CN109609021A - A kind of cured high refractive index polyurethane resin coating of ultraviolet light and preparation method thereof - Google Patents
A kind of cured high refractive index polyurethane resin coating of ultraviolet light and preparation method thereof Download PDFInfo
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- CN109609021A CN109609021A CN201811496367.1A CN201811496367A CN109609021A CN 109609021 A CN109609021 A CN 109609021A CN 201811496367 A CN201811496367 A CN 201811496367A CN 109609021 A CN109609021 A CN 109609021A
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- refractive index
- ultraviolet light
- high refractive
- polyurethane resin
- resin coating
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/58—Epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/675—Low-molecular-weight compounds
- C08G18/6755—Unsaturated carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The invention discloses cured high refractive index polyurethane resin coatings of a kind of ultraviolet light and preparation method thereof, which is grouped as by the group of following weight percent content: ultraviolet curing urethane resin 59-70%, reactive diluent 29.5-40%, photoinitiator 0.5-1%；The ultraviolet curing urethane resin is grouped as by the group of following weight percent content: epoxy resin 70-80%, IPDI 10-15%, acrylic acid 8-14%, catalyst 0.5-1%, polymerization inhibitor 0.5-1%.The present invention passes through control parameter and raw material proportioning, refractive index is high before and after the paint solidification obtained after ultraviolet curing urethane resin and reactive diluent and the photoinitiator cooperation of synthesis, with good stability, film-forming intensity significantly improves and does not influence other performances of resin.
Description
Technical field
The present invention relates to a kind of coating, and in particular to a kind of cured high refractive index polyurethane resin coating of ultraviolet light and its
Preparation method.
Background technique
The refractive index of the resin containing polyurethane type is generally all very low, especially using containing double during synthesis of polyurethane
The resin of the group of key has a great impact to the refractive index of resin before and after its film-forming.The activity dilution of photocuring is added
Agent can then make the reduction of cured film refractive index, reduce resin physical property.Refractive index is low, and to will affect resin special in optical fiber, optical cable etc.
The application of industry field aviation brings limitation, therefore need to develop a kind of poly- to improve for ultraviolet light solidification high refractive index polyurethane
The refractive index of urethane.
There are two types of the main methods for solving the problems, such as this at present, first is that the work of high refractivity is added after the resin of synthesis photocuring
Property diluent achievees the purpose that reinforced resin refractive index after physical agitation, but since photocuring amount of diluent is excessively high in turn
The intensity of resin is influenced, and extends ultraviolet light curing time；Second is that being synthesized in the synthesis process using the monomer of high refractive index
Polyurethane resin, but the resin of this method synthesis and the compatibility of reactive diluent are poor, and just face is tacky for solidification rear film, resin point
Son amount is unevenly distributed.
Summary of the invention
The purpose of the present invention is to solve the technical problems existing in the prior art, provide a kind of film-forming front and back folding
Penetrate the cured high refractive index polyurethane resin coating of ultraviolet light that rate is high, stability is good and film-forming intensity is high.
Another object of the present invention is to provide a kind of cured high refractive index polyurethane resin coatings of ultraviolet light
Preparation method.
In order to achieve the above object, the invention adopts the following technical scheme: a kind of poly- ammonia of the cured high refractive index of ultraviolet light
Ester resin paint is grouped as by the group of following weight percent content: ultraviolet curing urethane resin 59-70%, activity dilution
Agent 29.5-40%, photoinitiator 0.5-1%；The ultraviolet curing urethane resin by following weight percent content component
Composition: epoxy resin 70-80%, IPDI 10-15%, acrylic acid 8-14%, catalyst 0.5-1%, polymerization inhibitor 0.5-1%.
Further, the reactive diluent is one in TPGDA, EGPMA, HDDA, DPGDA, EOEOEA, PDDA
Kind.
Further, the photoinitiator is one of Darocure 1173, Irgacure 184.
Further, the catalyst is tetrabutylammonium bromide.
Further, the polymerization inhibitor is 2,6- di-tert-butylphenol.
A kind of preparation method of the cured high refractive index polyurethane resin coating of ultraviolet light, method includes the following steps:
A, epoxy resin, IPDI are added in reactor, are warming up to 100-105 DEG C, catalyst, lasting control temperature to 105 is added
DEG C stirring 2h, reaction to acid value be less than 3mg, be cooled to 80 DEG C be added dropwise acrylic acid and polymerization inhibitor mixture 30min, be warming up to 95
DEG C reaction 1h, then is warming up to 105 DEG C of reaction 2h, reaction to acid value 3mg is cooled to 80 DEG C, discharges and the poly- ammonia of ultraviolet light solidification is made
Ester resin；
B, the ultraviolet curing urethane resin of synthesis is mixed evenly with reactive diluent and photoinitiator to get ultraviolet
The high refractive index polyurethane resin coating of photocuring.
The present invention has the advantages that the cured high refractive index polyurethane tree of ultraviolet light of the present invention compared with the prior art
Grease coating material is mainly made of ultraviolet curing urethane resin, reactive diluent, photoinitiator, wherein ultraviolet curing urethane
Resin is made of epoxy resin, IPDI, acrylic acid, catalyst, polymerization inhibitor, and the present invention is closed by control parameter and raw material proportioning
At ultraviolet curing urethane resin and reactive diluent and photoinitiator cooperation after refractive index before and after obtained paint solidification
Height, has good stability, and film-forming intensity significantly improves and do not influence other performances of resin.
Specific embodiment
The present invention is further explained in the light of specific embodiments.
Embodiment 1
A kind of cured high refractive index polyurethane resin coating of ultraviolet light, is grouped as by the group of following weight percent content: purple
Outer light-cured polyurethane resin 60%, TPGDA 39%, Darocure 1173 (HMPP) 1%；The ultraviolet curing urethane tree
Rouge is grouped as by the group of following weight percent content: epoxy resin 70%, IPDI 15%, acrylic acid 14%, tetrabutylammonium bromide
0.5%, 2,6- di-tert-butylphenol 0.5%.
The preparation method of the cured high refractive index polyurethane resin coating of the ultraviolet light, method includes the following steps:
A, epoxy resin, IPDI are added in reactor, are warming up to 100 DEG C, tetrabutylammonium bromide is added, lasting control temperature is extremely
105 DEG C of stirring 2h, reaction to acid value are less than 3mg, are cooled to 80 DEG C of dropwise addition acrylic acid and 2, the mixture of 6- di-tert-butylphenol
30min is warming up to 95 DEG C of reaction 1h, then is warming up to 105 DEG C of reaction 2h, reaction to acid value 3mg, is cooled to 80 DEG C, discharging is made
Ultraviolet curing urethane resin；
B, the ultraviolet curing urethane resin of synthesis and TPGDA and Darocure 1173 (HMPP) are mixed evenly, i.e.,
Obtain the cured high refractive index polyurethane resin coating of ultraviolet light.
Coating after uniformly, ultraviolet light solidify 15s, test its performance: viscosity 4800mPa.s, and refractive index (25 DEG C) 1.53 is broken
Resistance to spalling 18MPa, elongation at break 13%.
Embodiment 2
A kind of cured high refractive index polyurethane resin coating of ultraviolet light, is grouped as by the group of following weight percent content: purple
Outer light-cured polyurethane resin 70%, EGPMA 29.5%, Irgacure 184 (HCPK) 0.5%；The ultraviolet curing urethane
Resin is grouped as by the group of following weight percent content: epoxy resin 80%, IPDI 10%, acrylic acid 8%, tetrabutyl phosphonium bromide
Ammonium 1%, 2,6- di-tert-butylphenol 1%.
The preparation method of the cured high refractive index polyurethane resin coating of the ultraviolet light, method includes the following steps:
A, epoxy resin, IPDI are added in reactor, are warming up to 105 DEG C, tetrabutylammonium bromide is added, lasting control temperature is extremely
105 DEG C of stirring 2h, reaction to acid value are less than 3mg, are cooled to 80 DEG C of dropwise addition acrylic acid and 2, the mixture of 6- di-tert-butylphenol
30min is warming up to 95 DEG C of reaction 1h, then is warming up to 105 DEG C of reaction 2h, reaction to acid value 3mg, is cooled to 80 DEG C, discharging is made
Ultraviolet curing urethane resin；
B, the ultraviolet curing urethane resin of synthesis and EGPMA and Irgacure 184 (HCPK) are mixed evenly, i.e.,
Obtain the cured high refractive index polyurethane resin coating of ultraviolet light.
Coating after uniformly, ultraviolet light solidify 15s, test its performance: viscosity 4200mPa.s, and refractive index (25 DEG C) 1.50 is broken
Resistance to spalling 16MPa, elongation at break 10%.
Embodiment 3
A kind of cured high refractive index polyurethane resin coating of ultraviolet light, is grouped as by the group of following weight percent content: purple
Outer light-cured polyurethane resin 65%, HDDA 34.2%, Darocure 1173 (HMPP) 0.8%；The ultraviolet curing urethane
Resin is grouped as by the group of following weight percent content: epoxy resin 75%, IPDI 12%, acrylic acid 11.5%, tetrabutyl bromine
Change ammonium 0.5%, 2,6- di-tert-butylphenol 1%.
The preparation method of the cured high refractive index polyurethane resin coating of the ultraviolet light, method includes the following steps:
A, epoxy resin, IPDI are added in reactor, are warming up to 100 DEG C, tetrabutylammonium bromide is added, lasting control temperature is extremely
105 DEG C of stirring 2h, reaction to acid value are less than 3mg, are cooled to 80 DEG C of dropwise addition acrylic acid and 2, the mixture of 6- di-tert-butylphenol
30min is warming up to 95 DEG C of reaction 1h, then is warming up to 105 DEG C of reaction 2h, reaction to acid value 3mg, is cooled to 80 DEG C, discharging is made
Ultraviolet curing urethane resin；
B, the ultraviolet curing urethane resin of synthesis and HDDA and Darocure 1173 (HMPP) are mixed evenly, i.e.,
Obtain the cured high refractive index polyurethane resin coating of ultraviolet light.
Coating after uniformly, ultraviolet light solidify 15s, test its performance: viscosity 5100mPa.s, and refractive index (25 DEG C) 1.54 is broken
Resistance to spalling 12MPa, elongation at break 14%.
Embodiment 4
A kind of cured high refractive index polyurethane resin coating of ultraviolet light, is grouped as by the group of following weight percent content: purple
Outer light-cured polyurethane resin 63%, DPGDA 36%, Irgacure 184 (HCPK) 1%；The ultraviolet curing urethane resin
It is grouped as by the group of following weight percent content: epoxy resin 76%, IPDI 12.5%, acrylic acid 10%, tetrabutylammonium bromide
1%, 2,6- di-tert-butylphenol 0.5%.
The preparation method of the cured high refractive index polyurethane resin coating of the ultraviolet light, method includes the following steps:
A, epoxy resin, IPDI are added in reactor, are warming up to 105 DEG C, tetrabutylammonium bromide is added, lasting control temperature is extremely
105 DEG C of stirring 2h, reaction to acid value are less than 3mg, are cooled to 80 DEG C of dropwise addition acrylic acid and 2, the mixture of 6- di-tert-butylphenol
30min is warming up to 95 DEG C of reaction 1h, then is warming up to 105 DEG C of reaction 2h, reaction to acid value 3mg, is cooled to 80 DEG C, discharging is made
Ultraviolet curing urethane resin；
B, the ultraviolet curing urethane resin of synthesis and DPGDA and Irgacure 184 (HCPK) are mixed evenly, i.e.,
Obtain the cured high refractive index polyurethane resin coating of ultraviolet light.
Coating after uniformly, ultraviolet light solidify 15s, test its performance: viscosity 4600mPa.s, and refractive index (25 DEG C) 1.52 is broken
Resistance to spalling 14MPa, elongation at break 12%.
Embodiment 5
A kind of cured high refractive index polyurethane resin coating of ultraviolet light, is grouped as by the group of following weight percent content: purple
Outer light-cured polyurethane resin 59%, EOEOEA 40%, Darocure 1173 (HMPP) 1%；The ultraviolet curing urethane tree
Rouge is grouped as by the group of following weight percent content: epoxy resin 73%, IPDI 13%, acrylic acid 12%, tetrabutylammonium bromide
1%, 2,6- di-tert-butylphenol 1%.
The preparation method of the cured high refractive index polyurethane resin coating of the ultraviolet light, method includes the following steps:
A, epoxy resin, IPDI are added in reactor, are warming up to 100 DEG C, tetrabutylammonium bromide is added, lasting control temperature is extremely
105 DEG C of stirring 2h, reaction to acid value are less than 3mg, are cooled to 80 DEG C of dropwise addition acrylic acid and 2, the mixture of 6- di-tert-butylphenol
30min is warming up to 95 DEG C of reaction 1h, then is warming up to 105 DEG C of reaction 2h, reaction to acid value 3mg, is cooled to 80 DEG C, discharging is made
Ultraviolet curing urethane resin；
B, the ultraviolet curing urethane resin of synthesis and EOEOEA and Darocure 1173 (HMPP) are mixed evenly,
Up to the cured high refractive index polyurethane resin coating of ultraviolet light.
Coating after uniformly, ultraviolet light solidify 15s, test its performance: viscosity 4700mPa.s, and refractive index (25 DEG C) 1.50 is broken
Resistance to spalling 13MPa, elongation at break 10%.
Embodiment 6
A kind of cured high refractive index polyurethane resin coating of ultraviolet light, is grouped as by the group of following weight percent content: purple
Outer light-cured polyurethane resin 66%, PDDA 33%, Irgacure 184 (HCPK) 1%；The ultraviolet curing urethane resin
It is grouped as by the group of following weight percent content: epoxy resin 73%, IPDI 13%, acrylic acid 12%, tetrabutylammonium bromide
1%, 2,6- di-tert-butylphenol 1%.
