CN103113832A - UV (Ultraviolet) curing adhesive for optical lenslet adhesion and preparation method thereof - Google Patents
UV (Ultraviolet) curing adhesive for optical lenslet adhesion and preparation method thereof Download PDFInfo
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- CN103113832A CN103113832A CN2013100648715A CN201310064871A CN103113832A CN 103113832 A CN103113832 A CN 103113832A CN 2013100648715 A CN2013100648715 A CN 2013100648715A CN 201310064871 A CN201310064871 A CN 201310064871A CN 103113832 A CN103113832 A CN 103113832A
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Abstract
The invention belongs to the technical field of adhesion, and particularly provides a UV (Ultraviolet) curing adhesive for optical lenslet adhesion and a preparation method thereof. The UV curing adhesive comprises photosensitive resin, semi-solid bisphenol epoxide resin, glycidyl ester epoxide resin, an acrylic ester cross-linking agent, a diluting agent I, a photosensitizer and a polymerization inhibitor I, wherein the photosensitive resin comprises bisphenol A type epoxide resin, acrylic acid or methacrylic acid, a catalyst, a polymerization inhibitor II and a diluting agent II. The adhesive prepared through the method provided by the invention has the advantages of similar solid state, moderate strength, low volume shrinkage ratio during curing, small stress of an adhered part, good image quality, good ageing resistant property, life-time service, no obvious change of adhesive layer color and transmittance, moderate adhesive strength and easiness for adhesive disassembly of the adhered part, is very easy to meet the requirements for optical center coincidence or size of the adhered part and ensures the optical property of the adhered part.
Description
Technical field
The invention belongs to the adhesive technology field, particularly a kind of for bonding UV cured adhesive of optics lenslet and preparation method thereof.
Background technology
Optical adhesive is mainly used in gluing together the opticglass part of opticinstrument light path system, so that it satisfies product optical design requirement.Basic demand to optical adhesive is: it is good etc. that high, suitable bonding strength, the volumetric shrinkage of spectral transmittance is little, high temperature performance reaches well chemical stability, has simultaneously good processing performance, to satisfy the requirement of optical element gummed.The kind of existing optical adhesive mainly contains: the optics light-sensitive emulsion that Canada balsam, methyl alcohol glue, optics epoxy glue and UV solidify, especially the optics light-sensitive emulsion that solidifies of UV, owing to adopting the ultra-violet curing technology, select photosensitive functional material to be prepared from, therefore has curing speed fast, high temperature performance preferably, technique is easier, optical property and the characteristics such as mechanical property is good, now replace gradually Canada balsam, methyl alcohol glue, optics epoxy glue, become the first-selection of present optical veneering.
Yet, bonding for the optics lenslet, connect intensity because existing optics UV is gluing too high, string stress is large, make the gummed part be difficult to tear open glue, easily cause the damage of part, and existing optical cement is because viscosity is little, be difficult to satisfy the gummed for the optical element of less non-automatic alignment optical center or size, centre deviation is larger, even adopt relevant accessory, still can not make larger improvement, and efficient is lower, has limited its application in the optics lenslet is bonding.
Summary of the invention
In order to overcome the shortcoming of above-mentioned prior art, the object of the present invention is to provide a kind of for bonding UV cured adhesive of optics lenslet and preparation method thereof, gluing to connect intensity too high to solve existing optics UV, the large problems such as glue difficulty, optical element damage of tearing open that cause of string stress, and improve the optical element gummed working efficiency of less non-automatic alignment optical center or size, make gummed Central of the parts and size controlled.
For solving the problems of the technologies described above, the objective of the invention is to be achieved through the following technical solutions:
A kind of for the bonding UV cured adhesive of optics lenslet, the component of being divided by following quality forms: photosensitive resin 100, semi-solid state bisphenol epoxy 150~250, glycidyl ester based epoxy resin 15~25, acrylic ester cross-linking agent 5~15, thinner one 3~5, photosensitizers 2~4 and stopper one 0.5~1.
The component that described photosensitive resin is divided by following quality forms: bisphenol A type epoxy resin 300~360, acrylic or methacrylic acid 45~72, catalyzer 3.45~6.33, stopper 2 2.42~4.22 and thinner 2 20.
Described stopper one all can be Resorcinol with stopper two, or is MEHQ, or is 2,6 ditertiary butyl p cresol, or is 2,5-dimethyl Resorcinol.
Preferably, described acrylic ester cross-linking agent is two senses or trifunctional linking agent, can be Phthalic acid, diallyl ester, Viscoat 295, tripropylene glycol double methacrylate or hexylene glycol double methacrylate.
Preferably, described thinner one and thinner two are reactive thinner or inert diluent, can be dibutyl phthalate or isobornyl acrylate.
Preferably, described photosensitizers is free radical type, cationic or compound system both, can be benzoin dimethylether, it is perhaps the hydroxy-cyclohexyl phenyl ketone, being perhaps hydroxy-cyclohexyl phenyl ketone and diphenyl iodine hexafluorophosphate compound, is perhaps hydroxy-cyclohexyl phenyl ketone and 4-aminomethyl phenyl phenylbenzene sulphur hexafluorophosphate compound.
The present invention provides a kind of described method for the bonding UV cured adhesive of optics lenslet for preparing simultaneously, comprises the steps:
Step 1: preparation photosensitive resin
The there-necked flask that (1) agitator, thermometer, reflux exchanger will be housed is placed on infrared lamp, adds successively the catalyzer of respective amount from beaker one side, stopper two, and thinner two, agitator is started in acrylic or methacrylic acid, and solid is all dissolved;
(2) add again the part bisphenol A type epoxy resin, stir, begin to be warming up to 110 ℃, reacted 0.5 hour;
(3) survey acid number 160-200mgKOH/g, add the residue bisphenol A type epoxy resin, continue reaction, acid number reaches 30-50mgKOH/g, stopped reaction; Do not reach requirement as acid number, continue reaction, until till reaching;
Step 2: preparation tackiness agent
(1) divide by quality and take each component in Erlenmeyer flask, add the acetone heated and stirred to dissolving fully;
(2) use the filter paper secondary filtration in distilling flask;
(3) steam acetone with the vacuum decompression device;
(4) will distill after in matrass colloid pour in the Plastic Bottle of cleaned and oven dry, dress glue capacity is half of volume;
(5) censorship is labelled, warehouse-in.
Tackiness agent index of the present invention is as follows:
Project | Technical qualification |
Outward appearance | Light, transparent semi-solid state |
Degree of cleaning (dust number, individual/cm 3) | ≤8 |
1/4 cone penetration (1/10mm) | 20-40 |
Oxirane value | 0.20-0.25 |
Compression shear strength (MPa) | 5-8 |
Refractive index N D 20 | 1.545-1.565 |
In the enforcement of technical solution of the present invention, carry out the esterification by ring opening reaction by light-coloured transparent bisphenol A type epoxy resin and the refining acrylic or methacrylic acid of selecting different metering ratios at suitable catalyzer and stopper, obtain the photosensitive resin of the high photo-curing rate of different end group structure, and select dissimilar epoxy resin, corresponding crosslinked and thinner, different initiation photosensitive systems, to realize the control of colloid viscosity and intensity, and other optical property requirement also can be met, thereby realize purpose of the present invention.
By above technical scheme, the invention has the beneficial effects as follows:
(1) solidify optical cement with existing general UV and compare, because formula system has selected a large amount of high viscosity epoxy resin toughened, adopt the photosensitive resin of different structure, initiator system also is optimized, therefore that the tackiness agent that forms is bordering on is solid-state, and moderate strength, during curing, volumetric shrinkage is little, the stress of gummed part is little, and picture element is good, and ageing-resistant performance is good, life-time service, glue-line color and transmitance are without considerable change, and cohesive strength is moderate, and the gummed part is easily torn glue open;
(2) because viscosity is larger, sensitive to heat, can change by its viscosity when gummed and realize centering requirement, special in little lens, because deadweight is less, the variation of heat is more responsive for part, is very easy to realize that gummed part optical center overlaps or dimensional requirement, the optical property of guaranteeing to glue together part.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in detail.
Embodiment one:
It is a kind of for bonding UV cured adhesive of optics lenslet and preparation method thereof that the present embodiment provides, and it is bonding that this tackiness agent is fit to the optics lenslet very much.
