CN114874742A - Ultraviolet curing adhesive with low volume shrinkage and preparation method thereof - Google Patents
Ultraviolet curing adhesive with low volume shrinkage and preparation method thereof Download PDFInfo
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- CN114874742A CN114874742A CN202210549965.0A CN202210549965A CN114874742A CN 114874742 A CN114874742 A CN 114874742A CN 202210549965 A CN202210549965 A CN 202210549965A CN 114874742 A CN114874742 A CN 114874742A
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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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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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
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Abstract
The invention discloses an ultraviolet curing adhesive with low volume shrinkage and a preparation method thereof, belonging to the technical field of preparation of photocuring materials. The invention solves the technical problems of large volume shrinkage and serious product deformation of the existing base type ultraviolet curing resin system. The ultraviolet curing adhesive comprises the following components in parts by weight: 15-60 parts of polyurethane acrylate resin, 10-65 parts of epoxy acrylate resin, 5-40 parts of diluent, 0.3-7 parts of photoinitiator and 0.2-5 parts of other auxiliary agents. The invention adopts polyurethane acrylate and epoxy acrylate resin to form a composite oligomer, so that a mixed system can generate two reactions of free radical polymerization and cationic polymerization, and has synergistic effect in the aspects of volume shrinkage change complementation, performance regulation and the like, so that the ultraviolet curing adhesive with low volume shrinkage has stable material size before and after curing, high curing speed and good mechanical property.
Description
Technical Field
The invention belongs to the technical field of preparation of photocuring materials, and particularly relates to an ultraviolet curing adhesive with low volume shrinkage and a preparation method thereof.
Background
Uv curable adhesives are a functional material commonly found in life and are generally considered as protective films on substrate surfaces to prevent corrosion and chemical damage in harsh environments. The ultraviolet light curing adhesive is divided into a free radical type and a cationic type according to the curing reaction, more than 95 percent of the prior ultraviolet light curing adhesive is an acrylate free radical type, and the ultraviolet light curing adhesive is characterized in that the volume shrinkage rate is generally larger in the curing process. The volume shrinkage that occurs during the curing of UV adhesives is due to the variation in the tightness of the arrangement between atoms during curing. The main reason is that in the curing process, acrylate monomer molecules which are originally acted by van der Waals force become covalent bond linkage, the distance between corresponding atoms is shortened greatly, and then entropy change, namely free volume change, is generated in the process from the monomer to the polymer, the liquid monomer molecules are in a loose free moving state before photocuring, the free volume is large, the acrylate monomer generates a three-dimensional network crosslinked polymer after photocuring, the number of intermolecular crosslinking points is large, the movement of chain segments is obviously limited, the free volume is reduced, and volume shrinkage is brought. Because the adhesive relates to a bonding interface when in use, the defects of stress and volume generated by shrinkage in the curing process are difficult to eliminate, the size precision of bonding is influenced, and the bonding force is directly reduced. The adhesion of rigid materials is easy to generate striated gaps and even cracks, and the easy generation of warping deformation of flexible materials severely limits the application field of the light curing technology. Therefore, it is necessary to provide an ultraviolet curing adhesive with low volume shrinkage and a preparation method thereof.
Disclosure of Invention
The invention provides an ultraviolet curing adhesive with low volume shrinkage and a preparation method thereof, aiming at solving the technical problems of large volume shrinkage and serious product deformation of the existing free radical type ultraviolet curing resin system.
The technical scheme of the invention is as follows:
the ultraviolet curing adhesive with low volume shrinkage consists of the following raw materials in parts by weight: 15-60 parts of polyurethane acrylate resin, 10-65 parts of epoxy acrylate resin, 5-40 parts of diluent, 0.3-7 parts of photoinitiator and 0.2-5 parts of other additives, wherein the mass ratio of the polyurethane acrylate resin to the epoxy acrylate resin is (1-2): 1.
further, the urethane acrylate is one or more of aromatic urethane acrylate, aliphatic urethane diacrylate, fluorine-modified urethane acrylate, and benzene-free solvent-based modified urethane acrylate, which are mixed at an arbitrary ratio.
