TWI344477B - - Google Patents
Download PDFInfo
- Publication number
- TWI344477B TWI344477B TW093122161A TW93122161A TWI344477B TW I344477 B TWI344477 B TW I344477B TW 093122161 A TW093122161 A TW 093122161A TW 93122161 A TW93122161 A TW 93122161A TW I344477 B TWI344477 B TW I344477B
- Authority
- TW
- Taiwan
- Prior art keywords
- compound
- polyvalent
- vinyl ether
- weight
- curable composition
- Prior art date
Links
- -1 vinyl ether compound Chemical class 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 64
- 239000000203 mixture Substances 0.000 claims description 45
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 21
- 239000004593 Epoxy Substances 0.000 claims description 20
- 239000003063 flame retardant Substances 0.000 claims description 19
- 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 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000005011 phenolic resin Substances 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- 239000000945 filler Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 229910000420 cerium oxide Inorganic materials 0.000 claims description 3
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 2
- 238000001723 curing Methods 0.000 description 25
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000003822 epoxy resin Substances 0.000 description 12
- 229920000647 polyepoxide Polymers 0.000 description 12
- 150000001450 anions Chemical class 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000005977 Ethylene Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 230000009477 glass transition Effects 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000000052 vinegar Substances 0.000 description 7
- 235000021419 vinegar Nutrition 0.000 description 7
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 6
- 229920001568 phenolic resin Polymers 0.000 description 6
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 229910052785 arsenic Inorganic materials 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000223 polyglycerol Polymers 0.000 description 3
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- OATKBOXEDDXPQV-UHFFFAOYSA-N F.F.F.F.F.F.F.F.F.F.F.F Chemical compound F.F.F.F.F.F.F.F.F.F.F.F OATKBOXEDDXPQV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- ZTHQBROSBNNGPU-UHFFFAOYSA-M butyl sulfate(1-) Chemical compound CCCCOS([O-])(=O)=O ZTHQBROSBNNGPU-UHFFFAOYSA-M 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012765 fibrous filler Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- GESMLGHYDFUAAY-UHFFFAOYSA-N 1,1-diphenyl-2-(4-thiophen-2-yloxyphenyl)hydrazine Chemical compound C1(=CC=CC=C1)N(NC1=CC=C(C=C1)OC=1SC=CC=1)C1=CC=CC=C1 GESMLGHYDFUAAY-UHFFFAOYSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- RMYXXJKVVYQPLG-UHFFFAOYSA-N 1h-imidazol-1-ium;sulfate Chemical compound [NH2+]1C=CN=C1.[NH2+]1C=CN=C1.[O-]S([O-])(=O)=O RMYXXJKVVYQPLG-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- XXKHDSGLCLCFSC-UHFFFAOYSA-N 2,3-diphenylphenol Chemical compound C=1C=CC=CC=1C=1C(O)=CC=CC=1C1=CC=CC=C1 XXKHDSGLCLCFSC-UHFFFAOYSA-N 0.000 description 1
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 description 1
- WCJDNMVAWZWQJU-UHFFFAOYSA-N 2-propyl-6-oxabicyclo[3.1.1]heptane Chemical compound C1(CCC)C2OC(CC1)C2 WCJDNMVAWZWQJU-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- ANOPCGQVRXJHHD-UHFFFAOYSA-N 3-[3-(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]propan-1-amine Chemical compound C1OC(CCCN)OCC21COC(CCCN)OC2 ANOPCGQVRXJHHD-UHFFFAOYSA-N 0.000 description 1
- HDPBBNNDDQOWPJ-UHFFFAOYSA-N 4-[1,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HDPBBNNDDQOWPJ-UHFFFAOYSA-N 0.000 description 1
- ZYEDGEXYGKWJPB-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)(C)C1=CC=C(N)C=C1 ZYEDGEXYGKWJPB-UHFFFAOYSA-N 0.000 description 1
- HVMHLMJYHBAOPL-UHFFFAOYSA-N 4-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propan-2-yl]-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2CC1C(C)(C)C1CC2OC2CC1 HVMHLMJYHBAOPL-UHFFFAOYSA-N 0.000 description 1
- OXRFNJSKALBWCF-UHFFFAOYSA-N 4-[4,4-bis(4-hydroxyphenyl)butan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)CC(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 OXRFNJSKALBWCF-UHFFFAOYSA-N 0.000 description 1
- JTZJHTZCYBYCSZ-UHFFFAOYSA-N 4-ethyl-4-propylheptane Chemical compound CCCC(CC)(CCC)CCC JTZJHTZCYBYCSZ-UHFFFAOYSA-N 0.000 description 1
- ULPDSNLBZMHGPI-UHFFFAOYSA-N 4-methyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C)CCC2OC21 ULPDSNLBZMHGPI-UHFFFAOYSA-N 0.000 description 1
- QHHKLPCQTTWFSS-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QHHKLPCQTTWFSS-UHFFFAOYSA-N 0.000 description 1
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 description 1
- DWZRPAFRYWCGEZ-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-3-ylmethanamine Chemical compound C1C(CN)CCC2OC21 DWZRPAFRYWCGEZ-UHFFFAOYSA-N 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- 240000002900 Arthrospira platensis Species 0.000 description 1
- 235000016425 Arthrospira platensis Nutrition 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- 229920001342 Bakelite® Polymers 0.000 description 1
- UUAGPGQUHZVJBQ-UHFFFAOYSA-N Bisphenol A bis(2-hydroxyethyl)ether Chemical compound C=1C=C(OCCO)C=CC=1C(C)(C)C1=CC=C(OCCO)C=C1 UUAGPGQUHZVJBQ-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- MXQXPFVFGCEMKT-UHFFFAOYSA-N C(CCCCCCCCC)C=CC.OCC(O)CO Chemical group C(CCCCCCCCC)C=CC.OCC(O)CO MXQXPFVFGCEMKT-UHFFFAOYSA-N 0.000 description 1
- UJNWHEVTLFYKPO-UHFFFAOYSA-N C1(=CC=C(C=C1)C)IC1=CC=C(C=C1)C Chemical compound C1(=CC=C(C=C1)C)IC1=CC=C(C=C1)C UJNWHEVTLFYKPO-UHFFFAOYSA-N 0.000 description 1
- MNTNARNHEPKROC-UHFFFAOYSA-N C=1C=CC=CC=1[Ba]C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1[Ba]C1=CC=CC=C1 MNTNARNHEPKROC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PCVBOQNPSAIIDH-UHFFFAOYSA-N F[I](F)(F)(F)(F)F Chemical compound F[I](F)(F)(F)(F)F PCVBOQNPSAIIDH-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- PDOIYKSLJKHDPK-UHFFFAOYSA-N NC1=C2C(=CNC2=CC=C1)C(CCCCCCCCC)C1=CNC2=CC=CC(=C12)N Chemical compound NC1=C2C(=CNC2=CC=C1)C(CCCCCCCCC)C1=CNC2=CC=CC(=C12)N PDOIYKSLJKHDPK-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- PWHYOGRKVRMWLT-UHFFFAOYSA-H [F-].[F-].[F-].[F-].[F-].[F-].C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1 Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1.C1(=CC=CC=C1)[I+]C1=CC=CC=C1 PWHYOGRKVRMWLT-UHFFFAOYSA-H 0.000 description 1
- AFKGJUQOMNOUHY-UHFFFAOYSA-N [F-].[F-].[F-].[F-].[F-].[F-].COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC.COC1=CC=C(C=C1)[PH+](C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC AFKGJUQOMNOUHY-UHFFFAOYSA-N 0.000 description 1
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
- BZIJZOCPZVZXJB-UHFFFAOYSA-N acetic acid;ethyl 3-oxobutanoate Chemical compound CC(O)=O.CCOC(=O)CC(C)=O BZIJZOCPZVZXJB-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- DJUWPHRCMMMSCV-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) hexanedioate Chemical compound C1CC2OC2CC1COC(=O)CCCCC(=O)OCC1CC2OC2CC1 DJUWPHRCMMMSCV-UHFFFAOYSA-N 0.000 description 1
- ZZUFUNZTPNRBID-UHFFFAOYSA-K bismuth;octanoate Chemical compound [Bi+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O ZZUFUNZTPNRBID-UHFFFAOYSA-K 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- ULBTUVJTXULMLP-UHFFFAOYSA-N butyl octadecanoate Chemical group CCCCCCCCCCCCCCCCCC(=O)OCCCC ULBTUVJTXULMLP-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012952 cationic photoinitiator Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- VVRKSAMWBNJDTH-UHFFFAOYSA-N difluorophosphane Chemical compound FPF VVRKSAMWBNJDTH-UHFFFAOYSA-N 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-O diphenylphosphanium Chemical compound C=1C=CC=CC=1[PH2+]C1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-O 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-O diphenylsulfanium Chemical compound C=1C=CC=CC=1[SH+]C1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-O 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- ZHJWYNABZXBYAX-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2,3-triol Chemical compound OCCO.OCC(O)CO.OCC(O)CO ZHJWYNABZXBYAX-UHFFFAOYSA-N 0.000 description 1
- JJVJPJWQXDQCEI-UHFFFAOYSA-N ethenylhydrazine Chemical compound NNC=C JJVJPJWQXDQCEI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- RBNPOMFGQQGHHO-UHFFFAOYSA-N glyceric acid Chemical compound OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- DEODFHDPCQFPGW-UHFFFAOYSA-H hexafluoroiron Chemical compound F[Fe](F)(F)(F)(F)F DEODFHDPCQFPGW-UHFFFAOYSA-H 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 230000008774 maternal effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RLFXWALMKAWBBF-UHFFFAOYSA-N methyl prop-2-enoate propane-1,2,3-triol Chemical compound C(C=C)(=O)OC.OCC(O)CO RLFXWALMKAWBBF-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- ROMWNDGABOQKIW-UHFFFAOYSA-N phenyliodanuidylbenzene Chemical compound C=1C=CC=CC=1[I-]C1=CC=CC=C1 ROMWNDGABOQKIW-UHFFFAOYSA-N 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000008442 polyphenolic compounds Polymers 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 229940082787 spirulina Drugs 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 239000004291 sulphur dioxide Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/5399—Phosphorus bound to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0066—Flame-proofing or flame-retarding additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C08L61/14—Modified phenol-aldehyde condensates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2361/04—Condensation polymers of aldehydes or ketones with phenols only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2361/04—Condensation polymers of aldehydes or ketones with phenols only
- C08J2361/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C08J2361/14—Modified phenol-aldehyde condensates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Reinforced Plastic Materials (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
1344477 九、發明說明: 【發明所屬之技術領域】 本發明係關於-種乙稀趟固化性組合物,其包含多價乙 烯越化σ物和夕價酚化合物。詳細説來,該乙婦驗固化性 組合物係藉由將多價乙烯醚化合物和多價酚化合物加熱固 化,得以形成低介電常數的固化物,該乙婦喊固化性組合 物適用於形成用料層板,特別是積體(built_up)用積層二 的預浸材料。 【先前技術】 含有環氧樹脂等的固化性樹脂在熱或者光的條件下固化 而形成的組合物’純廣泛應用作爲積層板、塗料、枯合 劑、光造型等的材料。廣爲人知的固化性樹脂有以二笨紛 A的一甘油趟為代表的芳香族環氧化合物;2,2·二(3,4-環氧 衣己基)丙& 3’4_環氧環己基幾基經甲基-3,4-環氧環己烷 等脂環式環氧化合物;乙二醇二甘油謎、(甲基)丙埽酸甘 ㈣等的脂肪族環氧化合物等許多環氧化合物加上多價 月女化合物’多價紛化合物,酸針等固化劑,而得到的環氧 樹脂。 >固化性樹脂除了環氧樹脂外,已知的還有使用二李戊四 醇己丙烯酸樹脂的光固化樹脂等。 由這些固化性樹脂得到固化物時,有必要控制玻璃轉化 '皿度、吸水率、介電常數、耐衝擊強度、牽引強度、牽引 伸展率、黏合強度等特性,以及固化時的固化速度和固化 條件等。因此有必要選擇適宜的化合物結構和組成。特別 94949-1000421.doc 1J44477 {用於積體電路的固化物必須有高的玻璃轉化溫度、優良 的介電特性以及低的吸水率。 從性能的平衡上考慮,積層板大多採用環氧樹脂。環氧 化合物的結構改變而進行的特性調節,㈣記載於下述專 利文獻!和2中。下述專利文獻】和2中,記載了 2,2二(3,4- 環氧環己基)丙烧有高的玻璃轉化溫度,提議該化合物用於 光造型以及積層板等。 專利文獻1 :特開平5-105896號公報 ^ 專利文獻2 :特開平11_255863號公報 但是,以環氧化合物及其固化劑爲主體的固化物要滿足 所有的性能很困難,特別是提供期望適用於微細化技術進 步顯著的積層板用途之能夠形成介電常數低的固化物的固 化性組合物。 因此本發明的目的為提供一種固化性組合物,特別是其 能夠形成低介電常數的固化物。 【發明内容】 本發明(關於申請專利範圍第丨項的發明)係提供一種乙 烯職固化性組合物’其包含多價乙稀鍵化合物以及多價酚 化合物,以達成上述目的。 另外,關於申請專利範圍第2項的發明係提供申請專利範 圍第1項之乙烯醚固化性組合物,其由上述多價乙烯醚化合 物100重量分及上述多價酚化合物化合物重量分,與 填充材料10〜3000重量分及難燃劑1〇〜2〇〇重量分混合而成。 另外’關於申請專利範圍第3項之發明係提供申請專利範 94949-1000421.doc 1344477 圍第1或2項之乙烯醚固化性组合物,其包含的上述多價乙 稀喊化合物為4價以上的多價乙烯醚化合物。 另外’關於申請專利範圍第4項之發明係提供申請專利範 圍第1〜3中任一項之乙烯醚固化性組合物,其包含的上述多 價紛化合物為下述一般式(I)所示的酚樹脂: [化1]
Η ⑴ (式中η代表〇或者im代表1〜loooo)。 另外’關於申請專利範圍第5項之發明係提供申請專利範 圍第1〜4中任一項之乙烯醚固化性組合物,其由上述多價乙 烯醚化合物之混合量及上述多價酚化合物的混合量總計 100重量分’與作為上述填充材料之二氧化矽10〜10〇〇重量 分混合而成。 另外’關於申請專利範圍第6項之發明係提供申請專利範 圍第1〜5中任一項之乙烯醚固化性組合物,其由上述多價乙 烯醚化合物之混合量及上述多價酚化合物的混合量總計 100重量分,與作為上述難燃劑之磷系難燃劑丨〇~5〇重量分 混合而成。 另外,關於申請專利範圍第7項之發明係提供申請專利範 圍第6項之乙烯醚固化性組合物,其包含的上述磷系難燃劑 94949·丨 000421.doc 1344477 為下述一般式(II)所示的化合物: [化2]
另外,關於申請專利範圍第8項
㈧、VC Ί穴丫 e耳号不·』摩U 圍第1〜7中任一項之乙烯醚固化性組合物,其中混合了多價 環氧化合物。 另外’關於申晴專利範圍第9項的發明係提供一種預浸材 料,其採用申請專利範圍第丨〜8中任一項之乙烯醚固化性紐 合物而形成。 發明的效果 藉由由多價乙烯醚化合物及多價酚化合物所形成的本發 明之乙稀_固化性組合物,能形成相對介電常數小的固化 物,而使積體電路的微細化成爲可能。 【實施方式】 以下對本發明加以詳細説明(以下,"本發明"—詞意味著 與申請專利範圍第卜8有關的發明中W種以上)。 本發明的乙_固化性組合物所採用的多價乙稀醚化合 物並無限制。例如多價醇或多價酚的乙烯醚衍生物。該多 價醇有乙二醇、% —結 一醇、四甲二醇、新戊二醇、甘油、三 94949-1000421.doc 1344477 羥甲基丙炫 '季戊四醇、二季戊四酵、1,4-環己二曱醇、2,2» 二(4-(2-羥乙氧)苯基)丙烷等的多價酚的環氧乙烷、環氧丙 烷的加成物等。該多價酚有對苯二酚、二苯酚A、二苯酚ρ、 二苯酚S、1,1,2,2-四(4-羥苯基)乙烷、1,3,5 -三(4-羥苄 基)-1,3,5-三氮雜笨_2,4,6_三酮、1,1,3-三(4-羥苯基)丁烷、 苯酚酚醛樹脂、甲苯酚酚醛樹脂等的酚樹脂。上述多價乙 烯醚化合物如為4價以上的多價乙烯醚化合物時,可以獲得 玻璃轉化溫度高的固化物,較爲理想。 上述多價乙烯醚化合物的具體例有下述化合物 No_ l~No.5。但是本發明並不被以下的化^合物限制。另外, 下述化合物No.4中的n,代表數字hwooo。 [化3] 化合物No. 1
94949-1000421.doc 1344477 [化5] 化合物Ν ο.: n—c=CH2 0—C=CHj C=CHt 巧· •c—p—c一 0—c—c—c—c H| CHfH| Hz 〇一G=CH| 〇—C^CHj [化6] 化合物N o. 4
c-«I
[化7] 化合物No.:
-10- 94949-1000421.doc e 1344477 本發明的乙_固化性組合物所使料上述多價酚化合 物’有對苯二盼、二苯紛a、二笨酚F、二苯酚s、mi :(4·經苯基)乙烧、U5·三(4_經爷(苯甲)基)^3,5^氣雜 苯2,4,6-二酮、1,1,3-二(4-羥笨基)丁烷、苯酚酚醛樹脂、曱 笨酚酚醛樹脂等的酚樹脂。其中酚樹脂,特別是上述一般 式⑴所示的酚樹脂所得的固化物之機械強度好,較爲理想。 上述多價酚化合物的具體例有下述化合物N〇.6〜N〇 9。但 疋本發明並不被以下的化合物所限制。 [化8] 化合物No.6
[化9] 化合物No.7
94949-1000421.doc -11 - “44477 [化 10] 化合物No. 8
[化 11] 化合物No. 9
本發明的乙烯ϋ固化性組合物中,上述多價盼化合物的 混合量為相對於上述多價乙_化合物1〇〇重量》,其重量 分為30.重量分較爲理想,5〇〜15〇重量分時更爲理想。 =的乙_固化性組合物可根據必要,混和多價環 聽5物、環氧樹脂固化劑、填充材料、難燃劑等。 作爲上述多價環氧化合物, ―化合物、_環氧化合物等。::::香: 94949-1000421.doc -J2- 1344477 氧化物:例如有對笨二盼、間苯二龄、二苯盼A、二苯紛ρ、 Μ 一羥基一本、酚醛樹脂、目溴二苯酚八、2,二㈠-羥笨 基)-1,1,1,3,3,3-六氟丙燒等多價盼的甘油喊化合物。 述月S環族環乳化合物例如有,$少古 1U有至少有一個以上的脂肪環的 夕價醇的聚甘油喊,或者含有環己烯或環戊稀環的化人 物,經氧化劑進行環氧化而得到含有環己稀氧化物或環: 稀氧化物的化合物。作爲代表例,有氫添加二苯紛A二甘油 醚2,2-一(3,4-環乳環己基)丙院、3,4-環氧環己基甲基^心 環氧環己酸酯、3,4-環氧^甲萁搭p甘, ’ 衣虱1-甲基裱己基_3,4_環氧_丨_甲基己 酸S旨、6 -甲基- 3,4 -環氧j罗p技田# # 虱衣己基甲基-6-甲基_3,4_環氧環己酸 酯、3,4_環氧-3 -甲基環p A田# < T丞袁己基甲基_3,4_環氧_3·甲基環己酸 酉旨、3,4 -環氧-5-▼基規ρ |田Λ 裒己基甲基_3,4_環氧_5_甲基環己酸 醋、二(3,4_環氧環己基甲基)己二酸醋、次甲基二(3,4_環己 院)' 2,2-二(3,4-環氧環己基)丙烧、二環戊二稀二環氧化 物次乙基一(3,4-環氧環己酸醋)、環氧六氯鄰苯二甲酸二 辛醋、環氧六氫鄰笨二甲酸二-2-乙基己醋等。作爲上述脂 肪族環氧化合物’有脂肪族多價醇或其婦氧化加成物的聚 甘㈣、脂肪族長鏈多驗基酸的聚甘油醋、由甘油丙稀酸 S旨或甘油曱基丙烯駿酷的7 真 外政自曰的乙烯聚合而合成的單聚物、由甘 油丙稀酸醋或甘油甲基丙稀酸g旨和其他的乙稀單體的乙稀 聚合而合成的共聚物等。作爲代表性化合物,有Μ·丁二醇 —甘油、1,6 ·己二醇-廿、、上 择一甘油鱗、甘油的三甘油謎、三經曱 基丙烷的三甘油醚、山梨醇的四甘油醚、二季戊四酵的六 甘油醚、聚乙烯甘油醇的二甘油_、聚丙稀甘油酵的二甘 94949-1000421.doc •13- 油喊等多價醇之甘㈣,此外,由丙料油醇、三經甲基 丙:、甘油等脂肪族多價醇中1種或2種以上的烯氧化物加 、得i的聚㈣聚醇的聚m脂肪族長鏈二驗基酸之二 甘:“日豸有脂肪族高級醇的單甘油醚、苯酚、甲苯酚、 + 另外這些物質與烯氧化物加成而得到的聚醚醇的 單甘油鰱、高級脂肪酸甘油酯、環氧化大豆油、環氧化硬 月曰酸辛8a、環氧化硬脂酸丁 ^旨、環氧化聚丁二稀等。 作爲上述環氧樹脂固化劑,有潛在性固化劑、聚胺化合 物、聚苯酚化合物和陽離子型光起始劑(P-Ο等。 作爲上述潛在性固化劑,有二氰基二醯胺、醯肼、咪唑 化σ物、胺加合物、錡鹽、鏽鹽、酮亞胺沐⑷以丨加)、酸酐、 叔胺等。这些潛在性固化劑,能提供一液型的固化性組合 物,容易處理’較爲理想。 作爲上述酸酐,例如有鄰苯二甲酸酐、偏苯三酸酐、均 苯四酸酐、四氫鄰苯二曱酸酐、六氫鄰苯二甲酸酐、馬來 酸針、號轴酸肝、2,2-二(3,4-二羧苯基)-1,1,1,3,3,3-六氟丙 烷二酸酐等。 作爲上述聚胺化合物’例如有乙二胺、二乙三胺、三乙 四胺等脂肪族聚胺,mencene二胺、異佛爾酮二胺、二(4_ 胺基-3-曱環己基)曱烷、二(胺甲基)環己烷、3,9_二(3_胺丙 基)2,4,8,10-四氧螺[5,5]十一烷等脂環族聚胺 ,m-苯二曱胺 等具有芳香環的脂肪胺,m-亞苯二胺、2,2-二(4-胺苯基)丙 烧、一胺基二苯基甲院、二胺基二苯續酸、α,α_: (4_胺苯 基)-Ρ-二異丙苯、2,2-二(4-胺苯基)-^1,3,3,3-六氟丙烷等 94949-1000421.doc -14- 1344477 芳香族聚胺。 · 作爲上述聚盼化合物,例如有苯紛盼酸樹脂、〇_甲苯盼 酚醛樹脂、t-丁笨酚酚醛樹脂、二環戊二烯甲苯酚、松烯二 笨紛、松烯二兒茶酚、H3-三(3-叔丁基-4-羥-6-甲苯基) 丁烧、丁亞稀一(3-叔丁基-4 -經_6_甲苯基)、2,2 -二(4·經笨 基)-1,1,1,3,3,3-六氟丙烷等。其中笨酚酚醛樹脂所得到的固 化物的電特性和機械強度適用於積層板。 上述陽離子型光起始劑是一種經能量射線照射後能釋放 出使陽離子聚合開始的物質的化合物。特別理想的為經能 j 量射線照射後釋放出路易斯酸的鏽鹽的複鹽或者其衍生 物。代表性的化合物有一般式[A]m + [B]W-所表示的陽離子和 陰離子所組成的鹽。 防離子[A]m+為鏽較 [(RlQ]1^。 在此,R1為碳的數目丨〜的,亦可為含有碳原子以外的若 干個原子的有機基。4 i〜5的整數。^⑽各自獨立,可相 同亦可不同,至少一個為含有芳香環的上述有機基較爲理 想。Q為 S、N、Se、Te、P、As、Sb、出、〇、工、b 〇 F以及㈣中選擇出的原子或原子團。另外,陽離:二 的上述—般娜^Γ+中的Q的原子價如為q時,必 須滿足m=a-q的關係式(其中N=N的原子價作爲〇處 另外,陰離子心為“物複合物較爲理想 表示為一般式[LXb]所。 …,、口構了 在此,L為齒化物複合物的中心肩 35 4者頰金屬(或 94949-I000421.doc •15· 1344477 半金屬)(或類金屬’ Metalloid),可為B、p、As、Sb、Fe、 Sn、Bi、A卜 Ca、In、Ti、Zn、Sc、v、&、Mn、c〇等。χ 為鹵原子。b為3〜7的整數。另外,陰離子[B]w-所表示的上 述一般式[LXb]w中的L的原子價如為卩時,必須滿足m=b_p • 的關係式。 上述一般式[LXb]w所表示的陰離子的具體例有四氟化硼 陰離子(BF4)·、六氟化磷陰離子(PF6)-、六氟化銻陰離子 (SbFe)、六氟化砷陰離子(AsF6)-、六氣化銻陰離子(sbF6)·等。 ^ 另外陰離子[B] ^具有一般式[LXb-1(〇H)]^所表示結構 亦可。L、X以及b與上述一般式[LXb]W-中的相同。又,陰 離子[ΒΓ還包括過氣酸根離子(cl〇4).、三氟曱基亞硫酸根 離子(CFsSO3)·、氟磺酸根離子(FS〇3)-、曱苯磺酸陰離子、 三硝基苯磺酸陰離子等。 鏽鹽之中,使用下述1)〜3)的芳香族鏽鹽特別有效。可從 中選擇1種單獨使用或者2種以上混合使用。 ‘ 丨)苯二重氮六氟化磷、4-甲氧苯二重氮六氟化銻、扣甲 苯二重氮六氟化磷等的芳基二重氮鹽。 2) 二苯基碘銪六氟化銻、二(4_甲苯基)碘鏽六氟化磷、 二(4-tert· 丁苯基)碘鏽六氟化磷等的二芳基碘鏽鹽。 3) 二苯基銃六苯氟化銻、三(4_甲氧苯基)毓六氟化磷、 二苯基-4-硫苯氧基銃六氟化銻、二苯基_4_硫苯氧苯基錡> 氟化磷、4,4,-二(二苯基鎳)苯基硫_二_六氟化銻、4,4,_二(二 苯基銃)苯基硫-二-六氟化磷、4,4,-二[二(β_羥乙氧)苯鉼] 苯基硫-二-六氟化銻、4,4|·二[二(|3_羥乙氧)苯鎳]苯基硫_ -16 - 94949-1000421.doc 1344477 二-六敦化鱗、4·[4’_(安息香醜)苯硫]苯基_二_(4_氟苯基)錢 六敗化娣、4_[4|_(安息香醜)苯硫]苯基-二_(4_氣苯基)鎮六 氟化磷等的三芳基錆鹽。 、 另外,除1)〜3)外,其他適用的#(η5_2,4_ 基卿,3,4,5,6-仰_甲基乙基)朴鐵_六氟化料的1 方香烴錯合物、三(乙酿丙剩基)链 '三(乙基丙綱乙酸根) 紹、二(水揚酸)銘等的紹鹽合物與三苯基石夕醇等的石夕醇類混 合物。 這些之中,從實用面和光感度的觀點考慮,使用芳香族 蛾鏽鹽、芳香族銃鹽、鐵·芳香烴錯合物較爲理想。 這些光起始劑,將安息香酸類或者叔胺類等衆所周知的 先聚合促進劑的!種或2種以上組合使用亦可。上述光❹ 劑的混合量在本發明的乙_固化性組合物中為^,重 量%較爲理想。未達(Μ重量%則有時得不到添加效果多 於30重量%則有會降低@化物的機械強度。 使用上述光起始劑時,用於聚合的光源有高壓汞燈、金 屬函素燈、I燈等衆所周知光源。在紫外線、電子線、X 線、放射線、高頻等的活性能量射線的照射下,從上述光 起始劑中放出路易斯酸’從而使上述多價環氧化合物固 化。作爲上述光源,具備· nm以下的波長的光源均有效。 包含前述多價乙㈣化合物以及前述多㈣化合物的本 發明乙烯醚固化性組合物的固化方法,與先前衆所周知的 環私樹脂等的固化方法相同’使用熱硬化的方法。 用前述多價環氧化合物時’作爲環氧樹脂的固化技: 94949-l〇〇〇421.do, 1344477 周知的有採用胺類固化劑、酸酐類固化劑等固化劑進行固 化、採用固化催化劑的自身聚合進行固化、採用光起始劑 進行光固化以及合併使用固化促進劑控制固化速度。 前述多價環氧化合物的種類和使用量等,可根據固化物 用途不同而適當選擇。由於前述多價酚化合物作爲前述多 價乙烯醚化合物以及前述多價環氧化合物兩者的固化劑而 發揮作用,所以前述多價環氡化合物的使用量在使用多價 乙烯醚化合物能得到介電常數低的特徵的範圍内,在前述 I 多價乙烯醚化合物基準下,選擇5〜1〇〇重量較爲理想, 10〜50重量%更爲理想,10〜30重量%最爲理想。 别述環氧樹脂固化劑的使用量並無特別限制。通常採用 使前述多價環氧化合物的全環氧莫耳數和前述環氧樹脂固 化劑的官能基數的比為0·9/ι·0〜1〇/〇 9的量。其中所使用的 環氧樹脂固化劑也與前述多價酚化合物反應而形成固化物 時,相對於多價乙烯醚化合物1〇〇重量分,多價酚化合物為 ^ 30〜200重量分的範圍内,多價乙烯醚化合物的一部分由環 氧樹脂固化劑代替亦可。 本發明乙烯醚固化性組合物採用的理想的填充材料有玻 璃纖維、硼酸鋁強化水晶(鬚晶)、氮化硼強化水晶等纖維狀 填充材料,二氧化矽、氧化鋁等球狀填充材料等。該纖維 狀填充材料可根據用途適當選擇長軸方向的長度及外觀比 等,該球狀填充材料為正球狀,粒徑小的較爲理想。 上述填充材料的混合量為相對於前述多價乙烯醚化合物 100重量分,其重量分爲10〜3000較爲理想,2〇〜2〇〇重量分 94949-1000421.doc
S -18- 1J44477 更爲理想。特別是填充材料為二氧化石夕時,相對於前述多 價乙烯醚化合物的混合量和前述多價酚化合物的混合量總 汁100重量分,二氧化梦的混合量在10〜1卿重量分較爲理 想’ 20〜100重量分更爲理想。 本發明乙稀醚固化性組合物採用的難燃劑並無特別限 制。例如有函系、磷系、無機系等難燃劑。其中環境負荷 小的鱗系難燃劑,特別是能與環氧化合物反應的前述一般 式(Π)所表示的化合物,因其使用時樹脂的玻璃轉化溫度等 機械特性降低較小,較爲理想。 上述難燃劑的混合量相對於前述多價乙稀_化合物⑽ 重量分,H)〜200重量分較爲理想,1〇〜1〇〇重量分更爲理相。 特別是難燃劑為上述填系難燃劑時,相對於前述多價乙烯 縫化合物的混合量與前述多價紛化合物的混合量總物 重量分,磷系難燃劑的混合量為1〇〜5〇重量分較爲理想, 10〜30重量分更爲理想。 上述難燃劑單獨使用亦可,2種以上的難燃劑合用亦可, 與聚四氣乙烯、聚石夕氧烧等的防漏劑,錄化合物,密胺等 的難燃助劑合用亦可。 實施例
以下通過實施例及比較例,更具體的說明本發明。本發 明係不受以下的實施例限制。 X
[實施例1〜5及比較例1 ] 按表^中記載的配比製備固化性組合物,該固化性組合物 係在刚。C保持H、時,2〇(TC保持i小時,再於㈣力保❸ 94949-1000421.doc -19- 1344477 小時,從而得到固化物。所得固化物的性能(玻璃轉化溫 度、相對介電常數、介電正切、吸水率及難燃性)用下述方 法進行測定。另外難燃劑是按最終固化性組合物的磷含有 量為1重量%來進行混合的。 • (測定方法) •玻璃轉化溫度:以動態黏彈性法測定。 •相對介電常數及介電正切:用材料分析儀HP-4291B(安 捷倫科技公司製)測定。 ^ •吸水率:室溫下在蒸餾水中浸泡24小時,將浸泡後的重 量增加率作爲吸水率。 •難燃性:基於UL-94進行測定。 玻璃轉化溫度、相對介電常數、介電正切及吸水率的測 定結果在表1中列出。難燃性在所有的試驗片中均為V-0。 [表1] 實施例1 實施例2 實施例3 實施例4 實施例5 比較例1 多價乙烯醚化合物 化合物No. 1 100 化合物No.2 100 化合物No.3 100 化合物No.4 100 化合物No.5 100 環氡化合物 比較化合物Γ 100 多價酚化合物 酚Γ2 62.1 32.0 143 74.2 30.9 酚2·3 62.1 32.0 126.7 30.9 無定形二氧化硅” 12.4 9.1 13.5 9.7 12.6 9.0 球狀二氧化硅” 37.3 27.3 40.4 29.0 37.7 26.9 難燃劑% 24.3 17.9 26.2 18.9 24.6 17.5 溶劑1 100 100 100 200 200 100 固化催化劑_8 7.1 3.8 10.1 5.4 5.6 3.7 玻璃轉化溫度(°c) 125 135 210 200 180 130 比介電常數(2GHz) 2.9 3.0 2.8 2.9 2.8 3.5 節電正切(2GHz) 0.009 0.010 0.008 0.007 0.006 0.200 吸水率(wt%) 0.25 0.20 0.30 0.20 0,15 1.50 94949-1000421.doc -20-
S 1344477 *1 :二笨盼A二甘油醚 *2 :住友Bakelite(株)製:PR-53194 *3 :三井化學(株)製:MireksXLC-LL *4 :日本Aerosi】(株)製:Aerosil 200 *5 : SO-E5 :株式會社Admatechs *6 :
*7 :乙二酵丁醚醋酸酯 *8 : 2·乙基-4-甲基咪唑 由包含多價乙烯醚化合物及多價酚化合物的乙稀趟固化 性組合物而得到的固化物(實施例1〜5)與由環氧樹脂固化 性組合物而得到的固化物(比較例1)相比,前者相對介電常 數及介電正切小且吸水率低。顯然本發明的乙烯醚固化性 組合物適用於積層板等電子部件。另外作爲多價乙稀謎化 合物,在用4價以上的多價乙烯醚化合物時(實施例3〜5), 可以得到玻璃轉化溫度高,電特性及機械特性更好的固化 物。 94949-1000421.doc •21 -
Claims (1)
- 、申請專利範圍: 1· 一種乙烯醚固化性組合物,其係由多價乙烯醚化合物100 重量分及多價盼化合物30〜200重量分,與填充材料 10〜3000重量分及難燃劑10〜200重量分混合而成者;其 中,該多價乙烯醚化合物為多價醇或多價酚之乙烯醚衍 生物。 2·如請求項1之乙烯醚固化性組合物,其中上述多價乙稀醚 化合物為4價以上的多價乙烯醚化合物。 3.如請求項1或2之乙烯醚固化性組合物,其中上述多價盼 化合物為下述一般式(I)所示的酚樹脂: [化1](式中η代表0或者1,m代表1〜1〇〇〇〇)。 4_如請求項1或2之乙烯醚固化性組合物,其係由上述多價 乙烯醚化合物之混合量及上述多價酚化合物的混合量總 計1〇〇重量分,與作為上述填充材料之二氧化矽1〇〜1〇〇〇 重量分混合而成者。 5.如請求項1或2之乙烯醚固化性組合物,其係由上述多價 乙烯醚化合物之混合量及上述多價酚化合物的混合量總 計100重量分,與作為上述難燃劑之磷系難燃劑1〇〜5〇重 94949-1000421.doc 1344477 量分混合而成者。 6.如請求項5之乙烯_固化性組合物’其中上述鱗系難燃劑 為下述一般式(II)所示的化合物: [化2]8.如請求項1或2之乙烯醚固化性組合物 環氧化合物者。 一種預浸材料,其特徵在於使用請求 化性組合物而形成者。 其係混合有多價 項1或2之乙烯醚固94949-1000421.doc
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003278953A JP4514418B2 (ja) | 2003-07-24 | 2003-07-24 | ビニルエーテル硬化性組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW200517429A TW200517429A (en) | 2005-06-01 |
TWI344477B true TWI344477B (zh) | 2011-07-01 |
Family
ID=34100794
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW093122161A TW200517429A (en) | 2003-07-24 | 2004-07-23 | Vinyl ether curing composition |
Country Status (6)
Country | Link |
---|---|
US (1) | US7595357B2 (zh) |
EP (1) | EP1650259B1 (zh) |
JP (1) | JP4514418B2 (zh) |
KR (1) | KR101064788B1 (zh) |
TW (1) | TW200517429A (zh) |
WO (1) | WO2005010098A1 (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0817795D0 (en) * | 2008-09-30 | 2008-11-05 | 3M Innovative Properties Co | Fast curing oil-uptaking epozxy-based structural adhesives |
JP5360508B2 (ja) * | 2011-03-18 | 2013-12-04 | 日立化成株式会社 | 樹脂組成物およびそれを用いたプリプレグ、印刷配線板 |
US9766378B2 (en) * | 2014-09-26 | 2017-09-19 | Fujifilm Corporation | Optical film, polarizing plate equipped with the optical film, liquid crystal display device, and method for producing an optical film |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1089871A (en) * | 1964-01-03 | 1967-11-08 | Canadian Ind | Foams from vinyl ether prepolymers |
JP3038062B2 (ja) | 1991-10-15 | 2000-05-08 | 旭電化工業株式会社 | 冷凍機用潤滑剤 |
US6121358A (en) * | 1997-09-22 | 2000-09-19 | The Dexter Corporation | Hydrophobic vinyl monomers, formulations containing same, and uses therefor |
JP3933294B2 (ja) | 1998-03-06 | 2007-06-20 | 株式会社Adeka | 硬化性組成物 |
US6211320B1 (en) * | 1999-07-28 | 2001-04-03 | Dexter Corporation | Low viscosity acrylate monomers formulations containing same and uses therefor |
US6627704B2 (en) * | 1999-12-01 | 2003-09-30 | General Electric Company | Poly(arylene ether)-containing thermoset composition, method for the preparation thereof, and articles derived therefrom |
JP2002313841A (ja) * | 2000-04-14 | 2002-10-25 | Namics Corp | フリップチップ実装方法 |
JP4548901B2 (ja) * | 2000-06-14 | 2010-09-22 | 株式会社Adeka | 難燃性エポキシ樹脂組成物 |
JP3948646B2 (ja) * | 2000-08-31 | 2007-07-25 | 東京応化工業株式会社 | ポジ型レジスト組成物及びそれを用いたレジストパターン形成方法 |
US6667194B1 (en) * | 2000-10-04 | 2003-12-23 | Henkel Loctite Corporation | Method of bonding die chip with underfill fluxing composition |
TW574739B (en) * | 2001-02-14 | 2004-02-01 | Nitto Denko Corp | Thermosetting resin composition and semiconductor device using the same |
JP4721309B2 (ja) * | 2001-02-14 | 2011-07-13 | 日東電工株式会社 | 熱硬化性樹脂組成物および半導体装置 |
JP2003026784A (ja) * | 2001-07-18 | 2003-01-29 | Yokohama Rubber Co Ltd:The | 硬化性樹脂組成物および接合部材の易解体方法 |
JP2003082061A (ja) * | 2001-09-10 | 2003-03-19 | Asahi Denka Kogyo Kk | 硬化性組成物 |
JP3955234B2 (ja) * | 2001-09-28 | 2007-08-08 | 日東電工株式会社 | 熱硬化性樹脂組成物およびそれを用いた半導体装置 |
-
2003
- 2003-07-24 JP JP2003278953A patent/JP4514418B2/ja not_active Expired - Fee Related
-
2004
- 2004-07-15 US US10/560,815 patent/US7595357B2/en not_active Expired - Fee Related
- 2004-07-15 EP EP04747561.1A patent/EP1650259B1/en not_active Expired - Fee Related
- 2004-07-15 KR KR1020057024945A patent/KR101064788B1/ko active IP Right Grant
- 2004-07-15 WO PCT/JP2004/010095 patent/WO2005010098A1/ja active Application Filing
- 2004-07-23 TW TW093122161A patent/TW200517429A/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
JP4514418B2 (ja) | 2010-07-28 |
KR20060038951A (ko) | 2006-05-04 |
EP1650259B1 (en) | 2015-07-15 |
US7595357B2 (en) | 2009-09-29 |
EP1650259A4 (en) | 2006-07-19 |
US20060178454A1 (en) | 2006-08-10 |
JP2005154448A (ja) | 2005-06-16 |
WO2005010098A1 (ja) | 2005-02-03 |
EP1650259A1 (en) | 2006-04-26 |
KR101064788B1 (ko) | 2011-09-14 |
TW200517429A (en) | 2005-06-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR102334119B1 (ko) | 광경화성 에폭시 수지 시스템 | |
JP5663874B2 (ja) | エポキシ樹脂組成物、その硬化物及び発光ダイオード | |
TWI384028B (zh) | Epoxy resin hardening composition | |
JP4986485B2 (ja) | エポキシ樹脂硬化性組成物 | |
TW201211160A (en) | Curable composition | |
TW201231545A (en) | Curable epoxy resin composition and optical semiconductor device using the same | |
TW201238977A (en) | Curable composition and cured article | |
JP2008081596A (ja) | 透明樹脂組成物 | |
TW201217421A (en) | Production method for curing articles and curing articles | |
TWI730065B (zh) | 環氧化合物、硬化性組合物、硬化物、環氧化合物之製造方法及反應性稀釋劑 | |
JP2021161126A (ja) | 活性エネルギー線重合性組成物、3次元造形用組成物及び硬化物 | |
TWI344477B (zh) | ||
TW202246411A (zh) | 硬化性組合物及其硬化物 | |
TW200815385A (en) | Acid anhydride ester and composition thereof, and heat-curable resin composition and cured product thereof | |
TW201339237A (zh) | 透明電路基板用環氧樹脂組成物及層合玻璃片 | |
JP4392096B2 (ja) | カチオン重合性樹脂組成物 | |
JP5213547B2 (ja) | エポキシ基含有エステル化合物を含む硬化性組成物、該組成物の製造方法およびエポキシ基含有エステル化合物 | |
JP2008007566A (ja) | 新規化合物、エポキシ樹脂組成物及びその硬化物 | |
JP2021031636A (ja) | 不飽和ポリエステル樹脂組成物、及びその硬化物 | |
JP4759793B2 (ja) | エポキシ樹脂組成物及び光半導体用封止剤 | |
JP4243980B2 (ja) | 2,2−ビス(3,4−エポキシシクロヘキシル)−1,1,1,3,3,3−ヘキサフルオロプロパン及び該化合物を用いたエポキシ樹脂組成物 | |
JP6264295B2 (ja) | エポキシ樹脂組成物、その硬化物および発光ダイオード | |
TW201237058A (en) | Epoxy resin compositions comprising epoxy and vinyl ester groups | |
JP2011089059A (ja) | エポキシ樹脂組成物、該エポキシ樹脂組成物を用いた電気絶縁線輪および回転電機の製造方法 | |
JP2021031658A (ja) | 光カチオン重合性組成物、光造形用組成物及び硬化物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | Annulment or lapse of patent due to non-payment of fees |