DE2164800C3 - p-Aminophenylamino-s-triazin-Verbindungen und deren Verwendung - Google Patents
p-Aminophenylamino-s-triazin-Verbindungen und deren VerwendungInfo
- Publication number
- DE2164800C3 DE2164800C3 DE2164800A DE2164800A DE2164800C3 DE 2164800 C3 DE2164800 C3 DE 2164800C3 DE 2164800 A DE2164800 A DE 2164800A DE 2164800 A DE2164800 A DE 2164800A DE 2164800 C3 DE2164800 C3 DE 2164800C3
- Authority
- DE
- Germany
- Prior art keywords
- ippd
- phenylenediamine
- rubber
- bis
- nhc
- 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
- YMFGJWGABDOFID-UHFFFAOYSA-N amanozine Chemical class NC1=NC=NC(NC=2C=CC=CC=2)=N1 YMFGJWGABDOFID-UHFFFAOYSA-N 0.000 title 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical class NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 3
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 97
- 229910052757 nitrogen Inorganic materials 0.000 description 30
- 239000000203 mixture Substances 0.000 description 21
- 239000003381 stabilizer Substances 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 20
- 229920001971 elastomer Polymers 0.000 description 18
- 239000005060 rubber Substances 0.000 description 17
- 230000003712 anti-aging effect Effects 0.000 description 14
- -1 alkyl radical Chemical class 0.000 description 13
- 125000001309 chloro group Chemical group Cl* 0.000 description 12
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000032683 aging Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000003918 triazines Chemical class 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000002845 discoloration Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 5
- 244000043261 Hevea brasiliensis Species 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 230000002929 anti-fatigue Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 229920003052 natural elastomer Polymers 0.000 description 5
- 229920001194 natural rubber Polymers 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 150000004989 p-phenylenediamines Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000035882 stress Effects 0.000 description 3
- 239000004636 vulcanized rubber Substances 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- PDAYVCJRTDDAFS-UHFFFAOYSA-N 4-N-(4-anilinophenyl)-6-chloro-2-N-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound C1(=CC=CC=C1)NC1=CC=C(C=C1)NC1=NC(=NC(=N1)Cl)NC(C)C PDAYVCJRTDDAFS-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 2
- 238000009661 fatigue test Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RBRKCJCVPLSVEO-UHFFFAOYSA-N 1-n,4-n-bis(4,6-dichloro-1,3,5-triazin-2-yl)benzene-1,4-diamine Chemical compound ClC1=NC(Cl)=NC(NC=2C=CC(NC=3N=C(Cl)N=C(Cl)N=3)=CC=2)=N1 RBRKCJCVPLSVEO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- XMUGVXZKCPQZAB-UHFFFAOYSA-N 2-n-[4-[(4,6-diamino-1,3,5-triazin-2-yl)amino]phenyl]-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2C=CC(NC=3N=C(N)N=C(N)N=3)=CC=2)=N1 XMUGVXZKCPQZAB-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- CPGFMWPQXUXQRX-UHFFFAOYSA-N 3-amino-3-(4-fluorophenyl)propanoic acid Chemical compound OC(=O)CC(N)C1=CC=C(F)C=C1 CPGFMWPQXUXQRX-UHFFFAOYSA-N 0.000 description 1
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- HLBZWYXLQJQBKU-UHFFFAOYSA-N 4-(morpholin-4-yldisulfanyl)morpholine Chemical compound C1COCCN1SSN1CCOCC1 HLBZWYXLQJQBKU-UHFFFAOYSA-N 0.000 description 1
- JFJOEUGRBAQXDG-UHFFFAOYSA-N 4-chloro-n-phenyl-1,3,5-triazin-2-amine Chemical compound ClC1=NC=NC(NC=2C=CC=CC=2)=N1 JFJOEUGRBAQXDG-UHFFFAOYSA-N 0.000 description 1
- RDDXLTPBALMBBI-UHFFFAOYSA-N 4-methyl-1,2-dihydroquinoline Chemical compound C1=CC=C2C(C)=CCNC2=C1 RDDXLTPBALMBBI-UHFFFAOYSA-N 0.000 description 1
- WYVZSGZYQXOJKV-UHFFFAOYSA-N 4-n-(4,6-dichloro-1,3,5-triazin-2-yl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC1=NC(Cl)=NC(Cl)=N1 WYVZSGZYQXOJKV-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- JYOQAMIUHGMNKV-UHFFFAOYSA-N COCOC.[Na] Chemical compound COCOC.[Na] JYOQAMIUHGMNKV-UHFFFAOYSA-N 0.000 description 1
- 241000134426 Ceratopogonidae Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241001244799 Gluta usitata Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920003246 polypentenamer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- 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
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S524/925—Natural rubber compositions having nonreactive materials, i.e. NRM, other than: carbon, silicon dioxide, glass titanium dioxide, water, hydrocarbon or halohydrocarbon
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Priority Applications (25)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE793389D BE793389A (fr) | 1971-12-27 | Composes de phenylenediamine-s-triazine et leur utilisation | |
| DE2164800A DE2164800C3 (de) | 1971-12-27 | 1971-12-27 | p-Aminophenylamino-s-triazin-Verbindungen und deren Verwendung |
| ZA728736A ZA728736B (en) | 1971-12-27 | 1972-12-11 | Phenylene diamine-s-triazine compounds and the use thereof |
| HUDE800A HU167257B (show.php) | 1971-12-27 | 1972-12-12 | |
| CH1803972A CH583761A5 (show.php) | 1971-12-27 | 1972-12-12 | |
| ES409786A ES409786A1 (es) | 1971-12-27 | 1972-12-19 | Procedimiento para estabilizar productos vulcanizados a ba-se de mezclas vulcanizables. |
| US00316565A US3828002A (en) | 1971-12-27 | 1972-12-19 | Rubber stabilized with phenylene-diamine-s-triazines |
| NLAANVRAGE7217445,A NL179817C (nl) | 1971-12-27 | 1972-12-21 | Werkwijze voor het bereiden van een vulcaniseerbaar mengsel; werkwijze voor het bereiden van een 1,3,5triazineverbinding; gevormde voortbrengselen. |
| DK641972A DK141404C (da) | 1971-12-27 | 1972-12-21 | Phenylendiamingruppeholdige triazinforbindelser til brug ved stabilisering af kautsjukvulkanisater |
| CS8856A CS178121B2 (show.php) | 1971-12-27 | 1972-12-21 | |
| IT55001/72A IT974295B (it) | 1971-12-27 | 1972-12-22 | Composti fenilendiammino s tria zinici e loro impiego come stabilizzatori per prodotti contenenti gomma |
| IL41151A IL41151A (en) | 1971-12-27 | 1972-12-22 | Stabilizing compositions for rubber vulcanisates containing phenylene diamine derivatives of s-triazines and some new such derivatives |
| AT1100772A AT332641B (de) | 1971-12-27 | 1972-12-22 | Stabilisierungsmittel enthaltende kautschukmischung und stabilisierungsmittel hiefur |
| AU50485/72A AU472715B2 (en) | 1971-12-27 | 1972-12-22 | Phenylene diamine-s-triazine compounds and their use |
| PL1972159810A PL82475B1 (show.php) | 1971-12-27 | 1972-12-23 | |
| JP734316A JPS5743566B2 (show.php) | 1971-12-27 | 1972-12-27 | |
| DD167920A DD102708A5 (show.php) | 1971-12-27 | 1972-12-27 | |
| CA159,983A CA978530A (en) | 1971-12-27 | 1972-12-27 | Phenylene-diamine-s-triazine compounds and their use |
| AR245860A AR197970A1 (es) | 1971-12-27 | 1972-12-27 | Derivados de 1,3,5-triazina |
| FR7246429A FR2167130A5 (show.php) | 1971-12-27 | 1972-12-27 | |
| GB5960972A GB1412610A (en) | 1971-12-27 | 1972-12-27 | 1,3,5-triazine compounds |
| BR9176/72A BR7209176D0 (pt) | 1971-12-27 | 1972-12-27 | Processo de obtencao de novas fenilenodiamina-s-triazina e misturas resultantes de seu emprego |
| IN1009/CAL/73A IN138951B (show.php) | 1971-12-27 | 1973-04-30 | |
| US473168A US3928344A (en) | 1971-12-27 | 1974-05-24 | Phenylenediamine-s-triazines |
| DK49075A DK134564C (da) | 1971-12-27 | 1975-02-11 | Fremgangsmade til fremstilling af navnlig mod materialetrethed og revnevekst beskyttede vulkanisater af kautsjukblandingerindeholdende phenylendiamingruppeholdige triazinforbindelser |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2164800A DE2164800C3 (de) | 1971-12-27 | 1971-12-27 | p-Aminophenylamino-s-triazin-Verbindungen und deren Verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2164800A1 DE2164800A1 (de) | 1973-07-12 |
| DE2164800B2 DE2164800B2 (de) | 1977-11-03 |
| DE2164800C3 true DE2164800C3 (de) | 1978-06-22 |
Family
ID=5829349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2164800A Expired DE2164800C3 (de) | 1971-12-27 | 1971-12-27 | p-Aminophenylamino-s-triazin-Verbindungen und deren Verwendung |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3828002A (show.php) |
| JP (1) | JPS5743566B2 (show.php) |
| AR (1) | AR197970A1 (show.php) |
| AT (1) | AT332641B (show.php) |
| AU (1) | AU472715B2 (show.php) |
| BE (1) | BE793389A (show.php) |
| BR (1) | BR7209176D0 (show.php) |
| CA (1) | CA978530A (show.php) |
| CH (1) | CH583761A5 (show.php) |
| CS (1) | CS178121B2 (show.php) |
| DD (1) | DD102708A5 (show.php) |
| DE (1) | DE2164800C3 (show.php) |
| DK (1) | DK141404C (show.php) |
| ES (1) | ES409786A1 (show.php) |
| FR (1) | FR2167130A5 (show.php) |
| GB (1) | GB1412610A (show.php) |
| HU (1) | HU167257B (show.php) |
| IL (1) | IL41151A (show.php) |
| IN (1) | IN138951B (show.php) |
| IT (1) | IT974295B (show.php) |
| NL (1) | NL179817C (show.php) |
| PL (1) | PL82475B1 (show.php) |
| ZA (1) | ZA728736B (show.php) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1448489A (en) * | 1973-02-21 | 1976-09-08 | Siemens Ag | Manufacture of elongate plastic structures and to polyethylene compositions for use therein |
| RO70804A (ro) * | 1974-11-20 | 1980-08-15 | Deutsche Gold-Und Silber-Scheideanstalt Vormals Roessler,De | Procedeu si dispozitiv pentru prepararea unor solutii sau suspensii de clorura de cianuril |
| US4794134A (en) * | 1987-08-28 | 1988-12-27 | Uniroyal Chemical Company, Inc. | Ozone resistant elastomeric articles |
| IL87542A (en) * | 1987-08-28 | 1993-01-31 | Uniroyal Chem Co Inc | Arylenediamino substituted triazine derivatives, processes for the preparation thereof and compositions containing the same |
| US4794135A (en) * | 1987-08-28 | 1988-12-27 | Uniroyal Chemical Company, Inc. | Arylenediamine substituted triazines |
| US5047530A (en) * | 1987-08-28 | 1991-09-10 | Uniroyal Chemical Company, Inc. | Arylenediamine substituted triazines |
| EP0331450B1 (en) * | 1988-03-04 | 1993-04-21 | UNIROYAL CHEMICAL COMPANY, Inc. | Phenylenediamines as high temperature heat stabilisers |
| US5120844A (en) * | 1988-09-21 | 1992-06-09 | Uniroyal Chemical Company, Inc. | Substituted triazines |
| US4972010A (en) * | 1988-09-21 | 1990-11-20 | Uniroyal Chemical Company, Inc. | Substituted triazines |
| US5118807A (en) * | 1989-10-13 | 1992-06-02 | Uniroyal Chemical Company, Inc. | N-alkyl-p-quinonediimino triazine compounds |
| US5208280A (en) * | 1989-10-13 | 1993-05-04 | Uniroyal Chemical Company, Inc. | Elastomers and tire with N-alkyl-p-quinonediimino triazine stabilizers |
| US5126385A (en) * | 1990-03-20 | 1992-06-30 | Uniroyal Chemical Company, Inc. | Chloropyrimidines and chlorotriazines as rubber-to-metal adhesion promoters |
| BE1009558A5 (fr) * | 1994-03-24 | 1997-05-06 | Clariant Finance Bvi Ltd | Derives de la s-triazine, leur preparation et leur utilisation comme absorbeurs uv. |
