CN111234756B - UV-anaerobic dual-mode curing bonding material - Google Patents
UV-anaerobic dual-mode curing bonding material Download PDFInfo
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- CN111234756B CN111234756B CN202010157327.5A CN202010157327A CN111234756B CN 111234756 B CN111234756 B CN 111234756B CN 202010157327 A CN202010157327 A CN 202010157327A CN 111234756 B CN111234756 B CN 111234756B
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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
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
- C09J171/02—Polyalkylene oxides
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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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- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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- 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
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a UV-anaerobic dual-mode curing bonding material which comprises the following raw materials in parts by weight: 10-40 parts by weight of hydroxy methacrylate; 20-30 parts of hydroxyl acrylate; 10-15 parts of polyethylene glycol methacrylate; 10-15 parts of polyethylene glycol acrylate; 17-24 parts by weight of acryloyl morpholine; 0.5-1 part by weight of a free radical initiator; 0.5-1.0 part by weight of an oxidant; 0.1-0.5 part by weight of a reducing agent; 0.5-1.0 part by weight of adhesion promoter; 1.0-1.7 parts by weight of a polymerization inhibitor; 0.4-0.8 part of stabilizer. The invention has the characteristics of low viscosity, small shrinkage stress, proper bonding strength and easy degumming in hot water.
Description
Technical Field
The invention belongs to the technical field of high polymer materials, and particularly relates to a preparation method of a UV-anaerobic dual-mode curing bonding material.
Background
The UV curing adhesive is a single-component adhesive which is polymerized and cross-linked and cured between molecules under the irradiation of UV light. The UV curing adhesive is developed in the fifties of the last century, has the characteristics of high efficiency, energy conservation, environmental protection, quickness and single component, and has attracted the wide interest and research of material scientists once coming out. However, the UV curing adhesive has very short curing reaction time, so that the volume shrinkage rate is obviously increased after curing. In addition, for the bonding of glass-cut materials with low transparency or complicated geometric curves, the curing of UV-curing adhesives and hot water degumming are difficult to accomplish.
The invention patent of Ligang, a synthetic material industry research institute of Tianjin, and the like, a single-component ultraviolet light-anaerobic dual-curing adhesive (patent number: 201310289458.9) adopts ultraviolet light free radical and anaerobic dual-curing initiator, and the shear strength of the obtained adhesive is 45 MPa. However, in the composition, the content of high molecular weight epoxy acrylate and polyurethane acrylate is more than 60 percent, so that the shrinkage stress is large, and the degumming in hot water is difficult.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a preparation method of a UV-anaerobic dual-mode curing bonding material, which is suitable for bonding a glass cutting material with a low transparency or a complicated geometric curved surface.
The UV-anaerobic dual-mode curing bonding material comprises the following raw materials in parts by weight:
10-40 parts by weight of hydroxy methacrylate
20-30 parts by weight of hydroxy acrylate
10-15 parts by weight of polyethylene glycol methacrylate
10-15 parts by weight of polyethylene glycol acrylate
17-24 parts by weight of acryloyl morpholine
0.5-1.0 part by weight of free radical initiator
0.5 to 1.0 part by weight of an oxidizing agent
0.1 to 0.5 part by weight of reducing agent
0.5-1.0 part by weight of adhesion promoter
1.0-1.7 parts by weight of polymerization inhibitor
0.4-0.8 part of stabilizer.
The hydroxyl methacrylate is one of hydroxypropyl methacrylate or hydroxyethyl methacrylate;
the hydroxyl acrylate is one of hydroxypropyl acrylate or hydroxyethyl acrylate;
the polyethylene glycol methacrylate is one of polyethylene glycol (200) dimethacrylate, polyethylene glycol (400) dimethacrylate or polyethylene glycol (600) dimethacrylate;
the polyethylene glycol acrylate is one of polyethylene glycol (200) diacrylate, polyethylene glycol (400) diacrylate or polyethylene glycol (600) diacrylate;
the free radical initiator is one of 2-hydroxy-2-methyl-1-phenyl acetone (1173), 1-hydroxycyclohexyl phenyl ketone (184), 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-propanone (907), 2, 4, 6-trimethylbenzoyl-diphenyl phosphine oxide (TPO) and benzoin dimethyl ether (651);
the oxidant is one of cumene hydroperoxide, butanone peroxide or dicumyl peroxide;
the reducing agent is one of N, N-dimethylaniline, acetanilide or 1,2,3, 4-tetrahydroquinoline;
the adhesion promoter is sulfhydryl polyethylene glycol acrylate with molecular weight of 400, 600 or 1000;
the polymerization inhibitor is one of hydroquinone, p-methoxyphenol or 2, 6-di-tert-butyl-p-cresol;
the stabilizer is 8 wt% of disodium ethylene diamine tetraacetate aqueous solution.
The invention also provides a preparation method of the UV-anaerobic dual-mode curing bonding material, which comprises the following specific steps:
the components are sequentially added into a reaction kettle according to the amount, and the mixture is uniformly stirred and filled into a lightproof container.
The invention abandons the prepolymer with high molecular weight used in the traditional UV glue, combines the UV-anaerobic dual-mode curing, the water-soluble monomer and the specific adhesion promoter, and the obtained UV-anaerobic dual-mode curing bonding material is suitable for bonding glass cutting materials with low transparency or complex geometric curved surfaces and has the characteristics of low viscosity, small shrinkage stress, proper bonding strength and easy degumming in hot water.
Detailed Description
The present invention is further analyzed with reference to the following specific examples.
Example 1:
the UV-anaerobic dual-mode curing bonding material comprises the following raw materials in parts by weight:
10 parts by weight of hydroxypropyl methacrylate
30 parts by weight of hydroxypropyl acrylate
Polyethylene glycol (200) dimethacrylate 15 parts by weight
10 parts by weight of polyethylene glycol (200) diacrylate
24 parts by weight of acryloyl morpholine
0.5 part by weight of 2-hydroxy-2-methyl-1-phenylpropanone (1173)
0.5 part by weight of cumene hydroperoxide
0.1 part by weight of N, N-dimethylaniline
0.5 part by weight of sulfhydryl polyethylene glycol acrylate (400)
1.7 parts of hydroquinone
0.4 part by weight of 8 wt% disodium ethylene diamine tetraacetate aqueous solution.
The components are sequentially added into a reaction kettle according to the amount, and the mixture is uniformly stirred and filled into a lightproof container.
Example 2
The UV-anaerobic dual-mode curing bonding material comprises the following raw materials in parts by weight:
40 parts by weight of hydroxyethyl methacrylate
20 parts of hydroxyethyl acrylate
Polyethylene glycol (400) dimethacrylate 15 parts by weight
15 parts by weight of polyethylene glycol (400) diacrylate
24 parts by weight of acryloyl morpholine
1.0 part by weight of 1-hydroxycyclohexyl phenyl ketone (184)
1.0 part by weight of butanone peroxide
0.5 part by weight of acetylphenylhydrazine
1.0 part by weight of sulfhydryl polyethylene glycol acrylate (600)
1.7 parts by weight of p-methoxyphenol
0.8 part by weight of 8 wt% disodium ethylene diamine tetraacetate aqueous solution.
The components are sequentially added into a reaction kettle according to the amount, and the mixture is uniformly stirred and filled into a lightproof container.
Example 3
The UV-anaerobic dual-mode curing bonding material comprises the following raw materials in parts by weight:
20 parts by weight of hydroxypropyl methacrylate
25 parts of hydroxyethyl acrylate
12 parts by weight of polyethylene glycol (600) dimethacrylate
11 parts by weight of polyethylene glycol (600) diacrylate
19 parts by weight of acryloyl morpholine
0.7 part by weight of 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-propanone (907)
Dicumyl peroxide 0.9 weight portion
0.3 part by weight of 1,2,3, 4-tetrahydroquinoline
0.8 part by weight of sulfhydryl polyethylene glycol acrylate (1000)
1.4 parts by weight of 2, 6-di-tert-butyl-p-cresol
0.6 part by weight of 8 wt% disodium ethylene diamine tetraacetate aqueous solution.
The components are sequentially added into a reaction kettle according to the amount, and the mixture is uniformly stirred and filled into a lightproof container.
