DE2520725C3 - UV-Stabilisator für Polymere - Google Patents
UV-Stabilisator für PolymereInfo
- Publication number
- DE2520725C3 DE2520725C3 DE2520725A DE2520725A DE2520725C3 DE 2520725 C3 DE2520725 C3 DE 2520725C3 DE 2520725 A DE2520725 A DE 2520725A DE 2520725 A DE2520725 A DE 2520725A DE 2520725 C3 DE2520725 C3 DE 2520725C3
- Authority
- DE
- Germany
- Prior art keywords
- nickel
- complex
- nbc
- bis
- complexes
- 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
- 229920000642 polymer Polymers 0.000 title claims description 20
- 239000012963 UV stabilizer Substances 0.000 title claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- -1 cyclic secondary amine Chemical class 0.000 description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 11
- 239000004743 Polypropylene Substances 0.000 description 11
- 230000015556 catabolic process Effects 0.000 description 11
- 238000006731 degradation reaction Methods 0.000 description 11
- 229920001155 polypropylene Polymers 0.000 description 11
- 238000002845 discoloration Methods 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- WQYFETFRIRDUPJ-UHFFFAOYSA-N 2-[2-hydroxy-5-(2,4,4-trimethylpentan-2-yl)phenyl]sulfanyl-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(SC=2C(=CC=C(C=2)C(C)(C)CC(C)(C)C)O)=C1 WQYFETFRIRDUPJ-UHFFFAOYSA-N 0.000 description 5
- 230000032683 aging Effects 0.000 description 5
- LNQMUHQVKMATKD-UHFFFAOYSA-N butan-1-amine;nickel Chemical compound [Ni].CCCCN LNQMUHQVKMATKD-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 3
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 3
- 150000002815 nickel Chemical group 0.000 description 3
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- FSOIDCQVEPKDOS-UHFFFAOYSA-L [Ni+2].OC1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 Chemical compound [Ni+2].OC1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 FSOIDCQVEPKDOS-UHFFFAOYSA-L 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical group NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical class CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical class CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical class CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003139 primary aliphatic amines Chemical class 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- WWNBZGLDODTKEM-UHFFFAOYSA-N sulfanylidenenickel Chemical compound [Ni]=S WWNBZGLDODTKEM-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- PAYGMTHUILNIJW-UHFFFAOYSA-N 1-(2-hydroxyethyl)-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(CCO)C(=O)NC1=O PAYGMTHUILNIJW-UHFFFAOYSA-N 0.000 description 1
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical class CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 description 1
- WMEMJQZQRVGGKJ-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxy-n-octylbenzamide Chemical compound CCCCCCCCNC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WMEMJQZQRVGGKJ-UHFFFAOYSA-N 0.000 description 1
- DGZQOKRGJUFPQC-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzamide Chemical class CC(C)(C)C1=CC(C(N)=O)=CC(C(C)(C)C)=C1O DGZQOKRGJUFPQC-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-L 3-(2-carboxylatoethylsulfanyl)propanoate Chemical compound [O-]C(=O)CCSCCC([O-])=O ODJQKYXPKWQWNK-UHFFFAOYSA-L 0.000 description 1
- GUCPYIYFQVTFSI-UHFFFAOYSA-N 4-methoxybenzamide Chemical class COC1=CC=C(C(N)=O)C=C1 GUCPYIYFQVTFSI-UHFFFAOYSA-N 0.000 description 1
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical group CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 1
- ORAWFNKFUWGRJG-UHFFFAOYSA-N Docosanamide Chemical class CCCCCCCCCCCCCCCCCCCCCC(N)=O ORAWFNKFUWGRJG-UHFFFAOYSA-N 0.000 description 1
- AOMUHOFOVNGZAN-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)dodecanamide Chemical group CCCCCCCCCCCC(=O)N(CCO)CCO AOMUHOFOVNGZAN-UHFFFAOYSA-N 0.000 description 1
- QZXSMBBFBXPQHI-UHFFFAOYSA-N N-(dodecanoyl)ethanolamine Chemical compound CCCCCCCCCCCC(=O)NCCO QZXSMBBFBXPQHI-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- HZUJFPFEXQTAEL-UHFFFAOYSA-N azanylidynenickel Chemical compound [N].[Ni] HZUJFPFEXQTAEL-UHFFFAOYSA-N 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- RWWXQVFXNZNKMA-UHFFFAOYSA-N cyclohexanamine;nickel Chemical compound [Ni].NC1CCCCC1 RWWXQVFXNZNKMA-UHFFFAOYSA-N 0.000 description 1
- 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229940116335 lauramide Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- LOTWRKOXHCMWDB-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)benzamide Chemical compound OCCN(CCO)C(=O)C1=CC=CC=C1 LOTWRKOXHCMWDB-UHFFFAOYSA-N 0.000 description 1
- BAMUPQJDKBGDPU-UHFFFAOYSA-N n-(2-hydroxyethyl)formamide Chemical group OCCNC=O BAMUPQJDKBGDPU-UHFFFAOYSA-N 0.000 description 1
- FWFWEABKGWAUSN-UHFFFAOYSA-N n-(hydroxymethyl)docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)NCO FWFWEABKGWAUSN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical class C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 description 1
- CLQUXJZJDVHHMG-UHFFFAOYSA-N nickel;phenol Chemical compound [Ni].OC1=CC=CC=C1.OC1=CC=CC=C1 CLQUXJZJDVHHMG-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- LTHCSWBWNVGEFE-UHFFFAOYSA-N octanamide Chemical class CCCCCCCC(N)=O LTHCSWBWNVGEFE-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- DGMKFQYCZXERLX-UHFFFAOYSA-N proglumide Chemical compound CCCN(CCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=CC=C1 DGMKFQYCZXERLX-UHFFFAOYSA-N 0.000 description 1
- 229960003857 proglumide Drugs 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 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
- C08K5/20—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
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
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)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/479,017 US3932324A (en) | 1974-06-13 | 1974-06-13 | Light stabilizer compositions for polymers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2520725A1 DE2520725A1 (de) | 1976-01-02 |
| DE2520725B2 DE2520725B2 (de) | 1979-01-18 |
| DE2520725C3 true DE2520725C3 (de) | 1979-09-27 |
Family
ID=23902316
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2520725A Expired DE2520725C3 (de) | 1974-06-13 | 1975-05-09 | UV-Stabilisator für Polymere |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3932324A (enExample) |
| JP (1) | JPS548498B2 (enExample) |
| AR (1) | AR206225A1 (enExample) |
| BE (1) | BE830150A (enExample) |
| BR (1) | BR7503656A (enExample) |
| CA (1) | CA1056149A (enExample) |
| DE (1) | DE2520725C3 (enExample) |
| FR (1) | FR2274642A1 (enExample) |
| GB (1) | GB1484225A (enExample) |
| IT (1) | IT1035784B (enExample) |
| NL (1) | NL159695B (enExample) |
| ZA (1) | ZA752734B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4211692A (en) * | 1976-03-29 | 1980-07-08 | Standard Oil Company (Indiana) | Extrusion coating compositions for woven and non-woven polyolefin substrates and articles thereof |
| US4124725A (en) * | 1977-05-16 | 1978-11-07 | Riker Laboratories, Inc. | Anti-inflammatory method |
| US4219501A (en) * | 1977-05-16 | 1980-08-26 | Riker Laboratories, Inc. | Anti-inflammatory method |
| US4165383A (en) * | 1977-05-16 | 1979-08-21 | Riker Laboratories, Inc. | Anti-inflammatory method |
| US4128664A (en) * | 1977-05-16 | 1978-12-05 | Riker Laboratories, Inc. | Substituted benzamides as anti-inflammatory agents |
| US4130666A (en) * | 1977-05-16 | 1978-12-19 | Riker Laboratories, Inc. | Anti-inflammatory method |
| US4180514A (en) * | 1978-02-09 | 1979-12-25 | Phillips Petroleum Company | Adhesion promoter and method of preparation |
| JPS6267536A (ja) * | 1985-09-19 | 1987-03-27 | Konishiroku Photo Ind Co Ltd | 写真要素 |
| IT1311895B1 (it) * | 1999-03-12 | 2002-03-20 | Sir Ind Spa | Miscele di b-idrossialchilammidi e loro impiego come agentireticolanti per la preparazione di vernici in polvere. |
| DE10053194A1 (de) * | 2000-10-26 | 2002-05-16 | Ems Chemie Ag | ß-Hydroxyalkylamide, Verfahren zu ihrer Herstellung und deren Verwendung |
| JP6283477B2 (ja) * | 2012-06-25 | 2018-02-21 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ | アミド成分を含むフォトレジスト |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1137929A (en) * | 1966-10-19 | 1968-12-27 | Distrene Ltd | Alkanolamide-containing antistatic agent compositions for polymers |
| JPS5142617B2 (enExample) * | 1971-11-12 | 1976-11-17 | ||
| US3790517A (en) * | 1972-08-07 | 1974-02-05 | Mitsui Petrochemical Ind | Crystalline polypropylene compositions |
-
1974
- 1974-06-13 US US05/479,017 patent/US3932324A/en not_active Expired - Lifetime
-
1975
- 1975-01-01 AR AR258710A patent/AR206225A1/es active
- 1975-04-25 CA CA225,510A patent/CA1056149A/en not_active Expired
- 1975-04-28 ZA ZA00752734A patent/ZA752734B/xx unknown
- 1975-05-02 GB GB18517/75A patent/GB1484225A/en not_active Expired
- 1975-05-09 DE DE2520725A patent/DE2520725C3/de not_active Expired
- 1975-05-19 IT IT49668/75A patent/IT1035784B/it active
- 1975-06-10 BR BR4687/75D patent/BR7503656A/pt unknown
- 1975-06-12 BE BE157257A patent/BE830150A/xx unknown
- 1975-06-12 NL NL7507010.A patent/NL159695B/xx not_active IP Right Cessation
- 1975-06-13 JP JP7098175A patent/JPS548498B2/ja not_active Expired
- 1975-06-13 FR FR7518641A patent/FR2274642A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2520725B2 (de) | 1979-01-18 |
| FR2274642A1 (fr) | 1976-01-09 |
| JPS548498B2 (enExample) | 1979-04-16 |
| NL7507010A (nl) | 1975-12-16 |
| AU8066975A (en) | 1976-11-04 |
| BE830150A (fr) | 1975-12-12 |
| DE2520725A1 (de) | 1976-01-02 |
| NL159695B (nl) | 1979-03-15 |
| IT1035784B (it) | 1979-10-20 |
| ZA752734B (en) | 1976-04-28 |
| AR206225A1 (es) | 1976-07-07 |
| US3932324A (en) | 1976-01-13 |
| FR2274642B1 (enExample) | 1978-09-01 |
| GB1484225A (en) | 1977-09-01 |
| CA1056149A (en) | 1979-06-12 |
| BR7503656A (pt) | 1976-06-29 |
| JPS5136241A (enExample) | 1976-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: SPOTT, G., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |