DE2753194C2 - Bis-(4-anilinophenoxy)-ester und deren Verwendung - Google Patents
Bis-(4-anilinophenoxy)-ester und deren VerwendungInfo
- Publication number
- DE2753194C2 DE2753194C2 DE2753194A DE2753194A DE2753194C2 DE 2753194 C2 DE2753194 C2 DE 2753194C2 DE 2753194 A DE2753194 A DE 2753194A DE 2753194 A DE2753194 A DE 2753194A DE 2753194 C2 DE2753194 C2 DE 2753194C2
- Authority
- DE
- Germany
- Prior art keywords
- bis
- anilinophenoxy
- acid
- propyl
- examples
- 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.)
- Expired
Links
- -1 4-anilinophenoxy Chemical group 0.000 title description 22
- 150000002148 esters Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 239000003963 antioxidant agent Substances 0.000 description 9
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- GNMCEWMUFTZBKH-UHFFFAOYSA-N 3-[2-(2-carboxyethylsulfanyl)ethylsulfanyl]propanoic acid Chemical compound OC(=O)CCSCCSCCC(O)=O GNMCEWMUFTZBKH-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 230000003078 antioxidant effect Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010525 oxidative degradation reaction Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- PADTVLMSSMACIH-UHFFFAOYSA-N 1-(4-anilino-2-methylphenoxy)propan-2-yl 3-[3-[1-(4-anilino-2-methylphenoxy)propan-2-yloxy]-3-oxopropyl]sulfanylpropanoate Chemical compound C=1C=C(NC=2C=CC=CC=2)C=C(C)C=1OCC(C)OC(=O)CCSCCC(=O)OC(C)COC(C(=C1)C)=CC=C1NC1=CC=CC=C1 PADTVLMSSMACIH-UHFFFAOYSA-N 0.000 description 2
- QYWFEBHNMGJEQQ-UHFFFAOYSA-N 1-(4-anilinophenoxy)propan-2-yl 3-[2-[3-[1-(4-anilinophenoxy)propan-2-yloxy]-3-oxopropyl]sulfanylpropylsulfanyl]propanoate Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1OCC(C)OC(=O)CCSC(C)CSCCC(=O)OC(C)COC(C=C1)=CC=C1NC1=CC=CC=C1 QYWFEBHNMGJEQQ-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 2
- BTHTUXOKYVYUJM-UHFFFAOYSA-N 3-[2-(2-carboxyethylsulfanyl)propylsulfanyl]propanoic acid Chemical compound OC(=O)CCSC(C)CSCCC(O)=O BTHTUXOKYVYUJM-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002174 Styrene-butadiene Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- VGHNRTHEBWBIIG-UHFFFAOYSA-N bis[1-(4-anilinophenoxy)propan-2-yl] nonanedioate Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1OCC(C)OC(=O)CCCCCCCC(=O)OC(C)COC(C=C1)=CC=C1NC1=CC=CC=C1 VGHNRTHEBWBIIG-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- DKSMCEUSSQTGBK-UHFFFAOYSA-M bromite Chemical compound [O-]Br=O DKSMCEUSSQTGBK-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- LIMYLMBOJILGJX-UHFFFAOYSA-N 1-(4-anilinophenoxy)propan-2-ol Chemical compound C1=CC(OCC(O)C)=CC=C1NC1=CC=CC=C1 LIMYLMBOJILGJX-UHFFFAOYSA-N 0.000 description 1
- OMDFVOLHWDYRGG-UHFFFAOYSA-N 1-(4-anilinophenoxy)propan-2-yl 3-[2-[3-[1-(4-anilinophenoxy)propan-2-yloxy]-3-oxopropyl]sulfanylethylsulfanyl]propanoate Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1OCC(C)OC(=O)CCSCCSCCC(=O)OC(C)COC(C=C1)=CC=C1NC1=CC=CC=C1 OMDFVOLHWDYRGG-UHFFFAOYSA-N 0.000 description 1
- OQSUMXVPNSKIGK-UHFFFAOYSA-N 1-(4-anilinophenoxy)propan-2-yl 3-[3-[1-(4-anilinophenoxy)propan-2-yloxy]-3-oxopropyl]sulfanylpropanoate Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1OCC(C)OC(=O)CCSCCC(=O)OC(C)COC(C=C1)=CC=C1NC1=CC=CC=C1 OQSUMXVPNSKIGK-UHFFFAOYSA-N 0.000 description 1
- BTUDGPVTCYNYLK-UHFFFAOYSA-N 2,2-dimethylglutaric acid Chemical compound OC(=O)C(C)(C)CCC(O)=O BTUDGPVTCYNYLK-UHFFFAOYSA-N 0.000 description 1
- WRIHVEVTOGSHAS-UHFFFAOYSA-N 2-(4-anilinophenoxy)ethanol Chemical compound C1=CC(OCCO)=CC=C1NC1=CC=CC=C1 WRIHVEVTOGSHAS-UHFFFAOYSA-N 0.000 description 1
- ZQLOVEFZBNCMLV-UHFFFAOYSA-N 3,3-bis(sulfanyl)propanoic acid Chemical compound OC(=O)CC(S)S ZQLOVEFZBNCMLV-UHFFFAOYSA-N 0.000 description 1
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000000899 Gutta-Percha Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 240000000342 Palaquium gutta Species 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- WBFLIYRIUJJRNP-UHFFFAOYSA-N [3-(4-anilinophenoxy)-2-hydroxypropyl] 3-[2-[3-[3-(4-anilinophenoxy)-2-hydroxypropoxy]-3-oxopropyl]sulfanylethylsulfanyl]propanoate Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1OCC(O)COC(=O)CCSCCSCCC(=O)OCC(O)COC(C=C1)=CC=C1NC1=CC=CC=C1 WBFLIYRIUJJRNP-UHFFFAOYSA-N 0.000 description 1
- ODVBNUYDQKIHAA-UHFFFAOYSA-N [3-(4-anilinophenoxy)-2-hydroxypropyl] 3-[3-[3-(4-anilinophenoxy)-2-hydroxypropoxy]-3-oxopropyl]sulfanylpropanoate Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1OCC(O)COC(=O)CCSCCC(=O)OCC(O)COC(C=C1)=CC=C1NC1=CC=CC=C1 ODVBNUYDQKIHAA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 244000001591 balata Species 0.000 description 1
- 235000016302 balata Nutrition 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- OOESDTTWMHUHRE-UHFFFAOYSA-N bis[1-(4-anilinophenoxy)propan-2-yl] butanedioate Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1OCC(C)OC(=O)CCC(=O)OC(C)COC(C=C1)=CC=C1NC1=CC=CC=C1 OOESDTTWMHUHRE-UHFFFAOYSA-N 0.000 description 1
- NISPVCIDOGPKFV-UHFFFAOYSA-N bis[1-(4-anilinophenoxy)propan-2-yl] hexanedioate Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1OCC(C)OC(=O)CCCCC(=O)OC(C)COC(C=C1)=CC=C1NC1=CC=CC=C1 NISPVCIDOGPKFV-UHFFFAOYSA-N 0.000 description 1
- DUJXCJGGWQQHHE-UHFFFAOYSA-N bis[3-(4-anilinophenoxy)-2-hydroxypropyl] hexanedioate Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1OCC(O)COC(=O)CCCCC(=O)OCC(O)COC(C=C1)=CC=C1NC1=CC=CC=C1 DUJXCJGGWQQHHE-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229920000588 gutta-percha Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000003022 phthalic acids Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 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
- 238000010998 test method Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/28—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen, oxygen and sulfur
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/751,494 US4077942A (en) | 1976-12-17 | 1976-12-17 | Bis(4-anilinophenoxy) ester antioxidants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2753194A1 DE2753194A1 (de) | 1978-06-22 |
| DE2753194C2 true DE2753194C2 (de) | 1986-07-31 |
Family
ID=25022231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2753194A Expired DE2753194C2 (de) | 1976-12-17 | 1977-11-29 | Bis-(4-anilinophenoxy)-ester und deren Verwendung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4077942A (enExample) |
| JP (1) | JPS5377033A (enExample) |
| CA (1) | CA1120948A (enExample) |
| DE (1) | DE2753194C2 (enExample) |
| FR (1) | FR2374303A1 (enExample) |
| GB (1) | GB1553795A (enExample) |
| IT (1) | IT1092167B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5155148A (en) * | 1989-09-25 | 1992-10-13 | The Goodyear Tire & Rubber Company | Ester derivatives from p-hydroxydiphenylamine |
| CA2019062A1 (en) * | 1989-09-25 | 1991-03-25 | Dane Kenton Parker | Ester derivatives from p-hydroxydiphenylamine |
| 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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3004073A (en) * | 1959-05-05 | 1961-10-10 | Pittsburgh Plate Glass Co | Process to prepare 1-pentachlorophenoxy-2,3-propanediol |
| US4021474A (en) * | 1974-04-03 | 1977-05-03 | Hooker Chemicals & Plastics Corporation | Antidegradant esters |
-
1976
- 1976-12-17 US US05/751,494 patent/US4077942A/en not_active Expired - Lifetime
-
1977
- 1977-11-07 CA CA000290360A patent/CA1120948A/en not_active Expired
- 1977-11-09 GB GB46624/77A patent/GB1553795A/en not_active Expired
- 1977-11-29 DE DE2753194A patent/DE2753194C2/de not_active Expired
- 1977-12-06 IT IT52093/77A patent/IT1092167B/it active
- 1977-12-15 FR FR7737897A patent/FR2374303A1/fr active Granted
- 1977-12-15 JP JP15118177A patent/JPS5377033A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1092167B (it) | 1985-07-06 |
| JPS5377033A (en) | 1978-07-08 |
| US4077942A (en) | 1978-03-07 |
| FR2374303B1 (enExample) | 1980-08-22 |
| JPS6125019B2 (enExample) | 1986-06-13 |
| FR2374303A1 (fr) | 1978-07-13 |
| DE2753194A1 (de) | 1978-06-22 |
| CA1120948A (en) | 1982-03-30 |
| GB1553795A (en) | 1979-10-10 |
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