CN102703020A - Liquid optical transparent adhesive with impact resistance and preparation method thereof - Google Patents
Liquid optical transparent adhesive with impact resistance and preparation method thereof Download PDFInfo
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- CN102703020A CN102703020A CN2012101931919A CN201210193191A CN102703020A CN 102703020 A CN102703020 A CN 102703020A CN 2012101931919 A CN2012101931919 A CN 2012101931919A CN 201210193191 A CN201210193191 A CN 201210193191A CN 102703020 A CN102703020 A CN 102703020A
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- optical lens
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- impact resistance
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Abstract
The invention relates to a liquid optical transparent adhesive with impact resistance and a preparation method thereof. The liquid state optical transparent adhesive comprises the following raw materials in percentage by weight: 15-45 percent of hydrogenated polybutadiene type polyurethane acrylate resin, 20-60 percent of liquid polybutadiene resin, 15-45 percent of long-chain alkane acrylic ester, 1-6 percent of light trigger and 0.1-1 percent of antioxidant. The refractive index of the liquid optical transparent adhesive is 1.50-1.52; and the liquid optical transparent adhesive has favorable impact resistance and internal friction tandelta of less than 0.6, is suitable for a laminating process of a capacitive touch screen and is especially suitable for occasions where special impact resistant demands are required.
Description
Technical field
The present invention relates to a kind of liquid optical lens gelatin and preparation method thereof, belong to the photo-curing material field with impact resistance.
Background technology
Along with the continual renovation of flat panel display is regenerated, touch-screen constantly is applied in the various products such as mobile phone, computer as a kind of new technology.Particularly under the ordering about of mobile Internet spring tide, increasing flat panel display product adopts the capacitive touch control techniques.The capacitive touch control techniques has advantage at aspects such as multiple contact design, gesture identification, speed of response, sensitivity, wearing quality, optical characteristics than traditional electric resistance touch-control technology.According to present production technique, capacitive touch screen need be used a kind of adhesives during fabrication each layer transparent material assembled, and to eliminate Newton's rings and rainbow phenomena, reduces the scattering loss of light, improves the brightness and contrast of flat-panel monitor.Adhesives generally adopted OCA (optical lens gelatin Optically Clear Adhesive) adhesive tape in the past; But LOCA (liquid optical lens gelatin) relative cost is lower; The bondline thickness flexible and controllable is more suitable in irregular the applying with middle large size screen.
The sealer of capacitive touch screen and conductive layer adopt glass baseplate mostly; Its specific refractory power is about 1.52; So require the specific refractory power of its adhesives approaching with it as far as possible; Can reduce the refraction loss of light between the interface in a large number, improve contrast gradient and the sharpness of flat-panel monitor in the high light environment.Under severe condition such as uviolizing, hydrothermal aging, thermal shock, the optical lens gelatin need keep the stable of important indicators such as high transmission rate, low-yellowing, more needs the good liquid optical lens gelatin of impact resistance at special occasions simultaneously.
At present, the specific refractory power of most of liquid optical lens gelatin is lower, and is big with specific refractory power 1.52 differences of glass generally below 1.50, thereby light is bigger in the refraction loss at interface; In addition, the impact resistance of known liquid optical lens gelatin is bad, and in-fighting is bigger, tan δ＞0.8 often, and this can cause in the application of some special occasions, and the stratified problem of cracking takes place.
Summary of the invention
Technical problem to be solved by this invention provides a kind of liquid optical lens gelatin with impact resistance and preparation method thereof, and the liquid optical lens gelatin of the present invention specific refractory power is 1.50～1.52, and impact resistance is good; In-fighting tan δ＜0.6; And the existing general in-fighting tan of liquid optical lens gelatin δ＞0.8, impact resistance is bad, therefore; The present invention is applicable to the attaching process of capacitive touch screen, is specially adapted to the occasion of special shock-resistant demand.
The technical scheme that the present invention solves the problems of the technologies described above is following: a kind of liquid optical lens gelatin with impact resistance; Said liquid optical lens gelatin is made up of following raw material by the percentage composition of raw material gross weight, and hydrogenated butadiene polymer type polyurethane acrylate resin accounts for 15～45%; The liquid polybutadiene resin accounts for 20～60%; Long chain alkane class propenoate accounts for 15～45%, and light trigger accounts for 1～6%, and oxidation inhibitor accounts for 0.1～1%.
The invention has the beneficial effects as follows: the most of raw materials in the liquid optical lens gelatin prescription of the present invention, selected long chain alkane molecular backbone chain for use with compliant structure, side group is seldom on the molecular backbone chain; When sub-chain motion, the internal friction resistance is less, thereby has reduced in-fighting, finally can make the impact resistance of optical cement good, compared with prior art, impact resistance is preferably arranged; And the specific refractory power of cured film is higher, and specific refractory power is 1.50～1.52, has significantly reduced the refraction loss of light between screen interface, has improved contrast gradient and the sharpness of flat-panel monitor in the high light environment.
On the basis of technique scheme, the present invention can also do following improvement.
Further, said hydrogenated butadiene polymer type polyurethane acrylate resin, its structural formula is represented by formula (I):
（Ⅰ）
Wherein: R represents 1; Hexamethylene-diisocyanate (HDI); Do not comprise a kind of in the part of isocyanate groups, R in isophorone diisocyanate (IPDI), Methylcyclohexyl diisocyanate (HTDI), dicyclohexyl methane diisocyanate (HMDI) molecular structure
1Representative-C
2H
4-,-C
3H
6-,-C
4H
8-in one or more, R
2Representative-H ,-CH
3In one or both.
The beneficial effect that adopts above-mentioned further scheme is that the liquid optical lens gelatin anti-yellowing property that the present invention is prepared is good, and color is difficult for jaundice under various ambient conditionss such as natural light, heat, oxygen.
Further, said liquid polybutadiene resin, its structural formula is represented by formula (II):
Wherein, the molecular weight of liquid polybutadiene resin is 500～5000, such as: one or both among the Polyoil 110 of EVONIK company (molecular weight 700～860), the Polyoil 130 (molecular weight 2700～3300).
The beneficial effect that adopts above-mentioned further scheme is that liquid polybutadiene resin double bond content is few, and molecular backbone chain is a long chain alkane, and side group seldom on the molecular backbone chain; When sub-chain motion; The internal friction resistance is less, has reduced in-fighting, makes the impact resistance of the liquid optical cement of the present invention good.
Further, said long chain alkane class propenoate is one or more mixing in Isooctyl acrylate monomer, Isooctyl methacrylate, isodecyl acrylate, isodecyl methacrylate, lauryl acrylate, lauryl methacrylate(LMA), tridecyl acrylate, methylacrylic acid tridecyl ester, vinylformic acid stearyl, the methylacrylic acid stearyl etc.
Further, said light trigger is one or more mixing in alpha-alcohol ketone verivate, the acyl group phosphorous oxides;
Further, said alpha-alcohol ketone verivate is 2-hydroxyl-2 methyl-phenyl-acetone-1 (light trigger 1173), 1-hydroxyl-phenylcyclohexane ketone (light trigger 184), 2-hydroxy-2-methyl-to one or more mixing in the hydroxyethyl ether phenyl-acetone-1 (light trigger 2959);
Further; Said acyl group phosphorous oxides is 2,4,6-trimethylbenzoyl-oxyethyl group-phenyl phosphorus oxide (light trigger TEPO), 2; 4; One or more mixing in 6-trimethylbenzoyl-diphenyl phosphate oxidation (light trigger TPO), two (2,4, the 6-trimethylbenzoyl) the phenyl phosphorus oxide (photoinitiator b APO);
Further; Said oxidation inhibitor is Hinered phenols antioxidant; For example be four [β-(3; The 5-di-tert-butyl-hydroxy phenyl) propionic acid] one or more mixing in the pentaerythritol ester (antioxidant 1010), 2,6 di tert butyl 4 methyl phenol (BHT), β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid octadecanol ester (antioxidant 1076);
The another kind of technical scheme that the present invention solves the problems of the technologies described above is following: a kind of preparation method with liquid optical lens gelatin of impact resistance comprises:
Hydrogenated butadiene polymer type polyurethane acrylate resin, liquid polybutadiene resin, long chain alkane class propenoate, light trigger, oxidation inhibitor are put into stirrer successively, stir, after the vacuumizing and defoaming, leave standstill naturally, promptly get to room temperature.
On the basis of technique scheme, the present invention can also do following improvement.
Further, saidly draw empty vacuum tightness and be-0.1～-0.05MPa, the time is 0.1～1h.
Embodiment
Below principle of the present invention and characteristic are described, institute gives an actual example and only is used to explain the present invention, is not to be used to limit scope of the present invention.
