CN116891666A - Removable modified acrylic resin pressure-sensitive adhesive and preparation method thereof - Google Patents
Removable modified acrylic resin pressure-sensitive adhesive and preparation method thereof Download PDFInfo
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- CN116891666A CN116891666A CN202310678257.1A CN202310678257A CN116891666A CN 116891666 A CN116891666 A CN 116891666A CN 202310678257 A CN202310678257 A CN 202310678257A CN 116891666 A CN116891666 A CN 116891666A
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- modified acrylic
- sensitive adhesive
- acrylic resin
- pressure
- removable
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- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 95
- 239000004925 Acrylic resin Substances 0.000 title claims abstract description 75
- 229920000178 Acrylic resin Polymers 0.000 title claims abstract description 75
- 239000004820 Pressure-sensitive adhesive Substances 0.000 title claims abstract description 49
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 229920001971 elastomer Polymers 0.000 claims abstract description 46
- 239000005060 rubber Substances 0.000 claims abstract description 46
- 229920002367 Polyisobutene Polymers 0.000 claims abstract description 45
- 239000003999 initiator Substances 0.000 claims abstract description 29
- 239000000178 monomer Substances 0.000 claims abstract description 28
- 239000011347 resin Substances 0.000 claims abstract description 25
- 229920005989 resin Polymers 0.000 claims abstract description 25
- 238000003756 stirring Methods 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 17
- 239000011259 mixed solution Substances 0.000 claims abstract description 17
- 239000011261 inert gas Substances 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 23
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 claims description 20
- 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 15
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 15
- -1 acrylic ester Chemical class 0.000 claims description 10
- 239000012948 isocyanate Substances 0.000 claims description 10
- 150000002513 isocyanates Chemical group 0.000 claims description 10
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 9
- NQSLZEHVGKWKAY-UHFFFAOYSA-N 6-methylheptyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C(C)=C NQSLZEHVGKWKAY-UHFFFAOYSA-N 0.000 claims description 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 8
- GDWAYKGILJJNBB-UHFFFAOYSA-N diethyl 2-prop-2-enylpropanedioate Chemical compound CCOC(=O)C(CC=C)C(=O)OCC GDWAYKGILJJNBB-UHFFFAOYSA-N 0.000 claims description 8
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims description 8
- 150000003505 terpenes Chemical class 0.000 claims description 3
- 235000007586 terpenes Nutrition 0.000 claims description 3
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 claims description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 2
- LYUUVYQGUMRKOV-UHFFFAOYSA-N Diethyl diallylmalonate Chemical compound CCOC(=O)C(CC=C)(CC=C)C(=O)OCC LYUUVYQGUMRKOV-UHFFFAOYSA-N 0.000 claims description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 claims description 2
- AYEFIAVHMUFQPZ-UHFFFAOYSA-N propane-1,2-diol;prop-2-enoic acid Chemical compound CC(O)CO.OC(=O)C=C AYEFIAVHMUFQPZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 18
- 239000000853 adhesive Substances 0.000 abstract description 17
- 150000003254 radicals Chemical class 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 238000001723 curing Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 230000008569 process Effects 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- 239000012046 mixed solvent Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 230000009471 action Effects 0.000 description 5
- 239000003292 glue Substances 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000012949 free radical photoinitiator Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000007719 peel strength test Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000003335 steric effect Effects 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/06—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
- C08F255/08—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having four or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/06—Printing inks based on fatty oils
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/08—Printing inks based on natural resins
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention relates to the technical field of acrylic adhesives, and discloses a removable modified acrylic resin pressure-sensitive adhesive and a preparation method thereof; comprises the following steps: preparation of modified acrylic resin: dissolving polyisobutylene rubber in a solvent to obtain a polyisobutylene rubber solution; adding 50-60wt% of initiator under the protection of inert gas at 70-85 ℃ to uniformly mix and react for 2-3 hours at constant temperature, heating to 85-95 ℃, adding mixed solution containing acrylate soft monomer, acrylate functional monomer and 20-30wt% of initiator to uniformly mix and react for 3-4 hours at constant temperature, adding the rest initiator to react for 1-2 hours at constant temperature, and obtaining modified acrylic resin; preparation of modified acrylic resin pressure-sensitive adhesive: and uniformly stirring the modified acrylic resin, the tackifying resin and the curing agent to obtain the modified acrylic resin pressure-sensitive adhesive.