The preparation method of the cured high refractive index polyurethane resin coating of the ultraviolet light, method includes the following steps:
A, epoxy resin, IPDI are added in reactor, are warming up to 105 DEG C, tetrabutylammonium bromide is added, lasting control temperature is extremely
105 DEG C of stirring 2h, reaction to acid value are less than 3mg, are cooled to 80 DEG C of dropwise addition acrylic acid and 2, the mixture of 6- di-tert-butylphenol
30min is warming up to 95 DEG C of reaction 1h, then is warming up to 105 DEG C of reaction 2h, reaction to acid value 3mg, is cooled to 80 DEG C, discharging is made
Ultraviolet curing urethane resin；
B, by the ultraviolet curing urethane resin of synthesis and PDDA and Irgacure 184 (HCPK) be mixed evenly to get
The cured high refractive index polyurethane resin coating of ultraviolet light.
Coating after uniformly, ultraviolet light solidify 15s, test its performance: viscosity 4500mPa.s, and refractive index (25 DEG C) 1.53 is broken
Resistance to spalling 15MPa, elongation at break 11%.
Claims (6)
1. a kind of cured high refractive index polyurethane resin coating of ultraviolet light, it is characterised in that: by following weight percent content
Group be grouped as: ultraviolet curing urethane resin 59-70%, reactive diluent 29.5-40%, photoinitiator 0.5-1%；It is described
Ultraviolet curing urethane resin is grouped as by the group of following weight percent content: epoxy resin 70-80%, IPDI 10-15%
, acrylic acid 8-14%, catalyst 0.5-1%, polymerization inhibitor 0.5-1%.
2. the cured high refractive index polyurethane resin coating of a kind of ultraviolet light according to claim 1, it is characterised in that: institute
The reactive diluent stated is one of TPGDA, EGPMA, HDDA, DPGDA, EOEOEA, PDDA.
3. the cured high refractive index polyurethane resin coating of a kind of ultraviolet light according to claim 1, it is characterised in that: institute
Stating photoinitiator is one of Darocure 1173, Irgacure 184.
4. the cured high refractive index polyurethane resin coating of a kind of ultraviolet light according to claim 1, it is characterised in that: institute
Stating catalyst is tetrabutylammonium bromide.
5. the cured high refractive index polyurethane resin coating of a kind of ultraviolet light according to claim 1, it is characterised in that: institute
Stating polymerization inhibitor is 2,6- di-tert-butylphenol.
6. a kind of preparation method of the cured high refractive index polyurethane resin coating of ultraviolet light, it is characterised in that this method include with
Lower step:
A, epoxy resin, IPDI are added in reactor, are warming up to 100-105 DEG C, catalyst, lasting control temperature to 105 is added
DEG C stirring 2h, reaction to acid value be less than 3mg, be cooled to 80 DEG C be added dropwise acrylic acid and polymerization inhibitor mixture 30min, be warming up to 95
DEG C reaction 1h, then is warming up to 105 DEG C of reaction 2h, reaction to acid value 3mg is cooled to 80 DEG C, discharges and the poly- ammonia of ultraviolet light solidification is made
Ester resin；
B, the ultraviolet curing urethane resin of synthesis is mixed evenly with reactive diluent and photoinitiator to get ultraviolet
The high refractive index polyurethane resin coating of photocuring.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811496367.1A CN109609021A (en) | 2018-12-07 | 2018-12-07 | A kind of cured high refractive index polyurethane resin coating of ultraviolet light and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811496367.1A CN109609021A (en) | 2018-12-07 | 2018-12-07 | A kind of cured high refractive index polyurethane resin coating of ultraviolet light and preparation method thereof |
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| CN201811496367.1A Pending CN109609021A (en) | 2018-12-07 | 2018-12-07 | A kind of cured high refractive index polyurethane resin coating of ultraviolet light and preparation method thereof |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60255818A (en) * | 1984-05-21 | 1985-12-17 | ディーエスエム ナムローゼ フェンノートシャップ | Radiation-curable unsaturated polyurethane resin |
| CN104877544A (en) * | 2015-05-12 | 2015-09-02 | 上海维凯光电新材料有限公司 | UV photo-curing elastic self-repairing brightening paint composition |
| CN105131802A (en) * | 2015-09-23 | 2015-12-09 | 上海贻赛新材料科技有限公司 | High-flexibility UV coating and preparation method thereof |
-
2018
- 2018-12-07 CN CN201811496367.1A patent/CN109609021A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60255818A (en) * | 1984-05-21 | 1985-12-17 | ディーエスエム ナムローゼ フェンノートシャップ | Radiation-curable unsaturated polyurethane resin |
| CN104877544A (en) * | 2015-05-12 | 2015-09-02 | 上海维凯光电新材料有限公司 | UV photo-curing elastic self-repairing brightening paint composition |
| CN105131802A (en) * | 2015-09-23 | 2015-12-09 | 上海贻赛新材料科技有限公司 | High-flexibility UV coating and preparation method thereof |
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Application publication date: 20190412 |
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