CN111909643B - Time-delay photocuring epoxy resin composition and application thereof - Google Patents
Time-delay photocuring epoxy resin composition and application thereof Download PDFInfo
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- CN111909643B CN111909643B CN202010653286.9A CN202010653286A CN111909643B CN 111909643 B CN111909643 B CN 111909643B CN 202010653286 A CN202010653286 A CN 202010653286A CN 111909643 B CN111909643 B CN 111909643B
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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
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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
- 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
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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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention relates to a time-delay photocuring epoxy resin composition and application thereof, wherein the composition comprises the following raw material components in percentage by mass: 45-60% of alicyclic epoxy resin; 2-8% of an inorganic filler; 10-20% of difunctional oxetane; 15-30% of a chain transfer agent; 0.5-1.5% of cationic photoinitiator; 0.5-1.5% of photosensitive sensitizer. The comprehensive synergistic effect is generated by introducing a special chain transfer agent, a cationic photoinitiator and a photosensitive sensitizer into the alicyclic epoxy resin: the time-delay curing characteristic of the UVLED surface light source (395nm wavelength) after illumination can be realized; the time delay is controllable, the bonding force is excellent, and the cured material has thermal reworkability at 80-100 ℃.
Description
Technical Field
The invention belongs to the field of high polymer material compounding, relates to a resin composition, and particularly relates to a time-delay photocuring epoxy resin composition and application thereof.
Background
The UV curing process has the characteristics of normal-temperature curing, high curing rate, good performance of cured products and the like, and is widely applied to the fields of coatings, printing ink, electronic packaging materials, medical materials and the like. The alicyclic epoxy resin UV cationic photocuring system has the advantages of high curing speed, high curing depth, low shrinkage, no oxygen resistance and the like, and excellent mechanical strength and bonding strength after curing, and is widely applied to the field of electronic packaging and bonding. However, due to the characteristics of the epoxy resin, the cured system has high crosslinking density and poor toughness of the material, so that the application of the epoxy resin in some specific packaging fields is limited, and particularly the adhesion of the epoxy resin to opaque materials is limited.
For adhesive applications, UV glue is cured by UV irradiation, which requires at least one of the two adherends to be transparent due to its high curing rate. For both opaque materials, UV glue is often not practical.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a time-delay photocuring epoxy resin composition.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows: the time-delay photocuring epoxy resin composition comprises the following raw material components in percentage by mass, wherein the sum of the mass percentages of the raw material components is 100%:
optimally, the feed comprises the following raw material components in percentage by mass:
further, the feed comprises the following raw material components in percentage by mass:
preferably, the alicyclic epoxy resin is selected from the group consisting of 3, 4-epoxycyclohexylmethyl-3, 4-epoxycyclohexyl formate, bis (7-oxabicyclo [4.1.0] 3-heptamethyl) adipate, 1, 2-epoxy-4-vinylcyclohexane, methyl 3, 4-epoxycyclohexanecarboxylate, diglycidyl 4, 5-epoxycyclohexane-1, 2-dicarboxylate, a mixture of one or more of hexahydrophthalic acid diglycidyl ester, 4-diaminodicyclohexylmethane glycidyl amine resin, 1, 4-cyclohexanedimethanol bis (3, 4-epoxycyclohexanecarboxylate) ester, 3, 9-divinyl-2, 4,8, 10-tetraoxaspiro [5.5] undecane and dicyclopentadiene dioxide.
Preferably, the difunctional oxetane is a mixture of one or more selected from the group consisting of 3,3'- (oxybispropylene) bis (3-ethyl) oxetane, 3-ethyl-3- [ (oxiranyloxymethoxy) methyl ] oxetane, 3-ethyl-3- [4- [ (3-ethyloxetan-3-yl) methoxy ] butoxymethyl ] oxetane, 1, 4-bis [ (3-ethyl-3-oxetanylmethoxy) methyl ] benzene and 4,4' -bis [ (3-ethyl-3-oxetanyl) methoxymethyl ] biphenyl.
Optimally, the inorganic filler is white carbon black; the chain transfer agent is a polyglycol.
Further, the cationic photoinitiator is one or more selected from the group consisting of ferrocenium salts, diaryl iodates and triaryl sulfonates. Specifically, the cationic photoinitiator is eta 6-cumeneiron (II) hexafluorophosphate.
Preferably, the photosensitizing agent is an anthraquinone derivative.
The invention also aims to provide application of the time-lapse light-cured epoxy resin composition as an encapsulating adhesive of a non-transparent material.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages: the delayed photocuring epoxy resin composition of the invention generates comprehensive synergistic effect by introducing a special chain transfer agent, a cationic photoinitiator and a photosensitizing agent into alicyclic epoxy resin: the time-delay curing characteristic of the UVLED surface light source (365nm and 395nm wavelength) after illumination can be realized; the time delay is controllable, the bonding force is excellent, and the cured material has thermal reworkability at 80-100 ℃; the application of the UV delayed photo-curing adhesive (such as the adhesion of two non-transparent materials, the adhesion of a rear cover of a mobile phone and the like) can be greatly widened; the hot reworkability can be realized, the hot-melt adhesive can be opened for multiple times, the good adhesive force can be continuously kept, and certain application scenes of hot melt adhesives can be replaced.
Detailed Description
The delayed photocuring epoxy resin composition comprises the following raw material components in percentage by mass: 45-60% of alicyclic epoxy resin; 2-8% of an inorganic filler; 10-20% of difunctional oxetane; 15-30% of a chain transfer agent; 0.5-1.5% of cationic photoinitiator; 0.5-1.5% of photosensitive sensitizer. The comprehensive synergistic effect is generated by introducing a special chain transfer agent, a cationic photoinitiator and a photosensitive sensitizer into the alicyclic epoxy resin: the time-delay curing characteristic of the UVLED surface light source (395nm wavelength) after illumination can be realized; the time delay is controllable, the bonding force is excellent, and the cured material has thermal reworkability at 80-100 ℃; the application of the UV delayed photo-curing adhesive (such as the adhesion of two non-transparent materials, the adhesion of a rear cover of a mobile phone and the like) can be greatly widened; the hot reworkability can be realized, the hot-melt adhesive can be opened for multiple times, the good adhesive force can be continuously kept, and certain application scenes of hot melt adhesives can be replaced.
The time-lapse light-curable epoxy resin composition preferably comprises the following raw material components in mass content: 50-55% of alicyclic epoxy resin; 4.5-7.0% of inorganic filler; 12-18% of difunctional oxetane; 20-25% of a chain transfer agent; 0.8-1.25% of cationic photoinitiator; 0.8-1.25% of photosensitive sensitizer. The material optimally comprises the following raw material components in percentage by mass: alicyclic epoxy resin 52.5%; 5.9 percent of inorganic filler; difunctional oxetane 15.8%; 23.6 percent of chain transfer agent; 1.1% of cationic photoinitiator; 1.1% of photosensitive sensitizer; at the moment, the time delay range can be controlled within 1-10 min, and the bonding performance is better.
The alicyclic epoxy resin is selected from 3, 4-epoxycyclohexylmethyl-3, 4-epoxycyclohexyl formate, bis (7-oxabicyclo [4.1.0] 3-heptamethyl) adipate, 1, 2-epoxy-4-vinylcyclohexane, methyl 3, 4-epoxycyclohexanecarboxylate, diglycidyl 4, 5-epoxycyclohexane-1, 2-dicarboxylate, a mixture of one or more of diglycidyl hexahydrophthalate, 4-diaminodicyclohexylmethane glycidyl amine resin, 1, 4-cyclohexanedimethanol bis (3, 4-epoxycyclohexanecarboxylate) ester, 3, 9-divinyl-2, 4,8, 10-tetraoxaspiro [5.5] undecane and dicyclopentadiene dioxide; specifically, commercially available conventional brands such as 2021P, TTA21P, TTA26, TTA28, TTA34, TTA2083, TTA27, and TTA60 may be used. The difunctional oxetane is a mixture of one or more selected from the group consisting of 3,3'- (oxybis-methylene) bis (3-ethyl) oxetane, 3-ethyl-3- [ (oxiranyloxymethoxy) methyl ] oxetane, 3-ethyl-3- [4- [ (3-ethyloxetan-3-yl) methoxy ] butoxymethyl ] oxetane, 1, 4-bis [ (3-ethyl-3-oxetanylmethoxy) methyl ] benzene, 4' -bis [ (3-ethyl-3-oxetanyl) methoxymethyl ] biphenyl; specifically, commercially available conventional brands such as TCM-201, TCM-207, TCM-218, TCM-203, TCM-204, and the like may be used.
The inorganic filler is white carbon black which is commercially available and has a conventional grade. The chain transfer agent is polyglycol, preferably polyethylene glycol (the number average molecular weight is preferably 400-1000, and the best is 600). The cationic photoinitiator is one or more selected from ferrocenium salt, diaryl iodate and triaryl sulfonate, and is preferably eta 6-cumeneiron (II) hexafluorophosphate. The photosensitizing agent is an anthraquinone derivative, and specifically, those of commercially available conventional brands, such as PAS33, etc., can be used.
The time-delay light-cured epoxy resin composition is used as the packaging adhesive of the non-transparent material, can greatly widen the application range of the UV time-delay light-cured packaging adhesive (such as the bonding of two non-transparent materials and the bonding of a rear cover of a mobile phone), has thermal reworkability, can be opened for many times, continuously keeps good bonding force, and can replace the application scenes of certain hot melt adhesives.
The following detailed description of preferred embodiments of the invention is provided:
examples 1 to 5
Examples 1 to 5 each provide a time-lapse photocurable epoxy resin composition, the specific raw material components of which are shown in table 1.
TABLE 1 raw Material Components of time-lapse photocurable epoxy resin compositions in examples 1 to 5
The preparation method of the time-delay photocuring epoxy resin composition comprises the following steps: weighing the components in proportion, premixing the components by using a high-speed dispersion mixer, and performing vacuum mixing and defoaming by using a planetary mixer to prepare the final composition.
Comparative examples 1 to 10
Comparative examples 1 to 10 each provide an epoxy resin composition, the specific components of which are shown in Table 2.
TABLE 2 raw material components for epoxy resin compositions in comparative examples 1 to 10
Note: the cationic photoinitiators in comparative examples 1 to 5, comparative examples 7 to 8 and comparative example 10 were η 6-cumeneiron (ii) hexafluorophosphate, and the cationic photoinitiator in comparative example 9 was a triarylsulfonium salt-based cationic photoinitiator 1176; the cycloaliphatic epoxy resin in comparative examples 1-9 was 2021P, while the epoxy resin in comparative example 10 was bisphenol a epoxy resin 828.
The epoxy resin compositions of examples 1 to 5 and comparative examples 1 to 10 were subjected to performance tests, and the results are shown in tables 3,4, 5 and 6.
TABLE 3 Performance test Table for epoxy resin compositions of examples 1 to 5 and comparative examples 1 to 10
| Examples | Viscosity (cP) | Thixotropic (0.5/5) | Open time(s) | Hardness shoreA | Specific gravity of |
| Example 1 | 10900 | 11.5 | 1min15s | 50 | 1.27 |
| Example 2 | 12850 | 14.6 | 50s | 78 | 1.31 |
| Example 3 | 8950 | 8.9 | 2min20s | 25 | 1.15 |
| Example 4 | 10580 | 12.2 | 1min10s | 55 | 1.24 |
| Example 5 | 10230 | 10.7 | 1min30s | 43 | 1.26 |
| Comparative example 1 | 5846 | 7.8 | 5s | 80 | 1.11 |
| Comparative example 2 | 25800 | 15.8 | Not cured | - | 1.35 |
| Comparative example 3 | 102 | 1 | 1min15s | 50 | 1.06 |
| Comparative example 4 | 16500 | 12.3 | Not cured | - | 1.28 |
| Comparative example 5 | 17860 | 13.1 | 0s | 100 | 1.30 |
| Comparative example 6 | 10866 | 11.5 | Not cured | - | 1.27 |
| Comparative example 7 | 10680 | 11.5 | Not cured | - | 1.27 |
| Comparative example 8 | Semi-solid | - | 0s | - | 1.32 |
| Comparative example 9 | 10980 | 11.5 | Not cured | - | 1.27 |
| Comparative example 10 | 14560 | 11.8 | Not cured | - | 1.30 |
Note: the test conditions for tack-free time and hardness shoreA are note: the curing condition is that the 395nm wavelength LED surface light source is 283mW/cm2The irradiation is carried out for 12 s.
TABLE 4 full curing data of epoxy resin compositions in examples 1-5 and comparative examples 1-10
Note: in 395nm LED area light source with 283mW/cm2The irradiation is carried out for 60 s.
0.2g of the epoxy resin compositions of examples 1 to 5 and comparative examples 1 to 10 was dispensed from a dropper, and coated on a PCB board of 200mm X20 mm, and a cover glass of the same size was put thereon, and the movable time was confirmed by hand after light irradiation, and the results are shown in Table 5.
TABLE 5 data table of moving time after light irradiation of epoxy resin compositions in examples 1 to 5 and comparative examples 1 to 10
Note: the curing condition is that the 395nm wavelength LED surface light source is 283mW/cm2The irradiation is carried out for 12 s.
TABLE 6 data table of changes with time in adhesion after light irradiation of epoxy resin compositions in examples 1 to 5 and comparative examples 1 to 10
Note: the curing condition is that the 395nm wavelength LED surface light source is 283mW/cm2Irradiating for 12s, and testing the shear strength (MPa) of PCB-PCB after different time after irradiation.
While the present application has been described with embodiments, those skilled in the art will appreciate that there are numerous variations and permutations of the present application without departing from the spirit of the application, and it is intended that the appended claims encompass such variations and modifications without departing from the spirit of the application.
Claims (5)
1. The time-delay photocuring epoxy resin composition is characterized by comprising the following raw material components in percentage by mass:
45-60% of alicyclic epoxy resin;
2-8% of an inorganic filler;
10-20% of difunctional oxetane;
15-30% of a chain transfer agent;
0.5-1.5% of cationic photoinitiator;
0.5-1.5% of photosensitive sensitizer;
the sum of the mass percentages of the raw material components is 100%;
the alicyclic epoxy resin is selected from 3, 4-epoxycyclohexylmethyl-3, 4-epoxycyclohexyl formate, bis (7-oxabicyclo [4.1.0] 3-heptamethyl) adipate, 1, 2-epoxy-4-vinylcyclohexane, 3, 4-epoxycyclohexanecarboxylic acid methyl ester, 4, 5-epoxycyclohexane-1, 2-dicarboxylic acid diglycidyl ester, a mixture of one or more of diglycidyl hexahydrophthalate, 4-diaminodicyclohexylmethane glycidyl amine resin, 1, 4-cyclohexanedimethanol bis (3, 4-epoxycyclohexanecarboxylate) ester, 3, 9-divinyl-2, 4,8, 10-tetraoxaspiro [5.5] undecane and dicyclopentadiene dioxide;
the difunctional oxetane is a mixture of one or more selected from the group consisting of 3,3'- (oxybispropylene) bis (3-ethyl) oxetane, 3-ethyl-3- [ (oxiranyloxymethoxy) methyl ] oxetane, 3-ethyl-3- [4- [ (3-ethyloxetan-3-yl) methoxy ] butoxymethyl ] oxetane, 1, 4-bis [ (3-ethyl-3-oxetanylmethoxy) methyl ] benzene and 4,4' -bis [ (3-ethyl-3-oxetanyl) methoxymethyl ] biphenyl;
the inorganic filler is white carbon black; the chain transfer agent is polyglycol; the cationic photoinitiator is one or more selected from ferrocenium salt, diaryl iodate and triaryl sulfonate, and the photosensitive sensitizer is anthraquinone derivative.
2. The time-lapse photocurable epoxy resin composition according to claim 1, characterized in that it comprises the following raw material components in mass content:
50-55% of alicyclic epoxy resin;
4.5-7.0% of inorganic filler;
12-18% of difunctional oxetane;
20-25% of a chain transfer agent;
0.8-1.25% of cationic photoinitiator;
0.8-1.25% of photosensitive sensitizer;
the sum of the mass percentages of the raw material components is 100%.
3. The time-lapse photocurable epoxy resin composition according to claim 2, characterized in that it comprises the following raw material components in mass content:
alicyclic epoxy resin 52.5%;
5.9 percent of inorganic filler;
difunctional oxetane 15.8%;
23.6 percent of chain transfer agent;
1.1% of cationic photoinitiator;
1.1% of photosensitive sensitizer.
4. The time-lapse photocurable epoxy resin composition according to claim 1, wherein: the cationic photoinitiator is one or more selected from ferrocenium salt, diaryl iodate and triaryl sulfonate.
5. Use of the time-lapse photocurable epoxy resin composition according to any one of claims 1 to 4, wherein: the packaging adhesive is used as a non-transparent material.
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| CN114507416A (en) * | 2020-11-16 | 2022-05-17 | 常州强力先端电子材料有限公司 | Photocuring composition, coating and preparation method thereof, carbon fiber prepreg and preparation method thereof, and fiber composite material |
| CN114507479B (en) * | 2020-11-16 | 2023-12-15 | 常州强力先端电子材料有限公司 | Photocurable composition, binder, preparation method of binder and bonding method of substrate |
| CN113201203A (en) * | 2021-03-15 | 2021-08-03 | 苏州市汇涌进光电有限公司 | Light-cured transparent epoxy material and application thereof |
| CN114479735A (en) * | 2022-02-14 | 2022-05-13 | 张河远 | Cationic UV curing adhesive and preparation method and application thereof |
| CN115716908B (en) * | 2022-11-21 | 2024-08-02 | 武汉轻工大学 | Method for synthesizing medium-high molecular weight alicyclic epoxy resin and application thereof in field of photoelectron packaging |
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