CN101638553B - Ultraviolet curing coating - Google Patents
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- CN101638553B CN101638553B CN2008101353876A CN200810135387A CN101638553B CN 101638553 B CN101638553 B CN 101638553B CN 2008101353876 A CN2008101353876 A CN 2008101353876A CN 200810135387 A CN200810135387 A CN 200810135387A CN 101638553 B CN101638553 B CN 101638553B
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Abstract
The invention relates to an ultraviolet curing coating. The coating comprises high-functionality polyurethane acrylic resin, a medium-functionality acrylic monomer, a photoinitiator and solvent, and comprises or does not comprise medium-functionality polyurethane acrylic resin and an auxiliary agent. The coating also comprises epoxy acrylic resin and a metal salt acrylate oligomer. A coat formed by the ultraviolet curing coating has the advantages of strong scratch-resistant capacity, high hardness and good wear resistance.
Description
Technical field
The present invention relates to a kind of ultraviolet-curing paint.
Background technology
Along with the develop rapidly of the communication apparatus, pocket electronic products such as mobile phone, MP3 are all the fashion, and the image display of making man-machine interface adopts transparent synthesized polymer material like PC (polycarbonate), PMMA (polymethylmethacrylate), PET (polyester) etc.In actual application, can cause scratch, the wearing and tearing on surface, this just need be at the water white paint of surface-coated one deck, and the performance with aspects such as the hardness that improves the surface, wear-resisting, anti-cuts reaches the surperficial effect of protection.But the coat of painting on surface comes off easily on the one hand, can not protect body material for a long time effectively; On the other hand, the coating of coat of painting makes the making of image display become loaded down with trivial details with dry, thereby has increased production cost.
Ultraviolet-curing paint is a kind of environment-friendly and energy-efficient coating of the exploitation sixties in 20th century, and the seventies, China began to set foot in this technical field, just obtained tremendous development after the nineties.Ultraviolet-curing paint gets final product fast setting under UV-irradiation, not only curing speed is fast, and compares with heat curing coating and also to save the energy.At present, it is not only widely applied on timber, metal, plastics, paper, leather, but also on materials such as optical fiber, PC board, electronic devices and components encapsulation successful Application.But conventional ultraviolet curable coating hardness is relatively poor, thereby not wear-resisting wiping, is prone to scratch.
Summary of the invention
The objective of the invention is to overcome the low shortcoming of coating hardness that the ultraviolet-curing paint of prior art forms, a kind of ultraviolet-curing paint that can form high hardness spray coating is provided.
The invention provides a kind of ultraviolet-curing paint; This coating contains high-functionality polyurethane vinyl resin, middle functionality acrylate monomer, light trigger and solvent; Functionality polyurethane acrylic resin and auxiliary agent in containing or not containing, wherein, this coating also contains epoxy acrylic resin and metal-salt acrylic ester oligomer; Wherein, said high-functionality polyurethane vinyl resin molecule contains 6-12 carbon-carbon double bond; Functionality acrylate monomer molecule contains 2-3 carbon-carbon double bond in said; Functionality polyurethane acrylic resin molecule contains 2-4 carbon-carbon double bond in said.
The coating that forms with ultraviolet-curing paint of the present invention has the advantage that the scratch resistance ability is strong, hardness is high and wear resisting property is good.
Embodiment
Ultraviolet-curing paint provided by the invention contains high-functionality polyurethane vinyl resin, middle functionality acrylate monomer, light trigger and solvent; Functionality polyurethane acrylic resin and auxiliary agent in containing or not containing; Wherein, This coating also contains epoxy acrylic resin and metal-salt acrylic ester oligomer, and wherein, said high-functionality polyurethane vinyl resin molecule contains 6-12 carbon-carbon double bond; Functionality acrylate monomer molecule contains 2-3 carbon-carbon double bond in said; Functionality polyurethane acrylic resin molecule contains 2-4 carbon-carbon double bond in said.
Wherein, said high-functionality polyurethane vinyl resin molecule can contain 6-12 carbon-carbon double bond, and under the preferable case, said high-functionality polyurethane vinyl resin contains 6 or 9 carbon-carbon double bonds.Said high-functionality polyurethane vinyl resin can prepare through the preparation method of routine, also can be commercially available, for example, the PRO30053 of SARTOMER company (6 carbon-carbon double bonds), CN9010 (6 carbon-carbon double bonds) and CN9013 (9 carbon-carbon double bonds).
