TWI503330B - 腈橡膠及其在有機溶劑中之製程 - Google Patents

Info

Publication number

TWI503330B

TWI503330B TW099129425A TW99129425A TWI503330B TW I503330 B TWI503330 B TW I503330B TW 099129425 A TW099129425 A TW 099129425A TW 99129425 A TW99129425 A TW 99129425A TW I503330 B TWI503330 B TW I503330B

Authority

TW

Taiwan

Prior art keywords

group

mono

nitrile rubber

moiety

saturated

Prior art date

2009-09-17

Links

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• Global Dossier
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• 229920000459 Nitrile rubber Polymers 0.000 title claims description 143
• 239000003960 organic solvent Substances 0.000 title claims description 15
• 238000002360 preparation method Methods 0.000 title description 10
• -1 Sulfo, sulfenyl Chemical group 0.000 claims description 134
• 239000003607 modifier Substances 0.000 claims description 80
• 125000003118 aryl group Chemical group 0.000 claims description 62
• 238000000034 method Methods 0.000 claims description 51
• 239000000178 monomer Substances 0.000 claims description 51
• 229920000642 polymer Polymers 0.000 claims description 49
• 229920006395 saturated elastomer Polymers 0.000 claims description 46
• 150000001875 compounds Chemical class 0.000 claims description 31
• 239000000203 mixture Substances 0.000 claims description 30
• 239000003999 initiator Substances 0.000 claims description 27
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
• 125000000217 alkyl group Chemical group 0.000 claims description 24
• 150000002825 nitriles Chemical class 0.000 claims description 24
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
• 150000001993 dienes Chemical class 0.000 claims description 23
• 229910052717 sulfur Inorganic materials 0.000 claims description 23
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
• 150000002148 esters Chemical class 0.000 claims description 22
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 22
• 150000001412 amines Chemical class 0.000 claims description 21
• 125000004429 atom Chemical group 0.000 claims description 21
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 21
• 239000003431 cross linking reagent Substances 0.000 claims description 18
• 239000004593 Epoxy Substances 0.000 claims description 17
• 125000002837 carbocyclic group Chemical group 0.000 claims description 17
• 125000004104 aryloxy group Chemical group 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
• 125000004414 alkyl thio group Chemical group 0.000 claims description 12
• 125000005110 aryl thio group Chemical group 0.000 claims description 12
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 11
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 11
• 239000012948 isocyanate Substances 0.000 claims description 11
• 150000002513 isocyanates Chemical class 0.000 claims description 11
• NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims description 11
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 11
• 239000003381 stabilizer Substances 0.000 claims description 11
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 10
• 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 10
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
• 229920000768 polyamine Polymers 0.000 claims description 10
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 10
• 230000006641 stabilisation Effects 0.000 claims description 9
• 238000011105 stabilization Methods 0.000 claims description 9
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 8
• 229910052794 bromium Inorganic materials 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 238000010526 radical polymerization reaction Methods 0.000 claims description 8
• 230000000087 stabilizing effect Effects 0.000 claims description 8
• 125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 claims description 8
• 239000012989 trithiocarbonate Substances 0.000 claims description 8
• 125000003700 epoxy group Chemical group 0.000 claims description 7
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 125000004149 thio group Chemical group *S* 0.000 claims description 7
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
• BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 6
• SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 6
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 6
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 6
• 229910052740 iodine Inorganic materials 0.000 claims description 6
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
• 229920000728 polyester Polymers 0.000 claims description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
• 150000001345 alkine derivatives Chemical class 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• 150000004676 glycans Chemical class 0.000 claims description 5
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 5
• FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 5
• RYIOLWQRQXDECZ-UHFFFAOYSA-N phosphinous acid Chemical compound PO RYIOLWQRQXDECZ-UHFFFAOYSA-N 0.000 claims description 5
• 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 5
• 229920000515 polycarbonate Polymers 0.000 claims description 5
• 239000004417 polycarbonate Substances 0.000 claims description 5
• 229920000570 polyether Polymers 0.000 claims description 5
• 239000005056 polyisocyanate Substances 0.000 claims description 5
• 229920001228 polyisocyanate Polymers 0.000 claims description 5
• 229920001282 polysaccharide Polymers 0.000 claims description 5
• 239000005017 polysaccharide Substances 0.000 claims description 5
• 239000004814 polyurethane Substances 0.000 claims description 5
• 229920002635 polyurethane Polymers 0.000 claims description 5
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
• 239000004636 vulcanized rubber Substances 0.000 claims description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
• LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 3
• 238000012986 modification Methods 0.000 claims description 3
• 230000004048 modification Effects 0.000 claims description 3
• DDMIPSIJHHJYOM-UHFFFAOYSA-N 2-cyanoethyl benzenecarbodithioate Chemical compound N#CCCSC(=S)C1=CC=CC=C1 DDMIPSIJHHJYOM-UHFFFAOYSA-N 0.000 claims description 2
• IDSLBLWCPSAZBL-UHFFFAOYSA-N 2-cyanopropan-2-yl benzenecarbodithioate Chemical compound N#CC(C)(C)SC(=S)C1=CC=CC=C1 IDSLBLWCPSAZBL-UHFFFAOYSA-N 0.000 claims description 2
• JXPLECNKPVHWMG-UHFFFAOYSA-N 2-phenylethyl benzenecarbodithioate Chemical compound C=1C=CC=CC=1C(=S)SCCC1=CC=CC=C1 JXPLECNKPVHWMG-UHFFFAOYSA-N 0.000 claims description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
• UPLWYDIQUBSEIC-UHFFFAOYSA-N C(C)(=S)SC1=CC=CC=C1.C1(=CC=CC=C1)C(C)C Chemical compound C(C)(=S)SC1=CC=CC=C1.C1(=CC=CC=C1)C(C)C UPLWYDIQUBSEIC-UHFFFAOYSA-N 0.000 claims description 2
• NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 2
• 125000006612 decyloxy group Chemical group 0.000 claims description 2
• IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 2
• LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 claims description 2
• XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 claims description 2
• XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
• 150000003573 thiols Chemical class 0.000 claims 2
• URUCGDAHQNVLQX-UHFFFAOYSA-N C(C1=CC=CC=C1)(=S)S.C1(=CC=CC=C1)C(C)C Chemical compound C(C1=CC=CC=C1)(=S)S.C1(=CC=CC=C1)C(C)C URUCGDAHQNVLQX-UHFFFAOYSA-N 0.000 claims 1
• IRLIKSWIYOSKPL-UHFFFAOYSA-N C(S)(S)=S.C(CC)(=O)OCCCCCCCCCCCC Chemical compound C(S)(S)=S.C(CC)(=O)OCCCCCCCCCCCC IRLIKSWIYOSKPL-UHFFFAOYSA-N 0.000 claims 1
• 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
• 150000005846 sugar alcohols Polymers 0.000 claims 1
• 238000006116 polymerization reaction Methods 0.000 description 60
• 238000006243 chemical reaction Methods 0.000 description 43
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 36
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 25
• 239000002904 solvent Substances 0.000 description 23
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
• 230000008569 process Effects 0.000 description 22
• 238000004132 cross linking Methods 0.000 description 21
• 238000009826 distribution Methods 0.000 description 20
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 19
• 239000000243 solution Substances 0.000 description 19
• 239000002585 base Substances 0.000 description 17
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 16
• 239000003054 catalyst Substances 0.000 description 15
• 239000011593 sulfur Substances 0.000 description 15
• 239000000654 additive Substances 0.000 description 14
• 239000007858 starting material Substances 0.000 description 14
• 238000005984 hydrogenation reaction Methods 0.000 description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
• 229910052786 argon Inorganic materials 0.000 description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
• 239000000047 product Substances 0.000 description 11
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
• 229920001971 elastomer Polymers 0.000 description 10
• 229920006168 hydrated nitrile rubber Polymers 0.000 description 10
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
• SFLRURCEBYIKSS-UHFFFAOYSA-N n-butyl-2-[[1-(butylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound CCCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCCC SFLRURCEBYIKSS-UHFFFAOYSA-N 0.000 description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
• 239000005060 rubber Substances 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 8
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• 239000012190 activator Substances 0.000 description 8
• 125000005907 alkyl ester group Chemical group 0.000 description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 239000003112 inhibitor Substances 0.000 description 8
• 125000004076 pyridyl group Chemical group 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
• 238000004073 vulcanization Methods 0.000 description 8
• 238000007792 addition Methods 0.000 description 7
• 238000007720 emulsion polymerization reaction Methods 0.000 description 7
• IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 7
• 229920002239 polyacrylonitrile Polymers 0.000 description 7
• 229910052703 rhodium Inorganic materials 0.000 description 7
• 239000010948 rhodium Substances 0.000 description 7
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 7
• 125000003396 thiol group Chemical class [H]S* 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
• 229960002447 thiram Drugs 0.000 description 7
• HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 7
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
• 239000011701 zinc Substances 0.000 description 7
• 229910052725 zinc Inorganic materials 0.000 description 7
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
• CFCFZJHCTNKHGJ-UHFFFAOYSA-N 2-dodecylsulfanylcarbothioylsulfanylpropanoic acid Chemical compound CCCCCCCCCCCCSC(=S)SC(C)C(O)=O CFCFZJHCTNKHGJ-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
• 230000032683 aging Effects 0.000 description 6
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• 239000000460 chlorine Substances 0.000 description 6
• HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 6
• 239000003426 co-catalyst Substances 0.000 description 6
• 150000005690 diesters Chemical class 0.000 description 6
• 239000000945 filler Substances 0.000 description 6
• 239000000463 material Substances 0.000 description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
• 229910052757 nitrogen Inorganic materials 0.000 description 6
• 150000002978 peroxides Chemical class 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
• 229920005862 polyol Polymers 0.000 description 6
• 150000003077 polyols Chemical class 0.000 description 6
• 229920001897 terpolymer Polymers 0.000 description 6
• FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 5
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
• 229940018557 citraconic acid Drugs 0.000 description 5
• 229920001577 copolymer Polymers 0.000 description 5
• 229910052802 copper Inorganic materials 0.000 description 5
• 239000010949 copper Substances 0.000 description 5
• 235000014113 dietary fatty acids Nutrition 0.000 description 5
• 239000000194 fatty acid Substances 0.000 description 5
• 229930195729 fatty acid Natural products 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 229910052741 iridium Inorganic materials 0.000 description 5
• GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 5
• 125000005647 linker group Chemical group 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
• 150000002763 monocarboxylic acids Chemical class 0.000 description 5
• 229910052762 osmium Inorganic materials 0.000 description 5
• SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 5
• 229910052707 ruthenium Inorganic materials 0.000 description 5
• XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 description 4
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
• 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
• LUJMEECXHPYQOF-UHFFFAOYSA-N 3-hydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1 LUJMEECXHPYQOF-UHFFFAOYSA-N 0.000 description 4
• TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 4
• VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
• NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-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
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