TWI511981B - 製造無水及溶劑之腈橡膠之方法 - Google Patents

Info

Publication number

TWI511981B

TWI511981B TW100110105A TW100110105A TWI511981B TW I511981 B TWI511981 B TW I511981B TW 100110105 A TW100110105 A TW 100110105A TW 100110105 A TW100110105 A TW 100110105A TW I511981 B TWI511981 B TW I511981B

Authority

TW

Taiwan

Prior art keywords

group

nitrile rubber

extruder

fluid

zone

Prior art date

2010-03-25

Links

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• Global Dossier
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• 229920000459 Nitrile rubber Polymers 0.000 title claims description 122
• 238000000034 method Methods 0.000 title claims description 96
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 34
• 230000008569 process Effects 0.000 title description 20
• 238000004519 manufacturing process Methods 0.000 title description 7
• -1 aromatic Alkyl Chemical group 0.000 claims description 134
• 239000012530 fluid Substances 0.000 claims description 125
• 238000007872 degassing Methods 0.000 claims description 70
• 150000001875 compounds Chemical class 0.000 claims description 54
• 125000003118 aryl group Chemical group 0.000 claims description 42
• 239000000178 monomer Substances 0.000 claims description 38
• 229920006395 saturated elastomer Polymers 0.000 claims description 34
• 229920000642 polymer Polymers 0.000 claims description 32
• 238000009825 accumulation Methods 0.000 claims description 26
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
• 150000002148 esters Chemical class 0.000 claims description 21
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
• 150000001993 dienes Chemical class 0.000 claims description 19
• 239000000654 additive Substances 0.000 claims description 18
• 238000001816 cooling Methods 0.000 claims description 18
• 150000002825 nitriles Chemical class 0.000 claims description 18
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
• 239000003795 chemical substances by application Substances 0.000 claims description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 17
• 150000001412 amines Chemical class 0.000 claims description 16
• 125000002837 carbocyclic group Chemical group 0.000 claims description 16
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 16
• 239000003039 volatile agent Substances 0.000 claims description 16
• 238000004898 kneading Methods 0.000 claims description 15
• 125000005323 thioketone group Chemical group 0.000 claims description 15
• 238000003303 reheating Methods 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
• 125000004104 aryloxy group Chemical group 0.000 claims description 12
• 125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 claims description 12
• 239000012634 fragment Substances 0.000 claims description 11
• 229920000768 polyamine Polymers 0.000 claims description 11
• 238000011144 upstream manufacturing Methods 0.000 claims description 11
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 10
• 125000005110 aryl thio group Chemical group 0.000 claims description 10
• 238000010438 heat treatment Methods 0.000 claims description 10
• 125000003700 epoxy group Chemical group 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 125000001072 heteroaryl group Chemical group 0.000 claims description 9
• 239000012948 isocyanate Substances 0.000 claims description 9
• 150000002513 isocyanates Chemical class 0.000 claims description 9
• NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims description 9
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 9
• 238000012545 processing Methods 0.000 claims description 9
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 9
• 239000004593 Epoxy Substances 0.000 claims description 8
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 8
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 8
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 7
• 239000002253 acid Substances 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
• 150000001345 alkine derivatives Chemical class 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 239000004417 polycarbonate Substances 0.000 claims description 6
• 229920000515 polycarbonate Polymers 0.000 claims description 6
• 229920005862 polyol Polymers 0.000 claims description 6
• 150000003077 polyols Chemical class 0.000 claims description 6
• BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 5
• 150000004676 glycans Chemical class 0.000 claims description 5
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
• DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims description 5
• 229920000570 polyether Polymers 0.000 claims description 5
• 229920001228 polyisocyanate Polymers 0.000 claims description 5
• 239000005056 polyisocyanate Substances 0.000 claims description 5
• 229920001282 polysaccharide Polymers 0.000 claims description 5
• 239000005017 polysaccharide Substances 0.000 claims description 5
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 5
• 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 4
• SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 4
• 238000005469 granulation Methods 0.000 claims description 4
• 230000003179 granulation Effects 0.000 claims description 4
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 229920000728 polyester Polymers 0.000 claims description 4
• 229920002635 polyurethane Polymers 0.000 claims description 4
• 239000004814 polyurethane Substances 0.000 claims description 4
• 125000006612 decyloxy group Chemical group 0.000 claims description 3
• 238000006073 displacement reaction Methods 0.000 claims description 3
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 3
• OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 3
• 239000007921 spray Substances 0.000 claims description 3
• 239000004952 Polyamide Substances 0.000 claims description 2
• 230000000996 additive effect Effects 0.000 claims description 2
• 239000002826 coolant Substances 0.000 claims description 2
• 239000007788 liquid Substances 0.000 claims description 2