| US6063873A (en) * | 1997-12-31 | 2000-05-16 | Bridgestone Corporation | Process to scavenge amines in polymeric compounds by treatment with triazine derivatives, and compositions therefrom |
| US6235819B1 (en) * | 1997-12-31 | 2001-05-22 | Bridgestone Corporation | Process to scavenge amines in polymeric compounds by treatment with triazine derivatives and compositions therefrom |
| DE102007057133A1 (de) * | 2007-11-28 | 2009-06-04 | Robert Bosch Gmbh | Wischgummi für Scheibenwischer |
| CA2917177C (en) | 2013-07-16 | 2022-07-12 | Basf Se | Herbicidal azines |
| CN106458937A (zh) | 2014-04-11 | 2017-02-22 | 巴斯夫欧洲公司 | 作为除草剂的二氨基三嗪衍生物 |
| WO2015162166A1 (en) * | 2014-04-23 | 2015-10-29 | Basf Se | Diaminotriazine compounds and their use as herbicides |
| CN112759557B (zh) * | 2019-11-04 | 2023-12-29 | 圣奥化学科技有限公司 | 具有抗老化和耐变色功效的化合物及其制备方法 |
| CN114105895B (zh) * | 2020-08-28 | 2025-06-13 | 圣奥化学科技有限公司 | 对苯二胺类化合物、其制备方法及应用 |
-
0
- BE BE793389D patent/BE793389A/xx not_active IP Right Cessation
-
1971
- 1971-12-27 DE DE2164800A patent/DE2164800C3/de not_active Expired
-
1972
- 1972-12-11 ZA ZA728736A patent/ZA728736B/xx unknown
- 1972-12-12 CH CH1803972A patent/CH583761A5/xx not_active IP Right Cessation
- 1972-12-12 HU HUDE800A patent/HU167257B/hu unknown
- 1972-12-19 US US00316565A patent/US3828002A/en not_active Expired - Lifetime
- 1972-12-19 ES ES409786A patent/ES409786A1/es not_active Expired
- 1972-12-21 DK DK641972A patent/DK141404C/da not_active IP Right Cessation
- 1972-12-21 CS CS8856A patent/CS178121B2/cs unknown
- 1972-12-21 NL NLAANVRAGE7217445,A patent/NL179817C/xx not_active IP Right Cessation
- 1972-12-22 IL IL41151A patent/IL41151A/xx unknown
- 1972-12-22 AU AU50485/72A patent/AU472715B2/en not_active Expired
- 1972-12-22 IT IT55001/72A patent/IT974295B/it active
- 1972-12-22 AT AT1100772A patent/AT332641B/de not_active IP Right Cessation
- 1972-12-23 PL PL1972159810A patent/PL82475B1/pl unknown
- 1972-12-27 GB GB5960972A patent/GB1412610A/en not_active Expired
- 1972-12-27 CA CA159,983A patent/CA978530A/en not_active Expired
- 1972-12-27 AR AR245860A patent/AR197970A1/es active
- 1972-12-27 DD DD167920A patent/DD102708A5/xx unknown
- 1972-12-27 FR FR7246429A patent/FR2167130A5/fr not_active Expired
- 1972-12-27 JP JP734316A patent/JPS5743566B2/ja not_active Expired
- 1972-12-27 BR BR9176/72A patent/BR7209176D0/pt unknown
-
1973
- 1973-04-30 IN IN1009/CAL/73A patent/IN138951B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS178121B2 (show.php) | 1977-08-31 |
| ATA1100772A (de) | 1976-01-15 |
| HU167257B (show.php) | 1975-09-27 |
| AU472715B2 (en) | 1974-06-27 |
| JPS5743566B2 (show.php) | 1982-09-16 |
| DK141404C (da) | 1980-09-01 |
| AT332641B (de) | 1976-10-11 |
| DE2164800B2 (de) | 1977-11-03 |
| ES409786A1 (es) | 1976-03-16 |
| AU5048572A (en) | 1974-06-27 |
| CA978530A (en) | 1975-11-25 |
| DK141404B (da) | 1980-03-10 |
| PL82475B1 (show.php) | 1975-10-31 |
| JPS4876936A (show.php) | 1973-10-16 |
| BE793389A (fr) | 1973-06-27 |
| GB1412610A (en) | 1975-11-05 |
| NL179817C (nl) | 1986-11-17 |
| US3828002A (en) | 1974-08-06 |
| IT974295B (it) | 1974-06-20 |
| NL7217445A (show.php) | 1973-06-29 |
| BR7209176D0 (pt) | 1973-09-25 |
| AR197970A1 (es) | 1974-05-24 |
| IN138951B (show.php) | 1976-04-17 |
| IL41151A (en) | 1978-01-31 |
| DE2164800A1 (de) | 1973-07-12 |
| IL41151A0 (en) | 1973-02-28 |
| NL179817B (nl) | 1986-06-16 |
| CH583761A5 (show.php) | 1977-01-14 |
| DD102708A5 (show.php) | 1973-12-20 |
| ZA728736B (en) | 1974-07-31 |
| FR2167130A5 (show.php) | 1973-08-17 |
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