JP6434626B2 - 色安定性ニトリルゴム - Google Patents
色安定性ニトリルゴム Download PDFInfo
- Publication number
- JP6434626B2 JP6434626B2 JP2017532870A JP2017532870A JP6434626B2 JP 6434626 B2 JP6434626 B2 JP 6434626B2 JP 2017532870 A JP2017532870 A JP 2017532870A JP 2017532870 A JP2017532870 A JP 2017532870A JP 6434626 B2 JP6434626 B2 JP 6434626B2
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- JP
- Japan
- Prior art keywords
- nitrile rubber
- aluminum
- weight
- range
- rubber
- 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.)
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- 229920000459 Nitrile rubber Polymers 0.000 title claims description 150
- 229910052782 aluminium Inorganic materials 0.000 claims description 46
- -1 anion aluminum salt Chemical class 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 44
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 43
- 239000000178 monomer Substances 0.000 claims description 43
- 229920000126 latex Polymers 0.000 claims description 40
- 239000004816 latex Substances 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- 238000005345 coagulation Methods 0.000 claims description 29
- 230000015271 coagulation Effects 0.000 claims description 29
- 238000006116 polymerization reaction Methods 0.000 claims description 29
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 27
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 25
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 20
- 150000002825 nitriles Chemical class 0.000 claims description 18
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 claims description 17
- 238000005406 washing Methods 0.000 claims description 15
- 150000001993 dienes Chemical class 0.000 claims description 14
- 239000004636 vulcanized rubber Substances 0.000 claims description 13
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 12
- 239000003431 cross linking reagent Substances 0.000 claims description 12
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 241001441571 Hiodontidae Species 0.000 claims description 9
- 238000007711 solidification Methods 0.000 claims description 9
- 230000008023 solidification Effects 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 4
- PPQREHKVAOVYBT-UHFFFAOYSA-H dialuminum;tricarbonate Chemical compound [Al+3].[Al+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O PPQREHKVAOVYBT-UHFFFAOYSA-H 0.000 claims description 4
- GRLPQNLYRHEGIJ-UHFFFAOYSA-J potassium aluminium sulfate Chemical compound [Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRLPQNLYRHEGIJ-UHFFFAOYSA-J 0.000 claims description 4
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 claims description 2
- MJWPFSQVORELDX-UHFFFAOYSA-K aluminium formate Chemical compound [Al+3].[O-]C=O.[O-]C=O.[O-]C=O MJWPFSQVORELDX-UHFFFAOYSA-K 0.000 claims description 2
- 235000011126 aluminium potassium sulphate Nutrition 0.000 claims description 2
- 229940118662 aluminum carbonate Drugs 0.000 claims description 2
- RIVXQHNOKLXDBP-UHFFFAOYSA-K aluminum;hydrogen carbonate Chemical compound [Al+3].OC([O-])=O.OC([O-])=O.OC([O-])=O RIVXQHNOKLXDBP-UHFFFAOYSA-K 0.000 claims description 2
- 238000000465 moulding Methods 0.000 claims description 2
- BPLYVSYSBPLDOA-GYOJGHLZSA-N n-[(2r,3r)-1,3-dihydroxyoctadecan-2-yl]tetracosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H](CO)[C@H](O)CCCCCCCCCCCCCCC BPLYVSYSBPLDOA-GYOJGHLZSA-N 0.000 claims description 2
- 229940050271 potassium alum Drugs 0.000 claims description 2
- 235000011127 sodium aluminium sulphate Nutrition 0.000 claims description 2
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 claims 1
- 229940009827 aluminum acetate Drugs 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229920001971 elastomer Polymers 0.000 description 47
- 239000005060 rubber Substances 0.000 description 47
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 35
- 238000001556 precipitation Methods 0.000 description 24
- 239000003995 emulsifying agent Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 230000032683 aging Effects 0.000 description 15
- 229940018560 citraconate Drugs 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 238000005984 hydrogenation reaction Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 13
- 239000000654 additive Substances 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 12
- 239000000194 fatty acid Substances 0.000 description 12
- 229930195729 fatty acid Natural products 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 10
- 238000004140 cleaning Methods 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 150000004665 fatty acids Chemical class 0.000 description 9
- 150000002763 monocarboxylic acids Chemical class 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000003381 stabilizer Substances 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- 125000005907 alkyl ester group Chemical group 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 238000012545 processing Methods 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
- 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
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 150000005690 diesters Chemical class 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 150000002978 peroxides Chemical class 0.000 description 7
- 239000007787 solid Substances 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
- 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 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 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 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 150000001356 alkyl thiols Chemical class 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000000701 coagulant Substances 0.000 description 5
- 238000012937 correction Methods 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000005649 metathesis reaction Methods 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 238000003860 storage Methods 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- 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
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 230000000052 comparative effect 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
- 230000029087 digestion Effects 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 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
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 238000000710 polymer precipitation Methods 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000011282 treatment Methods 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
- 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 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000008052 alkyl sulfonates Chemical class 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000001143 conditioned effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 238000009616 inductively coupled plasma Methods 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 150000002688 maleic acid derivatives Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 238000010063 rubber manufacturing process Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 3
- 229920001897 terpolymer Polymers 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000004073 vulcanization Methods 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
- QKUGKZFASYQCGO-VOTSOKGWSA-N (e)-4-oxo-4-phenylmethoxybut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)OCC1=CC=CC=C1 QKUGKZFASYQCGO-VOTSOKGWSA-N 0.000 description 2
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- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- SINFYWWJOCXYFD-UHFFFAOYSA-N methoxymethyl prop-2-enoate Chemical compound COCOC(=O)C=C SINFYWWJOCXYFD-UHFFFAOYSA-N 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229940074369 monoethyl fumarate Drugs 0.000 description 1
- NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 description 1
- 229940005650 monomethyl fumarate Drugs 0.000 description 1
- IZRZMBCKGLWYSC-UHFFFAOYSA-N n'-(2-aminoethyl)ethane-1,2-diamine;2-methylprop-2-enamide Chemical compound CC(=C)C(N)=O.CC(=C)C(N)=O.CC(=C)C(N)=O.NCCNCCN IZRZMBCKGLWYSC-UHFFFAOYSA-N 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- OQAIUHLITJGRMM-UHFFFAOYSA-N n,n-di(propan-2-yl)hydroxylamine Chemical compound CC(C)N(O)C(C)C OQAIUHLITJGRMM-UHFFFAOYSA-N 0.000 description 1
- BLCKKNLGFULNRC-UHFFFAOYSA-L n,n-dimethylcarbamodithioate;nickel(2+) Chemical compound [Ni+2].CN(C)C([S-])=S.CN(C)C([S-])=S BLCKKNLGFULNRC-UHFFFAOYSA-L 0.000 description 1
- CMAUJSNXENPPOF-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-n-cyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)SC1=NC2=CC=CC=C2S1 CMAUJSNXENPPOF-UHFFFAOYSA-N 0.000 description 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 1
- GFSJJVJWCAMZEV-UHFFFAOYSA-N n-(4-anilinophenyl)-2-methylprop-2-enamide Chemical compound C1=CC(NC(=O)C(=C)C)=CC=C1NC1=CC=CC=C1 GFSJJVJWCAMZEV-UHFFFAOYSA-N 0.000 description 1
- HKLPOBRVSAUJSG-UHFFFAOYSA-N n-(4-anilinophenyl)prop-2-enamide Chemical compound C1=CC(NC(=O)C=C)=CC=C1NC1=CC=CC=C1 HKLPOBRVSAUJSG-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- QUPCNWFFTANZPX-UHFFFAOYSA-M paramenthane hydroperoxide Chemical compound [O-]O.CC(C)C1CCC(C)CC1 QUPCNWFFTANZPX-UHFFFAOYSA-M 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000005385 peroxodisulfate group Chemical group 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-N peroxydisulfuric acid Chemical class OS(=O)(=O)OOS(O)(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000417 polynaphthalene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000010057 rubber processing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- WQSAJTZURUQYKX-UHFFFAOYSA-M sodium 2-methylprop-1-ene naphthalene-1-sulfonate Chemical class [Na+].CC(C)=C.CC(C)=C.[O-]S(=O)(=O)c1cccc2ccccc12 WQSAJTZURUQYKX-UHFFFAOYSA-M 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
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- DZCAZXAJPZCSCU-UHFFFAOYSA-K sodium nitrilotriacetate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CC([O-])=O DZCAZXAJPZCSCU-UHFFFAOYSA-K 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 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
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920006174 synthetic rubber latex Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound 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
- 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
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 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
- 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
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical group 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
- 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
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-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
- 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
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-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
- 235000013311 vegetables Nutrition 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
- 239000002351 wastewater Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000002759 woven fabric Substances 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
- 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
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/20—Incorporating sulfur atoms into the molecule
-
- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/14—Treatment of polymer emulsions
- C08F6/22—Coagulation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/02—Copolymers with acrylonitrile
- C08L9/04—Latex
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
ムーニー粘度は、ムーニー単位(MU)で報告される、ニトリルゴムのムーニー粘度(ML1+4@100℃)の値である)によるアルミニウム指数Eを有するニトリルゴムを提供する。
(i)ニトリルゴムを含有し、かつ重合後に得られるラテックスが、少なくとも1種のアルミニウム塩によって凝固され、上記凝固が、1〜4.5、好ましくは1〜4、より好ましくは1〜3.75、特に1〜3.5の範囲のpHにおいて実行されること、ならびに
(ii)その後のニトリルゴムの洗浄が、6〜12、好ましくは6.25〜11、より好ましくは6.5〜10.5、特に6.75〜10.5の範囲のpHにおいて実行されること
を特徴とする、少なくとも1種のα,β−不飽和ニトリルモノマーおよび少なくとも1種の共役ジエンモノマーの乳化重合によるニトリルゴムの製造プロセスをさらに提供する。
本発明の任意選択的に水素化さしたニトリルゴムは、少なくとも1種のα,β−不飽和ニトリル、少なくとも1種の共役ジエンおよび任意選択的に1種またはそれ以上の共重合性モノマーの繰返し単位を有する。
・モノアルキルマレエート、好ましくは、モノメチルマレエート、モノエチルマレエート、モノプロピルマレエートおよびモノ−n−ブチルマレエート;
・モノシクロアルキルマレエート、好ましくは、モノシクロペンチルマレエート、モノシクロヘキシルマレエートおよびモノシクロペプチルマレエート;
・モノアルキルシクロアルキルマレエート、好ましくは、モノメチルシクロペンチルマレエートおよびモノエチルシクロヘキシルマレエート;
・モノアリールマレエート、好ましくは、モノフェニルマレエート;
・モノベンジルマレエート、好ましくは、モノベンジルマレエート;
・モノアルキルフマレート、好ましくは、モノメチルフマレート、モノエチルフマレート、モノプロピルフマレートおよびモノ−n−ブチルフマレート;
・モノシクロアルキルフマレート、好ましくは、モノシクロペンチルフマレート、モノシクロヘキシルフマレートおよびモノシクロペプチルフマレート;
・モノアルキルシクロアルキルフマレート、好ましくは、モノメチルシクロペンチルフマレートおよびモノエチルシクロヘキシルフマレート;
・モノアリールフマレート、好ましくは、モノフェニルフマレート;
・モノベンジルフマレート、好ましくは、モノベンジルフマレート;
・モノアルキルシトラコネート、好ましくは、モノメチルシトラコネート、モノエチルシトラコネート、モノプロピルシトラコネートおよびモノ−n−ブチルシトラコネート;
・モノシクロアルキルシトラコネート、好ましくは、モノシクロペンチルシトラコネート、モノシクロヘキシルシトラコネートおよびモノシクロペプチルシトラコネート;
・モノアルキルシクロアルキルシトラコネート、好ましくは、モノメチルシクロペンチルシトラコネートおよびモノエチルシクロヘキシルシトラコネート;
・モノアリールシトラコネート、好ましくは、モノフェニルシトラコネート;
・モノベンジルシトラコネート、好ましくは、モノベンジルシトラコネート;
・モノアルキルイタコネート、好ましくは、モノメチルイタコネート、モノエチルイタコネート、モノプロピルイタコネートおよびモノ−n−ブチルイタコネート;
・モノシクロアルキルイタコネート、好ましくは、モノシクロペンチルイタコネート、モノシクロヘキシルイタコネートおよびモノシクロペプチルイタコネート;
・モノアルキルシクロアルキルイタコネート、好ましくは、モノメチルシクロペンチルイタコネートおよびモノエチルシクロヘキシルイタコネート;
・モノアリールイタコネート、好ましくは、モノフェニルイタコネート;
・モノベンジルイタコネート、好ましくは、モノベンジルイタコネート;
・モノアルキルメサコネート、好ましくは、モノエチルメサコネート
が含まれる。
少なくとも1種のα,β−不飽和ニトリルモノマーおよび少なくとも1種の共役ジエンモノマーの乳化重合によってニトリルゴムを製造するための本発明によるプロセスは、
(i)ニトリルゴムを含有し、かつ重合後に得られるラテックスが、少なくとも1種のアルミニウム塩を使用して凝固され、凝固が、1〜4.5、好ましくは1〜4、より好ましくは1〜3.75、特に1〜3.5の範囲のpHで実行されること、および
(ii)その後のニトリルゴムの洗浄が、6〜12、好ましくは6.25〜11、より好ましくは6.5〜10.5、特に6.75〜10.5の範囲のpHで実行されること
を特徴とする。
ラテックス凝固の前または間に、1種またはそれ以上の老化安定剤がラテックスに添加されてもよい。フェノール系、アミン系および他の老化安定剤がこの目的のために適切である。
凝固後、ゴムは典型的にクラムと呼ばれる形態である。したがって、凝固されたゴムの洗浄は、「クラム洗浄」とも呼ばれる。この洗浄のために、脱イオン水または非脱イオン水を使用することが可能である。洗浄は、15〜90℃の範囲の温度、好ましくは20〜80℃の範囲の温度で行なわれる。洗浄水の量は、100重量部のゴムに基づき、0.5〜20重量部、好ましくは、1〜10重量部、より好ましくは1〜5重量部である。
洗浄の終結時に、ニトリルゴムクラムを脱水することが有用であることが見出されている。事前に脱水されたゴムは乾燥機中で乾燥され、適切な例は、流動層乾燥機またはプレート乾燥機である。乾燥温度は80〜150℃である。乾燥操作の収量に向かって温度が低下する温度プログラムによって乾燥させることが好ましい。
ニトリルゴムの調製が、(i)ニトリルゴムの分子量を低下させる複分解反応、または(ii)複分解反応およびその後の水素化または(iii)水素化のみであることも可能である。これらの複分解または水素化反応は、当業者に十分周知であり、かつ文献に記載されている。複分解は、例えば、国際公開第02/100941号パンフレットおよび国際公開第02/100905号パンフレットから既知であり、かつ分子量を減少するために使用可能である。
(R1 mB)lMXn
(式中、Mは、ルテニウムまたはロジウムであり、R1は、同一であるか、または異なって、かつ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アラルキル基である。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、より好ましくはクロロもしくはブロモであり、lは、2、3または4であり、mは2または3であり、かつnは、1、2または3、好ましくは1または3である。)の触媒を使用することが可能である。好ましい触媒は、トリ(トリフェニルホスフィン)ロジウム(I)クロリド、トリ(トリフェニルホスフィン)ロジウム(III)クロリドおよびとトリ(ジメチルスルホキシド)ロジウム(III)クロリド、ならびに式(C6H5)3P)4RhHのテトラキス(トリフェニルホスフィン)ロジウムヒドリド、および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換された相当する化合物である。触媒は少量で使用することが可能である。ポリマーの重量に基づき、0.01〜1重量%の範囲、好ましくは0.03〜0.5重量%の範囲、より好ましくは0.1〜0.3重量%の範囲の量が適切である。
ニトリルゴム中のアクリロニトリル含有量(ACN含有量)の測定のための窒素含有量は、KjeldahlによるDIN53625によって決定する。極性コモノマーの含有量のため、ニトリルゴムは、典型的に、20℃において、メチルエチルケトン中に85重量%より多く可溶性である。
重合は、スターラーシステムを有するオートクレーブ中でバッチ式に実行された。それぞれのオートクレーブバッチ中、Fe(II)に基づき等モル量で、表1に明記されたモノマー混合物、水およびEDTAを使用した。水の量の一部を、最初に、オートクレーブ中に乳化剤と一緒に装填し、そして窒素流でパージした。その後、表1に記載される不安定化したモノマーおよび量の分子量重量調節剤を添加し、そして反応器を密封した。反応器内容物が温度に達した後、重合は、鉄(II)塩(プレミックス溶液の形態)およびパラ−メンタンヒドロペルオキシド(Trigonox(登録商標)NT50)の水溶液の添加によって開始された。
それぞれのNBRラテックスの凝固の前に、Vulkanox(登録商標)BKF(NBR固体に基づき、0.3重量%のVulkanox(登録商標)BKF)の50%分散体をそれぞれに添加した。18%のNBR固体含有量を有し、かつNBRラテックスのポリマー成分が、アクリロニトリルモノマーに基づき44重量%の含有量およびブタジエンモノマーに基づき56重量%の含有量を有する、停止された水性NBRラテックス分散体が使用される。NBR分散体は、表中で明記されたpHにおいて、次第に硫酸アルミニウム溶液(T=70℃)に添加され、そして強力に攪拌される。硫酸アルミニウム溶液の濃度は、NBRゴムの均質クラムが得られるように選択される。NBRゴムに基づく硫酸アルミニウム溶液の量は、9+/−1phrであって、表2または3で明記される。得られた生ゴムは、表2または3に明記されるpHにおいて水(T=60℃)で洗浄され、そして残留湿分含有量が0.6%未満となるように、16時間、60℃において真空オーブン中で乾燥させる。
それぞれのNBRラテックスの凝固の前に、Vulkanox(登録商標)BKF(NBR固体に基づき、0.4重量%のVulkanox(登録商標)BKF)の50%分散体をそれぞれに添加した。18.4%のNBR固体含有量を有し、かつNBRラテックスのポリマー成分が、表4に報告されるムーニー粘度を有し、かつ表4に同様に記載されるアクリロニトリルおよびブタジエンに基づく含有量を有する、停止された水性NBRラテックス分散体が使用される。NBR分散体は、表4に明記されたpHおよび温度において、次第に硫酸アルミニウム溶液に添加され、そして強力に攪拌される。硫酸アルミニウム溶液の濃度は、NBRゴムの均質クラムが得られるように選択される。ゴムに基づく硫酸アルミニウム溶液の量は、表4に報告される。得られた生ゴムは、表4に明記されるpHおよび温度において水で洗浄され、そして残留湿分含有量が0.6%未満となるように、16時間、60℃において真空オーブン中で乾燥させる。
下記の通りニトリルゴムA1〜A18を使用して、加硫ゴムV1〜V18を製造した。加硫性混合物の成分は、100重量部のゴムに基づき、かつ表5に報告される。表5の加硫ゴム番号は、それぞれの場合において、同一番号を有するニトリルゴムに相当する。ニトリルゴムA1は、加硫ゴムV1を製造するために使用され、ニトリルゴムA2は、加硫ゴムV2を製造するために使用される、など。
Claims (15)
- 少なくとも1種のα,β−不飽和ニトリルモノマーおよび少なくとも1種の共役ジエンモノマーの繰り返し単位を含有するニトリルゴムであって、前記ニトリルゴムに基づき、35.0ppm/MU以下の一般式(I)
(式中、
[アルミニウム]は、ppmでの前記ニトリルゴム中のアルミニウム含有量であり、かつ
ムーニー粘度は、ムーニー単位(MU)で報告される、前記ニトリルゴムのムーニー粘度(ML1+4@100℃)の値である)によるアルミニウム指数Eを有することを特徴とする、ニトリルゴム。 - 前記ニトリルゴムに基づき、3ppm/MU〜35ppm/MU以下の範囲、好ましくは5ppm/MU〜35ppm/MU未満の範囲、より好ましくは7ppm/MU〜35ppm/MU未満の範囲の一般式(I)によるアルミニウム指数Eを有することを特徴とする、請求項1に記載のニトリルゴム。
- 1種またはそれ以上のさらなる共重合性モノマーの繰返し単位を追加的に含有する、請求項1または2に記載のニトリルゴム。
- アクリロニトリルおよび1,3−ブタジエンのコポリマーであることを特徴とする、請求項1〜3のいずれか一項に記載のニトリルゴム。
- 前記共役ジエンの割合または合計が、前記ニトリルゴムに基づき、20重量%〜95重量%の範囲、好ましくは40重量%〜90重量%の範囲、より好ましくは60重量%〜85重量%の範囲であり、かつ前記α,β−不飽和ニトリルの割合または合計が、前記ニトリルゴムに基づき、5重量%〜80重量%の範囲、好ましくは10重量%〜60重量%の範囲、より好ましくは15重量%〜40重量%の範囲であり、全モノマーの割合が、それぞれの場合において、最高100重量%までであることを特徴とする、請求項1〜4のいずれか一項に記載のニトリルゴム。
- (i)前記ニトリルゴムを含有し、かつ前記重合後に得られる前記ラテックスが、少なくとも1種のアルミニウム塩によって凝固され、前記凝固が、1〜4.5、好ましくは1〜4、より好ましくは1〜3.75、特に1〜3.5の範囲のpHにおいて実行されること、および
(ii)その後の前記ニトリルゴムの洗浄が、6〜12、好ましくは6.25〜11、より好ましくは6.5〜10.5、特に6.75〜10.5の範囲のpHにおいて実行されること
を特徴とする、少なくとも1種のα,β−不飽和ニトリルモノマーおよび少なくとも1種の共役ジエンモノマーの乳化重合による、請求項1〜5のいずれか一項に記載のニトリルゴムの製造方法。 - 前記ニトリルゴムの凝固が、一価または二価アニオンのアルミニウム塩、好ましくは、ハロゲン化アルミニウム、硝酸アルミニウム、硫酸アルミニウム、炭酸水素アルミニウム、炭酸アルミニウム、ギ酸アルミニウムまたは酢酸アルミニウム、より好ましくは、塩化アルミニウムまたは硫酸アルミニウムである少なくとも1種のアルミニウム塩を使用して実行されることを特徴とする、請求項6に記載のニトリルゴムの製造方法。
- 前記ニトリルゴムの凝固が、塩化アルミニウム、硫酸アルミニウム、硫酸アルミニウムカリウム(カリウムミョウバン)、硫酸アルミニウムナトリウム(ナトリウムミョウバン)またはそれらのいずれかの望ましい混合物を使用して実行されることを特徴とする、請求項7に記載のニトリルゴムの製造方法。
- 前記少なくとも1種のアルミニウム塩が、40重量%〜70%重量、好ましくは40重量%〜60%重量の濃度を有する水溶液の形態で使用され、かつ100重量部のニトリルゴムに基づき、0.5〜50重量部のアルミニウム塩、好ましくは、100重量部のニトリルゴムに基づき、0.8重量%〜40重量%、より好ましくは1.5重量%〜20重量%の塩が使用されることを特徴とする、請求項6〜8のいずれか一項に記載のニトリルゴムの製造方法。
- ステップ(i)の凝固に関して、独占的にアルミニウム塩が使用されるか、あるいは少なくとも1種のアルミニウム塩と同様に、追加的に1種またはそれ以上の他の非アルミニウムベースの沈殿塩が、凝固に使用される全ての塩の全量に基づき、10重量%以下、好ましくは5重量%以下、より好ましくは3重量%以下の量で使用されることを特徴とする、請求項6〜9のいずれか一項に記載のニトリルゴムの製造方法。
- 請求項1〜5のいずれか一項に記載のニトリルゴムおよび少なくとも1種の架橋剤を含んでなる加硫性混合物。
- 請求項1〜5のいずれか一項に記載のニトリルゴムが、少なくとも1種の架橋剤と混合されることを特徴とする、請求項11に記載の加硫性混合物の製造方法。
- 好ましくは成形プロセスにおいて、さらに好ましくは加熱しながら、請求項11に記載の加硫性混合物に加硫を受けさせることを特徴とする、好ましくは成形品の形態での加硫ゴムの製造方法。
- 請求項13に記載の方法によって入手可能な加硫ゴム。
- シール、キャップ、ホースおよび膜から選択される成形品であることを特徴とする、請求項14に記載の加硫ゴム。
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ITMI20111170A1 (it) * | 2011-06-27 | 2012-12-28 | Polimeri Europa Spa | "procedimento per la preparazione di gomme nitrile" |
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CN107108763A (zh) | 2017-08-29 |
MX358291B (es) | 2018-08-13 |
RU2017125781A3 (ja) | 2019-03-28 |
RU2017125781A (ru) | 2019-01-21 |
BR112017012986A2 (pt) | 2018-03-06 |
RU2689632C2 (ru) | 2019-05-28 |
EP3034518A1 (de) | 2016-06-22 |
EP3233929A1 (de) | 2017-10-25 |
KR102440842B1 (ko) | 2022-09-06 |
BR112017012986B1 (pt) | 2021-08-17 |
MX2017008088A (es) | 2017-10-31 |
EP3034518B1 (de) | 2017-05-24 |
TWI682970B (zh) | 2020-01-21 |
PL3034518T3 (pl) | 2017-10-31 |
WO2016096352A1 (de) | 2016-06-23 |
CN107108763B (zh) | 2019-09-06 |
TW201629137A (zh) | 2016-08-16 |
KR20170095862A (ko) | 2017-08-23 |
US20170349687A1 (en) | 2017-12-07 |
US11248078B2 (en) | 2022-02-15 |
JP2018503717A (ja) | 2018-02-08 |
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