Description
Technical Field
The invention relates to the technical field of acrylic adhesives, in particular to a removable modified acrylic resin pressure-sensitive adhesive and a preparation method thereof.
Background
The implementation of various performances such as dampproof protection, insulating sealing, connection assembly, electric conduction, magnetic conduction and the like of the electronic element can use adhesives, and especially the rapid development of the microelectronics industry leads to miniaturization, ultra-thin, high performance and low cost of the electronic element, so that the dependence of the electronic element on the adhesives is greatly improved, and the performance requirements on the adhesives are also higher and higher. In the connection of electronic components, the bonding process of the adhesive is not replaced by other bonding processes, and the adhesive connecting material has the characteristics of low energy consumption, large effect, high benefit, uniform transmission and the like
The main varieties of electronic adhesives in the market at present are epoxy resin, organic silicon resin, modified phenolic resin, polyester resin, polyurethane resin, neoprene, polysulfide rubber and the like, and hot melt adhesives, water-soluble adhesives, anaerobic adhesives, pressure-sensitive adhesives, photo-curing adhesives, flame-retardant potting materials and the like which are developed according to the specificity and the process characteristics of electronic elements.
CN201711277073.5 a pressure-sensitive adhesive for eyelid retractor adhesion and a preparation method thereof disclose a preparation method of the pressure-sensitive adhesive, and discloses components of acrylic ester soft monomer, acrylic ester hard monomer, synthetic rubber, castor oil, initiator and vulcanizing agent, wherein the synthetic rubber is one or more selected from styrene-butadiene rubber, polyisobutylene rubber and butyl rubber; the vulcanizing agent is one or more selected from elemental sulfur, an accelerator TMTD, benzoyl peroxide and ethyl carbamate. But the vulcanizing agent is used for vulcanizing under high pressure in the synthesis process, so that the synthetic process route is complex and the synthetic condition is harsh.
CN114891447a discloses an acrylate/polyisobutylene rubber hybrid pressure sensitive adhesive composition comprising component (a), (meth) acrylate prepolymer, component (B), polyisobutylene rubber, component (C), and a free radical photoinitiator. Because the Polyisobutene (PIB) component with very low WVTR is introduced to form an Interpenetrating Polymer Network (IPN) in the whole molecular network, the very low WVTR characteristic of the PIB is fully utilized, so that the WVTR of the whole polyacrylate/polyisobutene rubber hybrid pressure-sensitive adhesive system is greatly reduced, the basic mechanical property of the pressure-sensitive adhesive is basically not influenced, and the application range is enlarged. The polyisobutene rubber with the viscosity average molecular weight of 30000-80000 is selected to reduce the viscosity average molecular weight of the whole adhesive system, and a free radical photoinitiator is used for polymerization and curing reaction by ultraviolet irradiation in the coating process. The selected polyisobutene rubber distribution limits the application of the synthesized product, and the photoinitiator promotes the recombination synthesis of free radicals in the coating process to increase the uncontrollable grafting and limit the thickness of the coating (the irradiation reason of ultraviolet light).
Therefore, the invention of the removable modified acrylic pressure-sensitive adhesive has important significance.
Disclosure of Invention
The invention aims to provide a removable modified acrylic resin pressure-sensitive adhesive and a preparation method thereof, which are used for solving the problems in the background technology.
In order to solve the technical problems, the invention provides the following technical scheme:
a method for preparing removable modified acrylic resin pressure-sensitive adhesive, comprising the following steps:
s1: preparation of modified acrylic resin: dissolving polyisobutylene rubber in a solvent to obtain a polyisobutylene rubber solution with a solid content of 30-40%; adding 50-60wt% of initiator under the protection of inert gas at 70-85 ℃ to uniformly mix and react for 2-3 hours at constant temperature, heating to 85-95 ℃, adding mixed solution containing acrylate soft monomer, acrylate functional monomer and 20-30wt% of initiator to uniformly mix and react for 3-4 hours at constant temperature, adding the rest initiator to react for 1-2 hours at constant temperature, and obtaining modified acrylic resin;
s2: preparation of modified acrylic resin pressure-sensitive adhesive: uniformly stirring the modified acrylic resin, the tackifying resin and the curing agent to obtain a modified acrylic resin pressure-sensitive adhesive;
further, in the modified acrylic resin, the weight ratio of the raw material components is 9-14 parts of polyisobutylene rubber, 40-60 parts of acrylate monomer, 5-10 parts of acrylate functional monomer, 0.135-0.21 part of initiator and 150-210 parts of solvent.
Further, the polyisobutylene rubber has a viscosity average molecular weight of 80000-115000; polyisobutylene rubber: the mass ratio of the total mass of the acrylic ester monomer to the acrylic ester functional monomer is 1:5;
further, the acrylic ester monomer is any one or more of n-octyl methacrylate, diethyl allylmalonate, diethyl diallylmalonate, isooctyl methacrylate, methyl methacrylate, lauryl methacrylate and vinyl versatate.
Further, the acrylate functional monomer is any one or more of acrylic acid-2-hydroxyethyl ester, acrylic acid-2-hydroxypropyl ester, (methyl) acrylic acid hydroxybutyl ester and N-methylolacrylamide.
Further, the initiator is any one of azodiisoheptonitrile and dibenzoyl peroxide; the addition amount of the initiator is 1-2wt% of the polyisobutene rubber.
Further, the solvent is a combination of any two of ethyl acetate, n-butyl ester and ethylcyclohexane, and the mass ratio of the solvent combination is 1:1.
Further, the weight average molecular weight of the modified acrylic resin is 600000-800000, and Tg is-0.5-5deg.C.
Further, the curing agent is isocyanate curing agent, and the adding amount of the curing agent is 0.3-0.5wt% of the mass of the modified acrylic resin.
Further, the tackifying resin is any one or more of rosin resin and terpene resin, and the softening point temperature of the tackifying resin is 95-150 ℃.
Further, the addition amount of the tackifying resin is 20-40wt% of the mass of the modified acrylic resin
Compared with the prior art, the invention has the following beneficial effects:
1. according to the invention, the polyisobutylene rubber is introduced into the synthetic acrylic resin, so that the synthesized modified acrylic resin material has the flexibility of a rubber base and the low-temperature soft elasticity, the cohesion of a glue system is increased, and meanwhile, the adhesive property of the acrylic resin is also realized.
2. The invention selects double temperature section control in the synthesis process, firstly, under the inert gas protection atmosphere of 70-85 ℃, the double bond of polyisobutene is ring-opened to form free radical under the action of an initiator; then gradually heating to 85-95 ℃, and linking the free radical formed by the acrylic acid monomer and the free radical formed by ring opening of the polyisobutene double bond into a network structure under the action of an initiator. Because the quantity of free radicals and the molecular weight after synthesis can be regulated and controlled by controlling the quantity of the initiator, the invention is characterized in that the initiator is always in a low concentration level in the synthesis process, polyisobutene preferentially forms macromolecular free radicals under the action of the initiator and then is synthesized with acrylic acid micromolecules, thereby being beneficial to synthesizing the modified acrylic resin by the action of the acrylic acid monomer and the acrylic acid monomer, simplifying the synthesis process and greatly improving the synthesis efficiency; if the acrylic acid prepolymer is synthesized firstly and then synthesized with macromolecular polyisobutene, the steric effect of free radical linkage can be improved, the synthesis temperature and time are increased, and the combination quantity of the free radicals and the molecular weight after synthesis are uncontrollable.