Embodiment 1
(shown in logical formula I, R represents the part that does not comprise isocyanate groups in the hexamethylene diisocyanate molecular structure, R accurately to take by weighing 30g hydrogenated butadiene polymer type polyurethane propenoate
1Representative-C
2H
4-, R
2Representative-H), 40g liquid polybutadiene resin (Polyoil 110), 30g Isooctyl acrylate monomer; 4g light trigger 184, the 0.2g antioxidant BHT adds above-mentioned each component in the duplicate rows star dynamic mixing stirrer successively; Mix and mix, and after the vacuumizing and defoaming (vacuum tightness-0.1MPa, 0.1h); Naturally leave standstill to room temperature, pack, promptly get.
Embodiment 2
(shown in logical formula I, R represents the part that does not comprise isocyanate groups in the isophorone diisocyanate molecular structure, R accurately to take by weighing 28g hydrogenated butadiene polymer type polyurethane propenoate
1Representative-C
3H
6-, R
2Representative-CH
3), 60g liquid polybutadiene resin (Polyoil 130), 15g isodecyl acrylate, 2g light trigger 1173; 1g light trigger TPO, the 0.2g antioxidant 1010 adds above-mentioned each component in the duplicate rows star dynamic mixing stirrer successively; Mix and mix, and after the vacuumizing and defoaming (vacuum tightness-0.09MPa, 0.5h); Naturally leave standstill to room temperature, pack, promptly get.
Embodiment 3
Accurately take by weighing 16g hydrogenated butadiene polymer type polyurethane propenoate and (shown in logical formula I, do not comprise the part of isocyanate groups in the R represent methylidene cyclohexyl diisocyanate molecular structure, left end R
1Representative-C
2H
4-C
3H
6-, right-hand member R
1Representative-C
2H
4-; Left end R
2Representative-H, right-hand member R
2Representative-CH
3), 60g liquid polybutadiene resin (Polyoil 130), 20g lauryl acrylate, 4g light trigger 184; 1g light trigger TEPO, the 0.8g antioxidant 1076 adds above-mentioned each component in the duplicate rows star dynamic mixing stirrer successively; Mix and mix, and after the vacuumizing and defoaming (vacuum tightness-0.07MPa, 0.7h); Naturally leave standstill to room temperature, pack, promptly get.
Embodiment 4
(shown in logical formula I, R represents the part that does not comprise isocyanate groups in the dicyclohexyl methane diisocyanate molecular structure, left end R accurately to take by weighing 43g hydrogenated butadiene polymer type polyurethane propenoate
1Representative-C
2H
4-C
3H
6-C
4H
8-, right-hand member R
1Representative-C
3H
6-C
4H
8-; R
2Representative-CH
3), 22g liquid polybutadiene resin (Polyoil 110), 18g lauryl methacrylate(LMA), 12g methylacrylic acid tridecyl ester; 3g light trigger 1173,0.3g photoinitiator b APO, the 0.1g antioxidant 1010 adds above-mentioned each component in the duplicate rows star dynamic mixing stirrer successively; Mix and mix, and after the vacuumizing and defoaming (vacuum tightness-0.05MPa, 1h); Naturally leave standstill to room temperature, pack, promptly get.
Embodiment 5
(shown in logical formula I, R represents the part that does not comprise isocyanate groups in the hexamethylene diisocyanate molecular structure, left end R accurately to take by weighing 33g hydrogenated butadiene polymer type polyurethane propenoate
1Representative-C
3H
6-, right-hand member R
1Representative-C
4H
8-; Left end R
2Representative-H, right-hand member R
2Representative-CH
3), 45g liquid polybutadiene resin (Polyoil 130), 8g Isooctyl methacrylate, 12g vinylformic acid stearyl; 1g light trigger 184,0.3g photoinitiator b APO, the 0.1g antioxidant BHT adds above-mentioned each component in the duplicate rows star dynamic mixing stirrer successively; Mix and mix, and after the vacuumizing and defoaming (vacuum tightness-0.07MPa, 0.4h); Naturally leave standstill to room temperature, pack, promptly get.
Embodiment 6
Accurately take by weighing 17g hydrogenated butadiene polymer type polyurethane propenoate and (shown in logical formula I, do not comprise in the part of isocyanate groups R in the R represent methylidene cyclohexyl diisocyanate molecular structure
1Representative-C
2H
4-, R
2Representative-H), 50g liquid polybutadiene resin (Polyoil 110), 28g Isooctyl methacrylate, 12g vinylformic acid stearyl; 3g light trigger 2959,0.3g photoinitiator b APO, the 0.1g antioxidant BHT adds above-mentioned each component in the duplicate rows star dynamic mixing stirrer successively; Mix and mix, and after the vacuumizing and defoaming (vacuum tightness-0.07MPa, 0.5h); Naturally leave standstill to room temperature, pack, promptly get.
Experimental example 1
By the contrast test that following method has been carried out in-fighting (tan δ) and specific refractory power with sample and the existing known optical transparent adhesive tape 1 and 2 of embodiment 1～6, test result is as shown in table 1.
Known optical transparent adhesive tape 1: accurately take by weighing 18g polybutadiene-modified propenoate TE2000 (Japanese Cao Da Chemical Co., Ltd), 42g liquid polybutadiene resin (Polyoil 110), 28g Isooctyl acrylate monomer; 3g light trigger 184,0.5g light trigger TPO adds above-mentioned each component in the stirrer successively; Mix, and after the vacuumizing and defoaming (vacuum tightness-0.09MPa, 1h); Naturally leave standstill to room temperature, pack, promptly get.
Known optical transparent adhesive tape 2: accurately take by weighing 30g aliphatic urethane acrylate 5191 (the two key chemical incs in Taiwan), 40g Isooctyl acrylate monomer, 4g light trigger 1173; 0.5g light trigger TPO adds above-mentioned each component in the stirrer successively, mixes; (vacuum tightness-0.09MPa 1h), leaves standstill to room temperature naturally after the vacuumizing and defoaming; Pack, promptly get.
In-fighting (tan δ) test condition: the DMA-Q800 of U.S. TA company, film stretching pattern, temperature-40 ℃～100 ℃, frequency 1Hz.Cured film thickness: 200um; Solidify energy: 3000mJ/cm
2
Refraction index test: Abbe refractometer.
Sample that table 1 embodiment 1～6 makes and known optical transparent adhesive tape performance comparison test result
| Sample | Specific refractory power | In-fighting tan δ |
| The sample of embodiment 1 | 1.512 | 0.56 |
| The sample of embodiment 2 | 1.511 | 0.39 |
| The sample of embodiment 3 | 1.512 | 0.41 |
| The sample of embodiment 4 | 1.512 | 0.51 |
| The sample of embodiment 5 | 1.511 | 0.49 |
| The sample of embodiment 6 | 1.512 | 0.47 |
| Known optical transparent adhesive tape 1 | 1.482 | 0.86 |
| Known optical transparent adhesive tape 2 | 1.476 | 0.91 |
Can find out that from The above results compared with present technology the liquid optical lens gelatin of the present invention has impact resistance preferably, in-fighting is less, and specific refractory power is higher, and the occasion that is adapted at higher shock-resistant demand is used.
The above is merely preferred embodiment of the present invention, and is in order to restriction the present invention, not all within spirit of the present invention and principle, any modification of being done, is equal to replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (6)
1. the liquid optical lens gelatin with impact resistance is characterized in that, said liquid optical lens gelatin is by the percentage composition of raw material gross weight; Form by following raw material; Hydrogenated butadiene polymer type polyurethane acrylate resin accounts for 15～45%, and the liquid polybutadiene resin accounts for 20～60%, and long chain alkane class propenoate accounts for 15～45%; Light trigger accounts for 1～6%, and oxidation inhibitor accounts for 0.1～1%.
2. liquid optical lens gelatin according to claim 1 is characterized in that, said hydrogenated butadiene polymer type polyurethane acrylate resin, and its structural formula is represented by formula (I):
Wherein, R represents hexamethylene diisocyanate, does not comprise a kind of in the part of isocyanate groups, R in isophorone diisocyanate, Methylcyclohexyl diisocyanate, the dicyclohexyl methane diisocyanate molecular structure
1Representative-C
2H
4-,-C
3H
6-,-C
4H
8-in one or more, R
2Representative-H ,-CH
3In one or both;
The molecular weight of said liquid polybutadiene resin is 500～5000, and its structural formula is represented by formula (II):
3. according to claim 1 or 2 arbitrary described liquid optical lens gelatin; It is characterized in that said long chain alkane class propenoate is one or more mixing in Isooctyl acrylate monomer, Isooctyl methacrylate, isodecyl acrylate, isodecyl methacrylate, lauryl acrylate, lauryl methacrylate(LMA), tridecyl acrylate, methylacrylic acid tridecyl ester, vinylformic acid stearyl, the methylacrylic acid stearyl; Said light trigger is one or more mixing in alpha-alcohol ketone verivate, the acyl group phosphorous oxides; Said oxidation inhibitor is Hinered phenols antioxidant.
