US4946880A
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Silylated U.V. stabilizers containing hindered tertiary amines
Assignee: Enichem Sintesi SpA
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Filing: 1987-10-05
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Granted: 1990-08-07
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Expires: 2007-10-05
Abstract
Abstract Reactive stabilizer compounds, to be used in the stabilization of organic polymers, contain a sterically hindered, N-substituted piperidinic, morpholinic or pyrrolidinic group, and at least a hydrolysable silicic function. Such compounds give rise, by hydrolysis of the silicic function, to complex resinous structures endowed with stabilizing properties. The reactive stabilizer compounds can spontaneously hydrolyse inside the polymer, or they can be stably supported on a solid support, or they can be chemically linked to the polymeric chain to be stabilized.
Inventors
- 👤 Silvestro Costanzi
- 👤 Damiano Gussoni
- 👤 Omero Zavattini, deceased
- 👤 heir by Clara Pungiluppi
- 👤 heir by Renato Zavattini
- 👤 Luciano Pallini
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 06:11
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/04; C07D207/08; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0896; C07F7/18; C07F7/1804; C08; C08K; C08K5/00; C08K5/54; C08K5/544; C08K5/5477; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31645; Y10T428/31652; Y10T428/31667; Y10T428/31855; Y10T428/31938
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
217 words
Reactive stabilizer compounds containing a 2,2,6,6-tetramethylpiperidine group, a 2,2,6,6-tetramethylmorpholine group, or a 2,2,5,5-tetramethylpyrrolidine group, said groups bearing at least one silicic function hydrolyzable into silanol, linked by a silicon-carbon link, said stabilizer compounds having the following formulas: ##STR31## wherein: m is 0 or 1; R i is H or CH 3 ; Z is a group selected from ##STR32## wherein R ii is a straight or branched alkyl radical containing from 1 to 5 carbon atoms; wherein P 1 , P 2 or both P 1 and P 2 are radicals having the formula: ##STR33## wherein R is a straight or branched alkylenic radical containing from 1 to 10 carbon atoms, or ##STR34## wherein R iii and R iv are straight or branched alkylene radicals containing from 2 to 10 carbon atoms; X is a straight or branched alkyl radical of from 1 to 5 carbon atoms; Y is H, halogen, acyl-(C 1-4 )-oxy, alkyl-(C 1-4 )-oxy, amino, amino-oxy or silyl-oxy; n is 1, 2, or 3; and in the situation where either P 1 or P 2 is a radical of formula (VIII), the other of P 1 or P 2 is (a) a straight or branched alkyl radical of from 1 to 10 carbon atoms; or (b) a phenyl or cycloaliphatic, alkyl-phenyl or alkyl-cycloaliphatic radical.
Claim 2
Dependent Claim
217 words
Reactive stabilizer compounds containing a 2,2,6,6-tetramethylpiperidine group, a 2,2,6,6-tetramethylmorpholine group, or a 2,2,5,5-tetramethylpyrrolidine group, said groups bearing at least one silicic function hydrolyzable into silanol, linked by a silicon-carbon link, said stabilizer compounds having the following formulas: ##STR31## wherein: m is 0 or 1; R i is H or CH 3 ; Z is a group selected from ##STR32## wherein R ii is a straight or branched alkyl radical containing from 1 to 5 carbon atoms; wherein P 1 , P 2 or both P 1 and P 2 are radicals having the formula: ##STR33## wherein R is a straight or branched alkylenic radical containing from 1 to 10 carbon atoms, or ##STR34## wherein R iii and R iv are straight or branched alkylene radicals containing from 2 to 10 carbon atoms; X is a straight or branched alkyl radical of from 1 to 5 carbon atoms; Y is H, halogen, acyl-(C 1-4 )-oxy, alkyl-(C 1-4 )-oxy, amino, amino-oxy or silyl-oxy; n is 1, 2, or 3; and in the situation where either P 1 or P 2 is a radical of formula (VIII), the other of P 1 or P 2 is (a) a straight or branched alkyl radical of from 1 to 10 carbon atoms; or (b) a phenyl or cycloaliphatic, alkyl-phenyl or alkyl-cycloaliphatic radical.
Claim 3
Dependent Claim
21 words
The compounds according to claim 1, wherein X is a methyl radical and Y is chlorine or an alky-(C 1-2 )-oxy.
Claim 4
Dependent Claim
17 words
The compounds according to claim 1, wherein the compounds are selected from the group consisting of: ##STR35##
Claim 5
Dependent Claim
35 words
A process for preparing the reactive stabilizer compounds of claim 1 comprising: reacting a 2,2,6,6-tetramethyl-piperidine, a 2,2,6,6-tetramethyl-morpholine or a 2,2,3,5,5-pentamethylpyrrolidine, having on the ring a group having an alkylenic unsaturated bond, with a silylating agent.
Claim 6
Dependent Claim
66 words
A process for the preparation of the reactive stabilizer compounds of claim 1 comprising: reacting a 2,2,6,6-tetramethyl-piperidine, a 2,2,6,6-tetramethyl-morpholine or a 2,2,3,5,5-pentamethylpyrrolidine, having on the nitrogen atom of the ring or on one of the carbon atoms of the ring, or on both the nitrogen atom and one of the carbon atoms on the ring, a group having an alkylenic unsaturated bone, with a silylating agent.
Claim 7
Dependent Claim
24 words
The process according to claim 4, wherein said silylating agent is ##STR36## wherein R iv , X, Y and n are as previously defined.
Claim 8
Dependent Claim
17 words
The process according to claim 6, wherein said silylating agent is methyl-diethoxy-silane, triethoxy-silane, dimethyl-chloro-silane, tetramethyl-disiloxane, or γ-mercaptopropyl-methoxy-silane.
Claim 9
Dependent Claim
51 words
The process according to claim 4, wherein the process is carried out at a temperature of from about 0° to about 200° C., in the presence of a catalyst selected from a metal catalyst, UV light and free-radical initiators, and for a time of from about 0.5 to about 10 hours.
Claim 10
Dependent Claim
73 words
The process according to claim 8, wherein the process is carried out at a temperature of from about room temperature up to about 120° C., with said catalyst consisting of a platinum compound, or of a platinum complex with olefins, in an amount of from 1 to 200 parts per million parts in the reaction medium, in the presence of an inert organic solvent selected from aliphatic, cycloaliphatic or aromatic hydrocarbons, and ethers.
Claim 11
Dependent Claim
28 words
Stabilized polymeric composition comprising: an organic polymer and an effective amount of a stabilizer product resulting from hydrolysis and resinification of the reactive stabilizer compound of claim 1.
Claim 12
Dependent Claim
29 words
The composition according to claim 10, wherein said hydrolysis and resinification are carried out in the presence of a catalyst selected from zinc octanoate, lead naphthenate and tin dibutyl-laurate.
Claim 13
Dependent Claim
21 words
The composition according to claim 10, wherein said hydrolysis and resinification are carried out in the presence of a silicon paint.
Claim 14
Dependent Claim
22 words
The composition according to claim 10, wherein the hydrolysis and resinification of the reactive stabilizer compound occur spontaneously inside the organic polymer.
Claim 15
Dependent Claim
30 words
A stabilized polymeric composition comprising: an organic polymer and an effective amount of the reactive stabilizer compound according to claim 1, fixed onto a solid support containing surface hydroxy groups.
Claim 16
Dependent Claim
22 words
The composition according to claim 14, wherein said solid support is selected from diatomaceous earth, celite, silica gel, cement, glass and silico-aluminates.
Claim 17
Dependent Claim
12 words
The composition according to claim 15, wherein said silica is fumed silica.
Claim 18
Dependent Claim
26 words
A stabilized polymeric composition comprising: an organic polymer and an effective amount of a reactive stabilizer compound according to claim 1, chemically bonded to the polymer.
Claim 19
Dependent Claim
25 words
The composition according to claims 10, 11, 12, 13, 14, 15, 16 or 17, wherein the organic polymer is an ethylene, propylene or butadiene homopolymer.
Claim 20
Dependent Claim
13 words
The composition according to claim 18, wherein the organic polymer is ethylene homopolymer.
Claim 21
Dependent Claim
27 words
The composition according to claim 10, wherein there is present an amount of the stabilizer compound which supplies from about 0.003 to about 0.3% of active nitrogen.
Claim 22
Dependent Claim
33 words
The composition according to claim 20, wherein there is present the amount of the stabilizer compound sufficient to provide an amount of active nitrogen of from about 0.005 to about 0.023% by weight.
References Cited (Backward Citations)
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