3. The modified acrylic resin pressure-sensitive adhesive prepared by the modified acrylic resin has good high-low temperature rapid stripping performance without residual adhesive as a solvent type adhesive. The conventional acrylic pressure-sensitive adhesive presents a glass state in a low-temperature environment, such as-20 ℃, and the state of degumming and residual adhesive can appear in the rapid stripping process; under the high-temperature environment, the adhesive state is shown at 85 ℃, the cohesion of the resin is low, and the adhesive residue state can be caused by rapid stripping; in the invention, rubber materials are added in the system, and the modified acrylic resin has rubber state properties at low temperature and high temperature, and can be peeled off quickly at high and low temperature without degumming or residual rubber.
Drawings
The accompanying drawings are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate the invention and together with the embodiments of the invention, serve to explain the invention. In the drawings:
FIG. 1 is an IR test spectrum of a modified acrylic resin of example 1;
wherein, before modification, the acrylic resin IR prepared by the same proportion and the same synthesis mode is prepared without adding polyisobutylene modified rubber;
FIG. 2 is a graph of the rheological test of the modified acrylic resin of example 1;
FIG. 3 is a GPC chart of the modified acrylic resin of example 1;
FIG. 4 is a GPC test chart of comparative example 1;
FIG. 5 is a GPC test chart of comparative example 2;
FIG. 6 is a GPC test chart of comparative example 3;
FIG. 7 is a GPC chart of comparative example 4.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
It should be noted that the manufacturers of all the raw materials according to the present invention include, without any particular limitation: polyisobutylene rubber was purchased from basf; model number isB13 SFN, weight average molecular weight 82588; tackifying resins were purchased from koteng; the isocyanate curing agent is Desmodur L75; the tackifying resin is terpene phenol tackifying resin TP2040 with molecular weight of 850g/mol.
Example 1: a preparation method of a removable modified acrylic resin pressure-sensitive adhesive, which comprises the following steps: s1: adding 75 parts of ethyl acetate and 75 parts of ethylcyclohexane mixed solvent into a three-neck flask, stirring at a constant temperature and refluxing through a condenser tube under the protection of 75 ℃ inert gas, slowly adding 9 parts of polyisobutene rubber particles, adding 0.0675 part of dibenzoyl peroxide after the rubber materials are completely dissolved, heating to 90 ℃ after keeping the temperature constant for 3 hours, slowly dropwise adding a mixed solution containing 15 parts of n-octyl acrylate, 5 parts of diethyl allylmalonate, 15 parts of isooctyl methacrylate, 3 parts of methyl methacrylate, 2 parts of lauryl methacrylate, 5 parts of 2-hydroxyethyl acrylate and 0.027 part of dibenzoyl peroxide, keeping the temperature for 3 hours after the dropwise adding is completed, and dropwise adding the rest part of initiator for keeping the temperature for 1 hour to obtain modified acrylic resin;
s2: adding the modified acrylic resin, 0.3wt% of isocyanate curing agent and 20wt% of tackifying resin into a mixing and stirring kettle, and stirring for 30min at 500-700r/min to obtain the modified acrylic resin pressure-sensitive adhesive.
Example 2: a preparation method of a removable modified acrylic resin pressure-sensitive adhesive, which comprises the following steps: s1: adding 75 parts of ethyl acetate and 75 parts of ethylcyclohexane mixed solvent into a three-neck flask, stirring at constant temperature and refluxing through a condenser tube under the protection of 75 ℃ inert gas, slowly adding 10 parts of polyisobutene rubber particles, adding 0.0825 part of dibenzoyl peroxide after the rubber materials are completely dissolved, heating to 90 ℃ after keeping constant temperature for 3 hours, slowly dropwise adding a mixed solution containing 18 parts of n-octyl acrylate, 5 parts of diethyl allylmalonate, 10 parts of isooctyl methacrylate, 5 parts of methyl methacrylate, 5 parts of lauryl methacrylate, 7 parts of 2-hydroxyethyl acrylate and 0.0375 part of dibenzoyl peroxide, keeping constant temperature for 3 hours after 1 hour, and dropwise adding the rest part of initiator after keeping constant temperature for 1 hour to obtain modified acrylic resin;
s2: adding the modified acrylic resin, 0.4wt% of isocyanate curing agent and 20wt% of tackifying resin into a mixing and stirring kettle, and stirring for 30min at 500-700r/min to obtain the modified acrylic resin pressure-sensitive adhesive.
