TWI308145B - Phenolic antioxidants in crystalline form - Google Patents
Phenolic antioxidants in crystalline form Download PDFInfo
- Publication number
- TWI308145B TWI308145B TW092132857A TW92132857A TWI308145B TW I308145 B TWI308145 B TW I308145B TW 092132857 A TW092132857 A TW 092132857A TW 92132857 A TW92132857 A TW 92132857A TW I308145 B TWI308145 B TW I308145B
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- Prior art keywords
- weak
- medium
- butyl
- strong
- bis
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- 239000002530 phenolic antioxidant Substances 0.000 title description 6
- -1 polyoxyethylene Polymers 0.000 claims description 120
- 239000013078 crystal Substances 0.000 claims description 97
- 239000006185 dispersion Substances 0.000 claims description 56
- 239000002245 particle Substances 0.000 claims description 56
- 239000000203 mixture Substances 0.000 claims description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 45
- 239000007787 solid Substances 0.000 claims description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000000600 sorbitol Substances 0.000 claims description 32
- 239000000052 vinegar Substances 0.000 claims description 32
- 235000021419 vinegar Nutrition 0.000 claims description 32
- 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 claims description 31
- 239000002253 acid Substances 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 24
- 239000007788 liquid Substances 0.000 claims description 22
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 17
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 16
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 13
- 239000000194 fatty acid Substances 0.000 claims description 13
- 229930195729 fatty acid Natural products 0.000 claims description 13
- 150000004665 fatty acids Chemical class 0.000 claims description 10
- 239000008187 granular material Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000012545 processing Methods 0.000 claims description 6
- 238000001125 extrusion Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- BBCPTRQPIONARW-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-2-methylhexanamide Chemical compound CCCCC(C)(C(N)=O)C1=CC=C(O)C=C1 BBCPTRQPIONARW-UHFFFAOYSA-N 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 229940049964 oleate Drugs 0.000 claims description 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 4
- 229930040373 Paraformaldehyde Natural products 0.000 claims 2
- 229920006324 polyoxymethylene Polymers 0.000 claims 2
- CSNSMMCZYGNIFG-UHFFFAOYSA-N 2-(4-hydroxyphenyl)propanamide Chemical compound NC(=O)C(C)C1=CC=C(O)C=C1 CSNSMMCZYGNIFG-UHFFFAOYSA-N 0.000 claims 1
- 206010002091 Anaesthesia Diseases 0.000 claims 1
- 238000001949 anaesthesia Methods 0.000 claims 1
- 230000037005 anaesthesia Effects 0.000 claims 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 238000007906 compression Methods 0.000 claims 1
- 230000006835 compression Effects 0.000 claims 1
- 238000010908 decantation Methods 0.000 claims 1
- DKSRNSSBMXOZAJ-UHFFFAOYSA-N dodecanoic acid;ethene Chemical group C=C.CCCCCCCCCCCC(O)=O DKSRNSSBMXOZAJ-UHFFFAOYSA-N 0.000 claims 1
- 238000005469 granulation Methods 0.000 claims 1
- 230000003179 granulation Effects 0.000 claims 1
- 210000003127 knee Anatomy 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 15
- 239000000654 additive Substances 0.000 description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
- 239000000155 melt Substances 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 241000208340 Araliaceae Species 0.000 description 10
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 10
- 235000003140 Panax quinquefolius Nutrition 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 239000012964 benzotriazole Substances 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- 235000008434 ginseng Nutrition 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229960003742 phenol Drugs 0.000 description 8
- 229920000136 polysorbate Polymers 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 7
- 235000019260 propionic acid Nutrition 0.000 description 7
- 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 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
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- 238000002156 mixing Methods 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000010561 standard procedure Methods 0.000 description 6
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
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- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
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- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
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- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 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
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 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
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 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 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- KBRSKMOKKFOTGW-UHFFFAOYSA-N tetraphosphanium tetrahydroxide Chemical group [OH-].[PH4+].[PH4+].[PH4+].[PH4+].[OH-].[OH-].[OH-] KBRSKMOKKFOTGW-UHFFFAOYSA-N 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/002—Physical properties
- C08K2201/005—Additives being defined by their particle size in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02406023 | 2002-11-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200415234A TW200415234A (en) | 2004-08-16 |
| TWI308145B true TWI308145B (en) | 2009-04-01 |
Family
ID=32338231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092132857A TWI308145B (en) | 2002-11-26 | 2003-11-24 | Phenolic antioxidants in crystalline form |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7262319B2 (enExample) |
| EP (1) | EP1575895A1 (enExample) |
| JP (1) | JP2006507337A (enExample) |
| KR (1) | KR20050085019A (enExample) |
| CN (1) | CN100448838C (enExample) |
| AU (1) | AU2003300566B2 (enExample) |
| BR (1) | BR0316567A (enExample) |
| MY (1) | MY136146A (enExample) |
| RU (1) | RU2362764C2 (enExample) |
| TW (1) | TWI308145B (enExample) |
| WO (1) | WO2004048312A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006014605A2 (en) * | 2004-07-23 | 2006-02-09 | Polnox Corporation | Anti-oxidant macromonomers and polymers and methods of making and using the same |
| JP2008508231A (ja) | 2004-07-27 | 2008-03-21 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | フェノール系抗酸化剤の固体粒子を調製する方法 |
| US7902317B2 (en) | 2004-12-03 | 2011-03-08 | Polnox Corporation | Synthesis of aniline and phenol-based antioxidant macromonomers and corresponding polymers |
| WO2006091705A2 (en) | 2005-02-22 | 2006-08-31 | Polnox Corporation | Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis , performances and applications |
| US7705185B2 (en) | 2005-03-25 | 2010-04-27 | Polnox Corporation | Alkylated and polymeric macromolecular antioxidants and methods of making and using the same |
| EP1966293A1 (en) | 2005-10-27 | 2008-09-10 | Polnox Corporation | Stabilized polyolefin compositions |
| WO2007050985A2 (en) | 2005-10-27 | 2007-05-03 | Polnox Corporation | Macromolecular antioxidants based on stξrically hindered phenolic phosphites |
| US20070161522A1 (en) | 2005-12-02 | 2007-07-12 | Cholli Ashok L | Lubricant oil compositions |
| WO2008005358A2 (en) | 2006-07-06 | 2008-01-10 | Polnox Corporation | Novel macromolecular antioxidants comprising differing antioxidant moieties: structures, methods of making and using the same |
| US7767853B2 (en) | 2006-10-20 | 2010-08-03 | Polnox Corporation | Antioxidants and methods of making and using the same |
| WO2008055832A2 (en) * | 2006-11-09 | 2008-05-15 | Ciba Holding Inc. | Process using liquid phenolic antioxidants |
| KR101211231B1 (ko) * | 2008-08-21 | 2012-12-11 | 주식회사 엘지화학 | 산화방지제 유성 분산액과 이의 제조방법 및 이로부터 제조된 염화비닐계 수지 중합체 |
| JP5330904B2 (ja) * | 2009-06-12 | 2013-10-30 | 住友化学株式会社 | 粒状物質の製造方法 |
| BR112013023637B1 (pt) * | 2011-03-14 | 2020-12-15 | Dow Global Technologies Llc | Composição e artigo |
| JP5542289B2 (ja) * | 2012-01-23 | 2014-07-09 | トヨタ自動車株式会社 | オイル添加物およびオイルフィルター |
| US10294423B2 (en) | 2013-11-22 | 2019-05-21 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures, methods of making and using the same |
| US20180251695A1 (en) | 2017-03-01 | 2018-09-06 | Polnox Corporation | Macromolecular Corrosion (McIn) Inhibitors: Structures, Methods Of Making And Using The Same |
| EP3609861A1 (en) | 2017-04-10 | 2020-02-19 | Basf Se | Low volatile organic anti-oxidation stabilisers for polymeric systems, their production and use |
| CN107417528A (zh) * | 2017-05-02 | 2017-12-01 | 沈阳化工大学 | 一种抗氧剂1076在甲醇溶剂中得到针状晶形结晶的方法 |
| CN111495312B (zh) * | 2020-05-22 | 2023-07-28 | 河南心连心化学工业集团股份有限公司 | 一种草酰胺合成装置以及合成方法 |
| KR102771644B1 (ko) * | 2022-06-21 | 2025-02-26 | 금호석유화학 주식회사 | 산화방지제의 제조방법 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3644482A (en) * | 1961-10-30 | 1972-02-22 | Geigy Ag J R | (4-hydroxy-5-alkylphenyl) alkanoic acid esters of polyols |
| GB1123505A (en) * | 1966-01-10 | 1968-08-14 | Sankyo Co | Method for the production of microcrystals of chloramphenicol |
| US3666809A (en) * | 1969-10-08 | 1972-05-30 | Mitsubishi Chem Ind | Method for the production of acrylamide crystals |
| US3867414A (en) * | 1969-12-04 | 1975-02-18 | Yamanouchi Pharma Co Ltd | Process for the preparation of suspensions of microcrystals of chloramphenicol palmitate |
| AT303971B (de) * | 1969-12-04 | 1972-12-27 | Yamanouchi Pharma Co Ltd | Verfahren zur Herstellung einer Suspension von Chloramphenicol-palmitat in mikrokristalliner Form |
| JPS6013018B2 (ja) * | 1980-04-01 | 1985-04-04 | 三井化学株式会社 | 新規な結晶構造を有するテトラキス〔３−（３，５−ジ−ｔ−ブチル−４−ヒドロキシフエニル）プロピオニルオキシメチル〕メタン |
| JPS6013017B2 (ja) * | 1980-01-14 | 1985-04-04 | 三井化学株式会社 | テトラキス〔３−（３，５−ジ−ｔ−ブチル−４−ヒドロキシフエニル）プロピオニルオキシメチル〕メタンの製造方法 |
| US4405807A (en) * | 1980-01-14 | 1983-09-20 | Mitsui Petrochemical Industries, Ltd. | Tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxymethyl]methane having a novel crystal structure and process for production thereof |
| JPS57197245A (en) * | 1981-05-28 | 1982-12-03 | Mitsui Petrochem Ind Ltd | Tetrakis(3-(3,5-dibutyl-4-hydroxyphenyl) propionyloxymethyl)methane |
| JPS5974182A (ja) * | 1982-10-20 | 1984-04-26 | Sumitomo Chem Co Ltd | 複合酸化防止剤の球状製品の製造法 |
| JPS6063274A (ja) * | 1983-09-16 | 1985-04-11 | Mitsui Toatsu Chem Inc | 酸化防止剤分散液 |
| JPH0689171B2 (ja) * | 1984-03-07 | 1994-11-09 | 三井東圧化学株式会社 | 酸化防止剤分散液の製造方法 |
| DE3673055D1 (de) * | 1985-05-02 | 1990-09-06 | Ciba Geigy Ag | Verfahren zum stabilisieren von kugelfoermig polymerisierten polyolefinen. |
| US4683326A (en) * | 1985-07-19 | 1987-07-28 | Ciba-Geigy Corporation | Solvent-free crystallization of pentaerythritol tetrakis-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] and the novel alpha-crystalline form thereof |
| JPH0657676B2 (ja) * | 1986-04-30 | 1994-08-03 | ムサシノガイギ−株式会社 | 独立粒子状β晶テトラキス〔３−（３，５−ジ−ｔ−ブチル−４−ヒドロキシフエニル）プロピオニルオキシメチル〕メタンおよびその製造方法 |
| JPS63159315A (ja) * | 1986-12-22 | 1988-07-02 | Yuutoku Yakuhin Kogyo Kk | パツプ剤 |
| EP0366808B1 (en) * | 1988-03-31 | 1994-06-15 | Yoshitomi Pharmaceutical Industries, Ltd. | Method of crystallization and purification for obtaining stable crystalls of tetrakis 3-(3,5-di-tertiary-butyl-4-hydroxyphenyl)propionyloxymethyl- methane on an industrial scale |
| JPH075518B2 (ja) * | 1988-03-31 | 1995-01-25 | 吉富製薬株式会社 | テトラキス〔３―（３，５―ジ第３級ブチル―４―ヒドロキシフェニル）プロピオニルオキシメチル〕メタンのβ晶の晶出精製方法 |
| US4847585A (en) | 1988-05-20 | 1989-07-11 | Mosebach Manufacturing Company | Center ventilated resistor grid |
| JP2736265B2 (ja) * | 1989-06-08 | 1998-04-02 | 吉富製薬株式会社 | 粉体特性の優れたα晶テトラキス〔３―（３，５―ジ―ｔ―ブチル―４―ヒドロキシフェニル）プロピオニルオキシメチル〕メタンの製造法 |
| JPH085844B2 (ja) * | 1989-06-08 | 1996-01-24 | 吉富製薬株式会社 | 流動性の優れたα晶テトラキス〔３―（３，５―ジ―ｔ―ブチル―４―ヒドロキシフェニル）プロピオニルオキシメチル〕メタンおよびその製造方法 |
| US5204022A (en) * | 1989-08-11 | 1993-04-20 | Eastman Kodak Company | Solid-form additive systems dispersible in aqueous media |
| JP2819163B2 (ja) * | 1989-08-25 | 1998-10-30 | 旭電化工業株式会社 | ラテックス用酸化防止剤分散液 |
| JPH03146563A (ja) * | 1989-11-01 | 1991-06-21 | Adeka Argus Chem Co Ltd | ラテックス用酸化防止剤分散液 |
| JP3024802B2 (ja) * | 1991-02-04 | 2000-03-27 | ポリプラスチックス株式会社 | ポリアセタール樹脂着色組成物 |
| JPH05271516A (ja) * | 1992-03-26 | 1993-10-19 | Polyplastics Co | ポリオキシメチレン組成物 |
| CA2092952A1 (en) * | 1992-03-31 | 1993-10-01 | Pak S. Leung | Dispersions of polymer additives in fatty acid esters |
| JPH0625430A (ja) * | 1992-07-09 | 1994-02-01 | Yoshitomi Pharmaceut Ind Ltd | 有機材料の安定化処理法 |
| JP3215728B2 (ja) * | 1992-10-15 | 2001-10-09 | 旭電化工業株式会社 | テトラキス〔３−（３，５−ジ第三ブチル−４−ヒドロキシフェニル）プロピオニルオキシメチル〕メタンの製造方法 |
| DE19523115A1 (de) * | 1995-06-26 | 1997-01-02 | Hoechst Ag | Dispersionspulver mit erhöhter Selbstentzündungstemperatur |
| GB9624615D0 (en) * | 1996-11-26 | 1997-01-15 | Zeneca Ltd | Chrystallisation process |
| AU7043298A (en) * | 1997-04-15 | 1998-11-11 | Ciba Specialty Chemicals Holding Inc. | Preparation of low-dust stabilisers |
| FR2775903B1 (fr) * | 1998-03-12 | 2001-06-08 | Lhd Lab Hygiene Dietetique | Masse hydrocolloide a absorption accrue des les premieres heures d'utilisation |
-
2003
- 2003-11-17 RU RU2005120164/04A patent/RU2362764C2/ru not_active IP Right Cessation
- 2003-11-17 WO PCT/EP2003/050838 patent/WO2004048312A1/en not_active Ceased
- 2003-11-17 KR KR1020057008843A patent/KR20050085019A/ko not_active Ceased
- 2003-11-17 AU AU2003300566A patent/AU2003300566B2/en not_active Ceased
- 2003-11-17 US US10/534,513 patent/US7262319B2/en not_active Expired - Fee Related
- 2003-11-17 BR BR0316567-1A patent/BR0316567A/pt not_active Application Discontinuation
- 2003-11-17 JP JP2004554535A patent/JP2006507337A/ja active Pending
- 2003-11-17 CN CNB2003801041780A patent/CN100448838C/zh not_active Expired - Fee Related
- 2003-11-17 EP EP03811779A patent/EP1575895A1/en not_active Ceased
- 2003-11-22 MY MYPI20034507A patent/MY136146A/en unknown
- 2003-11-24 TW TW092132857A patent/TWI308145B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2005120164A (ru) | 2006-04-27 |
| MY136146A (en) | 2008-08-29 |
| WO2004048312A1 (en) | 2004-06-10 |
| US20060189820A1 (en) | 2006-08-24 |
| EP1575895A1 (en) | 2005-09-21 |
| CN1717385A (zh) | 2006-01-04 |
| AU2003300566B2 (en) | 2010-01-21 |
| AU2003300566A1 (en) | 2004-06-18 |
| RU2362764C2 (ru) | 2009-07-27 |
| CN100448838C (zh) | 2009-01-07 |
| JP2006507337A (ja) | 2006-03-02 |
| US7262319B2 (en) | 2007-08-28 |
| KR20050085019A (ko) | 2005-08-29 |
| TW200415234A (en) | 2004-08-16 |
| BR0316567A (pt) | 2005-10-04 |
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