CN112500823A - High-weather-resistance UV thermosetting adhesive and preparation method thereof - Google Patents
High-weather-resistance UV thermosetting adhesive and preparation method thereof Download PDFInfo
- Publication number
- CN112500823A CN112500823A CN202011410633.1A CN202011410633A CN112500823A CN 112500823 A CN112500823 A CN 112500823A CN 202011410633 A CN202011410633 A CN 202011410633A CN 112500823 A CN112500823 A CN 112500823A
- Authority
- CN
- China
- Prior art keywords
- parts
- component
- thermosetting adhesive
- cationic
- thermal initiator
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 27
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 27
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title description 4
- 239000003999 initiator Substances 0.000 claims abstract description 18
- 125000002091 cationic group Chemical group 0.000 claims abstract description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000007822 coupling agent Substances 0.000 claims abstract description 13
- 239000012949 free radical photoinitiator Substances 0.000 claims abstract description 13
- 239000000178 monomer Substances 0.000 claims abstract description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000945 filler Substances 0.000 claims abstract description 10
- 229910021485 fumed silica Inorganic materials 0.000 claims abstract description 10
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003822 epoxy resin Substances 0.000 claims abstract description 8
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000012952 cationic photoinitiator Substances 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical group C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 6
- -1 iron arene salts Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 claims description 4
- JRWNODXPDGNUPO-UHFFFAOYSA-N oxolane;prop-2-enoic acid Chemical compound C1CCOC1.OC(=O)C=C JRWNODXPDGNUPO-UHFFFAOYSA-N 0.000 claims description 4
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 3
- OLPZCIDHOZATMA-UHFFFAOYSA-N 2,2-dioxooxathiiran-3-one Chemical class O=C1OS1(=O)=O OLPZCIDHOZATMA-UHFFFAOYSA-N 0.000 claims description 3
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 244000028419 Styrax benzoin Species 0.000 claims description 3
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 3
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 claims description 3
- 229960002130 benzoin Drugs 0.000 claims description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 3
- 125000005520 diaryliodonium group Chemical group 0.000 claims description 3
- 239000012954 diazonium Substances 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- NWWQVENFTIRUMF-UHFFFAOYSA-N diphenylphosphanyl 2,4,6-trimethylbenzoate Chemical compound CC1=CC(C)=CC(C)=C1C(=O)OP(C=1C=CC=CC=1)C1=CC=CC=C1 NWWQVENFTIRUMF-UHFFFAOYSA-N 0.000 claims description 3
- 238000007599 discharging Methods 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 235000019382 gum benzoic Nutrition 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 238000007789 sealing Methods 0.000 claims description 3
- 125000005409 triarylsulfonium group Chemical group 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000009477 glass transition Effects 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 2
- 150000001768 cations Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 3
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- 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
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a high-weather-resistance UV thermosetting adhesive which is prepared from the following raw materials in parts by weight: 1-5 parts of component A, 1-5 parts of component B, 1-5 parts of acrylic monomer, 0.001-1 part of free radical photoinitiator, 0.001-1 part of cationic thermal initiator, 0.05-5 parts of coupling agent, 0.05-5 parts of fumed silica and 0.05-5 parts of filler, wherein the component A is epoxy acrylate with a structure shown in formula 1, and the molecular weight of the epoxy acrylate is 200-500000; the component B is alicyclic epoxy resin containing a structure shown in a formula 2. The UV thermosetting adhesive can realize low-temperature fast curing based on a cationic system, and has the advantages of higher glass transition temperature, high hardness, excellent weather resistance and good substrate bonding force.
Description
Technical Field
The invention relates to the technical field of thermosetting adhesives, in particular to a high-weather-resistance UV thermosetting adhesive and a preparation method thereof.
Background
Most of the existing UV thermosetting adhesives in the market are thiol systems or thiol-cation systems, and due to the introduction of thiol, a lot of flexible thioether bonds are generated in the systems, so that the adhesive is low in Tg, soft in hardness and poor in weather resistance; in the process of heating and curing, mercaptan has a certain inhibiting effect on cations to generate alkyl sulfonate, and the alkyl sulfonate is a good accelerator for curing epoxy resin, but the effect can be exerted only at the temperature of more than 100 ℃, so that low-temperature rapid curing cannot be realized, and the application range of the epoxy resin is limited. How to solve the above technical problems is the direction in which those skilled in the art are working on development.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a high-weather-resistance UV thermosetting adhesive which can realize low-temperature rapid curing.
In order to achieve the purpose, the invention adopts the technical scheme that: the high-weather-resistance UV thermosetting adhesive is prepared from the following raw materials in parts by mass: 1-5 parts of component A, 1-5 parts of component B, 1-5 parts of acrylic monomer, 0.001-1 part of free radical photoinitiator, 0.001-1 part of cationic thermal initiator, 0.05-5 parts of coupling agent, 0.05-5 parts of fumed silica and 0.05-5 parts of filler, wherein the component A is epoxy acrylate with a structure shown in formula 1, and the molecular weight of the epoxy acrylate is 200-500000; the component B is alicyclic epoxy resin containing a structure shown in a formula 2,
formula 1:
formula 2:
as a specific embodiment, the acrylic monomer is selected from one or a mixture of isobornyl acrylate, tricyclodecane dimethanol diacrylate and tetrahydrofuran acrylate.
As a specific embodiment, the free radical photoinitiator is selected from the group consisting of a mixture of one or more of benzoin diethyl ether, 1-hydroxycyclohexyl phenyl ketone, diphenyl- (2,4, 6-trimethylbenzoyl) oxyphosphorus, 2-isopropylthioxanthone, and phenyl bis (2,4, 6-trimethylbenzoyl) phosphine oxide.
As a specific embodiment, the cationic photoinitiator is selected from one or more of diazonium salts, diaryliodonium salts, triarylsulfonium salts, alkylsulfonium salts, iron arene salts, sulfonyloxy ketones, and triarylsiloxy ethers.
In a specific embodiment, the cationic thermal initiator is a phosphate-based cationic thermal initiator.
As a specific embodiment, Y-glycidoxypropyltrimethoxysilane is used as the coupling agent.
Another object of the present invention is to provide a method for preparing the high weather resistance UV thermosetting adhesive, comprising the following steps:
1) adding the component A, the component B, an acrylic monomer and a free radical photoinitiator into a reaction kettle under a yellow light, and stirring until the free radical photoinitiator is completely dissolved;
2) under a yellow light, adding the coupling agent, the fumed silica and the filler into a reaction kettle, and stirring until the coupling agent, the fumed silica and the filler are completely and uniformly mixed;
3) grinding the fully mixed materials by a three-roller grinder under a yellow light until the particle size is less than 15 um;
4) adding a cationic photoinitiator and a cationic thermal initiator under a yellow light, and stirring at room temperature until the cationic photoinitiator and the cationic thermal initiator are completely and uniformly mixed;
5) discharging under a yellow light, filling, vacuum defoaming, sealing and storing in dark place.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages: the raw materials of the high-weatherability UV thermosetting adhesive adopt alicyclic epoxy resin to improve the curing rate and realize low-temperature rapid curing, and the system adopts a mercaptan-removed cationic system to realize high glass transition temperature and excellent weatherability.
Detailed Description
The technical solution of the present invention is further illustrated below with reference to specific examples.
The high-weather-resistance UV thermosetting adhesive is prepared from the following raw materials in parts by mass: 1-5 parts of component A, 1-5 parts of component B, 1-5 parts of acrylic monomer, 0.001-1 part of free radical photoinitiator, 0.001-1 part of cationic thermal initiator, 0.05-5 parts of coupling agent, 0.05-5 parts of fumed silica and 0.05-5 parts of filler, wherein the component A is epoxy acrylate with a structure shown in formula 1, and the molecular weight of the epoxy acrylate is 200-500000; the component B is alicyclic epoxy resin containing a structure shown in a formula 2,
formula 1:
formula 2:
wherein the acrylic monomer is selected from one or a mixture of more of isobornyl acrylate, tricyclodecane dimethanol diacrylate and tetrahydrofuran acrylate; the free radical photoinitiator is selected from one or more of benzoin diethyl ether, 1-hydroxycyclohexyl phenyl ketone, diphenyl- (2,4, 6-trimethyl benzoyl) oxyphosphorus, 2-isopropyl thioxanthone and phenyl bis (2,4, 6-trimethyl benzoyl) phosphine oxide; the cationic photoinitiator is one or more of diazonium salt, diaryl iodonium salt, triaryl sulfonium salt, alkyl sulfonium salt, iron arene salt, sulfonyloxy ketone and triaryl siloxy ether; the cationic thermal initiator adopts phosphate cationic thermal initiator; the coupling agent adopts Y-glycidoxypropyltrimethoxysilane.
Example one
The specific raw material components of the high-weather-resistance UV thermosetting adhesive are shown in the table 1.
TABLE 1
The preparation method of the high-weather-resistance UV thermosetting adhesive comprises the following steps:
1) adding the component A, the component B, an acrylic monomer and a free radical photoinitiator into a reaction kettle under a yellow light, and stirring until the free radical photoinitiator is completely dissolved;
2) under a yellow light, adding the coupling agent, the fumed silica and the filler into a reaction kettle, and stirring until the coupling agent, the fumed silica and the filler are completely and uniformly mixed;
3) grinding the fully mixed materials by a three-roller grinder under a yellow light until the particle size is less than 15 um;
4) adding a cationic photoinitiator and a cationic thermal initiator under a yellow light, and stirring at room temperature until the cationic photoinitiator and the cationic thermal initiator are completely and uniformly mixed;
5) discharging under a yellow light, filling, vacuum defoaming, sealing and storing in dark place.
The performance of the prepared high-weather-resistance UV thermosetting adhesive is tested, and the test method comprises the following steps:
1. glass transition temperature: reference standard ISO 11357-2;
2. curing depth: injecting glue into a polytetrafluoroethylene cylinder with the diameter of 10mm and the height of 10mm, adopting an 395/365nmLED lamp and the energy of 4000mJ/cm2Measuring the thickness of the cured part with a vernier caliper;
3. hardness: testing by using a Shore D hardness tester;
4. shear strength: reference is made to standard ISO 4587.
The test results are shown in Table 2.
As can be seen from Table 2, the ratio of the cycloaliphatic epoxy resin to the epoxy acrylate has a large influence on the adhesion, and the proportions of the cycloaliphatic epoxy resin and tricyclodecane dimethanol diacrylate have a large influence on the hardness of the colloid. The selection of the acrylic monomer has a large influence on the shear strength.
Example two
The specific raw material components of the high-weather-resistance UV thermosetting adhesive are shown in Table 3.
TABLE 3
The test results are shown in Table 4.
TABLE 4
From table 4, it can be seen that, under the condition that other components are the same, adding tetrahydrofuran acrylate alone as an acrylic monomer has an influence on the shear strength and hardness of the thermosetting adhesive, and the thermosetting adhesive needs to be mixed with other acrylic monomers for use; the thermosetting adhesive without the cationic thermal initiator has poor performance indexes, so that the addition of the thermal initiator has great influence on the performance of the thermosetting adhesive.
The alicyclic epoxy resin and the cations have high reactivity, the cations initiated by the UV section can realize primary pre-curing through the 'dark reaction' characteristic of the cations, further curing is realized after heating, and the cured product has high Tg and good substrate adhesion, so that excellent weather resistance is realized.
The above embodiments are merely illustrative of the technical ideas and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (7)
1. The high-weather-resistance UV thermosetting adhesive is characterized by comprising the following raw materials in parts by mass: 1-5 parts of component A, 1-5 parts of component B, 1-5 parts of acrylic monomer, 0.001-1 part of free radical photoinitiator, 0.001-1 part of cationic thermal initiator, 0.05-5 parts of coupling agent, 0.05-5 parts of fumed silica and 0.05-5 parts of filler, wherein the component A is epoxy acrylate with a structure shown in formula 1, and the molecular weight of the epoxy acrylate is 200-500000; the component B is alicyclic epoxy resin containing a structure shown in a formula 2,
formula 1:
formula 2:
2. the UV thermosetting adhesive with high weather resistance according to claim 1, wherein the acrylic monomer is selected from one or a mixture of isobornyl acrylate, tricyclodecane dimethanol diacrylate and tetrahydrofuran acrylate.
3. The highly weatherable UV thermoset according to claim 1, wherein said free radical photoinitiator is selected from the group consisting of benzoin diethyl ether, 1-hydroxycyclohexyl phenyl ketone, diphenyl- (2,4, 6-trimethylbenzoyl) oxyphosphorus, 2-isopropyl thioxanthone, phenyl bis (2,4, 6-trimethylbenzoyl) phosphine oxide, and mixtures thereof.
4. The UV thermosetting adhesive with high weather resistance according to claim 1, wherein the cationic photoinitiator is selected from one or more of diazonium salts, diaryliodonium salts, triarylsulfonium salts, alkylsulfonium salts, iron arene salts, sulfonyloxy ketones, and triarylsiloxy ethers.
5. The UV thermosetting adhesive with high weather resistance according to claim 1, wherein a phosphate cationic thermal initiator is used as the cationic thermal initiator.
6. The UV thermosetting adhesive with high weather resistance according to claim 1, wherein Y-glycidoxypropyltrimethoxysilane is used as the coupling agent.
7. The method for preparing the high weather resistance UV thermosetting adhesive according to any one of claims 1 to 6, which comprises the following steps:
1) adding the component A, the component B, an acrylic monomer and a free radical photoinitiator into a reaction kettle under a yellow light, and stirring until the free radical photoinitiator is completely dissolved;
2) under a yellow light, adding the coupling agent, the fumed silica and the filler into a reaction kettle, and stirring until the coupling agent, the fumed silica and the filler are completely and uniformly mixed;
3) grinding the fully mixed materials by a three-roller grinder under a yellow light until the particle size is less than 15 um;
4) adding a cationic photoinitiator and a cationic thermal initiator under a yellow light, and stirring at room temperature until the cationic photoinitiator and the cationic thermal initiator are completely and uniformly mixed;
5) discharging under a yellow light, filling, vacuum defoaming, sealing and storing in dark place.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011410633.1A CN112500823A (en) | 2020-12-06 | 2020-12-06 | High-weather-resistance UV thermosetting adhesive and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011410633.1A CN112500823A (en) | 2020-12-06 | 2020-12-06 | High-weather-resistance UV thermosetting adhesive and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112500823A true CN112500823A (en) | 2021-03-16 |
Family
ID=74970136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011410633.1A Pending CN112500823A (en) | 2020-12-06 | 2020-12-06 | High-weather-resistance UV thermosetting adhesive and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112500823A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113321912A (en) * | 2021-06-08 | 2021-08-31 | 广东工业大学 | High-temperature-resistant 3D printing photosensitive resin and preparation method and application thereof |
| CN114058320A (en) * | 2021-11-30 | 2022-02-18 | 湖南康瑄科技有限公司 | Transparent waterproof adhesive for installing luminous body and preparation method thereof |
| CN114716954A (en) * | 2022-04-22 | 2022-07-08 | 佳化化学科技发展（上海）有限公司 | Low-temperature fast-curing UV thermosetting adhesive and preparation method thereof |
| CN114874401A (en) * | 2022-03-24 | 2022-08-09 | 苏州博越新材料技术有限公司 | Photocuring anticorrosive resin ceramic composite material and preparation method thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102337099A (en) * | 2010-07-28 | 2012-02-01 | 烟台德邦电子材料有限公司 | Single-component photo-curable and thermal-curable adhesive and preparation method thereof |
| CN103087640A (en) * | 2011-11-08 | 2013-05-08 | 汉高股份有限公司 | Dual-curing adhesive composition and application thereof and method for bonding substrates |
| CN103194166A (en) * | 2013-05-06 | 2013-07-10 | 哈尔滨工业大学 | Photo-thermal double-curing conductive adhesive and preparation method thereof |
| CN104449419A (en) * | 2014-12-05 | 2015-03-25 | 烟台泰盛精化科技有限公司 | Ultraviolet-heat dual curing optical adhesive containing epoxidized polybutadiene resin |
| CN109705786A (en) * | 2018-12-26 | 2019-05-03 | 上海熙邦新材料有限公司 | Binder used for optical communication device |
-
2020
- 2020-12-06 CN CN202011410633.1A patent/CN112500823A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102337099A (en) * | 2010-07-28 | 2012-02-01 | 烟台德邦电子材料有限公司 | Single-component photo-curable and thermal-curable adhesive and preparation method thereof |
| CN103087640A (en) * | 2011-11-08 | 2013-05-08 | 汉高股份有限公司 | Dual-curing adhesive composition and application thereof and method for bonding substrates |
| CN103194166A (en) * | 2013-05-06 | 2013-07-10 | 哈尔滨工业大学 | Photo-thermal double-curing conductive adhesive and preparation method thereof |
| CN104449419A (en) * | 2014-12-05 | 2015-03-25 | 烟台泰盛精化科技有限公司 | Ultraviolet-heat dual curing optical adhesive containing epoxidized polybutadiene resin |
| CN109705786A (en) * | 2018-12-26 | 2019-05-03 | 上海熙邦新材料有限公司 | Binder used for optical communication device |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113321912A (en) * | 2021-06-08 | 2021-08-31 | 广东工业大学 | High-temperature-resistant 3D printing photosensitive resin and preparation method and application thereof |
| CN113321912B (en) * | 2021-06-08 | 2022-07-12 | 广东工业大学 | High-temperature-resistant 3D printing photosensitive resin and preparation method and application thereof |
| CN114058320A (en) * | 2021-11-30 | 2022-02-18 | 湖南康瑄科技有限公司 | Transparent waterproof adhesive for installing luminous body and preparation method thereof |
| CN114874401A (en) * | 2022-03-24 | 2022-08-09 | 苏州博越新材料技术有限公司 | Photocuring anticorrosive resin ceramic composite material and preparation method thereof |
| CN114874401B (en) * | 2022-03-24 | 2024-07-23 | 苏州博越新材料技术有限公司 | Photo-curing anti-corrosion resin ceramic composite material and preparation method thereof |
| CN114716954A (en) * | 2022-04-22 | 2022-07-08 | 佳化化学科技发展（上海）有限公司 | Low-temperature fast-curing UV thermosetting adhesive and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112500823A (en) | High-weather-resistance UV thermosetting adhesive and preparation method thereof | |
| CN101982512B (en) | Silicone acrylate coating resin and preparation method thereof | |
| CN106433536B (en) | A kind of double cured epoxy resin vinyl ester resin adhesive for underground engineering fracture plugging reinforcement | |
| WO2017181447A1 (en) | Fluid chip-level underfill resin and manufacturing method thereof | |
| CN111592849B (en) | Semi-cured epoxy adhesive film and preparation method thereof | |
| CN104479607A (en) | Low-stress transparent epoxy resin adhesive capable of curing fast at room temperature | |
| CN111363503B (en) | High-solid-content low-viscosity pressure-sensitive adhesive emulsion | |
| CN106047184A (en) | Liquid optical adhesive and 3D image structure with liquid optical adhesive | |
| CN104761994A (en) | Preparation method of photocuring organic silicon modified epoxy resin paint film | |
| CN111808568B (en) | Boiling-resistant thermal-creep-resistant environment-friendly two-component water-based solid wood plate glue main agent and preparation method thereof | |
| CN107556949B (en) | A kind of optical fiber loop adhesive glue and preparation method thereof | |
| CN112680175B (en) | But dual curing silica gel of UV moisture | |
| CN110734728A (en) | modified epoxy structural adhesive for plastic part bonding and preparation method thereof | |
| CN103045000A (en) | Special reactive type high-activity flatting agent for powder coating and preparation method thereof | |
| CN105331324A (en) | Free radical type ultraviolet light curing adhesive for optical localization and preparation method | |
| CN112175578A (en) | Transparent UV (ultraviolet) in-situ curing organosilicon sealant and preparation method thereof | |
| CN114702909B (en) | UV-thermal dual-curing adhesive and preparation method thereof | |
| TWI593738B (en) | Epoxy resin composition, epoxy cured material and led sealing material | |
| CN112280241B (en) | 3D printing photosensitive resin and preparation method and application thereof | |
| CN112852369B (en) | High-temperature-resistant epoxy adhesive and preparation method thereof | |
| CN112011256A (en) | UV thermosetting adhesive and preparation method thereof | |
| CN109134825A (en) | Modified epoxy and its preparation and application | |
| CN107384271A (en) | A kind of thread locking anaerobic adhesive and preparation method thereof | |
| US20030105179A1 (en) | Photopolymerizable epoxy composition | |
| CN110791235A (en) | Intelligent watch sealant and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20210316 |