Example 3: a preparation method of a removable modified acrylic resin pressure-sensitive adhesive, which comprises the following steps: s1: adding 100 parts of ethyl acetate and 100 parts of ethylcyclohexane mixed solvent into a three-neck flask, stirring at constant temperature and refluxing through a condenser tube under the protection of 75 ℃ inert gas, slowly adding 14 parts of polyisobutene rubber particles, adding 0.126 part of dibenzoyl peroxide after the rubber materials are completely dissolved, heating to 90 ℃ after keeping constant temperature for 3 hours, slowly dropwise adding a mixed solution containing 25 parts of n-octyl acrylate, 7 parts of diethyl allylmalonate, 8 parts of isooctyl methacrylate, 3 parts of methyl methacrylate, 10 parts of lauryl methacrylate, 10 parts of 2-hydroxyethyl acrylate and 0.063 part of dibenzoyl peroxide, keeping constant temperature for 3 hours after 1 hour dropwise adding the rest of initiator, keeping constant temperature for 1 hour, and obtaining modified acrylic resin;
s2: adding the modified acrylic resin, 0.5wt% of isocyanate curing agent and 20wt% of tackifying resin into a mixing and stirring kettle, and stirring for 30min at 500-700r/min to obtain the modified acrylic resin pressure-sensitive adhesive.
Comparative example 1: a preparation method of a removable modified acrylic resin pressure-sensitive adhesive, which comprises the following steps: s1: adding 90 parts of ethyl acetate and 90 parts of ethylcyclohexane mixed solvent into a three-neck flask, stirring at constant temperature and refluxing through a condenser tube under the protection of 75 ℃ inert gas, slowly adding 10 parts of polyisobutylene rubber particles, wherein the viscosity average molecular weight of the polyisobutylene rubber is 5W, adding 0.0825 part of dibenzoyl peroxide after the rubber material is completely dissolved, keeping the temperature for 3 hours, heating to 90 ℃ and keeping the temperature, slowly dropwise adding a mixed solution containing 18 parts of n-octyl acrylate, 5 parts of diethyl allylmalonate, 10 parts of isooctyl methacrylate, 5 parts of methyl methacrylate, 5 parts of lauryl methacrylate, 7 parts of 2-hydroxyethyl acrylate and 0.0375 part of dibenzoyl peroxide, keeping the temperature for 3 hours after the dropwise adding is completed, and dropwise adding the rest part of initiator to keep the temperature for 1 hour to obtain modified acrylic resin;
s2: adding the modified acrylic resin, 0.4wt% of isocyanate curing agent and 20wt% of tackifying resin into a mixing and stirring kettle, and stirring for 30min at 500-700r/min to obtain the modified acrylic resin pressure-sensitive adhesive.
Comparative example 2: a preparation method of a removable modified acrylic resin pressure-sensitive adhesive, which comprises the following steps: s1: adding 90 parts of ethyl acetate and 90 parts of ethylcyclohexane mixed solvent into a three-neck flask, stirring at constant temperature and refluxing through a condenser tube under the protection of 75 ℃ inert gas, slowly adding 10 parts of polyisobutene rubber particles, wherein the viscosity average molecular weight of the polyisobutene rubber is 15W, adding 0.0825 part of dibenzoyl peroxide after the rubber material is completely dissolved, keeping the temperature for 3 hours, heating to 90 ℃ and keeping the temperature, slowly dropwise adding a mixed solution containing 18 parts of n-octyl acrylate, 5 parts of diethyl allylmalonate, 10 parts of isooctyl methacrylate, 5 parts of methyl methacrylate, 5 parts of lauryl methacrylate, 7 parts of 2-hydroxyethyl acrylate and 0.0375 part of dibenzoyl peroxide, keeping the temperature for 3 hours after the dropwise adding is completed, and dropwise adding the rest part of initiator to keep the temperature for 1 hour to obtain modified acrylic resin;
s2: adding the modified acrylic resin, 0.4wt% of isocyanate curing agent and 20wt% of tackifying resin into a mixing and stirring kettle, and stirring for 30min at 500-700r/min to obtain the modified acrylic resin pressure-sensitive adhesive.
Comparative example 3: a preparation method of a removable modified acrylic resin pressure-sensitive adhesive, which comprises the following steps: s1: adding 30 parts of ethyl acetate and 30 parts of ethylcyclohexane mixed solvent into a three-neck flask, slowly adding 10 parts of polyisobutene rubber particles, and continuously stirring at 75 ℃ until the rubber is dissolved to obtain a mixed solution A;
s2: to a three-necked flask, 60 parts of ethyl acetate, 60 parts of an ethylcyclohexane mixed solvent, and a mixed solution B of an acrylic acid monomer and an initiator in a ratio of 60% were added, the mixed solution B comprising n-octyl 18, diethyl 5 allylmalonate, isooctyl 10 (meth) acrylate, methyl 5 (meth) acrylate, lauryl 5 (meth) acrylate, 7 parts of 2-hydroxyethyl acrylate, and 0.15 part of dibenzoyl peroxide; stirring at constant temperature and refluxing in a condensing tube for 1h under the protection of inert gas at 85 ℃; slowly dripping the mixed solution A and the mixed solution B with the residual 40 percent into a reaction system for 4 hours, and polymerizing at constant temperature for 3 hours after the dripping is finished to obtain modified acrylic resin;
s2: adding the modified acrylic resin, 0.4wt% of isocyanate curing agent and 20wt% of tackifying resin into a mixing and stirring kettle, and stirring for 30min at 500-700r/min to obtain the modified acrylic resin pressure-sensitive adhesive
Comparative example 4: a preparation method of a removable modified acrylic resin pressure-sensitive adhesive, which comprises the following steps: s1: adding 75 parts of ethyl acetate and 75 parts of ethylcyclohexane mixed solvent into a three-neck flask, stirring at constant temperature and refluxing through a condenser tube under the protection of inert gas at 75 ℃, adding 80% of mixed solution, wherein the mixed solution comprises 15 parts of n-octyl acrylate, 5 parts of diethyl allylmalonate, 15 parts of isooctyl methacrylate, 3 parts of methyl methacrylate, 2 parts of lauryl methacrylate, 5 parts of 2-hydroxyethyl acrylate and 0.027 part of dibenzoyl peroxide, performing constant temperature reaction for 1h, slowly dropwise adding the mixed solution with the remaining 20% of mixed solution, keeping at constant temperature for 3h, and adding 0.03 part of initiator for constant temperature reaction for 1h to obtain modified acrylic resin;
s2: adding the modified acrylic resin, 0.4wt% of isocyanate curing agent and 20wt% of tackifying resin into a mixing and stirring kettle, and stirring for 30min at 500-700r/min to obtain the modified acrylic resin pressure-sensitive adhesive.
And (3) testing: the modified acrylic resins prepared in examples 1 to 3 and comparative examples 1 to 4 above were coated with 25 μm thick dry glue on 25 μm PET for testing the graft conversion;
conversion, grafting and grafting efficiency of monomer: and (3) putting a glue film with proper size into a methanol solution, soaking for 2H, removing unreacted monomers in the glue film to obtain a graft polymer, taking out a sample, drying the sample to constant weight at 40 ℃, putting the sample into a Soxhlet extractor, extracting the sample with acetone for 48H, weighing residues to constant weight respectively, and calculating to obtain the polymer.
The modified acrylic pressure sensitive adhesive was coated with 25 μm thick dry glue on 25 μm pet for test use.
Peel force test: test with reference to the standard adhesive tape peel strength test method (GB/T2792-2014);
retention test: the test was carried out with reference to test method for the holding power of adhesive tapes (GB/T4851-2014), and the test data are shown in the following Table.
Table 1 pressure sensitive adhesive performance test prepared in each example and comparative example
Conclusion: the modified acrylic resin pressure-sensitive adhesive prepared in examples 1-3 has excellent high-low temperature quick stripping performance.
The low molecular weight polyisobutylene rubber is selected in the comparative example 1, the bonding effect of the free radical and the acrylic acid is good, the molecular weight is large, but the modified acrylic acid has poor quick tearing base adhesion at low temperature due to high synthesized cohesion;
in the comparative example 2, high molecular weight polyisobutylene rubber is selected, the polyisobutylene generates macromolecular free radicals under the action of an initiator, and the acrylic acid monomer grafting rate is low due to the steric hindrance effect, so that the modified acrylic resin is subjected to quick-tearing at low temperature to form residual gum;
comparative example 3 the synthetic process of the modified acrylic resin was changed, and the conventional acrylic resin synthesis process was used, the acrylic radical bonded polyisobutylene radical, the radical grafting effect was poor, the cohesion of the synthesized product was low, and the effect intended by the present invention was not achieved;
comparative example 4 the synthetic process of the modified acrylic resin was changed, and polyisobutylene rubber was not added as a modifier, so that the free radical formed by the acrylic monomer could not be linked with the free radical formed by ring opening of the polyisobutylene double bond to form a network structure, the free radical grafting effect was poor, and the cohesion of the synthesized product was low, and the effect intended by the present invention was not achieved.
Finally, it should be noted that: the foregoing description is only a preferred embodiment of the present invention, and the present invention is not limited thereto, but it is to be understood that modifications and equivalents of some of the technical features described in the foregoing embodiments may be made by those skilled in the art, although the present invention has been described in detail with reference to the foregoing embodiments. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A preparation method of a removable modified acrylic resin pressure-sensitive adhesive is characterized in that: comprises the following steps:
s1: preparation of modified acrylic resin: dissolving polyisobutylene rubber in a solvent to obtain a polyisobutylene rubber solution; adding 50-60wt% of initiator under the protection of inert gas at 70-85 ℃ to uniformly mix and react for 2-3 hours at constant temperature, heating to 85-95 ℃, adding mixed solution containing acrylate soft monomer, acrylate functional monomer and 20-30wt% of initiator to uniformly mix and react for 3-4 hours at constant temperature, adding the rest initiator to react for 1-2 hours at constant temperature, and obtaining modified acrylic resin;
s2: preparation of modified acrylic resin pressure-sensitive adhesive: and uniformly stirring the modified acrylic resin, the tackifying resin and the curing agent to obtain the modified acrylic resin pressure-sensitive adhesive.
2. The method for preparing the removable modified acrylic pressure-sensitive adhesive according to claim 1, wherein: in the modified acrylic resin, 9-14 parts of polyisobutylene rubber, 40-60 parts of acrylate monomer, 5-10 parts of acrylate functional monomer, 0.135-0.21 part of initiator and 150-210 parts of solvent by mass; the solid content of the polyisobutene rubber solution is 30-40%.
3. The method for preparing the removable modified acrylic pressure-sensitive adhesive according to claim 2, wherein: the viscosity average molecular weight of the polyisobutene rubber is 80000-115000; polyisobutylene rubber: the mass ratio of the total mass of the acrylic ester monomer to the acrylic ester functional monomer is 1 (4.5-5.5).
4. The method for preparing the removable modified acrylic pressure-sensitive adhesive according to claim 1, wherein: in the step S1, the acrylic ester monomer is any one or more of n-octyl methacrylate, diethyl allylmalonate, diethyl diallylmalonate, isooctyl methacrylate, methyl methacrylate, lauryl methacrylate and vinyl versatate.
5. The method for preparing the removable modified acrylic pressure-sensitive adhesive according to claim 1, wherein: in the step S1, the acrylate functional monomer is any one or more of acrylic acid-2-hydroxyethyl ester, acrylic acid-2-hydroxypropyl ester, (methyl) acrylic acid hydroxybutyl ester and N-methylolacrylamide.
6. The method for preparing the removable modified acrylic pressure-sensitive adhesive according to claim 2, wherein: the initiator is any one of azodiisoheptonitrile and dibenzoyl peroxide; the addition amount of the initiator is 1-2wt% of the polyisobutene rubber.
7. The method for preparing the removable modified acrylic resin pressure-sensitive adhesive according to claim 2, wherein the solvent is a combination of any two of ethyl acetate, n-butyl ester and ethylcyclohexane, and the mass ratio of the solvent combination is 1:1.
8. The method for preparing the removable modified acrylic pressure-sensitive adhesive according to claim 1, wherein: in the step S2, the curing agent is isocyanate curing agent, and the adding amount of the curing agent is 0.3-0.5wt% of the mass of the modified acrylic resin.
9. The method for preparing the removable modified acrylic pressure-sensitive adhesive according to claim 1, wherein: in the step S2, the tackifying resin is any one or more of rosin resin and terpene resin, and the softening point temperature of the tackifying resin is 95-150 ℃; the addition amount of the tackifying resin is 20-40wt% of the mass of the modified acrylic resin.
10. The modified acrylic pressure-sensitive adhesive prepared by the method for preparing a removable modified acrylic pressure-sensitive adhesive according to any one of claims 1 to 9.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117327230A (en) * | 2023-11-29 | 2024-01-02 | 江苏皇冠新材料科技有限公司 | Polyisobutylene grafted acrylate copolymer, adhesive and pressure-sensitive adhesive tape |
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| US5695837A (en) * | 1995-04-20 | 1997-12-09 | Minnesota Mining And Manufacturing Company | Tackified acrylic adhesives |
| EP1028151A1 (en) * | 1999-02-12 | 2000-08-16 | Lohmann GmbH & Co. KG | Pressure sensitive adhesive and structural adhesive for the aggressive fixation of joint parts followed by curing in the glue joint adding thermal energy |
| CN109054701A (en) * | 2018-07-11 | 2018-12-21 | 江苏景宏新材料科技有限公司 | Low temperature resistant pressure-sensitive adhesive agent and preparation method thereof |
| CN115074058A (en) * | 2022-07-06 | 2022-09-20 | 中山市皇冠胶粘制品有限公司 | Pressure-sensitive adhesive used in wide temperature range and preparation method of double-sided adhesive tape thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5695837A (en) * | 1995-04-20 | 1997-12-09 | Minnesota Mining And Manufacturing Company | Tackified acrylic adhesives |
| EP1028151A1 (en) * | 1999-02-12 | 2000-08-16 | Lohmann GmbH & Co. KG | Pressure sensitive adhesive and structural adhesive for the aggressive fixation of joint parts followed by curing in the glue joint adding thermal energy |
| CN109054701A (en) * | 2018-07-11 | 2018-12-21 | 江苏景宏新材料科技有限公司 | Low temperature resistant pressure-sensitive adhesive agent and preparation method thereof |
| CN115074058A (en) * | 2022-07-06 | 2022-09-20 | 中山市皇冠胶粘制品有限公司 | Pressure-sensitive adhesive used in wide temperature range and preparation method of double-sided adhesive tape thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117327230A (en) * | 2023-11-29 | 2024-01-02 | 江苏皇冠新材料科技有限公司 | Polyisobutylene grafted acrylate copolymer, adhesive and pressure-sensitive adhesive tape |
| CN117327230B (en) * | 2023-11-29 | 2024-03-05 | 江苏皇冠新材料科技有限公司 | Polyisobutylene grafted acrylate copolymer, adhesive and pressure-sensitive adhesive tape |
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