Adhesive preparation method is as follows:
1, preparation photosensitive resin
1.1 photosensitive resin proportioning:
Raw material | Mass parts | Requirement | Remarks |
Bisphenol A type epoxy resin (oxirane value 0.31) | 360 | Light-coloured transparent | Customized |
Methacrylic acid | 62 | Refining | Vacuum fractionation |
Tetramethyl ammonium chloride | 4.22 | Refining | Recrystallization |
Resorcinol | 4.22 | Refining | ? |
Dibutyl phthalate (DBP) | 20 | Analytical pure | ? |
1.2 the preparation of photosensitive resin:
agitator will be housed, thermometer, the there-necked flask of the 500ml of reflux exchanger is placed on infrared lamp, add catalyzer tetramethyl ammonium chloride 4.22 mass parts from beaker one side, hydroquinone of polymerization retarder 4.22 mass parts, thinner dibutyl phthalate (DBP) 20 mass parts, refining methacylic acid 62 mass parts, start agitator, make it whole dissolvings, add bisphenol A type epoxy resin (oxirane value 0.31) 180 mass parts, stir, begin to be warming up to 110 ℃, reacted 0.5 hour, acid number reaches 160mgKOH/g, then add residue bisphenol A type epoxy resin (oxirane value 0.31) 180 quality to divide, reacted 1 hour, acid number reaches 32mgKOH/g, stopped reaction, make photosensitive resin.
2, preparation tackiness agent
2.1 adhesive ratio:
Raw material | Mass parts | Requirement |
Photosensitive resin | 100 | Self-control |
Bisphenol A type epoxy resin (oxirane value 0.31) | 150 | Customized |
Hexahydrophthalic acid glycidyl ester (oxirane value 0.65) | 15 | Customized |
Phthalic acid, diallyl ester (DAP) | 5 | Refining |
Dibutyl phthalate (DBP) | 3 | Refining |
Benzoin dimethylether (651) | 2.5 | 2 |
Resorcinol | 0.5 | Refining |
2.2 the preparation of tackiness agent
2.2.1 take various raw materials in Erlenmeyer flask by said ratio, add acetone 500ml, heat 60 ℃ and be stirred to dissolving fully;
2.2.2 carry out secondary filtration in distilling flask with quantitative paper;
2.2.3 steam acetone with the vacuum decompression device;
2.2.4 after distilling in matrass colloid pour in the Plastic Bottle of cleaned and oven dry, dress glue capacity is half of volume;
2.2.5 censorship is labelled, and namely gets semi-solid state UV curable adhesive.
3, actual measurement index
Project | Technical qualification | Remarks |
Outward appearance | Light, transparent semi-solid state | ? |
Degree of cleaning (dust number, individual/cm 3) | 5 | ? |
1/4 cone penetration (1/10mm) | 36 | ? |
Oxirane value | 0.25 | ? |
Compression shear strength (MPa) | 5.2 | ? |
Refractive index N D 20 | 1.552 | ? |
Embodiment two:
It is a kind of for bonding UV cured adhesive of optics lenslet and preparation method thereof that the present embodiment provides, and is fit to very much the optics lenslet bonding.
1, preparation photosensitive resin
1.1 photosensitive resin proportioning:
Raw material | Mass parts | Requirement | Remarks |
Bisphenol A type epoxy resin (oxirane value 0.31) | 350 | Light-coloured transparent | Customized |
Methacrylic acid | 72 | Refining | Vacuum fractionation |
Triphenyl phosphorus | 6.33 | Refining | Recrystallization |
MEHQ | 2.95 | Refining | ? |
Dibutyl phthalate (DBP) | 20 | Analytical pure | ? |
1.2 the preparation of photosensitive resin:
agitator will be housed, thermometer, the there-necked flask of the 500ml of reflux exchanger is placed on infrared lamp, add catalyzer triphenyl phosphorus 6.33 mass parts from beaker one side, stopper MEHQ 2.95 mass parts, thinner dibutyl phthalate (DBP) mass parts 20, refining methacylic acid 72 mass parts, start agitator, make it whole dissolvings, add bisphenol A type epoxy resin (oxirane value 0.31) 150 mass parts, stir, begin to be warming up to 115 ℃, reacted 0.5 hour, acid number 185mgKOH/g, then, add all the other bisphenol A type epoxy resins (oxirane value 0.31) 200 quality to divide, reacted 1 hour, acid number reaches 48mgKOH/g, stopped reaction, make photosensitive resin.
2, preparation tackiness agent
2.1 adhesive ratio:
Raw material | Mass parts | Requirement |
Photosensitive resin | 100 | Self-control |
Bisphenol A type epoxy resin (oxirane value 0.31) | 200 | Customized |
Hexahydrophthalic acid glycidyl ester (oxirane value 0.65) | 20 | Customized |
Viscoat 295 (TMPTA) | 10 | Refining |
Isobornyl acrylate (IBOA) | 4 | Refining |
Hydroxy-cyclohexyl phenyl ketone (184) | 2.0 | 2 |
MEHQ | 1.0 | Refining |
2.2 the preparation of tackiness agent
2.2.1 take various raw materials in Erlenmeyer flask by said ratio, add acetone 500ml, heat 60 ℃ and be stirred to dissolving fully;
2.2.2 carry out secondary filtration in distilling flask with quantitative paper;
2.2.3 steam acetone with the vacuum decompression device;
2.2.4 after distilling in matrass colloid pour in the Plastic Bottle of cleaned and oven dry, dress glue capacity is half of volume;
2.2.5 censorship is labelled, and namely gets semi-solid state UV curable adhesive.
3, actual measurement index
Project | Technical qualification | Remarks |
Outward appearance | Light, transparent semi-solid state | ? |
Degree of cleaning (dust number, individual/cm 3) | 6 | ? |
1/4 cone penetration (1/10mm) | 30 | ? |
Oxirane value | 0.22 | ? |
Compression shear strength (MPa) | 7.1 | ? |
Refractive index N D 20 | 1.562 | ? |
Embodiment three:
It is a kind of for bonding UV cured adhesive of optics lenslet and preparation method thereof that the present embodiment provides, and is fit to very much the optics lenslet bonding.
1, preparation photosensitive resin
1.1 photosensitive resin proportioning:
Raw material | Mass parts | Requirement | Remarks |
Bisphenol A type epoxy resin (oxirane value 0.31) | 300 | Light-coloured transparent | Customized |
Vinylformic acid | 45 | Refining | Vacuum fractionation |
Triethylamine | 3.45 | Refining | Recrystallization |
2,6 ditertiary butyl p cresol | 2.42 | Refining | ? |
Dibutyl phthalate (DBP) | 20 | Analytical pure | ? |
1.2 the preparation of photosensitive resin
agitator will be housed, thermometer, the there-necked flask of the 500ml of reflux exchanger is placed on infrared lamp, add catalyst of triethylamine 3.45 mass parts from beaker one side, stopper 2, 6-ditertbutylparacresol 2.42 mass parts, thinner dibutyl phthalate (DBP) mass parts 20, refining vinylformic acid 45 mass parts, start agitator, make whole dissolvings, add 638 epoxy resin 150 mass parts, stir, begin to be warming up to 115 ℃, reacted 0.5 hour, acid number 176mgKOH/g, then, add all the other 638 epoxy resin 150 quality to divide, reacted 1 hour, acid number reaches 41mgKOH/g, stopped reaction, make photosensitive resin.
2, preparation tackiness agent
2.1 adhesive ratio:
2.2 the preparation of tackiness agent
2.2.1 take various raw materials in Erlenmeyer flask by above-mentioned formula, add acetone 500ml, heat 60 ℃ and be stirred to dissolving fully;
2.2.2 carry out secondary filtration in distilling flask with quantitative paper;
2.2.3 steam acetone with the vacuum decompression device.
2.2.4 after distilling in matrass colloid pour in the Plastic Bottle of cleaned and oven dry, dress glue capacity is half of volume;
2.2.5 censorship is labelled, and namely gets semi-solid state UV curable adhesive.
3, actual measurement index
Project | Technical qualification | Remarks |
Outward appearance | Light, transparent semi-solid state | ? |
Degree of cleaning (dust number, individual/cm 3) | 8 | ? |
1/4 cone penetration (1/10mm) | 28 | ? |
Oxirane value | 0.24 | ? |
Compression shear strength (MPa) | 6.8 | ? |
Refractive index N D 20 | 1.548 | ? |
Embodiment four:
It is a kind of for bonding UV cured adhesive of optics lenslet and preparation method thereof that the present embodiment provides, and is fit to very much the optics lenslet bonding.
1, preparation photosensitive resin
1.1 proportioning:
Raw material | Mass parts | Requirement | Remarks |
Bisphenol A type epoxy resin (oxirane value 0.31) | 300 | Light-coloured transparent | Customized |
Vinylformic acid | 55 | Refining | Vacuum fractionation |
Tetraethylammonium bromide | 3.55 | Refining | Recrystallization |
2,5-dimethyl Resorcinol | 2.49 | Refining | ? |
Dibutyl phthalate (DBP) | 20 | Analytical pure | ? |
1.2 the preparation of photosensitive resin
agitator will be housed, thermometer, the there-necked flask of the 500ml of reflux exchanger is placed on infrared lamp, add catalyzer tetraethylammonium bromide 3.55 mass parts from beaker one side, stopper 2, 5-dimethyl Resorcinol 2.49 mass parts, thinner dibutyl phthalate (DBP) mass parts 20, refining vinylformic acid 55 mass parts, start agitator, make whole dissolvings, add 638 epoxy resin 200 mass parts, stir, begin to be warming up to 115 ℃, reacted 0.5 hour, acid number 170mgKOH/g, then, add all the other 638 epoxy resin 100 quality to divide, reacted 1.5 hours, acid number reaches 38mgKOH/g, stopped reaction, make photosensitive resin.
2, preparation tackiness agent
2.1 adhesive ratio:
2.2 the preparation of tackiness agent
2.2.1 take various raw materials in Erlenmeyer flask by above-mentioned formula, add acetone 500ml, heat 60 ℃ and be stirred to dissolving fully.
2.2.2 carry out secondary filtration in distilling flask with quantitative paper.
2.2.3 steam acetone with the vacuum decompression device.
2.2.4 after distilling in matrass colloid pour in the Plastic Bottle of cleaned and oven dry, dress glue capacity is half of volume;
2.2.5 censorship is labelled, and namely gets semi-solid state UV curable adhesive.
3, actual measurement index
Project | Technical qualification | Remarks |
Outward appearance | Light, transparent semi-solid state | ? |
Degree of cleaning (dust number, individual/cm 3) | 6 | ? |
1/4 cone penetration (1/10mm) | 34 | ? |
Oxirane value | 0.24 | ? |
Compression shear strength (MPa) | 6.9 | ? |
Refractive index N D 20 | 1.565 | ? |
In sum, synthesized the photosensitive resin of different end group mechanism with different stoichiometric reaction from acrylic or methacrylic acid by the employing bisphenol A type epoxy resin in the embodiment of the present invention, and select dissimilar epoxy resin to carry out glue and photosensitive resin coupling, adopt linking agent and activity or the inert diluent of two senses or trifunctional, different initiation photosensitive systems, realized the control of colloid viscosity and intensity, other optical property requires also can be met, thereby realizes purpose of the present invention.
Above embodiment only is used for explanation the present invention, but not limits the scope of the invention.In addition, after having read content of the present invention, those skilled in the art can make various changes or modification to the present invention, and these equivalent form of values still belong to the present patent application appended claims limited range.
Claims (10)
1. one kind is used for the bonding UV cured adhesive of optics lenslet, it is characterized in that, the component of being divided by following quality forms: photosensitive resin 100, semi-solid state bisphenol epoxy 150~250, glycidyl ester based epoxy resin 15~25, acrylic ester cross-linking agent 5~15, thinner one 3~5, photosensitizers 2~4 and stopper one 0.5~1.
2. according to claim 1 a kind of for the bonding UV cured adhesive of optics lenslet, it is characterized in that, the component that described photosensitive resin is divided by following quality forms: bisphenol A type epoxy resin 300~360, acrylic or methacrylic acid 45~72, catalyzer 3.45~6.33, stopper 2 2.42~4.22 and thinner 2 20.
3. according to claim 1 and 2 a kind ofly it is characterized in that for the bonding UV cured adhesive of optics lenslet,
Described stopper one is Resorcinol, or is MEHQ, or is 2,6 ditertiary butyl p cresol, or is 2,5-dimethyl Resorcinol;
Described stopper two is Resorcinol, or is MEHQ, or is 2,6 ditertiary butyl p cresol, or is 2,5-dimethyl Resorcinol.
