Polysilylesters having a polyalkylpiperidine as part of the polymer useful as light stabilizers for plastics

• US 4,250,268 A
• Filed: 11/28/1978
• Issued: 02/10/1981
• Est. Priority Date: 11/28/1978
• Status: Expired due to Term

• Current Assignee: CIBA Specialty Chemicals
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Rody, Jean, Rasberger, Michael
• Primary Examiner(s): Welsh, Maurice J.
• Application Number:
  US05/964,443
• Time in Patent Office: 805 Days
• Field of Search: 528/27, 525/100, 525/106, 525/431, 525/452
• US Class Current: 525/100
• CPC Class Codes: C07D 211/14 with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
• CPC Class Codes: C07D 211/22 by oxygen atoms
• CPC Class Codes: C07D 211/34 with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: C07D 211/44 attached in position 4
• CPC Class Codes: C07D 211/58 attached in position 4
• CPC Class Codes: C07D 211/66 having a hetero atom as the second substituent in position 4
• CPC Class Codes: C07D 211/94 Oxygen atom, e.g. piperidine N-oxide
• CPC Class Codes: C07D 471/10 Spiro-condensed systems
• CPC Class Codes: C08G 77/62 Nitrogen atoms
• CPC Class Codes: C08K 5/5477 containing nitrogen in a heterocyclic ring
• CPC Class Codes: C08L 101/00 Compositions of unspecified macromolecular compounds
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C08L 83/16 in which all the silicon atoms are connected by linkages other than oxygen atoms

Abstract

Condensation polymers or addition polymers which contain sterically hindered polyalkylpiperidine groups are proposed as light stabilizers for plastics. The polymers concerned are relatively low-molecular polymers and a difunctional derivative of a polyalkylpiperidine is additionally used for the manufacture of these. The piperidine radical can be present in the main chain or as a side group of the polymeric stabilizer. Polymeric stabilizers of this type do not tend to migrate out of the plastic or to be removed by extraction; they are therefore very permanent in use.

Claims

1. A polysilylester of the formula ##STR60## wherein n denotes a value of from 2 to about 50, E represents a divalent organic radical which contains a polyalkylpiperidine radical of the formula ##STR61## or is substituted by a polyalkylpiperidine side group of the formula ##STR62## in which R denotes hydrogen or alkyl with 1-5 C atoms and R'"'"' denotes hydrogen, alkyl with 1-12 C atoms, alkenyl with 3-8 C atoms, alkinyl with 3-6 C atoms, aralkyl with 7-12 C atoms, alkanoyl with 1-8 C atoms or alkenoyl with 3-5 C atoms and R¹ and R² represent methyl, ethyl or phenyl, or a copolymer thereof with a polyalkylpiperidine-free component.

2. A polysilylester according to claim 1, the recurrent molecular unit of which contains a polyalkylpiperidine radical of the formula ##STR63## or is substituted by a polyalkylpiperidine side group of the formula ##STR64## in which R denotes hydrogen or an alkyl radical with 1-5 C atoms and R'"'"' denotes hydrogen, alkyl with 1-12 C atoms, allyl, benzyl, acetyl, acryloyl or crotonyl.

3. A polysilylester according to claim 1 of the general formula III, in which R¹ and R² independently of one another denote methyl, ethyl or phenyl and E represents one of the radicals of the formula XVIII to XXX:

##STR65## in which R denotes hydrogen or alkyl with 1-5 C atoms, R'"'"' denotes hydrogen, alkyl with 1-12 C atoms, allyl, benzyl, acetyl, acryloyl or crotonyl, X" is oxygen or NH, Z denotes a direct bond, --CH₂ CH₂ --or --OCH₂ CH₂ CH₂ --, Z² denotes one of the radicals --N(R")--, --NR³ --CO--NR³ --, --NR³ --CO--CO--NR³ --, --NR³ --CO--Z³ --CO--NR³ --, alkylene with 4-10 C atoms, p-xylylene, ##STR66## --O--alkylene--O-- with 1-10 C atoms, --O--alkylene--O-- with 4-8 C atoms or --O--xylylene--O--, in which R³ denotes hydrogen, alkyl with 1-12 C atoms, cyclohexyl, benzyl, or aryl with 6-14 C atoms, R" denotes alkanoyl with 1-8 C atoms or alkenoyl with 3-5 C atoms and Z³ denotes alkylene with 1-10 C atoms or phenylene, and B'"'"' represents an alkylene radical with 2-12 C atoms, a xylylene or hexahydroxylylene radical, a cyclohexylene or 4,4'"'"'-dicyclohexylmethane radical, an arylene radical with 6-12 C atoms or a -phenylene-Z⁴ -phenylene- radical, in which Z⁴ denotes --CH₂ --, C(CH₃)₂, --O-- or --SO₂ --, R⁵ is hydrogen, methyl or phenyl, Z⁵ represents alkylene or alkenylene with 4-8 C atoms, p-xylylene or a group of the formula ##STR67## Z⁶ represents one of the groups --CH₂ CH₂ --, --OCH₂ CH(R⁵)--N(R³)--CH₂ --CH(R⁵)--, --CH₂ CH₂ --N(R³)--CH₂ CH(R⁵)-- or --O--(CH₂)₃ --N(R³)--CH₂ CH(R⁵)--, Z⁷ is alkylene with 2-12 C atoms, arylene with 6-12 C atoms, 4,4'"'"'-dicyclohexylenemethane or a radical -phenylene-Z⁴ -phenylene-, Z^7'"'"' denotes alkylene or alkenylene with 4-8 C atoms or p-xylylene and B" denotes an alkylene radical with 2-12 C atoms, an alkenylene radical with 4-8 C atoms, a xylylene or hexahydroxylylene radical, a cyclohexylene radical or a radical of the formula --CH₂ CH₂ OCH₂ CH₂ -- or --CH₂ CH₂ O--phenylene--OCH₂ CH₂ --.

4. A copolymer according to claim 1, which consists of one of the structural units listed in claim 53 and a polyalkylpiperidine-free structural unit.

5. A copolymer according to claim 4, in which the proportion of the polyalkylpiperidine-free component is at most 50 mol %.

6. A polysilylester according to claim 1 in which R is hydrogen or methyl.

7. A polysilylester according to claim 1 in which R is hydrogen.

8. A polysilylester according to claim 3 in which R'"'"' denotes hydrogen or methyl.

9. A polysilylester according to claim 8 in which R'"'"' is hydrogen.

10. A plastic stabilised against photodegradation which contains 0.005 to 5% by weight of at least one polysilylester of claim 1.

11. A stabilised plastic according to claim 10 which contains 0.01 to 1 by weight of the polymeric stabiliser.

12. A stabilised plastic according to claim 10 or 11 which additionally contains yet a further stabiliser or other additives customary in plastics technology.

13. A stabilized plastic according to claim 11 which contains 0.02 to 0.5% by weight of the polymeric stabilizer.

14. A stabilised plastic according to claims 10 or 14 said plastic being selected from the group consisting of polyolefine, styrene polymer, polyurethane or polyamide.