The epoxy acrylate resin is further limited to be one or more of 2-hydroxy-3-phenoxypropyl acrylate, epoxy acrylate, bisphenol A epoxy acrylate, novolac epoxy acrylate and fatty acid modified epoxy acrylate which are mixed in any proportion.
Further defined, the diluent is an acrylate monomer.
Further, the acrylate monomer is one or more of monofunctional acrylate, bifunctional acrylate and multifunctional acrylate monomer, and is mixed in any proportion.
More specifically, the monofunctional acrylate is one or more of isodecyl acrylate, cyclohexyl methacrylate, benzyl acrylate, 2-phenoxyethyl acrylate, and isobornyl acrylate, which are mixed in an arbitrary ratio.
More specifically, the bifunctional acrylate is one or more of 1, 6-hexanediol diacrylate, ethylene glycol dimethacrylate A, and tricyclodecane dimethanol dimethacrylate mixed at an arbitrary ratio.
More specifically, the multifunctional acrylate monomer is pentaerythritol triacrylate and/or dipentaerythritol hexaacrylate.
Further defined, photoinitiators include free radical initiators and cationic initiators.
More specifically, the radical initiator is one or more selected from the group consisting of 2-hydroxy-2-methyl-1-phenyl acetone, 1-hydroxycyclohexyl benzophenone, 2-methyl-1- (4-methylmercaptophenyl) -2-morpholine-1-one, ethyl 2,4, 6-trimethylbenzoylphosphonate, 2-hydroxy-4- (2-hydroxyethoxy) -2-methylpropiophenone, methyl benzoylformate, phenyl bis (2,4, 6-trimethylbenzoyl) phosphine oxide, benzophenone, and 4-methylbenzophenone, and these are mixed in an arbitrary ratio.
More specifically, the cationic initiator is one or more selected from diphenyl- (4-phenylsulfide) phenyl hexachlorophosphate, thiophenylphenyl, triarylsulfonium salt, and dialkylphenacylsulfonium salt, and is mixed in any ratio.
Further defined, the other additives include leveling agents and dispersing agents.
Further limiting, the viscosity of the ultraviolet curing adhesive with low volume shrinkage is 11500-12500 @25 ℃ mPa & s.
The invention also provides a preparation method of the ultraviolet curing adhesive with low volume shrinkage, which comprises the following specific preparation processes: adding the raw materials into a double-planetary power mixing kettle according to the weight ratio, firstly stirring and dispersing for 0.5-1 h at the stirring speed of 300r/min, then stirring and dispersing for 2-3 h at the stirring speed of 900r/min, and finally carrying out centrifugal defoaming on the uniformly mixed system to obtain the ultraviolet curing adhesive.
The invention provides an ultraviolet curing adhesive with low volume shrinkage and a preparation method thereof, wherein polyurethane acrylate and epoxy acrylate are mixed in a composite mode, and a high-performance light curing adhesive with the volume shrinkage of 0.5% is obtained by optimizing a formula, and compared with the prior art, the ultraviolet curing adhesive has the following beneficial effects:
(1) the invention adopts polyurethane acrylate and epoxy acrylate resin to form a composite oligomer, and the mixing proportion of the two substances is regulated to enable a mixed system to generate two reactions of free radical polymerization and cationic polymerization, thereby fully playing the advantages of the two substances, playing a synergistic effect in the aspects of volume shrinkage change complementation, performance regulation and the like, and enabling the ultraviolet curing adhesive with low volume shrinkage to have stable material size before and after curing, high curing speed and good mechanical property.
(2) The ultraviolet curing adhesive provided by the invention can reduce or even eliminate volume shrinkage in the curing process, can improve the bonding strength of the ultraviolet curing adhesive and a base material, and has wider adaptability.
(3) When the viscosity of the liquid adhesive is ideal (the viscosity is 11500-12500 @25 ℃ mPa & s), the low-viscosity acrylate oligomer is selected, and the dosage of a diluent monomer is reduced, so that the content of double bonds in a photocuring resin system is reduced, and the volume shrinkage rate is further reduced.
(4) The invention selects the acrylate monomer with low content of functional groups and branched chain or cyclic structure as the diluent, which is caused by the substituent-CH on the double bond atom 2 R in-CH-R increases steric hindrance between bonding atoms after double bond polymerization to form a longer covalent bond, so that the volume shrinkage rate is reduced, and the reduction of the volume shrinkage rate is facilitated by matching with two mixed resins for compounding.
