CN1632024A - Structural pressure-sensitive adhesive - Google Patents
Structural pressure-sensitive adhesive Download PDFInfo
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- CN1632024A CN1632024A CN 200410077517 CN200410077517A CN1632024A CN 1632024 A CN1632024 A CN 1632024A CN 200410077517 CN200410077517 CN 200410077517 CN 200410077517 A CN200410077517 A CN 200410077517A CN 1632024 A CN1632024 A CN 1632024A
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- sensitive adhesive
- glycidyl
- epoxy
- ether
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Abstract
The invention relates to a structure pressure sensitive adhesive,which is comprised of the following ones: flexible polymer with epoxide group 20-80, epoxide resin 20-80,active diluents 0.5-20, curing agent 0.1-20, and the sun of portions of flexible polymer with epoxide group and epoxide resin is 100. The invention can be applied in preparation of pressure sensitive adhesive slice or pressure sensitive adhesive belt with outstanding resistance to aging, good forming performance and high adhering strength after being solidified.
Description
Technical field
The present invention relates to be used to make the structural pressure-sensitive adhesive of pressure sensitive adhesion sheet or pressure-sensitive adhesive tape.Pressure sensitive adhesion sheet that this kind structural pressure-sensitive adhesive is made or pressure-sensitive adhesive tape have pressure-sensitive preferably before use, can further solidify after the use, make it to present the performance of construction adhesive.
Background technology
With paper, plastic film and fabric etc. as base material, pressure-sensitive adhesive tape based on acrylic psa, has excellent ageing-resistant performance, be characterized in that gently depress can be instantaneous bonding, has advantage easy to use and the raising work efficiency, but its bonding strength is lower, can not be used for stressed bigger occasion.For overcoming this performance deficiency of pressure sensitive adhesive, existing patent is intended to develop and a kind ofly can guarantees better pressure-sensitive before use before the present invention, and after use further solidified structure pressure-sensitive adhesive tape.
(its intermediate materials-telechelic polymer needs with anionic polymerisation process synthetic Chinese patent for publication number, the CN1160416) dual cure systems of distant pawl of employing and heterotelechelic polymers, and preparation is difficulty.And because of adopting conjugated diene as raw material, products therefrom contains double bond structure, and Zhi Bei pressure-sensitive adhesive tape is aging easily thus, if double bond containing telechelic polymer is carried out hydrogen treatment, though can improve its ageing-resistant performance, can increase manufacturing cost.U.S.Patent 6211261 selects the acrylic polymers/Resins, epoxy that contains carboxylic acid and the system of usefulness for use, the good structure pressure sensitive adhesive of preparation ageing-resistant performance.Owing to there is bigger reactivity between hydroxy-acid group and the epoxide group, part crosslinking reaction, particularly content of epoxy resin also can take place when storage at normal temperature when big, in storage period, easily solidify, thereby lose pressure-sensitive.If content of epoxy resin is less, then the final bonding strength of structure pressure-sensitive adhesive tape of preparation is not high thus.
Summary of the invention
The objective of the invention is to defective at the prior art existence, a kind of structural pressure-sensitive adhesive is provided, is used to prepare that ageing-resistant performance is good, pressure-sensitive outstanding, has pressure sensitive adhesion sheet or pressure-sensitive adhesive tape after good moldability and the curing than high-adhesive-strength.
Structural pressure-sensitive adhesive of the present invention is made up of the component of following mass fraction:
The flexible polymer 20-80 that contains epoxide group
Resins, epoxy 20-80
Reactive thinner 0.5-20
Latent curing agent 0.1-20
Containing the flexible polymer of epoxide group and the umber sum of Resins, epoxy is 100;
The described flexible polymer that contains epoxide group, the consumption of its optimization are 40-70 part quality; Its epoxy equivalent (weight) is 300-10000g/mol, second-order transition temperature (T
g) be-70-20 ℃, preferred range is-40-0 ℃;
The described flexible polymer that contains epoxide group is made by the monomer copolymerization of following structure:
(1) acrylic monomer of general formula (I)
CH
2=C(R
1)COOR
2 (I)
R in the formula
1Represent hydrogen atom or methyl; R
2Represent the alkyl of 2-14 carbon atom;
(2) contain the monomer of epoxide group and two keys, comprise acrylic ester monomer, methyl acrylic ester monomer or allylic monomers, as glycidyl acrylate, glycidyl methacrylate or glycidyl allyl ether etc.