4. according to claim 1 a kind ofly it is characterized in that for the bonding UV cured adhesive of optics lenslet, described thinner one is reactive thinner or inert diluent, and described thinner two is reactive thinner or inert diluent.
5. according to claim 1 or 4 described a kind ofly it is characterized in that for the bonding UV cured adhesive of optics lenslet,
Described thinner one is dibutyl phthalate or isobornyl acrylate;
Described thinner two is dibutyl phthalate or isobornyl acrylate.
6. according to claim 1 a kind ofly it is characterized in that for the bonding UV cured adhesive of optics lenslet, described acrylic ester cross-linking agent is two senses or trifunctional linking agent.
7. according to claim 1 or 6 is described a kind of for the bonding UV cured adhesive of optics lenslet, it is characterized in that, described alkene esters of gallic acid linking agent is Phthalic acid, diallyl ester, Viscoat 295, tripropylene glycol double methacrylate or hexylene glycol double methacrylate.
8. according to claim 1 a kind ofly it is characterized in that for the bonding UV cured adhesive of optics lenslet, described photosensitizers is free radical type, cationic or compound system both.
9. according to claim 1 or 8 is described a kind of for the bonding UV cured adhesive of optics lenslet, it is characterized in that, described photosensitizers is benzoin dimethylether, it is perhaps the hydroxy-cyclohexyl phenyl ketone, being perhaps hydroxy-cyclohexyl phenyl ketone and diphenyl iodine hexafluorophosphate compound, is perhaps hydroxy-cyclohexyl phenyl ketone and 4-aminomethyl phenyl phenylbenzene sulphur hexafluorophosphate compound.
10. one kind prepares the described method for the bonding UV cured adhesive of optics lenslet of claim 1, it is characterized in that, comprises the steps:
Step 1: preparation photosensitive resin
The there-necked flask that (1) agitator, thermometer, reflux exchanger will be housed is placed on infrared lamp, adds successively the catalyzer of respective amount from beaker one side, stopper two, and thinner two, agitator is started in acrylic or methacrylic acid, and solid is all dissolved;
(2) add again the part bisphenol A type epoxy resin, stir, begin to be warming up to 110 ℃, reacted 0.5 hour;
(3) survey acid number 160-200mgKOH/g, add the residue bisphenol A type epoxy resin, continue reaction, acid number reaches 30-50mgKOH/g, stopped reaction; Do not reach requirement as acid number, continue reaction, until till reaching;
Step 2: preparation tackiness agent
(1) divide by quality and take each component in Erlenmeyer flask, add the acetone heated and stirred to dissolving fully;
(2) use the filter paper secondary filtration in distilling flask;
(3) steam acetone with the vacuum decompression device;
(4) will distill after in matrass colloid pour in the Plastic Bottle of cleaned and oven dry, dress glue capacity is half of volume;
(5) censorship is labelled, warehouse-in.
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN104656988A (en) * | 2015-01-23 | 2015-05-27 | 苏州斯迪克新材料科技股份有限公司 | Manufacture method of full-lamination touch display module |
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CN101007929A (en) * | 2006-01-26 | 2007-08-01 | 深圳清华大学研究院 | Free radical- cation type ultraviolet photo-curing cementing agent and its preparation method |
WO2008035791A1 (en) * | 2006-09-22 | 2008-03-27 | Henkel Corporation | Bonding method and adhesive resin composition |
CN1989164B (en) * | 2004-07-22 | 2010-11-24 | 株式会社三键 | Curable composition |
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2013
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1989164B (en) * | 2004-07-22 | 2010-11-24 | 株式会社三键 | Curable composition |
CN101007929A (en) * | 2006-01-26 | 2007-08-01 | 深圳清华大学研究院 | Free radical- cation type ultraviolet photo-curing cementing agent and its preparation method |
WO2008035791A1 (en) * | 2006-09-22 | 2008-03-27 | Henkel Corporation | Bonding method and adhesive resin composition |
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Publication number | Priority date | Publication date | Assignee | Title |
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CN104656988A (en) * | 2015-01-23 | 2015-05-27 | 苏州斯迪克新材料科技股份有限公司 | Manufacture method of full-lamination touch display module |
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Application publication date: 20130522 |