JP5514740B2 - アルキルチオ末端基を任意に含有し、任意に水素化されたニトリルゴム - Google Patents
アルキルチオ末端基を任意に含有し、任意に水素化されたニトリルゴム Download PDFInfo
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- JP5514740B2 JP5514740B2 JP2010544657A JP2010544657A JP5514740B2 JP 5514740 B2 JP5514740 B2 JP 5514740B2 JP 2010544657 A JP2010544657 A JP 2010544657A JP 2010544657 A JP2010544657 A JP 2010544657A JP 5514740 B2 JP5514740 B2 JP 5514740B2
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- Prior art keywords
- nitrile rubber
- latex
- weight
- optionally
- nitrile
- 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 - Fee Related
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- 229920000459 Nitrile rubber Polymers 0.000 title claims description 201
- 125000004414 alkyl thio group Chemical group 0.000 title description 3
- 229920000126 latex Polymers 0.000 claims description 111
- 239000004816 latex Substances 0.000 claims description 110
- 239000000203 mixture Substances 0.000 claims description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
- 230000002776 aggregation Effects 0.000 claims description 56
- 108010010803 Gelatin Proteins 0.000 claims description 55
- 239000008273 gelatin Substances 0.000 claims description 55
- 229920000159 gelatin Polymers 0.000 claims description 55
- 235000019322 gelatine Nutrition 0.000 claims description 55
- 235000011852 gelatine desserts Nutrition 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 40
- 238000005054 agglomeration Methods 0.000 claims description 38
- 238000006116 polymerization reaction Methods 0.000 claims description 38
- 239000000178 monomer Substances 0.000 claims description 33
- 229910001424 calcium ion Inorganic materials 0.000 claims description 24
- 159000000003 magnesium salts Chemical class 0.000 claims description 23
- 239000011734 sodium Substances 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 239000011575 calcium Substances 0.000 claims description 20
- 238000004220 aggregation Methods 0.000 claims description 19
- 150000002825 nitriles Chemical class 0.000 claims description 17
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000654 additive Substances 0.000 claims description 15
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 150000001993 dienes Chemical class 0.000 claims description 14
- 238000005984 hydrogenation reaction Methods 0.000 claims description 14
- 239000011777 magnesium Substances 0.000 claims description 13
- 229910001425 magnesium ion Inorganic materials 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 159000000007 calcium salts Chemical class 0.000 claims description 12
- 239000003431 cross linking reagent Substances 0.000 claims description 10
- 230000001376 precipitating effect Effects 0.000 claims description 10
- 150000002500 ions Chemical class 0.000 claims description 9
- 238000005649 metathesis reaction Methods 0.000 claims description 8
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 7