Functionality acrylate monomer molecule can comprise difunctionality and three-functionality-degree acrylate monomer in said.Wherein, Said functionality refers to the number of the formed functional group of vinylformic acid in the acrylate monomer molecule, and promptly said difunctionality and three-functionality-degree acrylate monomer refer to that respectively the number of the formed functional group of vinylformic acid in the acrylate monomer molecule is two and three.The difunctionality acrylate monomer can be selected from tri (propylene glycol) diacrylate (TPGDA), 1; In 6 hexanediyl esters (HDDA), 1,6 pinakon dimethyl-diacrylate (HDDMA), propylene glycol diacrylate and the polyethyleneglycol diacrylate one or more.The three-functionality-degree acrylate monomer can be selected from one or more in Viscoat 295 (TMPTA), Viscoat 295, trimethylol propane trimethyl triacrylate (TMPTMA) and the pentaerythritol triacrylate.Under the preferable case, said middle functionality acrylate monomer molecule is the three-functionality-degree acrylate monomer, more preferably TMPTA and/or TMPTMA.
Said epoxy acrylic resin is preferably the epoxy acrylic resin of difunctionality, and promptly the number of the formed functional group of vinylformic acid is two in said epoxy acrylic resin.The epoxy acrylic resin of said difunctionality is can be through known compound method synthetic or be commercially available, for example, and one or more among CN104, CN104A60 and the CN120 that can produce for SARTOMER company.
Said metal-salt acrylic ester oligomer can be in zinc salt urethane acrylate oligomer, zinc salt polyester acrylate oligomer, zinc salt epoxy acrylate oligomer, sodium salt urethane acrylate oligomer, sodium salt polyester acrylate oligomer, the sodium salt epoxy acrylate oligomer one or more, preferred zinc salt urethane acrylate oligomer.The number-average molecular weight of said metal-salt acrylic ester oligomer can be 1500-10000, and functionality can be 2-4.Said metal-salt acrylic ester oligomer can prepare through the method for routine; For example in urethane acrylate oligomer, polyester acrylate and the epoxy acrylate one or more are obtained with the metal-salt half ester reaction that contains hydroxyl, perhaps POLYMETHYLENE POLYPHENYLISOCYANATE, the propenoate that contains hydroxyl are obtained with the metal-salt half ester reaction that contains hydroxyl.The said metal-salt half ester that contains hydroxyl can be through making MOX and the half ester reaction that contains hydroxyl and carboxyl, and said MOX can be preferably ZnO for the oxide compound of metals such as Zn, Li, Na, K, Ca, Mg.More detailed compound method can be with reference to WO 02/057331.Said metal-salt acrylic ester oligomer can also be commercially available, and for example, can be preferably CN2401 and/or CN2400 for the metal-salt acrylic ester oligomer of SARTOMER company production.
Functionality polyurethane acrylic resin molecule can contain 2-4 carbon-carbon double bond in said.Under the preferable case; Contain 2 carbon-carbon double bonds in the functionality polyurethane acrylic resin molecule in said; The functionality polyurethane acrylic resin can prepare through the preparation method of routine in said; Also can be commercially available, for example, can be the CN983 and/or the CN963A80 of SARTOMER company production.In order to improve the hardness of the ultraviolet curable coating that forms better, the weight ratio of said middle functionality polyurethane acrylic resin and said high-functionality polyurethane vinyl resin can be 1: 0.5-10 is preferably 1: 2-8.
Gross weight with coating is a benchmark, and the content of said high-functionality polyurethane vinyl resin can be 20-60 weight %, is preferably 25-45 weight %; The content of functionality acrylate monomer can be 5-20 weight % in said, is preferably 8-15 weight %; The content of said light trigger can be 0.5-5 weight %, is preferably 1-3 weight %; The content of said epoxy acrylic resin can be 5-30 weight %, is preferably 5-20 weight %; The content of said metal-salt acrylic ester oligomer can be 1-20 weight %, is preferably 5-15 weight %; The content of said solvent can be 15-65 weight %, is preferably 25-40 weight %; The content of functionality polyurethane acrylic resin can be 0-15 weight % in said, is preferably 1-10 weight %; The content of said auxiliary agent can be 0-8 weight %, is preferably 1-5 weight %.
