CN103031105A - Ultraviolet curing liquid optical clear adhesive and preparation method thereof - Google Patents
Ultraviolet curing liquid optical clear adhesive and preparation method thereof Download PDFInfo
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- CN103031105A CN103031105A CN2012105762341A CN201210576234A CN103031105A CN 103031105 A CN103031105 A CN 103031105A CN 2012105762341 A CN2012105762341 A CN 2012105762341A CN 201210576234 A CN201210576234 A CN 201210576234A CN 103031105 A CN103031105 A CN 103031105A
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Abstract
The invention relates to an ultraviolet curing liquid optical clear adhesive and a preparation method thereof, and belongs to the field of bonding adhesives. The method comprises the steps that toluene diisocyanate, polyethylene glycol and hydroxyethyl acrylate are taken as raw materials; a urethane acrylate prepolymer is synthesized through polystep reaction by a bulk method; the prepolymer is taken as a main body; a photoinitiator, a composite reactive diluent and other assistants are added; and then the ultraviolet curing liquid optical clear adhesive is prepared. The ultraviolet curing liquid optical clear adhesive prepared by the preparation method has the characteristics that the ultraviolet curing liquid optical clear adhesive is low in smell, moderate in viscosity, good in flexibility, high in light transmittance and refractive index, high in bonding strength, waterproof, and good in cold and heat shock resistance, weather resistance and ageing resistance. The ultraviolet curing liquid optical clear adhesive is completely transparent after being cured, and can keep stable high transparency and is free from yellowing, whitening and degumming for a long term in high-temperature and high-humidity environments.
Description
Technical field
The present invention relates to adhesive area, especially relate to a kind of preparation method of ultraviolet light polymerization liquid optical cement.
Background technology
Ultraviolet light polymerization liquid optical cement (Liquid Optical Clear Adhesive, LOCA) also claims optics UV glue or ultraviolet photo-curing glue, and it is a kind of single-component, medium viscosity, high-clarity ultraviolet photo-curing tackiness agent.
The ultraviolet light polymerization liquid optical cement is the special adhesive for optically transparent component, is a capacitance plate glue of new generation of developing along with the needs of modern electronic product development that is applied in.The electronic product that the hyundai electronics industry is produced all is to frivolous future development, and traditional technique for sticking has not satisfied the needs of modern electronic product development, and modern glue industry must be immediately following the paces of electron trade development.The ultraviolet light polymerization liquid optical cement is that wherein a electron trade display screen of complying with is made the glue of new generation that production is researched and developed.Made improvement at original used optics adhesive tape.For example: transmissivity has reached more than 99%, and yellowness index is less than 0.4 etc.
The characteristics of ultraviolet light polymerization liquid optical cement are: after the applying glue, just curable in the several minutes under the uviolizing of certain wavelength.Have water white transparency, transmittance is more than 99%, and bonding strength is good, can solidify under normal temperature or medium temperature condition, and it is little to have simultaneously a cure shrinkage the soft characteristic of anti-xanthochromia hardness, and the characteristics such as can do over again.Compare with traditional optical cement (OCA) adhesive tape, the ultraviolet light polymerization liquid optical cement has special advantage in some Application Areas, can solve the limitation that traditional optical glue (OCA) adhesive tape faces.
Yet domestic research and development application facet at the ultraviolet light polymerization liquid optical cement is also relatively backward at present: be in particular in aspect following two:
1) only there are several companies to produce the UV cured adhesive in the at home hundreds of adhesive producing unit, though some research is reported in the literature, produce seldom but really move towards the industrialization, so its course of industrialization remains development research, industrial scale remains to be enlarged.
2) research of domestic UV cured adhesive is started late, the fields such as research, exploitation, production, application with larger gap is abroad all arranged, thereby also need strengthen dynamics and the degree of depth of research and development to this field that is full of glamour.
Summary of the invention
For the deficiencies in the prior art, problem to be solved by this invention be propose a kind ofly to have that smell is low, modest viscosity, ultraviolet light polymerization liquid optical cement that snappiness is good.
For solving the problems of the technologies described above, the technical solution used in the present invention is:
A kind of preparation method of ultraviolet light polymerization liquid optical cement comprises the steps:
A) in reaction vessel, add tolylene diisocyanate, under 20~25 ℃ of conditions of normal temperature, stirring velocity is under 80~100 rev/mins the condition, polyoxyethylene glycol is splashed into reaction vessel, be warming up to 35~45 ℃, insulation certain hour t, the mass ratio of described tolylene diisocyanate and described polyoxyethylene glycol is 0.95:1;
B) after t=3 hour, drip mass ratio and be 32.5% Hydroxyethyl acrylate reaction, add simultaneously mass percent and be 0.1% stopper, be warmed up to 65~70 ℃ after the adding, insulation reaction 4 hours;
C) temperature is down to 50 ℃ in the question response container, adds mass percent and be 0.5% dehydrated alcohol reaction 20 minutes, and suction filtration namely gets polyurethane acrylate prepolymer;
D) described polyurethane acrylate prepolymer is cooled to 20~25 ℃, stir with the free radical activity thinner, add successively softening agent, light trigger and other auxiliary agents, stir 1~2h, until after described softening agent, described light trigger and other auxiliary agents dissolved fully, resulting product was described ultraviolet light polymerization liquid optical cement finished product.
Preferably, containing mass percent among the described step b in the Hydroxyethyl acrylate is 0.08% catalyzer dibutyl tin laurate.
Preferably, described stopper is Resorcinol.
Preferably, described free radical activity thinner is Hydroxyethyl acrylate, tripropylene glycol double methacrylate, Viscoat 295, propoxylation glycerol triacrylate, 1, one or more in 6-hexylene glycol methoxyl group mono acrylic ester, the ethoxylation neopentyl glycol methoxyl group mono acrylic ester.
Preferably, described softening agent is dibutyl phthalate or dioctyl phthalate (DOP).
Preferably; described light trigger is benzophenone, two (2; 4; the 6-trimethylbenzoyl) phenyl phosphine oxide, 2-methyl isophthalic acid-[4-(methyl sulfo-) phenyl]-2-(4-morpholinyl)-1-acetone, 1-hydroxy-cyclohexyl phenyl ketone, 2; 4,6-trimethylbenzoyl phenyl-phosphonic acid ethyl ester, 2-hydroxy-2-methyl-1-phenyl-1-acetone, 2-benzyl-2-dimethylamino-1-(4-morpholinyl phenyl)-in the 1-butanone one or more.
Preferably, described other auxiliary agents comprise coupling agent and oxidation inhibitor, described coupling agent is γ-methacryloxypropyl trimethoxy silane, γ-aminopropyl triethoxysilane or N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, described oxidation inhibitor is 2,6 ditertiary butyl p cresol.
A kind of ultraviolet light polymerization liquid optical cement by mass percentage, comprises following component: polyurethane acrylate prepolymer 30%~45%, free radical activity thinner 40%~55%, softening agent 10%~15%, light trigger 2%~6%, other auxiliary agents.
Preferably, described free radical activity thinner is Hydroxyethyl acrylate, tripropylene glycol double methacrylate, Viscoat 295, propoxylation glycerol triacrylate, 1, one or more in 6-hexylene glycol methoxyl group mono acrylic ester, the ethoxylation neopentyl glycol methoxyl group mono acrylic ester; Described softening agent is dibutyl phthalate or dioctyl phthalate (DOP); Light trigger is benzophenone, two (2; 4; the 6-trimethylbenzoyl) phenyl phosphine oxide, 2-methyl isophthalic acid-[4-(methyl sulfo-) phenyl]-2-(4-morpholinyl)-1-acetone, 1-hydroxy-cyclohexyl phenyl ketone, 2; 4,6-trimethylbenzoyl phenyl-phosphonic acid ethyl ester, 2-hydroxy-2-methyl-1-phenyl-1-acetone, 2-benzyl-2-dimethylamino-1-(4-morpholinyl phenyl)-in the 1-butanone one or more.
Preferably, described other auxiliary agents comprise coupling agent and oxidation inhibitor, described coupling agent is γ-methacryloxypropyl trimethoxy silane, γ-aminopropyl triethoxysilane or N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, described oxidation inhibitor is 2,6 ditertiary butyl p cresol.
The invention has the beneficial effects as follows: the prepared ultraviolet light polymerization liquid optical cement of the present invention has that smell is low, modest viscosity, snappiness are good, have good transmittance and specific refractory power, bonding strength is high, the characteristics such as water-fast, cold-hot impact, weathering resistance, ageing resistance are good; Fully transparent after the curing, but product stable for extended periods of time height under high temperature, high humidity environment is transparent, not xanthochromia, not albefaction, degumming phenomenon not.
Embodiment
Example of the present invention is can not limit the present invention to explanation of the present invention, in the implication suitable with the present invention and any change and the adjustment in the scope, all should think within the scope of the invention.
The present invention will be further described below in conjunction with embodiment.
Embodiment 1
Step 1; the preparation of polyurethane acrylate prepolymer: comprise the steps: in the four-hole boiling flask that agitator, thermometer, prolong and constant pressure funnel are housed, to add tolylene diisocyanate; logical nitrogen protection; be under 80~100 rev/mins the condition in 20~25 ℃ of normal temperature, stirring velocity; from constant pressure funnel, slowly drip polyoxyethylene glycol; after dropwising; slowly heat up; temperature of reaction is controlled at 35~45 ℃, and the mass ratio of the total described tolylene diisocyanate of control and described polyoxyethylene glycol is 0.95:1 in composition of raw materials.After the insulation reaction 3 hours, drip gradually mass ratio and be 32.5% Hydroxyethyl acrylate reaction, add simultaneously 0.1% stopper, be warmed up to gradually 65-70 ℃ after dripping off, reacted approximately 4 hours.When treating that temperature is down to 50 ℃ in the described four-hole boiling flask, added mass percent and be 0.5% dehydrated alcohol reaction 20 minutes, suction filtration namely gets described polyurethane acrylate prepolymer (PUA).After the polyurethane acrylate prepolymer that makes is cooled to room temperature, place the encloses container lucifuge to store.
In the process of synthesis of polyurethane acrylic ester prepolymer, because-the NCO base is an active reactive group, directly affect the time limit of service of glue, therefore, in building-up process, will make-the NCO base exhausts; as far as possible if-NCO base is excessive or reaction is not thorough, be contain in the prepolymer not by end-blocking-the NCO group, be mixed with glue after, active-NCO base will react with thinner and airborne water molecules, viscosity can rise even gel gradually, until can not use.Therefore, for more stablized, the photocuring synthetic resins of anti-storage, the mass ratio in the prescription in control tolylene diisocyanate and the polyoxyethylene glycol is that 0.95:1 is suitable.
Contain mass percent in the described Hydroxyethyl acrylate and be 0.08% catalyzer, gel catalyst commonly used has dibutyl tin laurate or stannous octoate, preferred dibutyl tin laurate in the present embodiment.Dibutyl tin laurate is the catalyzer of strong gelling properties, can be used for polyurethane elastomer, tackiness agent, seal gum, coating, hard bubbles, moulded foam, RIM.Stopper commonly used has Resorcinol or p-ten.-butylcatechol, preferred Resorcinol in the present embodiment.The effect of stopper is to make stopper molecule and chain free radical reaction, forms the low activity free radical that the non-free radical material maybe can not cause, thereby polymerization is stopped.
The mass percent of described Hydroxyethyl acrylate, described hydroquinone of polymerization retarder, described catalyzer dibutyl tin laurate is shared ratio in the polyurethane acrylate prepolymer (PUA) synthetic in step 1.
Step 2: in the 5L four-hole boiling flask of agitator, thermometer is housed, add the polyurethane acrylate prepolymer that described step 1 prepares, described polyurethane acrylate prepolymer and free radical activity mixing diluents are stirred, add softening agent, light trigger, other auxiliary agents, stir 1-2h, until can obtain described ultraviolet light polymerization liquid optical cement finished product behind the described softening agent, described light trigger, the complete dissolve complete of described other auxiliary agents.
Described free radical activity thinner is Hydroxyethyl acrylate, tripropylene glycol double methacrylate, Viscoat 295, propoxylation glycerol triacrylate, 1, in 6-hexylene glycol methoxyl group mono acrylic ester, the ethoxylation neopentyl glycol methoxyl group mono acrylic ester one or more, preferred free radical activity thinner is three kinds of Hydroxyethyl acrylate, tripropylene glycol double methacrylate and Viscoat 295s in the present embodiment.The effect of described free radical activity thinner is to reduce system viscosity, can also participate in curing reaction, regulates snappiness, hardness and curing speed etc.
Described softening agent is dibutyl phthalate or dioctyl phthalate (DOP), pref-erable dioctyl phthalate in the present embodiment.Softening agent is in order to weaken the reactive force between polymer molecule, thereby improves the snappiness of glue, and lax internal stress has improved the shock strength of glue; Reduce softening temperature and the second-order transition temperature of glued membrane, improve lower temperature resistance; Reduce the viscosity of polymkeric substance, increase its flowability, increase glue to the infiltration of bonding plane, improve the bonding strength of joint.
Light trigger commonly used has benzophenone (BP); two (2; 4; the 6-trimethylbenzoyl) phenyl phosphine oxide (is called again initiator 819; BAPO); 2-methyl isophthalic acid-[4-(methyl sulfo-) phenyl]-2-(4-morpholinyl)-1-acetone (is called again Irgacure907; MMMP); 1-hydroxy-cyclohexyl phenyl ketone (is called again light trigger 184; HCPK); 2-hydroxy-2-methyl-1-phenyl-1-acetone (being called again light trigger 1173); 2-benzyl-2-dimethylamino-1-(4-morpholinyl phenyl)-the 1-butanone (is called again light trigger Irgacure369; BDMB); described BAPO and described 184 is the acyl group phosphine oxygen photoinitiator that Switzerland Ciba company produces, preferred BAPO in the present embodiment.The effect of light trigger is after it absorbs ultraviolet luminous energy, produces free radical through decomposing, thus the unsaturated link(age) polymerization in the initiator system, and crosslinking curing is in aggregates.
Described other auxiliary agents comprise coupling agent, defoamer and oxidation inhibitor, described coupling agent are KH-570 or KH-550, and the KH-550 chemical name is γ-aminopropyl triethoxysilane, the KH-570 chemical name is γ-methacryloxypropyl trimethoxy silane, preferred KH-570 in the present embodiment.Coupling agent is mainly used in improving bonding strength, the material mortise that namely two kinds of character is varied in size.Described defoamer is the modest defoamer 5600 of German moral, watt gram defoamer BYK-141, and a kind of among the BYK-163, the effect of defoamer is the formation that prevents foam and foaming in the product preparation process; The preferred BYK-141 of the present embodiment, described oxidation inhibitor are 2,6 ditertiary butyl p cresol (being called again antioxidant 264), and the effect of oxidation inhibitor is the stability that improves product.
The per-cent of various components is respectively polyurethane acrylate prepolymer 30% in the described preparation ultraviolet light polymerization liquid optical cement product, free radical activity thinner 55%, softening agent 12%, light trigger 2%, other auxiliary agents 1%.
Therefore the concrete operation step of step 2 is in the present embodiment: agitator is being housed, add the polyurethane acrylate prepolymer 30% that described step 1 prepares in the 5L four-hole boiling flask of thermometer, with described polyurethane acrylate prepolymer and free radical activity thinner 55% mixing and stirring, described free radical activity thinner is Hydroxyethyl acrylate, tripropylene glycol double methacrylate and Viscoat 295 are three's mixture, add dioctyl phthalate (DOP) 12%, BAPO2%, KH-5700.6%, BYK-1410.3%, 2640.1%, stir 1-2h, until described dioctyl phthalate (DOP), described BAPO, described KH-570, described BYK-141, can obtain described ultraviolet light polymerization liquid optical cement finished product after described 264 components dissolved are complete.
Embodiment 2
Identical with embodiment 1, difference is:
The concrete operation step of described step 2 is: agitator is being housed, add the polyurethane acrylate prepolymer 38% that described step 1 prepares in the 5L four-hole boiling flask of thermometer, with described polyurethane acrylate prepolymer and free radical activity thinner 48% mixing and stirring, described free radical activity thinner is Hydroxyethyl acrylate, tripropylene glycol double methacrylate and Viscoat 295 are three's mixture, add dioctyl phthalate (DOP) 10%, BAPO3%, KH-5700.6%, BYK-1410.3%, 2640.1%, stir 1-2h, until described dioctyl phthalate (DOP), described BAPO, described KH-570, described BYK-141, can obtain described ultraviolet light polymerization liquid optical cement finished product after described 264 components dissolved are complete.
Embodiment 3
Identical with embodiment 1, difference is:
The concrete operation step of described step 2 is: agitator is being housed, add the polyurethane acrylate prepolymer 45% that described step 1 prepares in the 5L four-hole boiling flask of thermometer, with described polyurethane acrylate prepolymer and free radical activity thinner 40% mixing and stirring, described free radical activity thinner is Hydroxyethyl acrylate, tripropylene glycol double methacrylate and Viscoat 295 are three's mixture, add dioctyl phthalate (DOP) 10%, BAPO4%, KH-5700.6%, BYK-1410.3%, 2640.1%, stir 1-2h, until described dioctyl phthalate (DOP), described BAPO, described KH-570, described BYK-141, can obtain described ultraviolet light polymerization liquid optical cement finished product after described 264 components dissolved are complete.
Embodiment 4
Identical with embodiment 1, difference is:
Described free radical activity thinner is preferably Hydroxyethyl acrylate, tripropylene glycol double methacrylate and propoxylation glycerol triacrylate three mixture, and described free radical activity thinner mass percent is 30%; Described softening agent is preferably dibutyl phthalate, and described dibutyl phthalate mass percent is 12%; Described light trigger is preferably 1-hydroxy-cyclohexyl phenyl ketone (HCPK), and the mass percent of described HCPK is 2%.
Embodiment 5
Identical with embodiment 4, difference is:
The concrete operation step of described step 2 is: agitator is being housed, add the polyurethane acrylate prepolymer 30% that described step 1 prepares in the 5L four-hole boiling flask of thermometer, with described polyurethane acrylate prepolymer and free radical activity thinner 45% mixing and stirring, described free radical activity thinner is Hydroxyethyl acrylate, tripropylene glycol double methacrylate and propoxylation glycerol triacrylate are three's mixture, add dibutyl phthalate 15%, HCPK6%, KH-5702.4%, BYK-1411.2%, 2640.4%, stir 1-2h, until described dioctyl phthalate (DOP), described HCPK, described KH-570, described BYK-141, can obtain described ultraviolet light polymerization liquid optical cement finished product after described 264 components dissolved are complete.
Embodiment 6
Identical with embodiment 4, difference is:
The concrete operation step of described step 2 is: agitator is being housed, add the polyurethane acrylate prepolymer 38% that described step 1 prepares in the 5L four-hole boiling flask of thermometer, with described polyurethane acrylate prepolymer and free radical activity thinner 48% mixing and stirring, described free radical activity thinner is Hydroxyethyl acrylate, tripropylene glycol double methacrylate and propoxylation glycerol triacrylate are three's mixture, add dibutyl phthalate 10%, HCPK3%, KH-5700.6%, BYK-1410.3%, 2640.1%, stir 1-2h, until described dioctyl phthalate (DOP), described HCPK, described KH-570, described BYK-141, can obtain described ultraviolet light polymerization liquid optical cement finished product after described 264 components dissolved are complete.
Embodiment 7
The prepared ultraviolet light polymerization liquid optical cement of embodiment 1-6 is done viscosity and performance test set time,
Viscosity test uses rotational viscosimeter Brookfield DV-II viscometer, test in the time of 25 ℃.
Concrete steps are:
1) sample of the same race is selected suitable identical rotor and rotating speed, makes reading in 20%~80% scope of scale card;
The container that 2) will fill sample is put into thermostatic bath, makes specimen temperature and test temperature balance, and keeps specimen temperature even;
3) rotor is dipped vertically into the sample centre, and makes liquid level reach rotor liquid level graticule;
4) start rotational viscosimeter, the reading when pointer is constant on disk when reading rotation, each Specimen Determination three times.
5) get minimum reading value in three sample testings.
The concrete steps of performance test set time are: on clean sheet glass, the above applies polyethylene film with sample coating, places illumination curing under the UV-lamp, and behind the illumination certain hour, with light finger extrusion film, if can not press trace, then sample has cured.
Table 1 is embodiment 1-6 ultraviolet light polymerization liquid optical cement viscosity and performance test set time table, and is as shown in table 1.
Table 1 embodiment 1-6 ultraviolet light polymerization liquid optical cement viscosity and performance test set time table
Embodiment 8
Embodiment 1-6 ultraviolet light polymerization liquid optical cement finished product is made the performance test table.Table 2 is performance test table before embodiment 1-6 ultraviolet light polymerization liquid optical cement finished product solidifies, and is as shown in table 2; Table 3 is performance test table after embodiment 1-6 ultraviolet light polymerization liquid optical cement finished product solidifies, and is as shown in table 3.
Performance test table before table 2 embodiment 1-6 ultraviolet light polymerization liquid optical cement finished product solidifies
Performance test table after table 3 embodiment 1-6 ultraviolet light polymerization liquid optical cement finished product solidifies
The characteristics such as the prepared ultraviolet light polymerization liquid optical cement of the present invention has that smell is low, modest viscosity, snappiness are good, has good transmittance and specific refractory power, and bonding strength is high, and water-fast, cold-hot impacts, time property, the performance such as anti-aging are good; Fully transparent after the curing, but product stable for extended periods of time height under high temperature, high humidity environment is transparent, not xanthochromia, not albefaction, degumming phenomenon not.
The above only is preferred embodiment of the present invention, and is in order to limit the present invention, within the spirit and principles in the present invention not all, any modification of doing, is equal to replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (10)
1. the preparation method of a ultraviolet light polymerization liquid optical cement is characterized in that, comprises the steps:
A) in reaction vessel, add tolylene diisocyanate, under 20~25 ℃ of conditions of normal temperature, stirring velocity is under 80~100 rev/mins the condition, polyoxyethylene glycol is splashed into reaction vessel, be warming up to 35~45 ℃, and insulation certain hour t, the mass ratio of described tolylene diisocyanate and described polyoxyethylene glycol is 0.95:1;
B) after t=3 hour, add mass percent and be 32.5% Hydroxyethyl acrylate reaction, add simultaneously mass percent and be 0.1% stopper, be warmed up to 65~70 ℃, insulation reaction 4 hours;
C) temperature is down to 50 ℃ in the question response container, adds mass percent and be 0.5% dehydrated alcohol reaction 20 minutes, and suction filtration namely gets polyurethane acrylate prepolymer;
D) described polyurethane acrylate prepolymer is cooled to 20~25 ℃, stir with the free radical activity thinner, add successively softening agent, light trigger and other auxiliary agents, stir 1~2h, until after described softening agent, described light trigger and other auxiliary agents dissolved fully, resulting product was described ultraviolet light polymerization liquid optical cement finished product.
2. the preparation method of ultraviolet light polymerization liquid optical cement as claimed in claim 1 is characterized in that: contain mass percent described in the described step b in the Hydroxyethyl acrylate and be 0.08% catalyzer dibutyl tin laurate.
3. the preparation method of ultraviolet light polymerization liquid optical cement as claimed in claim 1, it is characterized in that: described stopper is Resorcinol.
4. the preparation method of ultraviolet light polymerization liquid optical cement as claimed in claim 1, it is characterized in that: described free radical activity thinner is Hydroxyethyl acrylate, tripropylene glycol double methacrylate, Viscoat 295, propoxylation glycerol triacrylate, 1, one or more in 6-hexylene glycol methoxyl group mono acrylic ester, the ethoxylation neopentyl glycol methoxyl group mono acrylic ester.
5. the preparation method of ultraviolet light polymerization liquid optical cement as claimed in claim 1, it is characterized in that: described softening agent is dibutyl phthalate or dioctyl phthalate (DOP).
6. the preparation method of ultraviolet light polymerization liquid optical cement as claimed in claim 1; it is characterized in that: described light trigger is benzophenone, two (2; 4; the 6-trimethylbenzoyl) phenyl phosphine oxide, 2-methyl isophthalic acid-[4-(methyl sulfo-) phenyl]-2-(4-morpholinyl)-1-acetone, 1-hydroxy-cyclohexyl phenyl ketone, 2; 4,6-trimethylbenzoyl phenyl-phosphonic acid ethyl ester, 2-hydroxy-2-methyl-1-phenyl-1-acetone, 2-benzyl-2-dimethylamino-1-(4-morpholinyl phenyl)-in the 1-butanone one or more.
7. the preparation method of ultraviolet light polymerization liquid optical cement as claimed in claim 1, it is characterized in that: described other auxiliary agents comprise coupling agent and oxidation inhibitor, described coupling agent is γ-methacryloxypropyl trimethoxy silane, γ-aminopropyl triethoxysilane or N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, described oxidation inhibitor is 2,6 ditertiary butyl p cresol.
8. a ultraviolet light polymerization liquid optical cement is characterized in that, by mass percentage, comprise following component: polyurethane acrylate prepolymer 30%~45%, free radical activity thinner 40%~55%, softening agent 10%~15%, light trigger 2%~6%, other auxiliary agents.
9. ultraviolet light polymerization liquid optical cement as claimed in claim 8, it is characterized in that: described free radical activity thinner is Hydroxyethyl acrylate, tripropylene glycol double methacrylate, Viscoat 295, propoxylation glycerol triacrylate, 1, one or more in 6-hexylene glycol methoxyl group mono acrylic ester, the ethoxylation neopentyl glycol methoxyl group mono acrylic ester; Described softening agent is dibutyl phthalate or dioctyl phthalate (DOP); Described light trigger is benzophenone, two (2; 4; the 6-trimethylbenzoyl) phenyl phosphine oxide, 2-methyl isophthalic acid-[4-(methyl sulfo-) phenyl]-2-(4-morpholinyl)-1-acetone, 1-hydroxy-cyclohexyl phenyl ketone, 2; 4,6-trimethylbenzoyl phenyl-phosphonic acid ethyl ester, 2-hydroxy-2-methyl-1-phenyl-1-acetone, 2-benzyl-2-dimethylamino-1-(4-morpholinyl phenyl)-in the 1-butanone one or more.
10. ultraviolet light polymerization liquid optical cement as claimed in claim 8, it is characterized in that: described other auxiliary agents comprise coupling agent and oxidation inhibitor, described coupling agent is γ-methacryloxypropyl trimethoxy silane, γ-aminopropyl triethoxysilane or N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, described oxidation inhibitor is 2,6 ditertiary butyl p cresol.
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CN111383513A (en) * | 2018-12-31 | 2020-07-07 | 佛山艾仕仑科技有限公司 | Manufacturing method of single-layer transparent plastic substrate water label |
CN111635718A (en) * | 2019-03-01 | 2020-09-08 | 泰州隆基乐叶光伏科技有限公司 | Insulating adhesive, preparation method of insulating adhesive and IBC solar cell |
CN115010873A (en) * | 2022-06-21 | 2022-09-06 | 深圳大学 | Solid-solid phase change polymer material, preparation method thereof and glass window |
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-
2012
- 2012-12-26 CN CN2012105762341A patent/CN103031105A/en active Pending
Non-Patent Citations (1)
Title |
---|
韩俊凤: "UV固化聚氨酯丙烯酸酯胶粘剂的合成及性能研究", 《中国优秀博硕学位论文全文数据库(硕士)工程科技Ⅰ辑》 * |
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