• 229920002647 polyamide Polymers 0.000 claims description 2
• 229920006149 polyester-amide block copolymer Polymers 0.000 claims description 2
• 125000000626 sulfinic acid group Chemical group 0.000 claims description 2
• XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 3
• RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 2
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
• AQWRIVFRBUIJSV-UHFFFAOYSA-N N=NC=NN.C(N)(=N)N Chemical compound N=NC=NN.C(N)(=N)N AQWRIVFRBUIJSV-UHFFFAOYSA-N 0.000 claims 1
• 239000005864 Sulphur Substances 0.000 claims 1
• CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims 1
• 229960005286 carbaryl Drugs 0.000 claims 1
• JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 claims 1
• 238000004891 communication Methods 0.000 claims 1
• 239000004643 cyanate ester Substances 0.000 claims 1
• WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 claims 1
• QQEWMMRFXYVLQU-UHFFFAOYSA-N decylhydrazine Chemical compound CCCCCCCCCCNN QQEWMMRFXYVLQU-UHFFFAOYSA-N 0.000 claims 1
• CYFLXLSBHQBMFT-UHFFFAOYSA-N sulfamoxole Chemical group O1C(C)=C(C)N=C1NS(=O)(=O)C1=CC=C(N)C=C1 CYFLXLSBHQBMFT-UHFFFAOYSA-N 0.000 claims 1
• 125000000944 sulfenic acid group Chemical group 0.000 claims 1
• 150000003573 thiols Chemical class 0.000 claims 1
• 239000000047 product Substances 0.000 description 39
• 239000002585 base Substances 0.000 description 24
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 22
• 239000000203 mixture Substances 0.000 description 21
• 239000002904 solvent Substances 0.000 description 18
• 125000000217 alkyl group Chemical group 0.000 description 17
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 17
• 239000003999 initiator Substances 0.000 description 17
• 238000004132 cross linking Methods 0.000 description 16
• 229920001971 elastomer Polymers 0.000 description 16
• 238000006116 polymerization reaction Methods 0.000 description 16
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 15
• 239000003431 cross linking reagent Substances 0.000 description 15
• 125000005842 heteroatom Chemical group 0.000 description 15
• 239000005060 rubber Substances 0.000 description 15
• 150000003839 salts Chemical class 0.000 description 15
• 239000011593 sulfur Substances 0.000 description 14
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 13
• 125000001424 substituent group Chemical group 0.000 description 13
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
• 125000004429 atom Chemical group 0.000 description 12
• RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 12
• 238000006243 chemical reaction Methods 0.000 description 11
• 239000000463 material Substances 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
• 125000005907 alkyl ester group Chemical group 0.000 description 10
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
• 239000012855 volatile organic compound Substances 0.000 description 10
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
• 239000003960 organic solvent Substances 0.000 description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
• 238000010526 radical polymerization reaction Methods 0.000 description 9
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 8
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
• 239000000945 filler Substances 0.000 description 8
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
• 125000004076 pyridyl group Chemical group 0.000 description 8
• 239000001530 fumaric acid Substances 0.000 description 7
• LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 7
• QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 7
• 230000001105 regulatory effect Effects 0.000 description 7
• YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 6
• JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 6
• BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 6
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
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• 239000011701 zinc Substances 0.000 description 6
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• 238000009826 distribution Methods 0.000 description 5
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• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
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• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
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• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 4
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
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• 230000008901 benefit Effects 0.000 description 4
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• 230000008859 change Effects 0.000 description 4
• 239000000460 chlorine Substances 0.000 description 4
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• 238000000576 coating method Methods 0.000 description 4
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• 235000014113 dietary fatty acids Nutrition 0.000 description 4
• 229940113088 dimethylacetamide Drugs 0.000 description 4
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• 239000001257 hydrogen Substances 0.000 description 4
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• IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
• 150000002576 ketones Chemical class 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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• 238000005054 agglomeration Methods 0.000 description 3
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• 125000001931 aliphatic group Chemical group 0.000 description 3
• 125000003277 amino group Chemical group 0.000 description 3
• 239000001273 butane Substances 0.000 description 3
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
• 125000004432 carbon atom Chemical group C* 0.000 description 3
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• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
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