US4537924A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Quadratic acid amide derivatives, their use as stabilizers, and synthetic resins treated therewith
Assignee: CHEMICHE WERKE HUELS AG
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Filing: 1983-09-14
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Granted: 1985-08-27
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Expires: 2003-09-14
Abstract
Abstract Quadratic acid bisamides and salts thereof having the formula I are effective stabilizers of synthetic resins, especially for imparting resistance to deterioration resulting from exposure to light ##STR1## wherein R 1 is H, C 1-12 alkyl or OH-substituted C 2-12 alkyl; R 2 is --(CH 2 ) m --O-- n , wherein m is an integer of 2-6; n is 0 or 1; R 3 is H, CH 3 , CH 2 --CH 2 --OH, CH 2 --COOH or CH 2 --CH 2 --COOH; HX is an acid equivalent of an unsubstituted or substituted monobasic, dibasic or polybasic organic acid of not more than 20 carbon atoms, or of sulfuric or phosphoric acid; and 0≦p≦2.
Inventors
- 👤 Konrad Rombusch
- 👤 Gunther Maahs
- 👤 Wolfgang Schafer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 06:27
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; C07D211/40; C07D211/44; C07D211/46; C07D211/56; C07D211/58
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
99 words
A quadratic acid bisamide or salt thereof having the formula ##STR5## wherein R 1 is H, C 1-12 alkyl or OH-substituted C 2-12 alkyl; R 2 is --(CH 2 ) m --O-- n , wherein m is an integer of 2-6; n is 0 or 1; R 3 is H, CH 3 , CH 2 --CH 2 --OH, CH 2 --COOH or CH 2 --CH 2 --COOH; HX is an acid equivalent of an unsubstituted or substituted monobasic, dibasic or polybasic organic acid of not more than 20 carbon atoms, or of sulfuric or phosphoric acid; and ≦ p≦2.
Claim 2
Dependent Claim
99 words
A quadratic acid bisamide or salt thereof having the formula ##STR5## wherein R 1 is H, C 1-12 alkyl or OH-substituted C 2-12 alkyl; R 2 is --(CH 2 ) m --O-- n , wherein m is an integer of 2-6; n is 0 or 1; R 3 is H, CH 3 , CH 2 --CH 2 --OH, CH 2 --COOH or CH 2 --CH 2 --COOH; HX is an acid equivalent of an unsubstituted or substituted monobasic, dibasic or polybasic organic acid of not more than 20 carbon atoms, or of sulfuric or phosphoric acid; and ≦ p≦2.
Claim 3
Dependent Claim
27 words
A compound according to claim 1, wherein R 1 is C 3-8 alkyl; R 2 is a valence bond; R 3 is H; and p is 0.
Claim 4
Dependent Claim
22 words
A compound according to claim 1, wherein R 1 and R 3 are each H; and R 2 is a valence bond.
Claim 5
Dependent Claim
10 words
A compound according to claim 3, wherein p is 0.
Claim 6
Dependent Claim
22 words
A compound according to claim 3, wherein p is >0; and HX is an acid equivalent of dodecane-1,12-dioic acid or stearic acid.
Claim 7
Dependent Claim
7 words
1,3-Bis[N-n-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]cyclobutenediylium-2,4-diolate, a compound according to claim 1.
Claim 8
Dependent Claim
7 words
1,3-Bis[N-isobutyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]cyclobutenediylium-2,4-diolate, a compound according to claim 1.
Claim 9
Dependent Claim
7 words
1,3-Bis[N-n-hexyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino]cyclobutenediylium-2,4-diolate, a compound according to claim 1.
Claim 10
Dependent Claim
7 words
1,3-Bis[2,2,6,6-tetramethyl-4-piperidyloxypropylamino]cyclobutenediylium-2,4-diolate, a compound according to claim 1.
Claim 11
Dependent Claim
129 words
In a synthetic resin comprising an effective stabilizing amount of a stabilizer for imparting resistance to weathering, especially deterioration resulting from exposure to light, the improvement wherein said stabilizer is a quadratic acid bisamide or salt thereof having the formula ##STR6## wherein R 1 is H, C 1-12 alkyl or OH-substituted C 2-12 alkyl; R 2 is --(CH 2 ) m --O-- n , wherein m is an integer of 2-6; n is 0 or 1; R 3 is H, CH 3 , CH 2 --CH 2 --OH, CH 2 --COOH or CH 2 --CH 2 --COOH; HX is an acid equivalent of an unsubstituted or substituted monobasic, dibasic or polybasic organic acid of not more than 20 carbon atoms, or of sulfuric or phosphoric acid; and ≦ p≦2.
Claim 12
Dependent Claim
129 words
In a synthetic resin comprising an effective stabilizing amount of a stabilizer for imparting resistance to weathering, especially deterioration resulting from exposure to light, the improvement wherein said stabilizer is a quadratic acid bisamide or salt thereof having the formula ##STR6## wherein R 1 is H, C 1-12 alkyl or OH-substituted C 2-12 alkyl; R 2 is --(CH 2 ) m --O-- n , wherein m is an integer of 2-6; n is 0 or 1; R 3 is H, CH 3 , CH 2 --CH 2 --OH, CH 2 --COOH or CH 2 --CH 2 --COOH; HX is an acid equivalent of an unsubstituted or substituted monobasic, dibasic or polybasic organic acid of not more than 20 carbon atoms, or of sulfuric or phosphoric acid; and ≦ p≦2.
Claim 13
Dependent Claim
23 words
A stabilized resin according to claim 10, wherein said effective stabilizing amount is 0.01-2% by weight, based on the weight of the resin.
Claim 14
Dependent Claim
18 words
A stabilized resin according to claim 11, which is a polyester, polyether ester, polyether ester amide or polyurethane.
Claim 15
Dependent Claim
11 words
A stabilized resin according to claim 11, which is a polyamide.
Claim 16
Dependent Claim
138 words
In a method of stabilizing a synthetic resin for imparting resistance to weathering, especially deterioration resulting from exposure to light, wherein an effective stabilizing amount of a stabilizer is incorporated in said resin, the improvement wherein said stabilizer is a quadratic acid bisamide or salt thereof having the formula ##STR7## wherein R 1 is H, C 1-12 alkyl or OH-substituted C 2-12 alkyl; R 2 is --(CH 2 ) m --O-- n , wherein m is an integer of 2-6; n is 0 or 1; R 3 is H, CH 3 , CH 2 --CH 2 --OH, CH 2 --COOH or CH 2 --CH 2 --COOH; HX is an acid equivalent of an unsubstituted or substituted monobasic, dibasic or polybasic organic acid of not more than 20 carbon atoms, or of sulfuric or phosphoric acid; and ≦ p≦2.
Claim 17
Dependent Claim
138 words
In a method of stabilizing a synthetic resin for imparting resistance to weathering, especially deterioration resulting from exposure to light, wherein an effective stabilizing amount of a stabilizer is incorporated in said resin, the improvement wherein said stabilizer is a quadratic acid bisamide or salt thereof having the formula ##STR7## wherein R 1 is H, C 1-12 alkyl or OH-substituted C 2-12 alkyl; R 2 is --(CH 2 ) m --O-- n , wherein m is an integer of 2-6; n is 0 or 1; R 3 is H, CH 3 , CH 2 --CH 2 --OH, CH 2 --COOH or CH 2 --CH 2 --COOH; HX is an acid equivalent of an unsubstituted or substituted monobasic, dibasic or polybasic organic acid of not more than 20 carbon atoms, or of sulfuric or phosphoric acid; and ≦ p≦2.
Claim 18
Dependent Claim
22 words
A method according to claim 14, wherein said effective stabilizing amount is 0.01-2% by weight, based on the weight of the resin.
Claim 19
Dependent Claim
19 words
A method according to claim 14, wherein said resin is a polyester, polyether ester, polyether ester amide or polyurethane.
Claim 20
Dependent Claim
12 words
A method according to claim 14, wherein said resin is a polyamide.
Claim 21
Dependent Claim
10 words
A compound according to claim 1, wherein n is 1.
Claim 22
Dependent Claim
11 words
A stabilized resin according to claim 10, wherein n is 1.
Claim 23
Dependent Claim
10 words
A method according to claim 14, wherein n is 1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-08-26 | 1989-02-25 | 1989-08-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-26 | 1993-02-25 | 1993-08-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-26 | 1997-02-25 | 1997-08-27 | $7700.00 | Window Closed / Lapsed |