TW201540761A - 安定化橡膠 - Google Patents
安定化橡膠 Download PDFInfo
- Publication number
- TW201540761A TW201540761A TW104103520A TW104103520A TW201540761A TW 201540761 A TW201540761 A TW 201540761A TW 104103520 A TW104103520 A TW 104103520A TW 104103520 A TW104103520 A TW 104103520A TW 201540761 A TW201540761 A TW 201540761A
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- TW
- Taiwan
- Prior art keywords
- rubber
- group
- iii
- stabilized
- unsaturated
- Prior art date
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- 229920001971 elastomer Polymers 0.000 title claims abstract description 126
- 239000005060 rubber Substances 0.000 title claims abstract description 125
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 239000000203 mixture Substances 0.000 claims abstract description 60
- 238000000034 method Methods 0.000 claims abstract description 25
- 229920000459 Nitrile rubber Polymers 0.000 claims description 145
- -1 polyoxyethylene-oxypropylene Polymers 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 239000000178 monomer Substances 0.000 claims description 40
- 229920006395 saturated elastomer Polymers 0.000 claims description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 33
- 239000003381 stabilizer Substances 0.000 claims description 33
- 239000002270 dispersing agent Substances 0.000 claims description 30
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 30
- 238000006116 polymerization reaction Methods 0.000 claims description 27
- 150000002825 nitriles Chemical class 0.000 claims description 26
- 239000004636 vulcanized rubber Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 150000001993 dienes Chemical class 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 238000005984 hydrogenation reaction Methods 0.000 claims description 21
- 239000003963 antioxidant agent Substances 0.000 claims description 20
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000003431 cross linking reagent Substances 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 238000005649 metathesis reaction Methods 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims description 11
- 125000005110 aryl thio group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 230000003078 antioxidant effect Effects 0.000 claims description 9
- 238000004132 cross linking Methods 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- 150000002978 peroxides Chemical class 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- 229920006168 hydrated nitrile rubber Polymers 0.000 claims description 6
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 6
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000002431 hydrogen Chemical class 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000007983 Tris buffer Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 238000007711 solidification Methods 0.000 claims description 4
- 230000008023 solidification Effects 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- 229920005557 bromobutyl Polymers 0.000 claims description 2
- 229920005549 butyl rubber Polymers 0.000 claims description 2
- 229920005556 chlorobutyl Polymers 0.000 claims description 2
- 230000001804 emulsifying effect Effects 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- FGHOOJSIEHYJFQ-UHFFFAOYSA-N (2,4-ditert-butylphenyl) dihydrogen phosphite Chemical compound CC(C)(C)C1=CC=C(OP(O)O)C(C(C)(C)C)=C1 FGHOOJSIEHYJFQ-UHFFFAOYSA-N 0.000 claims 1
- 241000208340 Araliaceae Species 0.000 claims 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 claims 1
- 235000003140 Panax quinquefolius Nutrition 0.000 claims 1
- 235000008434 ginseng Nutrition 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 26
- 230000003712 anti-aging effect Effects 0.000 abstract description 23
- 230000001976 improved effect Effects 0.000 abstract description 11
- 230000007774 longterm Effects 0.000 abstract description 7
- 230000008569 process Effects 0.000 abstract description 7
- 235000002639 sodium chloride Nutrition 0.000 description 32
- 230000032683 aging Effects 0.000 description 31
- 239000003995 emulsifying agent Substances 0.000 description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 23
- 150000003839 salts Chemical class 0.000 description 23
- 238000005345 coagulation Methods 0.000 description 22
- 230000015271 coagulation Effects 0.000 description 22
- 150000002148 esters Chemical class 0.000 description 22
- 229920000126 latex Polymers 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 21
- 239000004816 latex Substances 0.000 description 20
- 239000002253 acid Substances 0.000 description 19
- 239000002174 Styrene-butadiene Substances 0.000 description 17
- 239000000654 additive Substances 0.000 description 17
- 235000006708 antioxidants Nutrition 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
- 238000004321 preservation Methods 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 230000006641 stabilisation Effects 0.000 description 13
- 238000011105 stabilization Methods 0.000 description 13
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 229910052708 sodium Inorganic materials 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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 238000004140 cleaning Methods 0.000 description 10
- 150000005690 diesters Chemical class 0.000 description 10
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- 238000007720 emulsion polymerization reaction Methods 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 8
- 229960002447 thiram Drugs 0.000 description 8
- 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 8
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000003426 co-catalyst Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000012545 processing Methods 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
- 125000005907 alkyl ester group Chemical group 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000003792 electrolyte Substances 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
- 239000011780 sodium chloride Substances 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 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 150000007860 aryl ester derivatives Chemical class 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 235000011148 calcium chloride Nutrition 0.000 description 4
- 159000000007 calcium salts Chemical class 0.000 description 4
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- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
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- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
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- 229920000768 polyamine Polymers 0.000 description 4
- 235000011118 potassium hydroxide Nutrition 0.000 description 4
- 159000000001 potassium salts Chemical class 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- 239000010948 rhodium Substances 0.000 description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 4
- 125000004149 thio group Chemical group *S* 0.000 description 4
- 231100000331 toxic Toxicity 0.000 description 4
- 230000002588 toxic effect Effects 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 4
- KMYAABORDFJSLR-UHFFFAOYSA-N (carbamothioyltrisulfanyl) carbamodithioate Chemical compound NC(=S)SSSSC(N)=S KMYAABORDFJSLR-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241001441571 Hiodontidae Species 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 235000019817 tetrapotassium diphosphate Nutrition 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical group C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical group C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- PIMBTRGLTHJJRV-UHFFFAOYSA-L zinc;2-methylprop-2-enoate Chemical compound [Zn+2].CC(=C)C([O-])=O.CC(=C)C([O-])=O PIMBTRGLTHJJRV-UHFFFAOYSA-L 0.000 description 1
- NEYNBSGIXOOZGZ-UHFFFAOYSA-L zinc;butoxymethanedithioate Chemical compound [Zn+2].CCCCOC([S-])=S.CCCCOC([S-])=S NEYNBSGIXOOZGZ-UHFFFAOYSA-L 0.000 description 1
- HZFSIJCQPSIJHB-UHFFFAOYSA-L zinc;n-methylcarbamodithioate Chemical compound [Zn+2].CNC([S-])=S.CNC([S-])=S HZFSIJCQPSIJHB-UHFFFAOYSA-L 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
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Abstract
本發明係提供一種新穎橡膠,其係藉至少三種抗老化化合物之特定組合而安定化。不論短期或長期,該橡膠具增加之保存安定性及改進之色安定性。本發明亦有關一種用於生產該新穎橡膠之方法、基於其之硫化橡膠混合物,自此等混合物生產硫化橡膠之方法以及所獲得之硫化橡膠。
Description
本發明係有關一種包含抗老化化合物之特定組合之新穎橡膠、一種用於生產該新穎橡膠之方法、一種基於其之硫化橡膠混合物、一種由該等該些混合物生產硫化橡膠之方法、及由此所獲得的硫化橡膠。
有機聚合物或其硫化橡膠老化會導致各種性質改變,如聚合物硬度或脆裂度增加。或者,出現軟化、彈性或機械強度喪失。亦可觀察到破裂、表面改變、或其他變化,如電性。亦常發現不良氣味及變色現象。
前述性質改變及現象係因不同老化過程所致,如Handbuch für die Gummi-Industrie,2.völlig neu bearbeitete Ausgabe,1991,Seite 423 ff,Bayer AG,Geschäftsbereich Kautschuk,Anwendungstechnik之描述。
欲防止或減少該老化過程,本領域習知係加入抗老化化合物,其典型上可分為三不同類別:(i)單或寡官能性之二級芳族胺類,
(ii)單或寡官能性之經取代酚類,(iii)含化合物之雜環巰基。
當待保護之聚合物或硫化橡膠長時間曝露於較高溫時,該抗老化化合物之效果典型上出現低下。此外,理想的是,欲使用之抗老化化合物本身不具著色效果,而僅反而提供良好色安定性予橡膠或其硫化橡膠,並可用於結合過氧化物或硫系硫化劑。此外,一些習知之抗老化化合物具毒性風險,意指橡膠/硫化橡膠之安定性僅於使用有害物質時達成。此外,二苯基胺類,係應用於酚醛抗氧化劑,如Vulkanox® BKF,其歸類為H361f,即涉及損害生育能力。
由於橡膠及其硫化橡膠之高老化安定性需求增加,特別是曝露於高溫下之保存及色安定性,因此,必須持續提供新的改進概念,以防止及減少橡膠及硫化橡膠的老化過程。此目的亦涵蓋將抗老化化合物的量降至不會減少安定性效果之程度。
特別的是,於聚合物鏈上具不飽和C=C雙鍵之橡膠,如腈橡膠或苯乙烯-丁二烯橡膠,會出現老化現象。
腈橡膠及生產此類腈橡膠之方法係習知,參見如W.Hofmann,“Nitrilkautschuk”,Berliner Union Stuttgart 1965,pages 51-54,然而,未有指示如何進一步改進腈橡膠之保存安定性。
就本發明之目的,腈橡膠,亦縮寫成「NBR」,為共聚合物或三元聚合物之橡膠,其包含至少一α,β-不飽和腈、至少一共軛雙烯、及任意地一或多個進一步共聚合單體之重複單元。部分或完全氫化腈橡膠,亦縮寫成「HNBR」,係相對應之共或三元聚合物,其中共聚合雙烯重複單元之C=C雙鍵係部分或完全氫化。
多年來,NBR與HNBR已於特殊彈性體行業佔有一席之地。其具優異特性,如極佳耐油性、良好熱安定性、極佳臭氧及化學物質抗性,其中HNBR之熱安定性比NBR的更明顯。NBR與HNBR亦具極佳機械及性能特性。據此,其廣泛用於多種不同領域,如用於製造汽車行業之墊片、軟管、皮帶、及阻尼元件;用於製造石油生產業之定子、密封件、及閥門密封件;以及用於電子產業、機械工程業、及造船業之多種部件。商業上可購得多種不同類型,且該些特性依應用領域有不同的單體、分子量、多分散性、及機械與物理性質。除了標準類型以外,越來越需要特別是特定類別之特性內容的特定三元單體或特定官能性。
腈橡膠、苯乙烯丁二烯橡膠(「SBR」)或其他類型橡膠常有保存安定性及色安定性的問題。就本發明目的,保存安定性意指於長時間保存期間,特別是在高溫下,許多橡膠的重要規格標準慕尼黏度(Mooney viscosity)之改變盡可能少。進一步就本發明目的,色安定性意指於高溫保存後,根據CIEDE 2000測定,橡膠△E值盡可能小。
JP 75,105,746描述耐熱性腈橡膠,其係以乳膠凝固作用獲得,係藉加入二氯化錫與氯化鈣進行。然而,現今使用錫鹽有生態上疑慮,尤其是腈橡膠中可發現該些錫鹽,即使後續全面洗滌腈橡膠後亦然。自洗滌水中移除錫鹽之費用高,且可能有額外的淨化費用支出。
根據Angew.Makromol.Chem.1986,145-146,161-179,一種改進腈橡膠保存安定性之測定方式為選擇性氫化源自丁二烯之雙鍵,且同時保留腈基之參鍵。有許多應用但並非全部,
適合以氫化達成性質改變。此外,氫化係複雜,且需要一系列額外之加工步驟。由於常會測定氫化後的玻璃轉變溫度,並與未氫化起始材料相比,此類氫化並非所有應用相關問題之適當解答。
NBR係由乳化聚合作用產生,其首先產生NBR乳膠。NBR固體係藉凝固作用自此乳膠分離。鹽類及酸係用於凝固作用。於藉金屬鹽類之乳膠凝固作用中,習知之單價金屬離子如氯化鈉形式比多價金屬離子如氯化鈣、氯化鎂、或硫酸鋁形式需要明顯較大量之電解質(Kolloid-Z.154,154(1957))。由Houben-Weyl(1961),Methoden der Org.Chemie,Makromolekulare Stoffe 1,p.484亦習知,使用多價金屬離子導致「產物至少夾雜一些乳化劑」。根據該些參考資料,所使用之電解質必須非常小心地洗出,且成品亦應不含加工批次之觸媒與乳化劑。即使小量之殘餘電解質亦可能造成各性質之劣化。
根據DE-A 30 43 688之教學,可減少乳膠凝固作用所需之電解質量,係使用植物系類蛋白質材料或多醣如澱粉,且於乳膠之電解質凝固作用時,除了無機凝結劑以外,適時以水溶性多胺化合物作為輔劑。於無機凝結劑中,偏好為鹼金屬或鹼土金屬鹽類。特定添加劑可使得用於乳膠之定量凝固作用的鹽類量減少。DE-A 3 043 688未提供有關腈橡膠之產生及/或後處理時如何改進保存及色安定性之資訊。
EP-A-1 369 436之目的在於提供具高純度之腈橡膠。EP-A-1 369 436之加工始於典型腈橡膠。未提及聚合作用流程,除了作為乳化劑之脂肪酸及/或樹脂酸鹽類存在下進行乳化聚合作用以外。此之後為乳膠凝固作用,係藉由酸,任意地加入沈澱劑。於
酸中,可使用所有礦物質與有機酸,其容許設定所需之酸鹼值。此外,可使用額外之沈澱劑,就此目的,主要提及無機酸之鹼金屬鹽類如氯化鈉及硫酸鈉。由於酸之作用所形成之脂肪酸及樹脂酸係隨後以水性鹼金屬氫氧化物溶液洗出,且聚合物最後進行切變(shear),直到所得殘餘含水量低於20%為止。此切變作用之結果為,去除水分或殘餘水分,包括存於其中之離子含量及其他外來物質。揭示於實施例1與2之產物鈣含量分別僅為4與2ppm。EP-A-1 369 436未提及生產腈橡膠之資訊,其呈現增加之保存及色安定性。
EP-A-0 692 496、EP-A-0 779 301、及EP-A-0 779 300皆描述特定腈橡膠。腈橡膠含有10-60重量%之不飽和腈,且慕尼黏度之範圍為15-150,或根據EP-A-0 692 496,範圍為15-65,且每100mol之單體單元皆含有至少0.03mol之C12-C16-烷基硫基,其中此烷基硫基具至少三個三級碳原子及一個硫原子,其直接結合至三級碳原子之至少一者。於各情況中,腈橡膠係於C12-C16-烷基硫基存在下產生,該基團具相對應結構以作為分子量調節劑,其功用為「鏈轉移劑」,因此併入聚合物鏈作為端基。
關於乳膠凝固作用,EP-A-0 692 496、EP-A-0 779 301、及EP-A-0 779 300揭示,可使用任何凝結劑或單一烷化酚醛抗老化化合物,其未進一步規定。焦點在於腈橡膠,其本質上無鹵素,且經揭示具鹵素含量不超過3ppm,且聲稱該橡膠混合物具有利性質態樣、良好加工性,且加工期間模型低結垢。所得硫化橡膠據稱具良好耐低溫與耐油之組合,且具良好機械性質。未提及關於腈橡膠及其硫化橡膠之保存及色安定性等性質。
EP-A-0 488 550描述安定劑組成物,包含1)硫化物,其具一或多個硫化物基團-CH2-S-CH2-R,其中R為C1-C20烷基、烷基鏈烷酸酯、或2,4-雙(正辛基硫基)-6-4'-羥基-3',5'-二-三級丁基苯胺基)1,3,5-三,且至少二受阻酚類(2)與(3),其中(3)之空間位阻比另一者(2)的小。此類組成物可併入聚合物,以製成聚合物添加劑。該些聚合物添加劑可用於聚合物基質,以提供聚合物產物改進之物理及機械特性。其係用於高濃度之1-4重量%之聚合物,且焦點在於安定丙烯酸酯系橡膠。其用途顯示一些協同效用,然而,未有任何顯示改進之橡膠分子量安定性,亦無任何揭示或教導如何減少安定化系統之量。
於US-A-5,116,534,係揭示三不同安定劑之結合物,其宣稱可安定多種類之聚合物。該組成物由:(i)酚醛抗氧化劑、(ii)硫基二丙酸酯;以及(iii)亞磷酸鹽組成。關於欲使用之亞磷酸鹽(iii),係強調烷基取代之苯基亞磷酸鹽類如TNPP(三壬基苯基亞磷酸鹽)。然而,目前該亞磷酸鹽類被認為有害,係鑑於其有毒副產物,特別是壬基酚。US-A-5,116,534未提供任何提示是否該安定劑適於增加聚合物之色安定性。
WO-A-2009/138342揭示一種結合物之用途,該結合物包含:a)一空間上位阻之酚,其具至少一硫化物基團,如下式:
其中R1為C8-C12烷基,R2為氫、C1-C12烷基、環己基、1-甲基環己基、苄基、α-甲基苄基、α,α-二甲基苄基、或-CH2-S-R1,R3為C1-C12烷基、苄基、α-甲基苄基、α,α-二甲基苄基、或-CH2-S-R1,及R4為氫或甲基;以及b)一苯乙烯化二苯基胺,如下式:
以安定乳化聚合物或橡膠乳膠。然而,二苯基胺類為毒性關鍵。
JP 2010/077334A亦揭示不同安定劑之結合物,其包含含硫酚系抗氧化劑及胺系抗老化劑。據稱其於安定腈橡膠之用途導致改進之慕尼安定性(Mooney stability)及改進之色安定性。關於欲使用之空間上位阻之酚類及類胺安定劑之量,一廣泛範圍係經揭示。未提供揭示或教導如何利用特定抗氧化劑結合物產生進一步之協同效用。
EP-A-0 439 427描述水性乳化劑,包含10至40重量%之抗氧化劑,以乳化劑重量為基礎,該抗氧化劑包含至少:(A)一種酚醛抗氧化劑,及/或(B)一種硫基二丙酸酯;及/或(C)一種有機亞磷
酸鹽,此外尚有0.25至10重量%之界面活性劑,其係有機酸之鹽類,以及0.25至10重量%之醇。應強調的是,此類水性乳化劑於保存時安定、可易於製造、及適於安定各種類之聚合物。
WO 2005/023886 A係針對a)甲基甲基丙烯酸酯-丁二烯聚合物或苯乙烯接枝聚合物之安定化,其使用b)一空間上位阻之酚醛抗氧化劑,如式(I)、(II)、或(III)、或其混合物;以及c)一不同於式(II)之硫基醚。
於WO-A-2002/14419,以空間上位阻之酚之鹽類用於安定橡膠。安定劑之特徵為包含至少二酚醛羥基。較佳之空間上位阻之酚醛化合物係如下式:
其中R1、R2、及R3可相同或相異,R1、R2為C1-C12烷基或C5-C8環烷基,且R3為氫、C1-C8烷基、或C5-C6環烷基。然而,無任何揭示或任何教導如何進一步以特定安定劑結合物改進安定效率。
WO-A-2001/081458揭示用於有機聚合物之液體安定性混合物,其包含:a)一液體化合物,屬於空間上位阻之酚之基團,由酯類或酯類混合物組成,如通式(I):
其中R1與R2係相同或相異,代表直鏈或支鏈C1-C18烷基;R3代表直鏈或支鏈C8-C18烷基,或下列基團之一者:CH3-(CH2)p-CH2-
其中m與n為範圍0至11之整數,包括極值,且m+n為10或11,且p為12或13;
b)一固體化合物,屬於空間上位阻之酚之基團,如下式:
其中n為範圍0至10之整數,包括極值。
此安定性混合物據稱為液體,且藉共同加熱組分製備。此混合物之固有問題為水性聚合物分散劑之相容性不足。使用此類液體製備物時,其本質上於水性聚合物分散劑之安定效率不足,係因抗氧化劑混合物無法完全相容於水性聚合物分散劑。進一步揭示於WO-A-2001/81458,此混合物可用於結合其他安定劑,且列出19種不同類別之化合物及超過百種不同之抗氧化劑,以作為潛在進一步之安定劑。未揭示是否且如果是,何種安定劑之特定結合物可適於以協同方式改進橡膠安定性。
總之,可如是說,至今所論及,未有一方法或任何安定系統於毒性上無虞,使得必須提供橡膠改進之安定性,不論是慕尼黏度安定性或色安定性。
因此,本發明之目的為提供不飽和橡膠,其具良好保存安定性,不論是慕尼黏度或色安定性,其不含毒性上及環境上有害化合物,且同時具不變之良好加工性質,亦即良好之硫化態樣及有利之機械性質。
於具體實施例1,本發明提供一種安定化橡膠,包含(i)至少一式(I)化合物
其中n為1至10之範圍,(ii)至少一式(II)化合物
其中R1為氫;直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代烷基;飽和或一或多次不飽和碳環基或雜環基;芳基;雜芳基、芳基烷基、雜芳基烷基、聚氧基伸烷基醚,較佳為聚氧基乙烯醚、或聚氧基丙烯醚、或聚氧基乙烯-氧基丙烯醚;以及R2係相同或相異,且為直鏈或支鏈C1-C6烷基或C5-C6環烷基,以及(iii)至少一式(III)化合物
其中R3為直鏈或支鏈C1-C14烷基;以及R4為氫、直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代烷基;飽和或一或多次不飽和碳環基或雜環基;芳基;雜芳基、芳基烷基、雜芳基烷基、烷氧基、芳基氧基、雜芳基氧基、烷基硫基、或芳基硫基。
於另一具體實施例2,本發明係有關一種安定化橡膠,包含(i)至少一式(I)化合物
其中n為1至10之範圍;(ii)至少一式(II)化合物
其中R1為氫;直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代烷基;飽和或一或多次不飽和碳環基或雜環基;芳基;雜芳基、芳基烷基、雜芳基烷基、聚氧基伸烷基醚,較佳為聚氧基乙烯醚、或聚氧基丙烯醚、或聚氧基乙烯-氧基丙烯醚;以及R2係相同或相異,且為直鏈或支鏈C1-C6烷基或C5-C6環烷基;以及(iii)至少一式(III)化合物
其中R3為直鏈或支鏈C1-C14烷基;以及R4為氫、直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代烷基;飽和或一或多次不飽和碳環基或雜環基;芳基;雜芳基、芳基烷基、雜芳基烷基、烷氧基、芳基氧基、雜芳基氧基、烷基硫基、或芳基硫基。
本發明更有關一種製造安定化橡膠之方法,係將組分
(i)、(ii)、及(iii)接觸於橡膠。在另一具體實施例中,此種加入可藉由(1)於橡膠製備期間,包括橡膠之聚合及後處理,後者包含凝固與分離;或(2)於橡膠製備後之一或多個其他化學轉換步驟,如複分解反應(metathesis reaction)、氫化反應、或類聚合物類似物反應如接枝;及/或(3)於製備基於該腈橡膠之硫化橡膠混合物期間,或該腈橡膠於交聯前進行一或多個進一步化學轉換之後。本發明更有關由前述任一方法獲得之安定化橡膠。
本發明更有關一種硫化橡膠混合物,其含有至少一安定化橡膠,及至少一交聯劑,以及其製備方法、製備硫化混合物之硫化橡膠之方法,以及由其所得之硫化橡膠。
除非另有明確指出,實施方式及上述與下列所有定義皆適用本發明之具體實施例1及具體實施例2。
橡膠:
於本發明之一具體實施例,待安定化之橡膠係不飽和,或部分或完全氫化。
本發明可安定化之任何橡膠之實例為:NBR 腈橡膠,如以下更詳盡之定義,HNBR 部分或完全氫化腈橡膠,如以下更詳盡之定義,
SBR 苯乙烯-丁二烯共聚物,包括其羧基化衍生物,CR 聚氯平,BR 聚丁二烯,IIR 異丁烯-異戊二烯共聚物,較佳具異戊二烯含量0.5至10重量%,BIIR 溴化異丁烯-異戊二烯共聚物,較佳具溴含量0.1至10重量%,CIIR 氯化異丁烯-異戊二烯共聚物,較佳具氯含量0.1至10重量%,ABR 丁二烯-C1-4-烷基丙烯酸酯共聚物,NIR 丙烯腈異戊二烯橡膠,SIR 苯乙烯異戊二烯橡膠,IR 聚異戊二烯,NR 天然橡膠,ENR 環氧化天然橡膠,或其混合物。
於一較佳具體實施例,待安定化之橡膠含有C=C雙鍵。
腈橡膠:
本發明之一較佳具體實施例係有關待安定化之腈橡膠,其具衍生自至少一α,β-不飽和腈之重複單元、至少一共軛二烯、及無、一或多個其他共聚化單體。
α,β-不飽和腈,可使用任何習知之α,β-不飽和腈,較佳為(C3-C5)α,β-不飽和腈如丙烯腈、甲基丙烯腈、乙基丙烯腈、或其
混合物。特別偏好丙烯腈。
共軛二烯可為任何天然發生者。偏好使用(C4-C6)共軛二烯類。特別偏好1,3-丁二烯、異戊二烯、2,3-二甲基丁二烯、戊二烯、或其混合物。非常特別偏好1,3-丁二烯與異戊二烯或其混合物。尤其偏好1,3-丁二烯。
因此,用於本發明之較佳腈橡膠為具有衍生自丙烯腈與1,3-丁二烯之重複單元之共聚物。
除了共軛二烯與α,β-不飽和腈之外,該氫化腈橡膠可包含技術上習知之一或多個其他共聚化單體之重複單元,如α,β-不飽和(較佳為單不飽和)單羧酸、其酯類與醯胺類、α,β-不飽和(較佳為單不飽和)二羧酸、其單或二酯類,以及該α,β-不飽和二羧酸之酸酐或醯胺。
較佳為使用α,β-不飽和單羧酸丙烯酸及甲基丙烯酸。
亦可使用α,β-不飽和單羧酸之酯類,尤其是烷基酯、烷氧基烷基酯、芳基酯、環烷基酯、氰基烷基酯、羥基烷基酯、及氟烷基酯。
就烷基酯而言,較佳為使用α,β-不飽和單羧酸之C1-C18烷基酯,更佳為丙烯酸或甲基丙烯酸之C1-C18烷基酯類,如甲基丙烯酸酯、乙基丙烯酸酯、丙基丙烯酸酯、正丁基丙烯酸酯、三級丁基丙烯酸酯、2-乙基-己基丙烯酸酯、正十二烷基丙烯酸酯、甲基甲基丙烯酸酯、乙基甲基丙烯酸酯、丙基甲基丙烯酸酯、正丁基甲基丙烯酸酯、三級丁基甲基丙烯酸酯、及2-乙基己基-甲基丙烯酸酯。
就烷氧基烷基酯而言,較佳為使用α,β-不飽和單羧酸之C2-C18烷氧基烷基酯,更佳為丙烯酸或甲基丙烯酸之烷氧基烷基
酯,如甲氧基甲基(甲基)丙烯酸酯、甲氧基乙基(甲基)丙烯酸酯、乙氧基乙基(甲基)丙烯酸酯、及甲氧基乙基(甲基)丙烯酸酯。
可使用芳基酯,較佳為C6-C14-芳基-,更佳為C6-C10-芳基酯,最佳為前述之丙烯酸酯與甲基丙烯酸酯之芳基酯。
在另一具體實施例中,使用環烷基酯,較佳為C5-C12-,更佳為C6-C12-環-烷基,最佳為前述之環烷基丙烯酸酯及甲基丙烯酸酯。
亦可使用氰基烷基酯,尤其是氰基烷基丙烯酸酯或氰基烷基 甲基丙烯酸酯,其中氰基烷基具2至12個碳原子,較佳為α-氰基乙基丙烯酸酯、β-氰基乙基丙烯酸酯、或氰基丁基甲基丙烯酸酯。
於另一具體實施例,係使用羥基烷基酯,尤其是羥基烷基丙烯酸酯與羥基烷基甲基丙烯酸酯,其中羥基烷基具1至12個碳原子,較佳為2-羥基乙基丙烯酸酯、2-羥基乙基甲基丙烯酸酯、或3-羥基丙基丙烯酸酯。
亦可使用氟化苄基酯,尤其是氟化苄基丙烯酸酯或氟
化苄基甲基丙烯酸酯,較佳為三氟乙基丙烯酸酯與四氟丙基甲基丙烯酸酯。亦可使用含有丙烯酸酯與甲基丙烯酸酯之經取代胺基,如二甲基胺基甲基丙烯酸酯與二乙基胺基乙基丙烯酸酯。
亦可使用α,β-不飽和羧酸之各式其他酯類,如聚乙二醇(甲基)丙烯酸酯、聚丙二醇(甲基)丙烯酸酯、縮水甘油基(甲基)丙烯酸酯、環氧基(甲基)丙烯酸酯、N-(2-羥基乙基)丙烯醯胺、N-(2-羥基甲基)丙烯醯胺、或氨基甲酸酯(甲基)丙烯酸酯。
亦可使用前述α,β-不飽和羧酸之酯類。
此外,可使用α,β-不飽和二羧酸,較佳為馬來酸、富馬酸、巴豆酸、衣康酸、檸康酸、及中康酸。
於另一具體實施例,係使用α,β-不飽和二羧酸酐,較佳為馬來酸酐、衣康酸酐、衣康酸酐、檸康酸酐、及中康酸酐。
於又一具體實施例,可使用α,β-不飽和二羧酸之單-或二酯。適當之烷基酯為如C1-C10-烷基,較佳為乙基-、正丙基-、異丙基、正丁基-、三級丁基、正戊基-、或正己基單-或二酯。適當之烷氧基烷基酯如C2-C12烷氧基烷基-,較佳為C3-C8-烷氧基烷基單-或二酯。適當之羥基烷基酯如C1-C12羥基烷基-,較佳為C2-C8-羥基烷基單-或二酯。適當之環烷基酯如C5-C12-環烷基-,較佳為C6-C12-環烷基單-或二酯。適當之烷基環烷基酯如C6-C12-烷基環烷基-,較佳為C7-C10-烷基環烷基單-或二酯。適當之芳基酯如C6-C14-芳基,較佳為C6-C10-芳基單-或二酯。
α,β-乙烯基不飽和二羧酸單酯單體之適當實例包括●馬來酸單烷基酯,較佳為馬來酸單甲酯、馬來酸單乙酯、馬來酸單丙酯、及馬來酸單丁酯;●馬來酸單環烷基酯,較佳為馬來酸單環戊酯、馬來酸單環己酯、及馬來酸單環庚酯;●馬來酸單烷基環烷基酯,較佳為馬來酸單甲基環戊酯、及馬來酸單乙基環戊酯;●馬來酸單芳基酯,較佳為馬來酸單苯基酯;●馬來酸單苯甲酯,較佳為馬來酸單苯甲酯;●富馬酸單烷基酯,較佳為富馬酸單甲酯、富馬酸單乙酯、富馬酸單丙酯、及富馬酸單丁酯;
●富馬酸單環烷基酯,較佳為富馬酸單環戊酯、富馬酸單環己酯、及富馬酸單環庚酯;●富馬酸單烷基環烷基酯,較佳為富馬酸單甲基環戊酯及富馬酸單乙基環己酯;●富馬酸單芳基酯,較佳為富馬酸單苯基酯;●富馬酸單苯甲酯,較佳為富馬酸單苯甲酯;●檸康酸單烷基酯,較佳為檸康酸單甲酯、檸康酸單乙酯、檸康酸單丙酯、及檸康酸單正丁酯;●檸康酸單環烷基酯,較佳為檸康酸單環戊酯、檸康酸單環己酯、及檸康酸單環庚酯;●檸康酸單烷基環烷基酯,較佳為檸康酸單甲基環戊酯、及檸康酸單乙基環己酯;●檸康酸單芳基酯,較佳為檸康酸單苯基酯;●檸康酸單苯甲酯,較佳為檸康酸單苯甲酯;●衣康酸單烷基酯,較佳為衣康酸單甲酯、衣康酸單乙酯、衣康酸單丙酯、及衣康酸單正丁酯;●衣康酸單環烷基酯,較佳為衣康酸單環戊酯、衣康酸單環己酯、及衣康酸單環庚酯;●衣康酸單烷基環烷基酯,較佳為衣康酸單甲基環戊酯、及衣康酸單乙基環己酯;●衣康酸單芳基酯,較佳為衣康酸單苯基酯;●衣康酸單苯甲酯,較佳為衣康酸單苯甲酯。
就α,β-乙烯基不飽和二羧酸二酯單體而言,可使用以上述單酯單體為基礎之類似二酯,然而,其中該二經由氧原子連結
至C=O基之有機基團,可為相同或相異。
進一步可使用三元單體乙烯基芳族單體,如苯乙烯、α-甲基苯乙烯與乙烯基吡啶,以及非共軛二烯,如4-氰基環己烯與4-乙烯基環己烯,以及炔如1-或2-丁炔。
特別較佳之三單體或其各自之二或三酯,係衍生自下式:
其中R1為氫或甲基,以及R2、R3、R4、R5係相同或相異,且可代表H、C1-C12烷基、環烷
基、烷氧基烷基、羥基烷基、環氧基烷基、芳基、雜芳基。
於本發明之一具體實施例,該橡膠為NBR,較佳具衍生自至少一α,β-不飽和腈,更佳為丙烯腈之重複單元、至少一共軛二烯、更佳為丁二烯,以及無、一或多其他共聚化單體,更佳為無或一共聚化單體,選自丙烯酸與甲基丙烯酸;或SBR。
NBR中共軛二烯與α,β-不飽和腈之比例可於廣範圍中變化。共軛二烯之比例或共軛二烯之總和範圍通常為20至95重量%,較佳範圍為40至90重量%,更佳為50至85重量%,以總聚合物為基礎。α,β-不飽和腈之比例或α,β-不飽和腈之總和通常為5至80重量%,較佳為10至60,更佳為15至50重量%,以總聚合物為基礎。每一案例之單體比例,可加至100重量%。額外單體之存在量可為0至40重量%,較佳為0.1至40重量%,特別偏好1至30重量%,以總聚合物為基礎。在此案例中,共軛二烯或二烯及/或α,β-不飽和腈或腈之對應比例,係以額外單體之比例取代,其中每一案例之所有單體比例可加至100重量%。
藉上述單體之聚合作用而製備的腈橡膠係本領域技術人員習知,並完整描述於文獻。用於本發明目的之腈橡膠亦為商業上可購,如Lanxess Deutschland GmbH之Perbunan®與Krynac®等級產品範圍之產品。
用於決定腈橡膠中丙烯腈含量之氮含量(「CAN含量」),係以Kjeldahl法測定,其係依據DIN 53 625。由於極性共單體之含量,該腈橡膠通常於20℃下可溶於甲基乙酮,其含量>85重量%。
該腈橡膠具慕尼值(ML(1+4@100℃))10至150,較佳
為20至140,慕尼單元,特別較佳為25至120慕尼單元。此為下列解釋之式(I)中之MV1。
腈橡膠之玻璃轉換溫度範圍為-80℃至+20℃,較佳為-70℃至+10℃,最佳為-60℃至+5℃。
較佳之本發明腈橡膠包含丙烯腈重複單元、1,3-丁二烯,以及無、一或多共聚化單體。較佳之腈橡膠包含丙烯腈重複單元、1,3-丁二烯,以及一或多α,β-不飽和單羧酸或二羧酸、其酯類或醯胺類,尤其是α,β-不飽和羧酸之烷基酯重複單元,特別偏好甲基(甲基)丙烯酸酯、乙基(甲基)丙烯酸酯、丙基(甲基)丙烯酸酯、正丁基(甲基)丙烯酸酯、三級丁基(甲基)丙烯酸酯、己基(甲基)丙烯酸酯、2-乙基己基(甲基)丙烯酸酯、辛基(甲基)丙烯酸酯、月桂基(甲基)丙烯酸酯或富馬酸。
SBR:
SBR代表苯乙烯-丁二烯共聚物,包括其羧基化衍生物。因此,SBR包含衍生自苯乙烯與丁二烯之重複單元。苯乙烯含量典型上範圍為0至100重量%,較佳為10至60重量%。SBR可以兩種不同方法製備,即乳化聚合作用(「E-SBR」)或溶劑聚合作用(「S-SBR」)。乳化聚合作用為一種自由基聚合作用,而溶液聚合作用為陰離子聚合作用。SBR(有時縮寫為XSBR)之羧基化衍生物可由含有不飽和單體之至少一羧基,與丁二烯及苯乙烯共聚化,或將苯乙烯-丁二烯共聚物與至少一羧基單體接枝,該羧基如丙烯酸、甲基丙烯酸、丙烯醯胺、甲基丙烯醯胺、正甲氧基甲基甲基丙烯醯胺、正乙醯氧基甲基甲基丙烯醯胺、丙烯腈、二甲基丙烯醯胺、羥基乙
基丙烯酸酯、羥基丙基丙烯酸酯、羥基丁基丙烯酸酯、羥基乙基甲基丙烯酸酯、羥基丙基甲基丙烯酸酯、羥基丁基甲基丙烯酸酯、乙二醇二甲基丙烯酸酯、丁二醇二甲基丙烯酸酯、三羥甲丙烷三甲基丙烯酸酯、或新戊四醇四甲基丙烯酸酯。此含有單體之共聚化/接枝羧基可於0.1至25重量%之範圍內變化,其係以總聚合物為基礎。
於具體實施例1之一具體實施例,本發明提供一種安定化橡膠,較佳為腈橡膠,包含衍生自至少一α,β-不飽和腈之重複單元、至少一共軛二烯、及無、一或多其他共聚化單體、或苯乙烯-丁二烯共聚物,其進一步包含:(i)至少一,較佳為一式(I)化合物(ii)至少一,較佳為一式(II)化合物
其中R1為氫;直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代C1-C30烷基,更佳為直鏈或支鏈C12-C24烷基,最佳為直鏈C14-C18烷基;飽和或一或多次不飽和C3-C10碳環基,較佳為C3-C6環烷基;或C3-C10雜環基,較佳為C3-C6雜環基;C6-C24芳基,較佳為C6-C12芳基;C5-C23雜芳基,較佳為C5-C11雜芳基;C7-C30芳基烷基,較佳為C7-C25芳基烷基;C6-C29雜芳基烷基,較佳為C6-C25雜芳基烷基;聚氧基伸烷基醚,較佳為聚氧基乙烯醚、或聚氧基丙烯醚、或聚氧基乙烯-氧基丙烯醚;R2係相同或相異,且為直鏈或支鏈C1-C4烷基或C6環烷基;以及(iii)至少一,較佳為一式(III)化合物
其中
R3為直鏈或支鏈C1-C14烷基,較佳為直鏈或支鏈C1-C10烷基;以及R4為氫;直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代C1-C30烷基;飽和或一或多次不飽和C3-C10碳環基或C3-C10雜環基;C6-C24芳基;C5-C23雜芳基、C7-C30芳基烷基、C6-C29雜芳基烷基、C1-C24烷氧基、C6-C24芳基氧基、C5-C23雜芳基氧基、C1-C24烷基硫基、或C6-C24芳基硫基,較佳為直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代C1-C25烷基,更佳為直鏈或支鏈、飽和或一或多次不飽和C1-C20烷基,其中該烷基為未經取代或經一或多個取代基取代,該取代基係選自於由胺基、醯亞胺基、烷氧基、芳基氧基、硫基、烷基硫基、芳基硫基、羰基、羧基、氧基羰基、氧代、環氧基、或磺醯氧基組成之群組。
於具體實施例2之一具體實施例,本發明提供一種安定化橡膠,較佳為腈橡膠,包含衍生自至少一α,β-不飽和腈之重複單元,更佳為丙烯腈、至少一共軛二烯,更佳為1,3-丁二烯,以及無、一或多其他共聚化單體,或苯乙烯-丁二烯共聚物,該安定化橡膠更包含(i)至少一,較佳為一式(I)化合物
其中
n為1至10之範圍;(ii)至少一,較佳為一式(II)化合物
其中R1為氫;直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代C1-C30烷基,更佳為直鏈或支鏈C12-C24烷基,最佳為直鏈C14-C18烷基;飽和或一或多次不飽和C3-C10碳環基,較佳為C3-C6環烷基;或C3-C10雜環基,較佳為C3-C6雜環基;C6-C24芳基,較佳為C6-C12芳基;C5-C23雜芳基,較佳為C5-C11雜芳基;C7-C30芳基烷基,較佳為C7-C25芳基烷基;C6-C29雜芳基烷基,較佳為C6-C25雜芳基烷基;聚氧基伸烷基醚,較佳為聚氧基乙烯醚、或聚氧基丙烯醚、或聚氧基乙烯-氧基丙烯醚R2係相同或相異,較佳為相同,且為直鏈或支鏈C1-C4烷基,較佳為甲基、乙基、正丙基、異丙基、正丁基、異丁基、三級丁基、或C6環烷基;以及(iii)至少一,較佳為一式(III)化合物
其中R3為直鏈或支鏈C1-C14烷基,較佳為直鏈或支鏈C1-C10烷基,以及R4係相同或相異,較佳為相同,且為氫;直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代C1-C30烷基;飽和或一或多次不飽和C3-C10碳環基或C3-C10雜環基;C6-C24芳基;C5-C23雜芳基、C7-C30芳基烷基、C6-C29雜芳基烷基、C1-C24烷氧基、C6-C24芳基氧基、C5-C23雜芳基氧基、C1-C24烷基硫基、或C6-C24芳基硫基,較佳為直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代C1-C25烷基,更佳為直鏈或支鏈、飽和或一或多次不飽和C1-C20烷基,其中該烷基為未經取代或經一或多個取代基取代,該取代基係選自於由胺基、醯亞胺基、烷氧基、芳基氧基、硫基、烷基硫基、芳基硫基、羰基、羧基、氧基羰基、氧代、環氧基、或磺醯氧基組成之群組。
於本發明具體實施例2之另一具體實施例,本發明提供一種安定化橡膠,較佳為腈橡膠,包含衍生自至少一α,β-不飽和腈之重複單元,更佳為丙烯腈、至少一共軛二烯,更佳為1,3-丁二烯,以及無、一或多其他共聚化單體,或苯乙烯-丁二烯共聚物,該安定化橡膠更包含(i)至少一,較佳為一式(I)化合物(ii)至少一,較佳為一式(II)化合物
其中R1為直鏈或支鏈C15-C18烷基;R2係相同,且為直鏈或支鏈C1-C4烷基,較佳為甲基、乙基、正丙基、
異丙基、正丁基、異丁基、三級丁基、或C6環烷基;以及(iii)至少一,較佳為一式(III)化合物
其中R3為直鏈或支鏈C1-C4烷基;以及R4係相同,且為直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代C6-C14烷基。
於本發明之一具體實施例,該式(I)化合物中之碳原子,不論是在苯環,或連結至苯環之取代基,或衍生自環戊二烯單體之重複單元,可經一或多個取代基取代,其選自於由直鏈或支鏈、飽和或一或多次不飽和、未取代或經取代C1-C30烷基;飽和或一或多次不飽和C3-C10碳環基或C3-C10雜環基;C6-C24芳基;C5-C23雜芳基、C7-C30芳基烷基、C6-C29雜芳基烷基、C1-C24烷氧基、C6-C24芳基氧基、C5-C23雜芳基氧基、C1-C30烷氧基羰基、F、Cl、Br、I、羥基、羥基-亞胺基、胺甲醯基、磷醯基、膦醯基、烷基硫基、芳基硫基、磺醯基、硫基羧基、亞磺醯基、磺酸基、亞磺酸基、次磺酸基、磺酸、胺磺醯基、矽基、矽基氧基、腈、羰基、羧基、氧基羰基、氧基磺基、氧代、硫基、硼酸鹽、硒酸鹽、環氧基、氰酸鹽、硫基氰酸鹽、異氰酸鹽、硫基異氰酸鹽、及異腈組成之群組。
在本發明之一具體實施例中,該安定化橡膠包含式(I)化合物、式(II)化合物、及式(III)化合物。在另一實施例中,該二或多個化合物可選自於群組(i)、(ii)、及(iii)之一或多者,並可存在於安定化橡膠中。
落於式(I)-(III)定義中,可用於安定橡膠之三組分不同化合物,為商業上可購得或可依據技術上已知之流程製備。
該安定化橡膠中三組分之實例為:
- 關於組分(i):組分(i)代表聚(二環戊二烯-共-對甲苯酚),可得自Wingstay® L(如取自Omnova)或Ralox® LC(如取自Raschig),其具如上述與CAS no.68610-51-5之式(I)。
- 關於組分(ii):組分(ii)屬於空間上位阻之酚群組,實例為Irganox® 1076(得自BASF S.E.,CAS no.2082-79-3),其具式(II),其中R1為直鏈C18-烷基,且二R2為第三丁基;
- 關於組分(iii):組分(iii)屬於烷基硫基甲基酚抗氧化劑群組,實例為Irganox® 1520(得自BASF S.E.,CAS no.110553-27-0),其具式(III),其中二R4為正辛基,且R3為甲基。
若考慮助益,可加入抗氧化劑或抗老化化合物至橡膠中,以進一步穩定。此類其他抗氧化劑可包括烷基化單酚、氫醌及烷基化氫醌、生育酚、羥基化硫基二苯醚、烷二基雙酚;含O、N或S之苄基化合物、羥基苄基化丙二酸酯、芳香羥基苄基化合物、三化合物、苄基膦酸酯、醯基胺基酚、β-(5-三級丁基-4-羥基-3-甲基苯基)丙酸、及一元或多元醇之酯類;β-(3,5-二環己基-4-羥基苯基)丙酸與一元或多元醇之酯類;(3,5-二-三級丁基-4-羥基苯基)乙酸與一元或多元醇之酯類;β-3,5-二-三級丁基-4-羥基苯基)丙酸之醯胺、抗壞血酸(維生素C),以及胺類抗氧化劑。
於另一具體實施例,該安定化橡膠可額外包含(iv)至少一亞磷酸鹽抗氧化劑。
於一較佳具體實施例,該安定化橡膠額外包含亞磷酸鹽抗氧化劑,選自於由三(壬基苯基)亞磷酸鹽(亦縮寫為TNPP)、三(2,4-二-三級丁基苯基)亞磷酸鹽、其他烷基芳基亞磷酸鹽,及其混
合物組成之群組。於另一實施例,可使用商品名為Weston 705(Addivant USA LLC)之亞磷酸鹽。
於另一但等效之較佳具體實施例,本發明安定化橡膠之特徵為該安定化橡膠不含任何化合物(i)、(ii)、及(iii)以外之其他抗氧化劑。
於另一但等效之較佳具體實施例,本發明安定化橡膠之特徵為該安定化橡膠不含任何化合物(i)、(ii)、(iii)及亞磷酸鹽抗氧化劑以外之其他抗氧化劑。
安定劑組分之含量及比例:
典型而言,該三安定劑組分(i)、(ii)、及(iii)之總量範圍為0.01至10.0重量%,較佳為0.03至7.5重量%,更佳為0.05至5.0重量%,以100重量份之橡膠為基礎,較佳為腈橡膠或苯乙烯丁二烯橡膠。
該至少三安定劑組分(i)、(ii)、及(iii)之比例選擇可為廣範圍。較佳之組分(i):組分(ii):組分(iii)之重量比例範圍為(0.1-10):1:(0.1-10),較佳為(0.5-2):1:(0.5-2),更佳為(1-2):1:(1-2)。
較佳之安定劑組分(i)、(ii)、及(iii)之比例可為1:1:1或2:1:2。此應包括每一組分之精確比例加減10%之偏差。
若使用除了式(I)-(III)三組分以外之其他安定劑以安定橡膠,此類其他安定劑之用量至多5重量%,較佳為至多3.75重量%,更佳為至多2.5重量%,以100重量份之橡膠為基礎,較佳為腈橡膠或苯乙烯丁二烯橡膠。然而,需注意的是,所有安定劑之總量不
應過高。因此,若使用額外之不同安定劑,本領域之技術人員應可輕易決定是否須合理降低式(I)-(III)安定劑之量。
安定化橡膠之優點:
本發明之安定化橡膠,尤其是安定化腈橡膠或苯乙烯丁二烯 橡膠,令人驚訝地顯示出絕佳的保存安定性與色安定性,同時具有良好之加工特性,以及不變之良好機械與動力學特性。
就本發明目的而言,若慕尼黏度在一段長時間後維持盡量穩定,便可提供橡膠保存安定性,尤其是在相對高之溫度下亦如此。
保存安定性通常係以未硫化橡膠,於相對高溫度下儲存一段經定義時間(亦稱之為熱空氣儲存)而測定,並測定於高溫下在此儲存之前或之後間之慕尼黏度差異。由於橡膠之慕尼黏度通常會在熱空氣儲存期間增加,因此保存安定性之特徵為儲存後之慕尼黏度減去儲存前之慕尼黏度。此顯示於後述之安定化腈橡膠實例中,然而,亦可以類似方式轉移至其他橡膠類型。
有關腈橡膠之短期保存安定性「SS(ST)」如下式定義,單位為%
其中MV1為腈橡膠保存前之慕尼黏度,以及MV2為腈橡膠於100℃下保存48小時後之慕尼黏度。
同樣地,長期保存安定性「SS(LT)」如下式定義,單位為%
其中MV1為腈橡膠保存前之慕尼黏度,以及MV3為腈橡膠於70℃下保存7天後之慕尼黏度。
每一案例之慕尼黏度(ML1+4@100℃)係於100℃測定,其係以剪切圓盤式黏度計,依據DIN 53523/3或ASTM D 1646測定。不論於100℃下保存48小時,或是於70℃下保存7天,二者皆於對流烘乾箱中進行,其中氧氣含量與正常空氣一致。
一(1)慕尼單位之慕尼黏度(ML1+4@100℃)改變,可視為巧合效應或由於測量誤差所造成。
若橡膠不僅於短期老化方面顯示出慕尼黏度小量變化,同時於長期老化方面亦如此,則此橡膠視為具足夠保存安定性,以老化指數「AI」計算,如下式,單位為% AI=[SS(ST)+SS(LT)]
若該腈橡膠經由相同凝固法凝固(即使用相同之凝固鹽類或酸),並含有相同單體之重複單元,則由腈橡膠得到之老化指數AI絕對值可直接相互比較。
當比較經由不同凝固作用凝固(即使用相同之凝固鹽類或酸),或不含相同單體之重複單元之腈橡膠之老化指數AI時,必須將老化指數乘以校正因子F,以得到經校正之老化指數AI
(corr.)。
該經校正之老化指數AI(corr.)可依據下式決定AI(corr.)=F‧AI
其中F為校正因子,其值為1,若包含至少一共軛二烯與至少一α,β不飽和腈之重複單元的腈橡膠係以鈣鹽或酸凝結,或值為0.5,若包含至少一共軛二烯與至少一α,β不飽和腈之重複單元的腈橡膠係以鈣鹽以外之另一鹽類凝結,尤其是銨鹽,或值為0.04,若腈橡膠包含至少一共軛二烯、至少一α,β不飽和腈與至少一三單體,較佳為不飽和羧酸之重複單元。
基於上式,若經校正之老化指數AI(corr.)最大值為14%,則腈橡膠視為具足夠保存安定性。
高保存安定性具有正面效果,即使是在腈橡膠乾燥期間,係因某些橡膠於此期間發生未預期之老化。高保存安定性有助於預定目標慕尼黏度之設定。其結果為,規格外之腈橡膠量減少。此外,高保存安定性可使在長期保存或運送期間慕尼黏度改變之情況降低。本發明之橡膠適用於重複製造硫化混合物。因此由硫化所得之模型亦具機械與物理特性之再現性。
安定化橡膠之製備:
本發明進一步係有關一種製造安定化橡膠之方法,係
將組分(i)、(ii)、(iii)、及任意地(iv)接觸於橡膠。
此種加入一般可由多種方式達成:(1)於橡膠製備期間,包括橡膠之聚合及後處理,後者包含凝結與分離,(2)於橡膠製備後之一或多個其他化學轉換步驟,如複分解反應(metathesis reaction)、氫化反應、或類聚合物類似物反應如接枝,及/或(3)於製備以腈橡膠為基底之硫化橡膠混合物期間,或該腈橡膠於交聯前進行一或多個進一步之化學轉換之後。
前述任一步驟之組分添加可以不同方法實行:
每一組分(i)、(ii)、及(iii)(以及任意地(iv))可單獨加入,或者,可製備並加入主要三組分之所有不同種類混合物。一般而言,該三組分,不論是單獨或以任何組合形式加入,皆可用作分散劑或乳化劑。
每一組分(i)、(ii)、及(iii)(以及任意地(iv))可單獨加入,或者,可製備並加入主要三組分之所有不同種類混合物。一般而言,該三組分,不論是單獨或以任何組合形式加入,皆可用作分散劑或乳化劑。
若考慮助益性,乳化劑可用於製備分散劑或乳化劑。適當之乳化劑為如具熱安定性至溫度範圍200-350℃。適當之乳化劑為十二烷基苯磺酸鈉或月桂基硫酸鈉,其較佳用量為5至25重量%之含安定劑之乳化劑,取決於界面活性劑之特定性質。適當之含量可由本領域技術人員輕易決定。
一般方法描述於EP 0 488 550A1(請見第7頁之步驟2A,
第36至49行),以及EP-A-0 439 427,可以類似方式製備分散劑或乳化劑。
於另一具體實施例,包含所有三組分(i)、(ii)、及(iii)之安定化系統,係如前述製備成水性分散劑,並加至橡膠。
於產業實施時,典型而言希望使用安定化系統之水性分散劑,包含所有三組分(i)、(ii)、及(iii),以使相容性與加入效率達最大。分散劑可定義為懸浮於水中之有機材料之非均質混合物。為提供彼等,可能需要其他組分並包含以下之一或多者:水、界面活性劑、增稠劑、防腐劑、及佐劑如消泡劑。
界面活性劑可為陰離子性、非離子性、或陽離子性。較佳之界面活性劑可包含脂肪酸如油酸與鹼如氫氧化鉀水溶液之混合物。
較佳之增稠劑可為水膠體,較佳為黃原膠。此為較佳,以確保貯存和運輸過程中的長期安定性。
此外,亦可使用此混合物之水溶液或有機溶劑。
可用於本發明之安定化系統之水性分散劑,可以加熱並混合熔融組分而製造。可加入界面活性劑。適當之界面活性劑可包含長鏈脂肪酸如油酸與鹼如氫氧化鉀水溶液之混合物。所得混合物可與熱水及水膠攪拌,如黃原膠,以形成懸浮液,之後冷卻。任何其他組分,如殺菌劑,可在包裝與儲存或分配之前加入。
若要進一步使用不同的安定劑,其一般亦可加至包含前述三組分(i)、(ii)、及(iii)之安定化系統中。
除了該三基本組分(i)、(ii)、及(iii),安定劑系統可更包含輔助組分,其包含至少一界面活性劑,及/或一或多個聚合物添
加劑,其不同於組分(i)、(ii)、及(iii)。
於一較佳具體實施例,本發明提供一種製備安定化腈橡膠或安定化部分或全部氫化腈橡膠之方法,其中腈橡膠或安定化部分或全部氫化腈橡膠包含衍生自至少一α,β-不飽和腈、至少一共軛二烯,以及無、一或多個其他共聚化單體,其係藉由1)進行至少一α,β-不飽和腈、至少一共軛二烯,以及無、一或多個其他共聚化單體之水性介質之乳化聚合,產生腈橡膠水性介質分散劑(稱之為「乳膠」),2)將腈橡膠水性分散劑進行凝結作用,並分離出腈橡膠,以及3)若欲安定化部分或全部氫化之腈橡膠,應部分或完全氫化步驟2)之腈橡膠。
特徵為該包含組分(i)、(ii)、及(iii)之安定化系統,可於步驟1)、2)及/或3)加入腈橡膠或安定化部分或全部氫化之腈橡膠。
如安定化橡膠之一般製備方法所述,組分(i)、(ii)、及(iii)之每一者可單獨加入,或者,可製備並加入主要三組分之所有不同種類混合物,並於步驟1)、2)及/或3)期間或之後加入。較佳為安定化系統包含所有三組分(i)、(ii)、及(iii),且更佳為以水性分散劑存在,其係預先製備並加入。
本發明進一步係有關藉任何前述流程獲得之安定化橡膠,特別是藉接觸橡膠於三組分(i)、(ii)、及(iii)而獲得,該組分係以水性分散劑存在。
步驟1:腈橡膠之乳化聚合作用
腈橡膠之乳化聚合作用為習知,且典型而言以陰離子
乳化劑或不帶電乳化劑之水溶性鹽類作為乳化劑。偏好為使用陰離子乳化劑。
作為陰離子乳化劑,可使用改質之樹脂酸,其係取自含松脂酸、新松脂酸、長葉松酸、左旋海松酸之樹脂酸混合物之二聚合作用、歧化作用、氫化、及修飾。具體較佳之經修飾樹脂酸為經歧化之樹脂酸(Ullmann’s Encyclopedia of Industrial Chemistry,6th Edition,Volume 31,pp.345-355)。
亦可以C6-C22脂肪酸作為陰離子乳化劑。其可完全飽和或分子具一或多個雙鍵。脂肪酸之實例為己酸、月桂酸、肉荳蔻酸、棕櫚酸、硬脂酸、油酸、亞油酸、亞麻酸。羧酸常基於特殊來源油類或脂肪,如蓖麻油、棉籽油、花生油、亞麻籽油、椰子油、棕櫚仁油、橄欖油、菜籽油、大豆油、魚油、及牛肉距骨(beef talo)等(Ullmann’s Encyclopedia of Industrial Chemistry,6th Edition,Volume 13,pp.75-108)。較佳之羧酸係源自椰子油脂肪酸及源自牛肉距骨,且係部分或完全氫化。
此類基於經修飾之樹脂酸或脂肪酸的羧酸係作為水溶性鋰鹽、鈉鹽、鉀鹽、及銨鹽。較佳為鈉鹽及鉀鹽。
進一步之陰離子乳化劑為磺酸鹽、硫酸鹽、及磷酸鹽,其係結合於有機自由基。可能的有機自由基為C6至C25脂肪自由基、芳族自由基、烷基鏈具3至12個碳原子之烷化芳烴、融合芳烴、及亞甲基橋聯芳烴,其中亞甲基橋聯及融合芳烴係能額外烷化。典型而言,硫酸鹽、磺酸鹽、及磷酸鹽係作為鋰鹽、鈉鹽、鉀鹽、或銨鹽。較佳為鈉鹽、鉀鹽、及銨鹽。
此類磺酸鹽、硫酸鹽、及磷酸鹽之實例為月桂基硫酸
鈉、烷基磺酸鈉、烷基芳基磺酸鈉、亞甲基橋聯之芳基磺酸鈉鹽、烷化萘磺酸鈉鹽、及亞甲基橋聯之萘磺酸鈉鹽,其亦可經寡聚合化,其中寡聚合程度係為2至10之範圍。烷化萘磺酸及亞甲基橋聯(與任意烷化)之萘磺酸係通常以異構物之混合物存在,其分子亦可含有超過一個磺酸基團(2至3個磺酸基團)。具體偏好為月桂基硫酸鈉、具12至18個碳原子之烷基磺酸鈉混合物、烷基芳基磺酸鈉、二異丁烯萘磺酸鈉、亞甲基橋聯之聚萘磺酸鹽混合物、及亞甲基橋聯之芳基磺酸鹽混合物。
不帶電乳化劑係衍生自化合物之氧化乙烯與氧化丙烯加成產物,其具足夠之酸性氫。該些包括,如酚、烷基化酚、及烷基化胺。環氧化物聚合作用之平均程度範圍為2至20。不帶電乳化劑之實例為乙氧基化壬酚,其具有8、10、及12個氧化乙烯單元。不帶電乳化劑通常不單獨使用,而是與陰離子性乳化劑結合。
偏好為歧化松脂酸之鈉鹽與鉀鹽,以及部分氫化之距骨脂肪酸,及其混合物、月桂基硫酸鈉、烷基磺酸鈉、烷基苯磺酸鈉、及烷基化與甲烯橋聯萘磺酸。
乳化劑之用量為每100重量份單體混合物0.2至15重量份,較佳為0.5至12.5重量份,特別較佳為1.0至10重量份。
乳化聚合作用之啟動一般以聚合作用起始劑進行,其分解成自由基。此類起始劑包括含有-O-O-單元(過氧化合物)或-N=N-單元(偶氮化合物)之化合物。
過氧化合物包括過氧化氫、硫酸過氧化物、磷酸過氧化物、氫過氧化物、過酸、過酸酯、過酸酐,以及具有二有機自由基之過氧化物。過氧二硫酸與過氧二磷酸之鹽類可為鈉、鉀與銨鹽。
適當之氫過氧化物如三級丁基氫過氧化物、異丙苯氫過氧化物、蒎烷氫過氧化物、及對薄荷烷氫過氧化物。適當之具有二有機自由基之過氧化物為二苯甲醯過氧化物、雙-2,4-二氯苯甲醯過氧化物、二-三級丁基過氧化物、二異丙苯基過氧化物、三級丁基過苯甲酸酯、三級丁基過乙酸酯等。
適當之偶氮化合物為偶氮雙異丁腈、偶氮雙戊腈、及偶氮雙環己腈。
過氧化氫、氫過氧化物、過酸、過酸酯、過氧二硫酸鹽、及過氧二磷酸鹽亦可與還原劑結合使用。適當之還原劑為次磺酸鹽、亞磺酸鹽、次硫酸鹽、二硫亞磺酸鹽、亞硫酸鹽、焦亞硫酸鹽、亞硫酸氫鹽、糖、尿素、硫基脲、黃原酸鹽、硫基黃原酸鹽、肼鹽、胺與胺衍生物如苯胺、二甲基苯胺、單乙醇胺、二乙醇胺、或三乙醇胺。
由氧化劑與還原劑組成之起始劑系統亦稱之為氧化還原系統。當使用氧化還原系統時,過渡金屬如鐵、鈷、及鎳之鹽類亦常被用於與適當之錯合劑如乙二胺四醋酸鈉、腈三乙酸鈉、及磷酸三鈉或磷酸四鉀結合。
較佳之氧化還原系統為:1)過氧硫酸鉀與三乙醇胺之結合,2)過氧磷酸銨與焦亞硫酸鈉(Na2S2O5)及鐵之結合,3)對-甲烷氫過氧化物/甲醛次硫酸氫鈉與Fe(II)硫酸鹽(FeSO4*7 H2O)、乙二胺醋酸鈉與三磷酸鈉之結合,4)茴香烴氫過氧化物/甲醛次硫酸氫鈉與Fe(II)硫酸鹽(FeSO4*7 H2O)、乙二胺醋酸鈉與二磷酸四鉀之結合。
氧化劑之量為每100份單體重量0.001至1重量份。還原劑之莫耳量範圍為50%至500%,以所使用之氧化劑莫耳量為基準。
錯合劑之莫耳量係以所使用之過渡金屬量為基準,通常與其等莫耳數。
欲進行聚合作用,起始劑系統之所有或各組分係於聚合作用之初或聚合作用期間導入。較佳於聚合作用期間,以部分方式加入起始劑系統之所有或各組分。依序添加使反應速率可控。
一般而言,聚合反應係於分子量調節劑存在下進行,其通常為具9至16個碳原子之烷基硫基。該烷基硫基或烷基硫基異構混合物為市售可得,或可依據技術上習知之流程製備。
聚合作用時間範圍為5小時至15小時,基本上取決於單體混合物之丙烯腈含量及聚合作用溫度。
聚合作用溫度範圍為0至50℃,較佳範圍為5至55℃,更佳範圍為8至40℃。
待轉換率達50至99%,較佳為65至95%後,聚合作用便停止。為此目的,將終止劑加入反應混合物。適當之終止劑如,二甲基二硫基胺甲酸酯、亞硝酸鈉、及二甲基二硫基胺甲酸酯與亞硝酸鈉之混合物、肼和羥基胺及其衍生之鹽類,如肼硫酸鹽與羥基硫酸銨、二乙基羥基胺、二異丙基羥基胺、氫醌之水溶性鹽、二硫亞磺酸鈉、苯基-α萘胺、及芳香酚,如三-三級丁基兒茶酚或吩噻嗪。
用於乳化聚合作用之水量範圍為每100重量份單體混合物100至900重量份,較佳為120至500重量份,特佳為150至400重量份之水。
可將鹽類加入乳化聚合作用之水相中,以於聚合作用期間降低黏度、調整並緩衝酸鹼值。通常用於此目的之鹽類為單價金屬,形式為氫氧化鉀與氫氧化鈉、硫酸鈉、碳酸鈉、碳酸氫鈉、
氯化鋰、氯化鈉、及氯化鉀。偏好為氫氧化鉀與氫氧化鈉、碳酸氫鈉、氯化鋰、氯化鈉、及氯化鉀。該些電解質之含量範圍為每100重量份單體混合物0至1重量份,較佳為0至0.5重量份。於乳化聚合作用期間加入含氯鹽類是必須的,尤其是在含氯鹽類未用於後續凝結作用,或是凝結腈橡膠(本發明方法特徵(iv))之清洗。
聚合作用可以批次或以攪拌瓶串聯之連續方式進行。
欲達到聚合作用過程均一,僅有部分起始劑系統用於啟動聚合作用,其餘係於聚合作用期間進料。聚合作用通常以起始劑總量之10至80重量%,較佳為30-50重量%啟動。亦可於聚合作用開始後導入起始劑系統之各組分。
若需製造化學性質均一之腈橡膠,當組成物落於丁二烯/丙烯腈共沸比例之外時,可進一步導入丙烯腈或丁二烯。其他添加之較佳方式,係於NBR具丙烯腈含量10至34重量%,及丙烯腈含量40至50重量%之下進行(W.Hofmann,“nitrilkautschuk”,Berliner Union Stuttgart,S.58ff)。其他劑量係如DD 154 702指示,較佳為於電腦控制下進行,並基於電腦程式。
欲移除未反應之單體與揮發性組分,反應終止之乳膠進行蒸氣蒸餾。此時,溫度範圍為70℃至150℃,當溫度低於100℃時壓力下降。
於移除揮發性組分之前,乳膠可以乳化劑進行後安定化。於此目的,較佳為使用前述之乳化劑,其用量為每100重量份腈橡膠0.1至2.5重量%,較佳為0.5至2.0重量%。
步驟2:乳膠之凝結作用
具酸鹼值至少6,較佳為大於6之乳膠,係用於凝結作用。若適當,此酸鹼值係以加入鹼而達成,較佳為氨水或氫氧化鈉或氫氧化鉀。
凝結作用係以選自於由鋁鹽、鈣鹽、鎂鹽、鈉鹽、鉀鹽、鋰鹽所組成群組之至少一者進行。
作為該些鹽類之陰離子,通常使用單價或二價陰離子。偏好為鹵化物,尤佳為氯化物、硝酸鹽、硫酸鹽、碳酸氫鹽、碳酸鹽、甲酸鹽、及乙酸鹽。
適當之鹽類實例為氯化鈉、氯化鉀、氯化鈣、氯化鎂、硝酸鈉、硝酸鉀、硫酸鈉、硫酸鉀、碳酸氫鈉、碳酸氫鉀、碳酸鈉、碳酸鉀、硫酸鋁、鉀硫酸鋁(明礬鉀)、鈉硫酸鋁(明礬鈉)、醋酸鈉、醋酸鈣、及甲酸鈣。若水溶性鈣鹽用於乳膠凝結作用,較佳為氯化鈣。
鹽類之用量為0.05至10重量%,較佳為0.5至8重量%,更佳為1至5重量%,以腈橡膠分散劑之固體含量(即乳膠)為基準。
除了選自於上述群組之至少一鹽類之外,沈澱輔助物亦可用於凝結作用。可能的沈澱輔助物如水溶性聚合物。該些為非離子性、陰離子性、或陽離子性。
非離子性聚合性沈澱輔助物之實例為經修飾之纖維素,如羥基烷基纖維素或甲基纖維素修飾,以及具有足夠酸性氫之化合物之氧化乙烯加成產物與氧化丙烯加成產物。具酸性氫之化合物之實例為:脂肪酸、糖,如山梨糖醇、脂肪酸之單酸甘油酯與甘油二酯、酚、烷基化酚、及(烷基)酚-甲醛縮合物。具有足夠酸性氫
之化合物之氧化乙烯加成產物與氧化丙烯加成產物可具有隨機或嵌段結構。於該些產物中,偏好為其溶解度隨溫度增加而減少者。特徵雲狀溫度範圍為0至100℃,尤其是20至70℃之範圍。
陰離子性聚合性沈澱輔助物之實例為(甲基)丙烯酸、馬來酸、及馬來酸酐之同聚物與共聚物。較佳為聚丙烯酸之鈉鹽。
陽離子性聚合性沈澱輔助物通常以多胺或(甲基)丙烯醯胺之同聚物與共聚物為基礎。偏好為聚甲基丙烯醯胺與多胺,尤其是以環氧氯丙烷與二胺為基礎者。
聚合性沈澱輔助物之量為每100重量份腈橡膠0.01至5重量份,較佳為0.05至2.5重量份。
亦可使用其他沈澱輔助物。然而,即使無額外之沈澱輔助物,亦可立即完成該流程。
用於凝結作用之橡膠較佳為具有固體濃度範圍1%至40%,較佳為5%至35%,特別較佳為15至30重量%。
乳膠之凝結作用係於溫度範圍10至110℃,較佳為20至100℃,更佳為50至98℃下進行。乳膠之凝結作用可連續或批次進行,且較佳為連續進行。
於另一具體實施例,不含未轉換單體之乳膠可以酸鹼值6,較佳為4,更佳為2之酸處理,以產生聚合物沈澱。可使用所有可使酸鹼值達上述範圍之礦物酸及有機酸。較佳為使用礦物酸。之後,聚合物以習知流程自懸浮液中移出,可以批次或連續方式,較佳為連續方式進行。
經凝結腈橡膠之清洗、脫水、及乾燥
於凝結作用後,腈橡膠通常為碎屑形式。因此已凝結NBR之清洗亦稱為碎屑清洗。可使用去離子水(亦稱之為DW)或未去離子之水(亦稱之為BW)清洗此凝結碎屑。清洗係於溫度範圍15至90℃,較佳於溫度範圍20至80℃下進行。清洗用水之量為每100重量份之腈橡膠0.5至20重量份,較佳為1至10重量份,特別較佳為1至5重量份。
橡膠碎屑較佳為進行多次清洗,其中橡膠碎屑會在每個清洗階段間部分脫水。各清洗階段間碎屑之殘餘含水量範圍為5至50重量%,較佳為7至25重量%。清洗階段數目通常為1至7,較佳為1至3。清洗可以批次或連續式進行。偏好為使用多階段、連續式流程,使用逆流清洗為較佳,以節省水。待清洗完成後,使腈橡膠碎屑脫水將相當有幫助。於初期脫水階段進行之腈橡膠乾燥,係於流式床烘乾機或平板式烘乾機進行。乾燥期間之溫度範圍為80至150℃。偏好為依據溫度程式乾燥,其中溫度在乾燥流程末期下降。
步驟3:類腈橡膠複分解與氫化之進一步化學轉換
本發明腈橡膠亦可依據(i)複分解降解流程或(ii)複分解降解流程與後續氫化或(iii)僅有氫化反應而製備。此複分解降解流程與氫化反應二者皆為此技術領域者習知並描述於文獻。複分解如WO-A-02/100941以及WO-A-02/100905之描述,並可用於分子降解。
氫化係以均質或非均質氫化觸媒進行。亦可進行原位氫化,即於先前選擇性複分解降解進行之同一反應瓶中進行反應,
而不需分離出降解之腈橡膠。該氫化觸媒可簡單加至反應瓶中。
使用之觸媒通常以銠、釕、或鈦為基礎,但也可以使用鉑、銥、鈀、錸、釕、鋨、鈷、或銅,係金屬或較佳為金屬化合物形式(如US-A-3,700,637、DE-A-25 39 132、EP-A-0 134 023、DE-A-35 41 689、DE-A-35 40 918、EP-A-0 298 386、DE-A-35 29 252、DE-A-34 33 392、US-A-4,464,515、及US-A-4,503,196)。
用於均質相氫化反應之適當觸媒與溶劑描述於下,並描述於DE-A-25 39 132與EP-A-0 471 250。可達到選擇性氫化反應,例如於含銠或釕觸媒之存在下。可使用如下式觸媒(R1 mB)l M Xn,其中M為銠或釕,自由基R1為相同或相異,每一者為C1-C8-烷基、C4-C8-環烷基、C6-C15-芳基或C7-C15-芳烷基。B為磷、砷、硫、或亞碸基S=O,X為氫或陰離子,較佳為鹵素,特別較佳為氯或溴,l為2、3或4,m為2或3,以及n為1、2或3,較佳為1或3。較佳觸媒為式((C6H5)3P)4RhH之三(三苯基膦)氯化銠(I)、三(三苯基膦)氯化銠(III),及三(二甲基亞碸)氯化銠(III),及四(三苯基膦)氫化銠,及相對應之化合物,其中三苯基膦完全或部分被三環己基膦取代。觸媒可使用小量。含量範圍為0.01-1重量%,較佳範圍為0.03-0.5重量%,特別較佳範圍為0.1-0.3重量%,以聚合物重量為基礎。
常適合使用觸媒與共觸媒,其具有式R1 mB之配位基,其中R1、m、及B具有上述對於觸媒之定義。較佳地,m為3、B為磷、及自由基R1可為相同或相異。偏好為共觸媒具有三烷基、三環烷基、三芳基、三芳烷基、二芳基-單烷基、二芳基-單環烷基、二烷基-單芳基、二烷基-單環烷基、二環烷基-單芳基、或二環烷基-單芳基自
由基。
共觸媒之實例可參考如US-A-4,631,315。較佳之共觸媒為三苯基膦。共觸媒較佳之用量範圍為0.3-5重量%,較佳範圍為0.5-4重量%,以待氫化之腈橡膠重量為基準。此外,含銠觸媒對共觸媒之重量比較佳範圍為1:3至1:55,更佳範圍為1:5至1:45。以100重量份待氫化腈橡膠為基準,較佳為使用0.1至33重量份之共觸媒,較佳為0.5至20重量份,特別較佳為1至5重量份,特佳為大於2但小於5重量份之共觸媒。
氫化之實施可由本領域技術人員參考US-A-6,683,136而進行。通常係將溶劑如甲苯或單氯苯中之待氫化腈橡膠,於溫度範圍100至150℃、壓力範圍50至150巴下,與氫反應2至10小時而進行。
針對本發明之目的,氫化為起始腈橡膠中存在之雙鍵反應至至少50%,較佳為70-100%,特別較佳為80-100%之程度。
當使用非均質性觸媒時,該些通常為如碳、二氧化矽、碳酸鈣、或硫酸鋇支撐之鈀觸媒。
類似於本發明之腈橡膠,由本發明腈橡膠複分解及/或氫化後所得之任擇性氫化腈橡膠,可加入硫化混合物,並用於製造模型與塑型組件。此任意之氫化腈橡膠具慕尼黏度(ML(1+4@100℃))1至50,較佳為1至40慕尼單位。
本發明亦提供使用橡膠,較佳為本發明之腈橡膠,製造硫化混合物,其含有至少一橡膠,較佳為本發明之腈橡膠、至少一交聯劑、及任意地其他添加劑。
該些硫化混合物係藉由將至少一安定化橡膠,較佳為
本發明之腈橡膠、至少一交聯劑、及任意地其他添加劑混合。
作為交聯劑,可使用如過氧化物交聯劑,如雙(2,4-二氯苄基)過氧化物、二苯甲醯過氧化物、雙(4-氯苯甲醯基)過氧化物、1,1-雙(三級丁基過氧基)-3,3,5-三甲基環己烷、三級丁基過苯甲酸酯、2,2-雙(三級丁基過氧基)丁烯、4,4-二-三級丁基過氧基壬基戊酸酯、二異丙苯過氧化物、2,5-二甲基-2,5-二(三級丁基過氧基)己烷、三級丁基異丙苯過氧化物、1,3-雙(三級丁基過氧基異丙基)苯、二-三級丁基過氧化物、及2,5-二甲基-2,5-二(三級丁基過氧基)己-3-炔。
較佳為不僅使用該些過氧化物交聯劑,同時亦使用其他可增加交聯產率之添加劑:此類型之適當添加劑為如三烯丙基異氰脲酸酯、三烯丙基氰脲酸酯、三甲醇基丙烷三(甲基)丙烯酸酯、三烯丙基偏苯三酸酯、乙二醇二甲基丙烯酸酯、丁二醇二甲基丙烯酸酯、三甲醇基丙烷三甲基丙烯酸酯、二丙烯酸鋅、二甲基丙烯酸鋅、1,2-聚丁二烯、或N,N'-間伸苯基二順丁烯二醯亞胺。
交聯劑或交聯劑群之總量範圍為1至20phr,較佳範圍為1.5至15phr,特別較佳範圍為2至10phr,以腈橡膠為基準。
亦可以可溶性或不可溶性形式之硫元素、或硫供體作為交聯劑。
可能的硫供體如二嗎啉基二硫化物(DTDM)、2-嗎啉代二硫噻唑(MBSS)、己內醯胺二硫化物、二五伸甲基秋蘭姆四硫化物(DPTT)、及四甲基秋蘭姆二硫化物(TMTD)。
於本發明腈橡膠之硫化作用方面,亦可使用其他可增加交聯產率之添加劑。然而,原則上交聯亦可僅以硫或硫供體進行。
相反地,本發明腈橡膠之交聯亦可僅於上述添加劑存
在下進行,即不加入元素硫或硫供體。
可增加交聯產率之適當添加劑如,二硫基胺甲酸酯、秋蘭姆、噻唑、磺醯胺、黃原酸鹽、胍衍生物、己內醯胺、及硫脲衍生物。
就二硫基胺甲酸鹽而言,可使用如:二甲基二硫基胺甲酸銨、二乙基二硫基胺甲酸鈉(SDEC)、二丁基二硫基胺甲酸鈉(SDBC)、二甲基二硫基胺甲酸鋅(ZDMC)、二乙基二硫基胺甲酸鋅(ZDEC)、二丁基二硫基胺甲酸鋅(ZDBC)、乙基苯基二硫基胺甲酸鋅(ZEPC)、二苄基二硫基胺甲酸鋅(ZBEC)、五伸甲基二硫基胺甲酸鋅(Z5MC)、二乙基二硫基胺甲酸碲、二丁基二硫基胺甲酸鎳、二甲基二硫基胺甲酸鎳、及二異壬基二硫基胺甲酸鋅。
就秋蘭姆而言,可使用如:四甲基秋蘭姆二硫化物(TMTD)、四甲基秋蘭姆單硫化物(TMTD)、二甲基二苯基秋蘭姆二硫化物、四苄基秋蘭姆二硫化物、二五伸甲基秋蘭姆四硫化物、及四乙基秋蘭姆二硫化物(TETD)。
就噻唑而言,可使用如:2-巰基苯並噻唑(MBT)、二苯並噻唑二硫化物(MBTS)、鋅巰基-苯並噻唑(ZMBT)、及銅-2-巰基苯並噻唑。
就磺醯胺衍生物而言,可使用如:正環己基-2-苯並噻唑亞磺醯胺(CBS)、正-三級丁基-2-苯並噻唑亞磺醯胺(TBBS)、N,N’-二環己基-2-苯並噻唑亞磺醯胺(DCBS)、2-嗎啉硫基苯並噻唑(MBS)、N-氧基-二伸乙基胺基甲醯基-N-三級丁基亞磺醯胺、及氧基二伸乙基胺基甲醯基-N-氧基伸乙基亞磺醯胺。
就黃原酸鹽而言,可使用如:二丁基黃原酸鈉、異丙
基二丁基黃原酸鋅、及二丁基黃原酸鋅。
就胍衍生物而言,可使用如:二苯基胍(DPG)、二-o-甲苯胍(DOG)、及鄰甲苯基雙胍(OTBG)。
就二硫基磷酸鹽而言,可使用如:二烷基二硫基磷酸鋅(烷基自由基鏈長:C2至C16)、二烷基二硫基磷酸銅(烷基自由基鏈長:C2至C16)、及二硫基磷醯基聚硫化物。
就己內醯胺而言,可使用如二雙己內醯胺。
就硫基尿素衍生物而言,可使用如N,N’-二苯基硫基尿素(DPTU)、二乙基硫基尿素(DETU)、及伸乙基硫基尿素(ETU)。
其他適當之添加劑如:鋅二胺二異氰酸酯、六甲基四胺、1,3-雙(檸康基醯亞胺甲基)苯、及環二硫烷。
上述添加劑與交聯劑可單獨使用或以混合物使用。偏好為使用下列物質進行腈橡膠之交聯:硫、2巰基苯並噻唑、四甲基秋蘭姆二硫化物、四甲基秋蘭姆單硫化物、二苄基二硫基胺甲酸鋅、二五伸甲基秋蘭姆四硫化物、二烷基二硫基磷酸鋅、二硫化二嗎啉基、二乙基二硫基胺甲酸碲、二丁基二硫基胺甲酸鎳、二丁基二硫基胺甲酸鋅、二甲基二硫基胺甲酸鋅、及二硫基雙己內醯胺。
上述交聯劑與上述添加劑之用量為0.05至10phr,較佳為0.1至8phr,特別較佳為0.5至5phr(單一添加,每一者皆以活性物質為基準)。
就本發明之硫交聯而言,亦可使用除了上述交聯劑與上述添加劑外之其他無機或有機物質。此類其他物質之實例為:氧化鋅、碳酸鋅、氧化鉛、氧化鎂、飽和或不飽和有機脂肪酸與其鋅鹽、多元醇,胺基醇如三乙醇胺、及胺類如二丁基胺、二環己基胺、
環己基乙胺與聚醚胺。
此外,也可使用初始硫化抑制劑。該些包括環己基硫基鄰苯二甲醯亞胺(CTP)、N,N’-二甲基二亞硝基五甲四胺(DNPT)、鄰苯二甲酸酐(PTA)、及二苯基亞硝胺。偏好為環己基硫基鄰苯二甲酰亞胺(CTP)。
除了加入交聯劑或交聯劑群,本發明腈橡膠也可以與其它常用橡膠添加劑混合。
該些包括,例如,本領域技術人員所習知之典型物質,例如填充劑、填充劑活化劑、臭氧保護劑、老化抑制劑、抗氧化劑、加工助劑、延展油、塑化劑、強化材料、及脫模劑。
作為填充劑,可使用如炭黑、二氧化矽、硫酸鋇、二氧化鈦、氧化鋅、氧化鈣、碳酸鈣、氧化鎂、氧化鋁、氧化鐵,氫氧化鋁、氫氧化鎂、矽酸鋁、矽藻土、滑石、高嶺土、膨潤土、奈米碳管、特氟隆(後者較佳為粉末形式)、或矽酸鹽。
可能的填充劑活化劑特別為有機矽烷,如乙烯基三甲基氧基矽烷、乙烯基二甲氧基甲基矽烷、乙烯基三乙氧基矽烷、乙烯基三(2-甲氧基乙氧基)矽烷、N-環己基-3-胺基丙基三甲氧基矽烷、3-胺基丙基三甲氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、三甲基乙氧基矽烷、異辛基三甲氧基矽烷、異辛基三乙氧基矽烷、十六基三甲氧基矽烷、或(十八基)甲基二甲氧基矽烷。其他填充劑活化劑如界面活性物質如三乙醇胺與乙二醇,其具分子量74至10 000克/莫耳。填充劑活化劑之量通常為0至10phr,以100phr腈橡膠為基準。
作為老化抑制劑,可加入已描述於本申請書中者,其
係關於乳膠凝結至硫化混合物。該些用量常為約0至5phr,較佳為0.5至3phr,以100phr腈橡膠為基準。
可能的脫模劑如:飽和及部分不飽和脂肪酸,以及油酸及其衍生物(脂肪酸酯、脂肪酸鹽、脂肪醇、脂肪醯胺),較佳係以組分混合物使用,產物可施加於模具表面,如以低分子量矽化合物為基礎之產物、以氟聚合物為基礎之產物、及以酚醛樹枝為基礎之產物。
當作為混合物之構成物時,脫模劑之用量通常為約0至10phr,較佳為0.5至5phr,以100phr腈橡膠為基準。
由玻璃組成之強度載體(纖維)的強化,係根據US-A-4826721之揭示,亦可由簾線、織物、由脂肪族和芳香族聚醯胺組成之纖維(Nylon®,Aramid®)、聚酯、及天然纖維產品進行強化。
本發明進一步提供一種製造硫化橡膠之方法,以本發明之至少一腈橡膠為基礎,其特徵在於:上述硫化混合物係於成形過程中硫化,較佳為使用射出成型法。
因此,本發明同樣提供了可經由上述硫化過程獲得的特定形狀組件。
此方法可產生大量模塑製品,如密封物、蓋子、軟管、或隔膜。本發明具有特定離子指數之腈橡膠,特別適用於製造O形密封環、平板密封物、波紋密封環、密封套筒、密封蓋、防塵蓋、插塞密封、熱絕緣軟管(添加或未添加PVC)、油冷卻器軟管、吸氣管、伺服控制軟管、或幫浦隔膜。
分析方法:
以氮含量決定腈橡膠之丙烯腈含量(「CAN含量」),係根據DIN 53 625以凱氏測氮法(Kjeldahl method)測定。由於極性共單體之含量,腈橡膠通常可溶於甲基乙基丙酮,其於20℃之溶解度為>85重量%。
慕尼黏度(ML 1+4@100℃)之測定係根據ASTM D 1646於100℃下進行。
測定色安定性,係根據CIEDE 2000測定△E值,摘錄如下。
比較例A1至A8及發明例A 9*與A10*
將表1所列之抗氧化劑混合於腈橡膠之分散劑,其中固體含量為17.5重量%。所有實例皆加入抗氧化劑,其係水性分散劑形式,其中濃度為50重量%。用於所有實例之腈橡膠含有33重量%之丙烯腈系重複單元及67重量%之丁二烯系重複單元。之後,分別將所得乳化劑(A2至A8)與分散劑(A9-A10),其中包含腈橡膠與抗氧化劑,緩慢加入並55℃於下劇烈攪拌成氯化鈣水溶液,其濃度為0.3重量%。經安定化之橡膠凝結物係以水清洗並於60℃之真空烘箱乾燥16小時。隨後,測定慕尼黏度,如前述。之後,一部分之安定化橡膠係於110℃下另外保存48小時,且另一部分之安定化橡膠係於70℃下保存7天。保存作業係於烘箱進行,如本說明書前面所述。於保存時間過後,再次測定慕尼黏度,使得能計算老化指數(ageing
index;AI),其係根據本說明書所提供之公式。
結果列於下表1:
其中A應指Irganox® 1520,其係2-甲基-4,6-雙(辛基磺醯基甲基)酚(BASF AG,Deutschland),B應指Irganox® 1076,其係正十八基-β-(4-羥基-3,5-二-三級丁基
苯基)丙酸酯(BASF AG,Deutschland),及C應指Wingstay® L,其係聚(二環戊二烯-共-對甲苯酚)(Omnova,Italien),BKF應指Vulkanox® BKF,其係2,2'-亞甲基-雙(6-三級丁基)對甲苯酚(Lanxess Deutschland GmbH)。
實施例A1顯示,未安定化橡膠出現實質上老化現象。退化現象於第一乾燥步驟期間已可識別,使得慕尼黏度變為111Mu,其比以至少一抗老化化合物安定化之橡膠高出兩倍以上。以一單一抗老化化合物A、B、或C(實施例A3、A4、A5)安定化之橡膠保存安定性不足。使用二抗老化化合物A與B、A與C、或B與C導致改進,特別是關於長期安定化(long-term stabilization;SS(LT)),其中B與C之組合得到相對最佳結果,然而,安定化仍不足。若使用可比擬之毫莫耳濃度之抗老化化合物,結合抗老化化合物B與C之安定效用類似於Vulkanox BKF所達到之安定效用。然而,Vulkanox BKF具前述之不需要之毒性及環境影響,此外亦難以乳化,這需要其以分散劑形式使用。根據本發明,三組分結合之抗老化化合物A、B、及C產生之安定效用實質上高於單一及二組分系統。特別是,使用三組A、B、及C造成保存安定性改進,其AI指數高於本領域技術人員之預期,其係以互補性第三組分之安定效用加諸於二組分系統之每一者之安定效用。三組A、B、及C之相對量係可變,以針對特定需求調整安定效用。
實施例及比較例B1-B16
欲測試本發明安定劑結合物之安定效用,於聚合作用停止後使用不同腈橡膠之不同水性分散劑。水性分散劑各具腈橡膠之固體含量18±4重量%。腈橡膠之特性如下表2所示,包括不同重複單元之含量及慕尼黏度(ML 1+4,於100℃)。腈橡膠之水性分散劑係由儲槽經供給管泵送至一經攪拌容器。抗老化組分A、B、及C(彼此之抗老化化合物重量比為1:1:1)水性分散劑或另外的Vulkanox BKF(每一者固體含量為50重量%)係保存於單獨儲槽,進料至另一供給管,從而其經注射至含有腈橡膠分散劑之供給管。
之後,以含有額外抗老化組分之橡膠水性分散劑進行凝結作用,係藉加入鉀鹽或鋁鹽,或藉加入酸以降低酸鹼值、清洗、脫水、及乾燥,其係根據本領域習知之程序及前面本說明書之描述。
隨後,安定化橡膠係於烘箱進行各老化條件(分別為48小時/110℃與70℃/7天),之後測定慕尼黏度。根據測得之慕尼黏度,計算各保存安定性SS(ST)與SS(LT)及老化指數AI。
表2提供之結果顯示,相較於習知之安定劑Vulkanox BKF或二組分酚醛抗老化化合物之混合物,或相較於酚醛抗老化化合物與亞磷酸鹽之結合物(後者一般而言揭示於US-A-5,116,534),若橡膠以本發明之三組分系統進行安定化,則老化指數AI明顯變小。
即使習知之抗老化化合物Vulkanox® BKF之用量較高,其安定效用仍低於本發明安定劑之結合物。
於表2中,適用下列含義:
實施例B13與B14之三元單體為甲基丙烯酸。
NW代表2,2'-亞甲基雙[6-壬基-對甲苯酚)(Naugawhite)
TNPP代表參壬基苯基亞磷酸鹽(CAS 26523-78-4)。
欲確認色安定性,根據CIEDE 2000,測定△E值。就此目的,將18克之安定化腈橡膠樣本壓成圓盤,接著以Hunter Associates Lab.,Inc.供應之MiniScan EZ光譜儀分析。
欲比較色安定性,各△E值係測定二次,第一次為橡膠樣本之任何老化前之分離與乾燥後,且第二次為相同安定化橡膠樣本之110℃下老化加工48小時後。結果顯示於表3。
藉由降低△E值,可識別出改進之色安定性,其取決於慕尼安定性及取決於橡膠之丙烯腈與丁二烯含量。僅老化程度不同。可觀察到改進之色安定性,其與用於凝結作用之鹽類無關。
比較例C1及發明例C2
以下表4所示之抗老化化合物分散劑混合於SBR分散劑,其中固體濃度為19,5重量%。含於SBR分散劑之SBR含有23重量%之苯乙烯單元與77重量%之丁二烯單元,其慕尼黏度(ML 1+4,於100℃)為43。所得之分散劑隨後於62℃溫度下加至3重量%之氯化鈉溶液,其中酸鹼值為4且經劇烈攪拌。
從而,所獲得之安定化SBR係以水清洗,並於60℃之真空烘箱乾燥16小時。
於老化調查方面,安定化SBR橡膠係於溫度110℃下保
存48小時,及溫度70℃之相同烘箱保存7天,如前述範例所示。於兩老化程序之後,再次測定慕尼黏度。
其中A=Irganox® 1520;B=Irganox® 1076;C=Wingstay® L;BKF=Vulkanox® BKF,其定義結構如前述。
如同腈橡膠,當使用本發明之三安定化組分時,相較於使用常規習知之Vulkanox® BKF,SBR橡膠亦可識別出較佳之老化安定性如老化指數AI,即使Vulkanox® BKF使用較高之莫耳濃度。同樣地,色安定性如△E(CIEDE 2000)值亦有改進。
Claims (20)
- 一種安定化橡膠,包含: (i)至少一式(I)化合物
- 如申請專利範圍第1項之安定化橡膠,其特徵為該橡膠係不飽和、部分或完全氫化,較佳為選自於由NBR、HNBR、SBR、CR、BR、IIR、BIIR、CIIR、ABR、NIR、SIR、IR、NR、ENR、及其混合物組成之群組。
- 如申請專利範圍第1項之安定化橡膠,其特徵為該橡膠係NBR,較佳為具重複單元,其係衍生自至少一α,β-不飽和腈,更佳為丙烯腈、至少一共軛二烯,更佳為丁二烯、及無、一或多個其他共聚合單體,更佳為選自於丙烯酸及甲基丙烯酸之無或一共聚合單體;或SBR。
- 如申請專利範圍第1至3項任一項之安定化橡膠,包含:(i)至少一,較佳為一式(I)化合物;(ii)至少一,較佳為一式(II)化合物,其中R1為氫;直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代C1-C30烷基,更佳為直鏈或支鏈C12-C24烷基,最佳為直鏈C14-C18烷基;飽和或一或多次不飽和C3-C10碳環基,較佳為C3-C6環烷基;或C3-C10雜環基,較佳為C3-C6雜環基;C6-C24芳基,較佳為C6-C12芳基;C5-C23雜芳基,較佳為C5-C11雜芳基;C7-C30芳基烷基,較佳為C7-C25芳基烷基;C6-C29雜芳基烷基,較佳為C6-C25雜芳基烷基;聚氧基伸烷基醚,較佳為聚氧基乙烯醚、或聚氧基丙烯醚、或聚氧基乙烯-氧基丙烯醚;R2係相同或相異,較佳為相同,且為直鏈或支鏈C1-C4烷基,較佳為甲基、乙基、正丙基、異丙基、正丁基、異丁基、三級丁基、或C6環烷基;以及(iii)至少一,較佳為一式(III)化合物,其中R3為直鏈或支鏈C1-C14烷基,較佳為直鏈或支鏈C1-C10烷基;以及R4係相同或相異,較佳為相同,且為氫;直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代C1-C30烷基;飽和或一或多次不飽和C3-C10碳環基或C3-C10雜環基;C6-C24芳基;C5-C23雜芳基、C7-C30芳基烷基、C6-C29雜芳基烷基、C1-C24烷氧基、C6-C24芳基氧基、C5-C23雜芳基氧 基、C1-C24烷基硫基、或C6-C24芳基硫基,較佳為直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代C1-C25烷基,更佳為直鏈或支鏈、飽和或一或多次不飽和C1-C20烷基,其中該烷基為未經取代或經一或多個取代基取代,該取代基係選自於由胺基、醯亞胺基、烷氧基、芳基氧基、硫基、烷基硫基、芳基硫基、羰基、羧基、氧基羰基、氧代、環氧基、或磺醯氧基組成之群組。
- 如申請專利範圍第4項之安定化橡膠,包含(i)至少一,較佳為一式(I)化合物;(ii)至少一,較佳為一式(II)化合物,其中R1為直鏈或支鏈C15-C18烷基;R2係相同,且為直鏈或支鏈C1-C4烷基,較佳為甲基、乙基、正丙基、異丙基、正丁基、異丁基、三級丁基、或C6環烷基;以及(iii)至少一,較佳為一式(III)化合物,其中R3為直鏈或支鏈C1-C4烷基;以及R4係相同,且為直鏈或支鏈、飽和或一或多次不飽和、未經取代或經取代C6-C14烷基。
- 如申請專利範圍第4項之安定化橡膠,包含(i)一式(I)組分;(ii)一式(II)組分,其中R1為直鏈C18烷基,且兩R2皆為三級丁基; (iii)一式(III)組分,其中兩R4皆為正辛基,且R3為甲基。
- 如申請專利範圍第1至6項任一項之安定化橡膠,包含三組分(i)、(ii)、及(iii),其範圍為0.01至10.0重量%,較佳為0.03至7.5重量%,更佳0.05至5.0重量%,其係以橡膠為100重量份,較佳為腈橡膠。
- 如申請專利範圍第1至7項任一項之安定化橡膠,其特徵為該三組分(i)、(ii)、及(iii)係以(i):(ii):(iii)重量比範圍(0.1-10):1:(0.1-10),較佳為(0.5-2):1:(0.5-2),更佳為(1-2):1:(1-2),最佳為1:1:1或2:1:2之比例使用。
- 如申請專利範圍第1至8項任一項之安定化橡膠,特徵為該安定化橡膠不含化合物(i)、(ii)、及(iii)以外之任何其他抗氧化劑。
- 如申請專利範圍第1至8項任一項之安定化橡膠,特徵為該安定化橡膠額外包含(iv)至少一亞磷酸鹽抗氧化劑,較佳為選自於由三(壬基苯基)亞磷酸鹽、參(2,4-二-三級丁基苯基)亞磷酸鹽、其他烷基芳基亞磷酸鹽、及前述之混合物組成之群組。
- 如申請專利範圍第10項之安定化橡膠,其特徵為該安定化橡膠不含化合物(i)、(ii)、(iii)、及亞磷酸鹽抗氧化劑以外之任何其他抗氧化劑。
- 一種用於製備如申請專利範圍第1至11項中任一項之安定化橡膠之方法,包含以組分(i)、(ii)、(iii)、及任意地(iv)接觸於橡膠,較佳為:(1)於橡膠製備期間,包括橡膠之聚合及後處理,後者包含凝固與分離;或(2)於橡膠製備後之一或多個其他化學轉換步驟,如複分解反應(metathesis reaction)、氫化反應、或類聚合物類似物反應如接枝;及/或(3)於製備基於該腈橡膠之硫化橡膠混合物期間,或該腈橡膠於交聯前進行一或多個進一步化學轉換之後。
- 如申請專利範圍第12項之方法,其特徵為各組分(i)、(ii)、(iii)、及任意地(iv)係接觸該橡膠,不論是單獨地或另以組分(i)、(ii)、(iii)、及任意地(iv)之任何結合類型,較佳為所有三組分(i)、(ii)、(iii)之結合,或任意地所有四組分(i)、(ii)、(iii)、及(iv)之結合。
- 如申請專利範圍第13或12項之方法,其特徵為組分(i)、(ii)、(iii)、及任意地(iv)、或其任何結合類型係作為分散劑。
- 如申請專利範圍第12至14項中任一項之方法,用於製備安定化腈橡膠或經安定化之部分或完全氫化腈橡膠,包含:1)於水性介質進行至少一α,β-不飽和腈、至少一共軛雙烯、及無、一或多個其他共聚合單體之乳化聚合作用,使得於水性介質產生腈橡膠分散劑;2)將該腈橡膠之水性分散劑進行凝固,且分離該腈橡膠;以及 3)若製備安定化之部分或完全氫化腈橡膠,則部分或完全氫化該步驟2)之腈橡膠,特徵為該組分(i)、(ii)、(iii)、及任意地(iv),係於步驟1)、2)、及/或3)期間或之後併入該腈橡膠或安定化之部分或完全氫化腈橡膠。
- 一種由申請專利範圍第12至15項中任一項之方法所獲得之安定化橡膠,較佳為藉由使該橡膠接觸以水性分散劑存在之該三組分(i)、(ii)、及(iii)而獲得。
- 一種硫化橡膠混合物,包含如申請專利範圍第1至11或16項任一項之至少一安定化橡膠,及至少一交聯劑。
- 一種製備如申請專利範圍第17項之硫化橡膠混合物之方法,包含混合該至少一安定化橡膠與該至少一交聯劑,較佳為至少一過氧化物交聯劑或至少一硫系交聯劑。
- 一種製備如申請專利範圍第17項之硫化橡膠混合物之硫化橡膠之方法,包含將該硫化橡膠混合物進行硫化,較佳為於升溫下進行。
- 一種硫化橡膠,其係基於申請專利範圍第1至11或16項中任一項之安定化橡膠。
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US11198750B2 (en) | 2017-03-28 | 2021-12-14 | Zeon Corporation | Method for producing carboxylated nitrile rubber |
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