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GB2215727A - Stabilisers for polymers - Google Patents

Stabilisers for polymers Download PDF

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Publication number
GB2215727A
GB2215727A GB8903148A GB8903148A GB2215727A GB 2215727 A GB2215727 A GB 2215727A GB 8903148 A GB8903148 A GB 8903148A GB 8903148 A GB8903148 A GB 8903148A GB 2215727 A GB2215727 A GB 2215727A
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United Kingdom
Prior art keywords
composition according
butyl
weight
component
composition
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
Application number
GB8903148A
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GB8903148D0 (en
GB2215727B (en
Inventor
Jean-Paul Kehrli
Rainer Wolf
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Sandoz AG
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Sandoz AG
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Publication date
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Publication of GB8903148D0 publication Critical patent/GB8903148D0/en
Publication of GB2215727A publication Critical patent/GB2215727A/en
Application granted granted Critical
Publication of GB2215727B publication Critical patent/GB2215727B/en
Expired legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/49Phosphorus-containing compounds
    • C08K5/51Phosphorus bound to oxygen
    • C08K5/52Phosphorus bound to oxygen only
    • C08K5/524Esters of phosphorous acids, e.g. of H3PO3
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/49Phosphorus-containing compounds
    • C08K5/51Phosphorus bound to oxygen
    • C08K5/52Phosphorus bound to oxygen only
    • C08K5/527Cyclic esters
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/49Phosphorus-containing compounds
    • C08K5/51Phosphorus bound to oxygen
    • C08K5/53Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333Esters of phosphonic acids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/49Phosphorus-containing compounds
    • C08K5/51Phosphorus bound to oxygen
    • C08K5/53Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5393Phosphonous compounds, e.g. R—P(OR')2

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  • 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)

Description

22 15727 Case 153-5237 IMPROVEM M S IN OR RELATING TO ORGANIC COMPOUNDS
The invention relates to a mixture of a phosphonite and a phosphite stabiliser for polymeric substrates.
According to the invention, there is provided a composition for use as a processing stabiliser (herein defined as a stabilising composition), comprising a) 30-80% by weight of a compound of formula I t.butyl HC-C HC-CH (t. bu tyl-C 0 C -0-) 2 P-C 0 C-R, (I) HC-CH HC-CH in which R, is hydrogen, methyl, unsubstituted phenyl or a group of formula a,) t.butyl HC-C (0), HC-CH (t.butyl-C 0 C-O-)2- P -C 0 C- (a,) HC-CH HC-CH 2 Case 153-5237 in which n is 0 or 1 or mixtures thereof; (herein defined to as component a); and b) 20-70% by weight of an organic phosphite compound ( herein defined as component b). and Usually component a) will be a mixture of a mono di-phosphonite.
Compounds of formula I and component b) are antioxidants. i Preferably a composition according to the invention contains one or more additional antioxidants (for example sterically hindered j phenolic antioxidants, aminoaryl antioxidants or sulphur containing antioxidants).
Preferred phosphites are those of formula II or III P(-O-R)3 (II) O-CH2 CH2-0 ROP c P-O-R (III) O-CH2 CH2-0 in which each R, independently, is a linear or branched Cl-22 alkyl or phenyl,unsubstituted or substituted by 1 to 3 linear or branched Cl-12alkyl groups (preferably methyl or t.butyl).
More preferred phosphites of a stabilising composition according 5 to the invention are selected from tris-(2,4-di t.butylphenyl) phosphite, tris (nonylphenyl) phosphite, trilauryl phosphite, bis 3 - Case 153-5237 (2,6-di-t.butyl-4- methylphenyl) pentaerythrityldiphosphite, bis (2,4-dit.butyl phenyl) pentaerythrityl-diphosphite and distearylpentaerythrityl diphosphite.
Preferred phenolic antioxidants are selected from octadecyl-3-(31,51ditert.butyl-41-hydroxyphenyl)-propionate, pentaerythrityl-tetrakis-3-(31, 51-ditert.butyl-41-hydroxyphenyl) -propionate, 1,3,5-tris-(31,51-ditbutyl-41-hydroxy-phenyl) -isocyanurate, 1,1,3,tris-(51-tert.butyl-41hydroxy-21-methylphenyl) -butane, 1,3,5-tris-(31,51-ditert.butyl-41hydroxybenzyl)-mesitylene and ethylene glycol-bis-(3,3-bis-(31-tert.butyl41-hydroxyphenyl) -butyrate).
Preferred aminoaryl antioxidants are selected from N,NI-dinaphthyl-pphenylene diamine and N,N1-hexamethylene bis-3-(3,5-ditert.butyl-4hydroxyphenyl)-propionamide.
Preferred sulphur containing antioxidants are selected from di-tridecyl-3, 3- thiodipropionate, di-lauryl-3,31-thiodipropionate, distearyl3,31 thiodipropionate, methane tetrakis- (methylene -3-hexyl thiopropionate) and dioctadecyl-disulphide.
A further preferred additive to a stabilising composition according to the invention is alpha tocopherol (Vitamin E).
Preferably, in a composition according to the invention, the amount of component a) present is from 70 to 40% by weight and the amount of component b) present is from 30 to 60%, by weight of the composition. More preferably in a composition according to the invention, the amount of component a) present is 40-60% by weight and the amount of component b is 60-40% by weight of the composition.
Preferably, if an antioxidant (or Vitamin E) is present, it is present in an amount of 50 to 200%, by weight of components a) and b) of a composition according to the invention.
4 - Case 153-5237 Further, according to the invention, there is provided a polymeric composition comprising a polymeric material and a stabilising amount of a stabilising composition according to the invention.
Preferably the total amount of components a) and b) present in such a polymeric composition is from 0.01 to 1 X; more preferably 0.05 to 0.3 % by weight based on the polymeric material.
It has been found that a combination of a) and b) in a stabilising composition according to the invention produces a 1 synergistic effect on the stability of a polymeric composition to which it is applied. Properties such as yellowing (as measured using the yellowness index) and the melt flow index (MFI) of such polymeric compositions are significantly improved over those in which only component a) or b) is present.
Preferred polymeric materials to be stabilised are polyolefins such as polypropylene, polyethylene (e.g. high density polyethylene, low density polyethylene, linear low density polyethylene or medium density polyethylene), polyisobutylene, poly-4-methylpentene and copolymers thereof (such as EVA-ethylene vinyl acetate).
Further polymeric materials that can be stabilised by a stabilising composition according to the invention include polystyrene and copolymers and blends thereof, ABS, polyvinyl acetate, polyvinylalcohol, polyacetate (POM), polyacrylate and polymethacrylate, polyacrylonitrile, polyacrylamide, PVC, polyvinylidene chloride, polyamide, polyester (for example polybutylene terephthalate and polyethylene terephthalate), polyether (e.g. polyphenylene oxide - PPO), polythioether and thioplast, polycarbonate, polyurethane, cellulose derivatives, maleinate resins, melamine resins, phenolic resins, aniline resins, furane resins, carbamide resins, epoxide resins and silicon resins.
Further additives that can be added to a stabilising or a Case 153-5237 polymeric composition according to the invention include flame retardants, antistatic agents, U.V. stabilisers such as hindered light amine stabilisers and U.V. absorbers (e.g. 2-(21-hydroxyphenyl) -benztriazoles, 2-hydroxybenzophenones, 1,3-bis-(21-hydroxybenzoyl-) benzene salicylates, cinnamates and oxalic acid diamides;), U-.V.quenchers such as benzoates and substituted benzoates, sterically hindered amines (for example Nunsubstituted, N-alkyl or N-acyl substituted 2,2,6,6-tetramethylpiperidine compounds), softeners, nucleating agents, metal deactivators, biocides, impact modifiers, fillers, pigments and fungicides.
Stabilising compositions according to the invention may be added to the polymeric material before, during or after the polymerization step and may be added in solid or molten form, in solution preferably as a liquid concentrate containing from 10 to 80 % by weight of the composition and 90 to 20 % by weight of solvent or as a solid masterbatch composition containing 10 to 80 % (more preferably 40 to 70 X) by weight of the composition and 90 to 20 % (more preferably 60 to 30 X) by weight of a solid polymeric material which is identical with or compatible with the material to be stabilized.
The compositions according to the invention may be incorporated by known methods into the polymeric material to be stabilized. Of particular importance is blending of the compounds with thermoplastic polymers in the melt, for example in a melt blender or during the formation of shaped articles, including foils, tubes, fibres and foams by extrusion, injection moulding, blow moulding, spinning or wire coating. The compositions according to the invention are particularly useful for polypropylene fibres or foils.
Further, in this specification, where a range is given, the figures defining the range are included therein. Any group capable of being linear or branched is linear or branched unless indicated to the contrary.
For the avoidance of doubt, in this specification t-butyl means
6 Case 153-5237 tertiary butyl.
The invention will now be illustrated by the following Examples in which all parts and percentages are by weight and all temperatures are in C unless indicated to the contrary.
i - I i I i 1 EXAMPLE 1
A solution is made up as follows:
1 g. of calcium stearate, 1 g. of pentaerythrityl-tetrakis-3-(31,51-di-t.butyl-41-hydroxy -phenyl)propionate, 0.4 g. of tetrakis-(2,4di-t.butyl-phenyl)-4,41biphenylene -diphosphonite, and 0.4 g. of tris (2,4-di-t.butyl-phenyl)-phosphite, and 0.2 g. of bis(2,4 di-t.butylphenyl) diphenyl phosphonite (=0,01-bis(2,4ditertiarybutyl)biphenylphosphonite) dissolved in 25 mls of acetone.
This solution is added to 1000 g of polypropylene powder and is mixed for 5 minutes at 400 revs per minute. The powder is dried for 30 minutes at 50'C in an oven and subsequently compounded in a G8ttfert extrusiometer having a 20 mm screw (compression 1:3, diameter to length [d:l] = 1:20) at 2701C. Multiple extrusions are carried out under the same conditions. The Melt Flow Index (MFI) is determined at 2301C/2.16kp and is used to characterise the stabilisation efficiency.
EXAMPLES 2 to 4 Example 1 is repeated using, instead of 0.4 g. of the tris (2,4-di-t. butyl- phenyl) phosphite, 0.2 g of the tris (2,4-di-t.butylphenyl) phosphite and 0.2 g. of one of the f ollowing:
Example 2: tris-(nonylphenyl)phosphite; Example 3: a 40:60 mixture of alpha tocopherol (Vitamin E) and tris- (nonylphenyl)-phosphite; and Example 4: a 20:40:40 mixture of alpha tocopherol (Vitamin E), ditridecyl3,31-thiodipropionate and tri-lauryl-phosphite.

Claims (16)

CLAIMS:
1. A composition for use as a processing stabiliser (herein defined as a stabilising composition), comprising a) 30-80X. by weight of a compound of formula I t.butyl HC-C HC-CH 1 \ (t.butyl-C 0 C-O-)2 P-C 0 C-R, (I) HC-CH HC-CH in which R, is hydrogen, methyl, unsubstituted phenyl or a group of formula a,) t.butyl HC-C (0),, HC-CH (t. butyl-C 0 CO-) 2 P -C 0 C- (a,) HC-CH HC-CH in which n is 0 or 1; (herein defined to as component a); and b) 20-70% by weight of a phosphite compound ( herein defined as component b).
2. A composition according to Claim 1 in which component b is selected from one or more compounds of formula II or III P(-O-R)3 O-CH2 CH2-0 R-0-P c P-O-R (III) O-CH2 CH2-0 in which each R, independently, is a linear or branched Cl-22 alkyl or phenyl,unsubstituted or substituted by 1 to 3 linear or branched Cl- 12alkyl groups.
3. A composition according to Claim 2 in which component b) is selected from tris-(2,4-di t.butylphenyl) phosphite, tris (nonylphenyl) phosphite, trilauryl phosphite, bis (2,6-di-t.butyl-4methylphenyl) pentaerythrityldiphosphite, bis (2,4-dit.butyl phenyl) pentaerythrityl-diphosphite and distearyl- pentaerythrityl diphosphite.
4. A composition according to any one of the preceding claims which contains one or more additional antioxidants.
5. A composition according to Claim 4 in which the additional antioxidants are selected from sterically hindered phenolic antioxidants, aminoaryl antioxidants or sulphur containing antioxidants.
6. A composition according to Claim 5 in which the phenolic antioxidants are selected from octadecyl-3-(31,51-ditert.- - 10 Case153-5237 butyl-41-hydroxyphenyl)propionate, pentaerythrityl-tetrakis-3(3f,51ditert.butyl41-hydroxyphenyl) -propionate, 1,3,5-tris(31,51-di-t-butyl-41hydroxy-phenyl) -isocyanurate, 1,1,3,tris(51-tert.butyl-41-hydroxy-21methylphenyl) -butane, 1,3,5-tris-(31,51-ditert.butyl41-hydroxybenzyl)mesitylene and ethylene glycol-bis-(3,3-bis-(31-tert.butyl-41hydroxyphenyl) -butyrate).
7. A composition according to Claim 5 in which the aminoaryl antioxidants are selected from N,NI-dinaphthyl-p- phenylene diamine and N,N1hexamethylene bis-3-(3,5-ditert.butyl-4- hydroxyphenyl)-propionamide.
8. A composition according to Claim 5 in which the sulphur containing antioxidants are selected from di-tridecyl-3,3- i:
thiodipropionate, di-lauryl-3,31-thiodipropionate, distearyl-3,31 thiodipropionate, methane tetrakis- (methylene -3-hexyl thiopropionate) and dioctadecyl-disulphide
9. A composition according to any one of the preceeding claims containing as a further additive alpha tocopherol (Vitamin E).
10. A composition according to any one of the preceeding claims in which the amount of component a) present is from 70 to 40% by weight and the amount of component b) present is from 30 to 60%, by weight of the composition.
11. A composition according to Claim 10 in which the amount of component a) present is 40-60% by weight and the amount of component b is 60-40% by weight of the composition.
12. A composition according to Claim 4 or any one of Claims 5 to 11 when appendant to Claim 4 in which the additional antioxidant (or Vitamin E) is present in an amount of 50 to 200%, by weight of components a) and b) of the composition.
Case 153-5237
13. A polymeric composition comprising a polymeric material and a stabilising amount of a stabilising composition according to any one of the preceeding claims.
14. A polymeric composition according to Claim 13 in which the amounts of components a) and b) present are from 0.01 to 1 % by weight based on the polymeric material.
15. A stabilising composition according to Claim 1 substantially as herein described with reference to the any one of Examples 1 to 4.
16. A polymeric composition according to Claim 4 substantially as herein described with reference to the any one of Examples 1 to 4.
1 C Publiabbd IW9atThe Patent Offtce,State House, 66171 High HoIbornLondoIXWC1R4TP. Purther copies maybe obtainedfrom TheP&tentO:Moe.
Sales Branch, St Mary Cray, Orpington, Kent BRB 3P.D. Printed by Multiplex techniques ltd, St Mary Cray, Kent, Con. 1187 --,a- zrancD, ut mary uway, urpmgron, jLent bliz 41W. k=tea DY MUMPlax techniques Itd, St Merv Cray, Kent, Con. 1187
GB8903148A 1988-02-15 1989-02-13 Stabilizers for polymers Expired GB2215727B (en)

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GB888803439A GB8803439D0 (en) 1988-02-15 1988-02-15 Improvements in/relating to organic compounds

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GB2215727A true GB2215727A (en) 1989-09-27
GB2215727B GB2215727B (en) 1992-06-03

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GB8903148A Expired GB2215727B (en) 1988-02-15 1989-02-13 Stabilizers for polymers

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JP (1) JPH01254744A (en)
CH (1) CH678331A5 (en)
DE (1) DE3903218A1 (en)
FR (1) FR2627185B1 (en)
GB (2) GB8803439D0 (en)
HK (1) HK70395A (en)
IT (1) IT1230465B (en)
SG (1) SG25295G (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2227490A (en) * 1989-01-24 1990-08-01 Sandoz Ltd Polymer stabilisers
GB2247241A (en) * 1990-08-22 1992-02-26 Sandoz Ltd Stabilising composition for filled polymeric materials
GB2261667A (en) * 1991-11-20 1993-05-26 Sandoz Ltd Stabilized polymeric compositions
US5300257A (en) * 1991-05-27 1994-04-05 Yoshitomi Pharmaceutical Industries, Ltd. 4,4'-biphenylenediphosphonite compound and use thereof
US5308549A (en) * 1991-11-12 1994-05-03 Hoffmann-La Roche Inc. Stabilizers for thermo plastic materials
GB2263280B (en) * 1992-01-17 1996-07-31 Sandoz Ltd Use of a phosphonite and optionally a phosphite for clarifying propylene polymers
US5703150A (en) * 1994-12-28 1997-12-30 Yoshitomi Pharmaceutical Industries, Ltd. Phosphonite or phosphonate compounds and use thereof
EP0842985A1 (en) * 1996-11-15 1998-05-20 Basf Aktiengesellschaft Thermooxidation resistant thermoplastic moulding masses
EP1024165A1 (en) * 1997-10-02 2000-08-02 Yoshitomi Fine Chemicals, Ltd. Stabilizer composition for organic polymeric materials containing 6-hydroxychroman compounds and organic polymeric material compositions
US6465548B1 (en) 1997-10-02 2002-10-15 Yoshitomi Fine Chemicals, Ltd. Stabilizer for organic polymer material and organic polymer material composition
WO2014074596A1 (en) 2012-11-08 2014-05-15 Equistar Chemicals, Lp Stabilized high-density polyethylene composition with improved resistance to deterioration and stabilzer system

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2525319B2 (en) * 1992-04-08 1996-08-21 チッソ株式会社 Crystalline polyolefin composition
US5468895A (en) * 1994-10-19 1995-11-21 General Electric Company Amine stabilized amorphous phosphite
AU2977597A (en) * 1996-05-31 1998-01-05 Kanebo Limited Polyester resin composition and film made therefrom, polyester composite film and metal laminate made by using the same, and process for decreasing the content of low-molecular compounds present in polyester
GB9613515D0 (en) * 1996-06-27 1996-08-28 Clariant Int Ltd Stabilizer compositions
JP2000290503A (en) * 1999-04-08 2000-10-17 Tosoh Corp Polyphenylene sulfied resin composition
JP2008222817A (en) * 2007-03-12 2008-09-25 Furukawa Electric Co Ltd:The Resin composition and molded article using it

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4427814A (en) * 1980-03-10 1984-01-24 Mitsubishi Gas Chemical Company, Inc. Polyphenylene ether resin composition having improved heat stability
EP0151327A1 (en) * 1984-01-06 1985-08-14 SOLVAY & Cie (Société Anonyme) Stabilized compositions based on alpha-olefin polymers

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2962673D1 (en) * 1978-04-20 1982-06-24 Ciba Geigy Ag Ortho-alkylated phenylphosphonites, process for their preparation and stabilized compositions
DE3170981D1 (en) * 1980-03-10 1985-07-25 Mitsubishi Gas Chemical Co Polyphenylene ether resin composition of improved heat stability and shaped articles thereof
JPS57158254A (en) * 1981-03-24 1982-09-30 Teijin Chem Ltd Stabilized polycarbonate resin composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4427814A (en) * 1980-03-10 1984-01-24 Mitsubishi Gas Chemical Company, Inc. Polyphenylene ether resin composition having improved heat stability
EP0151327A1 (en) * 1984-01-06 1985-08-14 SOLVAY & Cie (Société Anonyme) Stabilized compositions based on alpha-olefin polymers
US4670493A (en) * 1984-01-06 1987-06-02 Solvay & Cie (Societe Anonyme) Stabilized compositions based on alpha-olefin polymers

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2227490A (en) * 1989-01-24 1990-08-01 Sandoz Ltd Polymer stabilisers
GB2227490B (en) * 1989-01-24 1993-01-06 Sandoz Ltd New phosphonite compounds
GB2247241A (en) * 1990-08-22 1992-02-26 Sandoz Ltd Stabilising composition for filled polymeric materials
US5300257A (en) * 1991-05-27 1994-04-05 Yoshitomi Pharmaceutical Industries, Ltd. 4,4'-biphenylenediphosphonite compound and use thereof
US5308549A (en) * 1991-11-12 1994-05-03 Hoffmann-La Roche Inc. Stabilizers for thermo plastic materials
GB2261667A (en) * 1991-11-20 1993-05-26 Sandoz Ltd Stabilized polymeric compositions
GB2263280B (en) * 1992-01-17 1996-07-31 Sandoz Ltd Use of a phosphonite and optionally a phosphite for clarifying propylene polymers
US5703150A (en) * 1994-12-28 1997-12-30 Yoshitomi Pharmaceutical Industries, Ltd. Phosphonite or phosphonate compounds and use thereof
EP0842985A1 (en) * 1996-11-15 1998-05-20 Basf Aktiengesellschaft Thermooxidation resistant thermoplastic moulding masses
US6479572B1 (en) 1996-11-15 2002-11-12 Basf Aktiengesellschaft Thermoplastic molding materials stable to thermal oxidation
EP1024165A1 (en) * 1997-10-02 2000-08-02 Yoshitomi Fine Chemicals, Ltd. Stabilizer composition for organic polymeric materials containing 6-hydroxychroman compounds and organic polymeric material compositions
EP1024165A4 (en) * 1997-10-02 2001-01-24 Yoshitomi Fine Chemicals Ltd Stabilizer composition for organic polymeric materials containing 6-hydroxychroman compounds and organic polymeric material compositions
US6465548B1 (en) 1997-10-02 2002-10-15 Yoshitomi Fine Chemicals, Ltd. Stabilizer for organic polymer material and organic polymer material composition
WO2014074596A1 (en) 2012-11-08 2014-05-15 Equistar Chemicals, Lp Stabilized high-density polyethylene composition with improved resistance to deterioration and stabilzer system

Also Published As

Publication number Publication date
GB8903148D0 (en) 1989-03-30
IT1230465B (en) 1991-10-23
DE3903218A1 (en) 1989-08-24
HK70395A (en) 1995-05-19
FR2627185A1 (en) 1989-08-18
GB2215727B (en) 1992-06-03
JPH01254744A (en) 1989-10-11
SG25295G (en) 1995-06-16
GB8803439D0 (en) 1988-03-16
CH678331A5 (en) 1991-08-30
FR2627185B1 (en) 1993-05-14
IT8947641A0 (en) 1989-02-14

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PCNP Patent ceased through non-payment of renewal fee

Effective date: 19970213