BR112012006015B1 - Processo para a produção de borrachas de nitrila, borracha de nitrila, misturas vulcanizáveis, processo para a produção de vulcanizados, e vulcanizados - Google Patents

Info

Publication number

BR112012006015B1

BR112012006015B1 BR112012006015-5A BR112012006015A BR112012006015B1 BR 112012006015 B1 BR112012006015 B1 BR 112012006015B1 BR 112012006015 A BR112012006015 A BR 112012006015A BR 112012006015 B1 BR112012006015 B1 BR 112012006015B1

Authority

BR

Brazil

Prior art keywords

radical

petition

nitrile

rubber

mono

Prior art date

2009-09-17

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 41
• 238000004519 manufacturing process Methods 0.000 title claims abstract description 36
• 230000008569 process Effects 0.000 title claims abstract description 24
• 239000000203 mixture Substances 0.000 title claims description 30
• 229920001971 elastomer Polymers 0.000 title claims description 26
• 239000005060 rubber Substances 0.000 title claims description 25
• 229920000459 Nitrile rubber Polymers 0.000 claims abstract description 184
• 229920000642 polymer Polymers 0.000 claims abstract description 48
• 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 22
• 239000003960 organic solvent Substances 0.000 claims abstract description 14
• 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 11
• -1 polyunsaturated alkyl radical Chemical class 0.000 claims description 145
• 150000003254 radicals Chemical class 0.000 claims description 48
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 45
• 150000001993 dienes Chemical class 0.000 claims description 45
• 239000000178 monomer Substances 0.000 claims description 43
• 239000003999 initiator Substances 0.000 claims description 42
• 229920006395 saturated elastomer Polymers 0.000 claims description 36
• 125000005842 heteroatom Chemical group 0.000 claims description 32
• 150000002825 nitriles Chemical class 0.000 claims description 28
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 26
• 150000002148 esters Chemical class 0.000 claims description 26
• 239000004593 Epoxy Substances 0.000 claims description 23
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
• 125000004429 atom Chemical group 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 19
• 239000004971 Cross linker Substances 0.000 claims description 18
• 150000001875 compounds Chemical class 0.000 claims description 18
• 238000004132 cross linking Methods 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 125000004104 aryloxy group Chemical group 0.000 claims description 17
• 125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 claims description 17
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 16
• 239000012948 isocyanate Substances 0.000 claims description 16
• 150000002513 isocyanates Chemical class 0.000 claims description 15
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 239000000654 additive Substances 0.000 claims description 13
• 125000005110 aryl thio group Chemical group 0.000 claims description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 12
• 125000004414 alkyl thio group Chemical group 0.000 claims description 12
• 150000005840 aryl radicals Chemical class 0.000 claims description 12
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• LZOZLBFZGFLFBV-UHFFFAOYSA-N sulfene Chemical compound C=S(=O)=O LZOZLBFZGFLFBV-UHFFFAOYSA-N 0.000 claims description 11
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 11
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
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• 125000004043 oxo group Chemical group O=* 0.000 claims description 10
• 150000003457 sulfones Chemical class 0.000 claims description 10
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• 125000000464 thioxo group Chemical group S=* 0.000 claims description 10
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
• 229910052794 bromium Inorganic materials 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 8
• 150000005690 diesters Chemical class 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• QLOMMFARVWCHAZ-UHFFFAOYSA-N 2-phenylpropan-2-yl 2-phenylethanedithioate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=S)CC1=CC=CC=C1 QLOMMFARVWCHAZ-UHFFFAOYSA-N 0.000 claims description 7
• 239000002253 acid Substances 0.000 claims description 7
• 239000000945 filler Substances 0.000 claims description 7
• 229910052739 hydrogen Inorganic materials 0.000 claims description 7
• 150000002527 isonitriles Chemical class 0.000 claims description 7
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
• RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
• 150000001913 cyanates Chemical class 0.000 claims description 6
• 150000001991 dicarboxylic acids Chemical class 0.000 claims description 6
• ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 6
• 229920005862 polyol Polymers 0.000 claims description 6
• 150000003077 polyols Chemical class 0.000 claims description 6
• 229920001296 polysiloxane Polymers 0.000 claims description 6
• 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
• 150000003460 sulfonic acids Chemical class 0.000 claims description 6
• 150000003567 thiocyanates Chemical class 0.000 claims description 6
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 5
• 239000004952 Polyamide Substances 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 150000001408 amides Chemical class 0.000 claims description 5
• 150000004676 glycans Chemical class 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 5
• 229920001521 polyalkylene glycol ether Polymers 0.000 claims description 5
• 229920002647 polyamide Polymers 0.000 claims description 5
• 229920000515 polycarbonate Polymers 0.000 claims description 5
• 239000004417 polycarbonate Substances 0.000 claims description 5
• 229920000728 polyester Polymers 0.000 claims description 5
• 229920000570 polyether Polymers 0.000 claims description 5
• 239000005056 polyisocyanate Substances 0.000 claims description 5
• 229920001228 polyisocyanate Polymers 0.000 claims description 5
• 229920001282 polysaccharide Polymers 0.000 claims description 5
• 239000005017 polysaccharide Substances 0.000 claims description 5
• 239000004814 polyurethane Substances 0.000 claims description 5
• 229920002635 polyurethane Polymers 0.000 claims description 5
• 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 5
• 229920002554 vinyl polymer Polymers 0.000 claims description 5
• SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims description 4
• 150000001337 aliphatic alkines Chemical class 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 150000008064 anhydrides Chemical class 0.000 claims description 3
• 150000001642 boronic acid derivatives Chemical class 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 claims description 3
• KSYJPKPGLJRYJV-UHFFFAOYSA-N s-benzoylsulfanylcarbothioyl benzenecarbothioate Chemical compound C=1C=CC=CC=1C(=O)SC(=S)SC(=O)C1=CC=CC=C1 KSYJPKPGLJRYJV-UHFFFAOYSA-N 0.000 claims description 3
• QYHFIVBSNOWOCQ-UHFFFAOYSA-N selenic acid Chemical class O[Se](O)(=O)=O QYHFIVBSNOWOCQ-UHFFFAOYSA-N 0.000 claims description 3
• PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 2
• CFMTUIKADIKXIQ-UHFFFAOYSA-N 1-ethenoxy-3-fluoropropane Chemical compound FCCCOC=C CFMTUIKADIKXIQ-UHFFFAOYSA-N 0.000 claims description 2
• JXPLECNKPVHWMG-UHFFFAOYSA-N 2-phenylethyl benzenecarbodithioate Chemical compound C=1C=CC=CC=1C(=S)SCCC1=CC=CC=C1 JXPLECNKPVHWMG-UHFFFAOYSA-N 0.000 claims description 2
• KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 2
• BBDKZWKEPDTENS-UHFFFAOYSA-N 4-Vinylcyclohexene Chemical compound C=CC1CCC=CC1 BBDKZWKEPDTENS-UHFFFAOYSA-N 0.000 claims description 2
• YSIUOTWIDXMASD-UHFFFAOYSA-N 4-[(3-ethenylphenyl)methoxy]-n-phenylaniline Chemical compound C=CC1=CC=CC(COC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 YSIUOTWIDXMASD-UHFFFAOYSA-N 0.000 claims description 2
• GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
• 101100156282 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) vib-1 gene Proteins 0.000 claims description 2
• 230000004913 activation Effects 0.000 claims description 2
• XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
• QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 claims description 2
• PCJOWTXKIHRMGA-UHFFFAOYSA-N carbonotrithioic acid;2-methyltetradecanoic acid Chemical compound SC(S)=S.CCCCCCCCCCCCC(C)C(O)=O PCJOWTXKIHRMGA-UHFFFAOYSA-N 0.000 claims description 2
• GYBNBQFUPDFFQX-UHFFFAOYSA-N cyclohex-3-ene-1-carbonitrile Chemical compound N#CC1CCC=CC1 GYBNBQFUPDFFQX-UHFFFAOYSA-N 0.000 claims description 2
• IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 2
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• 238000010494 dissociation reaction Methods 0.000 claims 11
• 230000005593 dissociations Effects 0.000 claims 11
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
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• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
• AMEXFSCNSLCWPN-UHFFFAOYSA-N 2-cyanopropan-2-yl 2,2-dithiophen-2-ylacetate Chemical compound C=1C=CSC=1C(C(=O)OC(C)(C)C#N)C1=CC=CS1 AMEXFSCNSLCWPN-UHFFFAOYSA-N 0.000 claims 1
• IDSLBLWCPSAZBL-UHFFFAOYSA-N 2-cyanopropan-2-yl benzenecarbodithioate Chemical compound N#CC(C)(C)SC(=S)C1=CC=CC=C1 IDSLBLWCPSAZBL-UHFFFAOYSA-N 0.000 claims 1
• INZLZTHXPOJSCN-UHFFFAOYSA-N 3-fluoroprop-1-enylbenzene Chemical compound FCC=CC1=CC=CC=C1 INZLZTHXPOJSCN-UHFFFAOYSA-N 0.000 claims 1
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• QRGLHPKCXDINKY-UHFFFAOYSA-N ethenyl 2,3,4,5,6-pentafluorobenzoate Chemical compound FC1=C(F)C(F)=C(C(=O)OC=C)C(F)=C1F QRGLHPKCXDINKY-UHFFFAOYSA-N 0.000 claims 1
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• 239000003054 catalyst Substances 0.000 description 14
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• 239000000047 product Substances 0.000 description 6
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