CN115746756A - High-temperature-resistant acrylate pressure-sensitive adhesive and preparation method of acrylate pressure-sensitive adhesive - Google Patents
High-temperature-resistant acrylate pressure-sensitive adhesive and preparation method of acrylate pressure-sensitive adhesive Download PDFInfo
- Publication number
- CN115746756A CN115746756A CN202211335165.5A CN202211335165A CN115746756A CN 115746756 A CN115746756 A CN 115746756A CN 202211335165 A CN202211335165 A CN 202211335165A CN 115746756 A CN115746756 A CN 115746756A
- Authority
- CN
- China
- Prior art keywords
- monomer
- sensitive adhesive
- resistant
- temperature
- 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.)
- Granted
Links
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 63
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000000178 monomer Substances 0.000 claims abstract description 108
- 239000003999 initiator Substances 0.000 claims abstract description 48
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 28
- 229920005610 lignin Polymers 0.000 claims abstract description 25
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims abstract description 24
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 19
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 12
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 10
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical group CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 claims description 10
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 8
- 238000004321 preservation Methods 0.000 claims description 7
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 5
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- 230000032050 esterification Effects 0.000 abstract description 15
- 238000005886 esterification reaction Methods 0.000 abstract description 15
- 238000004132 cross linking Methods 0.000 abstract description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 229910001220 stainless steel Inorganic materials 0.000 description 11
- 239000010935 stainless steel Substances 0.000 description 11
- 239000002390 adhesive tape Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 239000000084 colloidal system Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229920005551 calcium lignosulfonate Polymers 0.000 description 3
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 2
- 241000825895 Argyrops bleekeri Species 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000013043 chemical agent Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229910000833 kovar Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a high-temperature-resistant acrylate pressure-sensitive adhesive liquid which mainly comprises a polymerization main body, an initiator and a solvent, wherein the polymerization main body comprises a soft monomer, a hard monomer, a modified monomer and a heat-resistant monomer, the heat-resistant monomer accounts for 3-6% of the total mass of the polymerization main body, and the heat-resistant monomer comprises esterified modified lignin and ethylene glycol dimethacrylate. The high-temperature-resistant acrylate pressure-sensitive adhesive liquid comprises a heat-resistant monomer, wherein the heat-resistant monomer is used as a part of a polymerization main body, and the density of network crosslinking among polymerization monomers is controlled through the polymerization reaction of esterification modified lignin and ethylene glycol dimethacrylate with other polymerization monomers, so that the high-temperature resistance and the cohesion stability of the pressure-sensitive adhesive are improved.
Description
Technical Field
The invention relates to the technical field of pressure-sensitive adhesives, in particular to a high-temperature-resistant acrylate pressure-sensitive adhesive solution and a preparation method of the acrylate pressure-sensitive adhesive.
Background
With the rapid development of communication and electronic industries, the production of high frequency inductors is driven, and therefore, the carrier film, which is an auxiliary material in the processing process of the high frequency inductors, is increased. Wherein, 5G high frequency inductor processing is through high temperature treatment and processing condition require highly, and the performance requirement that uses the carrier membrane in the production process also increases thereupon. The carrier membrane according to the processing technology requirement of the high-frequency inductor is a high-thickness membrane, and simultaneously meets the requirement of excellent high-temperature stability in the high-temperature processing process. The stability includes non-delamination between the laminated structures, the dimensional stability of the film body and the maintenance of the functionality of each layer, especially the high temperature resistance of the adhesive layer, so that the stability of the carrier film in the whole processing process can be ensured and the dimensional stability of the carrier film can be further maintained.
Disclosure of Invention
One of the purposes of the invention is to overcome the defects in the prior art and provide a high-temperature-resistant acrylate pressure-sensitive adhesive solution, wherein the high-temperature resistance of the pressure-sensitive adhesive is improved by esterifying and modifying a heat-resistant monomer compounded by lignin and ethylene glycol dimethacrylate.
In order to realize the process effect, the technical scheme of the invention is as follows: the high-temperature-resistant acrylate pressure-sensitive adhesive liquid mainly comprises a polymerization main body, an initiator and a solvent, wherein the polymerization main body comprises a soft monomer, a hard monomer, a modified monomer and a heat-resistant monomer, the heat-resistant monomer accounts for 3-6% of the total mass of the polymerization main body, and the heat-resistant monomer comprises esterified modified lignin and ethylene glycol dimethacrylate.