- 238000001746 injection moulding Methods 0.000 claims description 5
- 238000000465 moulding Methods 0.000 claims description 5
- 229910001414 potassium ion Inorganic materials 0.000 claims description 5
- 229910001415 sodium ion Inorganic materials 0.000 claims description 5
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 4
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 238000004073 vulcanization Methods 0.000 description 61
- 229920001971 elastomer Polymers 0.000 description 44
- 235000002639 sodium chloride Nutrition 0.000 description 44
- 239000005060 rubber Substances 0.000 description 43
- 238000003860 storage Methods 0.000 description 37
- 239000003995 emulsifying agent Substances 0.000 description 34
- 238000005406 washing Methods 0.000 description 33
- 150000003839 salts Chemical class 0.000 description 32
- -1 alkylated aryl phosphite Chemical compound 0.000 description 31
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- 239000002253 acid Substances 0.000 description 21
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 20
- 210000002966 serum Anatomy 0.000 description 20
- 239000008367 deionised water Substances 0.000 description 17
- 229910021641 deionized water Inorganic materials 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 150000001768 cations Chemical class 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 238000001035 drying Methods 0.000 description 13
- 239000000194 fatty acid Substances 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- 229910001629 magnesium chloride Inorganic materials 0.000 description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 12
- 150000001356 alkyl thiols Chemical class 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 241001441571 Hiodontidae Species 0.000 description 11
- 150000004665 fatty acids Chemical class 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 229910052717 sulfur Chemical group 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- 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 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 238000007792 addition Methods 0.000 description 9
- 229910052791 calcium Inorganic materials 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 239000012266 salt solution Substances 0.000 description 9
- 229960002447 thiram Drugs 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 230000018044 dehydration Effects 0.000 description 8
- 238000006297 dehydration reaction Methods 0.000 description 8
- 239000003792 electrolyte Substances 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 239000007787 solid Substances 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 compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 7
- 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 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 239000001110 calcium chloride Substances 0.000 description 6
- 229910001628 calcium chloride Inorganic materials 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 230000006866 deterioration Effects 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000012190 activator Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 238000005189 flocculation Methods 0.000 description 5
- 230000016615 flocculation Effects 0.000 description 5
- 229910021645 metal ion Inorganic materials 0.000 description 5
- 235000011118 potassium hydroxide Nutrition 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 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 5
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 4
- CPGFMWPQXUXQRX-UHFFFAOYSA-N 3-amino-3-(4-fluorophenyl)propanoic acid Chemical compound OC(=O)CC(N)C1=CC=C(F)C=C1 CPGFMWPQXUXQRX-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 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
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 239000012874 anionic emulsifier Substances 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
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 238000005345 coagulation Methods 0.000 description 4
- 230000015271 coagulation Effects 0.000 description 4
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 description 4
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- 229920000609 methyl cellulose Polymers 0.000 description 4
- 239000001923 methylcellulose Substances 0.000 description 4
- 235000010981 methylcellulose Nutrition 0.000 description 4
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 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
- 229910052707 ruthenium Inorganic materials 0.000 description 4
- 230000035882 stress Effects 0.000 description 4
- 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 4
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 3
- UDQCDDZBBZNIFA-UHFFFAOYSA-N 4-methyl-1,3-dihydrobenzimidazole-2-thione Chemical compound CC1=CC=CC2=C1NC(=S)N2 UDQCDDZBBZNIFA-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Chemical group 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 150000008052 alkyl sulfonates Chemical class 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000004380 ashing Methods 0.000 description 3
- 238000001479 atomic absorption spectroscopy Methods 0.000 description 3
- 235000015278 beef Nutrition 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000029087 digestion Effects 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical group 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 159000000001 potassium salts Chemical class 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 210000003491 skin Anatomy 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003871 sulfonates Chemical group 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical group 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000012991 xanthate Substances 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- AUMBZPPBWALQRO-UHFFFAOYSA-L zinc;n,n-dibenzylcarbamodithioate Chemical compound [Zn+2].C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1 AUMBZPPBWALQRO-UHFFFAOYSA-L 0.000 description 3
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
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- FCQRKDSALKMOGU-UHFFFAOYSA-K rhodium(3+);triphenylphosphane;trichloride Chemical compound Cl[Rh](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FCQRKDSALKMOGU-UHFFFAOYSA-K 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
- 238000010092 rubber production Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical class [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 238000010059 sulfur vulcanization Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical group CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 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
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- HXOGQBSDPSMHJK-UHFFFAOYSA-N triethoxy(6-methylheptyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCC(C)C HXOGQBSDPSMHJK-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- UWSYCPWEBZRZNJ-UHFFFAOYSA-N trimethoxy(2,4,4-trimethylpentyl)silane Chemical compound CO[Si](OC)(OC)CC(C)CC(C)(C)C UWSYCPWEBZRZNJ-UHFFFAOYSA-N 0.000 description 1
- NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-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
- 238000001291 vacuum drying Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- ZWGHMFAEGCOFIU-UHFFFAOYSA-L zinc butoxy-[butyl(propan-2-yl)-lambda4-sulfanylidene]methanethiolate Chemical compound C(C)(C)S(=C(OCCCC)[S-])CCCC.[Zn+2].C(C)(C)S(=C(OCCCC)[S-])CCCC ZWGHMFAEGCOFIU-UHFFFAOYSA-L 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
- NEYNBSGIXOOZGZ-UHFFFAOYSA-L zinc;butoxymethanedithioate Chemical compound [Zn+2].CCCCOC([S-])=S.CCCCOC([S-])=S NEYNBSGIXOOZGZ-UHFFFAOYSA-L 0.000 description 1
- DRKOTOCDZAUOFY-UHFFFAOYSA-L zinc;n,n-bis(7-methyloctyl)carbamodithioate Chemical compound [Zn+2].CC(C)CCCCCCN(C([S-])=S)CCCCCCC(C)C.CC(C)CCCCCCN(C([S-])=S)CCCCCCC(C)C DRKOTOCDZAUOFY-UHFFFAOYSA-L 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C1/00—Treatment of rubber latex
- C08C1/14—Coagulation
- C08C1/15—Coagulation characterised by the coagulants used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with nitriles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/139—Open-ended, self-supporting conduit, cylinder, or tube-type article
Description
本発明にしたがってカチオン含有量を測定するには、以下の方法が有用であることが判明しているため、これを用いる:ニトリルゴム0.5gを白金るつぼ中で550℃での乾式灰化によって消化した後、その灰を塩酸中に溶解させる。この消化液を脱イオン水で適当に希釈した後、以下の波長にて、この酸マトリクスに合わせた較正溶液に対して、金属含有量をICP−OES(誘導結合プラズマ−発光分析)で測定することが可能である。
カルシウム:317.933nm、
カリウム:766.491nm、
マグネシウム:285.213nm、
ナトリウム:589.592nm。
消化液中の元素の濃度と使用する測定機器の感度とに応じて、使用するそれぞれの波長用の較正の線形領域に試料溶液の濃度を合わせる(B.Welz “Atomic Absorption Spectrometry”、2nd Ed.、Verlag Chemie、Weinheim 1985)。
によるイオン指数(「II」)が5〜30ppm×g/molの範囲、特に好ましくは10〜25ppm×g/molの範囲である。これらのカルシウムイオン、マグネシウムイオン、ナトリウムイオン、カリウムイオンの濃度を、上述したようにして測定する。
本発明のニトリルゴムは、好都合なことに保存安定性が極めて良好であり、不純物(特に重合で使用する乳化剤の不純物)がわずかしか含まれない。乳化剤は、洗浄水中のCOD値の高さという形で反映される。
SS=MV2−MV1 (II)
式中、
MV1は、ニトリルゴムのMooney粘度の値であり、
MV2は、同じニトリルゴムの100℃で48時間保管後のMooney粘度の値である。
ニトリルゴム中に残留する乳化剤の量は、ラテックスの凝集後に水性相中に存在する可溶性有機成分を求めて間接的に測定する。これに用いる指標は、DIN 38 409、パート41、H 41−1およびH 41−2によるラテックス漿液のCOD(化学的酸素要求量)である。CODの測定においては、硫酸銀触媒の存在下にて硫酸で強酸性化した重クロム酸カリウムによって、有機成分を定量的に酸化させる。次に、未反応の重クロム酸カリウムの量を鉄(II)イオンで逆滴定する。CODは、DIN規格での、mg酸素/リットル溶液、またはg酸素/リットル溶液で示す。固形分濃度または沈殿剤容積の異なるラテックスを用いる実験の比較可能性を改善するために、漿液のCODをニトリルゴムの質量で割る(除算)。この場合、CODの単位はg酸素/kgNBRである。この値を、以下のようにして得る。
CODNBR:NBRの1kgに対するCOD(g酸素/kgNBR)
CODserum:漿液のCOD(実験的に測定)[g酸素/kgserum]
mserum:ラテックス1kg中の漿液の質量[kg]
mpr:使用する沈殿剤の質量[kg/kgラテックス]
mNBR:ラテックス1kg中のニトリルゴムの質量[kg]
SC:ラテックスの固形分含有量(重量%}
本発明のニトリルゴムは、少なくとも1種のα,β−不飽和ニトリルと、少なくとも1種の共役ジエンと、任意選択で場合によっては1種以上の別の共重合可能なモノマーの繰り返し単位を有する。
(i)エマルション重合で得られるラテックスのpHが凝集前に少なくとも6であり、
(ii)少なくとも1種のマグネシウム塩を沈殿剤として用いてラテックスの凝集を行ない、ここでは任意選択で最大40重量%のマグネシウム塩をカルシウム塩に置き換えてもよく、
(iii)ラテックス凝集用の共沈剤としてゼラチンを使用し、
(iv)共沈剤(iii)と接触させる前はラテックスの温度を50℃以下の温度に設定し、その後温度を100℃まで上昇させ、
(v)沈殿剤としてのカルシウム塩の非存在下でラテックスを凝集させる場合には、ラテックスの凝集および/または凝集したラテックスの処理を、カルシウムイオンを含有する水を用いて行うことを特徴とする製造方法を提供するものである。
形成されるニトリルゴムの分子量を調節するために、少なくとも1種の分子量調節剤を使用する。
- 2,4,4,6,6−ペンタメチルヘプタン−2−チオール、
- 2,3,4,6,6−ペンタメチルヘプタン−2−チオール、
- 2,3,4,6,6−ペンタメチルヘプタン−3−チオール
を含むC12−メルカプタンの混合物を使用してもよく、これは、その調製方法と一緒に、独国特許出願公開第10 2007 024009号明細書に記載されている。この特定の混合物は、硫化水素とトリイソブテンとを連続プロセスで0℃〜−60℃の範囲の温度にて反応させることによって得ることができ、この連続プロセスでは、
(a)反応前に硫化水素を乾燥させ、
(b)用いるトリイソブテンは70ppm以下の含水量を有し、
(c)三フッ化ホウ素を、用いるトリイソブテンに基づいて1.5重量%以下の量で触媒として使用し、
(d)三フッ化ホウ素との錯体を形成する化合物の非存在下にて反応を行い、
(e)反応後に反応混合物を水性アルカリ溶液と接触させて触媒を除去する。
本発明の方法におけるラテックスの凝集は、沈殿剤として少なくとも1種のマグネシウム塩を用いて行なわれ、任意選択で最大40重量%までのマグネシウム塩をカルシウム塩に置き換えてもよい。同時に、ラテックスの凝集および/または凝集したラテックスの後処理を、カルシウムイオンを含有する水を用いて行なうことができる。これは、沈殿剤として1種類のマグネシウム塩しか用いずに凝集を行なう場合に重要である。
上述した沈殿剤以外に、本発明の方法ではゼラチンを共沈剤として用いることが重要である。
凝集後、ニトリルゴムは通常、クラムの形態で存在する。したがって、凝集したNBRの洗浄をクラム洗浄ともいう。この凝集したクラムを洗浄するためには、脱イオン水(「DW」と略すこともある)または脱イオン化されていない水(「BW」と略すこともある)のいずれかを用いることができる。脱イオン化されていない水は、カルシウムイオンを含有する。
洗浄終了後、一般にニトリルゴムクラムを脱水する。これは通常、二段階で実施される。第1段階では、ゴムクラムを機械的に予備脱水する。第2段階では、残りの水を蒸発させる。予備脱水と乾燥はいずれも好ましくは連続的に行なう。機械的な予備脱水のための好適な装置は、ストレーナのスリットまたはスクリューから水を側面に沿って絞り出すストレーナスクリューであり、この中で機械的脱水が生成物流に対して行なわれる(Weldingの原理)。
(R1 mB)lMXn
で表される触媒を用いることができる。式中、Mはルテニウムまたはロジウムであり、R1基は同一または異なっており、各々、C1〜C8アルキル基、C4〜C8シクロアルキル基、C6〜C15アリール基、またはC7〜C15アラルキル基であり、Bは、リン、ヒ素、硫黄、またはスルホキシド基S=Oであり、Xは水素またはアニオン、好ましくはハロゲン、特に好ましくは塩素または臭素であり、lは、2、3または4であり、mは2または3であり、nは、1、2または3、好ましくは1または3である。好ましい触媒は、塩化トリス(トリフェニルホスフィン)ロジウム(I)、塩化トリス(トリフェニルホスフィン)ロジウム(III)、及び塩化トリス(ジメチルスルホキシド)ロジウム(III)であり、式((C6H5)3P)4RhHの水素化テトラキス(トリフェニルホスフィン)ロジウムならびに、トリフェニルホスフィンが完全にまたは部分的にトリシクロヘキシルホスフィンで置き換えられた対応する化合物である。触媒は少量で使用可能である。ポリマーの重量に対して0.01〜1重量%の範囲の量、好ましくは0.03〜0.5重量%の範囲、特に好ましくは0.1〜0.3重量%の範囲の量が適している。
一般情報
I カチオン含有量の測定
カチオン含有量を測定するには、ニトリルゴム0.5gを白金るつぼ中、550℃での乾式灰化によって消化した後、塩酸中で灰を溶かした。その消化液を脱イオン水で適当に希釈した後、その酸マトリクスに合わせた較正溶液に対して以下の波長においてICP−OES(誘導結合プラズマ−発光分析)によって金属含有量を測定した。
カルシウム:317.933nm、
マグネシウム:285.213nm、
カリウム:766.491nm、
ナトリウム:589.592nm
消化液中の元素の濃度と使用する測定機器の感度に応じて、試料溶液の濃度を、各場合に用いられる波長に対する較正の線形領域に合わせた(B. Welz “Atomic Absorption Spectrometry”, 2nd Ed., Verlag Chemie, Weinheim 1985, chapters 9.1, 9.1.1, 9.1.2 and 9.1.3; pp. 251〜262)。
