DE1543843B1 - 4,4'-Bis-(alpha,alpha-dimethylbenzyl)-diphenylamin,dessen Herstellung und Verwendung als Alterungsschutzmittel - Google Patents
4,4'-Bis-(alpha,alpha-dimethylbenzyl)-diphenylamin,dessen Herstellung und Verwendung als AlterungsschutzmittelInfo
- Publication number
- DE1543843B1 DE1543843B1 DE19661543843 DE1543843A DE1543843B1 DE 1543843 B1 DE1543843 B1 DE 1543843B1 DE 19661543843 DE19661543843 DE 19661543843 DE 1543843 A DE1543843 A DE 1543843A DE 1543843 B1 DE1543843 B1 DE 1543843B1
- Authority
- DE
- Germany
- Prior art keywords
- diphenylamine
- alpha
- bis
- dimethylbenzyl
- product
- 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.)
- Withdrawn
Links
- UJAWGGOCYUPCPS-UHFFFAOYSA-N 4-(2-phenylpropan-2-yl)-n-[4-(2-phenylpropan-2-yl)phenyl]aniline Chemical compound C=1C=C(NC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 UJAWGGOCYUPCPS-UHFFFAOYSA-N 0.000 title claims description 8
- 230000003712 anti-aging effect Effects 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 27
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229920001194 natural rubber Polymers 0.000 claims description 4
- 229920003051 synthetic elastomer Polymers 0.000 claims description 4
- 229920003052 natural elastomer Polymers 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000005061 synthetic rubber Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 26
- 239000003223 protective agent Substances 0.000 description 9
- 229920001971 elastomer Polymers 0.000 description 8
- 239000005060 rubber Substances 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 1
- BRWSDEFCJGIRLV-UHFFFAOYSA-N 4-(1-phenylethyl)-n-[4-(1-phenylethyl)phenyl]aniline Chemical compound C=1C=C(NC=2C=CC(=CC=2)C(C)C=2C=CC=CC=2)C=CC=1C(C)C1=CC=CC=C1 BRWSDEFCJGIRLV-UHFFFAOYSA-N 0.000 description 1
- GFQRVGKVOSEDJX-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCC(O)=O.[O-2].O.S.[Zn+2] Chemical compound CCCCCCCCCCCCCCCCCC(O)=O.[O-2].O.S.[Zn+2] GFQRVGKVOSEDJX-UHFFFAOYSA-N 0.000 description 1
- UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- -1 acetic acid Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WGARMULIELDQEH-UHFFFAOYSA-N n-cyclohexyl-1,3-benzothiazole-2-sulfinamide Chemical compound N=1C2=CC=CC=C2SC=1S(=O)NC1CCCCC1 WGARMULIELDQEH-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000004525 petroleum distillation Methods 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
-
- 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
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR43844A FR1472132A (fr) | 1965-12-27 | 1965-12-27 | Procédé de fabrication de bis (phénylisopropylidène-4 phényl) amine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1543843B1 true DE1543843B1 (de) | 1972-04-27 |
Family
ID=8596920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543843 Withdrawn DE1543843B1 (de) | 1965-12-27 | 1966-12-27 | 4,4'-Bis-(alpha,alpha-dimethylbenzyl)-diphenylamin,dessen Herstellung und Verwendung als Alterungsschutzmittel |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE691826A (enExample) |
| CH (1) | CH468342A (enExample) |
| DE (1) | DE1543843B1 (enExample) |
| FR (1) | FR1472132A (enExample) |
| NL (1) | NL6617794A (enExample) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2943112A (en) * | 1957-11-06 | 1960-06-28 | Pennsalt Chemicals Corp | Alkylation of diphenylamine |
| NL6507710A (enExample) * | 1964-06-16 | 1965-12-17 |
-
1965
- 1965-12-27 FR FR43844A patent/FR1472132A/fr not_active Expired
-
1966
- 1966-12-19 NL NL6617794A patent/NL6617794A/xx unknown
- 1966-12-27 DE DE19661543843 patent/DE1543843B1/de not_active Withdrawn
- 1966-12-27 BE BE691826D patent/BE691826A/xx unknown
- 1966-12-27 CH CH1852366A patent/CH468342A/fr unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2943112A (en) * | 1957-11-06 | 1960-06-28 | Pennsalt Chemicals Corp | Alkylation of diphenylamine |
| NL6507710A (enExample) * | 1964-06-16 | 1965-12-17 | ||
| GB1049618A (en) * | 1964-06-16 | 1966-11-30 | Bayer Ag | Lubricants |
| DE1243811B (de) * | 1964-06-16 | 1967-07-06 | Bayer Ag | Schmierstoffzusatzmittel |
Also Published As
| Publication number | Publication date |
|---|---|
| CH468342A (fr) | 1969-02-15 |
| BE691826A (enExample) | 1967-06-27 |
| FR1472132A (fr) | 1967-03-10 |
| NL6617794A (enExample) | 1967-06-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EHJ | Ceased/non-payment of the annual fee |