The preferable technical scheme is as follows: the mass ratio of the esterification modified lignin to the ethylene glycol dimethacrylate is (0.2 to 0.6) to 1.
The preferable technical scheme is as follows: the mass ratio of the soft monomer to the hard monomer to the modified monomer is (16 to 30): 1: (1.2 to 4).
The preferable technical scheme is as follows: according to the mass parts, the pressure sensitive adhesive solution comprises 70 to 85 parts of soft monomer, 3~5 parts of hard monomer, 6 to 11 parts of modified monomer, 3~5 parts of heat-resistant monomer, 0.65 to 0.9 part of initiator and 110 to 180 parts of solvent.
The preferable technical scheme is as follows: the soft monomer is iso-octyl acrylate and/or butyl acrylate; the hard monomer is methyl methacrylate; the modified monomer is acrylic acid and hydroxyethyl acrylate.
The preferable technical scheme is as follows: the initiator is azobisisobutyronitrile and/or benzoyl peroxide.
The preferable technical scheme is as follows: the solvent is ethyl acetate.
The invention also aims to overcome the defects in the prior art and provide a preparation method of the acrylate pressure-sensitive adhesive, which comprises the following steps:
s1: mixing the polymerization main body in the high-temperature-resistant acrylate pressure-sensitive adhesive solution, and dividing the initiator into a first part of initiator and a second part of initiator;
s2: heating the solvent;
s3: dropwise adding the mixed polymerization main body of the S1, adding a first part of initiator, heating to be stable in a first section, and carrying out heat preservation reaction;
s4: and in the second stage, heating to be stable, adding a second part of initiator, and carrying out heat preservation reaction to obtain the acrylate pressure-sensitive adhesive.
The preferable technical scheme is as follows: the temperature of the first section is increased to 70-75 ℃, and the temperature of the second section is increased to 77-85 ℃.
The preferable technical scheme is as follows: the mass of the first part of initiator accounts for 4-10% of the total mass of the initiator.
The invention has the advantages and beneficial effects that:
the high-temperature-resistant acrylate pressure-sensitive adhesive liquid comprises a heat-resistant monomer, wherein the heat-resistant monomer is used as a part of a polymerization main body, and the density of network crosslinking among polymerization monomers is controlled through the polymerization reaction of esterification modified lignin and ethylene glycol dimethacrylate with other polymerization monomers, so that the high-temperature resistance and the cohesion stability of the pressure-sensitive adhesive are improved.
Detailed Description
The following further describes embodiments of the present invention with reference to examples. The following examples are only for illustrating the technical solutions of the present invention more clearly, and the protection scope of the present invention is not limited thereby.
Raw materials
Ethylene glycol dimethacrylate was produced by Guangzhou double bond chemical trade company;
isooctyl acrylate is manufactured by Shanghai friendship corporation;
butyl acrylate is manufactured by Shanghai friendship corporation;
methyl methacrylate is produced by taiwan tai plastic group of china;
acrylic acid is produced by taiwan tai plastic group;
hydroxyethyl acrylate was produced by LG group corporation of Korea;
azobisisobutyronitrile was produced by Jiangsu Kovar corporation;
benzoyl peroxide was produced by Jiangsu Kovar chemical Co., ltd;
calcium lignosulfonate, mclin chemical agents (96%, weight average molecular weight 528.61 g/mol);
acryloyl Chloride (AC), 96%, mclin chemical agents;
n, N-dimethylacetamide (DMAc), absolute ethyl alcohol, triethylamine (TEA), analytically pure, chemical reagents of the national drug group, inc.
Preparing esterification modified lignin:
in an ice-water bath, dissolving 10g of calcium lignosulfonate in a N, N-dimethylacetamide (DMAc) solution, fully stirring until the solution is uniform, adding 14g of Triethylamine (TEA) in an inert gas atmosphere, slowly adding an esterification reagent Acryloyl Chloride (AC), wherein the dropping time is 1h, the mass ratio of the calcium lignosulfonate to the acryloyl chloride is 1.3, heating after the dropping is finished, and the reaction temperature is 62 ℃ and the reaction time is 6h. And filtering the reaction product, precipitating in ethanol, centrifuging, washing, transferring to a 50 ℃ oven, and drying to constant weight for later use.
