CN115651099B - Preparation method of compound photoinitiator for low-refractive-index optical fiber coating - Google Patents
Preparation method of compound photoinitiator for low-refractive-index optical fiber coating Download PDFInfo
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- CN115651099B CN115651099B CN202211322595.3A CN202211322595A CN115651099B CN 115651099 B CN115651099 B CN 115651099B CN 202211322595 A CN202211322595 A CN 202211322595A CN 115651099 B CN115651099 B CN 115651099B
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- 238000000576 coating method Methods 0.000 title claims abstract description 53
- 239000011248 coating agent Substances 0.000 title claims abstract description 47
- 239000013307 optical fiber Substances 0.000 title claims abstract description 36
- 150000001875 compounds Chemical class 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 239000003999 initiator Substances 0.000 claims abstract description 44
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 34
- 239000011737 fluorine Substances 0.000 claims abstract description 34
- 239000000126 substance Substances 0.000 claims abstract description 18
- -1 acrylic ester Chemical class 0.000 claims abstract description 15
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 235000019441 ethanol Nutrition 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims abstract description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 claims abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 230000006837 decompression Effects 0.000 claims description 5
- BDAHDQGVJHDLHQ-UHFFFAOYSA-N [2-(1-hydroxycyclohexyl)phenyl]-phenylmethanone Chemical compound C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C1(O)CCCCC1 BDAHDQGVJHDLHQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 238000007789 sealing Methods 0.000 claims description 4
- 238000003860 storage Methods 0.000 claims description 4
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 2
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 claims description 2
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- CHAGFXOGGUIYIM-UHFFFAOYSA-N (2-cyclohexyl-3-hydroxyphenyl)-phenylmethanone Chemical compound Oc1cccc(C(=O)c2ccccc2)c1C1CCCCC1 CHAGFXOGGUIYIM-UHFFFAOYSA-N 0.000 abstract 1
- 238000001723 curing Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000178 monomer Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000005253 cladding Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- CSUFEOXMCRPQBB-UHFFFAOYSA-N 1,1,2,2-tetrafluoropropan-1-ol Chemical compound CC(F)(F)C(O)(F)F CSUFEOXMCRPQBB-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 239000012949 free radical photoinitiator Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical group C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 238000001448 refractive index detection Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- Paints Or Removers (AREA)
Abstract
The invention discloses a compound photoinitiator for a low-refractive-index optical fiber coating and a preparation method thereof. The compound photoinitiator consists of 25-36% of main substances of a fluorine-containing initiator, 13.15-25.25% of fluorine-containing acrylic ester and 2-4% of 2-hydroxy-2-methyl-1-phenylpropionic acid; wherein the main body substance of the fluorine-containing initiator consists of 30-55% of perfluorohexyl ethyl alcohol, 15-35% of hydroxy-cyclohexyl benzophenone, 15-40% of triphenylmethane triisocyanate and 0.1-0.3% of dibutyltin dilaurate. The compound photoinitiator for the low-refractive-index optical fiber coating has a low refractive index, has good compatibility with the low-refractive-index optical fiber coating, has high curing efficiency, can adjust the refractive index, and can be used as a low-refractive-index temperature-resistant optical fiber coating initiator.
Description
Technical Field
The invention relates to the field of photoinitiators, in particular to a preparation method of a compound photoinitiator for a low-refractive-index optical fiber coating.
Background
Low refractive index optical fiber coatings require coatings having very low refractive indices, the major components of such coatings: a fluorine-containing low refractive index resin prepolymer, a reactive diluent, a free radical photoinitiator and an auxiliary agent. Among these, the coating system has some special requirements for the initiator used: 1. the refractive index of the initiator is as low as possible, so that the change of the refractive index of the coating after UV curing can be ensured to be within an acceptable range; 2. the initiator, the resin prepolymer and the diluent monomer have better miscibility, and the paint is in a colorless transparent state before and after curing because the paint is widely applied to the inner cladding of the special optical fiber and needs to have good light transmission performance to specific light rays; 3. the low refractive index optical fiber coating is cured by ultraviolet radiation, and the heat generated during curing can cause some photoinitiators to generate obvious yellowing phenomenon, which can adversely affect the performances of coating such as light transmission and the like; 4. the initiator has higher activity and better initiation efficiency. In summary, a special compound photoinitiator for low-refractive-index optical fiber coating is prepared, and the initiator has a low refractive index and good miscibility with the coating.
Currently, the photoinitiators commonly used for low refractive index optical fiber coatings are two types: 1. a cleavage type radical initiator. One or more initiators represented by 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide (TPO), 2-hydroxy-2-methyl-phenyl acetone-1 (1173), 1-hydroxy-cyclohexyl benzophenone (184), 2-hydroxy-2-methyl-p-hydroxyethyl ether-phenyl acetone (2959), alpha-Diethoxyacetophenone (DEAP) and the like are compounded and combined to form the special photoinitiator for the optical fiber coating. Because the traditional initiator has the structural characteristics that the refractive index is higher and the general refractive index is more than 1.40, the refractive index of the coating is increased rapidly after the whole coating is cured, and the performance of the coating is affected; 2. photoactive groups are incorporated into the coating prepolymer. The method aims at introducing a radical structure capable of generating free radicals after receiving ultraviolet radiation on the basis of a molecular structure in the process of designing the optical fiber coating prepolymer, and the method needs to carry out great modification on the coating prepolymer and has great influence on the curing performance of the coating; 3. synthesizing a polymerizable monomer having a photoactive group. The method is mainly aimed at improving the photopolymerization dynamic performance of the photoinitiator, so that the oxygen polymerization inhibition effect is slowed down during photocuring, the curing effect is improved, and the coating state is improved. Because the low refractive index optical fiber coating is basically coated on the inner cladding of the optical fiber, the outer coating is coated immediately after the optical fiber coating is cured, the outer coating is of an epoxy acrylate structure, the strength is high, the weather resistance is strong, and the inner coating is fully protected by nitrogen during the curing process, and the oxygen polymerization inhibition effect is small, so that the relevance of the polymerizable monomer with the effect of reducing the oxygen polymerization inhibition effect as the design aim to the background technical scheme is not great.
A fluorine-containing photoinitiator successfully synthesized by reaction with a fluoroalcohol is described in patent CN15016228A and is used in polyurethane acrylate photoresists. The method uses one of 2,3, 4, 5-octafluoro-1-amyl alcohol, perfluorodecyl alcohol, perfluorohexyl ethyl alcohol and tetrafluoropropanol as the fluorine alcohol, wherein the perfluorohexyl ethyl alcohol has higher fluorine content, so that the fluorine content of the initiator can be obviously improved, but the photoinitiator described in the patent is a single-component modified fluorine initiator, and the modified initiator is in a solid powder state. Because the prepolymer resin of the low-refractive-index optical fiber coating is a solvent-free system and has larger viscosity, the system is poorer in miscibility in the mixing process of the prepolymer resin and the solid-state initiator, the phenomena of turbidity, reduced transparency and the like appear after the mixture, the dispersion effect of the solid initiator in the system is poorer, long-time dissolution is required, the film forming effect is uneven due to poor initiation rate in curing is extremely easy to appear, the curing process cannot be controlled accurately, and the coating process of the optical fiber coating is obviously influenced. The related fluorine modified initiators described in this patent do not solve the problems associated with the background.
Disclosure of Invention
The invention aims to prepare a compound photoinitiator for low-refractive-index optical fiber coating, the synthesis method of the initiator is simple, the system is a compound of an initiator main body with high fluorine content and a fluorine-containing acrylate monomer, the compound initiator is in a liquid state, the refractive index is low, the compound initiator can be dynamically adjusted according to requirements, the fluorine content is high, the compound photoinitiator can be mixed and dissolved with the low-refractive-index optical fiber coating according to any proportion, the mixing effect is excellent, the dispersion state is good, the yellowing effect in the curing process of the initiator is smaller, the activity is higher, and the initiation efficiency is excellent. Can be widely applied to initiator combinations of low refractive index optical fiber coatings.
The invention provides a compound photoinitiator for a low-refractive-index optical fiber coating, which comprises the following components in percentage by mass:
40% -65% of main body substance of fluorine-containing initiator,
20 to 45 percent of fluorine-containing acrylic ester,
12-20% of 2-hydroxy-2-methyl-1-phenylpropiophenone (1173D);
the main substance of the fluorine-containing initiator comprises the following components in percentage by mass:
the perfluoro acrylic ester is one or more of tridecyl methacrylate (G06 b), trifluoroethyl methacrylate (G03) and tridecyl acrylate (G06 c)
The second aspect provides a method for preparing the compound photoinitiator for the low refractive index optical fiber coating, which comprises the following steps:
comprises the steps of,
(1) Preparing main substances of a fluorine-containing initiator, weighing raw materials according to a proportion, heating triphenylmethane triisocyanate at 30 ℃ for 30min until the triphenylmethane triisocyanate can flow, then dropwise adding the raw materials into a three-mouth bottle filled with an acetone solution of 1-hydroxy-cyclohexyl benzophenone (acetone does not participate in the reaction) and dibutyltin dilaurate, reacting at 50 ℃ until the NCO content is not changed after the dripping is finished, dropwise adding perfluorohexyl ethyl alcohol into the system, dropwise adding the system in a nitrogen environment, keeping the temperature for 50 ℃ until the NCO content of the system is not changed, and obtaining the main substances of the fluorine-containing initiator;
(2) The preparation of the compound photoinitiator for the low-refractive-index optical fiber coating comprises the following steps: mixing the main body substance of the fluorine-containing initiator prepared in the step (1), fluorine-containing acrylic ester and 2-hydroxy-2-methyl-1-phenyl acetone in a light-proof beaker according to a proportion, uniformly stirring, removing acetone by using a decompression device, and enabling the acetone not to participate in the reaction to obtain the compound photoinitiator.
The beneficial effects of the invention are as follows:
the invention prepares a compound photoinitiator for a low-refractive-index optical fiber coating. The material has lower refractive index, good compatibility with low refractive index optical fiber coating, high curing efficiency and adjustable refractive index, and can be used as a low refractive index temperature-resistant optical fiber coating initiator.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, based on the examples herein, which are within the scope of the invention, will be within the purview of one of ordinary skill in the art without the exercise of inventive faculty.
Embodiment one:
preparing a main substance of a fluorine-containing initiator:
after the completion of the dropwise addition, 30g of triphenylmethane triisocyanate which can flow after heating at 30 ℃ for 30min is dropwise added into a three-mouth bottle containing 25g of a solution consisting of 184 and 100g of acetone and 0.1g of DBTDL, the reaction is carried out at 50 ℃ until the NCO content of the measurement system is unchanged, 45g of S104 is dropwise added into the system, the environment of all Cheng Danqi is completely reserved, the dropwise addition is completed for about 1h, and the reaction is carried out at 50 ℃ until the NCO content of the measurement system is unchanged. Stopping the reaction to obtain the main body substance FY-1 of the fluorine-containing initiator, and sealing and shading for storage.
The preparation method of the compound photoinitiator comprises the following steps:
50gFY-1, 30g G06b,15g1173D are mixed in a light-resistant beaker, stirred uniformly, and acetone is removed by using a decompression device to obtain the compound photoinitiator FYJ-1.
Embodiment two:
preparing a main substance of a fluorine-containing initiator:
after the dripping is finished, 50g of S104 is dripped into the system, the environment is full Cheng Danqi, the dripping is finished about 1 hour, and the temperature is kept at 50 ℃ until the NCO content of the system is not changed. Stopping the reaction to obtain the main body substance FY-2 of the fluorine-containing initiator, and sealing and shading for storage.
The preparation method of the compound photoinitiator comprises the following steps:
40gFY-2, 20g G03 and 14g1173D are mixed in a light-proof beaker, stirred uniformly and acetone is removed by using a decompression device, so as to obtain the compound photoinitiator FYJ-2.
Embodiment III:
preparing a main substance of a fluorine-containing initiator:
after the dripping is finished, reacting at 50 ℃ until the NCO content of the measuring system is unchanged, dripping 40g of S104 into the system, and completely Cheng Danqi, wherein the dripping is finished for about 1 hour, and reacting at 50 ℃ until the NCO content of the measuring system is unchanged. Stopping the reaction to obtain the main body substance FY-3 of the fluorine-containing initiator, and sealing and shading for storage.
The preparation method of the compound photoinitiator comprises the following steps:
50gFY-3, 25g G06c,13g1173D are mixed in a light-proof beaker, stirred uniformly and acetone is removed by using a decompression device to obtain the compound photoinitiator FYJ-3.
And (3) detecting the performance of the compound initiator:
1. refractive index detection:
refractive indices of the three built-up photoinitiators in the examples were measured using an abbe refractometer, environmental conditions: 25 DEG C
| Examples numbering | FYJ-1 | FYJ-2 | FYJ-3 |
| Refractive index/25 DEG C | 1.371 | 1.376 | 1.368 |
2. Compatibility detection
The sample FB-1 (polyacrylate type) of the low refractive index optical fiber coating without the initiator, FB-2 (polyurethane type) and the photoinitiator of the example are mixed, the addition amount of the example is 1 percent, 1.5 percent and 2 percent of the sample amount, and the compatibility of the comparative example and the low refractive index optical fiber coating is achieved.
3. Curing efficiency detection
The sample FB-1 and the sample were mixed according to a ratio of 1.5% to form a low refractive index optical fiber coating, the coating was applied to one side of a glass slide under a nitrogen protection environment for curing, and the cured state of the coating was tested and compared with the sample FBB-1 of the low refractive index optical fiber coating using a conventional initiator.
It can be seen that the compound photoinitiator prepared by the invention has the characteristics of low refractive index, good compatibility and high curing efficiency. Can be used as a special initiator to be applied to the preparation of the fluorine-containing optical fiber coating with low refractive index. The present disclosure has been described with respect to the above-described embodiments, however, the above-described embodiments are merely examples of implementation of the present disclosure. It must be noted that the disclosed embodiments do not limit the scope of the present disclosure. Rather, the foregoing is considered to be illustrative, and it is to be understood that the invention is not limited to the specific details disclosed herein.
Claims (1)
1. The compound photoinitiator for the low-refractive-index optical fiber coating is characterized by comprising the following components in percentage by mass:
40-65% of main substance of fluorine-containing initiator,
20-45% of fluorine-containing acrylic ester,
12% -20% of 2-hydroxy-2-methyl-1-phenylpropionic acid;
the main substance of the fluorine-containing initiator comprises the following components in percentage by mass:
perfluorohexyl ethyl alcohol 30-55%
15-35% of 1-hydroxy-cyclohexyl benzophenone
15-40% of triphenylmethane triisocyanate
0.1 to 0.3 percent of dibutyl tin dilaurate
The fluorine-containing acrylic ester is one or more of tridecyl methacrylate, trifluoroethyl methacrylate and tridecyl acrylate;
the preparation method of the compound photoinitiator for the low-refractive-index optical fiber coating comprises the following steps of,
(1) Preparing main substances of a fluorine-containing initiator, weighing raw materials according to a proportion, heating triphenylmethane triisocyanate at 30 ℃ for 30min until the triphenylmethane triisocyanate can flow, then dropwise adding the triphenylmethane triisocyanate into a three-mouth bottle filled with a mixed solution of an acetone solution of 1-hydroxy-cyclohexyl benzophenone and dibutyltin dilaurate, reacting at 50 ℃ until the NCO content is not changed after the dropwise adding is finished, dropwise adding perfluorohexyl ethyl alcohol into the system, dropwise adding the system in a nitrogen environment in the whole course, keeping the temperature at 50 ℃ after the dropwise adding is finished, reacting until the NCO content of the system is not changed, and obtaining the main substances of the fluorine-containing initiator, and sealing and shading for storage;
(2) The preparation of the compound photoinitiator for the low-refractive-index optical fiber coating comprises the following steps: mixing the main body substance of the fluorine-containing initiator prepared in the step (1), fluorine-containing acrylic ester and 2-hydroxy-2-methyl-1-phenyl acetone in a light-proof beaker according to a proportion, uniformly stirring, and removing the acetone by using a decompression device to obtain the compound photoinitiator.
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| CN202211322595.3A CN115651099B (en) | 2022-10-27 | 2022-10-27 | Preparation method of compound photoinitiator for low-refractive-index optical fiber coating |
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| CN202211322595.3A CN115651099B (en) | 2022-10-27 | 2022-10-27 | Preparation method of compound photoinitiator for low-refractive-index optical fiber coating |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101967342A (en) * | 2010-10-19 | 2011-02-09 | 中山大桥化工集团有限公司 | Ultraviolet curing coating |
| CN104845521A (en) * | 2015-06-15 | 2015-08-19 | 张家港康得新光电材料有限公司 | UV curing coating, wear-resistant and antifouling coating layer and mobile phone protection film containing wear-resistant and antifouling coating layer |
| CN115016228A (en) * | 2022-05-10 | 2022-09-06 | 常州大学 | Polyurethane acrylate photoresist and preparation method thereof |
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- 2022-10-27 CN CN202211322595.3A patent/CN115651099B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101967342A (en) * | 2010-10-19 | 2011-02-09 | 中山大桥化工集团有限公司 | Ultraviolet curing coating |
| CN104845521A (en) * | 2015-06-15 | 2015-08-19 | 张家港康得新光电材料有限公司 | UV curing coating, wear-resistant and antifouling coating layer and mobile phone protection film containing wear-resistant and antifouling coating layer |
| CN115016228A (en) * | 2022-05-10 | 2022-09-06 | 常州大学 | Polyurethane acrylate photoresist and preparation method thereof |
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