4. liquid optical lens gelatin according to claim 3; It is characterized in that said alpha-alcohol ketone verivate is 2-hydroxyl-2 methyl-phenyl-acetone-1,1-hydroxyl-phenylcyclohexane ketone, 2-hydroxy-2-methyl-to one or more mixing in the hydroxyethyl ether phenyl-acetone-1; Said acyl group phosphorous oxides is 2,4,6-trimethylbenzoyl-oxyethyl group-phenyl phosphorus oxide, 2,4, one or more mixing in 6-trimethylbenzoyl-diphenyl phosphate oxidation, two (2,4, the 6-trimethylbenzoyl) phenyl phosphorus oxide; Said Hinered phenols antioxidant is one or more mixing in four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester, 2,6 di tert butyl 4 methyl phenol, β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid octadecanol ester.
5. preparation method with liquid optical lens gelatin of impact resistance; It is characterized in that; Comprise: hydrogenated butadiene polymer type polyurethane acrylate resin, liquid polybutadiene resin, long chain alkane class propenoate, light trigger, oxidation inhibitor are put into stirrer successively, stir, after the vacuumizing and defoaming; Naturally leave standstill to room temperature, promptly get.
6. the preparation method of liquid optical lens gelatin according to claim 5 is characterized in that, saidly draw empty vacuum tightness and be-0.1～-0.05MPa, the time is 0.1～1h.
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| Application Number | Priority Date | Filing Date | Title |
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| CN 201210193191 CN102703020B (en) | 2012-06-12 | 2012-06-12 | Liquid optical transparent adhesive with impact resistance and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201210193191 CN102703020B (en) | 2012-06-12 | 2012-06-12 | Liquid optical transparent adhesive with impact resistance and preparation method thereof |
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| CN102703020B CN102703020B (en) | 2013-10-23 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103952086A (en) * | 2014-04-29 | 2014-07-30 | 烟台德邦科技有限公司 | Ultraviolet curing adhesive and preparation method thereof |
| CN103980821A (en) * | 2014-05-16 | 2014-08-13 | 烟台德邦科技有限公司 | Liquid optical transparent adhesive and preparation method thereof |
| CN106065300A (en) * | 2015-04-24 | 2016-11-02 | 住华科技股份有限公司 | Adhesive Composition |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009086491A1 (en) * | 2007-12-28 | 2009-07-09 | E. I. Du Pont De Nemours And Company | Actinically curable adhesive composition |
| CN101560370A (en) * | 2009-05-15 | 2009-10-21 | 烟台德邦科技有限公司 | Light-curable adhesive with shock absorption property |
| CN102010494A (en) * | 2010-09-30 | 2011-04-13 | 烟台德邦电子材料有限公司 | Light-cured resin with low water absorption and preparation method thereof |
-
2012
- 2012-06-12 CN CN 201210193191 patent/CN102703020B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009086491A1 (en) * | 2007-12-28 | 2009-07-09 | E. I. Du Pont De Nemours And Company | Actinically curable adhesive composition |
| CN101560370A (en) * | 2009-05-15 | 2009-10-21 | 烟台德邦科技有限公司 | Light-curable adhesive with shock absorption property |
| CN102010494A (en) * | 2010-09-30 | 2011-04-13 | 烟台德邦电子材料有限公司 | Light-cured resin with low water absorption and preparation method thereof |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103952086A (en) * | 2014-04-29 | 2014-07-30 | 烟台德邦科技有限公司 | Ultraviolet curing adhesive and preparation method thereof |
| CN103952086B (en) * | 2014-04-29 | 2015-06-10 | 烟台德邦科技有限公司 | Ultraviolet curing adhesive and preparation method thereof |
| CN103980821A (en) * | 2014-05-16 | 2014-08-13 | 烟台德邦科技有限公司 | Liquid optical transparent adhesive and preparation method thereof |
| CN106065300A (en) * | 2015-04-24 | 2016-11-02 | 住华科技股份有限公司 | Adhesive Composition |
| CN106065300B (en) * | 2015-04-24 | 2018-06-15 | 住华科技股份有限公司 | Adhesive composition |
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| CN102703020B (en) | 2013-10-23 |
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Denomination of invention: Liquid optical transparent adhesive with impact resistance and preparation method thereof Effective date of registration: 20140808 Granted publication date: 20131023 Pledgee: China Everbright Bank, Limited by Share Ltd, Yantai branch Pledgor: Yantai Darbond Technology Co., Ltd. Registration number: 2014980000060 |
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