ES2282493T3 - Policetona y procedimiento para su preparacion. - Google Patents
Policetona y procedimiento para su preparacion. Download PDFInfo
- Publication number
- ES2282493T3 ES2282493T3 ES02786195T ES02786195T ES2282493T3 ES 2282493 T3 ES2282493 T3 ES 2282493T3 ES 02786195 T ES02786195 T ES 02786195T ES 02786195 T ES02786195 T ES 02786195T ES 2282493 T3 ES2282493 T3 ES 2282493T3
- Authority
- ES
- Spain
- Prior art keywords
- polyketone
- group
- polymerization
- terminal
- terminal group
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 88
- 238000002360 preparation method Methods 0.000 title description 9
- 229920001470 polyketone Polymers 0.000 claims abstract description 336
- 239000000835 fiber Substances 0.000 claims abstract description 45
- -1 1-oxotrimethylene Chemical group 0.000 claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000000468 ketone group Chemical group 0.000 claims abstract description 5
- 125000004185 ester group Chemical group 0.000 claims abstract description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 211
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 156
- 239000002904 solvent Substances 0.000 claims description 105
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 75
- 238000006243 chemical reaction Methods 0.000 claims description 60
- 230000037048 polymerization activity Effects 0.000 claims description 59
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 45
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
- 239000003054 catalyst Substances 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 37
- 238000002844 melting Methods 0.000 claims description 33
- 230000008018 melting Effects 0.000 claims description 33
- 239000007788 liquid Substances 0.000 claims description 31
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 29
- 239000005977 Ethylene Substances 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- 230000014509 gene expression Effects 0.000 claims description 24
- 239000003446 ligand Substances 0.000 claims description 23
- 125000004429 atom Chemical group 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 229910052763 palladium Inorganic materials 0.000 claims description 18
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 claims description 17
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 17
- 150000002941 palladium compounds Chemical class 0.000 claims description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 14
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
- 125000005907 alkyl ester group Chemical group 0.000 claims description 12
- 150000004696 coordination complex Chemical class 0.000 claims description 11
- SXXPTCXIFIOPQF-UHFFFAOYSA-N 3-bis(2-methoxyphenyl)phosphanylpropyl-bis(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)CCCP(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC SXXPTCXIFIOPQF-UHFFFAOYSA-N 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 8
- 150000002430 hydrocarbons Chemical group 0.000 claims description 8
- 125000000962 organic group Chemical group 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 7
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 7
- 238000002835 absorbance Methods 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 229930192627 Naphthoquinone Natural products 0.000 claims description 5
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 150000002791 naphthoquinones Chemical class 0.000 claims description 5
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical group CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 5
- 238000002211 ultraviolet spectrum Methods 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- ZDJMEIUMFOTGDV-UHFFFAOYSA-N [2-[bis(2-methoxyphenyl)phosphanylmethyl]phenyl]methyl-bis(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)CC1=CC=CC=C1CP(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC ZDJMEIUMFOTGDV-UHFFFAOYSA-N 0.000 claims description 4
- 238000007334 copolymerization reaction Methods 0.000 claims description 4
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 claims description 4
- 238000013480 data collection Methods 0.000 claims description 3
- PBDBXAQKXCXZCJ-UHFFFAOYSA-L palladium(2+);2,2,2-trifluoroacetate Chemical compound [Pd+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F PBDBXAQKXCXZCJ-UHFFFAOYSA-L 0.000 claims description 3
- 239000010453 quartz Substances 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 239000003733 fiber-reinforced composite Substances 0.000 claims description 2
- KRBYXPHICJFVFQ-UHFFFAOYSA-N methanesulfonic acid trifluoromethanesulfonic acid Chemical compound FC(S(=O)(=O)O)(F)F.S(=O)(=O)(C(F)(F)F)O.CS(=O)(=O)O KRBYXPHICJFVFQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004492 methyl ester group Chemical group 0.000 claims description 2
- 230000000754 repressing effect Effects 0.000 claims 2
- 229920001971 elastomer Polymers 0.000 abstract description 4
- 229920005989 resin Polymers 0.000 abstract description 4
- 239000011347 resin Substances 0.000 abstract description 4
- 239000005060 rubber Substances 0.000 abstract description 4
- 239000004568 cement Substances 0.000 abstract description 2
- 239000012776 electronic material Substances 0.000 abstract description 2
- 239000012567 medical material Substances 0.000 abstract description 2
- 239000013307 optical fiber Substances 0.000 abstract description 2
- 239000005022 packaging material Substances 0.000 abstract description 2
- 239000012779 reinforcing material Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 59
- 238000000465 moulding Methods 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
- 230000000052 comparative effect Effects 0.000 description 31
- 238000011282 treatment Methods 0.000 description 25
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 238000010438 heat treatment Methods 0.000 description 20
- 239000007789 gas Substances 0.000 description 19
- 229920000642 polymer Polymers 0.000 description 19
- 238000005406 washing Methods 0.000 description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 18
- 230000006866 deterioration Effects 0.000 description 17
- 230000000694 effects Effects 0.000 description 17
- 238000001035 drying Methods 0.000 description 16
- 230000004048 modification Effects 0.000 description 16
- 238000012986 modification Methods 0.000 description 15
- 239000000843 powder Substances 0.000 description 14
- 238000000605 extraction Methods 0.000 description 13
- 239000002184 metal Substances 0.000 description 12
- 230000002035 prolonged effect Effects 0.000 description 12
- 239000011592 zinc chloride Substances 0.000 description 12
- 235000005074 zinc chloride Nutrition 0.000 description 12
- 230000007423 decrease Effects 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000009987 spinning Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000011701 zinc Substances 0.000 description 7
- 229940005561 1,4-benzoquinone Drugs 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000000701 coagulant Substances 0.000 description 6
- 229940117927 ethylene oxide Drugs 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 5
- 230000007774 longterm Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 150000004053 quinones Chemical class 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 4
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
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- 238000003860 storage Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000004804 winding Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 230000015271 coagulation Effects 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000004336 hydroxyquinones Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000004816 latex Substances 0.000 description 3
- 229920000126 latex Polymers 0.000 description 3
- 238000012423 maintenance Methods 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000005882 aldol condensation reaction Methods 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
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- 238000004821 distillation Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 238000009434 installation Methods 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
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 229910052696 pnictogen Inorganic materials 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- YLDJNDYRGPTCKV-UHFFFAOYSA-N (2-diphenylphosphanylcyclohexyl)-diphenylphosphane Chemical compound C1CCCC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YLDJNDYRGPTCKV-UHFFFAOYSA-N 0.000 description 1
- NFRYVRNCDXULEX-UHFFFAOYSA-N (2-diphenylphosphanylphenyl)-diphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C(=CC=CC=1)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 NFRYVRNCDXULEX-UHFFFAOYSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
- PPOQZCLACPIFHG-UHFFFAOYSA-N 1,3-bis[bis(2-methoxyphenyl)phosphanyl]propan-2-ol Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)CC(O)CP(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC PPOQZCLACPIFHG-UHFFFAOYSA-N 0.000 description 1
- DGPGVLIQUWUVIT-UHFFFAOYSA-N 1-methoxy-2-[1-(2-methoxyphenyl)ethyl]benzene Chemical compound COC1=CC=CC=C1C(C)C1=CC=CC=C1OC DGPGVLIQUWUVIT-UHFFFAOYSA-N 0.000 description 1
- GPLIMIJPIZGPIF-UHFFFAOYSA-N 2-hydroxy-1,4-benzoquinone Chemical compound OC1=CC(=O)C=CC1=O GPLIMIJPIZGPIF-UHFFFAOYSA-N 0.000 description 1
- WPTCSQBWLUUYDV-UHFFFAOYSA-N 2-quinolin-2-ylquinoline Chemical compound C1=CC=CC2=NC(C3=NC4=CC=CC=C4C=C3)=CC=C21 WPTCSQBWLUUYDV-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 1
- NBPGPQJFYXNFKN-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine Chemical group CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 NBPGPQJFYXNFKN-UHFFFAOYSA-N 0.000 description 1
- PCBPVYHMZBWMAZ-UHFFFAOYSA-N 5-methylbicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(C)CC1C=C2 PCBPVYHMZBWMAZ-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000006945 Knorr synthesis reaction Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- BZDNMSNFLZXRLY-UHFFFAOYSA-N [2-(diphenylphosphanylmethyl)phenyl]methyl-diphenylphosphane Chemical compound C=1C=CC=C(CP(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 BZDNMSNFLZXRLY-UHFFFAOYSA-N 0.000 description 1
- ZAADBUUITKVBKF-UHFFFAOYSA-N [3-bis(2-methoxyphenyl)phosphanyl-2,2-dimethylpropyl]-bis(2-methoxyphenyl)phosphane Chemical compound COC1=CC=CC=C1P(C=1C(=CC=CC=1)OC)CC(C)(C)CP(C=1C(=CC=CC=1)OC)C1=CC=CC=C1OC ZAADBUUITKVBKF-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000001253 acrylic acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003738 black carbon Substances 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012757 flame retardant agent Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000012685 gas phase polymerization Methods 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000006099 infrared radiation absorber Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- APRJFNLVTJWEPP-UHFFFAOYSA-M n,n-diethylcarbamate Chemical compound CCN(CC)C([O-])=O APRJFNLVTJWEPP-UHFFFAOYSA-M 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl 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])* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- UHGIMQLJWRAPLT-UHFFFAOYSA-N octadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(O)=O UHGIMQLJWRAPLT-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000006100 radiation absorber Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C9/00—Reinforcements or ply arrangement of pneumatic tyres
- B60C9/0042—Reinforcements made of synthetic materials
-
- 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
- C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
- C08G67/02—Copolymers of carbon monoxide and aliphatic unsaturated compounds
-
- 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
- C08G85/00—General processes for preparing compounds provided for in this subclass
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/28—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F6/30—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising olefins as the major constituent
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/76—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from other polycondensation products
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Mechanical Engineering (AREA)
- Polyethers (AREA)
- Artificial Filaments (AREA)
- Materials For Medical Uses (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Yarns And Mechanical Finishing Of Yarns Or Ropes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyesters Or Polycarbonates (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001393617 | 2001-12-26 | ||
| JP2001-393617 | 2001-12-26 | ||
| JP2002-69569 | 2002-03-14 | ||
| JP2002069569 | 2002-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2282493T3 true ES2282493T3 (es) | 2007-10-16 |
Family
ID=26625277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02786195T Expired - Lifetime ES2282493T3 (es) | 2001-12-26 | 2002-12-24 | Policetona y procedimiento para su preparacion. |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US20050075475A1 (https=) |
| EP (1) | EP1460097B1 (https=) |
| JP (1) | JP4601294B2 (https=) |
| KR (1) | KR100668572B1 (https=) |
| AT (1) | ATE361941T1 (https=) |
| AU (1) | AU2002354267A1 (https=) |
| DE (1) | DE60220096T2 (https=) |
| ES (1) | ES2282493T3 (https=) |
| TW (1) | TW200302236A (https=) |
| WO (1) | WO2003055934A1 (https=) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005133034A (ja) * | 2003-10-31 | 2005-05-26 | Fuji Xerox Co Ltd | 脂肪族ポリエーテルケトン類ポリマー、および樹脂組成物 |
| KR100652072B1 (ko) * | 2004-11-24 | 2006-12-01 | 주식회사 효성 | 폴리케톤의 제조방법 |
| KR100595562B1 (ko) * | 2004-11-24 | 2006-07-03 | 주식회사 효성 | 폴리케톤의 제조방법 |
| KR100652087B1 (ko) * | 2004-11-24 | 2006-12-01 | 주식회사 효성 | 폴리케톤의 제조방법 |
| KR100643673B1 (ko) * | 2004-11-30 | 2006-11-10 | 주식회사 효성 | 폴리케톤의 제조방법 |
| KR100652075B1 (ko) * | 2005-12-29 | 2006-12-01 | 주식회사 효성 | 촉매 전구체를 사용한 폴리케톤의 제조방법 |
| KR100652073B1 (ko) * | 2005-12-29 | 2006-12-01 | 주식회사 효성 | 폴리케톤의 제조방법 |
| US8215357B2 (en) * | 2006-07-19 | 2012-07-10 | Bridgestone Corporation | Pneumatic tire |
| KR100721448B1 (ko) * | 2006-08-31 | 2007-05-23 | 주식회사 효성 | 폴리케톤의 제조방법 |
| KR100721450B1 (ko) * | 2006-08-31 | 2007-05-23 | 주식회사 효성 | 폴리케톤의 제조방법 |
| KR101016276B1 (ko) * | 2006-09-11 | 2011-02-22 | 아사히 가세이 가부시키가이샤 | 고분자 전해질과 그 제조방법, 및 전기 화학 소자 |
| KR100816680B1 (ko) * | 2006-12-28 | 2008-03-27 | 주식회사 효성 | 폴리케톤의 제조방법 |
| KR100789141B1 (ko) * | 2006-12-28 | 2007-12-28 | 주식회사 효성 | 폴리케톤의 제조방법 |
| JP2009242810A (ja) * | 2009-07-28 | 2009-10-22 | Asahi Kasei Fibers Corp | 繊維強化複合材料及びその製造方法 |
| KR101076649B1 (ko) | 2009-12-30 | 2011-10-26 | 주식회사 효성 | 폴리케톤 섬유의 제조방법 |
| DE102010017786A1 (de) * | 2010-07-07 | 2012-01-12 | Continental Reifen Deutschland Gmbh | Elastomerprodukt, enthaltend ein linienförmiges, textiles Gebilde zur Verstärkung |
| KR101725811B1 (ko) * | 2010-12-23 | 2017-04-12 | 주식회사 효성 | 폴리케톤 섬유의 제조 방법 |
| EP2749588B1 (en) | 2011-09-09 | 2015-12-16 | Asahi Kasei Fibers Corporation | Polyketone porous film |
| KR101684880B1 (ko) | 2014-11-19 | 2016-12-12 | 주식회사 효성 | 자동차의 라디에이터 엔드 탱크용 폴리케톤 수지 조성물 |
| KR101664221B1 (ko) | 2014-11-07 | 2016-10-11 | 주식회사 효성 | 폴리케톤 자동차 외장 휠 커버 |
| KR101675285B1 (ko) | 2014-11-19 | 2016-11-11 | 주식회사 효성 | 폴리케톤 폴리머를 포함하는 축전지용 가스켓 |
| KR101684889B1 (ko) | 2014-11-19 | 2016-12-12 | 주식회사 효성 | 폴리케톤 엔진 부품 |
| KR101629841B1 (ko) * | 2014-11-19 | 2016-06-14 | 주식회사 효성 | 폴리케톤 블렌드를 포함하는 케이블 타이 |
| KR101684887B1 (ko) | 2014-11-19 | 2016-12-12 | 주식회사 효성 | 폴리케톤 폴리머를 포함하는 음용수용 부품 |
| KR101646034B1 (ko) | 2014-11-07 | 2016-08-05 | 주식회사 효성 | 폴리케톤 커넥터 |
| KR101655336B1 (ko) | 2014-11-19 | 2016-09-07 | 주식회사 효성 | 폴리케톤 범퍼 브라켓 |
| KR101684885B1 (ko) | 2014-11-19 | 2016-12-12 | 주식회사 효성 | 노트북 하단 하우징으로 사용 가능한 폴리케톤 수지 조성물 |
| KR101675283B1 (ko) | 2014-11-19 | 2016-11-11 | 주식회사 효성 | 폴리케톤 폴리머를 포함하는 전자렌지용 용기 |
| KR101611580B1 (ko) | 2014-11-19 | 2016-04-11 | 주식회사 효성 | 폴리케톤 블렌드를 포함하는 신발용 소재 |
| KR101664249B1 (ko) | 2014-11-07 | 2016-10-11 | 주식회사 효성 | 폴리케톤 전자레인지 부품 |
| KR101675286B1 (ko) | 2014-11-19 | 2016-11-22 | 주식회사 효성 | 폴리케톤 블렌드를 포함하는 전기전자제품용 뚜껑 |
| KR101664921B1 (ko) * | 2014-11-19 | 2016-10-11 | 주식회사 효성 | 저융점 폴리케톤의 제조방법 |
| CN117223964A (zh) * | 2016-09-29 | 2023-12-15 | 株式会社Lg生活健康 | 聚酮材质的牙刷毛及包括该牙刷毛的牙刷 |
| KR20200109296A (ko) * | 2017-12-16 | 2020-09-22 | 로베르트 보쉬 게엠베하 | 고전압 리튬 이온 전지용 폴리(케톤)-계 폴리머 전해질 |
| KR20200016021A (ko) | 2018-08-06 | 2020-02-14 | 유한회사 삼성하이텍 | 기능성 액체보관 다층용기 제조방법 |
| CN113646066B (zh) | 2019-03-29 | 2024-05-31 | 旭化成医疗株式会社 | 蛋白质的纯化方法 |
| KR102395060B1 (ko) * | 2020-10-13 | 2022-05-09 | 금호타이어 주식회사 | 타이어용 고무 조성물 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0121965B1 (en) * | 1983-04-06 | 1989-12-27 | Shell Internationale Researchmaatschappij B.V. | Process for the preparation of polyketones |
| US4855400A (en) * | 1985-11-26 | 1989-08-08 | Shell Oil Company | Removal of catalyst residues from carbon monoxide/olefin polymers with catalyst complexing agent |
| NL8602164A (nl) * | 1986-08-26 | 1988-03-16 | Shell Int Research | Katalysatorcomposities. |
| JP2587856B2 (ja) | 1987-03-27 | 1997-03-05 | シエル・インターナシヨナル，リサーチ・マートスハツペイ・ベー・ヴエー | オレフィン／ｃｏコポリマーからの触媒残留物の除去 |
| US4855401A (en) * | 1987-04-27 | 1989-08-08 | Shell Oil Company | Removal of catalyst remnants from carbon monoxide/olefin polymers at temperatures higher than polymerization temperatures |
| EP0319083A3 (en) * | 1987-11-30 | 1990-11-07 | Shell Internationale Researchmaatschappij B.V. | Polyketone polymer preparation |
| US4839437A (en) * | 1988-04-29 | 1989-06-13 | Shell Oil Company | Blends of polyketone polymer with an at least partially crystalline polyamide polymer |
| EP0339745B1 (en) | 1988-04-29 | 1995-01-18 | Shell Internationale Researchmaatschappij B.V. | Polyketone polymer composition |
| US5001221A (en) | 1988-09-19 | 1991-03-19 | Shell Oil Company | Polymerization of carbon monoxide/olefin with catalyst/diluent recycle |
| EP0456306B1 (en) | 1990-05-09 | 1995-12-13 | Akzo Nobel N.V. | Process for making polyketone fibres |
| US5237047A (en) * | 1991-05-01 | 1993-08-17 | Shell Oil Company | Polymerization of co/olefin wth catalyst chemically bound to particles of support |
| US5955019A (en) | 1997-10-06 | 1999-09-21 | Shell Oil Company | Solution spinning polyketone fibers |
| DE69918845T2 (de) * | 1998-08-10 | 2005-07-21 | Asahi Kasei Kabushiki Kaisha | Polyketonlösung |
| CN1353733A (zh) | 1999-05-10 | 2002-06-12 | 国际壳牌研究有限公司 | 制备一氧化碳与烯属不饱和化合物共聚物的方法 |
| JP2000345431A (ja) * | 1999-06-07 | 2000-12-12 | Asahi Chem Ind Co Ltd | ポリケトン繊維及びその製造方法 |
| WO2001002463A1 (en) | 1999-07-06 | 2001-01-11 | Shell Internationale Research Maatschappij B.V. | Catalyst composition and use thereof |
| JP2001098066A (ja) * | 1999-09-29 | 2001-04-10 | Asahi Kasei Corp | 高分子量ポリマー |
| JP2002317044A (ja) * | 2001-04-18 | 2002-10-31 | Asahi Kasei Corp | ポリケトンの製造方法 |
| JP4228613B2 (ja) | 2002-07-31 | 2009-02-25 | 日本電気株式会社 | シリアルディジタル信号伝送方式 |
-
2002
- 2002-12-24 AT AT02786195T patent/ATE361941T1/de not_active IP Right Cessation
- 2002-12-24 JP JP2003556461A patent/JP4601294B2/ja not_active Expired - Fee Related
- 2002-12-24 EP EP02786195A patent/EP1460097B1/en not_active Expired - Lifetime
- 2002-12-24 AU AU2002354267A patent/AU2002354267A1/en not_active Abandoned
- 2002-12-24 WO PCT/JP2002/013451 patent/WO2003055934A1/ja not_active Ceased
- 2002-12-24 ES ES02786195T patent/ES2282493T3/es not_active Expired - Lifetime
- 2002-12-24 US US10/500,190 patent/US20050075475A1/en not_active Abandoned
- 2002-12-24 DE DE60220096T patent/DE60220096T2/de not_active Expired - Lifetime
- 2002-12-24 KR KR1020047010093A patent/KR100668572B1/ko not_active Expired - Fee Related
- 2002-12-25 TW TW091137327A patent/TW200302236A/zh not_active IP Right Cessation
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2005
- 2005-12-29 US US11/320,531 patent/US20060135738A1/en not_active Abandoned
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|---|---|
| EP1460097A4 (en) | 2006-03-08 |
| EP1460097B1 (en) | 2007-05-09 |
| KR20040076271A (ko) | 2004-08-31 |
| WO2003055934A1 (en) | 2003-07-10 |
| US20080262189A1 (en) | 2008-10-23 |
| US20060135738A1 (en) | 2006-06-22 |
| EP1460097A1 (en) | 2004-09-22 |
| AU2002354267A1 (en) | 2003-07-15 |
| US20050075475A1 (en) | 2005-04-07 |
| ATE361941T1 (de) | 2007-06-15 |
| TW200302236A (en) | 2003-08-01 |
| DE60220096T2 (de) | 2008-01-10 |
| JP4601294B2 (ja) | 2010-12-22 |
| KR100668572B1 (ko) | 2007-01-16 |
| JPWO2003055934A1 (ja) | 2005-05-12 |
| DE60220096D1 (de) | 2007-06-21 |
| US7666975B2 (en) | 2010-02-23 |
| TWI304418B (https=) | 2008-12-21 |
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