According to ultraviolet-curing paint provided by the invention; Wherein, said light trigger can be 1-hydroxy-cyclohexyl benzophenone (184), 2,2-dimethyl--Alpha-hydroxy methyl phenyl ketone (1173) and (2; 4,6-trimethylbenzoyl) one or more in the diphenyl phosphine oxide (TPO).Under the preferable case, said light trigger is 184.
Said solvent can be selected from one or more in toluene, ETHYLE ACETATE, n-butyl acetate, isobutyl acetate, propyl acetate, ethanol, propyl carbinol, pimelinketone, YLENE, hexone, acetone, methylethylketone, butyl glycol ether, the Ucar 35 butyl ether.Under the preferable case; In order to improve the hardness of the ultraviolet curable coating that forms better; Said solvent is the mixture of ETHYLE ACETATE and/or n-butyl acetate and Virahol and/or propyl carbinol; Wherein, ETHYLE ACETATE and/or n-butyl acetate: the weight ratio of Virahol and/or propyl carbinol can be 1: 0.05-1 is preferably 1: 0.1-0.3.
According to ultraviolet-curing paint provided by the invention, wherein, said auxiliary agent can comprise one or more in flow agent, skimmer, dispersion agent and the wetting agent.
Said flow agent can variously can improve the flow leveling that is coated with rete behind the paint solidification for well known to a person skilled in the art; Increase the material of the smoothness and the feel that are coated with rete; For example, can be selected among EFKA3883, EFKA3886, EFKA3600, BYK366, BYK333, BYK307, DEGO410, DEGO435, DEGO432, the TEGO Flow300 one or more.Wherein EFKA series is Dutch Ai Fuka Company products, and BYK series is the BYK Company products, and DEGO series is the high Company products of German enlightening, and TEGO is the product of German TEGO company.Gross weight with coating is a benchmark, and the content of said flow agent can be 0-2 weight %, is preferably 0-1 weight %.
Said skimmer can be for well known to a person skilled in the art the various materials that can eliminate the bubble in the coating or reduce the bubble generation; For example; Can be selected from EFKA2022, EFKA2527, EFKA2040, BYK352, among BYK354, BYK357 and the TEGO Airex931 one or more.Gross weight with coating is a benchmark, and the content of said skimmer can be 0-2 weight %, is preferably 0-1.5 weight %.
Said dispersion agent can be for well known to a person skilled in the art the various materials that can improve the dispersion state of matrix resin in solvent in the coating; For example can select Kerper-602, Kerper-605 and the Kerper-630 of the U.S. Kerper company that is purchased for use, CFC-500HP, CFC-510, CFC-637 and the CFC-604S of French CFC company.Gross weight with coating is a benchmark, and the content of said dispersion agent can be 0-2 weight %, is preferably 0-1.5 weight %.
Said wetting agent can for example can be selected 8857A and Zonyl FSO-100 and the rising sun Xiao DP-10 of Subsidiary Company and the DP-20 of the E.I.Du Pont Company that is purchased for use for well known to a person skilled in the art the various tensio-active agents that are used for ultraviolet-curing paint.Gross weight with coating is a benchmark, and the content of said wetting agent can be 0-2 weight %, is preferably 0-1.5 weight %.
The preparation method of ultraviolet-curing paint of the present invention can proceed step by step mix disposable the mixing also of said high-functionality polyurethane vinyl resin, middle functionality acrylate monomer, epoxy acrylic resin, metal-salt acrylic ester oligomer, solvent and light trigger.Under preferable case, earlier light trigger is mixed with partial solvent, light trigger is fully dissolved, obtain containing the solution of light trigger; Then that high-functionality polyurethane vinyl resin, middle functionality acrylate monomer, epoxy acrylic resin and metal-salt acrylic ester oligomer and another part solvent is even, obtain the resinous principle slurries; The solution that then will contain light trigger mixes with the slurries that contain resinous principle, and it is even to add remaining solvent at last.Above-mentioned mixing is carried out usually at normal temperatures, in case of necessity, can mild heat to 30-60 ℃, mix quickening.
If when in said coating, also adding in the auxiliary agents such as flow agent, skimmer, dispersion agent and wetting agent one or more; Above-mentioned preparation method also is included in and adds before the remaining solvent; When the solution that will contain light trigger mixes with the slurries that contain resinous principle; Add in the above-mentioned various auxiliary agent one or more and uniform mixing again.Various auxiliary agents can add simultaneously also and can add step by step, and the order of adding does not have remarkable influence to the performance of coating of the present invention.
Coating provided by the present invention is suitable for the top coat of plastic basis material, like the top coat of the surface of shell of the display screen surface of electronic product, electronic product, toiletry bag casing etc.The application method of coating of the present invention is: after being coated to coating of the present invention on the base material; This base material that has applied coating was toasted 10-15 minute under 40-80 ℃ temperature; And adopt UV-irradiation 20-25 second, on base material, forming thickness is the coating of 10-15 micron.
Below, will be described in more detail the present invention through embodiment.
Embodiment 1
Present embodiment is explained coating provided by the invention and preparation method thereof.
Prepare coating as follows:
(1) with 1.5 gram light trigger 1-hydroxy-cyclohexyl benzophenones (CIBA IRGACURE company, 184) and 10 gram solvent (ETHYLE ACETATE: propyl carbinol weight ratio=1: 0.15) mix, be stirred to abundant dissolving;
(2) with 32 grams, six functionality urethane acrylate (SARTOMER companies; PRO30053), 8 gram Viscoat 295 (SARTOMER companies; SR351), 8 gram difunctionality epoxy acrylate (SARTOMER companies; CN120), 10 gram metal-salt acrylic ester oligomer (SARTOMER companies; CN2401) and 8 gram difunctionality polyurethane acrylate resins (SARTOMER company CN983) restrains solvent (ETHYLE ACETATE: propyl carbinol weight ratio=1: 0.15) mix at 40 ℃, stir with 25;
(3) product that step (1) and (2) is obtained mixes, and stirs;
(4) be cooled to 25 ℃, filter the slurries that obtain, to remove residue;
(5) continue to add 7.5 gram solvent (ETHYLE ACETATE: propyl carbinol weight ratio=1: 0.15), stir, obtain coating A1.
Embodiment 2
Present embodiment is explained coating provided by the invention and preparation method thereof.
With 2 gram light trigger 1-hydroxy-cyclohexyl benzophenones, 28 grams, nine functionality urethane acrylate (SARTOMER companies; CN9013), 12 gram trimethylolpropane trimethacrylate (SARTOMER companies; SR350), 6 gram difunctionality epoxy acrylates (SARTOMER company, CN104A60), 10 gram metal-salt acrylic ester oligomers (SARTOMER company, CN2400), 0.5 gram flow agent (TEGO company; TEGO Flow 300) and 1 gram skimmer (TEGO company; TEGO Airex 931) with 36.5 gram solvent (butylacetate: Virahol weight ratio=1: 0.2) mix, stir, obtain coating A2.
Embodiment 3
Present embodiment is explained coating provided by the invention and preparation method thereof.
Prepare coating as follows:
(1) with 2.5 gram light trigger 1-hydroxy-cyclohexyl benzophenones (CIBA IRGACURE company, 184) and 10 gram solvent (ETHYLE ACETATE: n-butyl acetate: propyl carbinol weight ratio=1: 1: 0.5) mix, be stirred to abundant dissolving;
(2) with 40 grams, six functionality urethane acrylate (SARTOMER companies; CN9010), 15 gram Viscoat 295 (SARTOMER companies; SR350), 6 gram difunctionality epoxy acrylate (SARTOMER companies; CN120), 5 gram metal-salt acrylic ester oligomer (SARTOMER companies; CN2401) and 2 gram difunctionality polyurethane acrylate resins (SARTOMER company CN983) restrains solvent (ETHYLE ACETATE: n-butyl acetate: propyl carbinol weight ratio=1: 1: 0.4) mix at 40 ℃, stir with 12;
(3) product that step (1) and (2) is obtained mixes, and stirs;
(4) be cooled to 25 ℃, filter the slurries that obtain, to remove residue;
(5) in the product that step (4) obtains, add 0.8 gram flow agent (Dutch Ai Fuka company; EFKA3883), 0.5 skimmer (Dutch Ai Fuka company; EFKA2022), 0.6 gram dispersion agent (U.S. Kerper company; Kerper-602) and 0.6 gram wetting agent (E.I.Du Pont Company 8857A) is mixed, and stirs.
(6) continue to add 5 gram solvent (ETHYLE ACETATE: n-butyl acetate: propyl carbinol weight ratio=1: 1: 0.5), stir, obtain coating A3.
Comparative Examples 1
This Comparative Examples is used to ultraviolet-curing paint of explaining prior art and preparation method thereof.
Prepare coating as follows:
(1) with 2.5 gram light trigger 1-hydroxy-cyclohexyl benzophenones (CIBA IRGACURE company, 184) and 10 gram solvent (ETHYLE ACETATE: n-butyl acetate: propyl carbinol weight ratio=1: 1: 0.5) mix, be stirred to abundant dissolving;
(2) with 45 grams, six functionality urethane acrylate (SARTOMER companies; CN9010), 15 gram Viscoat 295 (SARTOMER companies; SR350) and 8 gram difunctionality polyurethane acrylate resin (SARTOMER companies; CN983) with 32 gram solvent (ETHYLE ACETATE: n-butyl acetate: propyl carbinol weight ratio=1: 1: 0.4) mix, stir at 40 ℃;
(3) product that step (1) and (2) is obtained mixes, and stirs;
(4) be cooled to 25 ℃, filter the slurries that obtain, to remove residue;
(5) in the product that step (4) obtains, add 0.8 gram flow agent (Dutch Ai Fuka company; EFKA3883), 0.5 skimmer (Dutch Ai Fuka company; EFKA2022), 0.6 gram dispersion agent (U.S. Kerper company; Kerper-602) and 0.6 gram wetting agent (E.I.Du Pont Company 8857A) is mixed, and stirs.
(6) continue to add 5 gram solvent (ETHYLE ACETATE: n-butyl acetate: propyl carbinol weight ratio=1: 1: 0.5), stir, obtain coating C3.
Performance test
Coating A1-A3 for preparing in embodiment 1-3 and the Comparative Examples 1 and C1 are sprayed on respectively on the plastic plate (60 millimeters * 100 millimeters transparent PC DMX2415 plates); Baking is 5 minutes under 60 ℃ temperature; Pass through UV-light (energy be 1300 milli Jiao/square centimeters) then and shone 25 seconds, on plastic plate, obtain thickness and be 12 microns coating.Resulting coating is carried out following performance test, and the result is as shown in table 1.
1, test sticking power
On coatingsurface, draw 100 1 millimeter * 1 millimeter square lattice with drawing the lattice device.The model of using Minnesota Mining and Manufacturing Company to produce is 600 smooth being bonded on the grid of scotch tape, does not stay a space, uncovers adhesive tape rapidly with 60 degree angles then, and whether the cut edge of observing paint film has depainting.
As to have no depainting be 5B, and the depainting amount is 4B between 0-5 area %, and the depainting amount is 3B between 5-15 area %, and the depainting amount is 2B between 15-35 area %, and the depainting amount is 1B between 35-65 area %, and the depainting amount is 0B more than 65 area %.
2, hardness test
Carry out hardness test according to the method for stipulating in the chapter 4 among the GB/6739T.
Using Mitsubishi (UNI) hardness successively is the pencil of 2H, 3H, 4H, 5H and 6H, on sample, applies 1000 gram forces with 90 ° angles; 10 millimeters strokes; The pencil of each hardness is drawn 3 roads at different positions, and whether the observation sample outward appearance has obvious cut, and the minimum pencil hardness of cut appears in record.
3, resistance to marring test
Adopt BYK PH-5811/PH-5811 to join the PH-5813 gauge head: the gauge head diameter is 0.75 millimeter; Test angle is 90 °; Apply certain load (N) and streak at sample surfaces with the speed of 1 cel, whether the observation sample surface has cut, and the minimum load power (N) of cut appears in record.
Table 1
| Numbering | Sticking power | Hardness | Resistance to marring |
| A1 | 5B | 5H | 8N |
| A2 | 5B | 4H | 7N |
| A3 | 5B | 4H | 6N |
| B1 | 3B | 3H | 3N |
Can find out that from the data of table 1 coating that ultraviolet-curing paint provided by the invention forms is big to the sticking power of matrix, coating hardness is high, has well wear-resisting and scratch resistance performance.
Claims (7)
1. ultraviolet-curing paint; This coating contains high-functionality polyurethane vinyl resin, middle functionality acrylate monomer, light trigger and solvent; Functionality polyurethane acrylic resin and auxiliary agent is characterized in that this coating also contains epoxy acrylic resin and metal-salt acrylic ester oligomer in containing or not containing; Wherein, said high-functionality polyurethane vinyl resin molecule contains 6-12 carbon-carbon double bond; Functionality acrylate monomer molecule contains 2-3 carbon-carbon double bond in said; Functionality polyurethane acrylic resin molecule contains 2-4 carbon-carbon double bond in said; Gross weight with coating is a benchmark; The content of said high-functionality polyurethane vinyl resin is 20-60 weight %, and the content of said middle functionality acrylate monomer is 5-20 weight %, and the content of said light trigger is 0.5-5 weight %; The content of said epoxy acrylic resin is 5-30 weight %; The content of said metal-salt acrylic ester oligomer is 1-20 weight %, and the content of said solvent is 15-65 weight %, and the content of said middle functionality polyurethane acrylic resin is 0-15 weight %; The content of said auxiliary agent is 0-8 weight %, and said epoxy acrylic resin is the epoxy acrylic resin of difunctionality; Said metal-salt acrylic ester oligomer is one or more in zinc salt urethane acrylate oligomer, zinc salt polyester acrylate oligomer, zinc salt epoxy acrylate oligomer, sodium salt urethane acrylate oligomer, sodium salt polyester acrylate oligomer, the sodium salt epoxy acrylate oligomer, and the number-average molecular weight of said metal-salt acrylic ester oligomer is 1500-10000.
2. coating according to claim 1 wherein, is benchmark with the gross weight of coating; The content of said high-functionality polyurethane vinyl resin is 25-45 weight %; The content of functionality acrylate monomer is 8-15 weight % in said, and the content of said light trigger is 1-3 weight %, and the content of said epoxy acrylic resin is 5-20 weight %; The content of said metal-salt acrylic ester oligomer is 5-15 weight %; The content of said solvent is 25-40 weight %, and the content of said middle functionality polyurethane acrylic resin is 1-10 weight %, and the content of said auxiliary agent is 1-5 weight %.
3. coating according to claim 1 and 2, wherein, the weight ratio of said middle functionality polyurethane acrylic resin and said high-functionality polyurethane vinyl resin is 1: 0.5-10.
4. coating according to claim 1 and 2, wherein, said light trigger is a 1-hydroxy-cyclohexyl benzophenone, 2, one or more in 2-dimethyl--Alpha-hydroxy methyl phenyl ketone and (2,4, the 6-trimethylbenzoyl) diphenyl phosphine oxide.
5. coating according to claim 1 and 2, wherein, said auxiliary agent comprises one or more in flow agent, skimmer, dispersion agent and the wetting agent.
6. coating according to claim 1 and 2; Wherein, said solvent is selected from one or more in toluene, ETHYLE ACETATE, butylacetate, isobutyl acetate, propyl acetate, ethanol, propyl carbinol, pimelinketone, YLENE, hexone, acetone, methylethylketone, butyl glycol ether, the Ucar 35 butyl ether.
7. coating according to claim 6; Wherein, Said solvent is the mixture of ETHYLE ACETATE and/or n-butyl acetate and Virahol and/or propyl carbinol, and wherein, ETHYLE ACETATE and/or n-butyl acetate: the weight ratio of Virahol and/or propyl carbinol is 1: 0.05-1.
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| CN2008101353876A CN101638553B (en) | 2008-08-01 | 2008-08-01 | Ultraviolet curing coating |
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| CN101638553B true CN101638553B (en) | 2012-03-28 |
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| CN102485809B (en) * | 2010-12-06 | 2014-11-05 | 比亚迪股份有限公司 | UV-light curing coating |
| CN102140307B (en) * | 2011-05-11 | 2012-09-26 | 湖南松井新材料有限公司 | Ultraviolet-cured paint |
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