Polymeric host
The soft monomer is also called as a viscous monomer and is a main monomer for preparing the pressure-sensitive adhesive, and the soft monomer is mainly alkyl acrylate with 4 to 12 carbon atoms. Has the advantages of low glass transition temperature and good initial viscosity. Soft monomers include, but are not limited to, ethyl acrylate, butyl acrylate, and isooctyl acrylate. Further, the soft monomer is isooctyl acrylate, or a combination of isooctyl acrylate and butyl acrylate. Furthermore, the mass ratio of the isooctyl acrylate to the butyl acrylate is 1: (0.8 to 1.1).
Hard monomers, also referred to as cohesive monomers, are primarily acrylates or other ethylenic monomers. The effect is to produce homopolymers with higher glass transition temperatures and to copolymerize soft monomers. Hard monomers include, but are not limited to, methyl acrylate, methyl methacrylate, vinyl acetate, and styrene. Further, the hard monomer is methyl methacrylate.
The modifying monomer is also called crosslinking monomer or functional monomer, and refers to alkene monomer which has various reactive functional groups and can be copolymerized with soft monomer and hard monomer. Modifying monomers include, but are not limited to, acrylic acid, methacrylic acid, hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, acrylamide, methacrylamide, maleic acid, and maleic anhydride. Further, the modified monomer is acrylic acid and hydroxyethyl acrylate. Further, the mass ratio of acrylic acid to hydroxyethyl acrylate is (1~3): 1. further, the mass ratio of acrylic acid to hydroxyethyl acrylate is (1.5 to 3): 1.
n-vinylpyrrolidone (NVP), 4-Acryloylmorpholine (ACMO), ethylene Glycol Dimethacrylate (EGDMA) and trimethylolpropane triacrylate (TMPTA) are frequently used as heat-resistant monomers. The heat-resistant monomer accounts for the total mass of the main polymerization body, the monomer has too large polymerization molecular weight and too large crosslinking density, and further the pressure-sensitive adhesive is colloidal gel; too little pressure sensitive adhesive colloid has poor temperature resistance and can not meet the requirements of high temperature resistance and reduced permanent viscosity.
Solvent(s)
In the synthesis process of the acrylate pressure-sensitive adhesive, the solvent has an induction effect in the free radical decomposition process, so that the molecular weight of the polymer is influenced, and the bonding performance of the pressure-sensitive adhesive is further influenced. Further, the solvent is ethyl acetate.
Heat-resistant monomer
Further, the heat-resistant monomer is esterification modified lignin and ethylene glycol dimethacrylate. The amount of linear polymerization macromolecules of the ethylene glycol dimethacrylate and the esterification modified lignin is increased in the initial reaction stage, so that the heat resistance and the weather resistance of the pressure-sensitive adhesive are improved, the polymerization molecular weight is increased, the network crosslinking density is controlled, the cohesion stability and the sustained viscosity are ensured, and the high temperature resistance is better. The addition of the esterified modified lignin can improve the thermal stability of the polymeric substance. The consumption of the esterification modified lignin is too small, the molecular crosslinking is insufficient, the high temperature resistance at the temperature of more than 150 ℃ is poor, and the viscosity retention of the pressure-sensitive adhesive colloid is reduced; the consumption of the esterification modified lignin is too large, the reaction viscosity is increased too fast and is not easy to control, and the crosslinking density is too large, thereby having negative influence on the comprehensive performance of the pressure-sensitive adhesive colloid. The mass ratio of the esterification modified lignin to the ethylene glycol dimethacrylate is (0.2 to 0.6): 1. further, the mass ratio of the esterification modified lignin to the ethylene glycol dimethacrylate is (0.25 to 0.5): 1.
initiator
The use amount of the pressure-sensitive adhesive is too much, so that the molecular weight of the pressure-sensitive adhesive colloid is small, and the adhesive property is reduced; if too little, the reaction time is prolonged, the conversion rate of the monomers is low, and the residue is high. Further, the initiator is azobisisobutyronitrile and/or benzoyl peroxide. Further, the initiator is azobisisobutyronitrile.