Prepare this monomer that contains the flexible polymer of epoxide group and also can comprise other monomer that can carry out radical polymerization, as vinylbenzene, vinyl acetate, vinyl ether etc.
Prepare this monomer that contains the flexible polymer of epoxide group and also can comprise hydroxyl class monomer, as Hydroxyethyl acrylate, hydroxyethyl methylacrylate, Propylene glycol monoacrylate, Rocryl 410, vinylformic acid hydroxy butyl ester.
General solution polymerization process can be implemented the preparation of flexible polymer of the present invention.
The more excellent consumption of described Resins, epoxy is 30-60 part quality, contains two or more epoxide groups on each Resins, epoxy molecule.
The more suitable epoxy equivalent (weight) of Resins, epoxy of the present invention is 50-5000g/mol, is preferred with 200-2000g/mol, and wherein the Resins, epoxy of softening temperature between 10-100 ℃ accounts for more than 60%.Common various Resins, epoxy all can be used for body series, for example:
The Racemic glycidol ether type epoxy: comprise the glycidyl ether of various phenol, these phenol structures comprise dihydroxyphenyl propane, Bisphenol F, bisphenol S and line style phenolic aldehyde etc.; The glycidyl ether of aliphatics alcohols;
Glycidyl ester type epoxy resin: as the phthalic acid 2-glycidyl ester, dimeracid 2-glycidyl ester etc.;
Glycidyl amine type epoxy resin: as diaminodiphenylmethane four glycidyl amines, triglycidyl group chlorinated isocyanurates etc.;
Cycloaliphatic epoxides: as the titanium dioxide dipentadiene, titanium dioxide dicyclo amyl ether etc.;
Line style aliphatic epoxide: as polyhutadiene epoxide etc.;
Serve as preferred wherein with bisphenol A-type and line style phenolic structure type;
Can be used alone and also can piece together with several different above-mentioned Resins, epoxy.
Described reactive thinner is the compound that contains 1 or 1 above epoxide group in the molecular structure, and its epoxy equivalent (weight) is 50-400g/mol, wherein is preferred with 100-250g/mol, and its consumption serves as preferred with 2-10 part quality; The typical reactive thinner that can be used for body series comprises: phenyl glycidyl ether, n-butyl glycidyl ether, glycidyl allyl ether, glycidyl methacrylate, diglycidylether, butanediol diglycidyl ether, glycerol triglycidyl ether etc.
Latent curing agent is selected the latent curing agent of thermal activation for use, for example one or more mixtures in Dyhard RU 100, hydrazides, the imidazoles.The preferred 1-10 part of its consumption quality.
According to performance need, the present invention also can comprise other resins, linking agent, softening agent, tackifying resin, filler, pigment, stablizer, curing reaction catalyst, tenderizer and solvent etc.
When tackiness agent of the present invention is used to prepare the adhesive sheet that contains high-adhesive-strength structure pressure sensitive adhesive, can select paper, plastic film and various fabrics etc. as base material, with being coated with or being compound in the two sides of base material after each component mixing of structural pressure-sensitive adhesive of the present invention, make the structure pressure sensitive adhesion sheet.
Also can with adhesive coated of the present invention on separate paper, make the structure pressure sensitive adhesion sheet of no base material.Described plastic film comprises polyester, nylon and polyimide etc., and described fabric material comprises glass fibre, carbon fiber and various plastic optical fibres etc.
The present invention compared with prior art has following advantage:
1, the present invention has been owing to used reactive thinner, overcome the contradiction between the pressure-sensitive and shearing resistance in the prior art, has good pressure-sensitive before can obtaining being heating and curing, and the structural pressure-sensitive adhesive that has higher shear intensity after being heating and curing.
2, compare with the technology that distant pawl of disclosed employing or heterotelechelic polymers prepare structural pressure-sensitive adhesive, need not double bond containing material in the system of the present invention, overcome the former easy aged problem; The present invention adopts the method for radical polymerization more convenient more feasible than the former anionic polymerisation process, has reduced manufacturing cost simultaneously.
3, among the present invention by selection to the structure and the characteristic of Resins, epoxy, compare with the curable pressure sensitive adhesive technology of disclosed polyacrylic ester/Resins, epoxy, can increase the consumption of Resins, epoxy, thereby obtain higher shearing resistance, kept good forming process simultaneously, the structure pressure sensitive adhesion sheet of preparation can cut randomly, the convenient use.
