DE1907403A1 - Neue asymmetrische Diaryloxalamide und deren Verwendung als Stabilisatoren und UV-absorber fuer Kunststoffe - Google Patents
Neue asymmetrische Diaryloxalamide und deren Verwendung als Stabilisatoren und UV-absorber fuer KunststoffeInfo
- Publication number
- DE1907403A1 DE1907403A1 DE19691907403 DE1907403A DE1907403A1 DE 1907403 A1 DE1907403 A1 DE 1907403A1 DE 19691907403 DE19691907403 DE 19691907403 DE 1907403 A DE1907403 A DE 1907403A DE 1907403 A1 DE1907403 A1 DE 1907403A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- diaryloxalamides
- mole
- compounds
- aryl
- 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- Withdrawn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
- 239000004033 plastic Substances 0.000 title claims description 9
- 229920003023 plastic Polymers 0.000 title claims description 9
- 239000003381 stabilizer Substances 0.000 title claims description 6
- 239000006096 absorbing agent Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 19
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 235000006408 oxalic acid Nutrition 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 230000009435 amidation Effects 0.000 claims description 2
- 238000007112 amidation reaction Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000006641 stabilisation Effects 0.000 claims description 2
- 238000011105 stabilization Methods 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000002184 metal Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 150000003606 tin compounds Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 13
- -1 Polyethylene Polymers 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FCKXGFANXSHGAW-DTXPUJKBSA-N (2s)-n,n'-bis[(2s)-1-(2-chloro-4-nitroanilino)-1-oxo-3-phenylpropan-2-yl]-2-hydroxybutanediamide Chemical compound C([C@H](NC(=O)C[C@H](O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NC=1C(=CC(=CC=1)[N+]([O-])=O)Cl)C(=O)NC=1C(=CC(=CC=1)[N+]([O-])=O)Cl)C1=CC=CC=C1 FCKXGFANXSHGAW-DTXPUJKBSA-N 0.000 description 1
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- JMWUYEFBFUCSAK-UHFFFAOYSA-L nickel(2+);octadecanoate Chemical compound [Ni+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JMWUYEFBFUCSAK-UHFFFAOYSA-L 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH237168A CH511806A (de) | 1968-02-19 | 1968-02-19 | Vunfahren zur Herstellung neuer asymmetrischer Diaryloxalamide und deren Verwendung als Stabilisatoren und UV-Absorder für Kunststoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1907403A1 true DE1907403A1 (de) | 1969-10-02 |
Family
ID=4232197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691907403 Withdrawn DE1907403A1 (de) | 1968-02-19 | 1969-02-14 | Neue asymmetrische Diaryloxalamide und deren Verwendung als Stabilisatoren und UV-absorber fuer Kunststoffe |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5028425B1 (en)) |
| AT (1) | AT287682B (en)) |
| BE (1) | BE728592A (en)) |
| CA (1) | CA989865A (en)) |
| CH (1) | CH511806A (en)) |
| DE (1) | DE1907403A1 (en)) |
| ES (1) | ES363735A1 (en)) |
| FR (1) | FR2002161A1 (en)) |
| GB (1) | GB1234128A (en)) |
| MY (1) | MY7400238A (en)) |
| NL (1) | NL6902607A (en)) |
| SE (1) | SE369519B (en)) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0116931A1 (de) * | 1983-02-18 | 1984-08-29 | BASF Aktiengesellschaft | Oxalsäurediarylamide und deren Verwendung als UV-Absorber und damit ausgerüstete polymere Substrate |
| EP0138757A1 (de) * | 1983-08-26 | 1985-04-24 | Ciba-Geigy Ag | Oxalsäureanilide |
| EP0712856A1 (fr) * | 1994-11-17 | 1996-05-22 | L'oreal | Nouveaux filtres solaires, compositions cosmétiques photoprotectrices les contenant et utilisations |
| EP2955201A1 (de) | 2014-06-11 | 2015-12-16 | Covestro Deutschland AG | Glasfaserverstärkte Polycarbonat-Zusammensetzungen |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE1003209A3 (fr) * | 1989-02-22 | 1992-01-14 | Sandoz Sa | Nouveau procede de teinture des fibres de polyamides. |
| JP5553437B2 (ja) * | 2010-02-22 | 2014-07-16 | 株式会社Ａｄｅｋａ | 耐候性塩化ビニル系樹脂組成物 |
| CN102702012A (zh) * | 2012-06-19 | 2012-10-03 | 南通惠康国际企业有限公司 | 光稳定剂n-(2-乙基苯基)-n’-(2-乙氧基-5-叔丁基苯基)-草酸二胺的制备方法 |
-
1968
- 1968-02-19 CH CH237168A patent/CH511806A/de not_active IP Right Cessation
-
1969
- 1969-02-03 AT AT104369A patent/AT287682B/de active
- 1969-02-12 JP JP981169A patent/JPS5028425B1/ja active Pending
- 1969-02-14 DE DE19691907403 patent/DE1907403A1/de not_active Withdrawn
- 1969-02-15 CA CA043,049A patent/CA989865A/en not_active Expired
- 1969-02-17 GB GB1234128D patent/GB1234128A/en not_active Expired
- 1969-02-17 FR FR6903864A patent/FR2002161A1/fr not_active Withdrawn
- 1969-02-17 ES ES363735A patent/ES363735A1/es not_active Expired
- 1969-02-18 BE BE728592D patent/BE728592A/xx not_active IP Right Cessation
- 1969-02-18 SE SE222169A patent/SE369519B/xx unknown
- 1969-02-19 NL NL6902607A patent/NL6902607A/xx unknown
-
1974
- 1974-12-30 MY MY7400238A patent/MY7400238A/xx unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0116931A1 (de) * | 1983-02-18 | 1984-08-29 | BASF Aktiengesellschaft | Oxalsäurediarylamide und deren Verwendung als UV-Absorber und damit ausgerüstete polymere Substrate |
| EP0138757A1 (de) * | 1983-08-26 | 1985-04-24 | Ciba-Geigy Ag | Oxalsäureanilide |
| TR23746A (tr) * | 1983-08-26 | 1990-08-01 | Ciba Geigy Ag | Oksalik asit anilidler. |
| EP0712856A1 (fr) * | 1994-11-17 | 1996-05-22 | L'oreal | Nouveaux filtres solaires, compositions cosmétiques photoprotectrices les contenant et utilisations |
| FR2727114A1 (fr) * | 1994-11-17 | 1996-05-24 | Oreal | Nouveaux filtres solaires, compositions cosmetiques photoprotectrices les contenant et utilisations |
| US5587151A (en) * | 1994-11-17 | 1996-12-24 | L'oreal | Photoprotective/cosmetic compositions comprising oxanilido-substituted polyorganosiloxanes/polyorganosilanes |
| EP2955201A1 (de) | 2014-06-11 | 2015-12-16 | Covestro Deutschland AG | Glasfaserverstärkte Polycarbonat-Zusammensetzungen |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6902607A (en)) | 1969-08-21 |
| AT287682B (de) | 1971-02-10 |
| FR2002161A1 (en)) | 1969-10-17 |
| BE728592A (en)) | 1969-08-18 |
| GB1234128A (en)) | 1971-06-03 |
| SE369519B (en)) | 1974-09-02 |
| CA989865A (en) | 1976-05-25 |
| CH511806A (de) | 1971-08-31 |
| MY7400238A (en) | 1974-12-31 |
| ES363735A1 (es) | 1971-07-16 |
| JPS5028425B1 (en)) | 1975-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |