CA1106992A - Melanges complexes renforces et contenant une resine du type friedel-crafts - Google Patents

Melanges complexes renforces et contenant une resine du type friedel-crafts

Info

Publication number: CA1106992A
Authority: CA; Canada
Prior art keywords: friedel; group; resin; compound; composites
Prior art date: 1977-07-11
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA307,031A

Other languages

English (en)

Inventor

George E. Green

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Schweiz AG

Original Assignee

Ciba Geigy Investments Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-07-11

Filing date

1978-07-07

Publication date

1981-08-11

1978-07-07 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1981-08-11 Application granted granted Critical

1981-08-11 Publication of CA1106992A publication Critical patent/CA1106992A/fr

Status Expired legal-status Critical Current

Links

229920005989 resin Polymers 0.000 title claims abstract description 59
239000011347 resin Substances 0.000 title claims abstract description 59
238000005727 Friedel-Crafts reaction Methods 0.000 title claims abstract description 44
239000002131 composite material Substances 0.000 title claims abstract description 27
-1 aralkyl alkyl ethers Chemical class 0.000 claims abstract description 51
150000001875 compounds Chemical class 0.000 claims abstract description 47
239000000203 mixture Substances 0.000 claims abstract description 32
150000002989 phenols Chemical class 0.000 claims abstract description 22
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 19
239000003795 chemical substances by application Substances 0.000 claims abstract description 19
229920003986 novolac Polymers 0.000 claims abstract description 12
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 38
125000003118 aryl group Chemical group 0.000 claims description 19
239000012779 reinforcing material Substances 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000001931 aliphatic group Chemical group 0.000 claims description 9
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
239000000178 monomer Substances 0.000 claims description 8
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
150000003254 radicals Chemical class 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 5
150000002430 hydrocarbons Chemical group 0.000 claims description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
230000021615 conjugation Effects 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 claims description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
235000005513 chalcones Nutrition 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 3
230000005494 condensation Effects 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
JUKHVNMXKSHNQY-UHFFFAOYSA-N penta-3,4-dien-2-one Chemical group CC(=O)C=C=C JUKHVNMXKSHNQY-UHFFFAOYSA-N 0.000 claims description 3
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 3
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 3
DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 claims description 3
CYWSDGUZWKUALI-UHFFFAOYSA-N 3-azidocoumarin Chemical compound C1=CC=C2OC(=O)C(N=[N+]=[N-])=CC2=C1 CYWSDGUZWKUALI-UHFFFAOYSA-N 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 2
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052740 iodine Chemical group 0.000 claims description 2
235000021286 stilbenes Nutrition 0.000 claims description 2
150000001555 benzenes Chemical class 0.000 claims 2
239000007788 liquid Substances 0.000 abstract description 12
239000000835 fiber Substances 0.000 abstract description 9
230000005855 radiation Effects 0.000 abstract description 9
238000013007 heat curing Methods 0.000 abstract description 8
239000007787 solid Substances 0.000 abstract description 8
229920000647 polyepoxide Polymers 0.000 abstract description 7
239000003677 Sheet moulding compound Substances 0.000 abstract description 2
238000007493 shaping process Methods 0.000 abstract 1
238000001723 curing Methods 0.000 description 18
238000000034 method Methods 0.000 description 17
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
239000003054 catalyst Substances 0.000 description 13
239000000126 substance Substances 0.000 description 13
230000002787 reinforcement Effects 0.000 description 11
229910052799 carbon Inorganic materials 0.000 description 10
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
239000000463 material Substances 0.000 description 9
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
238000010438 heat treatment Methods 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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 7
150000002118 epoxides Chemical group 0.000 description 7
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 6
239000011342 resin composition Substances 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
229960004279 formaldehyde Drugs 0.000 description 5
239000011521 glass Substances 0.000 description 5
VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000001252 acrylic acid derivatives Chemical class 0.000 description 4
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000004744 fabric Substances 0.000 description 4
235000019256 formaldehyde Nutrition 0.000 description 4
150000002334 glycols Chemical class 0.000 description 4
235000010299 hexamethylene tetramine Nutrition 0.000 description 4
239000004312 hexamethylene tetramine Substances 0.000 description 4
229960004011 methenamine Drugs 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-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
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000012965 benzophenone Substances 0.000 description 3
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
229910001507 metal halide Inorganic materials 0.000 description 3
150000005309 metal halides Chemical class 0.000 description 3
YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 3
238000000465 moulding Methods 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
235000013824 polyphenols Nutrition 0.000 description 3
238000003825 pressing Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000004804 winding Methods 0.000 description 3
WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 2
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
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KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
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150000001298 alcohols Chemical class 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
239000004760 aramid Substances 0.000 description 2
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
229920003235 aromatic polyamide Polymers 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
JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 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 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
150000008366 benzophenones Chemical class 0.000 description 2
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
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KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000005281 excited state Effects 0.000 description 2
239000002657 fibrous material Substances 0.000 description 2
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
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VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
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IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
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VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
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XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
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239000010453 quartz Substances 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
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229940075554 sorbate Drugs 0.000 description 2
125000001174 sulfone group Chemical group 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
229910052721 tungsten Inorganic materials 0.000 description 2
239000010937 tungsten Substances 0.000 description 2
JHSWQUGEBUSRNO-UHFFFAOYSA-N (2-hydroxy-3-prop-2-enoyloxypropyl) propanoate Chemical compound CCC(=O)OCC(O)COC(=O)C=C JHSWQUGEBUSRNO-UHFFFAOYSA-N 0.000 description 1
GRTWTVFDPBKQNU-MQQKCMAXSA-N (2e,4e)-hexa-2,4-dienoyl chloride Chemical compound C\C=C\C=C\C(Cl)=O GRTWTVFDPBKQNU-MQQKCMAXSA-N 0.000 description 1
AZNUOOZUBQUQJV-UHFFFAOYSA-N (3-butoxy-2-hydroxypropyl) prop-2-enoate Chemical compound CCCCOCC(O)COC(=O)C=C AZNUOOZUBQUQJV-UHFFFAOYSA-N 0.000 description 1
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
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229920002492 poly(sulfone) Polymers 0.000 description 1
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239000004417 polycarbonate Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
FOKZHJCFBNVOAV-UHFFFAOYSA-N propyl 2-hydroxy-3-phenoxyprop-2-enoate Chemical compound CCCOC(=O)C(O)=COC1=CC=CC=C1 FOKZHJCFBNVOAV-UHFFFAOYSA-N 0.000 description 1
229940079877 pyrogallol Drugs 0.000 description 1
230000003014 reinforcing effect Effects 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229910010271 silicon carbide Inorganic materials 0.000 description 1
HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
238000001029 thermal curing Methods 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
238000004448 titration Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1

Landscapes

Reinforced Plastic Materials (AREA)

CA307,031A 1977-07-11 1978-07-07 Melanges complexes renforces et contenant une resine du type friedel-crafts Expired CA1106992A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB28948/77		1977-07-11
GB2894877		1977-07-11

Publications (1)

Publication Number	Publication Date
CA1106992A true CA1106992A (fr)	1981-08-11

Family

ID=10283783

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA307,031A Expired CA1106992A (fr)	1977-07-11	1978-07-07	Melanges complexes renforces et contenant une resine du type friedel-crafts

Country Status (1)

Country	Link
CA (1)	CA1106992A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN115141305A (zh) *	2022-07-06	2022-10-04	中国科学院赣江创新研究院	一种功能性聚合物及制备方法、及利用其制备离子印迹聚合物的方法

1978
- 1978-07-07 CA CA307,031A patent/CA1106992A/fr not_active Expired

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN115141305A (zh) *	2022-07-06	2022-10-04	中国科学院赣江创新研究院	一种功能性聚合物及制备方法、及利用其制备离子印迹聚合物的方法
CN115141305B (zh) *	2022-07-06	2023-09-19	中国科学院赣江创新研究院	一种功能性聚合物及制备方法、及利用其制备离子印迹聚合物的方法

Legal Events

Date	Code	Title	Description
1998-08-11	MKEX	Expiry

Publication	Publication Date	Title
US4254012A (en)	1981-03-03	Reinforced composites containing cyanato resins
US4092443A (en)	1978-05-30	Method for making reinforced composites
US4299938A (en)	1981-11-10	Photopolymerizable and thermally polymerizable compositions
US4252593A (en)	1981-02-24	Method of preparing reinforced composites
CA1300307C (fr)	1992-05-05	Photopolymerisation a l'aide de sels organometalliques
US4339567A (en)	1982-07-13	Photopolymerization by means of sulphoxonium salts
CA1157600A (fr)	1983-11-22	Compositions a teneur d'epoxy, et leur polymerisation
CA1095850A (fr)	1981-02-17	Bonderiser deux surfaces en exposant un compose epoxydique liquide a des radiations actiniques
CA1293835C (fr)	1991-12-31	Composition durcissable, et son emploi
US4439291A (en)	1984-03-27	Acrylate-containing compositions and their polymerization
CA1183038A (fr)	1985-02-26	Methode de formation d'images a l'aide d'une composition refermant une resine epoxyde, une polyamine benzenique, et un produit aromatique, precurseur d'acide
CA1209741A (fr)	1986-08-12	Compositions photopolymerisables renfermant des sels de diaryliodosyle
US4074008A (en)	1978-02-14	Epoxide resins
JPS625180B2 (fr)	1987-02-03
US4276352A (en)	1981-06-30	Reinforced composites containing unsaturated polyimide resins
CA1163852A (fr)	1984-03-20	Obtention d'image a l'aide d'une composition de protection positive contenant un produit generateur de pellicule avec un groupement benzoine substitue sur la chaine principale
CA1136340A (fr)	1982-11-23	Polymerisation de substances contenant des hydroxyles
JPS60135402A (ja)	1985-07-18	重合性組成物
EP0097012B1 (fr)	1987-04-08	Résines photodurcissables et leur utilisation
CA1084870A (fr)	1980-09-02	Composes renforces
CA1106992A (fr)	1981-08-11	Melanges complexes renforces et contenant une resine du type friedel-crafts
JPS60184518A (ja)	1985-09-20	硬化可能な組成物及びその使用法
JPH0245641B2 (ja)	1990-10-11	Hikarijugoseisoseibutsuoyobisonojugoho
GB1570991A (en)	1980-07-09	Epoxy resin impregnated preparegs
JPS60124622A (ja)	1985-07-03	光重合性組成物及び重合性または架橋性材料の製造方法