(5) The ultraviolet curing adhesive with low volume shrinkage provided by the invention has the advantages of simple preparation process, short flow, low equipment dependence, continuous production and suitability for industrial large-scale production.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The experimental procedures used in the following examples are conventional unless otherwise specified. The materials, reagents, methods and apparatus used, unless otherwise specified, are conventional in the art and are commercially available to those skilled in the art.
The following examples relate to the manufacturer and model of the raw materials:
the aliphatic polyurethane diacrylate is a Changxing product and has the molecular weight of 1000-2000 Mw; the epoxy acrylate is an Disemann product, and the molecular weight is 500-800 Mw; the diluent is dipentaerythritol hexaacrylate (DPHA), Ethylene Glycol Dimethacrylate (EGDMA), isobornyl acrylate (IBOA) and isodecyl acrylate (ISODA) from Sanwang company; the initiator is 2,4, 6-trimethyl benzoyl phosphonic acid ethyl ester (TPO-L) of Nanjing Wali company, 1-hydroxycyclohexyl benzophenone (184) and diphenyl- (4-phenyl sulfur) phenyl hexachloro phosphate (GC-2391) of a new broad-spectrum transmission material; the leveling agent is BYK307 of Germany BYK; the dispersant is 670 from digao.
Example 1:
the ultraviolet curing adhesive with low volume shrinkage of the embodiment comprises the following raw materials in percentage by weight: 60 parts of matrix resin, wherein the matrix resin contains 65% of aliphatic polyurethane diacrylate and 35% of epoxy acrylate; 36 parts of a diluent, wherein the diluent contains 60% of dipentaerythritol hexaacrylate and 40% of ethylene glycol dimethacrylate; 3.5 parts of a photoinitiator, wherein the photoinitiator contains 40% of ethyl 2,4, 6-trimethylbenzoylphosphonate, 50% of 1-hydroxycyclohexyl benzophenone and 10% of diphenyl- (4-phenylthio) phenyl hexachlorophosphate; and other auxiliary agents, wherein the auxiliary agents comprise 0.2 part of flatting agent and 0.3 part of dispersing agent.
The method for preparing the ultraviolet curing adhesive with low volume shrinkage rate described in example 1 comprises the following steps:
adding matrix resin, a diluent, a photoinitiator and other auxiliaries into a double-planet power mixing kettle according to a weight ratio, stirring and dispersing for 1 hour at a stirring speed of 300r/min, then stirring and dispersing for 2.5 hours at a stirring speed of 900r/min, and finally carrying out centrifugal deaeration on a uniformly mixed system to obtain the ultraviolet curing adhesive.
Example 2:
the ultraviolet curing adhesive with low volume shrinkage of the embodiment comprises the following raw materials in percentage by weight: 70 parts of matrix resin, wherein the matrix resin contains 65% of aliphatic polyurethane diacrylate and 35% of epoxy acrylate; 26 parts of a diluent, wherein the diluent contains 60% of isobornyl acrylate and 40% of isodecyl acrylate; 3.5 parts of a photoinitiator, wherein the photoinitiator contains 40% of ethyl 2,4, 6-trimethylbenzoylphosphonate, 50% of 1-hydroxycyclohexyl benzophenone and 10% of diphenyl- (4-phenylthio) phenyl hexachlorophosphate; and other auxiliary agents, wherein the auxiliary agents comprise 0.2 part of flatting agent and 0.3 part of dispersing agent.
The method for preparing the ultraviolet curing adhesive with low volume shrinkage rate described in example 2 comprises the following steps:
adding matrix resin, a diluent, a photoinitiator and other auxiliaries into a double-planetary power mixing kettle according to a weight ratio, firstly stirring and dispersing for 1h at a stirring speed of 300r/min, then stirring and dispersing for 2.5h at a stirring speed of 900r/min, and finally carrying out centrifugal defoaming on the uniformly mixed system to obtain the ultraviolet curing adhesive.
Example 3:
the ultraviolet curing adhesive with low volume shrinkage of the embodiment comprises the following raw materials in percentage by weight: 70 parts of matrix resin, wherein the matrix resin contains 55% of aliphatic polyurethane diacrylate and 45% of epoxy acrylate; 26 parts of a diluent, wherein the diluent contains 60% of isobornyl acrylate and 40% of isodecyl acrylate; 3.5 parts of a photoinitiator, wherein the photoinitiator contains 40% of ethyl 2,4, 6-trimethylbenzoylphosphonate, 50% of 1-hydroxycyclohexyl benzophenone and 10% of diphenyl- (4-phenylthio) phenyl hexachlorophosphate; and other auxiliary agents, wherein the auxiliary agents comprise 0.2 part of flatting agent and 0.3 part of dispersing agent.
The method for preparing the ultraviolet curing adhesive with low volume shrinkage rate described in example 3 comprises the following steps:
adding matrix resin, a diluent, a photoinitiator and other auxiliaries into a double-planetary power mixing kettle according to a weight ratio, firstly stirring and dispersing for 1h at a stirring speed of 300r/min, then stirring and dispersing for 2.5h at a stirring speed of 900r/min, and finally carrying out centrifugal defoaming on the uniformly mixed system to obtain the ultraviolet curing adhesive.
Example 4:
the ultraviolet curing adhesive with low volume shrinkage of the embodiment comprises the following raw materials in percentage by weight: 70 parts of matrix resin, wherein the matrix resin contains 45% of aliphatic polyurethane diacrylate and 55% of epoxy acrylate; 26 parts of a diluent, wherein the diluent contains 60% of isobornyl acrylate and 40% of isodecyl acrylate; 3.5 parts of a photoinitiator, wherein the photoinitiator contains 40% of ethyl 2,4, 6-trimethylbenzoylphosphonate, 50% of 1-hydroxycyclohexyl benzophenone and 10% of diphenyl- (4-phenylthio) phenyl hexachlorophosphate; and other auxiliary agents, wherein the auxiliary agents comprise 0.2 part of flatting agent and 0.3 part of dispersing agent.
The method for preparing the ultraviolet curing adhesive with low volume shrinkage rate described in example 4 comprises the following steps:
adding matrix resin, a diluent, a photoinitiator and other auxiliaries into a double-planetary power mixing kettle according to a weight ratio, firstly stirring and dispersing for 1h at a stirring speed of 300r/min, then stirring and dispersing for 2.5h at a stirring speed of 900r/min, and finally carrying out centrifugal defoaming on the uniformly mixed system to obtain the ultraviolet curing adhesive.
Example 5:
the ultraviolet curing adhesive with low volume shrinkage of the embodiment comprises the following raw materials in percentage by weight: 70 parts of matrix resin, wherein all the matrix resin is aliphatic polyurethane diacrylate; 26 parts of a diluent, wherein the diluent contains 60% of isobornyl acrylate and 40% of isodecyl acrylate; 3.5 parts of a photoinitiator, wherein the photoinitiator contains 40% of ethyl 2,4, 6-trimethylbenzoylphosphonate, 50% of 1-hydroxycyclohexyl benzophenone and 10% of diphenyl- (4-phenylthio) phenyl hexachlorophosphate; and other auxiliary agents, wherein the auxiliary agents comprise 0.2 part of flatting agent and 0.3 part of dispersing agent.
The method for preparing the ultraviolet curing adhesive with low volume shrinkage rate described in example 5 comprises the following steps:
adding matrix resin, a diluent, a photoinitiator and other auxiliaries into a double-planetary power mixing kettle according to a weight ratio, firstly stirring and dispersing for 1h at a stirring speed of 300r/min, then stirring and dispersing for 2.5h at a stirring speed of 900r/min, and finally carrying out centrifugal defoaming on the uniformly mixed system to obtain the ultraviolet curing adhesive.
Example 6:
the ultraviolet curing adhesive with low volume shrinkage of the embodiment comprises the following raw materials in percentage by weight: 70 parts of matrix resin, wherein all the matrix resin is epoxy acrylate; 26 parts of a diluent, wherein the diluent contains 60% of isobornyl acrylate and 40% of isodecyl acrylate; 3.5 parts of a photoinitiator, wherein the photoinitiator contains 40% of ethyl 2,4, 6-trimethylbenzoylphosphonate, 50% of 1-hydroxycyclohexyl benzophenone and 10% of diphenyl- (4-phenylthio) phenyl hexachlorophosphate; and other assistants, including leveling agent 0.2 weight portions and dispersant 0.3 weight portions.
The method for preparing the uv curable adhesive with low volume shrinkage described in example 6 is as follows:
adding matrix resin, a diluent, a photoinitiator and other auxiliaries into a double-planetary power mixing kettle according to a weight ratio, firstly stirring and dispersing for 1h at a stirring speed of 300r/min, then stirring and dispersing for 2.5h at a stirring speed of 900r/min, and finally carrying out centrifugal defoaming on the uniformly mixed system to obtain the ultraviolet curing adhesive.
The volume shrinkage of the uv curable adhesives prepared in examples 1 to 6 was measured according to the specification of international standard ISO3521, the density of the resin before and after curing was measured, and the shrinkage was calculated from the density, and the shrinkage (ρ ═ ρ [ (]) was calculated Rear end -ρ Front side ) X 100% after/[ rho ], where [ rho ] Rear end And ρ Front side Density after curing and before curing, respectively. The density before and after curing can be measured by a pycnometer method and water as a reference. The curing conditions of the adhesive are as follows: LED cold light source with light intensity of 2000mW/cm 2 And the illumination time is 1.6 s.
The volume shrinkage of the uv curable adhesives prepared in examples 1 to 5 was measured according to the specification of international standard ISO3521, the density of the resin before and after curing was measured, and the shrinkage was calculated from the density, and the shrinkage (ρ ═ ρ [ (]) was calculated Rear end -ρ Front side ) X 100% after/[ rho ], where [ rho ] Rear end And ρ Front side Density after curing and before curing, respectively. The density before and after curing can be measured by a pycnometer method and water as a reference. The curing conditions of the adhesive are as follows: LED cold light source with light intensity of 2000mW/cm 2 And the illumination time is 1.6 s.
The results are shown in table 1 below:
TABLE 1
| Test specimen | Volume shrinkage rate |
| Example 1 | 8.5 |
| Example 2 | 5.0 |
| Example 3 | 1.0 |
| Example 4 | 3.0 |
| Example 5 | 13 |
| Example 6 | 0.3 |
From the above results, it can be seen that when polyester acrylate and epoxy acrylate are mixed to a proper ratio and a diluent having a branched or cyclic structure with a low functional group content is added, the volume shrinkage during curing can be effectively eliminated, and the composition is suitable for various coatings requiring low dimensional change.
The above embodiments are merely preferred embodiments of the present invention, and the present invention is not limited to the above embodiments, and modifications and changes thereof may be made by those skilled in the art within the scope of the claims of the present invention.
Claims (10)
1. The ultraviolet curing adhesive with low volume shrinkage is characterized by comprising the following raw materials in parts by weight: 15-60 parts of polyurethane acrylate resin, 10-65 parts of epoxy acrylate resin, 5-40 parts of diluent, 0.3-7 parts of photoinitiator and 0.2-5 parts of other additives, wherein the mass ratio of the polyurethane acrylate resin to the epoxy acrylate resin is (1-2): 1.
2. the ultraviolet curing adhesive with low volume shrinkage of claim 1, wherein the urethane acrylate is one or more of aromatic urethane acrylate, aliphatic urethane diacrylate, fluorine-modified urethane acrylate and benzene-free solvent-based modified urethane acrylate, and is mixed in any proportion.
3. The ultraviolet curing adhesive with low volume shrinkage of claim 1, wherein the epoxy acrylate resin is one or more of 2-hydroxy-3-phenoxypropyl acrylate, epoxy acrylate, bisphenol a epoxy acrylate, novolac epoxy acrylate, and fatty acid modified epoxy acrylate, and is mixed in any proportion.
4. The UV-curable adhesive with low volume shrinkage according to claim 1, wherein the diluent is an acrylate monomer, and the acrylate monomer is one or more of monofunctional acrylate, difunctional acrylate and multifunctional acrylate, and is mixed in any proportion.