Example 4
The UV-anaerobic dual-mode curing bonding material comprises the following raw materials in parts by weight:
36 parts by weight of hydroxyethyl methacrylate
23 parts of hydroxypropyl acrylate
Polyethylene glycol (200) dimethacrylate 13 parts by weight
14 parts by weight of polyethylene glycol (400) diacrylate
21 parts by weight of acryloyl morpholine
0.7 parts by weight of 2, 4, 6-trimethylbenzoyl-diphenylphosphine oxide (TPO)
0.6 part by weight of butanone peroxide
0.2 part by weight of acetylphenylhydrazine
0.8 part by weight of sulfhydryl polyethylene glycol acrylate (600)
1.5 parts by weight of 2, 6-di-tert-butyl-p-cresol
0.7 part by weight of 8 wt% disodium ethylene diamine tetraacetate aqueous solution.
The components are sequentially added into a reaction kettle according to the amount, and the mixture is uniformly stirred and filled into a lightproof container.
Example 5
The UV-anaerobic dual-mode curing bonding material comprises the following raw materials in parts by weight:
29 parts by weight of hydroxypropyl methacrylate
24 parts of hydroxyethyl acrylate
11 parts by weight of polyethylene glycol (600) dimethacrylate
12 parts by weight of polyethylene glycol (400) diacrylate
Acryloyl morpholine 22 weight portions
Benzoin dimethyl ether (651) 0.9 weight portion
Dicumyl peroxide 0.6 weight portion
0.3 part by weight of 1,2,3, 4-tetrahydroquinoline
0.8 part by weight of sulfhydryl polyethylene glycol acrylate (400)
1.6 parts of hydroquinone
0.7 part by weight of 8 wt% ethylene diamine tetraacetic acid disodium solution
The components are sequentially added into a reaction kettle according to the amount, and the mixture is uniformly stirred and filled into a lightproof container.
Experimental items and methods:
1. tensile shear Strength test
According to the national standard GB/T7124-2008 "determination of tensile shear strength of adhesive (rigid material to rigid material)", according to the actual use condition of the project, a glass test piece with length multiplied by width multiplied by thickness of 60 mm multiplied by 20mm multiplied by 5 mm is adopted to carry out lap joint (lap joint length of 10 mm) by curing the adhesive material by using the UV-anaerobic dual mode of the experiment, a UV lamp with 40W is used for irradiating for 1min at a distance of 5cm from the bonding part, and then the glass test piece is placed for 2 hours. Two ends of the sample are respectively lapped with glass by using polished steel sheets with the length multiplied by the width multiplied by the thickness multiplied by 80mm multiplied by 20mm multiplied by 2 mm, and are adhered by epoxy glue (the lapping length is 20mm, the lapping surfaces and the lapping surfaces between the glass are on the same plane), and the steel sheets are clamped after the epoxy glue is completely cured to carry out tensile shear strength test.
2. And (3) determining the degumming time in water:
a glass test piece with a length of 60 mm, a width of 60 mm and a thickness of 20mm, 5 mm was lapped with the UV-anaerobic dual-curing adhesive material of this experiment (lap length 10 mm), irradiated with a 40W UV lamp for 1min at a distance of 5cm from the bonded portion, and then left for 2 hours. The glass straps were hung in hot water at 65 ℃ and the time to glass separation was recorded.
TABLE 1 Properties of the UV-anaerobic dual mode curing adhesive materials prepared in examples 1 to 5 are shown in the following table.
| Sample (I) | Tensile shear Strength (MPa) | Degumming time (min ℃) |
| Example 1 | 11.5 | 11 |
| Example 2 | 10.5 | 13 |
| Example 3 | 10.2 | 13 |
| Example 4 | 10.0 | 16 |
| Example 5 | 10.3 | 15 |
The above embodiments are not intended to limit the present invention, and the present invention is not limited to the above embodiments, and all embodiments are within the scope of the present invention as long as the requirements of the present invention are met.
Claims (8)
1. The UV-anaerobic dual-mode curing bonding material is characterized by comprising the following raw materials in parts by weight:
10-40 parts by weight of hydroxy methacrylate
20-30 parts by weight of hydroxy acrylate
10-15 parts by weight of polyethylene glycol methacrylate
10-15 parts by weight of polyethylene glycol acrylate
17-24 parts by weight of acryloyl morpholine
0.5-1 part by weight of free radical initiator
0.5 to 1.0 part by weight of an oxidizing agent
0.1 to 0.5 part by weight of reducing agent
0.5-1.0 part by weight of adhesion promoter
1.0-1.7 parts by weight of polymerization inhibitor
0.4-0.8 part by weight of a stabilizer;
the polyethylene glycol acrylate is one of polyethylene glycol (200) diacrylate, polyethylene glycol (400) diacrylate or polyethylene glycol (600) diacrylate;
the reducing agent is one of N, N-dimethylaniline, acetanilide or 1,2,3, 4-tetrahydroquinoline; the adhesion promoter is sulfhydryl polyethylene glycol acrylate with molecular weight of 400, 600 or 1000; the polymerization inhibitor is one of hydroquinone, p-methoxyphenol or 2, 6-di-tert-butyl-p-cresol.
2. The UV-anaerobic dual mode curing bonding material of claim 1, wherein the hydroxy methacrylate is one of hydroxypropyl methacrylate or hydroxyethyl methacrylate.
3. The UV-anaerobic dual mode curing bonding material of claim 1, wherein the hydroxy acrylate is one of hydroxypropyl acrylate or hydroxyethyl acrylate.
4. The UV-anaerobic dual mode curing bonding material of claim 1, wherein the polyethylene glycol methacrylate is one of polyethylene glycol (200) dimethacrylate, polyethylene glycol (400) dimethacrylate or polyethylene glycol (600) dimethacrylate.
5. The UV-anaerobic dual mode curing adhesive material according to claim 1, wherein the radical initiator is one of 2-hydroxy-2-methyl-1-phenyl acetone (1173), 1-hydroxycyclohexyl phenyl ketone (184), 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-propanone (907), 2, 4, 6-trimethylbenzoyl-diphenyl phosphine oxide (TPO), benzoin dimethyl ether (651).
6. The dual UV-anaerobic curable bonding material according to claim 1, wherein the oxidizing agent is one of cumene hydroperoxide, butanone peroxide or dicumyl peroxide.
7. The UV-anaerobic dual mode curing cementitious material of claim 1, wherein the stabilizer is an 8 wt% disodium ethylenediaminetetraacetate aqueous solution.
8. A method for preparing the UV-anaerobic dual-mode curing adhesive material as claimed in any one of claims 1 to 7, wherein the above components are sequentially added into a reaction kettle according to the amount, stirred uniformly and filled into a lightproof container.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202010157327.5A CN111234756B (en) | 2020-03-09 | 2020-03-09 | UV-anaerobic dual-mode curing bonding material |
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| CN202010157327.5A CN111234756B (en) | 2020-03-09 | 2020-03-09 | UV-anaerobic dual-mode curing bonding material |
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| CN111234756B true CN111234756B (en) | 2021-12-07 |
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| CN112778914B (en) * | 2021-01-21 | 2023-01-20 | 杭州华圩新材料科技有限公司 | Ultraviolet curing adhesive for high-performance touch screen toughened film and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005103178A1 (en) * | 2004-03-29 | 2005-11-03 | Avery Dennison Corporation | Anaerobic pressure sensitive adhesive |
| CN101392151A (en) * | 2008-10-30 | 2009-03-25 | 广东恒大新材料科技有限公司 | Ultraviolet ray/anaerobic dual curing binding agent and preparation method thereof |
| CN107841279A (en) * | 2017-11-22 | 2018-03-27 | 中昊北方涂料工业研究设计院有限公司 | A kind of single-component anaerobic type acrylate adhesive |
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- 2020-03-09 CN CN202010157327.5A patent/CN111234756B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005103178A1 (en) * | 2004-03-29 | 2005-11-03 | Avery Dennison Corporation | Anaerobic pressure sensitive adhesive |
| CN101392151A (en) * | 2008-10-30 | 2009-03-25 | 广东恒大新材料科技有限公司 | Ultraviolet ray/anaerobic dual curing binding agent and preparation method thereof |
| CN107841279A (en) * | 2017-11-22 | 2018-03-27 | 中昊北方涂料工业研究设计院有限公司 | A kind of single-component anaerobic type acrylate adhesive |
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