Preparation method of acrylate pressure-sensitive adhesive
S1: mixing a soft monomer, a hard monomer, a modified monomer and a heat-resistant monomer in the pressure-sensitive adhesive solution, and dividing an initiator into a first initiator and a second initiator, wherein the mass of the first initiator accounts for 4-10% of the total mass of the initiators;
s2: heating a solvent ethyl acetate to the initial temperature of room temperature, and heating to 40-45 ℃;
s3: dropwise adding the mixed polymerization main body of the S1, adding a first part of initiator, heating to a stable temperature in a first period, heating to 70-75 ℃ in the first period, wherein the heating time is 0.5-1h, and carrying out heat preservation reaction for 2-2.5 h;
s4: and (3) heating to be stable in the second period, heating to be 77-85 ℃ in the second period, heating for 20-25min, adding a second initiator for 40-60min, and carrying out heat preservation reaction for 1.5-2h to obtain the acrylate pressure-sensitive adhesive.
Example 1
According to the mass portion, the main components of the high-temperature resistant acrylate pressure-sensitive adhesive solution are 82 parts of soft monomer, 4 parts of hard monomer, 10 parts of modified monomer, 4 parts of heat-resistant monomer, 0.75 part of initiator and 160 parts of solvent. The solvent is ethyl acetate, and the initiator is azobisisobutyronitrile.
The heat-resistant monomer is esterification modified lignin and ethylene glycol dimethacrylate. The mass ratio of the esterification modified lignin to the ethylene glycol dimethacrylate is 0.4:1.
the soft monomer is isooctyl acrylate and butyl acrylate, and the mass ratio of the isooctyl acrylate to the butyl acrylate is 1:1; the hard monomer is methyl methacrylate; the modified monomer is acrylic acid and hydroxyethyl acrylate, and the mass ratio of the acrylic acid to the hydroxyethyl acrylate is 1.8:1.
the preparation method of the acrylate pressure-sensitive adhesive comprises the following steps:
s1: mixing a soft monomer, a hard monomer, a modified monomer and a heat-resistant monomer according to a ratio, and dividing an initiator into a first initiator and a second initiator, wherein the mass of the first initiator accounts for 8% of the total mass of the initiator;
s2: heating the solvent ethyl acetate to 40 ℃ with the initial temperature of room temperature;
s3: dropwise adding the mixed polymerization main body of the S1, adding a first part of initiator, heating the first section to be stable, heating the first section to 72 ℃, keeping the temperature for reaction for 1h, and keeping the temperature for reaction for 2h;
s4: and (3) heating to be stable in the second stage, heating to 80 ℃ in the second stage, heating for 20min, adding a second part of initiator, dropwise adding the second part of initiator for 55min, and carrying out heat preservation reaction for 2h to obtain the acrylate pressure-sensitive adhesive.
Example 2
Example 2 is based on example 1, except that the mass ratio of the esterified modified lignin to the ethylene glycol dimethacrylate is unchanged, and the high-temperature resistant acrylate pressure sensitive adhesive solution mainly comprises 82 parts by mass of a soft monomer, 4 parts by mass of a hard monomer, 10 parts by mass of a modified monomer, 5 parts by mass of a heat resistant monomer, 0.75 part by mass of an initiator and 160 parts by mass of a solvent. The heat-resistant monomer accounts for 5% of the total mass of the main polymer. The process conditions were unchanged.
Example 3
Example 3 is based on example 1, except that the mass ratio of the esterified modified lignin to the ethylene glycol dimethacrylate is unchanged, and the high-temperature resistant acrylate pressure sensitive adhesive solution mainly comprises 75 parts by mass of a soft monomer, 3 parts by mass of a hard monomer, 9 parts by mass of a modified monomer, 5 parts by mass of a heat-resistant monomer, 0.75 part by mass of an initiator and 160 parts by mass of a solvent. The heat-resistant monomer accounts for 5.4% of the total mass of the main polymer. The process conditions were unchanged.
Example 4
Example 4 is based on example 1, with the difference that the main components of the high temperature resistant acrylate pressure sensitive adhesive solution are unchanged, and the mass ratio of the esterified modified lignin to the ethylene glycol dimethacrylate is 0.2:1. the process conditions were unchanged.
Example 5
Example 5 is based on example 1, with the difference that the main components of the high temperature resistant acrylate pressure sensitive adhesive solution are unchanged, and the mass ratio of the esterified modified lignin to the ethylene glycol dimethacrylate is 0.55:1. the process conditions were unchanged.
Example 6
Example 6 is based on example 2, except that the main components of the high temperature resistant acrylate pressure sensitive adhesive solution are unchanged, and the mass ratio of the esterified modified lignin to the ethylene glycol dimethacrylate is 0.3:1. the process conditions were unchanged.
Example 7
Example 7 is based on example 1 with the difference that the components are unchanged, the parts of the components added are unchanged, and the mass ratio of acrylic acid to hydroxyethyl acrylate in the modified monomer is 1:1. the process conditions were unchanged.
Example 8
Example 8 is based on example 1 except that the soft monomer is isooctyl acrylate and no portion of the added component is changed. The process conditions were unchanged.
Example 9
Example 9 is based on example 1 with the difference that the initiator is benzoyl peroxide. The process conditions were unchanged.
Example 10
Example 10 is based on example 1, except that the composition of the pressure-sensitive adhesive solution is unchanged, the first stage of temperature rise is not set, the mixed polymerization main body of S1 is added dropwise, the first part of initiator is added, the temperature is raised to 80 ℃, the temperature rise time is 1h, after the temperature is stabilized, the second part of initiator is added, the dropwise adding time of the second part of initiator is 55min, and the temperature is kept for 2h, so that the acrylate pressure-sensitive adhesive is prepared.
Example 11
Example 11 is based on example 1 with the difference that the first stage is warmed to 65 ℃ and the other process conditions are unchanged.
Example 12
Example 12 is based on example 1 with the difference that the second stage is warmed to 75 ℃ and the other process conditions are unchanged.
Comparative example 1
Comparative example 1 is based on example 1 with the difference that the heat resistant monomer is only an esterification modified lignin. The parts of all the components added into the pressure-sensitive adhesive solution are unchanged, and the process conditions are unchanged.
Comparative example 2
Comparative example 2 is based on example 1 with the difference that the heat-resistant monomer is only ethylene glycol dimethacrylate. The parts of the components added into the pressure-sensitive adhesive solution are unchanged, and the process conditions are unchanged.
Comparative example 3
Comparative example 3 is based on example 1, except that the high temperature resistant acrylate pressure sensitive adhesive solution mainly comprises, by mass, 70 parts of a soft monomer, 3 parts of a hard monomer, 10 parts of a modified monomer, 5.5 parts of a heat resistant monomer, 0.75 part of an initiator, and 160 parts of a solvent. The heat-resistant monomer accounts for 6.2% of the total mass of the main polymer. The mass ratio of the esterification modified lignin to the ethylene glycol dimethacrylate is unchanged.
Performance testing
(1) Peel strength: according to the standard GB/T2792-2014, a standard adhesive tape (25mm. About.200mm) is attached to a stainless steel plate wiped clean by alcohol, back-pressed by a press roll of 2kg, placed at room temperature for a period of time, tested by a peel force tester, measured for more than three times, and averaged.
(2) Permanent adhesion: according to the standard GB/T4851-2014, a standard adhesive tape (25 mm in width and 100mm in length) is attached to a stainless steel plate, the upper end of the standard adhesive tape is aligned with a standard line, the redundant part at the lower end of the standard adhesive tape is cut off, the stainless steel plate is placed at 150 ℃ for 30min after being subjected to back pressing for three times by a 2kg pressing roller, the stainless steel plate attached with a sample is vertically hung on a test frame and kept in a static state, a weight of 200g is hung below the test frame, and the time for which the adhesive tape falls represents the magnitude of the pressure-sensitive adhesive holding power. The same procedure was used to determine the tack strength after 30min at 180 ℃.
(3) High temperature resistance: wiping a stainless steel plate, uniformly sticking a pressure-sensitive adhesive sample with the specification of 25mm x 100mm on the stainless steel plate, putting the stainless steel plate into an oven, baking the stainless steel plate for 30min at the temperature of 150 ℃, taking out the stainless steel plate, cooling the stainless steel plate to room temperature, slowly stripping off an adhesive tape, observing the surface condition of the stainless steel plate, and mainly observing the deformation condition and the adhesive residue condition of the adhesive tape. The same method was used to test the tape for changes at 180 ℃.
The method for grading the residual glue condition comprises the following steps: the grades are classified into A, B, C, D four grades, grade a: no residue is left; b stage: the ratio of the residual area to the total area of the pressure-sensitive adhesive sample is 1% -5%; the ratio of the C-grade residual area to the total area of the pressure-sensitive adhesive sample is 6-30%; d stage: the ratio of the residual area to the total area of the pressure-sensitive adhesive sample is more than 31 percent.
The results of the performance tests of the examples and comparative examples are as follows:
the optimal performance satisfies: the 180 DEG peeling force is 220 to 280 g/25mm; the permanent viscous force at 150 ℃ is more than or equal to 62h, and the permanent viscous force at 180 ℃ is more than or equal to 55h; high temperature resistance, both of A grade at 150 ℃ and 180 ℃.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the technical principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (10)
1. The high-temperature-resistant acrylate pressure-sensitive adhesive liquid is characterized by mainly comprising a polymerization main body, an initiator and a solvent, wherein the polymerization main body comprises a soft monomer, a hard monomer, a modified monomer and a heat-resistant monomer, the heat-resistant monomer accounts for 3-6% of the total mass of the polymerization main body, and the heat-resistant monomer comprises esterified modified lignin and ethylene glycol dimethacrylate.
2. The high-temperature-resistant acrylate pressure-sensitive adhesive solution as claimed in claim 1, wherein the mass ratio of the esterified modified lignin to the ethylene glycol dimethacrylate is (0.2-0.6): 1.
3. The high-temperature-resistant acrylate pressure-sensitive adhesive solution as claimed in claim 1 or 2, wherein the mass ratio of the soft monomer to the hard monomer to the modified monomer is (16 to 30): 1: (1.2 to 4).
4. The high-temperature-resistant acrylate pressure-sensitive adhesive solution as claimed in claim 1 or 2, wherein the pressure-sensitive adhesive solution comprises, by mass, 70 to 85 parts of soft monomer, 3~5 parts of hard monomer, 6 to 11 parts of modified monomer, 3~5 parts of heat-resistant monomer, 0.65 to 0.9 part of initiator and 110 to 180 parts of solvent.
5. The high-temperature-resistant acrylate pressure-sensitive adhesive solution according to claim 4, wherein the soft monomer is isooctyl acrylate and/or butyl acrylate; the hard monomer is methyl methacrylate; the modified monomer is acrylic acid and hydroxyethyl acrylate.
6. The high-temperature-resistant acrylate pressure-sensitive adhesive solution according to claim 4, wherein the initiator is azobisisobutyronitrile and/or benzoyl peroxide.
7. The high-temperature-resistant acrylate pressure-sensitive adhesive solution according to claim 4, wherein the solvent is ethyl acetate.
8. The preparation method of the acrylate pressure-sensitive adhesive is characterized by comprising the following steps:
s1: mixing the high temperature resistant acrylate pressure sensitive adhesive of any one of claim 1~7 with a polymerization host, dividing the initiator into a first part initiator and a second part initiator;
s2: heating the solvent;
s3: dropwise adding the mixed polymerization main body of the S1, adding a first part of initiator, heating to be stable in a first section, and carrying out heat preservation reaction;
s4: and in the second stage, heating to be stable, adding a second part of initiator, and carrying out heat preservation reaction to obtain the acrylate pressure-sensitive adhesive.
9. The method for preparing the acrylate pressure-sensitive adhesive according to claim 8, wherein the temperature of the first section is raised to 70 to 75 ℃, and the temperature of the second section is raised to 77 to 85 ℃.
10. The method for preparing the acrylate pressure-sensitive adhesive according to claim 8, wherein the mass of the first part of the initiator accounts for 4-10% of the total mass of the initiator.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211335165.5A CN115746756B (en) | 2022-10-28 | 2022-10-28 | High-temperature-resistant acrylic ester pressure-sensitive adhesive liquid and preparation method of acrylic ester pressure-sensitive adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211335165.5A CN115746756B (en) | 2022-10-28 | 2022-10-28 | High-temperature-resistant acrylic ester pressure-sensitive adhesive liquid and preparation method of acrylic ester pressure-sensitive adhesive |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115746756A true CN115746756A (en) | 2023-03-07 |
| CN115746756B CN115746756B (en) | 2024-05-14 |
Family
ID=85355800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211335165.5A Active CN115746756B (en) | 2022-10-28 | 2022-10-28 | High-temperature-resistant acrylic ester pressure-sensitive adhesive liquid and preparation method of acrylic ester pressure-sensitive adhesive |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115746756B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1693342A (en) * | 2005-04-30 | 2005-11-09 | 江苏工业学院 | Process for preparing modified lignocellulose sulfonate graft copolymer |
| US20080033095A1 (en) * | 2006-08-03 | 2008-02-07 | Nitto Denko Corporation | Method for producing aqueous pressure-sensitive adhesive composition |
| CN106590478A (en) * | 2016-12-07 | 2017-04-26 | 哈尔滨工业大学无锡新材料研究院 | High-temperature-resistant solvent-type acrylate pressure-sensitive adhesive and preparation method thereof |
| CN113583600A (en) * | 2021-08-30 | 2021-11-02 | 江苏晶华新材料科技有限公司 | High-temperature-resistant pressure-sensitive adhesive, preparation process and application thereof |
-
2022
- 2022-10-28 CN CN202211335165.5A patent/CN115746756B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1693342A (en) * | 2005-04-30 | 2005-11-09 | 江苏工业学院 | Process for preparing modified lignocellulose sulfonate graft copolymer |
| US20080033095A1 (en) * | 2006-08-03 | 2008-02-07 | Nitto Denko Corporation | Method for producing aqueous pressure-sensitive adhesive composition |
| CN106590478A (en) * | 2016-12-07 | 2017-04-26 | 哈尔滨工业大学无锡新材料研究院 | High-temperature-resistant solvent-type acrylate pressure-sensitive adhesive and preparation method thereof |
| CN113583600A (en) * | 2021-08-30 | 2021-11-02 | 江苏晶华新材料科技有限公司 | High-temperature-resistant pressure-sensitive adhesive, preparation process and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN115746756B (en) | 2024-05-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10414954B2 (en) | Water-based pressure-sensitive adhesive compositions | |
| CN105647087B (en) | Curable compositions, contact adhesive, adhesive tape, adhesive article | |
| US9399724B2 (en) | Pressure-sensitive adhesives with (meth)acrylic-based elastomeric materials prepared using (2-isopropyl-5-methyl)hexyl (meth)acrylate | |
| KR20140016842A (en) | Pressure-sensitive adhesive composition, pressure-sensitive adhesive layer, pressure-sensitive adhesive sheet and optical film | |
| CN102492379A (en) | Fog-resistant aqueous pressure-sensitive adhesive and polyethylene protection film containing same | |
| CA2067969A1 (en) | Method for making structured suspension psa beads | |
| KR101675452B1 (en) | Acrylic emulsion pressure sensitive adhesive agent with good low-temperature resistance and production method thereof | |
| KR20190072421A (en) | Aqueous acrylic adhesive for clothes and method for preparing the same | |
| US10081745B1 (en) | Water-based pressure-sensitive adhesive compositions | |
| KR102671012B1 (en) | Acrylic emulsion pressure sensitive adhesive composition | |
| CN115746756A (en) | High-temperature-resistant acrylate pressure-sensitive adhesive and preparation method of acrylate pressure-sensitive adhesive | |
| JPH0155641B2 (en) | ||
| CN116063960A (en) | Flame-retardant binding material for power battery module and preparation process and application thereof | |
| CN115322705A (en) | Ultrathin high-stripping polyacrylate pressure-sensitive adhesive and preparation method thereof | |
| EP4045546B1 (en) | Method for producing a removable pressure-sensitive adhesive (psa) and pressure-sensitive adhesive thus produced | |
| JP2670055B2 (en) | Pressure sensitive adhesive | |
| KR20090112103A (en) | Method for Preparing Starch-Acryl Copolymer Using Emulsifier-Free Emulsion Polymerization | |
| KR102332742B1 (en) | Acrylic emulsion pressure sensitive adhesive composition | |
| KR100869483B1 (en) | Release Coating and Process | |
| KR20210148722A (en) | Acrylic emulsion pressure snsitive adhesive composition | |
| KR101350515B1 (en) | Acrylic sticky adhesive composition of water dispersion | |
| CN113201286A (en) | High-filling modified polyacrylate optical adhesive composition, OCA pressure-sensitive adhesive tape and preparation method thereof | |
| KR102625863B1 (en) | Acrylic emulsion pressure snsitive adhesive composition | |
| JP4366708B2 (en) | Water-dispersed pressure sensitive adhesive for re-peeling | |
| CN115491153B (en) | Cross-linked aqueous acrylic ester segmented copolymer pressure-sensitive adhesive 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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |