CN101967342B - Ultraviolet curing coating - Google Patents
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- CN101967342B CN101967342B CN2010105111144A CN201010511114A CN101967342B CN 101967342 B CN101967342 B CN 101967342B CN 2010105111144 A CN2010105111144 A CN 2010105111144A CN 201010511114 A CN201010511114 A CN 201010511114A CN 101967342 B CN101967342 B CN 101967342B
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Abstract
The invention discloses an ultraviolet curing coating. The ultraviolet curing coating is characterized by comprising basic resin, a diluting agent and a light initiator, wherein the basic resin comprises urethane acrylate resin and self-initiating polyester acrylate resin; and the light initiator comprises normal light initiator and low-yellowing light initiator. The coating provided by the invention has high curing activity; a paint film has the advantages of high hardness, high wear resistance, superior chemical resistance, low yellowing, high weather resistance and the like; and the coating is suitable for various plastic materials.
Description
Technical field
The present invention relates to a kind of chemistry painting industry; Particularly a kind of ultraviolet-curing paint that adopts the low-yellowing initiator; This ultraviolet-curing paint has higher initiating activity; Overcome disadvantages such as the smell that the migration of conventional initiator small molecules brings, xanthochromia, toxicity again, obtained the good paint film of over-all properties.
Background technology
The photo-cured coating technology is meant that light trigger or photosensitizers produce radical and initiating activity monomer, oligopolymer or resin polymerization reaction take place through ultraviolet light irradiation, obtain the process for treating surface of crosslinked fine and close paint film.It is a kind of green technology of high-solid level; Greatly reduce environmental pollution that organic volatile causes and to the infringement of HUMAN HEALTH; Have also simultaneously that curing speed is fast, good physical performance, pollution are little, save the energy and applicable to outstanding advantages such as wide variety of substrates, be described as green industrial new technology.Got into since 21 century, photocuring technology is developed rapidly, has become a new industry.
Light trigger (photoinitiator) is the photo-cured coating key ingredient, and it is related to formula system when photoirradiation, and can oligopolymer and reactive thinner be solid-state from liquid transformation rapidly, i.e. crosslinking curing.The basic role characteristics are: ((400nm～800nm) has certain extinction ability to initiator molecule for 250nm～420nm) or visible light between ultraviolet region; After direct or indirect extinction; Initiator molecule from ground state transition to active excited singlet; Can also continue between being, to scurry and jump, transit to excited triplet state, be referred to as excited state; After unit molecule or bimolecular effect, generation can trigger monomer polymeric biologically active fragment in its excited state, and these biologically active fragments can be radical, positively charged ion, negatively charged ion or ion radical.
Light trigger is of a great variety, and structure is different, and fragmentation pattern and performance difference are bigger.In fact whole, because intermolecular interaction can produce various structure fragment small molecules, the part fragment causes the oligopolymer polymerization film formation in the cracking process, and part becomes the inertia fragment, or residues in the paint film, or escapes to system.Light trigger contains benzene ring structure mostly, and mostly cleaved fragment is hazardous and noxious substances, and has certain colourity more or less.The escape fragment damages effect to human body and environment, has limited the use of photo-cured coating in the food sanitation field; Residual fragment has very big influence to the paint film xanthochromia, is the difficult problem that present photo-cured coating generally faces.
For overcoming above-mentioned shortcoming, chemist and coating workers have been carried out a large amount of work, mainly concentrate on following two aspects:
The one, the synthetic macromolecule initiator; Light-initiated group key is grafted on the main polymer chain; Reduce or eliminate the escape fragment, overcome residual and migration disadvantage, the approval that obtained FDA (Food and Drug Adminstration) in 2006 of using the small molecules light trigger to cause in the UV coating in the past; Use macromole evocating agent and the packages printing that can be used for food and medicine of coating and printing ink, for new space has been opened up in the application of photo-cured coating.
Macromole evocating agent can reduce cleaved fragment content; Reduce paint film xanthochromia, smell and human injury's effect that the migration of fragment small molecules is brought; But can not thoroughly eliminate; Main drawback is that relative its initiating activity of small molecules initiator is lower, and addition is relatively large, problems such as existence and other compound consistency difference of system.
The secondth, exploitation is from causing resin, reduces or do not re-use light trigger.Resin has light-initiated activity concurrently and photopolymerization is active from causing; Not only can eliminate the spinoff that the small molecules fragment brings; Can also effectively improve the film curing ability; Its application is the effective way of preparation low-yellowing photo-cured coating, also is expected to solidify and fields acquisition technological breakthroughs such as UV colored paint, UV printing ink in deep layer.But it is limited to cause the resin composite structure certainly, in prescription, uses simultaneously because its specific structure scope is not wide in range, and resin photolysis activity is low, and paint film property is also had certain negative impact, such as water-fast, chemical-resistant etc.
The xanthochromia index of ultraviolet-curing paint has not only embodied the decorative effect of coating, also reflects the prescription level and the quality of coating, like poisonous harmful substance contents, paint film weatherability or the like.Xanthochromic requirement is to test the front and back of xanthochromia value after rolling off the production line immediately to change to paint film in present application factory, rather than row test again after placement for some time, and much the ultraviolet-curing paint products are difficult to satisfy the xanthochromia requirement of application factory and are kept outside of the door.The photo-cured coating of the low-yellowing of exploitation excellent performance is the gordian technique that this project solves.
Summary of the invention
In order to overcome the deficiency of prior art, the present invention provides a kind of ultraviolet-curing paint that adopts the low-yellowing initiator, ultraviolet-curing paint reactive behavior, high gloss, high firmness, low-yellowing, advantage such as chemicals-resistant is good, sticking power is wide in range.
The technical solution adopted for the present invention to solve the technical problems is:
A kind of ultraviolet-curing paint; It is characterized in that: this coating contains matrix resin, thinner and light trigger; Wherein, used matrix resin comprises polyurethane acrylate resin and causes the polyester acrylate resin certainly that said light trigger comprises ordinary light initiator and low-yellowing initiator.
According to ultraviolet-curing paint provided by the invention, used viscosity is that 20000 ± 5000mpa.s/25 ℃ of polyurethane acrylate resin functionality is 4-6, and 3-5H on the hardness PC material plate can be paint film better hardness is provided; Causing polyester acrylate resin functionality is 3-6 certainly to use viscosity to be 30000 ± 5000mpa.s/25 ℃; F-H on the hardness PC material plate; Both can also have certain initiation function certainly simultaneously, can reduce the traditional photoinitiator consumption for paint film provides higher hardness; Reduce residual small molecules content, effectively reduce the coating xanthochromia.
According to ultraviolet-curing paint provided by the invention, under preferable case, based on the gross weight of said resin, the content of said polyurethane acrylic resin is 40-80 weight %, preferred 50-70 weight %; Said is 20-60 weight % from causing the polyester acrylate resin content, preferred 30-50 weight %.
According to ultraviolet-curing paint provided by the invention; Said polyurethane acrylate resin can be in various aliphatic urethane acrylate resin, cycloaliphatic polyurethane acrylate resin and the aromatic urethane acrylate resins that satisfy above-mentioned performance index scope one or more, aliphatic polyurethane acrylate resin.Said polyurethane acrylate resin can be commercially available, the 7605B of for example Japanese synthetic chemistry company; The CN9006 of Sartomer; The EB1290 of the special company of cyanogen; The B-618 of Guangzhou Boxing science and technology, the UV3600 of middle mountain Chiba Synesis Company; 3620 of field Electron Material Co., Ltd of middle mountain section.
According to ultraviolet-curing paint provided by the invention, said is the various polyester acrylate of the initiation certainly resins that satisfy the These parameters performance range from causing the polyester acrylate resin.Said causing the polyester acrylate resin can be purchased acquisition certainly, for example: Japanese synthetic SEC P-1; The B-12 of Guangzhou Boxing, B-13 and B-15; One or more resins of the UV-7516-100 of middle mountain Chiba are used with.
According to ultraviolet-curing paint provided by the invention, the content of described matrix resin, thinner and light trigger is the content in the conventional ultraviolet-curing paint.In general; Gross weight based on said coating; The content of said matrix resin is 40-80 weight %, be preferably 40-70 weight %, and the content of thinner is 10-50 weight %, be preferably 20-30 weight %, and the content of light trigger is 1-10 weight %, be preferably 2-8 weight %.
According to ultraviolet-curing paint provided by the invention; Said thinner is an organic solvent, and said organic solvent is one or more mixed solvents in toluene, ETHYLE ACETATE, N-BUTYL ACETATE, isobutyl acetate, ethanol, propyl carbinol, pimelinketone, YLENE, acetone, hexone, butyl glycol ether, the Ucar 35 butyl ether.
According to ultraviolet-curing paint provided by the invention, said ordinary light initiator is one or both of 2-hydroxyl-2 methyl-phenyl-acetone, 1-hydroxy cyclohexyl phenylketone.
Ultraviolet-curing paint provided by the invention has also used from synthetic low-yellowing initiator 4 simultaneously; 4 diacetyl pimelic acid diethyl esters, 4; 4 diacetyl NSC 52563s, 4; One or more mixtures of 4 diacetyl pimelic acid dibutylesters, such initiator has the efficiency of initiation height, good weatherability, the characteristics that the xanthochromia value is low.
Low-yellowing initiator provided by the invention mainly is to utilize Michael reaction synthetic, and used starting material have methyl aceto acetate, methyl acetoacetate, methyl ethyl diketone; One or more of methyl acrylate, ethyl propenoate, Bing Xisuandingzhi; Catalyst system therefor is: triethylamine, hexahydropyridine, sodium hydroxide, sodium ethylate, 1,1,3,3-4 methylguanidine (TMG), 1; 8-diazacyclo [5,4,0]-11 carbon-7-alkene (DBU), 1; 5-diazacyclo [4,3,0]-nine carbon-5-alkene (DBN) waits one or more to use with; 30-80 ℃ of reaction synthesis temperature.
It is one or more mixed solvents in toluene, ETHYLE ACETATE, N-BUTYL ACETATE, isobutyl acetate, ethanol, propyl carbinol, pimelinketone, YLENE, acetone, hexone, butyl glycol ether, the Ucar 35 butyl ether that ultraviolet-curing paint of the present invention adopts thinner.
Ultraviolet-curing paint of the present invention also contains reactive thinner; And based on said coating gross weight meter, the content of reactive thinner is 10-30%, adopts reactive thinner can improve the consistency between the various compositions in the coating of the present invention; Make this coating more even; Also can cooperate several kinds of resins in the coating can better cross-linking and curing reaction, in the solidified process, improve the degree of crosslinking of coating, make the formed paint film of coating of the present invention that good hardness and sticking power arranged.Wherein, Reactive thinner is 1, one or more in 6-pinakon propenoate, tripropylene glycol double methacrylate, Viscoat 295, pentaerythritol triacrylate, Dipentaerythritol five propenoate, the dipentaerythritol acrylate.
Ultraviolet-curing paint of the present invention also contains auxiliary agent, and the total mass meter of coating based, and auxiliary agent content is 0.3-6%.
Auxiliary agent is one or more of flow agent, coupling agent and tensio-active agent, and the coating based total amount, and flow agent content is 0.1-2 weight %, preferred 0.5-1.5 weight %; The content of coupling agent is 0.1-2 weight %, preferred 0.5-1.5 weight %; The content of tensio-active agent is 0.1-2 weight %, preferred 0.5-1.5 weight %
.
The flow agent that the present invention adopts can be selected EFKA 3883, EFKA 3886 and the EFKA 3600 of the Dutch Ai Fuka company that is purchased for use, the BYK 366 of BYK company, BYK 333, BYK 307 and BYK 306, the DEGO 410 of German Di Gao company.
The coupling agent that the present invention adopts can be for well known to a person skilled in the art various coupling agents, for example can select the KH-550,6020,6040 and 7104 and the DP7192 of rising sun Xiao Subsidiary Company of the Dow Corning Corporation that is purchased for use.
The tensio-active agent that the present invention adopts can for example can be selected 8857A and ZonylFSO-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 various tensio-active agents.
The preparation method of ultraviolet-curing paint of the present invention can mix said matrix resin, thinner and light trigger simultaneously, also can mix by proceed step by step.Under preferable case, earlier with light trigger and part mixing diluents, light trigger is fully dissolved, obtain a kind of solution that contains light trigger; Then that matrix resin, reactive thinner and another part mixing diluents is even, obtain a kind of slurries that contain matrix resin, reactive thinner, above-mentioned slurries and initiator solution are mixed; In the auxiliary agents such as flow agent, coupling agent and tensio-active agent one or more are dissolved into an amount of thinner, and agitation condition adds above-mentioned mixed system down, stirs, and will remain the thinner adding.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.
The preferred method for preparing ultraviolet-curing paint of the present invention is:
(1) with light trigger and part mixing diluents, is stirred to abundant dissolving, obtains containing the solution of light trigger;
(2) matrix resin, reactive thinner and another part mixing diluents is even, obtain containing the slurries of matrix resin, slurries are added in the initiator solution, mix;
(3) in the auxiliary agents such as flow agent, coupling agent and tensio-active agent one or more are dissolved into an amount of thinner, agitation condition adds above-mentioned mixed system down, stirs, and will remain the thinner adding;
(4) filter with 400 order silks, packing finally obtains preferred product provided by the invention.
The invention has the beneficial effects as follows: coating provided by the invention is suitable for the finish paint of plastic basis material, like mobile phone, digital camera, MP3 shell etc.With paint spay-coating of the present invention behind plastic basis material, normal temperature levelling 3-5min, 55-60 ℃ the baking 5min, at 600-800mj/cm
2Energy solidifies 15-20S down, and obtaining thickness is the paint film of 12-20 μ m.Paint solidification provided by the invention is active high, and advantages such as paint film has high firmness, high abrasion, chemicals-resistant is excellent, xanthochromia is low, good weatherability are adapted at using on the multiple plastics material.
Below in conjunction with embodiment the present invention is further specified.
Embodiment
Embodiment 1 (synthesizing of low-yellowing initiator):
In the 5000ml four-hole boiling flask that has prolong, TM, gas tube, mechanical stirrer, feed dry air, agitator; Add the 2661.6g Bing Xisuandingzhi after 10 minutes, with 20.0g N-BUTYL ACETATE dissolving 0.7g p methoxy phenol (MQ), 1.4g 2; 6-ditertbutylparacresol (BHT) adds reaction kettle with above-mentioned solution under the agitation condition, takes by weighing 35.6g DBU; Dropwise add reaction kettle under the agitation condition, slowly be warming up to 45 ℃; Take by weighing the 1000.0g methyl ethyl diketone, dropwise in the 150-180min time range with constant pressure funnel, with 30gB solvent wash funnel, 45-55 ℃ of insulation 4h, discharging obtains reddish yellow liquid; Aforesaid liquid is placed 0 ℃ of environment 24h, take out, grind to form powdery.Obtain low-yellowing initiator 4,4 diacetyl pimelic acid dibutylesters provided by the invention.
Embodiment 2 (synthesizing of low-yellowing initiator):
In the 5000ml four-hole boiling flask that has prolong, TM, gas tube, mechanical stirrer, feed dry air, agitator; Add the 2592.6g Bing Xisuandingzhi after 10 minutes, with 20.0g N-BUTYL ACETATE dissolving 0.7g p methoxy phenol (MQ), 1.4g 2; 6-ditertbutylparacresol (BHT) adds reaction kettle with above-mentioned solution under the agitation condition, takes by weighing 30.2g DBN; Dropwise add reaction kettle under the agitation condition, slowly be warming up to 45 ℃; Take by weighing the 1100.0g methyl aceto acetate, dropwise in the 150-180min time range with constant pressure funnel, with 30gB solvent wash funnel, 45 ℃ of insulation 4h, discharging obtains reddish yellow liquid; Aforesaid liquid is placed 0 ℃ of environment 24h, take out, grind to form powdery.Obtain low-yellowing initiator 4,4 diacetyl pimelic acid diethyl esters provided by the invention.
Embodiment 3 (synthesizing of low-yellowing initiator):
In the 5000ml four-hole boiling flask that has prolong, TM, gas tube, mechanical stirrer, feed dry air, agitator; Add the 2676.6g methyl acrylate after 10 minutes, with 20.0g N-BUTYL ACETATE dissolving 0.7g p methoxy phenol (MQ), 1.4g 2; 6-ditertbutylparacresol (BHT) adds reaction kettle with above-mentioned solution under the agitation condition, takes by weighing 35.6g DBU; Dropwise add reaction kettle under the agitation condition, slowly be warming up to 45 ℃; Take by weighing the 1200.0g methyl ethyl diketone, dropwise in the 150-180min time range with constant pressure funnel, with 30gB solvent wash funnel, 45 ℃ of insulation 4h, discharging obtains reddish yellow liquid; Aforesaid liquid is placed 0 ℃ of environment 24h, take out, grind to form powdery.Obtain low-yellowing initiator 4,4 diacetyl NSC 52563s provided by the invention.
Embodiment 4 (preparation of low-yellowing photo-cured coating):
0.3g light trigger (I-184), 3.0 g, 4,4 diacetyl pimelic acid dibutylesters are dissolved into 5.0g thinner (toluene: N-BUTYL ACETATE=1: 1) mix, be stirred to abundant dissolving, obtain containing the solution of light trigger; With the B-12 of the 7605B six functionality polyurethane acrylate resins of 53.0g Japan synthetic chemistry company, 22.0g Guangzhou Boxing from cause resin, 8.0g reactive thinner DPHA adds the solution that contains light trigger successively, mix; With the flow agent (BYK 333) of 0.5g, 0.3g coupling agent (DOW CORNING Z-6040) and 0.2g tensio-active agent (Zonyl 8857A) are dissolved into the 2.0g thinner and are mixed with mixing solutions, and agitation condition adds above-mentioned system down and mixes; Add the 5.7g mixing diluents and evenly filter with 400 order silks the back, obtain low-yellowing ultraviolet-curing paint provided by the invention.
Embodiment 5 (preparation of low-yellowing photo-cured coating):
0.3g light trigger (I-184), 5.0 g, 4,4 diacetyl pimelic acid dibutylesters are dissolved into 5.0g thinner (toluene: N-BUTYL ACETATE=1: 1) mix, be stirred to abundant dissolving, obtain containing the solution of light trigger; 7605B six functionality polyurethane acrylate resins, 10.0g reactive thinner DPHA, the 5.3g reactive thinner TMPTA of 66.0g Japan synthetic chemistry company are added the solution that contains light trigger successively, mix; Flow agent (BYK 333) and 0.2g tensio-active agent (Zonyl 8857A) with 0.5g are dissolved into the 2.0g thinner and are mixed with mixing solutions, and agitation condition adds above-mentioned system down and mixes; Add the 5.7g mixing diluents and evenly filter with 400 order silks the back, obtain low-yellowing ultraviolet-curing paint provided by the invention.
Comparison example 1 (preparation of low-yellowing photo-cured coating):
0.3g light trigger (I-184), 3.0 g, 4,4 diacetyl NSC 52563s are dissolved into 5.0g thinner (toluene: N-BUTYL ACETATE=1: 1) mix, be stirred to abundant dissolving, obtain containing the solution of light trigger; With the UV-7516-100 of mountain Chiba among the EB1290 six functionality polyurethane acrylate resins of the special company of 53.0g cyanogen, the 22.0g from cause resin, 8.0g reactive thinner DPHA adds the solution that contains light trigger successively, mix; With the flow agent (BYK 333) of 0.5g, 0.3g coupling agent (DOW CORNING Z-6040) and 0.2g tensio-active agent (Zonyl 8857A) are dissolved into the 2.0g thinner and are mixed with mixing solutions, and agitation condition adds above-mentioned system down and mixes; Add the 5.7g mixing diluents and evenly filter with 400 order silks the back, obtain low-yellowing ultraviolet-curing paint provided by the invention.
Comparison example 2 (preparation of low-yellowing photo-cured coating):
0.3g light trigger (I-184), 5.0 g, 4,4 diacetyl NSC 52563s are dissolved into 5.0g thinner (toluene: N-BUTYL ACETATE=1: 1) mix, be stirred to abundant dissolving, obtain containing the solution of light trigger; CN9006 six functionality polyurethane acrylate resins, 10.0g reactive thinner DPHA, the 5.3g reactive thinner TMPTA of 66.0g Sartomer are added the solution that contains light trigger successively, mix; Flow agent (BYK 333) and 0.2g tensio-active agent (Zonyl 8857A) with 0.5g are dissolved into the 2.0g thinner and are mixed with mixing solutions, and agitation condition adds above-mentioned system down and mixes; Add the 5.7g mixing diluents and evenly filter with 400 order silks the back, obtain low-yellowing ultraviolet-curing paint provided by the invention.
[performance test]
The coating for preparing among embodiment 4-5 and the contrast experiment 1-2 is adjusted viscosity to 9s (NK-2 with thinner; 25 ℃), be sprayed on the 600mm*100mm black plastic PC colour table levelling three minutes then respectively; Baking is 5 minutes under 60 ℃ temperature, then at 680mj/cm
2The process UV-irradiation is 10 seconds under the ability condition, obtains the paint film that thickness is 12 μ m at plastic casing.Resulting paint film is carried out following performance test, and the result is as shown in table 2.