5. The UV-curable adhesive with low volume shrinkage according to claim 4, wherein the monofunctional acrylate is one or more of isodecyl acrylate, cyclohexyl methacrylate, benzyl acrylate, 2-phenoxyethyl acrylate and isobornyl acrylic acid, and is mixed in any proportion.
6. The UV-curable adhesive with low volume shrinkage according to claim 4, wherein the difunctional acrylate is one or more of 1, 6-hexanediol diacrylate, ethylene glycol dimethacrylate (A), and tricyclodecane dimethanol dimethacrylate (DMD), which are mixed in any proportion.
7. The UV-curable adhesive with low volume shrinkage according to claim 4, wherein the multifunctional acrylate monomer is pentaerythritol triacrylate and/or dipentaerythritol hexaacrylate.
8. The UV-curable adhesive with low volume shrinkage according to claim 1, wherein the photoinitiator comprises a free radical initiator and a cationic initiator.
9. The UV-curable adhesive with low volume shrinkage according to claim 8, wherein the free radical initiator is one or more of 2-hydroxy-2-methyl-1-phenyl acetone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- (4-methylmercaptophenyl) -2-morpholine-1-one, ethyl 2,4, 6-trimethylbenzoylphosphonate, 2-hydroxy-4- (2-hydroxyethoxy) -2-methyl propiophenone, methyl benzoylformate, phenyl bis (2,4, 6-trimethylbenzoyl) phosphine oxide, benzophenone, and 4-methylbenzophenone, and is mixed in any ratio; the cationic initiator is one or more of diphenyl- (4-phenylthio) phenyl hexachlorophosphate, thiophenyl phenyl, triaryl sulfonium salt and dialkyl benzene acyl methyl sulfonium salt which are mixed in any proportion.
10. The preparation method of the ultraviolet curing adhesive with low volume shrinkage rate according to claim 1 is characterized by comprising the following steps: adding the raw materials into a double-planetary power mixing kettle according to the weight ratio, firstly stirring and dispersing for 0.5-1 h at the stirring speed of 300r/min, then stirring and dispersing for 2-3 h at the stirring speed of 900r/min, and finally carrying out centrifugal defoaming on the uniformly mixed system to obtain the ultraviolet curing adhesive.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115491131A (en) * | 2022-10-26 | 2022-12-20 | 西安思摩威新材料有限公司 | Ultraviolet curing organic glue for OLED packaging and use method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104004489A (en) * | 2014-04-14 | 2014-08-27 | 江苏嘉娜泰有机硅有限公司 | Preparation of anti-yellowing liquid optical adhesive |
| CN106634789A (en) * | 2016-11-09 | 2017-05-10 | 东莞市贝特利新材料有限公司 | Ultraviolet light cured type adhesive and preparation method thereof |
| CN110172327A (en) * | 2019-05-31 | 2019-08-27 | 黄敏 | Photocuring composite adhesive and its production technology |
| CN111057515A (en) * | 2019-11-20 | 2020-04-24 | 中国船舶重工集团公司第七0七研究所 | Block-type-structure UV adhesive for sensing coil and preparation method thereof |
-
2022
- 2022-05-20 CN CN202210549965.0A patent/CN114874742A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104004489A (en) * | 2014-04-14 | 2014-08-27 | 江苏嘉娜泰有机硅有限公司 | Preparation of anti-yellowing liquid optical adhesive |
| CN106634789A (en) * | 2016-11-09 | 2017-05-10 | 东莞市贝特利新材料有限公司 | Ultraviolet light cured type adhesive and preparation method thereof |
| CN110172327A (en) * | 2019-05-31 | 2019-08-27 | 黄敏 | Photocuring composite adhesive and its production technology |
| CN111057515A (en) * | 2019-11-20 | 2020-04-24 | 中国船舶重工集团公司第七0七研究所 | Block-type-structure UV adhesive for sensing coil and preparation method thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115491131A (en) * | 2022-10-26 | 2022-12-20 | 西安思摩威新材料有限公司 | Ultraviolet curing organic glue for OLED packaging and use method thereof |
| CN115491131B (en) * | 2022-10-26 | 2023-11-28 | 西安思摩威新材料有限公司 | Ultraviolet light curing organic glue for OLED packaging and application method thereof |
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