100℃で48時間の温風保管の前後のMooney粘度によって、乾燥NBRゴムをキャラクタライズする。すなわち、乾燥後すぐ(すなわち温風保管前)に一度と、続いて100℃で48時間の温風老化後にも、直接Mooney粘度を測定した。
剪断ディスク型粘度計を使用して、DIN 53 523に準じて120℃で初期加硫挙動(Mooneyスコーチ)を測定する。この測定には小型ローター(S)を用いる。「MS 5(120℃)」は、Mooney値が最小値から5Mooney単位分だけ上昇するまでの分単位での時間である。
加硫物について、DIN 53 504に準拠してゴムの機械的特性(さまざまな伸び率での応力、最大抗張力、破断点伸びなど)を測定する。
DIN EN 14582に基づく方法によって、本発明のニトリルゴムの塩素含有量を以下のようにして測定する。方法A:Parr圧力容器中で、過酸化ナトリウムおよび硝酸カリウムの溶融物中で、ニトリルゴム試料を消化する。得られる溶融物に亜硫酸塩溶液を添加し、この混合物を硫酸で酸性化する。得られた溶液中に形成された塩化物を、硝酸銀溶液を用いる電位差滴定によって測定し、塩素として算出する。
以下の表1に示す配合に基づいてNBRラテックスを製造した。すべての出発物質の量は、モノマー混合物100重量部あたりの重量部で示す。重合は、重合転化率80%に達するまで、18℃の温度で10時間にわたって行なった。
脱イオン水(DW水)360g
アルキルフェノールポリグリコールエーテル40g(Lanxess Deutschland GmbHのEmulgator NP(登録商標) 10)
Lanxess Deutschland GmbHのVulkanox(登録商標) BKF 400g
沈殿に使用した塩溶液の濃度と塩の量を、結晶水を含めずにそれぞれの場合で計算した。ラテックスの凝集に使用した塩、塩溶液の濃度、NBRを基準にして使用した塩の量、凝集温度、洗浄時の温度、洗浄時間を以下の表に挙げる。
t10:10%の転化が達成された時刻
t90:90%の転化が達成された時刻
である。
Claims (10)
- 少なくとも1種の分子量調節剤の存在下で、少なくとも1種のα,β−不飽和ニトリルと、少なくとも1種の共役ジエンと、任意選択で場合により1種以上のさらなる共重合可能なモノマーとのエマルション重合によってニトリルゴムを製造するための方法であって、重合で得られ且つニトリルゴムを含有するラテックスを凝集させ、次に凝集させたニトリルゴムを洗浄する製造方法において、
(i)エマルション重合で得られるラテックスが、凝集前に少なくとも6のpHを有し、
(ii)ラテックスの凝集が、沈殿剤として少なくとも1種のマグネシウム塩を用いて行なわれ、ここでは任意選択で最大40重量%までのマグネシウム塩をカルシウム塩に置き換えてもよく、
(iii)凝集のための共沈剤としてゼラチンを用い、
(iv)共沈剤(iii)との接触前は、ラテックスの温度を50℃以下の温度に設定し、温度を次に100℃まで上昇させ、
(v)沈殿剤としてのカルシウム塩の非存在下でラテックスの凝集を行なう場合には、ラテックスの凝集および/または凝集したラテックスの後処理を、カルシウムイオンを含有する水を用いて行なう、
ことを特徴とする製造方法。 - 得られたニトリルゴムに、次に(i)メタセシス反応のみ、あるいは(ii)メタセシス反応と続いての水素化、あるいは(iii)水素化のみをほどこす、請求項1に記載の製造方法。
- 少なくとも1種のα,β−不飽和ニトリルと、少なくとも1種の共役ジエンと、任意選択で場合により1種以上のさらなる共重合可能なモノマーとの繰り返し単位を含み、ニトリルゴムに対してそれぞれマグネシウムイオンを100〜180ppmの範囲の濃度で、カルシウムイオンを50〜145ppmの範囲の濃度で有する、請求項1に記載の製造方法によって得られる、ニトリルゴム。
- 2,2,4,6,6−ペンタメチルヘプタン−4−チオおよび/または2,4,4,6,6−ペンタメチルヘプタン−2−チオおよび/または2,3,4,6,6−ペンタメチルヘプタン−2−チオおよび/または2,3,4,6,6−ペンタメチルヘプタン−3−チオ末端基を有する、請求項3に記載のニトリルゴム。
- 請求項2に記載の製造方法により得ることができる、任意選択で水素化されていてもよいニトリルゴム。
- 請求項3〜5のいずれか一項に記載の少なくとも1種のニトリルゴムあるいは請求項6に記載の少なくとも1種の任意選択で水素化されていてもよいニトリルゴムと、少なくとも1種の架橋剤と、任意選択により場合によってはさらなる添加剤とを含有する、加硫可能な混合物。
- 請求項3〜5のいずれか一項に記載の少なくとも1種のニトリルゴムあるいは請求項6に記載の少なくとも1種の任意選択で水素化されていてもよいニトリルゴムと、少なくとも1種の架橋剤と、任意選択により場合によってはさらなる添加剤とを混合することによる、請求項7に記載の加硫可能な混合物の製造方法。
- 請求項7に記載の加硫可能な混合物を、成形プロセスで、好ましくは射出成形プロセスを用いる成形プロセスで加硫化する、成形品の製造方法。
- 請求項9に記載の製造方法によって得られる成形品。
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PCT/EP2009/050460 WO2009095313A1 (de) | 2008-01-29 | 2009-01-16 | Optional alkylthio-endgruppen enthaltende optional hydrierte nitrilkautschuke |
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-
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EP2238177A1 (de) | 2010-10-13 |
RU2464278C2 (ru) | 2012-10-20 |
WO2009095313A1 (de) | 2009-08-06 |
KR20100115779A (ko) | 2010-10-28 |
CN101925614B (zh) | 2013-08-07 |
BRPI0906732A2 (pt) | 2015-07-07 |
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US20110123748A1 (en) | 2011-05-26 |
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