4, contain the acrylic polymers/Resins, epoxy of carboxylic acid and the curable pressure sensitive adhesive technology of usefulness is compared with disclosed, the present invention selects the latent curing agent of thermal activation for use, and the package stability of products therefrom is better, and shearing resistance is higher.
Specific embodiments
The detection of in embodiment and comparing embodiment, carrying out, its method is as follows:
1) 180 ° of stripping strengths
Base material is the polyester film of thickness 25 μ m, and dried glue thickness is 30 μ m, presses GB 2792-81 test.
2) initial cohesiveness
Press GB 4852-84 test.
3) lap shear strength (normal temperature):
Test piece is with duralumin (Al), and its treatment process is, polishes in water with sand paper and dries after the cleaning.Condition of cure: 180 ℃ * 1.5hr, pressure, 500g.Test draw speed: 5mm/min.
4) lap shear strength (being heated):
The pulling experiment machine of constant temperature oven is equipped with in employing, is incubated 30min after being warmed up to design temperature, tests again, and all the other conditions are with 3).
Embodiment 1
Contain the preparation of epoxide group flexible polymer
In the four-hole boiling flask that condenser, nitrogen inlet and agitator are housed, add 85 parts of butyl acrylates, 39 parts of ethyl propenoates, 20 parts of methyl methacrylates, 4 parts of Hydroxyethyl acrylates and 22 parts of glycidyl methacrylate, 200 parts of vinyl acetic monomers, with 0.15 part of benzoyl peroxide as initiator, 75 ℃ of following polyreactions 6 hours, transformation efficiency is 98%, obtains containing the polymeric constituent of epoxide group.The epoxy equivalent (weight) of this polymkeric substance is 1096g/mol.As calculated, the second-order transition temperature of this polymkeric substance is-24.2 ℃.
Embodiment 2
Contain the preparation of epoxide group flexible polymer
Monomer component among the above-mentioned preparation embodiment 1 is changed into, 94 parts of butyl acrylates, 50 parts of Isooctyl acrylate monomers, 4 parts of Hydroxyethyl acrylates and 22 parts of glycidyl methacrylate, all the other components and condition are constant.The transformation efficiency of polymerisate is 99%.The epoxy equivalent (weight) of this polymkeric substance is 1015g/mol.As calculated, the second-order transition temperature of this polymkeric substance is-49.6 ℃.
Embodiment 3
Calculate with solid part, contain the epoxide group flexible polymer with what make in 50 parts " the preparation embodiment 1 that contains the epoxide group flexible polymer ", (softening temperature is 65 ℃ to 40 parts of epoxy phenolicss, epoxy equivalent (weight) is 238g/mol), 10 parts of bisphenol A type epoxy resins (model is E-51), 6 parts of Dyhard RU 100s, 1 part of vinyl acetic monomer solution that contains the affixture 50% (wt) of TriMethylolPropane(TMP) and tolylene diisocyanate, mix with 40 parts of methylethylketones, and be uniformly dispersed, make the solution of structure pressure sensitive adhesive.
With this solution coat on the polyester film of thickness 25 μ m, and 110 ℃ dry 10 minutes down, making bondline thickness is the structure pressure sensitive film of 30 μ m.180 ° of stripping strengths of this film are 2.1N/25mm, and initial bonding strength can not surveyed the result, and (promptly use GB 4852-84 testing method, initial bonding strength does not reach 1 of minimum
#Steel ball).
With the solution coat of structure pressure sensitive adhesive on separate paper, through 110 ℃ dry 10 minutes down, drying adhesive layer thickness be the no base material type structure pressure sensitive film of 80 μ m, its normal temperature shearing resistance is 18.7MPa after testing.100 ℃ shearing resistances is 11.2MPa.
Embodiment 4
Structural pressure-sensitive adhesive is made up of the component of following mass fraction:
The flexible polymer that contains epoxide group 20 of embodiment 1 preparation
Phthalic acid 2-glycidyl ester 80
Phenyl glycidyl ether 0.5
Dyhard RU 100 0.1
Embodiment 5
Structural pressure-sensitive adhesive is made up of the component of following mass fraction:
The flexible polymer that contains epoxide group 80 of embodiment 2 preparations
The glycidyl ether 10 of line style phenolic aldehyde
Phthalic acid 2-glycidyl ester 10
N-butyl glycidyl ether 20
Hydrazides 10
Imidazoles 10
Embodiment 6
Structural pressure-sensitive adhesive is made up of the component of following mass fraction:
The flexible polymer that contains epoxide group 50 of embodiment 1 preparation
Phthalic acid 2-glycidyl ester 10
Dimeracid 2-glycidyl ester 10
Diaminodiphenylmethane four glycidyl amines 10
Triglycidyl group chlorinated isocyanurates 20
Glycidyl allyl ether 10
Dyhard RU 100 4
Hydrazides 3
Imidazoles 3
The comparative example 1
That adopts embodiment 2 preparations contains the epoxide group flexible polymer, and other is formed and preparation condition same " embodiment 3 ".180 ° of stripping strengths of made film are 6.7N/25mm, and initial bonding strength is 5
#Steel ball.
With the solution coat of structure pressure sensitive adhesive on separate paper, through 110 ℃ dry 10 minutes down, drying adhesive layer thickness be the no base material type structure pressure sensitive film of 80 μ m, its shearing resistance is 3.3MPa after testing.100 ℃ shearing resistances is 0.6MPa.
The comparative example 2
In the structure pressure sensitive adhesive solution of " embodiment 3 ", other adds 4 parts of butanediol diglycidyl ethers (epoxy equivalent (weight) is 155g/eq), and other composition and preparation condition are with " embodiment 3 ".180 ° of stripping strengths of made film are 7.5N/25mm, and initial bonding strength is the 11# steel ball.
With the solution coat of structure pressure sensitive adhesive on separate paper, through 110 ℃ dry 10 minutes down, drying adhesive layer thickness be the no base material type structure pressure sensitive film of 80 μ m, its shearing resistance is 17.4MPa after testing.
This structure pressure sensitive adhesive was at room temperature placed 6 months, and recording 180 ° of stripping strengths is 6.8N/25mm, and initial bonding strength is 10
#Steel ball, shearing resistance are 16.4MPa.
The comparative example 3
With the used product that the epoxide group flexible polymer changes embodiment 2 into, other composition and the preparation condition same " comparative example 2 " of containing in " comparative example 2 ".180 ° of stripping strengths of made film are 9.3N/25mm, and initial bonding strength is 15
#Steel ball.
With the solution coat of structure pressure sensitive adhesive on separate paper, through 110 ℃ dry 10 minutes down, drying adhesive layer thickness be the no base material type structure pressure sensitive film of 80 μ m, its shearing resistance is 2.7MPa after testing.
The comparative example 4
Used Resins, epoxy in the structure pressure sensitive adhesive solution of " embodiment 3 " is changed into, 50 parts of bisphenol A type epoxy resins (model is E-51), all the other compositions and preparation condition are with " comparative example 3 ".180 ° of stripping strengths of made film are 0.6N/25mm, and initial bonding strength is 7
#Steel ball.
With the solution coat of structure pressure sensitive adhesive on separate paper, through 110 ℃ dry 10 minutes down, drying adhesive layer thickness be the no base material type structure pressure sensitive film of 80 μ m, its shearing resistance is 15.8MPa after testing.
The comparative example 5
With the structure pressure sensitive adhesive solution coat of " comparative example 2 " on separate paper, drying is 10 minutes under 110 ℃, getting drying adhesive layer thickness is the structure pressure-sensitive adhesive layer of 60 μ m, this glue-line is compound in the two sides of glasscloth, obtaining with the glasscloth is the structure pressure sensitive film of base material, and its shearing resistance is 19.8MPa after testing.
Sum up the foregoing description and comparative example, can draw:
Contrast the foregoing description 3 and comparative example 1, the employing second-order transition temperature is-24.2 ℃ the pressure sensitive adhesive that contains the preparation of epoxide group flexible polymer, its shearing resistance is 18.7MPa, and is-49.6 ℃ pressure sensitive adhesive with second-order transition temperature, and its shearing resistance only is 3.3MPa.This result shows the former the used second-order transition temperature that contains the epoxide group flexible polymer (40-0 ℃) in preferable range, and the gained pressure sensitive adhesive has higher shearing resistance, presents the characteristic of sqtructural adhesive.But embodiment 3 and comparative example's 1 result has presented the contradiction between pressure-sensitive and the shearing resistance, and promptly pressure-sensitive (initial bonding strength and stripping strength) is good, and then shearing resistance is poor, otherwise then shearing resistance is good.
