CN110546175A - (甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物、其制备方法和用途 - Google Patents
(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物、其制备方法和用途 Download PDFInfo
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- CN110546175A CN110546175A CN201780089843.5A CN201780089843A CN110546175A CN 110546175 A CN110546175 A CN 110546175A CN 201780089843 A CN201780089843 A CN 201780089843A CN 110546175 A CN110546175 A CN 110546175A
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 106
- 229920000193 polymethacrylate Polymers 0.000 title claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title abstract description 7
- 239000000203 mixture Substances 0.000 claims description 29
- 239000000853 adhesive Substances 0.000 claims description 25
- 230000001070 adhesive effect Effects 0.000 claims description 25
- 229920001577 copolymer Polymers 0.000 claims description 24
- 239000004642 Polyimide Substances 0.000 claims description 23
- 229920001721 polyimide Polymers 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229920005575 poly(amic acid) Polymers 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001174 sulfone group Chemical group 0.000 claims description 3
- 125000000101 thioether group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical group OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 claims description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims description 2
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 2
- -1 aliphatic radical Chemical class 0.000 description 37
- 229920001400 block copolymer Polymers 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 11
- 239000004926 polymethyl methacrylate Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 238000002411 thermogravimetry Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000003643 water by type Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZKAZRWDWXSFBIQ-UHFFFAOYSA-N 6-aminohexyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(Br)C(=O)OCCCCCCN ZKAZRWDWXSFBIQ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012766 organic filler Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 239000013008 thixotropic agent Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- DKCPAVYKGYMCPR-UHFFFAOYSA-N [Cl-].BrC(C(=O)OCCCCCC[NH3+])(C)C Chemical compound [Cl-].BrC(C(=O)OCCCCCC[NH3+])(C)C DKCPAVYKGYMCPR-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002950 monocyclic group Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- NQUXRXBRYDZZDL-UHFFFAOYSA-N 1-(2-prop-2-enoyloxyethyl)cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1(CCOC(=O)C=C)C(O)=O NQUXRXBRYDZZDL-UHFFFAOYSA-N 0.000 description 1
- WQHNZXURJISVCT-UHFFFAOYSA-N 1-butoxyethane-1,2-diol Chemical compound CCCCOC(O)CO WQHNZXURJISVCT-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- YOCIJWAHRAJQFT-UHFFFAOYSA-N 2-bromo-2-methylpropanoyl bromide Chemical compound CC(C)(Br)C(Br)=O YOCIJWAHRAJQFT-UHFFFAOYSA-N 0.000 description 1
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 description 1
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- UDXXYUDJOHIIDZ-UHFFFAOYSA-N 2-phosphonooxyethyl prop-2-enoate Chemical compound OP(O)(=O)OCCOC(=O)C=C UDXXYUDJOHIIDZ-UHFFFAOYSA-N 0.000 description 1
- BCUQFWKUDOLOFV-UHFFFAOYSA-N 3-hydroxy-4-(2-hydroxyethoxy)butanoic acid Chemical compound C(=O)(O)CC(COCCO)O BCUQFWKUDOLOFV-UHFFFAOYSA-N 0.000 description 1
- LJMPOXUWPWEILS-UHFFFAOYSA-N 3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1C2C(=O)OC(=O)C2CC2C(=O)OC(=O)C21 LJMPOXUWPWEILS-UHFFFAOYSA-N 0.000 description 1
- BEKFRNOZJSYWKZ-UHFFFAOYSA-N 4-[2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]aniline Chemical compound C1=CC(N)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(N)C=C1 BEKFRNOZJSYWKZ-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
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- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- NIGQYXXKOLEGJU-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCC)(=O)O.C(CCCCCCCCCCCCCCCCC)(=O)O.C1=CC=CC1 Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)O.C(CCCCCCCCCCCCCCCCC)(=O)O.C1=CC=CC1 NIGQYXXKOLEGJU-UHFFFAOYSA-N 0.000 description 1
- PNVWNTUCFLZBSE-UHFFFAOYSA-N CC(O)COC(=O)c1ccccc1C(=O)OCCOC(=O)C=C Chemical compound CC(O)COC(=O)c1ccccc1C(=O)OCCOC(=O)C=C PNVWNTUCFLZBSE-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
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- 239000004793 Polystyrene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 241000276425 Xiphophorus maculatus Species 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- OJMOMXZKOWKUTA-UHFFFAOYSA-N aluminum;borate Chemical compound [Al+3].[O-]B([O-])[O-] OJMOMXZKOWKUTA-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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Abstract
本发明涉及(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯‑嵌段‑聚酰亚胺‑嵌段‑聚(甲基)丙烯酸酯共聚物、其制备方法和用途。根据本发明的(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯‑嵌段‑聚酰亚胺‑嵌段‑聚(甲基)丙烯酸酯共聚物表现出优异的热稳定性和优异的光学性能。
Description
技术领域
本发明涉及(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物、其制备方法和用途。根据本发明的(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物表现出优异的热稳定性和优异的光学性能。
背景技术
已知聚酰亚胺具有良好的热稳定性、耐化学性和机械性质等。然而,由于聚酰亚胺的溶解度低,与粘合剂的常见组分的相容性差,熔点高以及加工极其困难,聚酰亚胺在粘合剂中的应用受到限制。
已经进行了许多研究来改变聚酰亚胺的热性质和机械性质。例如,Fu-Ming Wang等合成了基于聚(丙烯酸酯-共-酰亚胺)的凝胶聚合物电解质。参见“The network gelpolymer electrolyte based on poly(acrylate-co-imide)and its transportproperties in lithium ion batteries”,J Solid State Electrochem(2009)13:1425-1431。那些基于聚(丙烯酸酯-共-酰亚胺)的凝胶聚合物是接枝聚合物。这些接枝聚合物不溶于大多数有机溶剂。此外,酰亚胺部分与丙烯酸酯部分之间的键很弱,这可能损害接枝聚合物的热稳定性。
尽管有现有技术,但仍需要开发既显示良好热稳定性又显示良好光学性能的新型粘合剂材料。
发明内容
经过深入研究,本发明的发明人们开发出一种新型(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物,其由式I表示:
在式(I)中,m和n各自独立地表示1至约50的整数,条件是m和n不同时为1;
R1和R14彼此相同或不同,独立地为氢或甲基;
R2选自C1-C12烷基;
R3是-CH(CH3)-或-C(CH3)2-;
R4选自C1-C12亚烷基;
R5表示选自C6-C30脂环族基团和C6-C30亚芳基的二价连接单元;并且
A表示选自C4-C14脂族基团、C4-C30脂环族基团、C6-C30芳基、醚基、砜基、硫醚基、酰胺基和酯基的四价连接单元。
本发明还涉及制备根据本发明的共聚物的方法。
本发明还涉及包含根据本发明的共聚物的可光固化粘合剂组合物。
本发明还涉及根据本发明的粘合剂组合物在粘合基材中的用途。
附图说明
结合附图,从下面的详细描述中,本公开的附加特征和优点将变得显而易见,附图和详细描述通过示例一起示出了该技术特征;并且,其中:
图1比较了根据本发明实施例和对比例制备的共聚物的UV-VIS透射-波长图。
图2比较了根据本发明实施例和对比例制备的共聚物的热重分析(TGA)曲线。
图3至5各自显示了根据本发明实施例制备的共聚物的热重分析(TGA)曲线。
图6显示了根据对比例制备的共聚物的热重分析(TGA)曲线。
现在将参考一些说明性实例,并且这里将使用特定的语言来描述它们。然而,应当理解,并不因此意图限制本公开的范围。
具体实施方式
在以下段落中,更详细地描述本公开。除非明确给出相反指示,否则如此描述的每个方面可以与任何其它一个或多个方面组合。特别地,任何被指示为优选或有利的特征可以与任何其它被指示为优选或有利的一个或多个特征组合。
在本公开的上下文中,除非上下文另有说明,否则所使用的术语应根据以下定义来解释。
除非上下文另有明确说明,否则本文所用的单数形式“一(a、an)”和“所述(the)”包括单数和复数指代物。
本文所用的术语“包含(comprising、comprises和comprised of)”与“包括(including、includes)”或“含有(containing、contains)”同义,并且是包括性的或开放式的,并且不排除另外的、未列举的构件、元件或方法步骤。
在说明书中,术语“(甲基)丙烯酸酯”是指丙烯酸酯和甲基丙烯酸酯两者或其中之一,术语“(甲基)丙烯酸”表示丙烯酸和甲基丙烯酸两者或其中之一,术语“聚(甲基)丙烯酸酯”表示聚丙烯酸酯和聚甲基丙烯酸酯两者或其中之一。
数值端点的列举包括包含在相应范围内的所有数字和分数,以及所列举的端点。
本说明书中引用的所有参考文献以引用的方式整体并入本文。
除非另有定义,否则在本公开中使用的所有术语,包括科技术语,具有本公开所属领域的普通技术人员通常理解的含义。借助于进一步的指导,本文包括术语定义以更好地理解本公开的教导。
除非特别指出,否则本公开中使用的所有材料和试剂都可商购获得。
(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙
烯酸酯共聚物
在一个方面,本发明提供(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物,其由式I表示:
在式(I)中,m和n各自独立地表示约1至约50的整数,条件是m和n不同时为1;
R1和R14彼此相同或不同,独立地为氢或甲基;
R2选自C1-C12烷基,优选地,R2选自C1-C6烷基;
R3是-CH(CH3)-或-C(CH3)2-;
R4选自C1-C12亚烷基,优选地,R4选自C1-C6亚烷基;
R5表示选自C6-C30脂环族基团和C6-C30亚芳基的二价连接单元;并且
A表示选自C4-C14脂族基团、C4-C30脂环族基团、C6-C30芳基、醚基、砜基、硫醚基、酰胺基和酯基的四价连接单元。
令人惊讶地发现,根据本发明的(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物表现出优异的热稳定性和优异的光学性能。此外,该嵌段共聚物可溶于各种溶剂和单体,易于加工,并与粘合剂的常见组分例如(甲基)丙烯酸类树脂相容。
不受任何理论的限制,相信根据本发明的嵌段共聚物的聚酰亚胺嵌段赋予(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物优异的热稳定性。通过用(甲基)丙烯酸酯改性聚酰亚胺嵌段和端基,(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物进一步表现出优异的光学性能。(甲基)丙烯酸酯嵌段还赋予共聚物良好的柔韧性,这又显著改善共聚物的溶解性、相容性和可加工性。
本文所用的术语“脂族基团”是指完全饱和或者含有一个或多个不饱和单元但不是芳族的线性或支化、取代或未取代的烃链。合适的脂族基团包括但不限于线性或支化、取代或未取代的烷基、烯基和炔基。在一些实施方案中,脂族基团含有1-20个碳原子。脂族基团可以任选地被例如卤素、烷基、烯基、环烷基、硝基、羟基、氨基、烷基氨基、烷氧基、烷硫基或酰基取代。
术语“烷基”是指饱和的线性或支化、取代或未取代的单价烃基,其中烷基可以任选地被例如卤素、烷基、烯基、环烷基、硝基、羟基、氨基、烷基氨基、烷氧基、烷硫基或酰基取代。在一些实施方案中,烷基具有1-20个碳原子,优选1-12个碳原子,更优选1-6个碳原子。烷基的一些非限制性实例包括甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基等。
术语“亚烷基”是指通过除去两个氢原子而衍生自线性或支化饱和烃的饱和二价烃基,其中亚烷基可以任选地被例如卤素、烷基、烯基、环烷基、硝基、羟基、氨基、烷基氨基、烷氧基、烷硫基或酰基取代。在一些实施方案中,亚烷基具有1-20个碳原子,优选1-12个碳原子,更优选1-6个碳原子。亚烷基的一些非限制性实例包括亚甲基、亚乙基、亚丙基、亚丁基、亚戊基、亚己基、亚庚基、亚辛基、亚壬基、亚癸基等。
术语“烯基”是指具有至少一个碳-碳不饱和双键位点的线性或支化单价烃基,其中烯基可以任选地被取代。在一些实施方案中,烯基具有2-20个碳原子,优选2-12个碳原子,更优选2-6个碳原子。合适的烯基的非限制性实例包括乙烯基、丙烯基、丁烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、癸烯基、十一烯基、十二烯基等。
术语“炔基”是指具有至少一个碳-碳不饱和三键位点的线性或支化单价烃基,其中炔基可以任选地被取代。在一些实施方案中,炔基具有2-20个碳原子,优选2-12个碳原子,更优选2-6个碳原子。合适的炔基的非限制性实例包括乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基、辛炔基、壬炔基、癸炔基、十一炔基、十二炔基等。
术语“脂环族”是指单环或多环(例如双环和三环)环体系形式的单价或多价非芳族、饱和或部分不饱和的环。合适的脂环族基团包括但不限于环烷基、环烯基和环炔基。脂环族基团可以任选地被例如卤素、烷基、烯基、环烷基、硝基、羟基、氨基、烷基氨基、烷氧基、烷硫基或酰基取代。
术语“环烷基”是指任选取代的具有3-30个环碳原子,更优选4-30个环碳原子的饱和环体系。示例性单环环烷基包括环丙基、环丁基、环戊基、环己基、环庚基等。
本文所用的术语“环烯基”是指具有一个或多个碳-碳不饱和双键的环状脂族烃基。在一个实施方案中,环烯基在环体系中具有3-30个碳原子,更优选4-30个环碳原子。
本文所用的术语“环炔基”是指具有一个或多个碳-碳不饱和三键的环状脂族烃基。在一个实施方案中,环炔基在环体系中具有3-30个碳原子,更优选4-30个环碳原子。
术语“芳基”是指任选被被取代的包含1-3个芳环的C6-C30芳烃部分。这种基团的具体实例包括但不限于苯基、甲苯基、二甲苯基和萘基,特别是苯基或萘基。芳基可以任选地被例如卤素、烷基、烯基、环烷基、硝基、羟基、氨基、烷基氨基、烷氧基、烷硫基或酰基取代。
本文所用的术语“亚芳基”表示如本文所述的芳基体系,但与分子的其余部分具有两个连接点。
在一些实施方案中,A选自以下基团:
其中R6是二价连接单元,优选地,R6位于苯环的3,3'-、3,4'-、4,3'-或4,4'-位置,
更优选地,R6选自-O-、-S-、-C(O)-、-SO2-、-SO-、C1-C20亚烷基、卤代C1-C20亚烷基(包括C1-C20全氟亚烷基)和由-O-Z-O-表示的基团,其中Z是选自以下基团的二价连接基团:
其中R7选自-O-、-S-、-C(O)-、-SO2-、-SO-、C1-C20亚烷基和卤代C1-C20亚烷基(包括C1-C20全氟亚烷基);
甚至更优选地,R6选自C1-C12亚烷基和卤代C1-C12亚烷基,例如C1-C12全氟亚烷基。
本文所用的术语“卤代”是指氟代、氯代、溴代、碘代或它们的任意组合。
在一些实施方案中,R5选自以下基团:
其中R8至R13各自独立地选自C1-C20亚烷基及其卤代衍生物,包括C1-C20全氟亚烷基;优选C1-C12亚烷基及其卤代衍生物,例如C1-C12全氟亚烷基。
在一些实例中,根据本发明的嵌段共聚物由式II至式IV中的任一个表示:
其中R1至R4、R6、R10、R11、R14、m和n各自如上文对于式I所定义。
在一些实施方案中,R4是C1-C12亚烷基,优选C1-C6亚烷基,更优选亚正己基(-(CH2)6-)。在一些实施方案中,R6和R11各自独立地为C1-C20全氟亚烷基,优选C1-C12全氟亚烷基,更优选六氟亚异丙基(-C(CF3)2-)。在一些实施方案中,R10是C1-C12亚烷基,优选C1-C6亚烷基,更优选亚甲基(-CH2-)。
在一些实施方案中,根据本发明的嵌段共聚物通过GPC测量的数均分子量(Mn)为约2,000至约1,000,000道尔顿,优选约10,000至约500,000道尔顿,更优选约15,000至约300,000道尔顿。
在一些实施方案中,根据本发明的嵌段共聚物具有约1.1至约2.0,优选约1.2至约1.6的多分散指数(PDI)。
在一些实施方案中,根据本发明的嵌段共聚物是固体粉末或松散固体(bulksolid)的形式。在一些实施方案中,共聚物是白色的。
在一些实施方案中,嵌段共聚物的官能度为约1.0至约2.0。共聚物的官能度是指嵌段共聚物主链中不饱和双键的数量。
(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙
烯酸酯共聚物的制备方法
在另一方面,本发明提供制备根据本发明的(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物的方法,其包括:
-根据方案1,使二胺、二酐和单胺反应以形成聚酰胺酸(polyamic acid);
-使所述聚酰亚胺酸(polyimic acid)脱水以形成聚酰亚胺;
-使所述聚酰亚胺与(甲基)丙烯酸酯反应,以形成溴封端的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物,其由式V表示:
以及
-使所述溴封端的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物与(甲基)丙烯酸反应,以形成由式I表示的(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物,
其中R1至R5、R14、A、m和n各自具有与对于式I所述相同的定义和优选范围。
在一些实施方案中,(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物通过单电子转移-活性自由基聚合(SET-LRP反应)来合成。通过调节二酐单体与(甲基)丙烯酸酯单体的进料比,可以控制聚酰亚胺嵌段与聚(甲基)丙烯酸酯嵌段的数量比和整个共聚物的链长。此外,通过SET-LRP反应,(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物中的聚(甲基)丙烯酸酯部分的PDI可以被精确地控制为约1.01至约1.2,优选约1.05至约1.1。
可光固化粘合剂组合物
在另一方面,本发明提供包含根据本发明的共聚物的可光固化粘合剂组合物,其中粘合剂组合物优选为液体光学透明粘合剂组合物。
除了(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物之外,粘合剂组合物还包含(甲基)丙烯酸酯单体和/或光引发剂。
在一些实施方案中,(甲基)丙烯酸酯单体是单官能或双官能的。
在一些实施方案中,(甲基)丙烯酸酯单体包括但不限于丙烯酸2-羟基乙酯、(甲基)丙烯酸2-羟基丙酯、(甲基)丙烯酸4-羟基丁酯、(甲基)丙烯酸2-羟基丁酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸异辛酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸2-甲氧基乙酯、丁氧基乙二醇(甲基)丙烯酸酯、(甲基)丙烯酸2-乙氧基乙酯、(甲基)丙烯酸四氢糠酯、(甲基)丙烯酸苄酯、乙基卡必醇(甲基)丙烯酸酯、(甲基)丙烯酸苯氧基乙酯、羧甲基二乙二醇(甲基)丙烯酸酯、苯氧基聚乙二醇(甲基)丙烯酸酯、甲氧基聚乙二醇(甲基)丙烯酸酯、(甲基)丙烯酸2,2,2-三氟乙酯、2,2,3,3-四氟(甲基)丙烯酸酯、(甲基)丙烯酸1H,1H,5H-八氟戊酯、(甲基)丙烯酸酰亚胺酯、(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸异壬酯、(甲基)丙烯酸异肉豆蔻酯、(甲基)丙烯酸2-丁氧基乙酯、(甲基)丙烯酸2-苯氧基乙酯、(甲基)丙烯酸二环戊烯酯、(甲基)丙烯酸异癸酯、(甲基)丙烯酸二乙基氨基乙酯、(甲基)丙烯酸二甲基氨基乙酯、2-(甲基)丙烯酰氧基乙基六氢邻苯二甲酸、2-(甲基)丙烯酰氧基乙基2-羟基丙基邻苯二甲酸酯、(甲基)丙烯酸缩水甘油酯、2-(甲基)丙烯酰氧基乙基磷酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,3-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、1,10-癸二醇二(甲基)丙烯酸酯、2-正丁基-2-乙基-1,3-丙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、三丙二醇二(甲基)丙烯酸酯、聚丙二醇(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、环氧丙烷加成双酚A二(甲基)丙烯酸酯、环氧乙烷加成双酚A二(甲基)丙烯酸酯、环氧乙烷加成双酚F二(甲基)丙烯酸酯、(甲基)丙烯酸环戊二烯二硬脂酸酯、1,3-丁二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、环氧乙烷改性异氰尿酸二(甲基)丙烯酸酯、碳酸酯二醇二(甲基)丙烯酸酯等。市售(甲基)丙烯酸酯单体的实例包括例如EB230、EB264、EB265、EB284、EB280、EB1290、EB270、EB4833、EB8210、EB8402、EB8808(脂族氨基甲酸酯丙烯酸酯)、EB220、EB4827、EB4849(芳族氨基甲酸酯丙烯酸酯)、EB657、EB885、EB600、EB3200、EB3700、EB3702、EB3703、EB3720(Daicel Cytec Co.,Ltd.);CN8000NS、CN8001NS、CN8003、CN9001NS、CN9002、CN9014NS、CN991NS(氨基甲酸酯丙烯酸酯)、CN146、CN2203NS、CN2254NS、CN2261、CN2302、CN293、CN3108、CN704、CN8200(聚酯丙烯酸酯)、CN104NS、CN120NS、CN131NS、CN2003NS、CN159(环氧丙烯酸酯,可从Sartomer获得)等。
在一些实施方案中,光引发剂选自苯偶姻醚光引发剂、苯偶酰缩酮光引发剂、苯乙酮光引发剂、蒽醌光引发剂、噻吨酮光引发剂、二苯甲酮光引发剂、酰基氧化膦光引发剂、苯甲酸酯光引发剂及其任何组合。
在一些实施方案中,粘合剂组合物还包含任选存在的添加剂。对组合物中可包含的其它任选存在的添加剂没有具体限制,可以使用粘合剂中常用的添加剂。在一些实施方案中,其它任选存在的添加剂可包括但不限于热塑性聚合物、有机或无机填料、触变剂、硅烷偶联剂、稀释剂、改性剂、着色剂例如颜料和染料、表面活性剂、防腐剂、稳定剂、增塑剂、润滑剂、消泡剂、流平剂等。特别地,粘合剂组合物优选包含有机或无机填料和/或触变剂。
填料包括但不限于无机填料,例如二氧化硅、硅藻土、氧化铝、氧化锌、铁氧化物、氧化镁、锡氧化物、钛氧化物、氢氧化镁、氢氧化铝、碳酸镁、硫酸钡、石膏、硅酸钙、滑石、玻璃珠、绢云母活化的白土、膨润土、氮化铝、氮化硅等;以及有机填料,例如聚甲基丙烯酸甲酯、聚甲基丙烯酸乙酯、聚甲基丙烯酸丙酯、聚甲基丙烯酸丁酯、丙烯酸丁酯-甲基丙烯酸-甲基丙烯酸甲酯共聚物、聚丙烯腈、聚苯乙烯、聚丁二烯、聚戊二烯、聚异戊二烯、聚异丙烯等。这些填料可以单独使用或组合使用。
触变剂包括但不限于滑石、热解法二氧化硅、超细表面处理的碳酸钙、细颗粒氧化铝、板状氧化铝;层状化合物,例如蒙脱石;针状化合物,例如硼酸铝晶须等。其中,优选滑石、热解法二氧化硅和细颗粒氧化铝。
在另一方面,本发明提供根据本发明的粘合剂组合物在粘合基材中的用途,其中基材优选为玻璃或透明塑料。
在一些实施方案中,粘合基材的方法包括:
-将本发明的粘合剂组合物施加到一个基材的表面上;
-使其上施加有粘合剂组合物的基材与另外的基材接触;和
-将经粘结的基材暴露于光化辐射下。
粘合剂组合物可在暴露于光化辐射例如紫外线、可见光或黑光辐射后固化。在一个优选实施方案中,使用波长为约200nm至约450nm,优选约300nm至约450nm的紫外线辐射来使组合物固化。在另一优选实施方案中,施加到组合物的紫外线辐射具有约100mJ/cm2至约10,000mJ/cm2,优选约500mJ/cm2至约5,000mJ/cm2的辐射能量。优选地,辐射源在固化期间基本上垂直于基材。
实施例
以下实施例旨在帮助本领域技术人员更好地理解和实践本公开。本公开的范围不受实施例的限制,而是由所附权利要求限定。
实施例1(Ex.1)
2-溴-2-甲基丙酸6-氨基己基酯的盐酸盐的合成
在室温下,将6-羟基己烷-1-氯化铵(1.4g,13.7mmol)溶解在100mL三颈圆底烧瓶中的10mL无水丙酮中,向其中滴加2-溴异丁酰溴(1.7mL,13.7mmol)在10mL丙酮中的溶液。将混合物搅拌5小时后,通过旋转蒸发器从混合物中除去溶剂。所得产物在冷乙醚中沉淀并过滤。然后,在室温下真空干燥(2.07g,50%产率)。
1H NMR(CDCl3,300MHz):7.99[s,3H,NH3],4.178(t,2H,CH2O),3.08(m,2H,CH2N),1.79[s,6H,(CH3)2],1.74(m,2H,CH2),1.74(五重峰,2H,CH2),1.68[m,4H,(CH2)2]
聚酰胺酸1的合成
在室温下,将2,2-双(4-氨基苯基)六氟丙烷(6.68g,20mmol)、2-溴-2-甲基丙酸6-氨基己基酯的盐酸盐(0.60g,2mmol)溶解在500mL三颈圆底烧瓶中的150mL N-甲基-2-吡咯烷酮(NMP)中。然后,历时约0.5小时,向圆底烧瓶中滴加在100mL NMP中的4,4'-(六氟亚异丙基)二邻苯二甲酸酐(9.05g,2.04mmol)。酸酐完全加入后,将温度升至80℃。然后获得含有聚酰胺酸1的混合物。
聚酰胺1的合成
历时约1小时,将乙酸酐(Ac2O,7.55mL,80mmol)和三乙胺(TEA,11mL,80mmol)滴加到含有聚酰亚胺酸1的500mL三颈圆底烧瓶中。然后反应持续6小时,在此期间温度降至室温。将溶液倒入1L冰水中,沉淀出白色固体。然后,将白色固体用EtOH/H2O(1:3,体积比)洗涤三次,并在真空烘箱(LS-VO50,Labserv)中干燥。然后获得14.03g聚酰亚胺1。通过GPC测量的聚酰亚胺1的数均分子量(Mn)为5,400Da,通过GPC(Waters,1515)测量的多分散指数(PDI)为1.2。
IR(cm-1):2957(w),2928(w),1788(w),1722(vs),1608(w),1508(m),1373(vs),1254(s)1208(s),1175(vs)。
溴封端的嵌段共聚物1的合成
在室温下,将获得的聚酰亚胺1(2.0g)溶解在250mL三颈圆底烧瓶中的20mL二甲基亚砜(DMSO)中。向三颈圆底烧瓶中加入Cu网(0.2g)、40mL甲基丙烯酸甲酯(MMA)、20mL四氢呋喃(THF)。然后,将氮气吹扫引入三颈圆底烧瓶中,以置换其中的氧气。然后向三颈圆底烧瓶中加入2,2'-联吡啶(0.1g,aldrich),并且反应在60℃进行5小时。烧瓶中溶液的粘度大大增加。反应结束后,使溶液在MeOH中沉淀,获得白色固体粉末形式的产物,其为溴封端的嵌段共聚物1(Mn=250,000Da,PDI=1.3,GPC,Waters,1515)。
1H-NMR(CDCl3):8.07(1H),8.00(1H),7.89(1H),7.58(2H),7.53(2H),3.60(33H),2.06-1.81(20H),1.59(4H),1.43(2H),1.01(11H),0.84(21H)。
丙烯酸酯官能化的嵌段共聚物1的合成
将溴封端的嵌段共聚物1(2.0g)、K2CO3(0.5g,3.6mmol)、丙烯酸(0.25g,3.4mmol)和TBAB(0.1g,0.3mmol)溶解在250mL三颈圆底烧瓶中的100mL乙腈中。反应在N2的保护下,在70℃进行8小时。反应结束后,使溶液在室温下在100mL H2O中沉淀,获得白色粉末形式的产物。离子色谱测试(Varian 710-OES)显示产物的官能度(双键)为1.6。通过GPC(Waters,1515)测量的多分散指数(PDI)为1.3,Mn为250,000Da。
实施例2
聚酰亚胺2的合成
将4,4'-亚甲基双(2-甲基环己胺)(4.76g,20mmol)、2-溴-2-甲基丙酸6-氨基己基酯的盐酸盐(0.60g,2mmol)溶解在500mL圆瓶中的150mL NMP中。历时约0.5小时,向反应体系中加入100mL NMP中的4,4'-(六氟亚异丙基)二邻苯二甲酸酐(9.05g,20mmol)、三乙胺(0.1mL)。反应在室温下进行。酸酐完全加入后,将温度升至80℃。反应再持续3小时。然后,历时约1小时向体系中滴加Ac2O(7.55mL,80mmol)和TEA(11mL,80mmol)。反应持续6小时,并且温度降至室温。将溶液倒入1L冰水中。使获得的白色固体沉淀。然后用EtOH/H2O(1:3)洗涤三次,在真空烘箱中干燥后获得最终产物(聚酰亚胺2)。通过GPC测量的分子量(Mn)为5,800Da,PDI为1.26。
溴封端的嵌段共聚物2的合成
将聚酰亚胺2(2.0g)溶解在250mL瓶中的20mL DMSO中。向体系中加入Cu网(0.2g)、10mL MMA、20mL THF。然后将N2吹扫到体系中,以避免O2的抑制。然后向溶液中加入2,2'-联吡啶(0.1g),并且反应在60℃进行5小时。反应结束后,使溶液在MeOH中沉淀,获得作为溴封端的嵌段共聚物2的树脂。GPC显示分子量(Mn)约为138,000Da。
丙烯酸酯官能化的嵌段共聚物2的合成
除了使用溴封端的嵌段共聚物2代替溴封端的嵌段共聚物1之外,以与上文对于实施例1所述相同的方式来制备嵌段共聚物2。
聚合物显示分子量为138,000道尔顿,PDI为1.6(Waters,1515)。官能度为约1.6。
实施例3
聚酰亚胺3的合成
将4,4'-亚甲基双(2-甲基环己胺)(9.52g,40mmol)、2-溴-2-甲基丙酸6-氨基己基酯的盐酸盐(1.20g,4mmol)溶解在500mL圆瓶中的150mL NMP中。历时约0.5小时,向反应体系中加入在100mL NMP中的1,2,4,5-环己烷四甲酸二酐(9.13g,40mmol)、TEA(0.1mL)。反应在80℃进行。酸酐完全加入后,反应再持续3小时。然后,历时约1小时向体系中滴加Ac2O(15.1mL,160mmol)和TEA(22mL,160mmol)。反应再进行6小时。然后将溶液倒入2L冰水中。沉淀出白色固体。然后用EtOH/H2O(1:3)洗涤三次,在真空烘箱中干燥后获得产物(聚酰亚胺3)。
溴封端的嵌段共聚物3的合成
将聚酰亚胺3(2.0g)溶解在250mL瓶中的20mL DMSO中。向体系中加入Cu网(0.2g)、20mL MMA、20mL THF。然后将N2吹扫到体系中,以避免O2的抑制。然后向溶液中加入2,2'-联吡啶(0.1g),并且反应在60℃进行5小时。反应结束后,用二氯甲烷(200mL)稀释溶液。然后加入100mL水,浓缩有机层,获得作为溴封端的嵌段共聚物3的树脂(Mn=16,500Da,PDI=1.5)。
丙烯酸酯官能化的嵌段共聚物3的合成
除了使用溴封端的嵌段共聚物3代替溴封端的嵌段共聚物1之外,以与上文对于实施例1所述相同的方式来制备嵌段共聚物3。
官能度为约1.6,Mn=16,500Da,PDI=1.5。
性能测量
实施例4-13
丙烯酸酯官能化的嵌段共聚物1的溶解度测试
将丙烯酸酯官能化的嵌段共聚物1(单位:mg)与下面列出的丙烯酸酯单体和/或低聚物(单位:mg)混合。然后,将混合物用快速混合器(Flacktek,DAC150,2500rpm)搅拌3分钟。用肉眼观察获得的混合物,以查看是形成了透明溶液,还是不期望地形成分离相或分散体。
注释:
1:氨基甲酸酯丙烯酸酯13-275可从Sartomer获得;
2:聚乙二醇-二丙烯酸酯可从Sartomer获得;
3:甲基丙烯酸甲氧基乙酯可从KPX获得;以及
4:丙烯酸2-羟基乙酯可从Aldrich获得。
从上表可以看出,丙烯酸酯官能化的嵌段共聚物1可溶于各种(甲基)丙烯酸酯单体及它们的混合物。
实施例14
丙烯酸酯官能化的嵌段共聚物1-3以及参比样品的透光率测试
在室温下,将2-溴-2-甲基丙酸6-氨基己基酯的盐酸盐(0.2g)溶解在250mL三颈圆底烧瓶中的20mL二甲基亚砜(DMSO)中。向三颈圆底烧瓶中加入Cu网(0.2g)、40mL甲基丙烯酸甲酯(MMA)和20mL四氢呋喃(THF)。然后,将氮气吹扫引入三颈圆底烧瓶中,以置换其中的氧气。然后向三颈圆底烧瓶中加入2,2'-联吡啶(0.1g,aldrich),并且反应在60℃进行5小时。烧瓶中溶液的粘度大大增加。反应结束后,使溶液在MeOH中沉淀,获得白色固体产物,其为聚甲基丙烯酸甲酯PMMA(Mn=150,000Da,PDI=1.1,GPC,Waters,1515)。1H-NMR(CDCl3):3.60(s,3H),2.06-1.81(m,2H),1.01(s,1H),0.84(s,2H)。
将丙烯酸酯官能化的嵌段共聚物1-3以及上述PMMA分别溶解在THF(10mg/mL)中。图1显示了用L-650(可从Perkin Elmer获得)收集的UV-Vis透射-波长图。
从图1可以看出,在近可见光区,根据本发明的甲基丙烯酸酯官能化的嵌段共聚物1-3显示出高的透光率,其几乎与聚甲基丙烯酸甲酯的透光率相同。
实施例15
丙烯酸酯官能化的嵌段共聚物1-3以及参比样品的热稳定性测试
丙烯酸酯官能化的嵌段共聚物1-3(10g)以及上述PMMA(10g)的热稳定性在Q500(可从TA获得)中进行测试。将氮气引入Q500中。Q500中的温度以10℃/分钟的速率升高。
图2结合了丙烯酸酯官能化的嵌段共聚物1-3以及上述PMMA的热重分析(TGA)曲线。图3-6各自显示了丙烯酸酯官能化的嵌段共聚物1、2、3和聚甲基丙烯酸甲酯的热重分析(TGA)曲线。
从图2-6可以看出,丙烯酸酯官能化的嵌段共聚物1-3表现出比聚甲基丙烯酸甲酯更好的热稳定性。共聚物1和共聚物3的Td5温度(5重量%分解的温度)高于PMMA的Td5温度。在第一阶段,PMMA剧烈分解,在329.81℃分解率达到21.93重量%。相比之下,根据本发明的丙烯酸酯官能化的嵌段共聚物1-3在第一阶段稳定得多。
Claims (14)
1.(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物,其由式I表示:
在式(I)中,m和n各自独立地表示约1至约50的整数,条件是m和n不同时为1;
R1和R14彼此相同或不同,独立地为氢或甲基;
R2选自C1-C12烷基;
R3是-CH(CH3)-或-C(CH3)2-;
R4选自C1-C12亚烷基;
R5表示选自C6-C30脂环族基团和C6-C30亚芳基的二价连接单元;并且
A表示选自C4-C14脂族基团、C4-C30脂环族基团、C6-C30芳基、醚基、砜基、硫醚基、酰胺基和酯基的四价连接单元。
2.根据权利要求1所述的共聚物,其中R2选自C1-C6烷基。
3.根据权利要求1或2所述的共聚物,其中R4选自C1-C6亚烷基。
4.根据前述权利要求中任一项所述的共聚物,其中A选自以下基团:
其中R6是二价连接单元,优选地,R6位于苯环的3,3'-、3,4'-、4,3'-或4,4'-位置,
更优选地,R6选自-O-、-S-、-C(O)-、-SO2-、-SO-、C1-C20亚烷基、卤代C1-C20亚烷基(包括C1-C20全氟亚烷基)和由-O-Z-O-表示的基团,其中Z是选自以下基团的二价连接基团:
其中R7选自-O-、-S-、-C(O)-、-SO2-、-SO-、C1-C20亚烷基和卤代C1-C20亚烷基(包括C1-C20全氟亚烷基)。
5.根据前述权利要求中任一项所述的共聚物,其中R5选自以下基团:
其中R8至R13各自独立地选自C1-C20亚烷基及其卤代衍生物,包括C1-C20全氟亚烷基。
6.根据前述权利要求中任一项所述的共聚物,其中所述共聚物由式II至式IV中的任一个表示:
其中R1至R4、R6、R10、R11、R14、m和n各自如权利要求1-5中任一项所定义。
7.根据前述权利要求中任一项所述的共聚物,其通过GPC测量的数均分子量Mn为2,000-1,000,000道尔顿,优选10,000-500,000道尔顿,更优选15,000-300,000道尔顿。
8.根据前述权利要求中任一项所述的共聚物,其中所述聚酰亚胺嵌段与所述聚(甲基)丙烯酸酯嵌段的数量比,即m:2n,为1:1至1:100。
9.制备根据权利要求1-8中任一项所述的(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物的方法,其包括:
-根据方案1,使二胺、二酐和单胺反应以形成聚酰胺酸;
-使所述聚酰亚胺酸脱水以形成聚酰亚胺;
-使所述聚酰亚胺与(甲基)丙烯酸酯反应,以形成溴封端的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物,其由式V表示:
以及
-使所述溴封端的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物与(甲基)丙烯酸反应,以形成由式I表示的(甲基)丙烯酸酯官能化的聚(甲基)丙烯酸酯-嵌段-聚酰亚胺-嵌段-聚(甲基)丙烯酸酯共聚物,
其中R1至R5、R14、A、m和n各自如权利要求1-4中任一项所定义。
10.包含根据权利要求1-8中任一项所述的共聚物的可光固化粘合剂组合物,其中所述粘合剂组合物优选为液体光学透明粘合剂。
11.根据权利要求10所述的粘合剂组合物,其进一步包含(甲基)丙烯酸酯单体和/或光引发剂。
12.根据权利要求11所述的粘合剂组合物,其中所述(甲基)丙烯酸酯单体是单官能或双官能的。
13.根据权利要求11或12所述的粘合剂组合物,其中所述光引发剂选自苯偶姻醚光引发剂、苯偶酰缩酮光引发剂、苯乙酮光引发剂、蒽醌光引发剂、噻吨酮光引发剂、二苯甲酮光引发剂、酰基氧化膦光引发剂和苯甲酸酯光引发剂以及它们的任意组合。
14.根据权利要求10-13中任一项所述的粘合剂组合物在粘合基材中的用途,其中所述基材优选为玻璃或透明塑料。
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CN117089315A (zh) * | 2023-10-19 | 2023-11-21 | 宁波长阳科技股份有限公司 | 一种水性锂电池聚酰亚胺粘合剂及制备方法、锂电池极片 |
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03167226A (ja) * | 1989-11-28 | 1991-07-19 | Mitsubishi Rayon Co Ltd | ブロック共重合体 |
JP2002341535A (ja) * | 2001-05-14 | 2002-11-27 | Hitachi Cable Ltd | 感光性ポリイミド樹脂組成物 |
CN101466751A (zh) * | 2006-07-28 | 2009-06-24 | 赢创罗姆有限责任公司 | 制备基于(甲基)丙烯酸酯的aba-三嵌段共聚物的方法 |
CN103122086A (zh) * | 2005-09-21 | 2013-05-29 | 西巴特殊化学品控股有限公司 | 具有改进可加工性的填充橡胶配混物 |
CN103289593A (zh) * | 2013-04-23 | 2013-09-11 | 深圳丹邦科技股份有限公司 | 一种用于cof的耐高温压敏胶膜及其制备方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5885708A (en) | 1997-02-14 | 1999-03-23 | Minnesota Mining And Manufacturing Company | Antistatic latex adhesives |
JP4171898B2 (ja) | 2003-04-25 | 2008-10-29 | 信越化学工業株式会社 | ダイシング・ダイボンド用接着テープ |
MY143349A (en) | 2004-11-12 | 2011-04-29 | Mitsui Chemicals Inc | Film adhesive and semiconductor package using the same |
JP5508262B2 (ja) * | 2007-07-26 | 2014-05-28 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン | イミド部分を含有するアルコールおよびそれから製造される反応性オリゴマー |
EP2188622A2 (en) | 2007-09-13 | 2010-05-26 | 3M Innovative Properties Company | Low temperature bonding electronic adhesives |
JP5443784B2 (ja) | 2009-02-27 | 2014-03-19 | リンテック株式会社 | 多孔質ポリイミド形成用ブロック共重合体、多孔質ポリイミドおよび絶縁材料 |
CN103122068B (zh) * | 2012-12-25 | 2015-07-08 | 中山大学 | 一种uv涂料用聚酰亚胺丙烯酸酯低聚物 |
KR101966736B1 (ko) * | 2015-09-15 | 2019-04-09 | 주식회사 엘지화학 | 변성 폴리이미드 및 이를 포함하는 경화성 수지 조성물 |
EP3358408B1 (en) * | 2015-09-28 | 2019-06-19 | FUJIFILM Corporation | Negative-type photosensitive resin composition, negative-type lithographic printing original plate, and method for producing lithographic printing plate |
-
2017
- 2017-04-21 KR KR1020197034292A patent/KR102408266B1/ko active IP Right Grant
- 2017-04-21 MX MX2019012405A patent/MX2019012405A/es unknown
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-
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Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03167226A (ja) * | 1989-11-28 | 1991-07-19 | Mitsubishi Rayon Co Ltd | ブロック共重合体 |
JP2002341535A (ja) * | 2001-05-14 | 2002-11-27 | Hitachi Cable Ltd | 感光性ポリイミド樹脂組成物 |
CN103122086A (zh) * | 2005-09-21 | 2013-05-29 | 西巴特殊化学品控股有限公司 | 具有改进可加工性的填充橡胶配混物 |
CN101466751A (zh) * | 2006-07-28 | 2009-06-24 | 赢创罗姆有限责任公司 | 制备基于(甲基)丙烯酸酯的aba-三嵌段共聚物的方法 |
CN103289593A (zh) * | 2013-04-23 | 2013-09-11 | 深圳丹邦科技股份有限公司 | 一种用于cof的耐高温压敏胶膜及其制备方法 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN117089315A (zh) * | 2023-10-19 | 2023-11-21 | 宁波长阳科技股份有限公司 | 一种水性锂电池聚酰亚胺粘合剂及制备方法、锂电池极片 |
CN117089315B (zh) * | 2023-10-19 | 2024-02-09 | 宁波长阳科技股份有限公司 | 一种水性锂电池聚酰亚胺粘合剂及制备方法、锂电池极片 |
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