Can know through above-mentioned experiment, traditional relatively photo-cured coating (back test △ b=1.5-3.0 rolls off the production line), coating yellow variate provided by the invention is low; Back test △ b < 0.5 rolls off the production line; Simultaneously, The performance test results shows, uses low-yellowing initiator effect to be superior to from causing resin.
Claims (6)
1. ultraviolet-curing paint; It is characterized in that: this coating contains matrix resin, thinner, light trigger and reactive thinner; Wherein, Used matrix resin comprises polyurethane acrylate resin and causes the polyester acrylate resin certainly that said light trigger comprises ordinary light initiator and low-yellowing initiator; Said low-yellowing initiator be with in methyl aceto acetate, methyl acetoacetate, methyl ethyl diketone, methyl acrylate, ethyl propenoate, the Bing Xisuandingzhi one or more under the catalyst action through one or more mixtures in Michael reaction synthetic 4,4 diacetyl pimelic acid diethyl esters, 4,4 diacetyl NSC 52563s, 4, the 4 diacetyl pimelic acid dibutylesters; Said catalyzer is triethylamine, hexahydropyridine, sodium hydroxide, sodium ethylate, 1,1,3; 3-4 methylguanidine, 1,8-diazacyclo [5,4; 0]-and 11 carbon-7-alkene, 1,5-diazacyclo [4; 3,0]-in nine carbon-5-alkene one or more, wherein; Used polyurethane acrylate resin functionality is 4-6, and viscosity is 20000 ± 5000mPa.s/25 ℃, 3-5H on the hardness PC material plate; Said is 3-6 from causing polyester acrylate resin functionality, and viscosity is 30000 ± 5000mPa.s/25 ℃, F-H on the hardness PC material plate; Coating based gross weight meter wherein, said matrix resin content is 40-80%, and amount of diluent is 10-50%, and photoinitiator levels is 1-10%; Based on said coating gross weight meter; The content of reactive thinner is 10-30%; Wherein reactive thinner is 1, one or more in 6-pinakon propenoate, tripropylene glycol double methacrylate, Viscoat 295, pentaerythritol triacrylate, Dipentaerythritol five propenoate, the dipentaerythritol acrylate.
2. a kind of ultraviolet-curing paint according to claim 1 is characterized in that: based on matrix resin gross weight meter, said polyurethane acrylate resin content is 40-80%, and said is 20-60% from causing the polyester acrylate resin content.
3. a kind of ultraviolet-curing paint according to claim 1 is characterized in that: said thinner is one or more mixed solvents in toluene, ETHYLE ACETATE, N-BUTYL ACETATE, isobutyl acetate, ethanol, propyl carbinol, pimelinketone, YLENE, acetone, hexone, butyl glycol ether, the Ucar 35 butyl ether.
4. a kind of ultraviolet-curing paint according to claim 1 is characterized in that: the ordinary light initiator is 2-hydroxyl-2 methyl-phenyl-acetone and/or 1-hydroxy cyclohexyl phenylketone.
5. a kind of ultraviolet-curing paint according to claim 1 is characterized in that: also contain auxiliary agent, and the total mass meter of coating based, said auxiliary agent content is 0.3-6%.
6. a kind of ultraviolet-curing paint according to claim 5; It is characterized in that: said auxiliary agent is one or more of flow agent, coupling agent and tensio-active agent; And coating based gross weight meter; Said flow agent content is 0.1-2 weight %, and the content of coupling agent is 0.1-2 weight %, and the content of tensio-active agent is 0.1-2 weight %
.
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| CN2010105111144A CN101967342B (en) | 2010-10-19 | 2010-10-19 | Ultraviolet curing coating |
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| CN2010105111144A CN101967342B (en) | 2010-10-19 | 2010-10-19 | Ultraviolet curing coating |
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| CN101967342B true CN101967342B (en) | 2012-08-22 |
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| CN116102970B (en) * | 2022-12-16 | 2023-12-05 | 山东高速集团有限公司 | Ultraviolet light cured bi-component road marking paint |
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| CA1338677C (en) * | 1989-09-29 | 1996-10-22 | Yoshihiro Nishiyama | Thermosetting covering sheet and a method of forming hard coating on the surface of substrates using the same |
| CN101845244B (en) * | 2010-04-14 | 2012-03-14 | 东莞大宝化工制品有限公司 | UV wiping paint |
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