DE2444681A1 - Verfahren zur polymerisation von norbornen-derivaten - Google Patents
Verfahren zur polymerisation von norbornen-derivatenInfo
- Publication number
- DE2444681A1 DE2444681A1 DE19742444681 DE2444681A DE2444681A1 DE 2444681 A1 DE2444681 A1 DE 2444681A1 DE 19742444681 DE19742444681 DE 19742444681 DE 2444681 A DE2444681 A DE 2444681A DE 2444681 A1 DE2444681 A1 DE 2444681A1
- Authority
- DE
- Germany
- Prior art keywords
- norbornene
- methyl
- component
- carboxylate
- saturated
- Prior art date
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 84
- 238000006116 polymerization reaction Methods 0.000 title description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 201
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 111
- 150000001875 compounds Chemical class 0.000 claims description 54
- 239000003054 catalyst Substances 0.000 claims description 51
- 150000002430 hydrocarbons Chemical group 0.000 claims description 37
- 150000002848 norbornenes Chemical class 0.000 claims description 32
- 229920000642 polymer Polymers 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 24
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 22
- -1 compounds Ester Chemical class 0.000 claims description 19
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 15
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 11
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 11
- 229910052750 molybdenum Inorganic materials 0.000 claims description 11
- 229910052721 tungsten Inorganic materials 0.000 claims description 11
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 229920001577 copolymer Polymers 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 150000002902 organometallic compounds Chemical class 0.000 claims description 8
- 229910052715 tantalum Inorganic materials 0.000 claims description 8
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- 125000002560 nitrile group Chemical group 0.000 claims description 7
- 230000000737 periodic effect Effects 0.000 claims description 7
- 229910052702 rhenium Inorganic materials 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 claims description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001925 cycloalkenes Chemical class 0.000 claims description 6
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- RMAZRAQKPTXZNL-UHFFFAOYSA-N methyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC)CC1C=C2 RMAZRAQKPTXZNL-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims description 4
- 229940117916 cinnamic aldehyde Drugs 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000005462 imide group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 150000007519 polyprotic acids Polymers 0.000 claims description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- ZTUUVDYQBLRAAC-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxamide Chemical compound C1C2C(C(=O)N)CC1C=C2 ZTUUVDYQBLRAAC-UHFFFAOYSA-N 0.000 claims description 3
- 150000003949 imides Chemical class 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 2
- LTVUCOSIZFEASK-UHFFFAOYSA-N 1,2,3,6-tetrahydro methyl-3,6-methanophthalic anhydride Chemical compound C1=CC2CC1C1C2(C)C(=O)OC1=O LTVUCOSIZFEASK-UHFFFAOYSA-N 0.000 claims description 2
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 claims description 2
- 239000004912 1,5-cyclooctadiene Substances 0.000 claims description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- KOFGXLTWJXWTBK-UHFFFAOYSA-N 2,3-dimethylbicyclo[2.2.1]hept-5-ene-3-carbonitrile Chemical compound C1C2C=CC1C(C)C2(C)C#N KOFGXLTWJXWTBK-UHFFFAOYSA-N 0.000 claims description 2
- JLUADGGGXPOCHP-UHFFFAOYSA-N 2,6-dichloro-4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione Chemical compound C1=CC2CC1C1(Cl)C2(Cl)C(=O)OC1=O JLUADGGGXPOCHP-UHFFFAOYSA-N 0.000 claims description 2
- WCEWVZCIRJJXCJ-UHFFFAOYSA-N 2-butyl-4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione Chemical compound C1=CC2CC1C1C2(CCCC)C(=O)OC1=O WCEWVZCIRJJXCJ-UHFFFAOYSA-N 0.000 claims description 2
- ZIHMRTXPWOQFDR-UHFFFAOYSA-N 2-butylbicyclo[2.2.1]hept-5-ene-3-carbonitrile Chemical compound C1C2C=CC1C(CCCC)C2C#N ZIHMRTXPWOQFDR-UHFFFAOYSA-N 0.000 claims description 2
- YXAWSVIBBDBUJW-UHFFFAOYSA-N 2-ethyl-4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione Chemical compound C1=CC2CC1C1C2(CC)C(=O)OC1=O YXAWSVIBBDBUJW-UHFFFAOYSA-N 0.000 claims description 2
- XMEHABOIHLPLLN-UHFFFAOYSA-N 2-ethyl-6-methyl-4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione Chemical class C1=CC2CC1C1(C)C2(CC)C(=O)OC1=O XMEHABOIHLPLLN-UHFFFAOYSA-N 0.000 claims description 2
- VXIKRQMVHSKPRB-UHFFFAOYSA-N 2-ethylbicyclo[2.2.1]hept-5-ene-3-carbonitrile Chemical compound C1C2C=CC1C(CC)C2C#N VXIKRQMVHSKPRB-UHFFFAOYSA-N 0.000 claims description 2
- RSCIDCVEEKEQCR-UHFFFAOYSA-N 2-methylbicyclo[2.2.1]hept-5-ene-3-carbonitrile Chemical compound C1C2C=CC1C(C)C2C#N RSCIDCVEEKEQCR-UHFFFAOYSA-N 0.000 claims description 2
- XYJSKMUSEUJBDV-UHFFFAOYSA-N 3,3-dimethylbicyclo[2.2.1]hept-5-ene-2-carbonitrile Chemical compound C1C2C=CC1C(C)(C)C2C#N XYJSKMUSEUJBDV-UHFFFAOYSA-N 0.000 claims description 2
- IMMQTZLIZANXTR-UHFFFAOYSA-N 3-chloro-2-methylbicyclo[2.2.1]hept-5-ene Chemical compound C1C2C=CC1C(C)C2Cl IMMQTZLIZANXTR-UHFFFAOYSA-N 0.000 claims description 2
- YZXUSJBXFGZZKI-UHFFFAOYSA-N 3-methylbicyclo[2.2.1]hept-5-ene-2,3-dicarbonitrile Chemical compound C1C2C=CC1C(C)(C#N)C2C#N YZXUSJBXFGZZKI-UHFFFAOYSA-N 0.000 claims description 2
- OSAZDTCUOMNDAZ-UHFFFAOYSA-N 3-phenylbicyclo[2.2.1]hept-5-ene-2-carbonitrile Chemical compound N#CC1C(C=C2)CC2C1C1=CC=CC=C1 OSAZDTCUOMNDAZ-UHFFFAOYSA-N 0.000 claims description 2
- PMLRFHVVTBAUJJ-UHFFFAOYSA-N 3a-chloro-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C1=CC2CC1C1C2(Cl)C(=O)OC1=O PMLRFHVVTBAUJJ-UHFFFAOYSA-N 0.000 claims description 2
- DRWRVXAXXGJZIO-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enyl acetate Chemical compound C1C2C(OC(=O)C)CC1C=C2 DRWRVXAXXGJZIO-UHFFFAOYSA-N 0.000 claims description 2
- VDSOFEUECITLJU-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enyl propanoate Chemical compound C1C2C(OC(=O)CC)CC1C=C2 VDSOFEUECITLJU-UHFFFAOYSA-N 0.000 claims description 2
- DWPPXNJBRSZQHD-UHFFFAOYSA-N 5-bromobicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(Br)CC1C=C2 DWPPXNJBRSZQHD-UHFFFAOYSA-N 0.000 claims description 2
- PSCJIEZOAFAQRM-UHFFFAOYSA-N 5-chlorobicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(Cl)CC1C=C2 PSCJIEZOAFAQRM-UHFFFAOYSA-N 0.000 claims description 2
- PCBPVYHMZBWMAZ-UHFFFAOYSA-N 5-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C)CC1C=C2 PCBPVYHMZBWMAZ-UHFFFAOYSA-N 0.000 claims description 2
- YLSRLICOTNISRM-UHFFFAOYSA-N 5-methylbicyclo[2.2.1]hept-2-ene-5-carbonitrile Chemical compound C1C2C(C)(C#N)CC1C=C2 YLSRLICOTNISRM-UHFFFAOYSA-N 0.000 claims description 2
- PGNNHYNYFLXKDZ-UHFFFAOYSA-N 5-phenylbicyclo[2.2.1]hept-2-ene Chemical compound C1=CC2CC1CC2C1=CC=CC=C1 PGNNHYNYFLXKDZ-UHFFFAOYSA-N 0.000 claims description 2
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 claims description 2
- 229910004860 CaZn Inorganic materials 0.000 claims description 2
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 2
- WXAMJXJYUHAUQT-UHFFFAOYSA-N ac1mffmi Chemical compound O=C1C2C(C=C3)CC3C2C(=O)N1C1CCCCC1 WXAMJXJYUHAUQT-UHFFFAOYSA-N 0.000 claims description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 2
- 125000005595 acetylacetonate group Chemical group 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 2
- DJNPQHBMESQZIP-UHFFFAOYSA-N bicyclo[2.2.1]hept-5-ene-2,3-dicarbonitrile Chemical compound C1C2C=CC1C(C#N)C2C#N DJNPQHBMESQZIP-UHFFFAOYSA-N 0.000 claims description 2
- RFIHUFUZAHTZOQ-UHFFFAOYSA-N butyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OCCCC)CC1C=C2 RFIHUFUZAHTZOQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000003997 cyclic ketones Chemical class 0.000 claims description 2
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 claims description 2
- MSPIWBYBMMBCEX-UHFFFAOYSA-N cyclohexyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C(C=C2)CC2C1C(=O)OC1CCCCC1 MSPIWBYBMMBCEX-UHFFFAOYSA-N 0.000 claims description 2
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims description 2
- 239000004913 cyclooctene Substances 0.000 claims description 2
- HANKSFAYJLDDKP-UHFFFAOYSA-N dihydrodicyclopentadiene Chemical compound C12CC=CC2C2CCC1C2 HANKSFAYJLDDKP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005594 diketone group Chemical group 0.000 claims description 2
- FCCGTJAGEHZPBF-UHFFFAOYSA-N ethyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OCC)CC1C=C2 FCCGTJAGEHZPBF-UHFFFAOYSA-N 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 229910052734 helium Inorganic materials 0.000 claims description 2
- 239000001307 helium Substances 0.000 claims description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- MHQRPGFVLWGVIW-UHFFFAOYSA-N methyl 3,5-dioxo-4-oxatricyclo[5.2.1.02,6]dec-8-ene-2-carboxylate Chemical compound COC(=O)C12C3C=CC(C1C(=O)OC2=O)C3 MHQRPGFVLWGVIW-UHFFFAOYSA-N 0.000 claims description 2
- 229940017219 methyl propionate Drugs 0.000 claims description 2
- KKDPDOZDMGZHRA-UHFFFAOYSA-N n,n-diethyl-2-phenylbicyclo[2.2.1]hept-5-ene-3-carboxamide Chemical compound CCN(CC)C(=O)C1C(C=C2)CC2C1C1=CC=CC=C1 KKDPDOZDMGZHRA-UHFFFAOYSA-N 0.000 claims description 2
- VJKBQUJCCYLNCM-UHFFFAOYSA-N n-octyl-5-norbornene-2,3-dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(C(CC)CCCC)C1=O VJKBQUJCCYLNCM-UHFFFAOYSA-N 0.000 claims description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 claims description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 2
- CIURXHXRVCRQLM-UHFFFAOYSA-N octyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OCCCCCCCC)CC1C=C2 CIURXHXRVCRQLM-UHFFFAOYSA-N 0.000 claims description 2
- WLVPQQDEYVVXJF-UHFFFAOYSA-N phenyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C(C=C2)CC2C1C(=O)OC1=CC=CC=C1 WLVPQQDEYVVXJF-UHFFFAOYSA-N 0.000 claims description 2
- 102200127556 rs34159654 Human genes 0.000 claims description 2
- GAONUEUNHBLHPP-UHFFFAOYSA-N stk246934 Chemical compound O=C1C2C(C=C3)CC3C2C(=O)N1C1=CC=CC=C1 GAONUEUNHBLHPP-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- XRXMMKODPHLSBS-UHFFFAOYSA-N undec-9-en-3-one Chemical compound CCC(=O)CCCCCC=CC XRXMMKODPHLSBS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims 2
- SXIFNAOBIAIYJO-SXVCMZJPSA-N (1E,3E,7E)-cyclododeca-1,3,7-triene Chemical compound C/1=C\CCCC\C=C\C=C\CC\1 SXIFNAOBIAIYJO-SXVCMZJPSA-N 0.000 claims 1
- DHWUSGGROYUWEV-UHFFFAOYSA-N 2-(5-methyl-5-bicyclo[2.2.1]hept-2-enyl)acetic acid Chemical compound C1C2C(C)(CC(O)=O)CC1C=C2 DHWUSGGROYUWEV-UHFFFAOYSA-N 0.000 claims 1
- ZTVHHSZPQYVCHZ-UHFFFAOYSA-N 2-octyl-4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione Chemical compound C1=CC2CC1C1C2(CCCCCCCC)C(=O)OC1=O ZTVHHSZPQYVCHZ-UHFFFAOYSA-N 0.000 claims 1
- 150000007960 acetonitrile Chemical class 0.000 claims 1
- NIDNOXCRFUCAKQ-UHFFFAOYSA-N bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(=O)O)C2C(O)=O NIDNOXCRFUCAKQ-UHFFFAOYSA-N 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- VGQLNJWOULYVFV-WZENYGAOSA-N dimethyl (2r,3s)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate Chemical compound C1C2C=CC1[C@H](C(=O)OC)[C@@H]2C(=O)OC VGQLNJWOULYVFV-WZENYGAOSA-N 0.000 claims 1
- ZZPJBUXGZVVGOC-UHFFFAOYSA-N dodecyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OCCCCCCCCCCCC)CC1C=C2 ZZPJBUXGZVVGOC-UHFFFAOYSA-N 0.000 claims 1
- QZXTYHYAZQOPIP-UHFFFAOYSA-N n,n,5-trimethylbicyclo[2.2.1]hept-2-ene-5-carboxamide Chemical compound C1C2C(C(=O)N(C)C)(C)CC1C=C2 QZXTYHYAZQOPIP-UHFFFAOYSA-N 0.000 claims 1
- QDIURVLTYFGLCN-UHFFFAOYSA-N n-methylbicyclo[2.2.1]hept-2-ene-5-carboxamide Chemical compound C1C2C(C(=O)NC)CC1C=C2 QDIURVLTYFGLCN-UHFFFAOYSA-N 0.000 claims 1
- XGBHRXNRYYODNV-UHFFFAOYSA-N n-phenylbicyclo[2.2.1]hept-2-ene-5-carboxamide Chemical compound C1C(C=C2)CC2C1C(=O)NC1=CC=CC=C1 XGBHRXNRYYODNV-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 125000003944 tolyl group Chemical group 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 8
- 239000003708 ampul Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BMAXQTDMWYDIJX-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carbonitrile Chemical compound C1C2C(C#N)CC1C=C2 BMAXQTDMWYDIJX-UHFFFAOYSA-N 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical group CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- BWHOZHOGCMHOBV-UHFFFAOYSA-N Benzalacetone Natural products CC(=O)C=CC1=CC=CC=C1 BWHOZHOGCMHOBV-UHFFFAOYSA-N 0.000 description 2
- HYTRYEXINDDXJK-UHFFFAOYSA-N Ethyl isopropyl ketone Chemical compound CCC(=O)C(C)C HYTRYEXINDDXJK-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 229940054441 o-phthalaldehyde Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical group O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 2
- QZBQBYPSEPDGSA-UHFFFAOYSA-N 1,7,8,9,10,10-hexachloro-4-oxatricyclo[5.2.1.02,6]dec-2(6)-ene-3,5-dione Chemical compound O=C1OC(=O)C2=C1C1(Cl)C(Cl)C(Cl)C2(Cl)C1(Cl)Cl QZBQBYPSEPDGSA-UHFFFAOYSA-N 0.000 description 1
- WHRYLXXHLFPFNZ-UHFFFAOYSA-N 2-methyl-3a,4,7,7a-tetrahydro-1h-4,7-methanoisoindole-1,3(2h)-dione Chemical compound C1=CC2CC1C1C2C(=O)N(C)C1=O WHRYLXXHLFPFNZ-UHFFFAOYSA-N 0.000 description 1
- KUKRLSJNTMLPPK-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]hept-2-ene Chemical class C1CC2(C)C=CC1C2(C)C KUKRLSJNTMLPPK-UHFFFAOYSA-N 0.000 description 1
- FDOCSCGYUBLVFK-UHFFFAOYSA-N 5-chloro-5-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C)(Cl)CC1C=C2 FDOCSCGYUBLVFK-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 description 1
- DVDVFJQUNHPDBG-UHFFFAOYSA-N bicyclo[2.2.1]hept-5-ene-2,3-dicarboxamide Chemical compound C1C2C=CC1C(C(=O)N)C2C(N)=O DVDVFJQUNHPDBG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- ATQXMSAPMLWHBZ-UHFFFAOYSA-N chlorobenzene;propan-2-one Chemical compound CC(C)=O.ClC1=CC=CC=C1 ATQXMSAPMLWHBZ-UHFFFAOYSA-N 0.000 description 1
- HDNAENGLYCLHFK-UHFFFAOYSA-N cis-endo-n-ethyl-5-norbornene-2,3-dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(CC)C1=O HDNAENGLYCLHFK-UHFFFAOYSA-N 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 description 1
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 1
- FWOHIDPWUOBLTI-UHFFFAOYSA-N diphenylmethanone;toluene Chemical compound CC1=CC=CC=C1.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 FWOHIDPWUOBLTI-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- CVCQFCVMUMOBBJ-UHFFFAOYSA-N ethyl 2-methylbicyclo[2.2.1]hept-5-ene-3-carboxylate Chemical compound C1C2C(C(=O)OCC)C(C)C1C=C2 CVCQFCVMUMOBBJ-UHFFFAOYSA-N 0.000 description 1
- NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
- JYGYEBCBALMPDC-UHFFFAOYSA-N heptane;propan-2-one Chemical compound CC(C)=O.CCCCCCC JYGYEBCBALMPDC-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- QJXVSJAVMTXAMO-UHFFFAOYSA-N methyl 2-(3,5-dioxo-4-oxatricyclo[5.2.1.02,6]dec-8-en-2-yl)acetate Chemical compound C1=CC2CC1C1C2(CC(=O)OC)C(=O)OC1=O QJXVSJAVMTXAMO-UHFFFAOYSA-N 0.000 description 1
- AEBDJCUTXUYLDC-UHFFFAOYSA-N methyl 5-methylbicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC)(C)CC1C=C2 AEBDJCUTXUYLDC-UHFFFAOYSA-N 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- VHDXYZOZULHRIL-UHFFFAOYSA-N n,n-dimethylbicyclo[2.2.1]hept-2-ene-5-carboxamide Chemical compound C1C2C(C(=O)N(C)C)CC1C=C2 VHDXYZOZULHRIL-UHFFFAOYSA-N 0.000 description 1
- 150000004831 organic oxygen compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- 150000002927 oxygen compounds Chemical class 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N phenyl propionaldehyde Natural products CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003246 polypentenamer Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1115075A CH600187A5 (en) | 1974-09-18 | 1975-08-28 | Friction ring for installation of hub on shaft |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10568073A JPS5058198A (enrdf_load_stackoverflow) | 1973-09-19 | 1973-09-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2444681A1 true DE2444681A1 (de) | 1975-03-27 |
Family
ID=14414125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742444681 Withdrawn DE2444681A1 (de) | 1973-09-19 | 1974-09-18 | Verfahren zur polymerisation von norbornen-derivaten |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5058198A (enrdf_load_stackoverflow) |
| DE (1) | DE2444681A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1456597A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002280A1 (en) * | 1977-12-05 | 1979-06-13 | The B.F. GOODRICH Company | Ring-opened copolymers of dihydrodicyclopentadiene and the like |
| EP0181640A1 (en) * | 1984-11-16 | 1986-05-21 | Hercules Incorporated | Copolymers of dicyclopentadiene |
| EP0317262A3 (en) * | 1987-11-17 | 1990-08-29 | Japan Synthetic Rubber Co., Ltd. | Transparent resin material |
| EP1342745A1 (de) * | 2002-03-05 | 2003-09-10 | Lofo High Tech Film GmbH | Verfahren zur Herstellung von Polyolefinfolien |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4941496A (enrdf_load_stackoverflow) * | 1972-05-19 | 1974-04-18 | ||
| JPS4977999A (enrdf_load_stackoverflow) * | 1972-12-01 | 1974-07-26 |
-
1973
- 1973-09-19 JP JP10568073A patent/JPS5058198A/ja active Pending
-
1974
- 1974-09-18 GB GB4065874A patent/GB1456597A/en not_active Expired
- 1974-09-18 DE DE19742444681 patent/DE2444681A1/de not_active Withdrawn
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0002280A1 (en) * | 1977-12-05 | 1979-06-13 | The B.F. GOODRICH Company | Ring-opened copolymers of dihydrodicyclopentadiene and the like |
| EP0181640A1 (en) * | 1984-11-16 | 1986-05-21 | Hercules Incorporated | Copolymers of dicyclopentadiene |
| EP0317262A3 (en) * | 1987-11-17 | 1990-08-29 | Japan Synthetic Rubber Co., Ltd. | Transparent resin material |
| US5053471A (en) * | 1987-11-17 | 1991-10-01 | Japan Synthetic Rubber Co., Ltd. | Transparent resin material |
| EP1342745A1 (de) * | 2002-03-05 | 2003-09-10 | Lofo High Tech Film GmbH | Verfahren zur Herstellung von Polyolefinfolien |
| WO2003074592A1 (de) * | 2002-03-05 | 2003-09-12 | Lofo High Tech Film Gmbh | Verfahren zur herstellung von polyolefinfolien |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1456597A (en) | 1976-11-24 |
| JPS5058198A (enrdf_load_stackoverflow) | 1975-05-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OF | Willingness to grant licences before publication of examined application | ||
| OD | Request for examination | ||
| 8139 | Disposal/non-payment of the annual fee |