NO823043L - Cyclopentadienderivater og fremstilling og anvendelse derav - Google Patents
Cyclopentadienderivater og fremstilling og anvendelse deravInfo
- Publication number
- NO823043L NO823043L NO823043A NO823043A NO823043L NO 823043 L NO823043 L NO 823043L NO 823043 A NO823043 A NO 823043A NO 823043 A NO823043 A NO 823043A NO 823043 L NO823043 L NO 823043L
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- group
- methyl
- approx
- hydrogen
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000000203 mixture Substances 0.000 claims description 71
- 239000000463 material Substances 0.000 claims description 51
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 150000002430 hydrocarbons Chemical class 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 229930195733 hydrocarbon Natural products 0.000 claims description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims description 16
- 150000001299 aldehydes Chemical class 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000002576 ketones Chemical class 0.000 claims description 14
- 239000003377 acid catalyst Substances 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 9
- PGTKVMVZBBZCKQ-UHFFFAOYSA-N Fulvene Chemical compound C=C1C=CC=C1 PGTKVMVZBBZCKQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 238000000465 moulding Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000011230 binding agent Substances 0.000 description 41
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 25
- 229920000642 polymer Polymers 0.000 description 25
- -1 methyl-substituted cyclopentadiene Chemical class 0.000 description 23
- 238000005266 casting Methods 0.000 description 22
- 239000004576 sand Substances 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000004593 Epoxy Substances 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 239000002245 particle Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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 8
- 238000005495 investment casting Methods 0.000 description 8
- 150000001728 carbonyl compounds Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 150000002234 fulvenes Chemical class 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000006061 abrasive grain Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 6
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000011256 inorganic filler Substances 0.000 description 5
- 229910003475 inorganic filler Inorganic materials 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 235000019256 formaldehyde Nutrition 0.000 description 4
- 239000011819 refractory material Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 229940106691 bisphenol a Drugs 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 229910010293 ceramic material Inorganic materials 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- VFNUNYPYULIJSN-UHFFFAOYSA-N 2,5-diisopropylphenol Chemical compound CC(C)C1=CC=C(C(C)C)C(O)=C1 VFNUNYPYULIJSN-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- JQCWLRHNAHIIGW-UHFFFAOYSA-N 2,8-dimethylnonan-5-one Chemical compound CC(C)CCC(=O)CCC(C)C JQCWLRHNAHIIGW-UHFFFAOYSA-N 0.000 description 2
- MOBNLCPBAMKACS-UHFFFAOYSA-N 2-(1-chloroethyl)oxirane Chemical compound CC(Cl)C1CO1 MOBNLCPBAMKACS-UHFFFAOYSA-N 0.000 description 2
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 2
- MMTOSBCMFDNOIY-UHFFFAOYSA-N 2-(chloromethyl)-3-methyloxirane Chemical compound CC1OC1CCl MMTOSBCMFDNOIY-UHFFFAOYSA-N 0.000 description 2
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 2
- SEAZSNZFNABEMJ-UHFFFAOYSA-N 3,4-diethylphenol Chemical compound CCC1=CC=C(O)C=C1CC SEAZSNZFNABEMJ-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- BILUCLFWRVWQQM-UHFFFAOYSA-N 3-(1-chloroethyl)-2,2-dimethyloxirane Chemical compound CC(Cl)C1OC1(C)C BILUCLFWRVWQQM-UHFFFAOYSA-N 0.000 description 2
- PNFOXSBXYSADIB-UHFFFAOYSA-N 3-chloro-4,5-dimethylphenol Chemical compound CC1=CC(O)=CC(Cl)=C1C PNFOXSBXYSADIB-UHFFFAOYSA-N 0.000 description 2
- URFNSYWAGGETFK-UHFFFAOYSA-N 4,4'-Dihydroxybibenzyl Chemical compound C1=CC(O)=CC=C1CCC1=CC=C(O)C=C1 URFNSYWAGGETFK-UHFFFAOYSA-N 0.000 description 2
- VYGLBTZLOQTMBG-UHFFFAOYSA-N 4-chloro-5-methylbenzene-1,3-diol Chemical compound CC1=CC(O)=CC(O)=C1Cl VYGLBTZLOQTMBG-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- VGMJYYDKPUPTID-UHFFFAOYSA-N 4-ethylbenzene-1,3-diol Chemical compound CCC1=CC=C(O)C=C1O VGMJYYDKPUPTID-UHFFFAOYSA-N 0.000 description 2
- FNYDIAAMUCQQDE-UHFFFAOYSA-N 4-methylbenzene-1,3-diol Chemical compound CC1=CC=C(O)C=C1O FNYDIAAMUCQQDE-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 239000003082 abrasive agent Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HCQHIEGYGGJLJU-UHFFFAOYSA-N didecyl hexanedioate Chemical compound CCCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCCCC HCQHIEGYGGJLJU-UHFFFAOYSA-N 0.000 description 2
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000010450 olivine Substances 0.000 description 2
- 229910052609 olivine Inorganic materials 0.000 description 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229910052845 zircon Inorganic materials 0.000 description 2
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 2
- XEABJLSKPBVCTB-UHFFFAOYSA-N (2-methyl-5-methylidenecyclopenta-1,3-dien-1-yl)benzene Chemical compound C=C1C=CC(C)=C1C1=CC=CC=C1 XEABJLSKPBVCTB-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- WXTONSHCBFAKNZ-UHFFFAOYSA-N (5-methylidenecyclopenta-1,3-dien-1-yl)cyclohexane Chemical compound C=C1C=CC=C1C1CCCCC1 WXTONSHCBFAKNZ-UHFFFAOYSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 1
- VMLNKPCIONBENX-UHFFFAOYSA-N 2,3-dichloro-5-methylphenol Chemical compound CC1=CC(O)=C(Cl)C(Cl)=C1 VMLNKPCIONBENX-UHFFFAOYSA-N 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- WVHICYNLISHYOB-UHFFFAOYSA-N 2,5-dichloro-3-methylphenol Chemical compound CC1=CC(Cl)=CC(O)=C1Cl WVHICYNLISHYOB-UHFFFAOYSA-N 0.000 description 1
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 description 1
- AQFCDVGUEQOTAC-UHFFFAOYSA-N 2,5-diethylphenol Chemical compound CCC1=CC=C(CC)C(O)=C1 AQFCDVGUEQOTAC-UHFFFAOYSA-N 0.000 description 1
- VXHYVVAUHMGCEX-UHFFFAOYSA-N 2-(2-hydroxyphenoxy)phenol Chemical class OC1=CC=CC=C1OC1=CC=CC=C1O VXHYVVAUHMGCEX-UHFFFAOYSA-N 0.000 description 1
- QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical class OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 description 1
- CWUMAFCRRBXNMN-UHFFFAOYSA-N 2-(bromomethyl)-3-butan-2-yloxirane Chemical compound CCC(C)C1OC1CBr CWUMAFCRRBXNMN-UHFFFAOYSA-N 0.000 description 1
- JOBYTHHZLJPOLW-UHFFFAOYSA-N 2-(chloromethyl)-2-ethyloxirane Chemical compound CCC1(CCl)CO1 JOBYTHHZLJPOLW-UHFFFAOYSA-N 0.000 description 1
- JPDKUVPXPYCAOC-UHFFFAOYSA-N 2-(chloromethyl)-2-methyl-3-pentyloxirane Chemical compound CCCCCC1OC1(C)CCl JPDKUVPXPYCAOC-UHFFFAOYSA-N 0.000 description 1
- OHAIVJAXSTXMFQ-UHFFFAOYSA-N 2-(chloromethyl)-3-pentyloxirane Chemical compound CCCCCC1OC1CCl OHAIVJAXSTXMFQ-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- APWRLAZEMYLHKZ-UHFFFAOYSA-N 2-amino-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound CC=1NC(N)=NC(=O)C=1C APWRLAZEMYLHKZ-UHFFFAOYSA-N 0.000 description 1
- AVNFUVHTTAGFJM-UHFFFAOYSA-N 2-bromo-4-(3-bromo-4-hydroxyphenoxy)phenol Chemical compound C1=C(Br)C(O)=CC=C1OC1=CC=C(O)C(Br)=C1 AVNFUVHTTAGFJM-UHFFFAOYSA-N 0.000 description 1
- WMCFQEMLVVLZIJ-UHFFFAOYSA-N 2-butyl-2-methylbutanedioic acid Chemical compound CCCCC(C)(C(O)=O)CC(O)=O WMCFQEMLVVLZIJ-UHFFFAOYSA-N 0.000 description 1
- GAEDVPMRQVZKEJ-UHFFFAOYSA-N 2-butyl-2-methylpentanedioic acid Chemical compound CCCCC(C)(C(O)=O)CCC(O)=O GAEDVPMRQVZKEJ-UHFFFAOYSA-N 0.000 description 1
- VMCOFBQXPQAQTE-UHFFFAOYSA-N 2-chloro-2-ethyl-3-methyloxirane Chemical compound CCC1(Cl)OC1C VMCOFBQXPQAQTE-UHFFFAOYSA-N 0.000 description 1
- ZXPLGLMEXWSLCX-UHFFFAOYSA-N 2-chloro-3,5-dimethylphenol Chemical compound CC1=CC(C)=C(Cl)C(O)=C1 ZXPLGLMEXWSLCX-UHFFFAOYSA-N 0.000 description 1
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- YPLYFEUBZLLLIY-UHFFFAOYSA-N dipropan-2-yl butanedioate Chemical compound CC(C)OC(=O)CCC(=O)OC(C)C YPLYFEUBZLLLIY-UHFFFAOYSA-N 0.000 description 1
- MSQKMFXJFBXZNQ-UHFFFAOYSA-N dipropan-2-yl pentanedioate Chemical compound CC(C)OC(=O)CCCC(=O)OC(C)C MSQKMFXJFBXZNQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910001651 emery Inorganic materials 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000010436 fluorite Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000002223 garnet Substances 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- 229910021343 molybdenum disilicide Inorganic materials 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004002 naphthaldehydes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 150000002883 o-cresols Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 150000002931 p-cresols Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22C—FOUNDRY MOULDING
- B22C1/00—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds
- B22C1/16—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents
- B22C1/20—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents
- B22C1/22—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents of resins or rosins
- B22C1/2233—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents of resins or rosins obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22C—FOUNDRY MOULDING
- B22C1/00—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds
- B22C1/16—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents
- B22C1/20—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents
- B22C1/22—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents of resins or rosins
- B22C1/2233—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents of resins or rosins obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- B22C1/2246—Condensation polymers of aldehydes and ketones
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B26/00—Compositions of mortars, concrete or artificial stone, containing only organic binders, e.g. polymer or resin concrete
- C04B26/02—Macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/08—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring
- C07C13/15—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring with a cyclopentadiene ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/862—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms
- C07C2/867—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only oxygen as hetero-atoms the non-hydrocarbon is an aldehyde or a ketone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Ceramic Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Mechanical Engineering (AREA)
- Structural Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Mold Materials And Core Materials (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/300,786 US4412088A (en) | 1981-09-10 | 1981-09-10 | Cyclopentadiene derivatives, method for preparing, and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO823043L true NO823043L (no) | 1983-03-11 |
Family
ID=23160576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO823043A NO823043L (no) | 1981-09-10 | 1982-09-08 | Cyclopentadienderivater og fremstilling og anvendelse derav |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4412088A (es) |
| JP (1) | JPS5859929A (es) |
| KR (1) | KR870000217B1 (es) |
| AU (1) | AU541200B2 (es) |
| BE (1) | BE894368A (es) |
| BR (1) | BR8205201A (es) |
| CA (1) | CA1185984A (es) |
| DE (1) | DE3233659A1 (es) |
| DK (1) | DK401882A (es) |
| ES (1) | ES515576A0 (es) |
| FR (1) | FR2512442B1 (es) |
| GB (1) | GB2108999B (es) |
| IE (1) | IE53782B1 (es) |
| IT (1) | IT1153189B (es) |
| NL (1) | NL8203494A (es) |
| NO (1) | NO823043L (es) |
| PT (1) | PT75534B (es) |
| SE (1) | SE8205111L (es) |
| ZA (1) | ZA826233B (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4636537A (en) * | 1984-01-30 | 1987-01-13 | Ashland Oil, Inc. | Composition, method for preparing and use thereof |
| US4721823A (en) * | 1986-09-19 | 1988-01-26 | Pennzoil Products Company | Lubricants comprising novel cyclopentanes, cyclopentadienes, cyclopentenes, and mixtures thereof and methods of manufacture |
| US4849566A (en) * | 1987-10-22 | 1989-07-18 | Pennzoil Products Company | Lubricants comprising novel cyclopentanes, cyclopentadienes, cyclopentenes, and mixtures thereof and methods of manufacture |
| US4929782A (en) * | 1986-09-19 | 1990-05-29 | Pennzoil Products Company | Lubricants comprising novel cyclopentanes, cyclopentadienes, cyclopentenes, and mixtures thereof and methods of manufacture |
| DE3635702A1 (de) * | 1986-10-21 | 1988-05-05 | Man Nutzfahrzeuge Gmbh | Drehschwingungsdaempfer mit angekoppelter keilriemenscheibeneinheit |
| DE3826088C1 (es) * | 1988-08-01 | 1989-07-06 | Fa. Carl Freudenberg, 6940 Weinheim, De | |
| FR2723102B1 (fr) * | 1994-07-26 | 1996-09-27 | Elf Antar France | Compositions de carburant contenant au moins un derive du fulvene, et leur utilisation |
| US5723708A (en) * | 1994-09-29 | 1998-03-03 | Nippon Petrochemicals Company, Limited | Method for producing cyclopentadienes |
| US5631203A (en) * | 1995-05-04 | 1997-05-20 | Phillips Petroleum Company | Metallocene compounds and preparation thereof containing terminal alkynes |
| CA2712088A1 (en) | 2008-01-31 | 2009-08-06 | Ashland Licensing And Intellectual Property Llc | Compositions containing certain metallocenes and their uses |
| DE102018000529A1 (de) * | 2018-01-23 | 2019-07-25 | Ask Chemicals Gmbh | Zusammensetzung, Fugenmasse und Verfahren zur Herstellung einer Fuge |
| WO2024102490A1 (en) * | 2022-11-11 | 2024-05-16 | ASK Chemicals LLC | Esters of epoxidized fatty acids in furfuryl alcohol binders |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2589969A (en) * | 1950-01-07 | 1952-03-18 | Standard Oil Dev Co | Production of fulvene hydrocarbons |
| US3051765A (en) * | 1959-03-30 | 1962-08-28 | Diamond Alkali Co | Chemical process for preparing fulvene compunds |
| DE1146050B (de) * | 1961-09-01 | 1963-03-28 | Consortium Elektrochem Ind | Verfahren zur Herstellung von Fulvenen |
| US3376304A (en) * | 1962-03-14 | 1968-04-02 | Mcneilab Inc | 2-(r-r1-r2-methyl)-6-r3-6-r4-fulvenes |
| US3218365A (en) * | 1962-09-10 | 1965-11-16 | Union Carbide Corp | Alkylation of fulvene compounds |
| US3262990A (en) * | 1963-10-11 | 1966-07-26 | Rohm & Haas | Fulvene-containing unsaturated polyester resins |
| US3390156A (en) * | 1963-10-11 | 1968-06-25 | Rohm & Haas | Fulvene compositions and polymers |
| US4246167A (en) * | 1979-05-25 | 1981-01-20 | Ashland Oil, Inc. | Foundry binder composition |
| US4320218A (en) * | 1980-08-04 | 1982-03-16 | Ashland Oil, Inc. | Binder composition |
-
1981
- 1981-09-10 US US06/300,786 patent/US4412088A/en not_active Expired - Fee Related
-
1982
- 1982-08-18 AU AU87294/82A patent/AU541200B2/en not_active Ceased
- 1982-08-19 CA CA000409780A patent/CA1185984A/en not_active Expired
- 1982-08-25 GB GB08224355A patent/GB2108999B/en not_active Expired
- 1982-08-26 ZA ZA826233A patent/ZA826233B/xx unknown
- 1982-09-03 BR BR8205201A patent/BR8205201A/pt unknown
- 1982-09-08 NO NO823043A patent/NO823043L/no unknown
- 1982-09-08 ES ES515576A patent/ES515576A0/es active Granted
- 1982-09-08 NL NL8203494A patent/NL8203494A/nl not_active Application Discontinuation
- 1982-09-08 DK DK401882A patent/DK401882A/da not_active Application Discontinuation
- 1982-09-08 SE SE8205111A patent/SE8205111L/xx not_active Application Discontinuation
- 1982-09-09 KR KR8204076A patent/KR870000217B1/ko active
- 1982-09-09 JP JP57156028A patent/JPS5859929A/ja active Granted
- 1982-09-09 PT PT75534A patent/PT75534B/pt unknown
- 1982-09-09 IE IE2211/82A patent/IE53782B1/en unknown
- 1982-09-10 FR FR8215380A patent/FR2512442B1/fr not_active Expired
- 1982-09-10 DE DE19823233659 patent/DE3233659A1/de not_active Withdrawn
- 1982-09-10 IT IT23209/82A patent/IT1153189B/it active
- 1982-09-10 BE BE0/208989A patent/BE894368A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS616047B2 (es) | 1986-02-24 |
| FR2512442B1 (fr) | 1986-04-18 |
| PT75534A (en) | 1982-10-01 |
| US4412088A (en) | 1983-10-25 |
| AU8729482A (en) | 1983-03-17 |
| JPS5859929A (ja) | 1983-04-09 |
| DE3233659A1 (de) | 1983-03-17 |
| AU541200B2 (en) | 1984-12-20 |
| IT1153189B (it) | 1987-01-14 |
| CA1185984A (en) | 1985-04-23 |
| IT8223209A0 (it) | 1982-09-10 |
| SE8205111L (sv) | 1983-03-11 |
| GB2108999B (en) | 1986-05-29 |
| SE8205111D0 (sv) | 1982-09-08 |
| ES8308528A1 (es) | 1983-09-16 |
| BE894368A (fr) | 1983-01-03 |
| GB2108999A (en) | 1983-05-25 |
| ZA826233B (en) | 1983-07-27 |
| PT75534B (en) | 1984-12-12 |
| DK401882A (da) | 1983-03-11 |
| ES515576A0 (es) | 1983-09-16 |
| FR2512442A1 (fr) | 1983-03-11 |
| BR8205201A (pt) | 1983-08-16 |
| IE53782B1 (en) | 1989-02-15 |
| NL8203494A (nl) | 1983-04-05 |
| KR870000217B1 (ko) | 1987-02-17 |
| IE822211L (en) | 1983-03-10 |
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