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Patent US4086207A successfully refreshed from Google Patents.
US4086207A
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Polyurea compounds which improve the light stability of polymers
Assignee: Novartis Corp
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Filing: 1976-06-23
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Granted: 1978-04-25
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Expires: 1996-06-23
Abstract
Abstract Novel polyurea compounds having the general formula ##STR1## where R 1 is hydrogen, alkyl, cycloalkyl, aryl, substituted aryl, aralkyl, or a piperidine radical of the formula ##STR2## where R 5 , R 6 , R 8 and R 9 are alkyl and R 7 is hydrogen, oxygen, alkyl, alkenyl, alkinyl or aralkyl, R 2 is alkylene, cycloalkylene, arylene or aralkylene, R 3 is a piperidine radical as set forth above, R 4 is alkylene, cycloalkylene, arylene or aralkylene, X is zero or one, y is an integer from 2 to 200 and A and B each represent a terminal group. In some of the y units and in B the ##STR3## can be replaced in part by ##STR4## where R 10 R 11 and R 12 are hydrogen, alkyl, cycloalkyl, aryl, aralkyl or R 10 and R 11 , are linked together so that ##STR5## forms a 6 to 8 member heterocyclic ring Are produced by reacting a diamine with carbonyl chloride or a diisocyanate. The compounds are valuable light stabilizers for synthetic polymers, particularly polypropylene and polyethelene.
Inventors
- 👤 Paolo Cassandrini
- 👤 Antonio Tozzi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 02:24
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3412; C08K5/3432; C08K5/3435; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/58; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/32; C08G18/3225; C08G18/3246; C08G71/00; C08G71/02; C08K5/21; C08L; C08L101/00
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
391 words
A compound which either (1) has the formula ##STR17## wherein: R 1 is a member selected from hydrogen, straight and branched alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 18 carbon atoms, aryl and substituted aryl having 6 to 18 carbon atoms, aralkyl having 7 to 18 carbon atoms, a piperidine radial having the formula: ##STR18## in which R 5 , R 6 , R 8 and R 9 are members individually selected from alkyl having 1 to 6 carbon atoms and R 7 is selected from hydrogen, oxygen, straight and branched chain alkyl having 1 to 18 carbon atoms, alkenyl and alkinyl having 2 to 18 carbon atoms, aralkyl having 7 to 18 carbon atoms; R 2 is a member selected from straight and branched chain alkylene having 2 to 18 carbon atoms, cycloalkylene having 5 to 18 carbon atoms, arylene having 6 to 18 carbon atoms, aralkylene having 7 to 18 carbon atoms; R 3 is a piperidine radical of formula (II); R 4 is a member selected from straight and branched chain alkylene having 2 to 18 carbon atoms, cycloalkylene having 5 to 18 carbon atoms, arylene having 6 to 18 carbon atoms, aralkylene having 7 to 18 carbon atoms; x is either 0 or 1; y is an integer from 2 to 200; A and B each represents a terminal group wherein A is H and B is ##STR19## or (2) has the formula (I) in which a proportion of the y units and the terminal group B has the radical ##STR20## replaced by ##STR21## wherein R 10 , R 11 and R 12 are hydrogen, alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 18 carbon atoms, aryl having 6 to 18 carbon atoms, aralkyl having 7 to 18 carbon atoms, or R 10 and R 11 are linked together so that the group ##STR22## forms a heterocyclic ring having 6 to 8 inclusive members and which contains 2 nitrogen atoms; the proportion of y units with a replaced radical resulting from using in the reaction not over 2 moles of an amine or hydroxyl reactant containing the replacing radicals ##STR23## per mole of the amine reactant containing the radical ##STR24## so that per one y unit containing a radical ##STR25## 0to 2 y units having said radical replaced are present.
Claim 2
Dependent Claim
391 words
A compound which either (1) has the formula ##STR17## wherein: R 1 is a member selected from hydrogen, straight and branched alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 18 carbon atoms, aryl and substituted aryl having 6 to 18 carbon atoms, aralkyl having 7 to 18 carbon atoms, a piperidine radial having the formula: ##STR18## in which R 5 , R 6 , R 8 and R 9 are members individually selected from alkyl having 1 to 6 carbon atoms and R 7 is selected from hydrogen, oxygen, straight and branched chain alkyl having 1 to 18 carbon atoms, alkenyl and alkinyl having 2 to 18 carbon atoms, aralkyl having 7 to 18 carbon atoms; R 2 is a member selected from straight and branched chain alkylene having 2 to 18 carbon atoms, cycloalkylene having 5 to 18 carbon atoms, arylene having 6 to 18 carbon atoms, aralkylene having 7 to 18 carbon atoms; R 3 is a piperidine radical of formula (II); R 4 is a member selected from straight and branched chain alkylene having 2 to 18 carbon atoms, cycloalkylene having 5 to 18 carbon atoms, arylene having 6 to 18 carbon atoms, aralkylene having 7 to 18 carbon atoms; x is either 0 or 1; y is an integer from 2 to 200; A and B each represents a terminal group wherein A is H and B is ##STR19## or (2) has the formula (I) in which a proportion of the y units and the terminal group B has the radical ##STR20## replaced by ##STR21## wherein R 10 , R 11 and R 12 are hydrogen, alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 18 carbon atoms, aryl having 6 to 18 carbon atoms, aralkyl having 7 to 18 carbon atoms, or R 10 and R 11 are linked together so that the group ##STR22## forms a heterocyclic ring having 6 to 8 inclusive members and which contains 2 nitrogen atoms; the proportion of y units with a replaced radical resulting from using in the reaction not over 2 moles of an amine or hydroxyl reactant containing the replacing radicals ##STR23## per mole of the amine reactant containing the radical ##STR24## so that per one y unit containing a radical ##STR25## 0to 2 y units having said radical replaced are present.
Claim 3
Dependent Claim
237 words
A compound according to claim 1 having the formula ##STR26## wherein: R 1 is a member selected from hydrogen, straight and branched alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 18 carbons atoms, aryl and substituted aryl having 6 to 18 carbon atoms, aralkyl having 7 to 18 carbon atoms, a piperidine radical having the formula ##STR27## in which R 5 , R 6 , R 8 and R 9 are members individually selected from alkyl having 1 to 6 carbon atoms and R 7 is selected from hydrogen, oxygen, straight and branched chain alkyl having 1 to 18 carbon atoms, alkenyl and alkinyl having 2 to 18 carbon atoms, aralkyl having 7 to 18 carbon atoms; R 2 is a member selected from straight and branched chain alkylene having 2 to 18 carbon atoms, cycloalkylene having 5 to 18 carbon atoms, arylene having 6 to 18 carbon atoms, aralkylene having 7 to 18 carbon atoms; R 3 is a piperidine radical of formula (II): R 4 is a member selected from straight and branched chain akylene having 2 to 18 carbon atoms, cycloalkylene having 5 to 18 carbon atoms, arylene having 6 to 18 carbon atoms, aralkylene having 7 to 18 carbon atoms; x is either 0 or 1; y is an integer from 2 to 200; A and B each represent a terminal group with A being H and B being ##STR28##
Claim 4
Dependent Claim
26 words
The compound according to claim 2, in which R 5 , R 6 , R 8 and R 9 are the same and are methyl groups.
Claim 5
Dependent Claim
25 words
The compound according to claim 2, in which R 7 is a member selected from hydrogen and alkyl having 1 to 6 inclusive carbon atoms.
Claim 6
Dependent Claim
22 words
The compound according to claim 4, in which R 1 is hydrogen and R 3 is the piperidine radical of formula (II).
Claim 7
Dependent Claim
26 words
The compound according to claim 4, in which R 1 and R 3 are identical and each of them is the piperidine radical of formula (II).
Claim 8
Dependent Claim
88 words
The compound according to claim 2, in which x is 0, R 1 is a member selected from hydrogen and the piperidine radical of formula (II), R 2 is alkylene having 2 to 6 inclusive carbon atoms, R 3 is the piperidine radical of formula (II), R 5 , R 6 , R 8 and R 9 are each a methyl group, R 7 is a member selected from hydrogen and methyl, A is hydrogen, B is the group ##STR29## y is an integer from 2 to 100.
Claim 9
Dependent Claim
108 words
A compound according to claim 2, in which x is one, R 1 a member selected from hydrogen and the piperidine radical of formula (II), R 2 is alkylene having 2 to 6 inclusive carbon atoms, R 3 is the piperidine radical of formula (II), R 4 is a member selected from straight and branched chain alkylene having 6 to 10 carbon atoms, m-toluylene, substituted cycloalkylene derived from isophoronediisocyanate, R 5 , R 6 , R 8 and R 9 are methyl, R 7 is a member selected from hydrogen and methyl, A is hydrogen, B is the group ##STR30## y is an integer from 2 to 100.
Claim 10
Dependent Claim
165 words
A compound according to claim 1, in which a proportion of the y units and the terminal group ##STR31## has the radical ##STR32## replaced by the radical selected from ##STR33## wherein R 10 , R 11 , R 12 are similar or different and each of them is individually a member selected from hydrogen, straight and branched chain alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 18 carbon atoms, aryl having 6 to 18 carbon atoms, aralkyl having 7 to 18 carbon atoms, or R 10 and R 11 are linked together so that the group ##STR34## forms a heterocyclic ring having 6 to 8 inclusive members, which contains 2 nitrogen atoms; said proportion of the y units with a replaced radical resulting from using, in the reaction for producing said compound, not over 2 moles of an amine or hydroxyl reactant containing the replacing radicals ##STR35## per one mole of the amine reactant containing the radical ##STR36## employed in the reaction.
Claim 11
Dependent Claim
18 words
A compound according to claim 9, in which R 10 , R 11 , R 12 are hydrogen.
Claim 12
Dependent Claim
77 words
A compound according to claim 10, in which x is 0, R 1 is selected from hydrogen and the piperidine radical of formula (II), R 2 is alkylene having 2 to 6 inclusive carbon atoms, R 3 is the piperidine radical of formula (II), R 5 , R 6 , R 8 and R 9 are methyl groups, R 7 is selected from hydrogen and methyl, A is hydrogen, y is an integer from 2 to 100.
Claim 13
Dependent Claim
91 words
A compound according to claim 10, in which x is 1, R 1 is selected from hydrogen and the piperidine radical of formula (II), R 2 is alkylene having 2 to 6 carbon atoms, R 4 is a member selected from straight and branched chain alkylene having 6 to 10 carbon atoms, m-toluylene, substituted cycloalkylene derived from isophoronediisocyanate, R 5 , R 6 , R 8 and R 9 are individually methyl, R 7 is selected from hydrogen and methyl, A is hydrogen, y is an integer from 2 to 100.
Claim 14
Dependent Claim
26 words
A compound according to claim 9 wherein not over 1 mole of replacing radical ##STR37## is used per mole of amine reactant containing the radical ##STR38##
Claim 15
Dependent Claim
31 words
A synthetic polymer composition of increased light stability having incorporated with the polymer an amount of a compound according to claim 1 effective to increase the light stability of the polymer.
Claim 16
Dependent Claim
11 words
A composition according to claim 14 wherein the compound is (1).
Claim 17
Dependent Claim
11 words
A composition according to claim 14 wherein the compound is (2).
Claim 18
Dependent Claim
13 words
A composition according to claim 14, wherein said synthetic polymer is a polyolefin.
Claim 19
Dependent Claim
12 words
A composition according to claim 17, wherein said synthetic polymer is polypropylene.
Claim 20
Dependent Claim
12 words
A composition according to claim 17, wherein said synthetic polymer is polyethylene.
Claim 21
Dependent Claim
16 words
A composition according to claim 17, wherein said synthetic polymer is in the form of fibers.
Claim 22
Dependent Claim
31 words
A composition according to claim 4, wherein said compound is added to the synthetic polymer composition in an amount from 0.1 to 1% by weight referred to the synthetic polymer composition.
Claim 23
Dependent Claim
28 words
A composition according to claim 14 wherein said compound is added to the synthetic polymer composition in an amount of 0.01 to 5% by weight of the polymer.
Claim 24
Dependent Claim
116 words
A method of preparing a compound according to claim 1 comprising reacting either a diamine having the formula ##STR39## with a reactant selected from the group consisting of carbonyl chloride and OCN--R 4 --NCO in an inert solvent, in a molar ratio of diamine to said reactant ranging from 1:1 to 1.5:1 at a temperature sufficient to form the compound having the formula ##STR40## or employing a corresponding mixture of the diamine ##STR41## with not over 2 moles per mole of said diamine of a compound selected from the group consisting of ##STR42## to form the compound ##STR43## where Z represents a radical ##STR44## m is a number from 0 to 2 and n = y/(1+m).
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-04-24 | 1981-10-24 | 1982-04-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-04-24 | 1985-10-24 | 1986-04-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-04-24 | 1989-10-24 | 1990-04-25 | $7700.00 | Window Closed / Lapsed |