TWI737623B - 可固化之苯并組合物 - Google Patents
可固化之苯并組合物 Download PDFInfo
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- TWI737623B TWI737623B TW105123326A TW105123326A TWI737623B TW I737623 B TWI737623 B TW I737623B TW 105123326 A TW105123326 A TW 105123326A TW 105123326 A TW105123326 A TW 105123326A TW I737623 B TWI737623 B TW I737623B
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- curable composition
- substituted
- unsubstituted
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- alkyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 102
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000003085 diluting agent Substances 0.000 claims abstract description 37
- 229920001721 polyimide Polymers 0.000 claims abstract description 31
- 239000004642 Polyimide Substances 0.000 claims abstract description 30
- 125000005605 benzo group Chemical group 0.000 claims description 48
- -1 phenyl indanyl Chemical group 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000000835 fiber Substances 0.000 claims description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000004593 Epoxy Substances 0.000 claims description 12
- 239000012456 homogeneous solution Substances 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 11
- 230000009477 glass transition Effects 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000012745 toughening agent Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- VNAFWALXWOAPCK-UHFFFAOYSA-N 1-phenyl-2,3-dihydro-1h-indene Chemical group C1CC2=CC=CC=C2C1C1=CC=CC=C1 VNAFWALXWOAPCK-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 239000007970 homogeneous dispersion Substances 0.000 claims description 4
- 150000002466 imines Chemical group 0.000 claims description 4
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- 239000003063 flame retardant Substances 0.000 claims description 3
- 238000007654 immersion Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000012744 reinforcing agent Substances 0.000 claims description 3
- 239000013008 thixotropic agent Substances 0.000 claims description 3
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 claims description 2
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 claims description 2
- GSIWIEKVNXWKLE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-4-carbaldehyde Chemical compound C1C(C=O)CCC2OC21 GSIWIEKVNXWKLE-UHFFFAOYSA-N 0.000 claims description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- BQQUFAMSJAKLNB-UHFFFAOYSA-N dicyclopentadiene diepoxide Chemical compound C12C(C3OC33)CC3C2CC2C1O2 BQQUFAMSJAKLNB-UHFFFAOYSA-N 0.000 claims description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 2
- 230000004584 weight gain Effects 0.000 claims description 2
- 235000019786 weight gain Nutrition 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- WCNSACYQLDNHFD-UHFFFAOYSA-N 4-(1,3,3-trimethyl-1,2-dihydroinden-2-yl)aniline Chemical compound NC1=CC=C(C=C1)C1C(C2=CC=CC=C2C1C)(C)C WCNSACYQLDNHFD-UHFFFAOYSA-N 0.000 claims 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 claims 1
- ADAHGVUHKDNLEB-UHFFFAOYSA-N Bis(2,3-epoxycyclopentyl)ether Chemical compound C1CC2OC2C1OC1CCC2OC21 ADAHGVUHKDNLEB-UHFFFAOYSA-N 0.000 claims 1
- NIYNIOYNNFXGFN-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol;7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound OCC1CCC(CO)CC1.C1C(C(=O)O)CCC2OC21.C1C(C(=O)O)CCC2OC21 NIYNIOYNNFXGFN-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000002009 alkene group Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 7
- 239000002131 composite material Substances 0.000 abstract description 7
- 239000000126 substance Substances 0.000 abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 39
- 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 description 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 17
- 239000011521 glass Substances 0.000 description 17
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 14
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 229960003742 phenol Drugs 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 8
- 229920000647 polyepoxide Polymers 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000565 sealant Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 241001598984 Bromius obscurus Species 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
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- 229920001971 elastomer Polymers 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- 238000009835 boiling Methods 0.000 description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
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- 125000006159 dianhydride group Chemical group 0.000 description 3
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
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- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 3
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 2
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- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 2
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- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 2
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
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- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 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 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/16—Derivatives of isocyanic acid having isocyanate groups acylated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
本發明提供一種可固化組合物，其含有苯并
Description
不適用。
不適用。
本發明係關於一種可固化組合物，其含有苯并
、反應性稀釋劑及可溶性聚醯亞胺。可固化組合物可用於多種應用中，諸如用於電子組件及電組件之黏著劑、密封劑、塗層、結構性或非結構性複合材料及封裝系統中。
衍生自苯并
開環聚合之聚合物在各種應用中與酚系樹脂、環氧樹脂及其他熱固性或熱塑性樹脂競爭，例如在預浸體、積層板、印刷線路板(PWB)、模製原料、密封劑、燒結粉、澆築物、結構性複合材料及電組件中。藉由在溶劑存在或不存在下使苯酚與胺及醛反應所合成之苯并
一經固化，即顯示為尺寸穩定且具有良好的電阻及機械阻力、低收縮性、低吸水性，且具有中等玻璃轉化溫度至高玻璃轉化溫度。
苯并
亦與各種環氧樹脂組合來產生可固化組合物(參見例如美國專利第4,607,091號(Schreiber)、第5,021,484號(Schreiber)、第5,200,452號(Schreiber)及第5,443,911號(Schreiber))。因為環氧樹脂可
降低苯并
之熔融黏度，所以已顯示此等摻合物適用於電器應用，因為其能夠處理較高填充劑負載量同時仍保持可處理黏度。然而，使用此類摻合物之一個缺點為通常需要較高固化溫度。此外，儘管此等摻合物在固化之後呈現高玻璃轉化溫度，但通常會在一定程度上犧牲韌性及硬度。
最近，已添加增韌劑來改善可撓性。舉例而言，WO 2014/137717(Wang等人)揭示基於聚碸之增韌劑用於基於苯并
之組合物的用途；WO 2010/031826(Kreiling等人)揭示含有苯并
化合物及酚(較佳為雙酚A)封端預聚物增韌劑之可固化組合物；EP 1639038B1(Lei等人)揭示含有苯并
及丙烯腈-丁二烯共聚物增韌劑之可固化組合物；WO 2009/075746(Taden等人)教示可固化組合物，其包括苯并
及含有至少3個苯并
環及至少一個脂族、雜脂族、芳脂族、雜芳脂族、芳族或雜芳族軟片段之苯并
大分子單體增韌劑。WO 2009/075744(Kreiling等人)教示基於苯并
及基於非苯并
之韌化添加劑用於苯并
質樹脂組分之用途。WO 2007/064801揭示一種組合物，其含有苯并
及兩種加合物增韌劑之組合：第一種由含羥基化合物、含異氰酸酯化合物及酚化合物製備；且第二種由第一加合物及含環氧基化合物及第二酚化合物製備；WO 2012/015604(Tran)揭示苯并
組分及酚封端之聚胺基甲酸酯、聚脲或聚脲-胺基甲酸酯；且WO 2012/100980(Cross等人)教示一種組合物，其包含苯并
組分、含芳基碸之苯并
組分及聚醚碸以便獲得均質可混溶摻合物。
儘管目前先進技術如此，本發明之目標為提供一種含有韌化劑的經改良之基於苯并
之組合物，其一經固化，即能夠長時間在高溫下以熱方式、機械方式及物理方式起效且不犧牲玻璃轉化溫度、強度、韌性或水解穩定性特性，因此其可在各種行業(諸如航空、電子
及汽車行業)內適用於高溫應用中。
本發明提供一種可固化組合物，其包括苯并
、反應性稀釋劑及可溶性聚醯亞胺。在一個實施例中，可固化組合物一經固化，即形成具有大於180℃之玻璃轉化溫度的物品。在另一實施例中，可固化組合物一經固化，即形成具有大於200J/m2之斷裂韌性的物品，而在又一實施例中，可固化組合物一經固化，即形成具有大於4000MPa之乾式撓曲模數的物品。
本發明之可固化組合物可用於各種應用中，諸如塗層、黏著劑、密封劑及結構性或非結構性複合材料，且因此可用於各種行業中，例如航空、汽車或電子行業。
若術語「包含」及其衍生詞在本文中出現，則其不意欲排除任何其他組分、步驟或程序之存在，無論該組分、步驟或程序是否揭示於本文中。為避免懷疑，除非相反地指出，否則本文中所有經由使用術語「包含」主張的組合物可包括任何其他添加劑、佐劑或化合物。相比而言，若術語「基本上由……組成」出現在本文中，則其自任何隨後列舉之範圍中排除任何其他組分、步驟或程序(對可操作性而言並非必需的彼等組分、步驟或程序除外)，且若使用術語「由……組成」，則其排除任何非具體描述或列舉之組分、步驟或程序。除非另行說明，否則術語「或」係指個別地以及以任何組合形式列舉之成員。
本文使用冠詞「一(a/an)」指代該冠詞之語法對象中之一者或多於一者(亦即至少一者)。借助於實例，「一苯并
(a
benzoxazine)」意謂一個苯并
或多於一個苯并
。短語「在一個實施例中」、「根據一個實施例」及其類似者通常意謂該短語後接之具體特點、結構或特徵包括在本發明之至少一個實施例中，且可包括在本發明之多於一個實施例中。重要的是，此類短語未必指代同一個實施例。若本說明書指出「可(may/can/could/might)」包括一種組分或特點或具有一種特徵，則不必要包括該具體組分或特點或具有該特徵。
本發明提供一種可固化組合物，其含有苯并
、反應性稀釋劑及可溶性聚醯亞胺。已出人意料地發現此組分組合提供一種可固化組合物，其一經固化，即在諸如斷裂韌性、拉伸及撓曲模數、玻璃轉化溫度及水解穩定性之若干關鍵熱機械特性方面展現顯著改良。
根據一個實施例，可固化組合物含有苯并
。苯并
賦予組合物機械強度、低吸水性及熱可固化性，可為任何含有至少一個苯并
部分之可固化單體、寡聚物或聚合物。
因此，在一個實施例中，苯并
可由通式(1)表示：
其中b為1至4之整數；各R獨立地為氫、經取代或未經取代之C1-C20烷基、經取代或未經取代之C2-C20烯基、經取代或未經取代之C6-C20芳基、經取代或未經取代之C2-C20雜芳基、經取代或未經取代之C4-C20碳環基、經取代或未經取代之C2-C20雜環基或C3-C8環烷基；各R1獨立地為氫、C1-C20烷基、C2-C20烯基或C6-C20芳基；且Z為直接鍵(當b=2時)、經取代或未經取代之C1-C20烷基、經取代或未經取代之
C6-C20芳基、經取代或未經取代之C2-C20雜芳基、O、S、S=O、O=S=O或C=O。取代基包括(但不限於)羥基、C1-C20烷基、C2-C10烷氧基、巰基、C3-C8環烷基、C6-C14雜環基、C6-C14芳基、C6-C14雜芳基、鹵素、氰基、硝基、硝酮、胺基、醯胺基、醯基、氧基醯基、羧基、胺基甲酸酯、磺醯基、磺醯胺及硫醯基。
在式(1)之一特定實施例中，苯并
可由下式(1a)表示：
其中Z選自直接鍵、CH2、C(CH3)2、C=O、O、S、S=O、O=S=O及
；各R獨立地為氫、C1-C20烷基、烯丙基或C6-C14芳基；且R1如上文所定義。
在另一實施例中，苯并
可由以下通式(2)表示：
其中Y為C1-C20烷基、C2-C20烯基、或經取代或未經取代之苯基；且R2為氫、鹵素、C1-C20烷基或C2-C20烯基。苯基之適合取代基如上所述。
在式(2)之一特定實施例中，苯并
可由下式(2a)表示：
其中R2為氫、C1-C20烷基或C2-C20烯基(其中之每一者視情況由O、N、S、C=O、COOH及NHC=O中之一或多者取代或間雜)及C6-C20芳基；且R3為氫、C1-C20烷基或C2-C20烯基(其中之每一者視情況由O、N、S、C=O、COOH及NHC=O中之一或多者取代或間雜)或C6-C20芳基。
或者，苯并
可由以下通式表示：
其中p為2，W選自聯二苯、二苯甲烷、二苯異丙烷、二苯硫醚、二苯亞碸、二苯碸及二苯酮，且R1如上文所定義。
在本發明中，可使用多官能苯并
之組合、單官能苯并
之組合、或一或多種多官能苯并
及一或多種單官能苯并
之組合。
苯并
可購自若干來源，包括Huntsman Advanced Materials Americas LLC及Shikoku Chemicals Corporation。
亦可藉由在移除水之條件下使酚化合物(例如雙酚A、雙酚F、酚酞或硫二苯酚)與醛(例如甲醛)及一級胺反應來獲得苯并
。此進一步描述於美國專利第5,543,516號中，其內容以引用之方式併入本文中。酚化合物與醛反應物之莫耳比可為約1：3至1：10，或者約1：4至1：7。在另一實施例中，酚化合物與醛反應物之莫耳比可為約1：4.5至1：5。酚化合物與一級胺反應物之莫耳比可為約1：1至1：3，或者約1：1.4至1：2.5。在另一實施例中，酚化合物與一級胺反應物之莫耳比可為約1：2.1至1：2.2。
一級胺之實例包括：芳族單胺或二胺、脂族胺、環脂族胺及雜環單胺；例如苯胺、鄰苯二胺、間苯二胺及對苯二胺、聯苯胺、4,4'-二胺基二苯基甲烷、環己胺、丁胺、甲胺、己胺、烯丙胺、糠胺、乙二胺及丙二胺。胺在其各別碳部分中可經C1-C8烷基或烯丙基取代。在一個實施例中，一級胺為具有通式RaNH2之化合物，其中Ra為烯丙基、未經取代或經取代之苯基、未經取代或經取代之C1-C8烷基或未經取代或經取代之C3-C8環烷基。Ra基上之適合取代基包括(但不限於)胺基、C1-C4烷基及烯丙基。在一些實施例中，可在Ra基上存在一至四個取代基。在一個特定實施例中，Ra為苯基。
根據另一實施例，按可固化組合物之總重量計，苯并
可以介於約40重量%至約90重量%之範圍內的量包含於可固化組合物中。在另一實施例中，按可固化組合物之總重量計，苯并
可以介於約50重量%至約80重量%之範圍內的量包含於可固化組合物中。在另一實施例中，按可固化組合物之總重量計，苯并
可以大於約40重量%之量包含於可固化組合物中，而在其他實施例中大於約50重量%。在另一實施例中，按可固化組合物之總重量計，苯并
可以小於約90重量%之量包含於可固化組合物中，而在其他實施例中小於約80重量%。
根據另一實施例，可固化組合物含有反應性稀釋劑。如本文所使用之「反應性稀釋劑」包括完全可溶、具有反應性，且當與苯并
及可溶性聚醯亞胺組合時，能夠降低組合物之黏度的任何化合物。
在一個實施例中，反應性稀釋劑為環氧基反應性稀釋劑。環氧基反應性稀釋劑可為單環氧化物、二環氧化物或聚環氧化物，且進一步可為脂族、環脂族或芳族化合物。單環氧化物、二環氧化物或聚環氧化物可單獨使用或彼此混合使用。亦可藉由化學手段(例如藉由與二醇或二羧酸酐反應)預固化單環氧化物、二環氧化物或聚環氧化
物。
在另一實施例中，環氧基反應性稀釋劑可為縮水甘油基封端化合物，例如含有直接連接至氧原子、氮原子或硫原子之縮水甘油基或β-甲基縮水甘油基的化合物。此類環氧基反應性稀釋劑包括(但不限於)聚縮水甘油酯及聚(β-甲基縮水甘油酯)，其藉由在鹼存在下，使每分子含有兩個或多於兩個羧酸基之物質與表氯醇、甘油二氯醇或β-甲基表氯醇反應獲得。聚縮水甘油酯可衍生自脂族羧酸，例如草酸、丁二酸、己二酸、癸二酸、或二聚或三聚亞麻油酸；衍生自環脂族羧酸，諸如六氫鄰苯二甲酸、4-甲基六氫鄰苯二甲酸、四氫鄰苯二甲酸及4-甲基四氫鄰苯二甲酸；或衍生自芳族羧酸，諸如鄰苯二甲酸、間苯二甲酸及對苯二甲酸。
其他可使用之環氧基反應性稀釋劑包括聚縮水甘油醚及聚(β-甲基縮水甘油醚)，其藉由在鹼性條件下或替代性地在酸性觸媒存在下隨後用鹼處理，使每分子含有兩個或多於兩個醇羥基或兩個或多於兩個酚羥基之物質與表氯醇、甘油二氯醇或β-甲基表氯醇反應來獲得。此類聚縮水甘油醚可衍生自脂族醇，例如乙二醇及諸如二乙二醇及三乙二醇之聚(氧伸乙基)二醇、丙二醇及聚(氧伸丙基)二醇、丙-1,2-二醇、丙-1,3-二醇、丁-1,4-二醇、戊-1,5-二醇、己-1,6-二醇、己-2,4,6-三醇、甘油、1,1,1-三羥甲基丙烷及異戊四醇；衍生自環脂族醇，諸如對環己二醇、1,1-雙(羥甲基)環己-3-烯、雙(4-羥基環己基)甲烷、1,4-二羥甲基-環己烷及2,2-雙(4-羥基環己基)-丙烷；或衍生自含有芳族核之醇，諸如N,N-雙-(2-羥乙基)苯胺及4,4'-雙(2-羥乙基胺基)二苯基甲烷。在一個實施例中，聚縮水甘油醚衍生自每分子含有兩個或多於兩個酚羥基之物質，例如間苯二酚、兒茶酚、對苯二酚、雙(4-羥苯基)甲烷、1,1,2,2-肆(4-羥苯基)乙烷、4,4'-二羥基聯苯、雙(4-羥苯基)碸且尤其為酚醛樹脂或甲酚-甲醛酚醛清漆樹脂、2,2-雙(4-羥苯基)
丙烷(另外稱為雙酚A)及2,2-雙(3,5-二溴-4-羥苯基)-丙烷。
可進一步採用包括聚(N-縮水甘油基)化合物之環氧基反應性稀釋劑，其例如藉由對表氯醇及含有至少兩個直接連接至氮之氫原子的胺(諸如苯胺、正丁胺、雙(4-胺基苯基)甲烷、雙(4-胺基苯基)碸及雙(4-甲胺基苯基)甲烷)之反應產物進行去氯化氫來獲得。其他可使用之聚(N-縮水甘油基)化合物包括異氰尿酸三縮水甘油酯、環狀伸烷基脲(諸如乙烯脲及1,3-丙烯脲)之N,N'-二縮水甘油基衍生物，及內醯脲(諸如5,5-二甲基內醯脲)之N,N'-二縮水甘油基衍生物。
亦可採用藉由將環狀及丙烯酸聚烯烴環氧化所獲得之環氧基反應性稀釋劑，諸如乙烯基環己烯二氧化物、檸檬烯二氧化物、二環戊二烯二氧化物、3,4-環氧基二氫二環戊二烯基縮水甘油醚、乙二醇之雙(3,4-環氧基二氫二環戊二烯基)醚、3,4'-環氧基環己烷甲酸3,4-環氧基環己基甲酯或其6,6'-二甲基衍生物、乙二醇之雙(3,4-環氧基環己烷甲酸酯)、在3,4-環氧基環己烷甲醛與1,1-雙(羥甲基)-3,4-環氧基環己烷之間形成的縮醛、雙(2,3-環氧環戊基)醚、丁二烯二環氧化物、或丁二烯與烯系化合物(諸如苯乙烯及乙酸乙烯酯)之共聚物、環氧化亞麻油酸衍生物及環氧化聚丁二烯。
根據另一實施例，反應性稀釋劑可為甲基丙烯酸樹脂單體或預聚物，或單官能或多官能丙烯酸酯或甲基丙烯酸脂樹脂單體。實例包括含有乙烯基、丙烯酸酯、苯乙烯類、二烯、甲基丙烯酸脂、烯丙基、丙烯醯胺、甲基丙烯醯胺、丙烯腈及甲基丙烯腈之部分及其組合。代表實例包括苯乙烯、α-甲基苯乙烯、經取代之苯乙烯、乙烯酯、乙烯醚、環己基乙烯醚、N-乙烯基-2-吡咯啶酮、(甲基)丙烯醯胺、N上經取代之(甲基)丙烯醯胺、(甲基)丙烯酸辛酯、壬基苯酚乙氧基化(甲基)丙烯酸酯、(甲基)丙烯酸異壬酯、(甲基)丙烯酸異冰片酯、(甲基)丙烯酸2-(2-乙氧基乙氧基)乙酯、(甲基)丙烯酸2-乙基己
酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸β-羧基乙酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸2-羥乙酯、(甲基)丙烯腈、順丁烯二酸酐、衣康酸(itaconic acid)、(甲基)丙烯酸異癸酯、(甲基)丙烯酸十二烷酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸甲酯、(甲基)丙烯酸己酯、(甲基)丙烯酸、N-乙烯基己內醯胺、N-乙烯基甲醯胺、(甲基)丙烯酸硬脂酯、羥基官能性己內酯(甲基)丙烯酸酯、(甲基)丙烯酸異辛酯、(甲基)丙烯酸羥乙酯、(甲基)丙烯酸羥甲酯、(甲基)丙烯酸羥丙酯、(甲基)丙烯酸羥基異丙酯、(甲基)丙烯酸羥丁酯、(甲基)丙烯酸羥基異丁酯、(甲基)丙烯酸四氫呋喃酯及其組合。
在一個實施例中，反應性稀釋劑為單官能丙烯酸酯，例如丙烯酸2-(2-氧基)乙酯、丙烯酸2-苯氧基乙酯、丙烯酸羥乙酯、其他長鏈丙烯酸烷酯、丙烯酸異冰片酯、環狀三羥甲基丙烷縮甲醛丙烯酸酯、單官能脂族丙烯酸胺基甲酸酯及其組合。
在另一實施例中，反應性稀釋劑為聚丙烯酸酯。聚丙烯酸酯反應性稀釋劑之實例包括乙二醇二(甲基)丙烯酸酯、己二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、乙氧基化三羥甲基丙烷三(甲基)丙烯酸酯、甘油三(甲基)丙烯酸酯、異戊四醇三(甲基)丙烯酸酯、異戊四醇四(甲基)丙烯酸酯、參(2-羥基-乙基)異氰尿酸酯三丙烯酸酯雙三羥甲基丙烷四(甲基)丙烯酸酯及衍生自烷氧基化多元醇之二丙烯酸酯或聚丙烯酸酯，諸如丙氧基化新戊二醇二丙烯酸酯或丙氧基化乙二醇三丙烯酸酯、新戊二醇二(甲基)丙烯酸酯及其組合。
在又一實施例中，反應性稀釋劑為二丙烯酸酯，諸如1,6-己二醇二丙烯酸酯、1,9-壬二醇二丙烯酸酯、1,4-丁二醇二丙烯酸酯、三環癸烷二甲醇二丙烯酸酯、環己烷二甲醇二丙烯酸酯、烷氧基化環己烷
二丙烯酸酯及三丙二醇二丙烯酸酯。在另一實施例中，反應性稀釋劑包括丙氧基化新戊二醇二丙烯酸酯及三丙二醇二丙烯酸酯。
在又一實施例中，反應性稀釋劑可為烯丙基苯基醚、2-烯丙基苯基醚、2-烯丙基苯酚、烯丙基苯酚酚醛清漆樹脂、丁香酚、二烯丙基雙酚A或三聚氰酸三烯丙酯。
在另一實施例中，反應性稀釋劑選自烯丙基縮水甘油醚、丙烯酸縮水甘油醚、甲基丙烯酸縮水甘油醚、部分丙烯酸化環氧基及其混合物。
在一些實施例中，按可固化組合物之總重量計，反應性稀釋劑可以介於約1重量%至約40重量%之範圍內的量包含於可固化組合物中。在另一實施例中，按可固化組合物之總重量計，反應性稀釋劑可以介於約5重量%至約30重量%之範圍內的量包含於可固化組合物中。
在另一實施例中，按可固化組合物之總重量計，反應性稀釋劑可以大於約1重量%，且在其他實施例中以大於約5重量%之量包含於可固化組合物中。在另一實施例中，按可固化組合物之總重量計，反應性稀釋劑可以小於約40重量%，且在其他實施例中以小於約30重量%之量包含於可固化組合物中。
在另一實施例中，可固化組合物含有可溶性聚醯亞胺。本發明之可溶性聚醯亞胺衍生自(i)苯基茚滿二胺及(ii)苯基茚滿二酐及/或二酐。詳言之，可溶性聚醯亞胺含有式(4)之重複單元：
其中4個羰基鍵結於不同碳原子上且彼此處於相鄰或相對位置以
形成五或六員醯亞胺環；Z 1 為含有至少一個芳環之四價基團，其中羰基連接至該環；且Z 2 為二價有機基團，其選自芳族、脂族、烷基芳族、環脂族及雜環基團、其組合及具有含雜原子橋接基之殘基(其中橋中之雜原子為氧、硫、氮、矽或磷)。此等可溶性聚醯亞胺進一步描述於美國專利第3,856,752號中，其全部內容以引用之方式併入本文中。
在一個實施例中，可溶性聚醯亞胺含有式(4)之重複單元，其中Z 1 為式(5)之苯基茚滿基：
其中R 4 為氫或C1-C5烷基；且Z 2 為式(6)之苯基茚滿基：
其中R 5 為氫或C1-C5烷基且R6、R7、R8及R9各自獨立地為氫、鹵素或C1-C4烷基。
可溶性聚醯亞胺之苯基茚滿二胺組分可由式(6)之異構體或經取代之異構體的任何組合組成。苯基茚滿二胺組分可例如含有0重量%至100重量%之5-胺基-1-(4'-胺基苯基)-1,3,3-三甲基茚滿與100重量%至0重量%之6-胺基-1-(4'-胺基苯基)-1,3,3-三甲基茚滿之組合。此外，任何式(6)之經取代之二胺基異構體可在0重量%至100重量%之整個範
圍內取代此等異構體中之一者或兩者。此類經取代之二胺基異構體之實例為5-胺基-6-甲基-1-(3'-胺基-4'-甲基苯基)-1,3,3-三甲基茚滿、5-胺基-1-(4'-胺基-Ar',Ar'-二氯苯基)-Ar、Ar-二氯-1,3,3-三甲基茚滿、6-胺基-1-(4'-胺基-Ar',Ar'-二氯苯基)-Ar、Ar-二氯-1,3,3-三甲基茚滿、4-胺基-6-甲基-1-(3'-胺基-4'-甲基苯基)-1,3,3-三甲基茚滿及Ar-胺基-1-(Ar'-胺基-2',4'-二甲基苯基)-1,3,3,4,6-五甲基茚滿，其中上文提及之化合物中之前綴Ar及Ar'表示指定取代基在苯基環中之位置不確定。
在一個實施例中，式(6)之苯基茚滿二胺中較佳為R5為氫或甲基，R6及R7獨立地為氫、甲基、氯或溴，且R8及R9獨立地為氫、氯或溴之彼等苯基茚滿二胺。在另一實施例中，R5為氫或甲基，R6及R7獨立地為氫、甲基、氯或溴，且R8及R9獨立地為氫、氯或溴，且胺基在5位、6位或7位及3'位或4'位。在另一實施例中，R5為氫或甲基，R6、R7、R8及R9為氫，且胺基在5位或6位及4'位。
在另一實施例中，Z2為具有式(7)之基團：
其中L為共價鍵、亞甲基、硫、氧或碸；且R11及R12獨立地為氫、鹵素、C1-C5烷基或具有下式之基團：
其中R13為氫、鹵素或C1-C5烷基。
在一個實施例中，苯基茚滿二酐為具有式(8)之化合物：
其中R14為氫或C1-C5烷基。此類二酐之實例包括1-(3',4'-二羧基苯基)-1,3,3-三甲基茚滿-5,6-二甲酸二酐、1-(3',4'-二羧基苯基)-1,3,3-三甲基茚滿-6,7-二甲酸二酐、1-(3',4'-二羧基苯基)-3-甲基茚滿-5,6-二甲酸二酐及1-(3',4'-二羧基苯基)-3-甲基茚滿-6,7-二甲酸二酐。
其他可與苯基茚滿二酐組合或自身單獨使用之二酐為以式(9)為特徵之化合物：
其中四價基團
如上文所定義。
在一個實施例中，較佳為芳族二酐，其中每對羰基之碳原子直接連接至Z1基團中之相鄰或相對碳原子上，得到以下五或六員環：
可使用之二酐的具體實例包括2,3,9,10-苝四甲酸二酐、1,4,5,8-萘四甲酸二酐、2,6-二氯萘-1,4,5,8-四甲酸二酐、2,7-二氯萘-1,4,5,8-四甲酸二酐、2,3,6,7-四氯萘-1,4,5,8-四甲酸二酐、菲-1,8,9,10-四甲酸二酐、2,3,3',4'-二苯甲酮四甲酸二酐、苯均四酸二酐、3,3',4,4'-二苯甲酮四甲酸二酐、2,2',3,3'-二苯甲酮四甲酸二酐、3,3',4,4'-聯苯四甲酸二酐、2,2',3,3'-聯苯四甲酸二酐、4,4'-亞異丙基雙苯二甲二酐、3,3'-亞異丙基雙苯二甲酸二酐、4,4'-氧雙苯二甲酸二酐、4,4'-磺醯基雙苯二甲酸二酐、3,3'-氧雙苯二甲酸二酐、4,4'-亞甲基雙苯二甲酸二酐、4,4'-硫基雙苯二甲酸二酐、4,4'-亞乙基雙苯二甲酸二酐、2,3,6,7-萘四甲酸二酐、1,2,4,5-萘四甲酸二酐、1,2,5,6-萘四甲酸二酐、苯-1,2,3,4-四甲酸二酐、吡
-2,3,5,6-四甲酸二酐及噻吩-2,3,4,5-四甲酸二酐。
在一個特定實施例中，可溶性聚醯亞胺為高分子量化合物，如美國專利第3,856,752號中所描述，其藉由使5(6)-胺基-1(4'-胺基苯基)1,1,3-三甲基茚滿(BAPI)與二苯甲酮四甲酸二酐(BTDA)反應來製備。此可溶性聚醯亞胺可以MATRIMID®商標(例如MATRIMID® 5218及9725聚醯亞胺)購自Huntsman Advanced Materials Americas LLC。
根據一個實施例，按可固化組合物之總重量計，可溶性聚醯亞胺可以介於約0.1重量%至約25重量%之範圍內的量包含於可固化組合物中。在另一實施例中，按可固化組合物之總重量計，可溶性聚醯亞
胺可以介於約1重量%至約20重量%之範圍內的量包含於可固化組合物中。在其他實施例中，按可固化組合物之總重量計，可溶性聚醯亞胺可以大於約0.1重量%，且在其他實施例中以大於約0.5重量%，且甚至在其他實施例中以至少1重量%的量包含於可固化組合物中。在又一實施例中，按可固化組合物之總重量計，可溶性聚醯亞胺可以小於約25重量%，且在其他實施例中以小於約20重量%，且甚至在其他實施例中以小於約15重量%之量包含於可固化組合物中。
在另一實施例中，可固化組合物可視情況含有一或多種添加劑。此類添加劑之實例包括(但不限於)其他增韌劑、觸媒、增強劑、填充劑、助黏劑、阻燃劑、搖變劑及其混合物。
可使用之其他增韌劑之實例包括基於丁二烯/丙烯腈之共聚物、丁二烯/(甲基)丙烯酸酯、丁二烯/丙烯腈/苯乙烯接枝共聚物(「ABS」)、丁二烯/甲基丙烯酸甲酯/苯乙烯接枝共聚物(「MBS」)、聚(氧化丙烯)、胺封端之丁二烯/丙烯腈共聚物(「ATBN」)及羥基封端之聚醚碸(諸如可商購自Sumitomo Chemical Company之PES 5003P增韌劑，或來自Solvay Advanced Polymers,LLC之RADEL®增韌劑)、核殼型橡膠及聚合物(諸如PS 1700增韌劑)、在環氧樹脂基質中具有核-殼結構之橡膠粒子(諸如來自Kaneka Corporation之MX-120樹脂、來自Wacker Chemie GmbH之GENIOPEARL® M23A樹脂)、經橡膠改質之環氧樹脂(例如環氧樹脂及二烯橡膠或共軛二烯/腈橡膠之環氧基封端加合物)、及高分子量聚醚醯亞胺(諸如ULTEM® 2000產品、Rlendex 338產品及SILTEMTM STM 1500產品)。
可使用之觸媒的實例包括酚化合物及其衍生物、諸如烯酸之強酸、諸如金屬鹵化物之陽離子觸媒、有機金屬衍生物、諸如氯化鋁酞菁之金屬卟啉化合物、甲苯磺酸甲酯、三氟甲磺酸甲酯及三氟甲磺酸及氧鹵化物。在一個實施例中，觸媒為酚化合物，諸如苯酚、鄰甲
酚、鄰-、間-或對-二羥基苯、2,4,6-三硝基苯酚、2,6-二第三丁基-對甲酚-羥基苯、2,2'-二羥基聯苯酚、雙酚A、雙酚F、雙酚S及4,4-硫代二酚。在另一實施例中，觸媒為酸，諸如乙酸、丙酸、草酸、己二酸、癸二酸、苯甲酸、硫酸、對甲苯磺酸、磷酸或硫二丙酸。
可使用之填充劑及增強劑之實例包括矽石、預分散於環氧樹脂中之矽石奈米粒子、煤焦油、瀝青、紡織纖維、玻璃纖維、石棉纖維、硼纖維、碳纖維、矽酸鹽礦物、雲母、粉末狀石英、水合氧化鋁、膨潤土、矽灰石、高嶺土、氣凝膠或金屬粉末(例如鋁粉或鐵粉)、以及顏料及染料(諸如碳黑、氧化物色料及二氧化鈦)、輕質微氣球(諸如微珠、玻璃微球、碳及聚合物微氣球)、阻燃劑、搖變劑、流量控制劑(諸如聚矽氧、蠟及硬脂酸酯)，其亦可部分用作脫模劑、助黏劑、抗氧化劑及光穩定劑，可控制以上多者之粒度及分佈來改變可固化組合物之物理特性及效能。
添加劑若存在，則可按可固化組合物之總重量計以介於約0.1重量%至約40重量%之範圍內的量添加至可固化組合物中。在其他實施例中，添加劑可按可固化組合物之總重量計以介於約1重量%至約30重量%之範圍內的量，且在其他實施例中介於約5重量%至約15重量%之間的量添加至可固化組合物中。
本發明之可固化組合物可藉由已知方法製備，例如藉由在研磨機或乾式混合器中憑藉已知的混合單元(諸如捏合機、攪拌器、滾筒)組合苯并
、反應性稀釋劑、可溶性聚醯亞胺及視情況選用之添加劑。因為苯并
一經加熱即能夠同元聚合，使其對用於熔化及溶解所存在之其他添加劑通常所需的高加工溫度具有敏感性，所以根據一些實施例，可首先組合反應性稀釋劑及可溶性聚醯亞胺，且用其溶解任何存在之添加劑，隨後添加苯并
。因此，在一個實施例中，提供一種用於製造可固化組合物之方法，其包含(a)將可溶性聚醯亞胺
與反應性稀釋劑及視情況選用之添加劑混合以產生均質溶液或分散液；及(b)將苯并
與均質溶液或分散液混合以形成可固化組合物。
已出人意料地發現，本發明之苯并
、反應性稀釋劑及可溶性聚醯亞胺在組合時形成可固化組合物，其一經固化，即產生展現熱特性、機械特性及物理特性之極佳平衡(諸如高玻璃轉化溫度(Tg)、高韌性、高機械強度、高水解穩定性及阻燃性)之固化物品。
因此，根據一個特定實施例，可固化組合物一經固化，即得到具有大於約180℃之玻璃轉化溫度(如藉由動態機械分析或「DMA」所測定)的物品。在其他實施例中，可固化組合物一經固化，即得到具有大於約200℃，且在其他實施例中大於約210℃，且甚至在其他實施例中大於約220℃之玻璃轉化溫度(如藉由DMA所測定)的物品。
在其他實施例中，可固化組合物一經固化，即得到展現大於約200J/m2，且在其他實施例中大於約225J/m2之斷裂韌性G1c(應變能之臨界釋放速率)的物品。
在其他實施例中，可固化組合物一經固化，即得到在乾燥條件下展現大於約4000MPa之乾式撓曲模數E'值，及當在120℃下量測時乾式撓曲模數E'之保持率大於80%之物品。
在又一實施例中，可固化組合物一經固化，即得到具有如下所示之極佳水解穩定性之物品：在75℃水中浸沒至少21天後水分吸收率(亦即增重)小於3.0%；及/或在暴露於沸水中約48小時後強度損失率小於5%。
可固化組合物可在高溫及/或高壓條件下固化形成固化物品。固化可按一個或兩個或多於兩個階段進行，第一固化階段在較低溫度下進行，且隨後在較高溫度下進行後固化。在一個實施例中，固化可按一或多個階段在約30℃至300℃之範圍內，在其他實施例中在約140℃至220℃之範圍內的溫度下進行。固化速率可在約30分鐘至6小時之範圍內。
如上所述，可固化組合物尤其適於用作塗層、黏著劑、密封劑及用於製備強化複合材料之基質，諸如預浸體及束狀預浸體，且亦可用於注射模製或擠出製程中。
因此，在另一實施例中，本發明提供一種用於電子組件或電組件之黏著劑、密封劑、塗層或封裝系統，其包含本發明之可固化組合物。可在上面塗覆包含可固化組合物之塗層、密封劑、黏著劑或封裝系統且加熱以固化的適合基板包括金屬，諸如鋼、鋁、鈦、鎂、黃銅、不鏽鋼、鍍鋅鋼；矽酸鹽，諸如玻璃及石英；金屬氧化物；混凝土；木材；電子晶片材料，諸如半導體晶片材料；或聚合物，諸如聚醯亞胺薄膜及聚碳酸酯。包含可固化組合物之黏著劑、密封劑或塗層可用於多種應用中，諸如工業或電子應用中。
在另一實施例中，本發明提供一種固化產物，其包含灌注有可固化組合物之纖維束或纖維層。
在又一實施例中，本發明提供一種用於製造預浸體或束狀預浸體之方法，其包括以下步驟：(a)提供纖維束或纖維層；(b)提供本發明之可固化組合物；(c)將纖維束或纖維層與可固化組合物結合以形成預浸體或束狀預浸體總成；(d)視情況自預浸體或束狀預浸體總成中移除多餘可固化組合物；及(e)將預浸體或束狀預浸體總成暴露於足以將可固化組合物注入纖維束或纖維層且形成預浸體或束狀預浸體之高溫及/或高壓條件下。
在一些實施例中，纖維束或纖維層可由單向纖維、紡織纖維、短切纖維、非紡織纖維或不連續長纖維構築。纖維可選自玻璃(諸如S玻璃、S2玻璃、E玻璃、R玻璃、A玻璃、AR玻璃、C玻璃、D玻璃、ECR玻璃、玻璃絲、切段玻璃、T玻璃及鋯玻璃)、碳、聚丙烯腈、丙烯酸、芳族聚醯胺、硼、聚伸烷基、石英、聚苯并咪唑、聚醚酮、聚苯硫醚、聚對伸苯基苯并二噁唑、碳化矽、苯酚甲醛、鄰苯二甲酸酯
及環烷酸酯。
可固化組合物(及自其製備之預浸體或束狀預浸體)特別適用於製造及組裝用於航空及汽車應用之複合部件、複合及金屬部件之黏結、夾層結構之核心及核心填充及複合表面休整。
在100℃下，將70公克雙酚A苯并
樹脂(來自Huntsman Advanced Materials Americas LLC之XU 35610樹脂)溶解於30公克環氧基反應性稀釋劑(來自Huntsman Advanced Materials Americas LLC之Araldite® CY-179樹脂)中，持續約30分鐘，獲得均質溶液。
如比較實例1中所述製備均質溶液，但亦改添加10公克CTBN 1300x8橡膠且混合以獲得均質溶液。
如比較實例1中所述製備均質溶液，但亦改添加10公克ATBN 1300x16橡膠且混合以獲得均質溶液。
在130℃下，將5公克可溶性聚醯亞胺(Matrimid® 9725聚醯亞胺)溶解於30公克環氧基反應性稀釋劑(Araldite® CY-179樹脂)中，持續30分鐘，獲得均質溶液(「預混物」)。隨後在130℃下，將70公克雙酚A苯并
樹脂(XU 35610樹脂)溶解於預混物中，持續約30分鐘，獲得均質溶液。
如實例4中所述製備均質溶液，但改用7公克而非5公克可溶性聚醯亞胺(Matrimid® 9725聚醯亞胺)。
於真空下在約130℃之溫度下進一步混合均質溶液中之每一者約
15至30分鐘。隨後將溶液轉移至含有0.125吋Teflon®隔片之經預加熱(150℃)之玻璃模具中，且在180℃下固化2小時，且隨後在200℃下固化2小時，且最後在220℃下固化2小時。使用差示掃描熱量測定(10℃/min之加熱速率)及動態機械分析(5℃/min之加熱速率)測試固化物品來測定Tg、起始及儲存模數值。此外，對固化物品進行75℃浸水測試達21天來測定增量%，且對其進行沸水測試達48小時來測定強度損失率：
亦根據ASTM D 790測定各固化物品之撓曲強度及模數，且根據ASTM D5045-96測定K1c及G1c值：
比較表1中之結果，可以看出實例4及5之Tg相比對照組比較實例1之Tg，無明顯改變。然而，實例4之Tg略佳於比較實例2及3之Tg，而實例5之Tg大致相當於或略佳於比較實例2及3之Tg。亦可看出如藉由DMA儲存模數所量度之強度保持率明顯優於比較實例2及3之強度保持率。這一點在暴露於沸水中48小時之後在30℃及121℃下測試時得到證實。
比較表2中之結果，顯然可溶性聚醯亞胺實例(實例4及5)保持拉伸及撓曲特性之程度遠高於比較實例2或3。此外，值得注意的是，實例4及5之撓曲模數的保持率略高於比較實例1之撓曲模數的保持率。此外，相比於比較實例1，實例4及5之斷裂韌性G1c增加兩倍。
參考表1及表2，可以看出本發明之可固化組合物在固化時展現：1)高韌性，如藉由大於200J/m2，尤其大於225J/m2之斷裂韌性
G1c(亦即應變能之臨界釋放速率)所量度；2)大於180℃，尤其大於200℃之玻璃轉化溫度Tg；3)高強度，如藉由在乾燥條件下大於4000MPa之乾式撓曲模數E'值且當在120℃下量測時大於80%之乾式撓曲模數E'保持率所量度；。及4)極佳水解穩定性，如藉由小於3.0%之熱水浸沒重量吸收率及小於5%之強度損失率所量度。
儘管上文已詳細地描述本發明之各種實施例的產生及使用，但應瞭解本發明提供諸多可在廣泛多種特定情況下實施之可適用的發明概念。本文所論述之特定實施例僅用於說明製造及使用本發明之具體方式，且不限定本發明之範疇。
Claims (12)
- 一種可固化組合物，其包含：(a)約40重量%至約90重量%之苯并；(b)約5重量%至約30重量%之環氧基反應性稀釋劑；及(c)可溶性聚醯亞胺，其中該可溶性聚醯亞胺係(i)包含式(4)之重複單元的可溶性聚醯亞胺：
- 如請求項1之可固化組合物，其中該苯并為式(1)化合物：
- 如請求項2之可固化組合物，其中各R獨立地為氫、經取代或未經取代之C1-C20烷基、經取代或未經取代之C2-C20烯基、經取代或未經取代之C6-C20芳基、經取代或未經取代之C2-C20雜芳基、 經取代或未經取代之C2-C20雜環基或C3-C8環烷基。
- 如請求項2之可固化組合物，其中該苯并為式(1a)化合物：
；各R獨立地為氫、C1-C20烷基、烯丙基或C6-C14芳基；且R1獨立地為氫、C1-C20烷基、C2-C20烯基或C6-C20芳基。
- 如請求項1之可固化組合物，其中該環氧基反應性稀釋劑係選自乙烯基環己烯二氧化物、檸檬烯二氧化物、二環戊二烯二氧化物、3,4-環氧基二氫二環戊二烯基縮水甘油醚、乙二醇之雙(3,4-環氧基二氫二環戊二烯基)醚、3,4'-環氧基環己烷甲酸3,4-環氧基環己基甲酯、3,4'-環氧基環己烷甲酸3,4-環氧基環己基甲酯之6,6'-二甲基衍生物、乙二醇之雙(3,4-環氧基環己烷甲酸酯)、在3,4-環氧基環己烷甲醛與1,1-雙(羥甲基)-3,4-環氧基環己烷之間形成的縮醛及雙(2,3-環氧環戊基)醚。
- 如請求項1之可固化組合物，其進一步包含下列一者或多者：增韌劑、觸媒、增強劑、填充劑、助黏劑、阻燃劑或搖變劑。
- 如請求項1之可固化組合物，其中該可固化組合物包含：(a)約50重量%至約80重量%之該苯并；及(c)約0.1重量%至約25重量%之該可溶性聚醯亞胺， 其中該等重量%係以該可固化組合物之總重量計。
- 一種用於製造可固化組合物之方法，其包含(a)將可溶性聚醯亞胺與約5重量%至約30重量%之反應性稀釋劑及視情況選用之添加劑混合，產生均質溶液或分散液；(b)將約40重量%至約90重量%之苯并與該均質溶液或分散液混合以形成該可固化組合物，其中該等重量%係以該可固化組合物之總重量計；且其中該可溶性聚醯亞胺係(i)包含式(4)之重複單元的可溶性聚醯亞胺：
- 一種固化物品，其包含如請求項1至7中任一項之可固化組合物。
- 如請求項9之固化物品，其包含以下特性中之一或多者：(i)大於200J/m2之斷裂韌性G1c；(ii)大於180℃之玻璃轉化溫度Tg；(iii)在乾燥條件下大於4000MPa之乾式撓曲模數E'；及(iv)如藉由浸沒在75℃水中達至少21天所量測，增重小於3.0%之水解穩定性。
- 一種固化物品，其包含灌注有如請求項1至7中任一項之可固化組合物的纖維束或纖維層。
- 一種用於製造預浸體或束狀預浸體之方法，其包含以下步驟：(a)提供纖維束或纖維層；(b)提供如請求項1至7中任一項之可固化組合物；(c)將該纖維束或纖維層與該可固化組合物結合以形成預浸體或束狀預浸體總成；(d)視情況自該預浸體或束狀預浸體總成中移除多餘可固化組合物；及(e)將該預浸體或束狀預浸體總成暴露於足以將該可固化組合物注入該纖維束或纖維層且形成預浸體或束狀預浸體之高溫及/或高壓條件下。
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| JP7143555B1 (ja) * | 2021-03-08 | 2022-09-28 | Ｊｆｅケミカル株式会社 | ポリイミド樹脂およびその製造方法、ポリイミド樹脂溶液、コーティング材料ならびに成形材料 |
| CN115433334B (zh) * | 2021-06-02 | 2023-12-15 | 北京化工大学 | 双（三羟甲基）丙烷缩醛结构的主链型苯并噁嗪树脂 |
| CN116355180B (zh) * | 2023-03-27 | 2024-06-14 | 福建省晋江市大远鞋塑有限公司 | 一种苯并噁嗪基聚氨酯弹性体鞋底材料的制备方法 |
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| WO2017015376A1 (en) | 2017-01-26 |
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| RU2748127C2 (ru) | 2021-05-19 |
| AU2016296886B2 (en) | 2020-04-30 |
| US20180186730A1 (en) | 2018-07-05 |
| KR102609660B1 (ko) | 2023-12-06 |
| EP3325533A1 (en) | 2018-05-30 |
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