in the present invention can use terminal hydroxy group polydimethylsiloxanes
Alkane and vinyl ketone oximino silane coupling agent are reacted in the presence of catalyst to prepare, and can also use commercially available vinyl ketone oximido
Raw material of the silicone terminated dimethyl silicone polymer as constituent.
When preparation, the vinyl ketone oximino silane coupling agent for sealing end can be vinyl tributyl ketoximyl silane coupling
Agent, be also possible to two butanone oximino silane coupling agent of vinyl or with three diacetylmonoxime of methyl, four diacetylmonoximes are according to a certain percentage
It is used in mixed way to adjust UV solidification or moisture-curable speed and crosslink density.
Containing hydrogen silicone oil structure in the present invention is as follows:
R1, R2 are methyl, the integer that m and n are 4-1000.Wherein, by weight percentage, hydrogen content in containing hydrogen silicone oil
For 0.1-10wt%, preferably 0.1-2wt%.
Ultraviolet initiator in the present invention is platinum family acetylacetonate complex, is selected from platinum (Pt), palladium (Pd), osmium
(Os), mixing one or more of in the acetylacetonate complex of metals such as iridium (Ir), ruthenium (Ru), rhodium (Rh).
The moisture-curable catalyst that the present invention uses has five major class, and organo-tin compound, titanate ester compound, α-silane are even
Join agent, Louis's acids and Louis's alkaloid compound.
Common organic tin moisture-curable catalyst includes: dibutyl tin dilaurate, dibutyltin diacetate, diethyl
Caproic acid dibutyl tin, two sad dibutyl tins, dimethyl maleic acid dibutyl tin, dibutyitin maleate, oxalic acid dioctyl
Tin, distearyl acid dioctyl tin, tin dilaurate dioctyl tin, dimethyl dibutyl tin, two phenoxy group dibutyl tins, dimethoxy
It is dibutyl tin, dibutyl tin diacetyl acetonate, ethyl diacetoacetate dibutyl tin, double triethoxy silicic acid dibutyl tins, double
Reaction product of triethoxy silicic acid dioctyl tin and dialkoxy tin oxide and silicate compound etc. tetravalent tin class
Close object；The divalent tin compounds such as tin octoate, aphthenic acids tin, stearic acid tin；Three sad Monobutyltins, three isopropoxies but butyl
One of or several mixing of tin etc. but butyl tin or single octyl tin compound or above-mentioned organotin.
Common titanate ester compound includes: tetra isopropyl titanate, tetra-n-butyl titanate esters, tetra-tert metatitanic acid
Ester, isopropyl three (dioctylphyrophosphoric acid acyloxy) titanate esters, isopropyl three (dioctyl phosphoric acid acyloxy) titanate esters, isopropyl
Two oleic acid acyloxy (dioctyl phosphoric acid acyloxy) titanate esters, monoalkoxy unsaturated fatty acid titanate esters, bis- (two octyloxies are burnt
It is phosphate-based) chelate, Di(dioctylpyrophosphato) ethylene titanate, the pyrophosphoric acid of ethylene titanate esters and triethanolamine
Type monoalkoxy class titanate esters, two (octyl phenol polyoxyethylene ether) phosphides, (the dioctyl phosphito acyl-oxygen of tetra isopropyl two
Base) titanate esters or one or more of mixing of above compound etc..
Common α silane coupling agent includes: chloromethyl triethoxysilane, dichloromethyl triethoxysilane, diethylamino
Ylmethyl triethoxysilane, Diethylaminomethyl methyldiethoxysilane, second bis aminomethyl triethoxysilane, positive fourth
Amino methyl 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,
One kind or several of acetoxyl group amino methyl triethoxysilane, iso-cyanatomethyl triethoxysilane or above-mentioned coupling agent
Kind mixing.
Common lewis acid compound includes: long chain fatty acids, alkyl benzene sulphonate, acid phosphatase esters compound, three
It is fluorinated diethyl etherate, boron trifluoride acetic acid complex compound, boron trifluoride tetrahydrofuran complex compound, boron trifluoride methanol complexing
Object, Boron Trifluoride Ethylamine complex compound, boron trifluoride acetonitrile complex compound, boron trifluoride-phenol complex, boron trifluoride are to methyl
Phenol complexes, boron trifluoride benzylamine complex compound, boron trifluoride methyl ether complex compound, boron trifluoride ether complex, boron trifluoride
One or more of carbonic acid dimethyl ester complex or corresponding Boron tribromide, triiodide boron complex or above compound
Mixing.Particularly preferred boron trifluoride etherate, Boron Trifluoride Ethylamine complex compound, boron trifluoride acetonitrile complex compound, trifluoro
Change the mixing of boron carbonic acid dimethyl ester complex one or more.
Common lewis base compound includes: propylamine, butylamine, amylamine, hexylamine, octylame, 2 ethyl hexylamine, nonyl amine, the last of the ten Heavenly stems
The primary amino-compounds such as amine, dodecyl amine, cetylamine, octadecylamine, cyclohexylamine；Diethylamine, di-n-propylamine, dibutyl amine, diamylamine,
The alkyl such as didecylamine, two (dodecyl amines), two (cetylamines), two (octadecylamines) replace secondary-amine compound；Triethylamine, three
The aliphatic tertiary amines class compound such as hexylamine, trioctylamine；The aromatic nitrile bases such as dodecyl polyaniline, octadecyl aniline, triphenylamine
Class compound；Ethanol amine, diethanol amine, triethanolamine, diethyl triamine, trientine, cyclohexylamine, benzyl amine, six methylenes
Base diamines, guanidine compound, Ma beautiful jade class compound, glyoxaline compound, 1,8- diazabicyclo (5,4,0) endecatylene -7
(DBU) etc. other cyclic annular or one or more of the aminated compounds with substituted functional group or above compound mixing.
The preferred organo-tin compound of moisture-curable catalyst of the invention and titanate ester compound.
It is illustrated below with reference to specific example.
The test of surface drying time uses national standard GB/T 13477.5-2002, is the solidification of quantitatively characterizing moisture-curable adhesive
One common counter of speed.Surface drying time is shorter, and moisture-curable speed is faster.
The hardness test of solidfied material uses Shore-OO hardometer.
The double cured organic siliconresin constituent specific formulas of ultraviolet light/moisture of the present invention are as follows:
[example -1] polydimethylsiloxanes resin 100 that viscosity is silicone terminated for the two butanone oximido of vinyl of 1000mPas
Part is added in planetary mixer, and 2 parts of containing hydrogen silicone oils (hydrogen content is 2.0wt% in containing hydrogen silicone oil) are added and stir evenly.It is added 4
×10-6Part acetylacetone,2,4-pentanedione platinum, 0.5 part of tetra-tert titanate esters stir 30min under vacuum conditions, are filled to 330ml silica gel bucket
Then middle keeping carries out surface drying time, UV solidifies, the hardness test after moisture-curable and double solidifications.
The same example -1 of [example 2-10] preparation method, formula and physical property are shown in Table 1 and 2.
[comparative example 1] polydimethylsiloxanes resin that viscosity is silicone terminated for the two butanone oximido of vinyl of 1000mPas
100 parts are added in planetary mixer, and 2 parts of containing hydrogen silicone oils (hydrogen content 2.0%), 0.5 part of tetra-tert titanate esters do not add second
Acyl acetone platinum, stirs 30min under vacuum conditions, is filled in 330ml silica gel bucket and takes care of, and it is solid then to carry out surface drying time, UV
Change, the hardness test after moisture-curable and double solidifications.
The same comparative example -1 of [comparative example 2-5] preparation method, formula and physical property are shown 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 dimethyl silicone polymer viscosity 1000mPas of two butanone oximido of vinyl | 100 | 100 | |||
| The silicone terminated dimethyl silicone polymer viscosity 10000mPas of two butanone oximido of vinyl | 100 | 100 | |||
| The silicone terminated dimethyl silicone polymer viscosity 80000mPas of two butanone oximido of vinyl | 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 dilaurate | |||||
| Appearance | It is transparent | It is transparent | It is transparent | It is transparent | It is 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 |
Embodiment 1 uses viscosity for the silicone terminated dimethyl silicone polymer of two butanone oximido of vinyl of 1000mPas, hydrogeneous
Silicone oil, ultraviolet initiator acetylacetone,2,4-pentanedione platinum, tetra-tert titanate esters, it is available colorless and transparent, have UV curability and
Double solidification constituents that moisture-curable gets both can preferably solve the problems, such as that dash area is unable to UV solidification.UV solidifies institute
The exposure dose needed is lower, greatly improves production efficiency.
Embodiment 2-10 uses the dimethyl silicone polymer of different viscosities ketoxime base sealing end, different containing hydrogen silicone oils and difference
Catalyst respectively obtain the double solidification constituents to get both with UV curability and moisture-curable.
As a comparison, comparative example 1 and comparative example 5 give the constituent for not adding ultraviolet initiator, the two groups
Although at object can moisture-curable, not can be carried out UV solidification.Comparative example 2-4, which gives, does not add moisture-curable catalyst
Constituent does not all have moisture-curable although these constituents can carry out UV solidification.
Claims (5)
1. a kind of double cured silicone resin combinations of ultraviolet light/moisture, it is characterised in that: the constituent is with parts by weight
Meter, including the silicone terminated dimethyl silicone polymer of 100 parts of vinyl ketone oximidos, 0.1-50 parts of containing hydrogen silicone oils, 0.1-2 parts of moisture-curables
Catalyst and 4 × 10-6-20×10-6Part ultraviolet initiator；
Wherein, the silicone terminated dimethyl silicone polymer of vinyl ketone oximido has the following structure:
,
X1、X2、X3And X4Methyl, ethyl, any one group in butanone oximido are represented, n is the integer of 100-10000；
The containing hydrogen silicone oil has the following structure:
,
R1、R2Represent methyl, ethyl, propyl, vinyl, any group in phenyl, the integer that m and n are 4-1000；
Hydrogen content is 0.1-10wt% in the containing hydrogen silicone oil；
The ultraviolet initiator is platinum family acetylacetonate complex；
The moisture-curable catalyst be organo-tin compound, titanate ester compound, α-silane coupling agent, Louis's acids or
Louis's alkaloid compound.
2. the double cured silicone resin combinations of ultraviolet light/moisture according to claim 1, it is characterised in that: X1、X2、
X3、X4It is all butanone oximido.
3. the double cured silicone resin combinations of ultraviolet light/moisture according to claim 1, it is characterised in that: R1、R2For
Methyl.
4. the double cured silicone resin combinations of ultraviolet light/moisture according to claim 1, it is characterised in that: described
Hydrogen content is 0.1-2.0wt% in containing hydrogen silicone oil.
5. the double cured silicone resin combinations of ultraviolet light/moisture according to claim 1, it is characterised in that: described
Ultraviolet initiator is acetylacetone,2,4-pentanedione platinum.
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| 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 |
| 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 |
| CN115433540B (en) * | 2022-09-28 | 2023-07-28 | 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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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