CS227302B2 - Způsob inhibice oxidačního odbourání organického materiálu - Google Patents
Způsob inhibice oxidačního odbourání organického materiálu Download PDFInfo
- Publication number
- CS227302B2 CS227302B2 CS536979A CS536979A CS227302B2 CS 227302 B2 CS227302 B2 CS 227302B2 CS 536979 A CS536979 A CS 536979A CS 536979 A CS536979 A CS 536979A CS 227302 B2 CS227302 B2 CS 227302B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydroxyphenyl
- tert
- radical
- butyl
- mol
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 24
- 239000011368 organic material Substances 0.000 title claims description 15
- 238000010525 oxidative degradation reaction Methods 0.000 title claims description 10
- 230000002401 inhibitory effect Effects 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 69
- -1 alkyl radical Chemical class 0.000 claims description 64
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 150000003254 radicals Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000203 mixture Substances 0.000 description 75
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
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- 239000002253 acid Substances 0.000 description 17
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- 238000004821 distillation Methods 0.000 description 13
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- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 9
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- 238000002360 preparation method Methods 0.000 description 5
- GHAQLQRXNCECQB-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)-n-(2-hydroxyethyl)propanamide Chemical compound CC(C)(C)C1=CC(CCC(=O)NCCO)=CC(C(C)(C)C)=C1O GHAQLQRXNCECQB-UHFFFAOYSA-N 0.000 description 4
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- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
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- 239000002244 precipitate Substances 0.000 description 4
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- FNVOFDGAASRDQY-UHFFFAOYSA-N 3-amino-2,2-dimethylpropan-1-ol Chemical compound NCC(C)(C)CO FNVOFDGAASRDQY-UHFFFAOYSA-N 0.000 description 3
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- OTGQIQQTPXJQRG-UHFFFAOYSA-N N-(octadecanoyl)ethanolamine Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCO OTGQIQQTPXJQRG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 239000012044 organic layer Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- ZAMFGZLTCFDBLG-UHFFFAOYSA-N 3-(octadecanoylamino)propyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 ZAMFGZLTCFDBLG-UHFFFAOYSA-N 0.000 description 1
- ASKYEJHKIFCKRQ-UHFFFAOYSA-N 3-(octadecanoylamino)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCCOC(=O)CCCCCCCCCCCCCCCCC ASKYEJHKIFCKRQ-UHFFFAOYSA-N 0.000 description 1
- FVXBTPGZQMNAEZ-UHFFFAOYSA-N 3-amino-2-methylpropan-1-ol Chemical compound NCC(C)CO FVXBTPGZQMNAEZ-UHFFFAOYSA-N 0.000 description 1
- FERWBXLFSBWTDE-UHFFFAOYSA-N 3-aminobutan-2-ol Chemical compound CC(N)C(C)O FERWBXLFSBWTDE-UHFFFAOYSA-N 0.000 description 1
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 1
- IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 1
- XRDWFFPDGXUBGS-UHFFFAOYSA-N 4-hydroxy-2,3,3-trimethylbutanamide Chemical compound NC(=O)C(C)C(C)(C)CO XRDWFFPDGXUBGS-UHFFFAOYSA-N 0.000 description 1
- LQGKDMHENBFVRC-UHFFFAOYSA-N 5-aminopentan-1-ol Chemical compound NCCCCCO LQGKDMHENBFVRC-UHFFFAOYSA-N 0.000 description 1
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- YMVIICSBEQAPAW-UHFFFAOYSA-N C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1CC(CC(C)C)(C(O)=O)NC(=O)CCCCC(=O)NC(C(O)=O)(CC(C)C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1CC(CC(C)C)(C(O)=O)NC(=O)CCCCC(=O)NC(C(O)=O)(CC(C)C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 YMVIICSBEQAPAW-UHFFFAOYSA-N 0.000 description 1
- RLUZUNJTWKQBMG-UHFFFAOYSA-N CC(C)(CNC(=O)C(=O)N)CO Chemical compound CC(C)(CNC(=O)C(=O)N)CO RLUZUNJTWKQBMG-UHFFFAOYSA-N 0.000 description 1
- MCVDEPULYFFNDS-UHFFFAOYSA-N CC(C)(N)CC(C(O)=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 Chemical compound CC(C)(N)CC(C(O)=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 MCVDEPULYFFNDS-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XEESKQOQUSLLOT-UHFFFAOYSA-N [1-(aminomethyl)cyclohexyl]methanol Chemical compound NCC1(CO)CCCCC1 XEESKQOQUSLLOT-UHFFFAOYSA-N 0.000 description 1
- UKJPVSRKWGLHFS-UHFFFAOYSA-N [2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoylamino]-2-methylpropyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCC(C)(C)NC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 UKJPVSRKWGLHFS-UHFFFAOYSA-N 0.000 description 1
- AOMGGTBTWDFYJA-UHFFFAOYSA-N [2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoylamino]-2-methylpropyl] hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(C)(C)NC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 AOMGGTBTWDFYJA-UHFFFAOYSA-N 0.000 description 1
- PWCWWXGTVIVOBN-UHFFFAOYSA-N [2-methyl-2-(octadecanoylamino)propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC(C)(C)COC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PWCWWXGTVIVOBN-UHFFFAOYSA-N 0.000 description 1
- 239000011354 acetal resin Substances 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- MMXKVMNBHPAILY-UHFFFAOYSA-N dodecanoic acid ethyl ester Natural products CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- ZCWSUZJGZZFSHM-UHFFFAOYSA-N ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 ZCWSUZJGZZFSHM-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YMVXPZAKIVJWBR-UHFFFAOYSA-N n'-(3-hydroxypropyl)oxamide Chemical compound NC(=O)C(=O)NCCCO YMVXPZAKIVJWBR-UHFFFAOYSA-N 0.000 description 1
- GTBODJTVLNPEEM-UHFFFAOYSA-N n-(3-hydroxypropyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCCO GTBODJTVLNPEEM-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- MVLVMROFTAUDAG-UHFFFAOYSA-N octadecanoic acid ethyl ester Natural products CCCCCCCCCCCCCCCCCC(=O)OCC MVLVMROFTAUDAG-UHFFFAOYSA-N 0.000 description 1
- WVJVHUWVQNLPCR-UHFFFAOYSA-N octadecanoyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCC WVJVHUWVQNLPCR-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 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
- 239000012429 reaction media Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Lubricants (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93108778A | 1978-08-04 | 1978-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS227302B2 true CS227302B2 (cs) | 1984-04-16 |
Family
ID=25460209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS536979A CS227302B2 (cs) | 1978-08-04 | 1979-08-03 | Způsob inhibice oxidačního odbourání organického materiálu |
Country Status (4)
| Country | Link |
|---|---|
| JP (2) | JPS5543080A (ja) |
| BR (1) | BR7904999A (ja) |
| CS (1) | CS227302B2 (ja) |
| ZA (2) | ZA794012B (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5837051A (ja) * | 1981-08-27 | 1983-03-04 | Toyobo Co Ltd | 安定化されたポリウレタン弾性繊維 |
| US4435253A (en) * | 1983-01-28 | 1984-03-06 | Omi International Corporation | Gold sulphite electroplating solutions and methods |
| JP2604166B2 (ja) * | 1987-07-31 | 1997-04-30 | 日清製油株式会社 | 潤滑油 |
| BE1014162A3 (fr) * | 1997-05-26 | 2003-06-03 | Ciba Sc Holding Ag | Produits stabilisants, compositions et concentres les contenant, et leur procede d'utilisation. |
| JP4974136B2 (ja) * | 2006-03-31 | 2012-07-11 | 株式会社興人 | バイオディーゼル燃料の加水分解抑制剤及び該抑制剤を含有したバイオディーゼル燃料 |
-
1979
- 1979-08-03 CS CS536979A patent/CS227302B2/cs unknown
- 1979-08-03 ZA ZA00794012A patent/ZA794012B/xx unknown
- 1979-08-03 BR BR7904999A patent/BR7904999A/pt not_active IP Right Cessation
- 1979-08-03 ZA ZA00794013A patent/ZA794013B/xx unknown
- 1979-08-03 JP JP9939179A patent/JPS5543080A/ja active Granted
- 1979-08-03 JP JP9939079A patent/JPS5531073A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5531073A (en) | 1980-03-05 |
| JPS6254298B2 (ja) | 1987-11-13 |
| JPS5543080A (en) | 1980-03-26 |
| ZA794013B (en) | 1981-06-24 |
| JPS6129348B2 (ja) | 1986-07-05 |
| ZA794012B (en) | 1980-08-27 |
| BR7904999A (pt) | 1980-02-12 |
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