CN1688647A - 用于硫化橡胶的可接枝的4-氨基-3-亚磺酰基-取代的二苯胺稳定剂 - Google Patents
用于硫化橡胶的可接枝的4-氨基-3-亚磺酰基-取代的二苯胺稳定剂 Download PDFInfo
- Publication number
- CN1688647A CN1688647A CNA038238233A CN03823823A CN1688647A CN 1688647 A CN1688647 A CN 1688647A CN A038238233 A CNA038238233 A CN A038238233A CN 03823823 A CN03823823 A CN 03823823A CN 1688647 A CN1688647 A CN 1688647A
- Authority
- CN
- China
- Prior art keywords
- phenyl
- formula
- compound
- tertiary butyl
- alkyl
- 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.)
- Pending
Links
- 239000003381 stabilizer Substances 0.000 title abstract description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 23
- 229920001971 elastomer Polymers 0.000 claims abstract description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 15
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 13
- 239000000806 elastomer Substances 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 230000015556 catabolic process Effects 0.000 claims abstract description 4
- 238000006731 degradation reaction Methods 0.000 claims abstract description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 4
- -1 tackifier Substances 0.000 claims description 123
- 239000000203 mixture Substances 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 42
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 230000003647 oxidation Effects 0.000 claims description 19
- 238000007254 oxidation reaction Methods 0.000 claims description 19
- 239000004636 vulcanized rubber Substances 0.000 claims description 17
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 14
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 12
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 9
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 claims description 9
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 7
- 230000003078 antioxidant effect Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000003568 thioethers Chemical class 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 4
- 229920003051 synthetic elastomer Polymers 0.000 claims description 4
- 239000012936 vulcanization activator Substances 0.000 claims description 4
- 239000004902 Softening Agent Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 239000012747 synergistic agent Substances 0.000 claims description 3
- 230000001960 triggered effect Effects 0.000 claims description 3
- 238000004073 vulcanization Methods 0.000 claims description 3
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 150000008301 phosphite esters Chemical class 0.000 claims description 2
- 239000005061 synthetic rubber Substances 0.000 claims description 2
- 230000003064 anti-oxidating effect Effects 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 claims 1
- 239000002530 phenolic antioxidant Substances 0.000 claims 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims 1
- 229920001897 terpolymer Polymers 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 238000002845 discoloration Methods 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000003921 oil Substances 0.000 description 21
- 239000000654 additive Substances 0.000 description 19
- 239000002585 base Substances 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 15
- 230000000996 additive effect Effects 0.000 description 14
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000005060 rubber Substances 0.000 description 12
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 11
- 229910000071 diazene Inorganic materials 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 8
- 239000012964 benzotriazole Substances 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229940059574 pentaerithrityl Drugs 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000000843 powder Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- GAODDBNJCKQQDY-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCC)=C1 GAODDBNJCKQQDY-UHFFFAOYSA-N 0.000 description 5
- DKHJONPHCWFBAX-UHFFFAOYSA-N 3-butyl-3h-1-benzofuran-2-one Chemical group C1=CC=C2C(CCCC)C(=O)OC2=C1 DKHJONPHCWFBAX-UHFFFAOYSA-N 0.000 description 5
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 235000019241 carbon black Nutrition 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 150000002429 hydrazines Chemical class 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 5
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 4
- ICHKVCYUNCKCGL-UHFFFAOYSA-N CN(C)C.OCCCCCCO Chemical compound CN(C)C.OCCCCCCO ICHKVCYUNCKCGL-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- KJIOQYGWTQBHNH-UHFFFAOYSA-N methyl butylhexanol Natural products CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 4
- COVMBDWAODLWIB-UHFFFAOYSA-N n'-(2-hydroxyethyl)oxamide Chemical compound NC(=O)C(=O)NCCO COVMBDWAODLWIB-UHFFFAOYSA-N 0.000 description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- 229950006389 thiodiglycol Drugs 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- 229940057402 undecyl alcohol Drugs 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 3
- JQTYAZKTBXWQOM-UHFFFAOYSA-N 4-n-octan-2-yl-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CCCCCC)=CC=C1NC1=CC=CC=C1 JQTYAZKTBXWQOM-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 229920003052 natural elastomer Polymers 0.000 description 3
- 229920001194 natural rubber Polymers 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- GPOGLVDBOFRHDV-UHFFFAOYSA-N (2-nonylphenyl) dihydrogen phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(O)O GPOGLVDBOFRHDV-UHFFFAOYSA-N 0.000 description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical group 0.000 description 2
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 2
- ZRMMVODKVLXCBB-UHFFFAOYSA-N 1-n-cyclohexyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1=CC=CC=C1 ZRMMVODKVLXCBB-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XURGPLKLBUMZTN-UHFFFAOYSA-N 2-butyl-3-methylbenzene-1,4-diol Chemical group CCCCC1=C(C)C(O)=CC=C1O XURGPLKLBUMZTN-UHFFFAOYSA-N 0.000 description 2
- LCQXXVFFJHBYME-UHFFFAOYSA-N 2-butyl-4-hydroxybenzoic acid Chemical group CCCCC1=CC(O)=CC=C1C(O)=O LCQXXVFFJHBYME-UHFFFAOYSA-N 0.000 description 2
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical compound ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 2
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 2
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 2
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 description 2
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- MSGFMKMFGGXSTO-UHFFFAOYSA-N C(C)(C)(C)C=1C=C(C(=CC1O)CN)CCCC Chemical compound C(C)(C)(C)C=1C=C(C(=CC1O)CN)CCCC MSGFMKMFGGXSTO-UHFFFAOYSA-N 0.000 description 2
- MGEODAGTUMQOJX-UHFFFAOYSA-N CCCCCCCCCCCCCCC([O])CCC Chemical compound CCCCCCCCCCCCCCC([O])CCC MGEODAGTUMQOJX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VHOQXEIFYTTXJU-UHFFFAOYSA-N Isobutylene-isoprene copolymer Chemical compound CC(C)=C.CC(=C)C=C VHOQXEIFYTTXJU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 125000006487 butyl benzyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 229940051250 hexylene glycol Drugs 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- GXFQBBOZTNQHMW-UHFFFAOYSA-N n'-(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound CC1(C)CC(NCCCCCCN)CC(C)(C)N1 GXFQBBOZTNQHMW-UHFFFAOYSA-N 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 description 2
- 229940038384 octadecane Drugs 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000003431 oxalo group Chemical group 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 2
- 238000005987 sulfurization reaction Methods 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 description 2
- HQEPZWYPQQKFLU-UHFFFAOYSA-N (2,6-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(O)=C1C(=O)C1=CC=CC=C1 HQEPZWYPQQKFLU-UHFFFAOYSA-N 0.000 description 1
- GOZHNJTXLALKRL-UHFFFAOYSA-N (5-benzoyl-2,4-dihydroxyphenyl)-phenylmethanone Chemical class OC1=CC(O)=C(C(=O)C=2C=CC=CC=2)C=C1C(=O)C1=CC=CC=C1 GOZHNJTXLALKRL-UHFFFAOYSA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 1
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical class NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PPNDFSTWANYHQM-UHFFFAOYSA-N 1-(3-amino-4-hydroxyphenyl)dodecan-1-one Chemical compound CCCCCCCCCCCC(=O)C1=CC=C(O)C(N)=C1 PPNDFSTWANYHQM-UHFFFAOYSA-N 0.000 description 1
- UDAKRDQBQXLJHF-UHFFFAOYSA-N 1-(3-amino-4-hydroxyphenyl)nonan-1-one Chemical compound CCCCCCCCC(=O)C1=CC=C(O)C(N)=C1 UDAKRDQBQXLJHF-UHFFFAOYSA-N 0.000 description 1
- MQQKTNDBASEZSD-UHFFFAOYSA-N 1-(octadecyldisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSCCCCCCCCCCCCCCCCCC MQQKTNDBASEZSD-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- KPZBEZVZFBDKCG-UHFFFAOYSA-N 2,4-dibutylphenol Chemical group CCCCC1=CC=C(O)C(CCCC)=C1 KPZBEZVZFBDKCG-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- PANIBUVGEJDJGE-UHFFFAOYSA-N 2-(2-sulfophenoxy)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1OC1=CC=CC=C1S(O)(=O)=O PANIBUVGEJDJGE-UHFFFAOYSA-N 0.000 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 1
- HOHDYZFUHAZLIT-UHFFFAOYSA-N 2-(aminomethyl)-n-ethylaniline Chemical compound CCNC1=CC=CC=C1CN HOHDYZFUHAZLIT-UHFFFAOYSA-N 0.000 description 1
- WXHVQMGINBSVAY-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 WXHVQMGINBSVAY-UHFFFAOYSA-N 0.000 description 1
- ITLDHFORLZTRJI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-5-octoxyphenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1N1N=C2C=CC=CC2=N1 ITLDHFORLZTRJI-UHFFFAOYSA-N 0.000 description 1
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical group CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BVNPSIYFJSSEER-UHFFFAOYSA-H 2-[2-(1,3,2-benzodioxastibol-2-yloxy)phenoxy]-1,3,2-benzodioxastibole Chemical compound O([Sb]1Oc2ccccc2O1)c1ccccc1O[Sb]1Oc2ccccc2O1 BVNPSIYFJSSEER-UHFFFAOYSA-H 0.000 description 1
- PMRTXCQELXDQEH-UHFFFAOYSA-N 2-[carboxymethyl-[2-oxo-2-(2,2,6,6-tetramethylpiperidin-4-yl)oxyethyl]amino]acetic acid Chemical compound CC1(C)CC(OC(=O)CN(CC(O)=O)CC(O)=O)CC(C)(C)N1 PMRTXCQELXDQEH-UHFFFAOYSA-N 0.000 description 1
- HHPDFYDITNAMAM-UHFFFAOYSA-N 2-[cyclohexyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)C1CCCCC1 HHPDFYDITNAMAM-UHFFFAOYSA-N 0.000 description 1
- NVKDNDRCUYIBLB-UHFFFAOYSA-N 2-amino-4-butylphenol Chemical compound CCCCC1=CC=C(O)C(N)=C1 NVKDNDRCUYIBLB-UHFFFAOYSA-N 0.000 description 1
- OCDFZRIOTQBMDV-UHFFFAOYSA-N 2-amino-4-octadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC=C(O)C(N)=C1 OCDFZRIOTQBMDV-UHFFFAOYSA-N 0.000 description 1
- ABBAQSIKFAPOHH-UHFFFAOYSA-N 2-butyl-2-[(4-hydroxyphenyl)methyl]propanedioic acid Chemical group CCCCC(C(O)=O)(C(O)=O)CC1=CC=C(O)C=C1 ABBAQSIKFAPOHH-UHFFFAOYSA-N 0.000 description 1
- JWCCIWXOJZMKFG-UHFFFAOYSA-N 2-butyl-4-(2-methylpropyl)phenol Chemical group CCCCC1=CC(CC(C)C)=CC=C1O JWCCIWXOJZMKFG-UHFFFAOYSA-N 0.000 description 1
- VSPNJSYHURBSJS-UHFFFAOYSA-N 2-butyl-4-(methoxymethyl)phenol Chemical group CCCCC1=CC(COC)=CC=C1O VSPNJSYHURBSJS-UHFFFAOYSA-N 0.000 description 1
- OGUOSVCZUXJHJQ-UHFFFAOYSA-N 2-butyl-4-[(dimethylamino)methyl]phenol Chemical group CCCCC1=CC(CN(C)C)=CC=C1O OGUOSVCZUXJHJQ-UHFFFAOYSA-N 0.000 description 1
- DAKZLOJXUDPQIL-UHFFFAOYSA-N 2-butyl-4-ethylphenol Chemical group CCCCC1=CC(CC)=CC=C1O DAKZLOJXUDPQIL-UHFFFAOYSA-N 0.000 description 1
- ZRADTNJSPQDCDV-UHFFFAOYSA-N 2-butyl-4-methoxyphenol Chemical group CCCCC1=CC(OC)=CC=C1O ZRADTNJSPQDCDV-UHFFFAOYSA-N 0.000 description 1
- GTLMTHAWEBRMGI-UHFFFAOYSA-N 2-cyclohexyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C2CCCCC2)=C1 GTLMTHAWEBRMGI-UHFFFAOYSA-N 0.000 description 1
- KDHONNUUDHJCID-UHFFFAOYSA-N 2-cyclopentyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C2CCCC2)=C1 KDHONNUUDHJCID-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- LHHLLQVLJAUUDT-UHFFFAOYSA-N 2-ethylhexyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCC(CC)CCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O LHHLLQVLJAUUDT-UHFFFAOYSA-N 0.000 description 1
- XSXYESVZDBAKKT-UHFFFAOYSA-N 2-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1O XSXYESVZDBAKKT-UHFFFAOYSA-N 0.000 description 1
- WBJWXIQDBDZMAW-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carbonyl chloride Chemical compound C1=CC=CC2=C(C(Cl)=O)C(O)=CC=C21 WBJWXIQDBDZMAW-UHFFFAOYSA-N 0.000 description 1
- VSKJLJHPAFKHBX-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 VSKJLJHPAFKHBX-UHFFFAOYSA-N 0.000 description 1
- DHKGWJHJJZJZGD-UHFFFAOYSA-N 2-tert-butyl-4-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=C(O)C(C(C)(C)C)=C1 DHKGWJHJJZJZGD-UHFFFAOYSA-N 0.000 description 1
- LZHCVNIARUXHAL-UHFFFAOYSA-N 2-tert-butyl-4-ethylphenol Chemical compound CCC1=CC=C(O)C(C(C)(C)C)=C1 LZHCVNIARUXHAL-UHFFFAOYSA-N 0.000 description 1
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 1
- LKYSPVIJUOKXCB-UHFFFAOYSA-N 3,6-dimethyl-2,4-bis(octylsulfanyl)phenol Chemical compound CCCCCCCCSC1=CC(C)=C(O)C(SCCCCCCCC)=C1C LKYSPVIJUOKXCB-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-L 3-(2-carboxylatoethylsulfanyl)propanoate Chemical compound [O-]C(=O)CCSCCC([O-])=O ODJQKYXPKWQWNK-UHFFFAOYSA-L 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- SAEZGDDJKSBNPT-UHFFFAOYSA-N 3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)N(C)C(C)(C)C1 SAEZGDDJKSBNPT-UHFFFAOYSA-N 0.000 description 1
- FBIXXCXCZOZFCO-UHFFFAOYSA-N 3-dodecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)NC(C)(C)C1 FBIXXCXCZOZFCO-UHFFFAOYSA-N 0.000 description 1
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 1
- RYAIMSPHUVXLQI-UHFFFAOYSA-N 4-(aminomethyl)-2-(benzotriazol-2-yl)phenol Chemical compound NCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 RYAIMSPHUVXLQI-UHFFFAOYSA-N 0.000 description 1
- BCZQMWDTKGBZFG-UHFFFAOYSA-N 4-[(4-hydroxy-2,6-dimethylphenyl)disulfanyl]-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1SSC1=C(C)C=C(O)C=C1C BCZQMWDTKGBZFG-UHFFFAOYSA-N 0.000 description 1
- OVARTXYXUGDZHU-UHFFFAOYSA-N 4-hydroxy-n-phenyldodecanamide Chemical compound CCCCCCCCC(O)CCC(=O)NC1=CC=CC=C1 OVARTXYXUGDZHU-UHFFFAOYSA-N 0.000 description 1
- RDZBAYGNTNYHAH-UHFFFAOYSA-N 4-hydroxy-n-phenyloctadecanamide Chemical compound CCCCCCCCCCCCCCC(O)CCC(=O)NC1=CC=CC=C1 RDZBAYGNTNYHAH-UHFFFAOYSA-N 0.000 description 1
- OILMLWAZYNVPMG-UHFFFAOYSA-N 4-methyl-2-nonylphenol Chemical compound CCCCCCCCCC1=CC(C)=CC=C1O OILMLWAZYNVPMG-UHFFFAOYSA-N 0.000 description 1
- HFOCLDGNWXEELG-UHFFFAOYSA-N 4-methyl-2-octadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC(C)=CC=C1O HFOCLDGNWXEELG-UHFFFAOYSA-N 0.000 description 1
- MNDJKTIGCWCQIG-UHFFFAOYSA-N 4-n-naphthalen-2-ylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=CC=C(C=CC=C2)C2=C1 MNDJKTIGCWCQIG-UHFFFAOYSA-N 0.000 description 1
- ZEZSYLKJRJYGEQ-UHFFFAOYSA-N 4-n-octan-2-ylbenzene-1,4-diamine Chemical compound CCCCCCC(C)NC1=CC=C(N)C=C1 ZEZSYLKJRJYGEQ-UHFFFAOYSA-N 0.000 description 1
- NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
- GHUDTURWNYDCKX-UHFFFAOYSA-N 4-oxo-4-(2,2,6,6-tetramethylpiperidin-4-yl)oxybutanoic acid Chemical compound CC1(C)CC(OC(=O)CCC(O)=O)CC(C)(C)N1 GHUDTURWNYDCKX-UHFFFAOYSA-N 0.000 description 1
- BVNWQSXXRMNYKH-UHFFFAOYSA-N 4-phenyl-2h-benzotriazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1NN=N2 BVNWQSXXRMNYKH-UHFFFAOYSA-N 0.000 description 1
- PZBQVZFITSVHAW-UHFFFAOYSA-N 5-chloro-2h-benzotriazole Chemical compound C1=C(Cl)C=CC2=NNN=C21 PZBQVZFITSVHAW-UHFFFAOYSA-N 0.000 description 1
- SBCXTRGDSYTHEM-UHFFFAOYSA-N 6-ethyl-3-methyl-2,4-bis(octylsulfanyl)phenol Chemical compound CCCCCCCCSC1=CC(CC)=C(O)C(SCCCCCCCC)=C1C SBCXTRGDSYTHEM-UHFFFAOYSA-N 0.000 description 1
- UPIBRNLZADUDPA-UHFFFAOYSA-N 6-tert-butyl-3-methyl-2,4-bis(octylsulfanyl)phenol Chemical compound CCCCCCCCSC1=CC(C(C)(C)C)=C(O)C(SCCCCCCCC)=C1C UPIBRNLZADUDPA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- OHNNRLYWLNCESG-UHFFFAOYSA-N C(C)(C)(C)C=1C(=C(C=C(C1)CCOCC(CCCCCC)=C=O)N1N=C2C(=N1)C=CC(=C2)Cl)O Chemical compound C(C)(C)(C)C=1C(=C(C=C(C1)CCOCC(CCCCCC)=C=O)N1N=C2C(=N1)C=CC(=C2)Cl)O OHNNRLYWLNCESG-UHFFFAOYSA-N 0.000 description 1
- OJFRBIHEBZDTSB-UHFFFAOYSA-N C(C)(C)(C)C=1C(=C(C=C(C1)CCOCC(CCCCCC)=C=O)N1N=C2C(=N1)C=CC=C2)O Chemical compound C(C)(C)(C)C=1C(=C(C=C(C1)CCOCC(CCCCCC)=C=O)N1N=C2C(=N1)C=CC=C2)O OJFRBIHEBZDTSB-UHFFFAOYSA-N 0.000 description 1
- KYGSBSWBGHALLC-UHFFFAOYSA-N C(C)(C)(C)C=1C(=CC(=C(C1)C(CC(C)CCCCCCCCCCCC)S)CN)O Chemical compound C(C)(C)(C)C=1C(=CC(=C(C1)C(CC(C)CCCCCCCCCCCC)S)CN)O KYGSBSWBGHALLC-UHFFFAOYSA-N 0.000 description 1
- CPUMIQKFVWMTKY-UHFFFAOYSA-N C(C)(C)(C)C=1C(=CC(=C(C1)CCCCC)CN)O Chemical compound C(C)(C)(C)C=1C(=CC(=C(C1)CCCCC)CN)O CPUMIQKFVWMTKY-UHFFFAOYSA-N 0.000 description 1
- RTJUWEUCUSQYAV-UHFFFAOYSA-N C(C)(C)(C)C=1C=C(C=C(C1O)CN)CCC(=O)O Chemical compound C(C)(C)(C)C=1C=C(C=C(C1O)CN)CCC(=O)O RTJUWEUCUSQYAV-UHFFFAOYSA-N 0.000 description 1
- RVGUQHPMQVMUHN-UHFFFAOYSA-N C(C)C1(CC(=CC=C1)CN)NC1=CC=C(C=C1)N Chemical compound C(C)C1(CC(=CC=C1)CN)NC1=CC=C(C=C1)N RVGUQHPMQVMUHN-UHFFFAOYSA-N 0.000 description 1
- RNPFAAQKINNIJX-UHFFFAOYSA-N C(CCC)C(C1=CC=CC=C1)P(O)(=O)OC Chemical group C(CCC)C(C1=CC=CC=C1)P(O)(=O)OC RNPFAAQKINNIJX-UHFFFAOYSA-N 0.000 description 1
- GKRYOTUQPZKDFB-UHFFFAOYSA-N C1=CC=CC=C1C(=O)OO.[Cl] Chemical compound C1=CC=CC=C1C(=O)OO.[Cl] GKRYOTUQPZKDFB-UHFFFAOYSA-N 0.000 description 1
- BTKLMGGKCQZDNC-UHFFFAOYSA-N CC(C)CCCCCCC[O] Chemical compound CC(C)CCCCCCC[O] BTKLMGGKCQZDNC-UHFFFAOYSA-N 0.000 description 1
- DJRCMVCFUPOPKC-UHFFFAOYSA-N CCCCCCCCCCCC(=NO)C1=CC=C(C)C=C1O Chemical compound CCCCCCCCCCCC(=NO)C1=CC=C(C)C=C1O DJRCMVCFUPOPKC-UHFFFAOYSA-N 0.000 description 1
- JDSBOMSXCJQHIB-UHFFFAOYSA-N CCCCCCCCCCCCC([O])CCC Chemical compound CCCCCCCCCCCCC([O])CCC JDSBOMSXCJQHIB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920004939 Cariflex™ Polymers 0.000 description 1
- GNNPJZUDJSDYRK-UHFFFAOYSA-N ClC1=CC=2C(=NN(N2)C2=C(C(=CC(=C2)CN)C(C)(C)C)O)C=C1 Chemical compound ClC1=CC=2C(=NN(N2)C2=C(C(=CC(=C2)CN)C(C)(C)C)O)C=C1 GNNPJZUDJSDYRK-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 description 1
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical class C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- IWGBGUINMSOOKP-UHFFFAOYSA-N OC1=C(C(=O)CCCCCCCCCCC)C=NN1C1=CC=CC=C1 Chemical class OC1=C(C(=O)CCCCCCCCCCC)C=NN1C1=CC=CC=C1 IWGBGUINMSOOKP-UHFFFAOYSA-N 0.000 description 1
- GUKVZEMNDHZQQE-UHFFFAOYSA-N OC1=C(C=C(C=C1CCCCCCCCCCCC)CN)N1N=C2C(=N1)C=CC=C2 Chemical compound OC1=C(C=C(C=C1CCCCCCCCCCCC)CN)N1N=C2C(=N1)C=CC=C2 GUKVZEMNDHZQQE-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000124033 Salix Species 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- SDQHEDWESBKPAV-UHFFFAOYSA-N [4-(1,3,5-triazin-2-yl)phenyl]methanamine Chemical class C1=CC(CN)=CC=C1C1=NC=NC=N1 SDQHEDWESBKPAV-UHFFFAOYSA-N 0.000 description 1
- DWDAZFJBSZTCCM-UHFFFAOYSA-N [O]C1CCCCC1 Chemical compound [O]C1CCCCC1 DWDAZFJBSZTCCM-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- PYHXGXCGESYPCW-UHFFFAOYSA-N alpha-phenylbenzeneacetic acid Natural products C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000021523 carboxylation Effects 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000010389 delta-tocopherol Nutrition 0.000 description 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 1
- JXIKLABFTFGIQB-UHFFFAOYSA-N dioxaphosphocine Chemical compound C=1C=COOP=CC=1 JXIKLABFTFGIQB-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RSNDQTNQQQNXRN-UHFFFAOYSA-N dodecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCOP(O)O RSNDQTNQQQNXRN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RITJXHQMLFOANH-UHFFFAOYSA-N ethoxy(1-phenylpentyl)phosphinic acid Chemical group CCCCC(P(O)(=O)OCC)C1=CC=CC=C1 RITJXHQMLFOANH-UHFFFAOYSA-N 0.000 description 1
- LCGAYNAPJAKKQK-UHFFFAOYSA-N ethoxy-[1-(4-hydroxyphenyl)pentyl]phosphinic acid Chemical group C(C)OP(O)(=O)C(C1=CC=C(C=C1)O)CCCC LCGAYNAPJAKKQK-UHFFFAOYSA-N 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 229920006226 ethylene-acrylic acid Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000004079 fireproofing Methods 0.000 description 1
- 235000010382 gamma-tocopherol Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229920005555 halobutyl Polymers 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- XXEJPLGMRLGRPB-UHFFFAOYSA-N hexadecyl 2-butyl-4-hydroxybenzoate Chemical group CCCCCCCCCCCCCCCCOC(=O)c1ccc(O)cc1CCCC XXEJPLGMRLGRPB-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 1
- FGFUBBNNYLNVLJ-UHFFFAOYSA-N indolone Natural products C1=CC=C2C(=O)C=NC2=C1 FGFUBBNNYLNVLJ-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 125000002960 margaryl 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])C([H])([H])C([H])([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 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 229910021518 metal oxyhydroxide Inorganic materials 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 1
- VRBLLGLKTUGCSG-UHFFFAOYSA-N methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O VRBLLGLKTUGCSG-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YVYHWOZEQUFKOB-UHFFFAOYSA-N n'-[3-(dimethylamino)propyl]oxamide Chemical compound CN(C)CCCNC(=O)C(N)=O YVYHWOZEQUFKOB-UHFFFAOYSA-N 0.000 description 1
- DHXOCDLHWYUUAG-UHFFFAOYSA-N n,n-didodecylhydroxylamine Chemical compound CCCCCCCCCCCCN(O)CCCCCCCCCCCC DHXOCDLHWYUUAG-UHFFFAOYSA-N 0.000 description 1
- WQAJFRSBFZAUPB-UHFFFAOYSA-N n,n-dioctylhydroxylamine Chemical compound CCCCCCCCN(O)CCCCCCCC WQAJFRSBFZAUPB-UHFFFAOYSA-N 0.000 description 1
- UBINNYMQZVKNFF-UHFFFAOYSA-N n-benzyl-1-phenylmethanimine oxide Chemical compound C=1C=CC=CC=1C=[N+]([O-])CC1=CC=CC=C1 UBINNYMQZVKNFF-UHFFFAOYSA-N 0.000 description 1
- FWFBCOSKYDQTSS-UHFFFAOYSA-N n-butyl-1,2,2,6,6-pentamethyl-3-(1,3,5-triazin-2-yl)piperidin-4-amine Chemical compound CCCCNC1CC(C)(C)N(C)C(C)(C)C1C1=NC=NC=N1 FWFBCOSKYDQTSS-UHFFFAOYSA-N 0.000 description 1
- BYYFPVDBAHOLDX-UHFFFAOYSA-N n-dodecyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCCCCCC)C1=CC=CC=C1 BYYFPVDBAHOLDX-UHFFFAOYSA-N 0.000 description 1
- LRUUZFQPCUFYPV-UHFFFAOYSA-N n-dodecyldodecan-1-imine oxide Chemical compound CCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCC LRUUZFQPCUFYPV-UHFFFAOYSA-N 0.000 description 1
- KWUZCAVKPCRJPO-UHFFFAOYSA-N n-ethyl-4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound C1=CC(NCC)=CC=C1C1=NC2=CC=C(C)C=C2S1 KWUZCAVKPCRJPO-UHFFFAOYSA-N 0.000 description 1
- GBMIPYGHTZRCRH-UHFFFAOYSA-N n-ethylethanimine oxide Chemical compound CC[N+]([O-])=CC GBMIPYGHTZRCRH-UHFFFAOYSA-N 0.000 description 1
- ZRPOKHXBOZQSOX-UHFFFAOYSA-N n-heptadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCC ZRPOKHXBOZQSOX-UHFFFAOYSA-N 0.000 description 1
- DBCWENWKZARTGU-UHFFFAOYSA-N n-heptadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC=[N+]([O-])CCCCCCCCCCCCCCCCC DBCWENWKZARTGU-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCBLWIBXXQTAW-UHFFFAOYSA-N n-hexadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCC WGCBLWIBXXQTAW-UHFFFAOYSA-N 0.000 description 1
- GCDJFNYVSDFWDB-UHFFFAOYSA-N n-hexadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC GCDJFNYVSDFWDB-UHFFFAOYSA-N 0.000 description 1
- HQYHEBGVNAJVAA-UHFFFAOYSA-N n-hexadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCNO HQYHEBGVNAJVAA-UHFFFAOYSA-N 0.000 description 1
- FHAFFFSIDLDWQA-UHFFFAOYSA-N n-hexadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC=[N+]([O-])CCCCCCCCCCCCCCCC FHAFFFSIDLDWQA-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- LVZUNTGFCXNQAF-UHFFFAOYSA-N n-nonyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCCC)C1=CC=CC=C1 LVZUNTGFCXNQAF-UHFFFAOYSA-N 0.000 description 1
- ZXGDIORKSOYRMQ-UHFFFAOYSA-N n-octadecylheptadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCC ZXGDIORKSOYRMQ-UHFFFAOYSA-N 0.000 description 1
- MCMMSXFAWOGWQE-UHFFFAOYSA-N n-octadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC MCMMSXFAWOGWQE-UHFFFAOYSA-N 0.000 description 1
- TWHQPVYYDWEGRT-UHFFFAOYSA-N n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCNO TWHQPVYYDWEGRT-UHFFFAOYSA-N 0.000 description 1
- HORBOHJHQGXXOR-UHFFFAOYSA-N n-octadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCCC HORBOHJHQGXXOR-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KISSZQOBOUCLMH-UHFFFAOYSA-N n-tetradecylhydroxylamine Chemical compound CCCCCCCCCCCCCCNO KISSZQOBOUCLMH-UHFFFAOYSA-N 0.000 description 1
- SLYJXPKHTZCZOG-UHFFFAOYSA-N n-tetradecyltetradecan-1-imine oxide Chemical compound CCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCC SLYJXPKHTZCZOG-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- ZVEZMVFBMOOHAT-UHFFFAOYSA-N nonane-1-thiol Chemical compound CCCCCCCCCS ZVEZMVFBMOOHAT-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- CSWFWSPPZMEYAY-UHFFFAOYSA-N octadecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(O)O CSWFWSPPZMEYAY-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])C([H])([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 1
- 125000002958 pentadecyl 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])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 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
- C07C323/35—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
- C07C323/36—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/36—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atoms of the amino groups bound to hydrogen atoms or to carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
- C08K5/3725—Sulfides, e.g. R-(S)x-R' containing nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
式(I)化合物可用作防止氧化、热、动力学、光引发和/或臭氧引发降解的弹性体稳定剂,其中:R1为C1-C18烷基、C5-C12-环烷基、苯基、苄基或烯丙基;n为1或2;如果n为1,R2则为C4-C18烷基、C5-C12环烷基、芳基或杂芳基、苄基、烯丙基、(CH2) mCOOR3或为(CH2) mCN;如果n为2,R2则为-S-(CH2) p-S或-S-(CH2) 2-[O-(CH2) 2] m-S,R3为C1-C18烷基、苄基、烯丙基;m为1或2;且p为2-12中的一个数。它们也适合用作防止基体与弹性体接触所致接触变色的弹性体稳定剂。
Description
本发明涉及4-氨基-3-亚磺酰基-二苯胺类新型稳定剂,涉及包含易受氧化、热、动力学或光和/或臭氧引发降解的弹性体和作为稳定剂的至少一种4-氨基-3-亚磺酰基-二苯胺类化合物的组合物,涉及所述稳定剂防止基体与弹性体接触所致变色的用途,并用作弹性体抗臭氧龟裂剂来防止由氧化、热、动力学或光和/或臭氧引发的降解,也涉及相应的方法和将所述稳定剂接枝到弹性体上的方法。
同所有聚合物一样,例如橡胶产品(硫化橡胶)的弹性体易受氧化、热、动力学或光引发降解。对二烯类橡胶硫化橡胶造成损害的一个特别因素为臭氧。臭氧进攻在橡胶(硫化橡胶)中大量存在的碳-碳双键,并通过称为臭氧分解的机制,对橡胶制品产生明显的损害如典型的表面龟裂使橡胶失去作用。当橡胶制品在动力学应力下时这种损害尤其严重。
为防止臭氧的损害,硫化橡胶中通常加入选自对苯二胺类化合物的抗氧化剂[参见Russel A.Mazzeo等,“Tire Technology International”1994,36-46页;或Donald E.Miller等,Rubber World,200(5),13-23(1989)]。这些化合物有非常好的保护作用,特别是在动力学条件下,但会产生明显的内在颜色(变色),并且由于高迁移速度,这些化合物产生严重的接触变色(染色),即染料通过直接接触转移到其它基体/产品上。这意味着这些应用于现有技术的稳定剂不能用作无炭黑或“非黑”橡胶制品的稳定剂,并且它们也不适用于含有炭黑并将用于与浅色产品直接接触的(黑)橡胶制品。
对这类稳定剂的需求将是持续的:虽然它们有内在颜色,但例如由于化学键合到橡胶链上,不会将颜色转移到其它制品上。
现在,已发现4-氨基-3-亚磺酰基-二苯胺类化合物尤其适合作为易由氧化、热、动力学或光和/或臭氧引发降解的弹性体的稳定剂。
因此,本发明提供了式I化合物
其中
R1为C1-C18烷基、C5-C12-环烷基、苯基、苄基或烯丙基;
n为1或2;
如果n为1,R2则为C4-C18烷基、C5-C12环烷基、芳基或杂芳基、苄基、烯丙基、(CH2)mCOOR3,或为(CH2)mCN;
如果n为2,R2则为-S-(CH2)p-S或-S-(CH2)2-[O-(CH2)2]m-S-;
R3为C1-C18烷基、苄基、烯丙基;
m为1或2;且
p为2-12间的一个数;
优选的式I化合物为以下的那些化合物,其中:
R1为C2-C8-烷基、环己基、苯基、苄基或烯丙基;特别为2-丙基、-CH(CH3)-CH2-CH(CH3)2、-CH(CH3)-CH(CH3)2、2-辛基、环己基;
如果n为1,R2则为C4-C18烷基、环己基、苯基、苄基、(CH2)2COOR3,或为(CH2)2CN;
如果n为2,R2则为-S-(CH2)p-S-,其中p在2-6之间,或为-S-(CH2)2-O-(CH2)2-S-;
尤其为以下的那些化合物,其中:n为1,且R2为烷基、环己基、(CH2)2COOR3或(CH2)2CN,最优选的R2为正辛基、叔壬基、正十二烷基、叔十二烷基;和R3为C1-C18烷基、特别为异辛基、异十三烷基、正十二烷基、十八烷基(stearyl)。
含有多达十八个碳原子的烷基为支化或非支化的基团,例如甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、2-乙基丁基、正戊基、异戊基、1-甲基戊基、1,3-二甲基丁基、正己基、1-甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、2-乙基己基、1,1,3-三甲基己基、1,1,3,3-四甲基戊基、壬基、癸基、十一烷基、1-甲基十一烷基、十二烷基、1,1,3,3,5,5-六甲基己基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基。优选的R2之一为C4-C18烷基,尤其为C6-C12烷基,例如C8-C12烷基。
芳基或杂芳基优选为苯基、萘基或吡啶基,特别为苯基。
叔丁基代表1,1-二甲基乙基;表示为例如叔壬基或叔十二烷基的叔烷基长链烷基代表叔烷基-C(RR’R”)的异构体混合物,其中R、R’和R”各自为烷基,总的碳原子数如所指定。
异辛基或异十三烷基为伯烷基的异构体混合物(可从例如PhillpsPetroleum购得)。
式I化合物的实例有:
式I化合物可由已知方法获得,例如以式II的相应硫醚为原料,
其中,n、R1和R2同式①定义,通过氧化反应,通常与有机或无机过氧化物或过酸反应。实例有H2O2、H2O2-脲加成物、叔丁基氢过氧化物、枯基过氧氢、过甲酸、过乙酸(或H2O2/乙酸的组合)、三氯过乙酸、间-氯过苯甲酸。优选反应在有机溶剂中进行,优选为极性溶剂,如醇、醚、酮或其混合物。合适溶剂的实例有乙醇、2-丙醇、(聚)乙二醇、(聚)乙二醇醚、丙酮、丁酮、甲基-异丁基-酮。温度通常在-5℃至+80℃之间,并优选在35℃至50℃之间。氧化剂的量可为低于化学计量的量、化学计量的量或过量。氧化剂的过量部分可用适当的方法破坏,例如用水或有机或无机还原剂洗涤,如焦硫酸钠。任选粗亚砜化合物进一步纯化,如用闪色谱法纯化。
从WO-A-02/42262中已知一些式II化合物;其它化合物可以类似方法通过合适的醌二亚胺与硫醇反应获得。因此通过式III的醌二亚胺
和式IV的硫醇
R2-(SH)n (IV)
反应可得到硫醚加合物,其中,n、R1和R2同式(I)定义。
反应条件通常与上述那些氧化步骤类似,有机溶剂存在且温度适宜在-5℃至约100℃范围内。
本发明也提供了一些新的式II’的硫醚化合物
其中n为1或2,
R1为C1-C18烷基、C5-C12-环烷基、苯基、苄基或烯丙基;和
如果n为1,R2则为叔壬基、叔十二烷基、(CH2)2COOR3或(CH2)2CN,其中R3为C1-C18烷基,尤其为异辛基、异十三烷基、正十二烷基、十八烷基;或
如果n为2,R2则为-S-(CH2)p-S-,p为2-6之间的数;条件是式II’a化合物除外。
优选的式II’化合物为以下那些化合物,其中
n为1或2,特别为1,
R1为2-丙基、-CH(CH3)-CH2-CH(CH3)2、-CH(CH3)-CH(CH3)2、2-辛基或环己基,特别为2-丙基,且
如果n为1,R2则为叔壬基、叔十二烷基或(CH2)2COOR3,其中R3为支链C4-C18烷基,特别为异辛基、异十三烷基;或
如果n为2,R2则为-S-(CH2)p-S-,其中p为2到6之间的数。
一些特别有技术意义的式II’化合物为以下的那些化合物,其中n为1,和
a)R1为-CH(CH3)-CH2-CH(CH3)2,且R2为叔十二烷基;
b)R1为-CH(CH3)-CH2-CH(CH3)2,且R2为CH2CH2COO-异辛基;
c)R1为-CH(CH3)-CH2-CH(CH3)2,且R2为叔壬基;
d)R1为2-丙基,且R2为叔十二烷基;
e)R1为2-丙基,且R2为叔壬基。
成分b)适用于稳定弹性体,特别是浅色弹性体,以防止由氧化、热、动力学或光和/或臭氧引发的降解。
弹性体应理解为是指大分子物质,这种大分子物质在室温、小负载下发生相当大的变形后可迅速再大致恢复它们原来的形状。也可参见Hans-Georg Elias,“An Introduction to Polymer Science”,第12部分“弹性体”,388-393页,1997,VCH Verlagsgesellschaft mbH,Weinheim,Germany或“Ullmann’s Encyclopedia of Industrial Chemistry,第5版,全修订版,第A23卷”,221-440页(1993)。
可存在于本发明组合物中的弹性体实例有以下物质:
1.二烯类聚合物,例如聚丁二烯或聚异戊二烯。
2.单烯类和二烯类两者共聚物或与其它乙烯基单体的共聚物,例如丙烯-异丁烯共聚物、丙烯-丁二烯共聚物、异丁烯-异戊二烯共聚物、乙烯-丙烯酸烷基酯共聚物、乙烯-异丁烯酸烷基酯共聚物、乙烯-醋酸乙烯酯共聚物、丙烯腈-丁二烯共聚物,也可为乙烯与丙烯和如己二烯、双环戊二烯或亚乙基降冰片烯等二烯的三聚物。
3.苯乙烯或α-甲基苯乙烯与二烯或与丙烯酸衍生物的共聚物,例如苯乙烯-丁二烯、苯乙烯-丁二烯-丙烯酸烷基酯和苯乙烯-丁二烯-甲基丙烯酸烷基酯;苯乙烯的嵌断共聚物,如苯乙烯-丁二烯-苯乙烯、苯乙烯-异戊二烯-苯乙烯和苯乙烯-乙烯丁烯-苯乙烯,以及从后三者制备得来的粘合剂。
4.含有卤素的聚合物,例如聚氯丁二烯、氯化橡胶、异丁烯-异戊二烯的氯化或溴化共聚物(卤化丁基橡胶)。
5.天然橡胶。
6.天然或合成橡胶的水乳状液,例如天然橡胶乳胶或羧化苯乙烯-丁二烯共聚物的乳胶。
优选要保护的弹性体为硫化弹性体。特别有意义的是天然橡胶和合成橡胶,及由此制备的硫化橡胶。特别优选聚二烯硫化橡胶、含有卤素的聚二烯硫化橡胶、聚二烯共聚物硫化橡胶,特别是苯乙烯-丁二烯共聚物硫化橡胶和乙烯-丙烯三聚体硫化橡胶。
按照以需要稳定的弹性体重量计,通常加入到需要稳定的弹性体中的成分b)的量为0.05%-10%,例如0.1%-5%,优选为0.5%-3.0%。
除a)组分和b)成分外,本发明组合物可包含其它添加剂,例如以下添加剂:
1.抗氧化剂。
1.1烷基化单酚,例如2,6-二-叔丁基-4-甲基苯酚、2-叔丁基-4,6-二-甲基苯酚、2,6-二-叔丁基-4-乙基苯酚、2,6-二-叔丁基-4-正丁基苯酚、2,6-二-叔丁基-4-异丁基苯酚、2,6-二环戊基-4-甲基苯酚、2-(α-甲基环己基)-4,6-二甲基苯酚、2,6-二(十八烷基)-4-甲基苯酚、2,4,6-三环己基苯酚、2,6-二-叔丁基-4-甲氧基甲基苯酚、侧链为直链或支链的壬基苯酚(例如2,6-二-壬基-4-甲基苯酚)、2,4-二甲基-6-(1’-甲基十一烷-1’-基)苯酚、2,4-二甲基-6-(1’-甲基十七烷-1’-基)苯酚、2,4-二甲基-6-(1’-甲基十三烷-1’-基)苯酚以及它们的混合物。
1.2烷基硫基甲基苯酚,例如2,4-二辛基硫基甲基-6-叔丁基苯酚、2,4-二辛基硫基甲基-6-甲基苯酚、2,4-二辛基硫基甲基-6-乙基苯酚、2,6-二-十二烷基硫基甲基-4-壬基苯酚。
1.3氢醌和烷基化氢醌,例如2,6-二-叔丁基-4-甲氧基苯酚、2,5-二-叔丁基氢醌、2,5-二-叔戊基氢醌、2,6-二苯基-4-十八烷氧基苯酚、2,6-二-叔丁基氢醌、2,5-二-叔丁基-4-羟基苯甲醚、3,5-二-叔丁基-4-羟基苯甲醚、硬脂酸3,5-二-叔丁基-4-羟基苯基酯、己二酸二(3,5-二-叔丁基-4-羟基苯基)酯。
1.4生育酚,例如α-生育酚、β-生育酚、γ-生育酚、δ-生育酚及其混合物(维生素E)。
1.5羟基化硫代二苯醚,例如2,2’-硫代二(6-叔丁基-4-甲基苯酚)、2,2’-硫代二(4-辛基苯酚)、4,4’-硫代二(6-叔丁基-3-甲基苯酚)、4,4’-硫代二(6-叔丁基-2-甲基苯酚)、4,4’-硫代二(3,6-二-仲戊基苯酚)、4,4’-二(2,6-二甲基-4-羟基苯基)-二硫化物。
1.6亚烷基二酚,例如2,2’-亚甲基二(6-叔丁基-4-甲基苯酚)、2,2’-亚甲基二(6-叔丁基-4-乙基苯酚)、2,2’-亚甲基二[4-甲基-6-(α-甲基环己基)-苯酚]、2,2’-亚甲基二(4-甲基-6-环己基苯酚)、2,2’-亚甲基二(6-壬基-4-甲基苯酚)、2,2’-亚甲基二(4,6-二-叔丁基苯酚)、2,2’-亚乙基二(4,6-二-叔丁基苯酚)、2,2’-亚乙基二(6-叔丁基-4-异丁基苯酚)、2,2’-亚甲基二[6-(α-甲基苄基)-4-壬基苯酚]、2,2’-亚甲基二[6-(α,α-二甲基苄基)-4-壬基苯酚]、4,4’-亚甲基二(2,6-二-叔丁基苯酚)、4,4’-亚甲基二(6-叔丁基-2-甲基苯酚)、1,1-二(5-叔丁基-4-羟基-2-甲基苯基)丁烷、2,6-二(3-叔丁基-5-甲基-2-羟基苄基)-4-甲基苯酚、1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷、1,1-二(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基巯基丁烷、二[3,3-二(3’-叔丁基-4’-羟基苯基)丁酸]乙二醇酯、二(3-叔丁基-4-羟基-5-甲基-苯基)二环戊二烯、二[2-(3’-叔丁基-2’-羟基-5’-甲基苄基)-6-叔丁基-4-甲基苯基]对苯二甲酸酯、1,1-二-(3,5-二甲基-2-羟基苯基)丁烷、2,2-二(3,5-二-叔丁基-4-羟基苯基)丙烷、2,2-二-(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷基巯基丁烷、1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)戊烷。
1.7O-、N-和S-苄基化合物,例如3,5,3’,5’-四-叔丁基-4,4’-二羟基二苄基醚、十八烷基-4-羟基-3,5-二甲基苄基巯基乙酸酯、十三烷基-4-羟基-3,5-二-叔丁基苄基巯基乙酸酯、三(3,5-二-叔丁基-4-羟基苄基)胺、二(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二甲酸酯、二(3,5-二-叔丁基-4-羟基苄基)硫化物、异辛基-3,5-二-叔丁基-4-羟基苄基巯基乙酸酯。
1.8羟苄基化丙二酸酯,例如二(十八烷基)-2,2-二(3,5-二-叔丁基-2-羟基苄基)丙二酸酯、二-十八烷基-2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸酯、二-十二烷基巯基乙基-2,2-二(3,5-二-叔丁基-4-羟基苄基)丙二酸酯、二[4-(1,1,3,3-四甲基丁基)苯基]-2,2-二(3,5-二-叔丁基-4-羟基苄基)丙二酸酯。
1.9芳族羟基苄基化合物,例如1,3,5-三(3,5-二-叔丁基-4-羟基苄基)-2,4,6-三甲基苯、1,4-二(3,5-二-叔丁基-4-羟基苄基)-2,3,5,6-四甲基苯、2,4,6-三(3,5-二-叔丁基-4-羟基苄基)苯酚。
1.10三嗪化合物,例如2,4-二(辛基巯基)-6-(3,5-二-叔丁基-4-羟基苯氨基)-1,3,5-三嗪、2-辛基巯基-4,6-二(3,5-二-叔丁基-4-羟基苯氨基)-1,3,5-三嗪、2-辛基巯基-4,6-二(3,5-二-叔丁基-4-羟基苯氧基)-1,3,5-三嗪、2,4,6-三-(3,5-二-叔丁基-4-羟基苯氧基)-1,2,3-三嗪、1,3,5-三(3,5-二-叔丁基-4-羟基苄基)异氰脲酸酯、1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰脲酸酯、2,4,6-三(3,5-二-叔丁基-4-羟基苯乙基)-1,3,5-三嗪、1,3,5-三(3,5-二-叔丁基-4-羟基苯基丙酰基)-六氢-1,3,5-三嗪、1,3,5-三(3,5-环己基-4-羟基苄基)异氰脲酸酯。
1.11苄基膦酸酯,例如二甲基-2,5-二-叔丁基-4-羟基苄基膦酸酯、二乙基-3,5-二-叔丁基-4-羟基苄基膦酸酯、二(十八烷基)3,5-二-叔丁基-4-羟基苄基膦酸酯、二(十八烷基)-5-叔丁基-4-羟基-3-甲基苄基膦酸酯、3,5-二-叔丁基-4-羟基苄基膦酸单乙酯的钙盐。
1.12酰氨基酚,例如4-羟基月桂酰苯胺、4-羟基硬脂酰苯胺、N-(3,5-二-叔丁基-4-羟基苯基)氨基甲酸辛基酯。
1.13β-(3,5-二-叔丁基-4-羟基苯基)丙酸与以下一元醇或多元醇的酯:例如甲醇、乙醇、正辛醇、异辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-二(羟乙基)草酰二胺、3-硫杂十一醇(3-thiaundecanol)、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2,2,2]辛烷。
1.14β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与以下一元醇或多元醇的酯:例如甲醇、乙醇、正辛醇、异辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-二(羟乙基)草酰二胺、3-硫杂十一醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2,2,2]辛烷;3,9-二[2-{3-(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基)}-1,1-二甲基乙基]-2,4,8,10-四氧杂螺[5,5]-十一烷。
1.15β-(3,5-二环己基-4-羟基苯基)丙酸与以下一元醇或多元醇的酯:例如甲醇、乙醇、辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-二(羟乙基)草酰二胺、3-硫杂十一醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2,2,2]辛烷。
1.16.3,5-二-叔丁基-4-羟基苯基乙酸与以下一元醇或多元醇的酯:例如甲醇、乙醇、辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-二(羟乙基)草酰二胺、3-硫杂十一醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2,2,2]辛烷。
1.17.β-(3,5-二-叔丁基-4-羟基苯基)丙酸的酰胺,例如N,N’-二(3,5-二-叔丁基-4-羟基苯基丙酰基)六亚甲基二酰胺、N,N’-二(3,5-二-叔丁基-4-羟基苯基丙酰基)三亚甲基二酰胺、N,N’-二(3,5-二-叔丁基-4-羟基苯基丙酰基)酰肼、N,N’-二[2-(3-[3,5-二-叔丁基-4-羟基苯基]丙酰氧基)乙基]草酰二胺(NaugardXL-1,由Uniroyal提供)。
1.18抗坏血酸(维生素C)
1.19胺类抗氧化剂,例如N,N,N’-二-异丙基-对-苯二胺、N,N’-二-仲丁基-对-苯二胺、N,N’-二(1,4-二甲基戊基)-对-苯二胺、N,N’-二(1-乙基-3-甲基苯基)对-苯二胺、N,N’-二(1-甲基庚基)-对-苯二胺、N,N’-二环己基-对-苯二胺、N,N’-二苯基-对-苯二胺、N,N’-二(2-萘基)-对-苯二胺、N-异丙基-N’-苯基-对-苯二胺N-(1,3-二甲基丁基)-N’-苯基-对-苯二胺、N-(1-甲基庚基)-N’-苯基-对-苯二胺、N-环己基-N’-苯基-对-苯二胺、4-(对-甲苯氨磺酰基)二苯胺、N,N’-二甲基-N,N’-二-仲丁基-对-苯二胺、二苯胺、N-烯丙基二苯胺、4-异丙氧基二苯胺、N-苯基-1-萘胺、N-(4-叔辛基苯基)-1-萘胺、N-苯基-2-萘胺、例如p,p’-二-叔辛基二苯胺的辛基化二苯胺、4-正丁基氨基苯酚、4-丁酰氨基苯酚、4-壬酰氨基苯酚、4-十二烷酰氨基苯酚、4-十八烷酰氨基苯酚、二(4-甲氧基苯基)胺、2,6-二-叔丁基-4-二甲氨基甲基苯酚、2,4’-二氨基二苯基甲烷、4,4’-二氨基二苯基甲烷、N,N,N’,N’-四甲基-4,4’-二氨基二苯基甲烷、1,2-二[(2-甲基苯基)氨基]乙烷、1,2-二-(苯基氨基)丙烷、(邻-甲苯基)双胍、二[4-(1’,3’-二甲基丁基)苯基]胺、叔辛基化的N-苯基-1-萘胺、单烷基化和二烷基化的叔丁基/叔辛基二苯胺的混合物、单烷基化和二烷基化的壬基二苯胺的混合物、单烷基化和二烷基化的十二烷基二苯胺的混合物、单烷基化和二烷基化的异丙基/异己基二苯胺的混合物、单烷基化和二烷基化的叔丁基二苯胺的混合物、2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪、吩噻嗪、单烷基化和二烷基化的叔丁基/叔辛基吩噻嗪的混合物、单烷基化和二烷基化的叔辛基吩噻嗪的混合物、N-烯丙基吩噻嗪、N,N,N’,N’-四苯基-1,4-二氨基丁-2-烯、N,N-二(2,2,6,6-四甲基-哌啶-4-基-六亚甲基二胺、二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯、2,2,6,6-四甲基哌啶-4-酮、2,2,6,6-四甲基哌啶-4-醇。
2.紫外吸收剂与光稳定剂
2.12-(2’-羟基苯基)苯并三唑类,例如2-(2’-羟基-5’-甲基苯基)苯并三唑、2-(3’,5’-二-叔丁基-2’-羟基苯基)苯并三唑、2-(5’-叔丁基-2’-羟基苯基)苯并三唑、2-(2’-羟基-5’-(1,1,3,3-四甲基丁基)苯基)苯并三唑、2-(3’,5’-二-叔丁基-2’-羟基苯基)-5-氯苯并三唑、2-(3’-叔丁基-2’-羟基-5’-甲基苯基)-5-氯苯并三唑、2-(3’-仲丁基-5’-叔丁基-2’-羟基苯基)苯并三唑、2-(2’-羟基-4’-辛氧基苯基)苯并三唑、2-(3’,5’-二-叔戊基-2’-羟基苯基)苯并三唑、2-(3’,5’-二(α,α-二甲基苄基)-2’-羟基苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)-5-氯苯并三唑、2-(3’-叔丁基-5’-[2-(2-乙基己基氧基)羰基乙基]-2’-羟基苯基)-5-氯苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)-5-氯苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)苯并三唑、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)苯并三唑、2-(3’-十二烷基-2’-羟基-5’-甲基苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-异辛基氧基羰基乙基)苯基苯并三唑、2,2’-亚甲基二[4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基苯酚];2-[3’-叔丁基-5’-(2-甲氧基羰基乙基)-2’-羟基苯基]-2H-苯并三唑与聚乙二醇300的酯交换产物;[R-CH2CH2-COO-CH2CH2]2,其中R=3’-叔丁基-4’-羟基-5’-2H-苯并三唑-2-基苯酚、2-[2’-羟基-3’-(α,α-二甲基苄基)-5’-(1,1,3,3-四甲基丁基)苯基]苯并三唑;2-[2’-羟基-3’-(1,1,3,3-四甲基丁基)-5’-(α,α-二甲基苄基)苯基]苯并三唑。
2.22-羟基二苯甲酮类,例如4-羟基、4-甲氧基、4-辛氧基、4-癸氧基、4-十二烷氧基、4-苄氧基、4,2’,4’-三羟基和2’-羟基-4,4’-二甲氧基衍生物。
2.3取代与未取代的苯甲酸的酯,例如水杨酸4-叔丁基苯基酯、水杨酸苯酯、水杨酸辛基苯酯、二苯甲酰基间苯二酚、二(4-叔丁基苯甲酰基)间苯二酚、苯甲酰基间苯二酚、3,5-二-叔丁基-4-羟基苯甲酸2,4-二-叔丁基苯基酯、3,5-二-叔丁基-4-羟基苯甲酸十六烷基酯、3,5-二-叔丁基-4-羟基苯甲酸十八烷基酯、3,5-二-叔丁基-4-羟基苯甲酸2-甲基-4,6-二-叔丁基苯基酯。
2.4丙烯酸酯类,例如α-氰基-β,β-二苯基丙烯酸乙酯、α-氰基-β,β-二苯基丙烯酸异辛酯、α-甲酯基肉桂酸甲酯、α-氰基-β-甲基-对-甲氧基肉桂酸甲酯、α-氰基-β-甲基-对-甲氧基肉桂酸丁酯、α-甲酯基-对-甲氧基肉桂酸甲酯和N-(β-甲酯基-β-氰基乙烯基)-2-甲基二氢吲哚。
2.5镍化合物,例如:2,2’-硫代二[4-(1,1,3,3-四甲基丁基)苯酚]的镍络合物,例如1∶1或1∶2的络合物,有或没有其他配体如正丁基胺、三乙醇胺或N-环己基二乙醇胺,二丁基二硫代氨基甲酸镍,单烷基酯的镍盐,如4-羟基-3,5-二-叔丁基苄基膦酸甲酯或4-羟基-3,5-二-叔丁基苄基膦酸乙酯,酮肟的镍络合物,如2-羟基-4-甲基苯基十一烷基酮肟,1-苯基-4-十二烷酰基-5-羟基吡唑的镍络合物,有或没有另外的配体。
2.6位阻胺类,例如二(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、二(2,2,6,6-四甲基-4-哌啶基)琥珀酸酯、二(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯、二(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯、正丁基-3,5-二-叔丁基-4-羟基苄基丙二酸二(1,2,2,6,6-五甲基-4-哌啶基)酯、1-(2-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合物、N,N’-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-叔辛氨基-2,6-二氯-1,3,5-三嗪的链状或环状缩合物、三(2,2,6,6-四甲基-4-哌啶基)次氮基三乙酸酯、四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四甲酸酯、1,1’-(1,2-亚乙基)-二(3,3,5,5-四甲基哌嗪酮)、4-苯甲酰基-2,2,6,6-四甲基哌啶、4-十八烷基氧基(stearyloxy)-2,2,6,6-四甲基哌啶、二(1,2,2,6,6-五甲基哌啶基)-2-正丁基-2-(2-羟基-3,5-二-叔丁基苄基)丙二酸酯、3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮、二(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯、二(1-辛氧基-2,2,6,6-四甲基哌啶基)琥珀酸酯、N,N’-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-吗啉代-2,6-二氯-1,3,5-三嗪的链状或环状缩合物、2-氯-4,6-二(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙氨基)乙烷的缩合物、2-氯-4,6-二(4-正丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙氨基)乙烷的缩合物、8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮、3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮、3-十二烷基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮、5-(2-乙基己酰基)-氧基甲基-3,3,5-三甲基-2-吗啉酮、1-(2-羟基-2-甲基丙氧基)-4-十八烷酰氧基-2,2,6,6-四甲基哌啶、1,3,5-三(N-环己基N-(2,2,6,6-四甲基哌嗪-3-酮-4-基)氨基)-S-三嗪、1,3,5-三(N-环己基N-(1,2,2,6,6-五甲基哌嗪-3-酮-4-基)氨基)-S-三嗪、2,4-二[(1-环己基氧基-2,2,6,6-哌啶-4-基)丁氨基]-6-氯-S-三嗪与N,N’-二(3-氨基丙基)乙二胺的反应产物、4-十六烷基氧基-和4-十八烷基氧基-2,2,6,6-四甲基哌啶的混合物、N,N’-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-环己基氨基-2,6-二氯-1,3,5-三嗪的缩合物、1,2-二(3-氨基丙氨基)乙烷和2,4,6-三氯-1,3,5-三嗪以及4-丁基氨基-2,2,6,6-四甲基哌啶(CAS登录号[136504-96-6])的缩合物;1,6-己二胺和2,4,6-三氯-1,3,5-三嗪以及N,N-二丁基胺和4-丁基氨基-2,2,6,6-四甲基哌啶(CAS登录号[192268-64-7])的缩合物;N-(2,2,6,6-四甲基-4-哌啶基)-正十二烷基琥珀酰亚胺;N-(1,2,2,6,6-五甲基-4-哌啶基)-正十二烷基琥珀酰亚胺;2-十一烷基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧代-螺[4.5]癸烷;5-(2-乙基己酰基)氧基甲基-3,3,5-三甲基-2-吗啉酮;7,7,9,9-四甲基-2-环十一烷基-1-氧杂-3,8-二氮杂-4-氧代螺-[4.5]癸烷和表氯醇的反应产物、1,1-二(1,2,2,6,6-五甲基-4-哌啶基氧基羰基)-2-(4-甲氧基苯基)-乙烯、N,N’-二甲酰基-N,N’-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺、4-甲氧基亚甲基丙二酸和1,2,2,6,6-五甲基-4-羟基哌啶的二酯、聚[甲基丙基-3-氧基-4-(2,2,6,6-四甲基-4-哌啶基)]硅氧烷、马来酸酐-α-烯烃共聚物和2,2,6,6-四甲基-4-氨基哌啶或1,2,2,6,6-五甲基-4-氨基哌啶的反应产物。
2.7草酰胺类,例如4,4’-二辛氧基N,N’-草酰二苯胺、2,2’-二乙氧基N,N’-草酰二苯胺、2,2’-二辛氧基-5,5’-二-叔丁氧基N,N’-草酰二苯胺、2,2’-二十二烷氧基-5,5’-二-叔丁氧基N,N’-草酰二苯胺、2-乙氧基-2’-乙基N,N’-草酰二苯胺、N,N’-二(3-二甲氨基丙基)草酰胺、2-乙氧基-5-叔丁基-2’-乙氧基N,N’-草酰二苯胺和它与2-乙氧基-2’-乙基-5,4’-二-叔丁氧基N,N’-草酰二苯胺的混合物、邻-和对-甲氧基-二取代的N,N’-草酰二苯胺的混合物以及邻-和对-乙氧基-二取代的N,N’-草酰二苯胺的混合物。
2.82-(2-羟基苯基)-1,3,5-三嗪类,例如2,4,6-三(2-羟基-4-辛氧基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2,4-二(2-羟基-4-丙氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-二(4-甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-三癸氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-丁氧基丙氧基)苯基]-4,6-二(2,4-二甲基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-辛氧基丙氧基)苯基]4,6-二(2,4-二甲基)-1,3,5-三嗪、2-[4-(十二烷氧基/十三烷氧基-2-羟基丙氧基)-2-羟基苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-十二烷氧基丙氧基)苯基]-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-己氧基)苯基-4,6-二苯基-1,3,5-三嗪、2-(2-羟基-4-甲氧基苯基)-4,6-二苯基-1,3,5-三嗪、2,4,6-三[2-羟基-4-(3-丁氧基-2-羟基丙氧基)苯基]-1,3,5-三嗪、2-(2-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪、2-{2-羟基-4-[3-(2-乙基己基-1-氧基)-2-羟基丙基氧基]苯基}-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪。
3.金属减活化剂,例如N,N’-二苯基草酰胺、N-水杨醛基-N’-水杨酰基肼、N,N’-二(水杨酰基)肼、N,N’-二(3,5-二-叔丁基-4-羟基苯基丙酰基)肼、3-水杨酰氨基-1,2,4-三唑、二(苯亚甲基)草酰二肼、N,N’-草酰二苯胺、间苯二酰二肼、癸二酰基二苯基酰肼、N,N’-二乙酰基己二酰二肼、N,N’-二(水杨酰基)草酰二肼、N,N’-二(水杨酰基)硫代丙酰二肼。
4.亚磷酸酯类和亚膦酸酯类,例如亚磷酸三苯酯、亚磷酸二苯基烷基酯、亚磷酸苯基二烷基酯、亚磷酸三(壬基苯基)酯、亚磷酸三月桂基酯、亚磷酸三(十八烷基)酯、二亚磷酸二(十八烷基)季戊四醇酯、亚磷酸三(2,4-二-叔丁基苯基)酯、二亚磷酸二异癸基季戊四醇酯、二亚磷酸二(2,4-二-叔丁基苯基)季戊四醇酯、二亚磷酸二(2,4-二-枯基苯基)季戊四醇酯、二亚磷酸二(2,6-二-叔丁基-4-甲基苯基)季戊四醇酯、二亚磷酸二异癸氧基季戊四醇酯、二亚磷酸二(2,4-二-叔丁基-6-甲基苯基)-季戊四醇酯、二亚磷酸二(2,4,6-三(叔丁基苯基)季戊四醇酯、三亚磷酸三(十八烷基)山梨糖醇酯、二亚膦酸四(2,4-二-叔丁基苯基)4,4’-二亚苯基酯、6-异辛基氧基-2,4,8,10-四-叔丁基-12H-二苯并[d,g]-1,3,2-二氧杂磷杂八环(dioxaphosphocin)、亚磷酸二(2,4-二-叔丁基-6-甲基苯基)甲基酯、亚磷酸二(2,4-二-叔丁基-6-甲基苯基)乙基酯、6-氟-2,4,8,10-四-叔丁基-12-甲基-二苯并[d,g]-1,3,2-二氧杂磷杂八环、2,2’,2”-次氮基[三乙基三(3,3’,5,5’-四-叔丁基-1,1’-二苯基-2,2’-二基)亚磷酸酯]、2-乙基己基(3,3’,5,5’-四-叔丁基-1,1’-二苯基-2,2’-二基)亚磷酸酯、5-丁基-5-乙基-2-(2,4,6-三-叔丁基苯氧基)-1,3,2-二氧杂膦杂环丙烷。
特别优选以下亚磷酸酯类化合物:
亚磷酸三(2,4-二-叔丁基苯基)酯(Irgafos168,Ciba-Geigy)、亚磷酸三(壬基苯基)酯、
5.羟胺类,例如N,N-二苄基羟胺、N,N-二乙基羟胺、N,N-二辛基羟胺、N,N-二月桂基羟胺、N,N-二(十四烷基)羟胺、N,N-二(十六烷基)羟胺、N,N-二(十八烷基)羟胺、N-十六烷基-N-十八烷基羟胺、N-十七烷基-N-十八烷基羟胺、由氢化牛脂胺(tallow amine)衍生而来的N,N-二烷基羟胺。
6硝酮类,例如N-苄基-α-苯基硝酮、N-乙基-α-甲基硝酮、N-辛基-α-庚基硝酮、N-月桂基-α-十一烷基硝酮、N-十四烷基-α-十三烷基硝酮、N-十六烷基-α-十五烷基硝酮、N-十八烷基-α-十七烷基硝酮、N-十六烷基-α-十七烷基硝酮、N-十八烷基-α-十五烷基硝酮、N-十七烷基-α-十七烷基硝酮、N-十八烷基-α-十六烷基硝酮、由衍生自氢化牛脂胺的N,N-二烷基羟胺衍生的硝酮。
7.硫代增效剂,例如硫代二丙酸二月桂基酯或硫代二丙酸二(十八烷基)酯。
8.过氧化物净化剂,例如β-硫代二丙酸的酯(例如月桂基酯、十八烷基酯、十四烷基酯或十三烷基酯)、巯基苯并咪唑或2-巯基苯并咪唑的锌盐、二丁基二硫代氨基甲酸锌、二(十八烷基)二硫化物、四(β-十二烷基巯基)丙酸季戊四醇酯。
9.聚酰胺稳定剂,例如与碘化物和/或磷化合物结合的铜盐以及二价锰盐。
10.碱性共稳定剂,例如三聚氰胺、聚乙烯吡咯烷酮、双氰胺、氰脲酸三烯丙基酯、脲衍生物、肼衍生物、胺、聚酰胺、聚氨酯、高级脂肪酸的碱金属盐和碱土金属盐,如硬脂酸钙、硬脂酸锌、山嵛酸镁、硬脂酸镁、蓖麻油酸钠和棕榈酸钾、焦儿茶酸(pyrocatecholate)锑或焦儿茶酸锌。
11.成核剂,例如无机物质:如滑石粉,金属氧化物(如二氧化钛或氧化镁),磷酸盐、碳酸盐或硫酸盐(优选碱土金属盐);有机化合物:如一元羧酸或多元羧酸及其盐,如4-叔丁基苯甲酸、己二酸、二苯基乙酸、琥珀酸钠或苯甲酸钠;高分子化合物:如离子共聚物(离子交联聚合物)。尤其优选1,3:2,4-二(3’,4’-二甲基亚苄基)山梨糖醇、1,3:2,4-二(对甲基二亚苄基)山梨糖醇和1,3:2,4-二(亚苄基)山梨糖醇。
12.填充剂和增强剂,例如碳酸钙、硅酸盐、玻璃纤维、玻璃珠、石棉、滑石粉、高岭土、云母、硫酸钡、金属氧化物和氢氧化物、炭黑、石墨、木粉和其它天然产物的粉末或纤维、合成纤维。
13.其它添加剂,例如增塑剂、润滑剂、乳化剂、颜料、流变添加剂、催化剂、流动控制剂、荧光增白剂、防火剂、抗静电剂和发泡剂。
14.苯并呋喃酮和吲哚酮,例如在以下专利中包括的那些化合物:U.S.4,325,863;U.S.4,338,244;U.S.5,175,312;U.S.5,216,052;U.S.5,252,643;DE-A-4316611;DE-A-4316622;DE-A-4316876;EP-A-0589839或EP-A-0591102,或3-[4-(2-乙酰氧基乙氧基)-苯基]-5,7-二-叔丁基-苯并呋喃-2-酮、5,7-二-叔丁基-3-[4-(2-硬脂酰氧基乙氧基)苯基]苯并呋喃-2-酮、3,3’-二[5,7-二-叔丁基-3-(4-[2-羟基乙氧基]苯基)苯并呋喃-2-酮]、5,7-二-叔丁基-3-(4-乙氧基苯基)苯并呋喃-2-酮、3-(4-乙酰氧基-3,5-二甲基苯基)-5,7-二-叔丁基-苯并呋喃-2-酮、3-(3,5-二甲基-4-新戊酰氧基苯基)-5,7-二-叔丁基-苯并呋喃-2-酮、3-(3,4-二甲基苯基)-5,7-二-叔丁基-苯并呋喃-2-酮、3-(2,3-二甲基苯基)-5,7-二-叔丁基-苯并呋喃-2-酮。
本发明优选的组合物包含一种或多种选自以下组分的其它添加剂:颜料、染料、填充剂、流平剂、分散剂、增塑剂、硫化活化剂、硫化促进剂、硫化剂、电荷控制剂(charge control agents)、增粘剂、光稳定剂或抗氧化剂(如酚类抗氧化剂(所列第1.1项至1.18项)或胺类抗氧化剂(所列第1.19项))、有机亚磷酸酯或亚膦酸酯类(所列第4项)和/或硫代增效剂(所列第7项)。
这些其它添加剂加入时的浓度为0.01%-10%,基于需要稳定的弹性体的总重量计算。
成分b)和(如果需要)其它添加剂用已知方法加入到弹性体中,例如在有撞击器的密闭式混机(Banbury)中,在研磨辊上或在混合挤压机中混合过程中,在成形或硫化或其它步骤之前或过程中,将已溶解或已分散的成分b)施用到弹性体上,如果需要接下来通过蒸发除去溶剂。加入到需要稳定的弹性体时,成分b)和(如果需要)其它添加剂也可为包含这些例如2.5%-25%重量浓度的母料形式。
成分b)和(如果需要)其它添加剂也可在合成弹性体的聚合反应之前、过程中或者交联之前加入,即如果需要,最好在生胶中作为一线(first-level)稳定剂加入,其也可包含其它组分,例如作为填充剂和/或增量油的炭黑。
式I化合物在加工条件下(化合、混合、硫化等)被化学键合(接枝)到聚合物链上。式I化合物抗提取,即它们在基体经过充分提取后继续提供良好的保护作用。这类弹性体经迁移或提取而损失的式I化合物极少。因此,本发明的主题包含一种将式I化合物接枝到聚合物上的方法,所述方法包括以下步骤:在聚合物的软化点以上加热、优选在聚合物加工装置中加热聚合物和至少一种式I化合物的混合物,并使它们相互反应。接枝优选温度范围为120℃-200℃,例如140℃-180℃,尤其为150℃-170℃。
经式I化合物稳定后的弹性体的光泽也明显地改善且令人满意。这意味着按照本发明,在暴露于臭氧后,经稳定了的弹性体表面的光泽显著地好于未经稳定的弹性体或按照现有技术稳定的弹性体表面的光泽。更为有利的是,本发明式I化合物的使用明显减少或消除了接触变色(染色)。
当成分b)和(如果需要)其它添加剂被加入到待稳定的弹性体时,它们可以为纯物质的形式或被封入蜡、油或聚合物中。
成分b)和(如果需要)其它添加剂也可以被喷到待稳定的弹性体上。它们能稀释其它添加剂(例如以上给出的常规添加剂)或者这些添加剂的融熔物,且它们可与这些添加剂一起被喷到待稳定的弹性体上。
结果被稳定的弹性体可以以广泛的形式使用,例如带状物、成型组合物、表面(profiles)、传送带或气压轮胎。
本发明还提供一种稳定弹性体的方法,所述方法用于防止由氧化、热、动力学、光和/或臭氧引发的降解,所述方法包括将至少一种成分b)加入或施用于这些弹性体上。
本发明还提供一种防止基体与弹性体接触所致接触变色的方法,所述方法包括将至少一种成分b)加入或施用于这些弹性体上。
本发明再一个实施方案为成分b)作为弹性体稳定剂的用途,所述用途用于防止由氧化、热、动力学、光和/或臭氧引发的降解。
本发明再一个实施方案为成分b)作为弹性体稳定剂的用途,所述用途用于防止基体与弹性体接触所致的接触变色。
对于以上所列的方法和用途,优选的式I化合物[成分b)]与那些用于本发明组合物的化合物相同。
以下实施例进一步举例说明本发明。以份或百分率表示的数据基于重量计。室温代表20-25℃的温度范围。MS(CI)表示质谱(化学电离)。
实施例1:式1B化合物的制备
式1A的原料硫醚按照WO-A-02/42262、实施例3制备。将4.7g(0.01mol)的该硫醚1A和2g(0.018mol)的尿素-H2O2-加合物(30%H2O2)的8ml乙醇溶液在40℃下搅拌6小时。用焦硫酸钠(Na2S2O5)溶液洗涤有机相除去多余的过氧化氢后,蒸馏除去溶剂。得到题述亚砜1B化合物(收率100%),为棕色树脂。MS(CI)485(MH+)。
实施例2:由式2A化合物制备式2B化合物
按照WO-A-02/42262的实施例1-15描述的方法,在20℃、搅拌下,用3.0mmol的叔十二烷基硫醇处理3.0mmol N-(1,3-二甲基丁基)-N’-苯基-对-醌二亚胺的乙醇(25ml)溶液。按WO-A-02/42262的实施例3的类似方法分离出中间体2A,为棕色油状物,收率59%,MS(CI)469(MH+)。随后按上述实施例1的方法进行氧化和后处理,得到题述亚砜2B化合物(理论量的74%),为棕色油状物,MS(CI):485(MH+)。
实施例3:由式3A化合物制备式3B化合物
按照WO-A-02/42262中实施例1-15所述方法,将3.0mmol的N-(1,3-二甲基丁基)-N’-苯基-对-醌二亚胺与等摩尔量的硫醇HS-CH2CH2COO-异辛基反应。按WO-A-02/42262中实施例3的类似方法分离出中间体3A,为棕色油状物,收率31%,MS(CI)484(M+)。随后按上述实施例1的方法进行氧化和后处理,得到题述亚砜3B化合物(理论量的95%),为棕色油状物,MS(CI):501(MH+)。
实施例4:由式4A化合物制备式4B化合物
按照WO-A-02/42262中实施例1-15所述方法,将3.0mmol的N-(1,3-二甲基丁基)-N’-苯基-对-醌二亚胺与等摩尔量的叔壬基硫醇反应。按WO-A-02/42262中实施例3的类似方法分离出中间体4A,为棕色油状物,收率39%,MS(EI))426(M+)。随后按上述实施例1的方法进行氧化和后处理,得到题述产物4B(理论量的10%),为棕色油状物,MS(CI):443(MH+)。
实施例5:由式5A化合物制备式5B化合物
按照WO-A-02/42262中实施例1-15所述方法,将3.0mmol的N’-(1,3-二甲基丁基)-N’-苯基-对-醌二亚胺与等摩尔量的苄基硫醇反应。按WO-A02/42262中实施例3的类似方法分离出中间体5A,为棕色粘稠油状物,收率51%,MS(EI)390(M+)。随后按上述实施例1所述方法进行氧化和后处理,得到题述产物5B(理论量的61%),为绿色粉末,m.p.60℃,MS(CI)407(MH+)。
实施例6:由式6A化合物制备式6B化合物
按照WO-A-02/42262中实施例1-15所述方法,将3.0mmol的N-异丙基-N’-苯基-对-醌二亚胺与等摩尔量的正十二烷基硫醇反应。按WO-A-02/42262中实施例3的类似方法分离出中间体6A,为棕色油状物,收率75%,MS(CI)427(MH+)。随后按上述实施例1的方法进行氧化和后处理,得到题述产物6B(理论量的80%),为无色结晶,m.p.89℃,MS(CI)443(MH+)。
实施例7:由式7A化合物制备式7B化合物
按照WO-A-02/42262中实施例1-5所述方法,将3.0mmol的N-异丙基-N’-苯基-对-醌二亚胺与等摩尔量的正十二烷基硫醇反应。按WO-A-02/42262中实施例3的类似方法分离出中间体7A,为棕色油状物,收率89%,MS(EI)442(M+)。随后按上述实施例1的方法进行氧化和后处理,得到题述产物7B(理论量的95%),为棕色油状物,MS(CI)459(MH+)。
实施例8:由式8A化合物制备式8B化合物
按照WO-A-02/42262中实施例1-15所述方法,将3.0mmol的N-环己基-N’-苯基-对-醌二亚胺与等摩尔量的正十二烷基硫醇反应。按WO-A-02/42262中实施例3的类似方法分离出中间体8A,为棕色油状物,收率56%,MS(EI)466(M+)。随后按上述实施例1的方法进行氧化和后处理,得到题述产物8B(理论量的84%),为无色结晶,m.p.112℃,MS(CI)483(MH+)。
实施例9:由式9A化合物制备式9B化合物
按照WO-A-02/42262中实施例1-15所述方法,将3.0mmol的N-环己基N’-苯基-对-醌二亚胺与等摩尔量的硫醇HS-CH2CH2COO-异辛基反应。按WO-A-02/42262中实施例3的类似方法分离出中间体9A,为棕色油状物,收率54%,MS(EI)482(M+)。随后按上述实施例1的方法进行氧化和后处理,得到题述产物9B(理论量的100%),为棕色油状物,MS(EI)498(M+)。
实施例10:由10A化合物制备式10B化合物
按照WO-A-02/42262中实施例1-15所述方法,将3.0mmol的N-(2-辛基)-N’-苯基-对-醌二亚胺与等摩尔量的正十二烷基硫醇反应。按WO-A-02/42262中实施例3的类似方法分离出中间体10A,为棕色油状物,收率72%,MS(EI)496(M+)。随后按上述实施例1的方法进行氧化和后处理,得到题述产物10B(理论量的100%),为棕色油状物,MS(CI)513(MH+)。
实施例11:由11A化合物制备式11B化合物
按照WO-A-02/42262中实施例1-15所述方法,将3.0mmol的N-(2-辛基)-N’-苯基-对-醌二亚胺与等摩尔量的叔十二烷基硫醇反应。按WO-A-02/42262中实施例3的类似方法分离出中间体11A,为棕色油状物,收率57%,MS(EI)496(M+)。随后按上述实施例1的方法进行氧化和后处理,得到题述产物11B(理论量的24%),为棕色油状物,MS(CI)513(MH+)。
实施例12:由12A化合物制备式12B化合物
按照WO-A-02/42262中实施例1-15所述方法,将3.0mmol的N-(2-辛基)-N’-苯基-对-醌二亚胺与等摩尔量的硫醇HS-CH2CH2COO-异辛基反应。按WO-A-02/42262中实施例3的类似方法分离出中间体12A,为棕色油状物,收率54%,MS(CI)513(MH+)。随后按上述实施例1的方法进行氧化和后处理,得到题述产物12B(理论量的100%),为棕色油状物,MS(CI)529(MH+)。
实施例13:黑色硫化橡胶的稳定
40.0重量份的Cariflex1220[聚丁二烯,SHELL]在混炼机上于60℃与60.0重量份天然橡胶以及55.0重量份炭黑(N330)、6.0重量份Ingralen 450(RTM)[增量油]、5.0重量份氧化锌[硫化活化剂]、2.0重量份十八烷酸[硫化活化剂]、0.2重量份IRGANOX 1520(RTM)[加工稳定剂,Ciba Specialty Chemicals]、2.0重量份硫[硫化剂]、0.6重量份VulkacitMOZ(RTM)[硫化促进剂,BAYER]和1.5重量份根据表1、2和3测试的稳定剂加工形成均一混合物,硫化系统[硫和Vulkacit MOZ(RTM)]直至混合过程结束时才加入。该混合物在电热压设备中于150℃硫化至流变仪曲线上的T95,形成2mm厚、21cm长和8.0cm宽的弹性体薄片。将部分2mm橡胶薄片放置在白色垫板上并于循环空气室中50℃下存放5天。然后用肉眼观察评价其接触面或其边缘的接触变色(染色):0=无变色(或对照的变色,其中无AO存在),和5=最大程度的变色。结果如表1总结。
表1:
实施例 | 稳定剂 | 染色(4周) |
13ab) | 1B | 0 |
13bb) | 2B | 0 |
13cb) | 3B | 0 |
13db) | 4B | 0 |
13eb) | 6B | 0 |
13fb) | 8B | 0 |
13gb) | 10B | 0 |
13hb) | 11B | 0 |
13ia) | Vulkanox4020c) | 5 |
13ka) | Vulkanox4010d) | >3 |
13la) | UOP688e) | >2 |
13ma) | Flexzone6Hf) | >4 |
a)比较实施例。
b)本发明实施例。
c)Vulkanox 4020(RTM[Bayer]为式A的4-(1,3-二甲基丁基)氨基二苯胺。
d)Vulkanox 4010(RTM)[Bayer]为式B的4-(2-丙氨基)二苯胺。
e)UOP 688(RTM)[UOP]为式C的4-(2-辛氨基)二苯胺。
f)Flexzone 6H(RTM)[Flexsys]为式D的4-环己基氨基二苯胺。
接枝速率的测定:为了检测本发明化合物的抗提取性,将2mm板在Soxhlet提取器中用丙酮处理72小时。考虑到混合物其它成分的氮可提取并对提取稳定,添加剂不能提取的部分用氮分析法测定。结果如表2总结。
表2:
实施例 | 稳定剂 | 不可提取的添加剂g)[%] |
13aa) | 1A | 0 |
13bb) | 1B | 5 |
13ca) | 2A | 0 |
13db) | 2B | 47 |
13ea) | 3A | 0 |
13fb) | 3B | 32 |
13ga) | 4A | 0 |
13hb) | 4B | 48 |
13ia) | 6A | 0 |
13jb) | 6B | 18 |
13ka) | 8A | 0 |
13lb) | 8B | 11 |
13mb) | 11B | 48 |
13na) | Vulkanox4020c) | 0 |
a)比较实施例
b)本发明实施例
c)见表1下面脚注
g)用丙酮Soxhlet提取后(72小时),进行氮分析法
提取样品的氧化保护:为确定所接枝的添加剂的效果,提取的样品在多室烘箱(DIN 53508)中进行热空气老化。用ISO S2哑铃(dumb-bells)(DIN 53504)通过抗拉试验测定添加剂的抗氧化作用。抗拉强度越高,保护作用就越好。结果如表3总结。
表3:
实施例 | 稳定剂 | 80℃烘箱老化2周后提取样品的抗拉强度[MPa] |
13aa) | 1A | 4.9 |
13bb) | 1B | 6.4 |
13ca) | 2A | 6.2 |
13db) | 2B | 8.3 |
13ea) | 3A | 5.3 |
13fb) | 3B | 8.9 |
13ga) | 4A | 6.1 |
13hb) | 4B | 10.8 |
13ib) | 5B | 6.6 |
13ja) | 8A | 5.4 |
13kb) | 8B | 7.9 |
13la) | Vulkanox4020c) | 5.3 |
脚注a)、b)和c)的解释见表1下面。
Claims (10)
1.一种式I化合物,
其中
R1为C1-C18烷基、C5-C12-环烷基、苯基、苄基或烯丙基;
n为1或2;
如果n为1,则R2为C4-C18烷基、C5-C12环烷基、芳基或杂芳基、苄基、烯丙基、(CH2)mCOOR3或为(CH2)mCN;
如果n为2,则R2为-S-(CH2)p-S或-S-(CH2)2-[O-(CH2)2]m-S-;
R3为C1-C18烷基、苄基、烯丙基;
m为1或2;且
p为2-12的数。
2.权利要求1的式I化合物,其中
R1为C2-C8-烷基、环己基、苯基、苄基或烯丙基;
如果n为1,则R2为C4-C18烷基、环己基、苄基、苯基、(CH2)2COOR3或为(CH2)2CN;
如果n为2,则R2为-S-(CH2)p-S或-S-(CH2)2-[O-(CH2)2]m-S-;
R3为C1-C18烷基;且
p为2-6的数。
3.一种组合物,所述组合物包含
a)易受氧化、热、动力学、光和/或臭氧引发降解的天然存在或合成弹性体,和
b)至少一种、特别是基于组分a)的重量计用量为0.05%-10%的权利要求1的式I化合物为稳定剂。
4.权利要求3的组合物,其中组分a)为天然或合成橡胶或由它们制备的硫化橡胶。
5.权利要求4的组合物,其中组分a)为聚二烯硫化橡胶、含卤素聚二烯硫化橡胶、聚二烯共聚物硫化橡胶或乙烯-丙烯三聚物硫化橡胶。
6.权利要求3的组合物,所述组合物还包含一种或一种以上的选自以下的组分:颜料、染料、填充剂、流平剂、分散剂、增塑剂、硫化活化剂、硫化促进剂、硫化剂、电荷控制剂、增粘剂、抗氧化剂、阻燃剂、紫外光吸收剂和光稳定剂,特别是酚抗氧化剂、胺抗氧化剂、有机亚磷酸酯或亚膦酸酯和/或硫代增效剂。
8.一种将权利要求1的式I化合物接枝到弹性体上的方法,所述方法包括在高于所述弹性体的软化点加热弹性体和至少一种上述权利要求1的式I化合物的混合物,并使它们相互反应。
9.权利要求1的式I化合物作为弹性体稳定剂的用途,所述用途用于防止氧化、热、动力学、光和/或臭氧引发的弹性体降解和/或基体与所述弹性体接触所致的接触变色。
10.一种用于稳定弹性体以防止氧化、热、动力学、光和/或臭氧引发的降解和防止基体与所述弹性体接触所致接触变色的方法,所述方法包括将至少一种权利要求1的式I化合物加入或施用于这些弹性体中。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP02405864 | 2002-10-07 | ||
EP02405864.6 | 2002-10-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1688647A true CN1688647A (zh) | 2005-10-26 |
Family
ID=32050145
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNA038238233A Pending CN1688647A (zh) | 2002-10-07 | 2003-09-30 | 用于硫化橡胶的可接枝的4-氨基-3-亚磺酰基-取代的二苯胺稳定剂 |
Country Status (11)
Country | Link |
---|---|
US (1) | US20060041045A1 (zh) |
EP (1) | EP1549710A1 (zh) |
JP (1) | JP2006502197A (zh) |
KR (1) | KR20050052503A (zh) |
CN (1) | CN1688647A (zh) |
AU (1) | AU2003271662A1 (zh) |
BR (1) | BR0315097A (zh) |
CA (1) | CA2494341A1 (zh) |
MX (1) | MXPA05002089A (zh) |
RU (1) | RU2005114372A (zh) |
WO (1) | WO2004031287A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103285921A (zh) * | 2013-06-09 | 2013-09-11 | 东南大学 | 硅橡胶固载化有机催化剂及其制备方法和用途 |
CN106674591A (zh) * | 2016-12-07 | 2017-05-17 | 绍兴瑞康生物科技有限公司 | 一种含硫醚长效抗高温抗氧化稳定剂及其应用 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1934278B1 (en) * | 2005-10-11 | 2013-12-11 | Basf Se | Non-staining antidegradants for vulcanized elastomers |
US7846884B2 (en) | 2005-11-29 | 2010-12-07 | Chemtura Corporation | Lubricating oil compositions |
JP5811845B2 (ja) * | 2009-11-13 | 2015-11-11 | 日本ゼオン株式会社 | ジフェニルアミン系化合物、及び老化防止剤、並びにポリマー組成物 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1228135B1 (en) * | 1999-10-18 | 2004-04-14 | Ciba SC Holding AG | Stabilizers and antiozonants for elastomers |
US20020132888A1 (en) * | 2000-11-21 | 2002-09-19 | Maender Otto William | Alkylthio-and aryl(heteroyl)thio-substituted p-phenylenediamines, their manufacture and their use in rubber |
UA76141C2 (en) * | 2001-04-06 | 2006-07-17 | Ciba Sc Holding Ag | Sulfoxides or sulfones grafted with polymers, use thereof, intermediate compounds for producing thereof, a method for grafting and a method for stabilizing polymer |
-
2003
- 2003-09-30 CN CNA038238233A patent/CN1688647A/zh active Pending
- 2003-09-30 WO PCT/EP2003/010836 patent/WO2004031287A1/en not_active Application Discontinuation
- 2003-09-30 US US10/529,414 patent/US20060041045A1/en not_active Abandoned
- 2003-09-30 JP JP2004540751A patent/JP2006502197A/ja active Pending
- 2003-09-30 RU RU2005114372/04A patent/RU2005114372A/ru not_active Application Discontinuation
- 2003-09-30 MX MXPA05002089A patent/MXPA05002089A/es not_active Application Discontinuation
- 2003-09-30 BR BR0315097-6A patent/BR0315097A/pt active Pending
- 2003-09-30 AU AU2003271662A patent/AU2003271662A1/en not_active Abandoned
- 2003-09-30 KR KR1020057004553A patent/KR20050052503A/ko not_active Application Discontinuation
- 2003-09-30 EP EP03753481A patent/EP1549710A1/en not_active Withdrawn
- 2003-09-30 CA CA002494341A patent/CA2494341A1/en not_active Abandoned
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103285921A (zh) * | 2013-06-09 | 2013-09-11 | 东南大学 | 硅橡胶固载化有机催化剂及其制备方法和用途 |
CN106674591A (zh) * | 2016-12-07 | 2017-05-17 | 绍兴瑞康生物科技有限公司 | 一种含硫醚长效抗高温抗氧化稳定剂及其应用 |
CN106674591B (zh) * | 2016-12-07 | 2019-02-01 | 绍兴瑞康生物科技有限公司 | 一种含硫醚长效抗高温抗氧化稳定剂及其应用 |
Also Published As
Publication number | Publication date |
---|---|
AU2003271662A1 (en) | 2004-04-23 |
MXPA05002089A (es) | 2005-06-06 |
BR0315097A (pt) | 2005-08-16 |
US20060041045A1 (en) | 2006-02-23 |
KR20050052503A (ko) | 2005-06-02 |
JP2006502197A (ja) | 2006-01-19 |
EP1549710A1 (en) | 2005-07-06 |
WO2004031287A1 (en) | 2004-04-15 |
RU2005114372A (ru) | 2006-01-20 |
CA2494341A1 (en) | 2004-04-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101641403A (zh) | 用于橡胶配混的加工稳定剂 | |
CN100436523C (zh) | 填料和弹性体之间的偶联剂 | |
CN1237058C (zh) | 合成聚合物的稳定方法 | |
JP4883178B2 (ja) | 新規ジウレタン化合物、その製造法およびそれを含有するアクリルゴム組成物 | |
JP4598148B2 (ja) | スルフェンアミド、このスルフェンアミドを含むゴム用加硫促進剤およびその製造方法 | |
CN1172980C (zh) | 用于高弹体的稳定剂和防臭氧剂 | |
CN1132765A (zh) | 一种橡胶组合物及使用该橡胶组合物的硫化粘合方法 | |
CN101679711A (zh) | 丙烯酸橡胶组合物以及其硫化橡胶及其用途 | |
CN1505659A (zh) | 丙烯酸橡胶组合物和硫化橡胶 | |
CN101056926A (zh) | 具有改善抗褪色性抗微生物聚合物组合物 | |
DK171765B1 (da) | Arylendiaminosubstituerede triaziner, fremgangsmåde til fremstilling heraf og gummi med indhold heraf | |
JP2625213B2 (ja) | トリアジン化合物および耐崩壊性組成物 | |
CN1087287C (zh) | 包含苯酚基团和芳香胺基团的抗氧化剂 | |
US3770826A (en) | N,n'-thio-bis-carbamic acid amides | |
CN1688647A (zh) | 用于硫化橡胶的可接枝的4-氨基-3-亚磺酰基-取代的二苯胺稳定剂 | |
CN1074776C (zh) | 2,4-二甲基-6-仲-烷基酚和空间位阻酚组成的增效混合物 | |
CN1251944C (zh) | 抗静电柔性中间散装集装箱 | |
JP5329225B2 (ja) | 加硫されたエラストマー用の非染色性の劣化防止剤 | |
RU2058984C1 (ru) | Производные s-триазина и способ их получения | |
JP3118732B2 (ja) | 置換された1−アミノナフタレン類および安定化された組成物 | |
CN1127536C (zh) | 弹性体的稳定剂和抗臭氧剂 | |
US5840908A (en) | Sulfenamide accelerators and rubber compositions containing the same | |
FR2799764A1 (fr) | Compositions de caoutchouc brut en emulsion, de latex synthetique ou de latex de caoutchouc naturel stabilisees par des esters de l'acide beta-(5-tert-butyl-4-hydroxy-3 methylphenyl) propionique | |
GB1600651A (en) | Substituted haloacetamide antioxidants for elastomers and plastic polymers | |
US3668254A (en) | N-HALOALLYL-p-PHENYLENEDIAMINES |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
AD01 | Patent right deemed abandoned | ||
C20 | Patent right or utility model deemed to be abandoned or is abandoned |