CN106281176B - A kind of windshield renovation agent and preparation method thereof - Google Patents
A kind of windshield renovation agent and preparation method thereof Download PDFInfo
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- CN106281176B CN106281176B CN201610605283.1A CN201610605283A CN106281176B CN 106281176 B CN106281176 B CN 106281176B CN 201610605283 A CN201610605283 A CN 201610605283A CN 106281176 B CN106281176 B CN 106281176B
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/10—Epoxy resins modified by unsaturated compounds
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
- C08G59/1461—Unsaturated monoacids
- C08G59/1466—Acrylic or methacrylic acids
Abstract
It is an object of the invention to there are problems that hidden trace is poor, intensity can not be kept for a long time existing glass renovation agent, a kind of windshield renovation agent and preparation method thereof is provided, glass renovation agent technical field is belonged to.The renovation agent is renovation agent mother liquor and reactive diluent tri (propylene glycol) diacrylate, methyl methacrylate, product obtained after silane coupling agent and the reaction of photoinitiator 2- hydroxy-2-methyl -1- phenyl -1- acetone；Renovation agent mother liquor is epoxy resin and tri (propylene glycol) diacrylate, ethyl acrylate, acrylic acid, hydroquinone, the product that generates after pentaerythritol triacrylate and the reaction of 2- hydroxy-2-methyl -1- phenyl -1- acetone.The product refractive index is similar to windshield, and the multiple angles of windshield after reparation can't see slight crack, it is fast to repair speed, and the intensity of repair place renovation agent can remain unchanged, and the use intensity of windshield is consistent with the windshield before breakage.
Description
Technical field
The invention belongs to glass renovation agent technical field, in particular to a kind of windshield renovation agent and preparation method thereof.
Background technique
China's car ownership is increased with swift and violent speed, and quantity has been more than 100,000,000.Through investigating, automobile wind
The breakage rate for keeping off glass is 10% or so, if the windshield after breakage is all replaced, it will cause very big renewal costs
Waste, and it is unfavorable for environmental protection；If effectively repair to damaged windshield and not only having saved fund cost, but also section is accomplished
About resource and environmental protection also reduce the replacement frequency of automobile wind shield glass, create huge social benefit.
Presently preferred recovery technique is to be carried out the crack of damaged windshield using the renovation agent of high molecular material
Bonding, but the hidden trace of existing renovation agent is poor, the windshield after reparation still is able to see crackle, repairing effect and intensity
It is unable to reach requirement；In addition, existing renovation agent can only carry out the minimally invasive reparation of small area to windshield, limitation is very big；And
And there is also the renovation agent intensity of repair place is lower and lower, the case where causing repair place to be cracked again.
Summary of the invention
It is an object of the invention to for existing glass renovation agent, there are hidden traces that poor, intensity can not keep for a long time asks
Topic provides a kind of windshield renovation agent and preparation method thereof.The product refractive index is similar to windshield, the wind after reparation
Gear glass can't see slight crack from multiple angles, it is fast repair speed, and the intensity of repair place renovation agent can remain unchanged, windscreen
The use intensity of glass is consistent with the windshield before breakage.
A kind of windshield renovation agent is renovation agent mother liquor and reactive diluent tri (propylene glycol) diacrylate
(TPGDA), methyl methacrylate (MMA), silane coupling agent and photoinitiator 2- hydroxy-2-methyl -1- phenyl -1- acetone
It (HMPF) is product obtained after 28~32: 30~35: 32~37: 1.0~1.5: 1.5~2.0 reactions according to volume ratio；
Epoxy resin and TPGDA of the renovation agent mother liquor for epoxide number 0.3-0.45, ethyl acrylate, acrylic acid,
Hydroquinone, pentaerythritol triacrylate (PETA) and HMPF according to volume ratio be 30~35: 20~25: 16~20: 7.0~
The product obtained after 7.5: 0.1~0.2: 14~20: 2~4 reactions；
Silane coupling agent is gamma-aminopropyl-triethoxy-silane (KH550) or γ-(methacryloxypropyl) propyl trimethoxy
Base silane (KH570).
A kind of preparation method of windshield renovation agent, includes the following steps:
(1) under agitation, the epoxy resin that epoxide number is 0.3-0.45 is added in reaction vessel, it is heated to 85~
95 DEG C, add reactive diluent TPGDA and ethyl acrylate；Then solution temperature is risen to 105~115 DEG C, is condensed
Reaction 30~60 minutes；
The volume ratio of the epoxy resin and TPGDA and ethyl acrylate are 30~35: 20~25: 16~20；
Preferably, the epoxy resin is one of E-31, E-35, E-42, E-44 or a variety of mixtures；
(2) keeping solution temperature is 105~115 DEG C, and the mixed of acrylic acid and hydroquinone is added dropwise in 30~40 minutes
Solution is closed, is further continued for being stirred to react 20~30 minutes；
The volume ratio of epoxy resin and acrylic acid, hydroquinone is 30~35: 7.0~7.5: 0.1~0.2；
(3) it is separately added into PETA and photoinitiator HMPF into solution, stirs 20~30 minutes；Then solution is cooled to
Room temperature to get arrive renovation agent mother liquor；
The volume ratio of the epoxy resin and PETA and HMPF are 30~35: 14~20: 2~4；
(4) it is separately added into TPGDA, MMA, silane coupling agent and photoinitiator HMPF into renovation agent mother liquor, stirs evenly
Place 200~240 hours afterwards to get renovation agent is arrived；
The silane coupling agent is KH550 or KH570；
The volume ratio of the mother liquor and TPGDA, MMA, silane coupling agent and HMPF are 28~32: 30~35: 32~37:
1.0~1.5: 1.5~2.0.
The purposes of windshield renovation agent of the invention is, the application in terms of repairing damaged automobile wind shield glass.
Through detecting, the character parameter of renovation agent made from the above method are as follows:
1, curing time: just less than 10 seconds, the time was fully cured less than 15 minutes (in ultraviolet wavelength 365 in the time admittedly
It is measured under conditions of~400nm)；
2, character before solidifying: appearance: colorless and transparent or light yellow clear liquid；Viscosity: at 25 DEG C, 50~300CPS；
3, character after solidifying: appearance: it is fully transparent, it is placed under hot and humid environment and still keeps within 12 months transparent, it is not white
Change, non yellowing；Temperature resistant range after solidification: -40~130 DEG C；Peel strength: greater than 12MPa；Refractive index: 1.52~1.56；Light transmission
Rate 98.4~99.2%.
Compared with prior art, present invention has an advantage that
1, the renovation agent refractive index is similar to windshield, and the windshield after reparation be can't see from multiple angles to be split
Trace, repairs that speed is fast, and the intensity of repair place renovation agent can remain unchanged, the use intensity of windshield with it is damaged before
Windshield is consistent.
2, this method is easy to operate, and reaction condition is mild.
Detailed description of the invention
The windshield figure that the renovation agent that Fig. 1 is prepared by embodiment 1 is repaired；
Wherein, before (a) is repaired, after (b) repairing.
The windshield figure that the renovation agent that Fig. 2 is prepared by embodiment 2 is repaired；
Wherein, before (c) repairing, after (d) repairing.
The windshield figure that the renovation agent that Fig. 3 is prepared by embodiment 3 is repaired；
Wherein, before (e) repairing, after (f) repairing.
The windshield figure that the renovation agent that Fig. 4 is prepared by embodiment 4 is repaired；
Wherein, before (g) repairing, after (h) repairing.
Specific embodiment
Raw material in embodiment is commercially available.
The restorative procedure of glass are as follows: 1, damaged glass cleaning is clean, then pasted in the side of glass position to be repaired
Upper PET light film；2, renovation agent is injected from the other side of position to be repaired, liquid is allowed slowly to penetrate into breakage, until seeping completely；3,
Low smooth UV ultraviolet lamp pipe irradiation breakage is taken, fluorescent tube is 2-3 centimetres at a distance from glass, is irradiated 3-5 minutes；4, PET is torn
Light film simultaneously gets rid of the extra renovation agent adhered on glass, repairs and completes.
Embodiment 1
(1) under agitation, 15L epoxy resin E-44 is added in reaction vessel, is heated to 90 DEG C, adds
12.5L reactive diluent tri (propylene glycol) diacrylate (TPGDA) and 9L ethyl acrylate；Then solution temperature is risen to
It 110 DEG C, carries out condensation reaction 45 minutes；
(2) keeping solution temperature is 110 DEG C, be added dropwise in 25~30 minutes 3.65L acrylic acid and 0.05L to benzene two
The mixed solution of phenol, the reaction was continued 20 minutes；
(3) 8L pentaerythritol triacrylate (PETA) and 1.5L photoinitiator 2- hydroxyl -2- are separately added into solution
Methyl-1-phenyl-1- acetone (HMPF) stirs 20 minutes；Then solution is cooled to room temperature to get renovation agent mother liquor is arrived；
(4) take 15L renovation agent mother liquor, be separately added into the TPGDA of 16.5L, the MMA of 17L, 0.6L coupling agent KH550 and
0.9L photoinitiator HMPF places 240 hours after mixing evenly to get renovation agent is arrived.
Through detecting, the character parameter of renovation agent made from the above method are as follows:
1, curing time: just consolidate the time 7 seconds, be fully cured the time 10.6 minutes (in 365~400nm of ultraviolet wavelength
Under conditions of measure)；
2, character before solidifying: appearance: colorless and transparent or light yellow clear liquid；Viscosity: at 25 DEG C, 216.2CPS；
3, character after solidifying: appearance: it is fully transparent, it is placed under hot and humid environment and still keeps within 12 months transparent, it is not white
Change, non yellowing；Temperature resistant range after solidification: -40~130 DEG C；Peel strength: 13.7MPa；Refractive index: 1.54；Light transmittance
99.2%.
The renovation agent is taken to repair damaged windshield, the picture that windshield repairs front and back is as shown in Figure 1, it can be seen that repairs
The breakage of windshield after multiple can't see, and due in preprosthetic frit without dirt so that the wind after repairing
It keeps off glass and can't see slight crack from multiple angles；After repairing 12 months, repair place is unchanged, still keeps transparent, and crack is not opened
It splits；Also, the use intensity of windshield is consistent with the windshield before breakage.
Embodiment 2
(1) under agitation, 3.5L epoxy resin E-31 is added in reaction vessel, is heated to 85~86 DEG C, then plus
Enter 2.2L reactive diluent TPGDA and 2L ethyl acrylate；Then solution temperature is risen to 105~106 DEG C, carries out condensation reaction
60 minutes；
(2) keeping solution temperature is 105~106 DEG C, and 0.75L acrylic acid and 0.015L are added dropwise in 40 minutes to benzene two
The mixed solution of phenol, the reaction was continued 25 minutes；
(3) it is separately added into the HMPF of the PETA and 0.4L of 2L into solution, stirs 25 minutes；Then solution is cooled to room
Temperature to get arrive renovation agent mother liquor；
(4) take 2.8L renovation agent mother liquor, be separately added into the TPGDA of 3L, the coupling agent KH570 of the MMA of 3.2L, 0.1L and
The HMPF of 1.5L places 200 hours after mixing evenly to get renovation agent is arrived.
Through detecting, the character parameter of renovation agent made from the above method are as follows:
1, curing time: just consolidate the time 8 seconds, be fully cured the time 14.2 minutes (in 365~400nm of ultraviolet wavelength
Under conditions of measure)；
2, character before solidifying: appearance: colorless and transparent or light yellow clear liquid；Viscosity: at 25 DEG C, 97.7CPS；
3, character after solidifying: appearance: it is fully transparent, it is placed under hot and humid environment and still keeps within 12 months transparent, it is not white
Change, non yellowing；Temperature resistant range after solidification: -40~130 DEG C；Peel strength: 12.2MPa；Refractive index: 1.52；Light transmittance
98.4%.
The renovation agent is taken to repair damaged windshield, the picture that windshield repairs front and back is as shown in Figure 2, it can be seen that repairs
The breakage of multiple wind shield glass wind shield can't see, and due in preprosthetic frit without dirt so that the windscreen after repairing
Glass can't see slight crack from multiple angles；After repairing 12 months, repair place is unchanged, still keeps transparent, and crack is not cracked；
Also, the use intensity of windshield is consistent with the windshield before breakage.
Embodiment 3
(1) under agitation, 3.3L epoxy resin E-35 is added in reaction vessel, is heated to 93~95 DEG C, then plus
Enter 2L reactive diluent TPGDA and 1.6L ethyl acrylate；Then solution temperature is risen to 113~115 DEG C, carries out condensation reaction
30 minutes；
(2) keeping solution temperature is 113~115 DEG C, and 0.7L acrylic acid and 0.02L hydroquinone are added dropwise in 35 minutes
Mixed solution, the reaction was continued 30 minutes；
(3) it is separately added into 1.4L PETA and 0.2L photoinitiator HMPF into solution, stirs 30 minutes；Then by solution
It is cooled to room temperature to get renovation agent mother liquor is arrived；
(4) the renovation agent mother liquor for taking 3.2L is separately added into the TPGDA of 3.5L, the MMA of 3.7L, 0.15L coupling agent KH550
With 0.2L photoinitiator HMPF, 220 hours are placed after mixing evenly to get renovation agent is arrived.
Through detecting, the character parameter of renovation agent made from the above method are as follows:
1, curing time: just consolidate the time 9 seconds, be fully cured the time 13.5 minutes (in 365~400nm of ultraviolet wavelength
Under conditions of measure)；
2, character before solidifying: appearance: colorless and transparent or light yellow clear liquid；Viscosity: at 25 DEG C, 116.1CPS；
3, character after solidifying: appearance: it is fully transparent, it is placed under hot and humid environment and still keeps within 12 months transparent, it is not white
Change, non yellowing；Temperature resistant range after solidification: -40~130 DEG C；Peel strength: 12.9MPa；Refractive index: 1.56；Light transmittance
98.9%.
The renovation agent is taken to repair damaged windshield, windshield repairs the picture of front and back as shown in figure 3, repairing rear windshield
The breakage of glass can't see, and due in preprosthetic frit without dirt so that windshield after repairing is from more
A angle can't see slight crack；After repairing 12 months, repair place is unchanged, still keeps transparent, and crack is not cracked；Also, wind
The use intensity for keeping off glass is consistent with the windshield before breakage.
Embodiment 4
(1) under agitation, reaction vessel is added in the epoxy resin E-44 of the epoxy resin E-42 and 1.1L of 2.0L
In, 91~92 DEG C are heated to, 2.3L reactive diluent TPGDA and 1.7L ethyl acrylate is added；Then by solution temperature liter
To 111~112 DEG C, carry out condensation reaction 50 minutes；
(2) keeping solution temperature is 111~112 DEG C, and 0.74L acrylic acid and 0.018L are added dropwise in 30 minutes to benzene two
The mixed solution of phenol, the reaction was continued 27 minutes；
(3) it is separately added into 1.7L PETA and 0.35L photoinitiator HMPF into solution, stirs 28 minutes；Then by solution
It is cooled to room temperature to get renovation agent mother liquor is arrived；
(4) the renovation agent mother liquor for taking 3.1L is separately added into the TPGDA of 3.2L, the MMA of 3.3L, 0.11L coupling agent KH550
With 0.16L photoinitiator HMPF, 210 hours are placed after mixing evenly to get renovation agent is arrived.
Through detecting, the character parameter of renovation agent made from the above method are as follows:
1, curing time: just consolidate the time 7 seconds, be fully cured the time 14.0 minutes (in 365~400nm of ultraviolet wavelength
Under conditions of measure)；
2, character before solidifying: appearance: colorless and transparent or light yellow clear liquid；Viscosity: at 25 DEG C, 286.9CPS；
3, character after solidifying: appearance: it is fully transparent, it is placed under hot and humid environment and still keeps within 12 months transparent, it is not white
Change, non yellowing；Temperature resistant range after solidification: -40~130 DEG C；Peel strength: 13.5MPa；Refractive index: 1.55；Light transmittance
98.8%.
The renovation agent is taken to repair damaged windshield, windshield repairs the picture of front and back as shown in figure 4, repairing rear windshield
The breakage of glass can't see, and due in preprosthetic frit without dirt so that windshield after repairing is from more
A angle can't see slight crack；After repairing 12 months, repair place is unchanged, still keeps transparent, and crack is not cracked；Also, wind
The use intensity for keeping off glass is consistent with the windshield before breakage.
Claims (5)
1. a kind of windshield renovation agent, which is characterized in that for renovation agent mother liquor and reactive diluent tripropylene glycol dipropyl
Olefin(e) acid ester, methyl methacrylate, silane coupling agent and photoinitiator 2- hydroxy-2-methyl -1- phenyl -1- acetone are according to volume
Than product obtained after being reacted for 28~32:30~35:32~37:1.0~1.5:1.5~2.0；
The renovation agent mother liquor is the epoxy resin and tri (propylene glycol) diacrylate of epoxide number 0.3-0.45, acrylic acid
Ethyl ester, acrylic acid, hydroquinone, pentaerythritol triacrylate and 2- hydroxy-2-methyl -1- phenyl -1- acetone are according to volume
Than the product generated after being reacted for 30~35:20~25:16~20:7.0~7.5:0.1~0.2:14~20:2~4；
The silane coupling agent is gamma-aminopropyl-triethoxy-silane or γ-(methacryloxypropyl) propyl trimethoxy silicon
Alkane.
2. a kind of windshield renovation agent according to claim 1, which is characterized in that viscosity before it solidifies are as follows: 25 DEG C, 50
~300CPS；Curing time: just less than 10 seconds, the time was fully cured less than 15 minutes in the time admittedly；Peel strength after solidification: greater than
12MPa；Refractive index: 1.52~1.56；Light transmittance: 98.4~99.2%.
3. a kind of preparation method of windshield renovation agent of any of claims 1 or 2, which comprises the steps of:
(1) under agitation, the epoxy resin that epoxide number is 0.3-0.45 is added in reaction vessel, is heated to 85~95
DEG C, add reactive diluent tri (propylene glycol) diacrylate and ethyl acrylate；Then solution temperature is risen to 105~
It 115 DEG C, carries out condensation reaction 30~60 minutes；
(2) keeping solution temperature is 105~115 DEG C, and the mixing that acrylic acid and hydroquinone are added dropwise in 30~40 minutes is molten
Liquid is further continued for being stirred to react 20~30 minutes；
(3) pentaerythritol triacrylate and photoinitiator 2- hydroxy-2-methyl -1- phenyl -1- third are separately added into solution
Ketone stirs 20~30 minutes；Then solution is cooled to room temperature to get renovation agent mother liquor is arrived；
(4) tri (propylene glycol) diacrylate, methyl methacrylate, silane coupling agent are separately added into renovation agent mother liquor
With photoinitiator 2- hydroxy-2-methyl -1- phenyl -1- acetone, 200~240 hours are placed after mixing evenly to get reparation is arrived
Agent；
The silane coupling agent is gamma-aminopropyl-triethoxy-silane or γ-(methacryloxypropyl) propyl trimethoxy silicon
Alkane.
4. a kind of preparation method of windshield renovation agent according to claim 3, which is characterized in that the epoxy resin
For one of E-31, E-35, E-42, E-44 or a variety of mixtures.
5. the purposes of windshield renovation agent of any of claims 1 or 2, which is characterized in that the windshield renovation agent is being repaired
Application in terms of multiple damaged automobile wind shield glass.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201610605283.1A CN106281176B (en) | 2016-07-28 | 2016-07-28 | A kind of windshield renovation agent and preparation method thereof |
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| CN201610605283.1A CN106281176B (en) | 2016-07-28 | 2016-07-28 | A kind of windshield renovation agent and preparation method thereof |
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| CN106281176B true CN106281176B (en) | 2019-04-19 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201715588D0 (en) * | 2017-09-26 | 2017-11-08 | Belron Int Ltd | Curing repair resin |
| CN111139012A (en) * | 2018-11-06 | 2020-05-12 | 深圳市志纵四海科技有限公司 | Adhesive and preparation method thereof |
| MX2022000481A (en) * | 2019-07-12 | 2022-04-18 | Mondofix Inc | Thiol-based adhesive formulations for repairing windshields. |
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|---|---|---|---|---|
| CN101864265A (en) * | 2010-05-18 | 2010-10-20 | 上海鼎道科技发展有限公司 | Photocured adhesive for repairing micro cracks of automotive glass and preparation method thereof |
| CN104212396A (en) * | 2014-09-10 | 2014-12-17 | 湖南柯盛新材料有限公司 | Photo-curable resin composition for repairing facing marble plank and preparation and using method of photo-curable resin composition |
| CN104449517A (en) * | 2014-12-22 | 2015-03-25 | 国家电网公司 | Ultraviolet cured repair adhesive and preparation method thereof |
-
2016
- 2016-07-28 CN CN201610605283.1A patent/CN106281176B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101864265A (en) * | 2010-05-18 | 2010-10-20 | 上海鼎道科技发展有限公司 | Photocured adhesive for repairing micro cracks of automotive glass and preparation method thereof |
| CN104212396A (en) * | 2014-09-10 | 2014-12-17 | 湖南柯盛新材料有限公司 | Photo-curable resin composition for repairing facing marble plank and preparation and using method of photo-curable resin composition |
| CN104449517A (en) * | 2014-12-22 | 2015-03-25 | 国家电网公司 | Ultraviolet cured repair adhesive and preparation method thereof |
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