Comparative example 2 has added reactive thinner in embodiment 3, Zhi Bei structural pressure-sensitive adhesive has not only kept the higher shear intensity of embodiment 3 products thus, and have good pressure-sensitive, solved the contradiction between pressure-sensitive and the shearing resistance preferably.
The Resins, epoxy E-51 that comparative example 4 is used, its softening temperature be less than 0 ℃, not in the preferred 10-100 of the present invention ℃ scope, and when preparing adhesive sheet with this tackiness agent, insufficient formability, the pressure-sensitive of products therefrom is poor.
Claims (8)
1, a kind of structural pressure-sensitive adhesive is characterized in that being made up of the component of following mass fraction:
The flexible polymer 20-80 that contains epoxide group
Resins, epoxy 20-80
Reactive thinner 0.5-20
Latent curing agent 0.1-20
Containing the flexible polymer of epoxide group and the umber sum of Resins, epoxy is 100;
The described flexible polymer that contains epoxide group is made by following at least two kinds of monomer copolymerizations:
(1) acrylic monomer of general formula (I)
CH
2=C(R
1)COOR
2 (I)
R in the formula
1Represent hydrogen atom or methyl; R
2Represent the alkyl of 2-14 carbon atom;
(2) contain in the acrylic ester monomer, methyl acrylic ester monomer, allylic monomers of epoxide group and two keys one or more;
Described reactive thinner is phenyl glycidyl ether, n-butyl glycidyl ether, glycidyl allyl ether, glycidyl methacrylate, diglycidylether, butanediol diglycidyl ether or glycerol triglycidyl ether, and its epoxy equivalent (weight) is 50-400g/mol;
Described latent curing agent is selected one or more mixtures in Dyhard RU 100, hydrazides, the imidazoles for use.
2, structural pressure-sensitive adhesive according to claim 1 is characterized in that monomer in described (2) is one or more in glycidyl acrylate, glycidyl methacrylate, the glycidyl allyl ether.
3, structural pressure-sensitive adhesive according to claim 1 and 2 is characterized in that the described consumption that contains the flexible polymer of epoxide group is 40-70 part quality; Its epoxy equivalent (weight) is 300-10000g/mol, second-order transition temperature (T
g) be-70-20 ℃.
4, structural pressure-sensitive adhesive according to claim 3, the monomer that it is characterized in that preparing the flexible polymer that contains epoxide group also comprise one or more in the vinylbenzene that can carry out radical polymerization, vinyl acetate, the vinyl ether.
5, structural pressure-sensitive adhesive according to claim 3, the monomer that it is characterized in that preparing the flexible polymer that contains epoxide group also comprises one or more in hydroxyl class monomer Hydroxyethyl acrylate, hydroxyethyl methylacrylate, Propylene glycol monoacrylate, Rocryl 410, the vinylformic acid hydroxy butyl ester.
6, structural pressure-sensitive adhesive according to claim 3, the consumption that it is characterized in that described Resins, epoxy is 30-60 part quality, contain two or more epoxide groups on each Resins, epoxy molecule, epoxy equivalent (weight) is 50-5000g/mol, and wherein the Resins, epoxy of softening temperature between 10-100 ℃ accounts for more than 60%.
7, structural pressure-sensitive adhesive according to claim 6 is characterized in that described Resins, epoxy comprises: one or more in Racemic glycidol ether type epoxy, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, cycloaliphatic epoxides, the line style aliphatic epoxide.
8, structural pressure-sensitive adhesive according to claim 6, it is characterized in that described Resins, epoxy comprises: the glycidyl ether of dihydroxyphenyl propane, Bisphenol F, bisphenol S or line style phenolic aldehyde, the phthalic acid 2-glycidyl ester, the dimeracid 2-glycidyl ester, diaminodiphenylmethane four glycidyl amines, triglycidyl group chlorinated isocyanurates, titanium dioxide dipentadiene, titanium dioxide dicyclo amyl ether, one or more in the polyhutadiene epoxide.
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CN103848799A (en) * | 2014-01-16 | 2014-06-11 | 常州大学 | Method of preparing mixed diglycidyl phthalate by using PTA (Purified Terephthalic Acid) residue |
CN103848799B (en) * | 2014-01-16 | 2016-04-13 | 常州大学 | A kind of PTA of utilization residue prepares the method for pure mixed phthalic acid 2-glycidyl ester |
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CN110527454A (en) * | 2019-08-20 | 2019-12-03 | 常州都铂高分子有限公司 | A kind of novel high temperature resistant peelable type pressure sensitive adhesive tape |
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