DE3218172A1 - Polyalkyldiazaspirodecanderivate, verfahren zu ihrer herstellung und ihre verwendung als stabilisatoren - Google Patents
Polyalkyldiazaspirodecanderivate, verfahren zu ihrer herstellung und ihre verwendung als stabilisatorenInfo
- Publication number
- DE3218172A1 DE3218172A1 DE19823218172 DE3218172A DE3218172A1 DE 3218172 A1 DE3218172 A1 DE 3218172A1 DE 19823218172 DE19823218172 DE 19823218172 DE 3218172 A DE3218172 A DE 3218172A DE 3218172 A1 DE3218172 A1 DE 3218172A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- alkyl
- hydrogen
- group
- substituted
- 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- Withdrawn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
- 239000003381 stabilizer Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 24
- -1 2,3-dihydroxypropyl Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000002118 epoxides Chemical class 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- 229920000193 polymethacrylate Polymers 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 229920001059 synthetic polymer Polymers 0.000 claims 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 229920000058 polyacrylate Polymers 0.000 claims 1
- 229920000098 polyolefin Polymers 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 claims 1
- 238000011105 stabilization Methods 0.000 claims 1
- 239000004577 thatch Substances 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 abstract description 2
- 229920000620 organic polymer Polymers 0.000 abstract description 2
- 238000010525 oxidative degradation reaction Methods 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-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
- 239000002253 acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000004904 UV filter Substances 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000463 material 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
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DTIGELFFJROSDC-UHFFFAOYSA-N tetradecane-3,12-dione Chemical compound CCC(=O)CCCCCCCCC(=O)CC DTIGELFFJROSDC-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823218172 DE3218172A1 (de) | 1982-05-14 | 1982-05-14 | Polyalkyldiazaspirodecanderivate, verfahren zu ihrer herstellung und ihre verwendung als stabilisatoren |
| US06/491,609 US4526966A (en) | 1982-05-14 | 1983-05-04 | Polyalkyldiazaspirodecane derivatives |
| ZA833363A ZA833363B (en) | 1982-05-14 | 1983-05-11 | Polyalkyldiazaspirodecane derivatives,a process for their preparation and their use as stabilizers |
| AT83104618T ATE24179T1 (de) | 1982-05-14 | 1983-05-11 | Polyalkyldiazaspirodecanderivate, verfahren zu ihrer herstellung und ihre verwendung als stabilisatoren. |
| EP83104618A EP0094605B1 (de) | 1982-05-14 | 1983-05-11 | Polyalkyldiazaspirodecanderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Stabilisatoren |
| DE8383104618T DE3368263D1 (en) | 1982-05-14 | 1983-05-11 | Polyalkyldiazaspirodecane derivatives, process for their preparation and their use as stabilizers |
| AU14590/83A AU558439B2 (en) | 1982-05-14 | 1983-05-13 | Polyackyldiazaspirodecane derivatives |
| CA000428064A CA1247095A (en) | 1982-05-14 | 1983-05-13 | Polyalkyldiazaspirodecane derivatives, a process for their preparation and their use as stabilizers |
| BR8302528A BR8302528A (pt) | 1982-05-14 | 1983-05-13 | Derivados de polialquildiazaspirodecano, processo para a sua preparacao, sua aplicacao, processo para estabilizar polimeros sinteticos, e polimeros sinteticos, estabilizados contra a decomposicao por ultravioleta |
| JP58082874A JPS58206594A (ja) | 1982-05-14 | 1983-05-13 | ポリアルキルジアザスピロデカン誘導体、その製造方法およびその用途 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823218172 DE3218172A1 (de) | 1982-05-14 | 1982-05-14 | Polyalkyldiazaspirodecanderivate, verfahren zu ihrer herstellung und ihre verwendung als stabilisatoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3218172A1 true DE3218172A1 (de) | 1983-11-17 |
Family
ID=6163582
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823218172 Withdrawn DE3218172A1 (de) | 1982-05-14 | 1982-05-14 | Polyalkyldiazaspirodecanderivate, verfahren zu ihrer herstellung und ihre verwendung als stabilisatoren |
| DE8383104618T Expired DE3368263D1 (en) | 1982-05-14 | 1983-05-11 | Polyalkyldiazaspirodecane derivatives, process for their preparation and their use as stabilizers |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8383104618T Expired DE3368263D1 (en) | 1982-05-14 | 1983-05-11 | Polyalkyldiazaspirodecane derivatives, process for their preparation and their use as stabilizers |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4526966A (https=) |
| EP (1) | EP0094605B1 (https=) |
| JP (1) | JPS58206594A (https=) |
| AT (1) | ATE24179T1 (https=) |
| AU (1) | AU558439B2 (https=) |
| BR (1) | BR8302528A (https=) |
| CA (1) | CA1247095A (https=) |
| DE (2) | DE3218172A1 (https=) |
| ZA (1) | ZA833363B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3217734A1 (de) * | 1982-05-12 | 1983-11-17 | Hoechst Ag, 6230 Frankfurt | Polyalkyldiazaspirodecanylessigsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als lichtschutzmittel fuer organische polymere |
| DE3524542A1 (de) * | 1985-07-10 | 1987-01-22 | Hoechst Ag | 1-oxa-3-oxo-4,8-diaza-spiro-(4,5)decan- verbindungen |
| IT1191830B (it) * | 1986-01-13 | 1988-03-23 | Ausimont Spa | Derivati della morfolina contenti gruppi piperidinici sostituiti e loro impiego come stabilizzanti |
| GB8808433D0 (en) * | 1988-04-11 | 1988-05-11 | Merck Sharp & Dohme | Therapeutic agents |
| US5116976A (en) * | 1990-07-17 | 1992-05-26 | Atochem North America, Inc | Hindered amine light stabilizer hydrazides |
| KR20010050085A (ko) * | 1999-08-18 | 2001-06-15 | 잔디해머,한스루돌프하우스 | 신규한 입체 장애 아민 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3364220A (en) * | 1963-11-13 | 1968-01-16 | Colgate Palmolive Co | Heterocyclicaminoalkylguanidines |
| DE2834962A1 (de) * | 1978-08-10 | 1980-02-21 | Hoechst Ag | Verfahren zur herstellung von azaspirodecanen |
| EP0017617A3 (de) * | 1979-03-27 | 1980-10-29 | Ciba-Geigy Ag | Polyalkylpiperidin-spirooxazolone, ihre Verwendung als Lichtschutzmittel und mit diesen Verbindungen stabilisierter Kunststoff |
| JPS5611932A (en) * | 1979-07-12 | 1981-02-05 | Adeka Argus Chem Co Ltd | Stabilized polymer composition |
| DE2933732A1 (de) * | 1979-08-21 | 1981-03-26 | Hoechst Ag, 65929 Frankfurt | Alkylierte diazaspirodecane, ihre herstellung und verwendung als lichtschutzmittel |
-
1982
- 1982-05-14 DE DE19823218172 patent/DE3218172A1/de not_active Withdrawn
-
1983
- 1983-05-04 US US06/491,609 patent/US4526966A/en not_active Expired - Lifetime
- 1983-05-11 AT AT83104618T patent/ATE24179T1/de active
- 1983-05-11 ZA ZA833363A patent/ZA833363B/xx unknown
- 1983-05-11 DE DE8383104618T patent/DE3368263D1/de not_active Expired
- 1983-05-11 EP EP83104618A patent/EP0094605B1/de not_active Expired
- 1983-05-13 CA CA000428064A patent/CA1247095A/en not_active Expired
- 1983-05-13 BR BR8302528A patent/BR8302528A/pt not_active IP Right Cessation
- 1983-05-13 JP JP58082874A patent/JPS58206594A/ja active Granted
- 1983-05-13 AU AU14590/83A patent/AU558439B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU1459083A (en) | 1983-11-17 |
| US4526966A (en) | 1985-07-02 |
| ZA833363B (en) | 1984-02-29 |
| JPS58206594A (ja) | 1983-12-01 |
| CA1247095A (en) | 1988-12-20 |
| EP0094605B1 (de) | 1986-12-10 |
| ATE24179T1 (de) | 1986-12-15 |
| EP0094605A2 (de) | 1983-11-23 |
| DE3368263D1 (en) | 1987-01-22 |
| JPH0469158B2 (https=) | 1992-11-05 |
| EP0094605A3 (en) | 1984-09-05 |
| BR8302528A (pt) | 1984-01-17 |
| AU558439B2 (en) | 1987-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |