FR2335519A1 - Piperidinol phosphorous esters used to stabilise polymers - against thermo-oxidation, are hydrolysis resistant and have good colour properties - Google Patents
Piperidinol phosphorous esters used to stabilise polymers - against thermo-oxidation, are hydrolysis resistant and have good colour propertiesInfo
- Publication number
- FR2335519A1 FR2335519A1 FR7638048A FR7638048A FR2335519A1 FR 2335519 A1 FR2335519 A1 FR 2335519A1 FR 7638048 A FR7638048 A FR 7638048A FR 7638048 A FR7638048 A FR 7638048A FR 2335519 A1 FR2335519 A1 FR 2335519A1
- Authority
- FR
- France
- Prior art keywords
- alkyl
- phenyl
- polymers
- aralkyl
- piperidinol
- 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.)
- Granted
Links
- -1 Piperidinol phosphorous esters Chemical class 0.000 title abstract 4
- 230000007062 hydrolysis Effects 0.000 title abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 title abstract 2
- 229920000642 polymer Polymers 0.000 title abstract 2
- 238000007254 oxidation reaction Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- 239000004743 Polypropylene Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 238000002845 discoloration Methods 0.000 abstract 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 1
- 229920001903 high density polyethylene Polymers 0.000 abstract 1
- 239000004700 high-density polyethylene Substances 0.000 abstract 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 abstract 1
- 229920001684 low density polyethylene Polymers 0.000 abstract 1
- 239000004702 low-density polyethylene Substances 0.000 abstract 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical class ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 abstract 1
- 239000011368 organic material Substances 0.000 abstract 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229920001155 polypropylene Polymers 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 1
- 239000004800 polyvinyl chloride Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/529—Esters containing heterocyclic rings not representing cyclic esters of phosphoric or phosphorous acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/59—Hydrogenated pyridine rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Phosphorous esters of piperidinols of formula I and acid addn. salts are new. In (I), n=1 or 2; R1,R2 and R3 are each 1-6C alkyl; R4 is 1-9C alkyl, phenyl, benzyl or phenylethyl, or R3 and R4 together form -(CH2)4- or -(CH2)5-; R5 and R6 are each H or 1-5C alkyl, R7 is 1-12C alkyl, 5-8C cycloalkyl, 6-9C alkylcycloalkyl, 6-10C aryl 7-14C alkaryl or 7-9C aralkyl; R8 is H, Cl, Br, or a radical as listed for R7; R9, if n = 1, is H, Cl, 1-4C alkyl, 5-8C cycloalkyl or 6-9C alkylcycloalkyl or, if n=2, is H, Cl, Br, or a radical as listed for R7. X is H, oxyl, 1-12C alkyl, 3-6C alkenyl, 3-4C alkynyl 2-21C alkoxyalkyl, 7-8C aralkyl, 2,3-epoxypropyl, 1-4C aliphatic acyl gp. or - CH2COOR10, -CH2CHCR11)-OR12, -COOR13 or -CONHR13, where R10 is 1-8C alkyl, 3-6C alkenyl phenyl, 7-8C aralkyl or cyclohexyl; R11 is H, Me or phenyl; R12 is H, 1-18C aliphatic, aromatic, araliphatic or dicyclic acyl gp. where the aromatic pt. may be substd by Cl, 1-4C alkyl, 1-8C alkoxy and/or OH and R13 is 1-12 C alkoxy and/or OH and R13 is 1-12C alkyl, cyclohexyl, phenyl or benzyl. Used as stabilisers for organic material against light induced thermo-oxidn. esp. for polymers e.g. high or low density polyethylene, polypropylene, polyurethanes, PVC, polyestyrene and, copolymers of them. The prod has high resistance to hydrolysis and low discoloration on use.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1650775 | 1975-12-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2335519A1 true FR2335519A1 (en) | 1977-07-15 |
| FR2335519B1 FR2335519B1 (en) | 1979-03-09 |
Family
ID=4417959
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7638048A Granted FR2335519A1 (en) | 1975-12-19 | 1976-12-17 | Piperidinol phosphorous esters used to stabilise polymers - against thermo-oxidation, are hydrolysis resistant and have good colour properties |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5289677A (en) |
| BE (1) | BE849508A (en) |
| DE (1) | DE2656766A1 (en) |
| FR (1) | FR2335519A1 (en) |
| NL (1) | NL7614071A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2417523A1 (en) * | 1978-02-15 | 1979-09-14 | Borg Warner | COMPOSITIONS OF OLEFIN POLYMERS, STABILIZED AGAINST ULTRAVIOLET RADIATION AND HEAT DEGRADATION, CONTAINING A DERIVATIVE OF BIS- (PIPERIDINYL) DIPHOSPHITES OF PENTAERYTHRITOL |
| EP0149259A3 (en) * | 1983-12-29 | 1985-08-07 | Adeka Argus Chemical Co., Ltd. | Alkylidene bisphenol phosphites and phosphates having 2,2,6,6-tetramethyl piperidinyl groups and synthetic resin compositions |
| EP0589842A1 (en) * | 1992-09-25 | 1994-03-30 | Ciba-Geigy Ag | Tetra-N-alkyl-2,2,6,6-tetramethylpiperidin-4-yl-4,4'-diphenyl-bisphosphonites as stabilisers for organic materials |
| EP0601973A1 (en) * | 1992-12-04 | 1994-06-15 | Ciba-Geigy Ag | Oligomeric HALS-phosphite and HALS-phosphonites as stabilizers |
| FR2718742A1 (en) * | 1994-04-13 | 1995-10-20 | Ciba Geigy Ag | Phosphites and phosphoramides of hindered amine light stabilizing compounds useful as stabilizers. |
| FR2720745A1 (en) * | 1994-06-06 | 1995-12-08 | Ciba Geigy Ag | Stabilizing compounds, composition containing them and their use for stabilizing organic materials |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9205308D0 (en) * | 1992-03-11 | 1992-04-22 | Sandoz Ltd | Improvements in or relating to organic compounds |
-
1976
- 1976-12-15 DE DE19762656766 patent/DE2656766A1/en active Pending
- 1976-12-17 NL NL7614071A patent/NL7614071A/en not_active Application Discontinuation
- 1976-12-17 BE BE173350A patent/BE849508A/en unknown
- 1976-12-17 FR FR7638048A patent/FR2335519A1/en active Granted
- 1976-12-20 JP JP15329376A patent/JPS5289677A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2417523A1 (en) * | 1978-02-15 | 1979-09-14 | Borg Warner | COMPOSITIONS OF OLEFIN POLYMERS, STABILIZED AGAINST ULTRAVIOLET RADIATION AND HEAT DEGRADATION, CONTAINING A DERIVATIVE OF BIS- (PIPERIDINYL) DIPHOSPHITES OF PENTAERYTHRITOL |
| EP0149259A3 (en) * | 1983-12-29 | 1985-08-07 | Adeka Argus Chemical Co., Ltd. | Alkylidene bisphenol phosphites and phosphates having 2,2,6,6-tetramethyl piperidinyl groups and synthetic resin compositions |
| EP0589842A1 (en) * | 1992-09-25 | 1994-03-30 | Ciba-Geigy Ag | Tetra-N-alkyl-2,2,6,6-tetramethylpiperidin-4-yl-4,4'-diphenyl-bisphosphonites as stabilisers for organic materials |
| US5442067A (en) * | 1992-09-25 | 1995-08-15 | Ciba-Geigy Corporation | Tetra-[N-alkyl-2,2,6,6,-tetramethylpiperidin-4-yl]-4,4'-diphenylbisphosphonite |
| EP0601973A1 (en) * | 1992-12-04 | 1994-06-15 | Ciba-Geigy Ag | Oligomeric HALS-phosphite and HALS-phosphonites as stabilizers |
| US5405891A (en) * | 1992-12-04 | 1995-04-11 | Ciba-Geigy Corporation | Oligomeric HALS phosphites and HALS phosphonites as stabilisers |
| FR2718742A1 (en) * | 1994-04-13 | 1995-10-20 | Ciba Geigy Ag | Phosphites and phosphoramides of hindered amine light stabilizing compounds useful as stabilizers. |
| NL1000133C2 (en) * | 1994-04-13 | 1996-05-13 | Ciba Geigy | HALS phosphites and HALS phosphoramides as stabilizers. |
| BE1008991A3 (en) * | 1994-04-13 | 1996-10-01 | Ciba Geigy Ag | PHOSPHITES phosphoramides COMPOUNDS STABILIZERS AND IN THE LIGHT OF TYPE USE AS STABILIZERS hindered amine. |
| FR2720745A1 (en) * | 1994-06-06 | 1995-12-08 | Ciba Geigy Ag | Stabilizing compounds, composition containing them and their use for stabilizing organic materials |
Also Published As
| Publication number | Publication date |
|---|---|
| BE849508A (en) | 1977-06-17 |
| JPS5289677A (en) | 1977-07-27 |
| FR2335519B1 (en) | 1979-03-09 |
| NL7614071A (en) | 1977-06-21 |
| DE2656766A1 (en) | 1977-07-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |