US4319032A
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US
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Derivatives of aminoalkyl alkylene ureas
Assignee: Syensqo USA LLC
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Filing: 1980-06-06
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Granted: 1982-03-09
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Expires: 2000-06-06
Abstract
Abstract The invention provides new compounds which are cyclic alkylene ureas having hydroxyl and amine functionalities and which are produced by the reaction of an omega-amine alkyl alkylene urea, such as 2-aminoethyl ethylene urea, with an unsaturated glycidyl ether or ester, such as allyl glycidyl ether. The new compounds are monomers which may be incorporated in aqueous emulsion polymer systems and are useful as wet adhesion promoters for latex paints.
Inventors
- 👤 Joseph M. Sandri
- 👤 John W. Calentine
- 👤 Seymour M. Linder
- 👤 Yves J. Billoux
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 15:12
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/04; C07D233/28; C07D233/30; C07D233/32; C07D233/36; C08; C08F; C08F16/00; C08F16/12; C08F16/14; C08F16/28; C08F20/00; C08F20/02; C08F20/10; C08F20/34; C08F20/36; C08F216/00; C09; C09D; C09D4/00; C09J; C09J4/00
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
480 words
A compound having the formula: ##STR50## where R 1 is alkylene having 2 to 3 carbon atoms; R 2 is alkylene having 2 to about 10 carbon atoms; R 3 is H or CH 3 ; R 4 is H or CH 3 and may be the same as or different from R 3 ; Q 1 is (R 5 --O) m where m is zero or an integer from 1 to about 100, and R 5 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms; ##STR51## where t is zero or an integer from 1 to 10; Q 3 is (O--R 6 ) n where n is zero or an integer from 1 to about 100 and may be the same as or different from m, and R 6 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 ; ##STR52## where Q 4 is (R 7 --O) p where p is zero or an integer from 1 to about 100 and may be the same as or different from m and n, and R 7 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 or R 6 ; Q 5 is (O--R 8 ) q where q is zero or an integer from 1 to about 100 and may be the same as or different from m, n and p, and R 8 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 and R 7 ; and ##STR53## where Q 6 is (R 9 --O) r where r is zero or an integer from 1 to about 100 and may be the same as or different from m, n, p and q, and R 9 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 , R 7 and R 8 ; and Q 7 is (O-R 10 ) s where s is zero or an integer from 1 to about 100 and may be the same as or different from m, n, p, q and r, and R 10 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 , R 7 , R 8 , and R 9 .
Claim 2
Dependent Claim
480 words
A compound having the formula: ##STR50## where R 1 is alkylene having 2 to 3 carbon atoms; R 2 is alkylene having 2 to about 10 carbon atoms; R 3 is H or CH 3 ; R 4 is H or CH 3 and may be the same as or different from R 3 ; Q 1 is (R 5 --O) m where m is zero or an integer from 1 to about 100, and R 5 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms; ##STR51## where t is zero or an integer from 1 to 10; Q 3 is (O--R 6 ) n where n is zero or an integer from 1 to about 100 and may be the same as or different from m, and R 6 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 ; ##STR52## where Q 4 is (R 7 --O) p where p is zero or an integer from 1 to about 100 and may be the same as or different from m and n, and R 7 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 or R 6 ; Q 5 is (O--R 8 ) q where q is zero or an integer from 1 to about 100 and may be the same as or different from m, n and p, and R 8 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 and R 7 ; and ##STR53## where Q 6 is (R 9 --O) r where r is zero or an integer from 1 to about 100 and may be the same as or different from m, n, p and q, and R 9 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 , R 7 and R 8 ; and Q 7 is (O-R 10 ) s where s is zero or an integer from 1 to about 100 and may be the same as or different from m, n, p, q and r, and R 10 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 , R 7 , R 8 , and R 9 .
Claim 3
Dependent Claim
76 words
A compound according to claim 1 wherein R 2 is ethylene, propylene or butylene; Q 1 is (C 2 H 4 --O) m or (C 3 H 5 --O) m and m is zero or an integer from 1 to 100; Q 3 is (O--C 2 H 4 ) n and n is zero or an integer from 1 to 100; A is H or ##STR54## and A 1 is H or the same as A.
Claim 4
Dependent Claim
50 words
A compound according to claim 1 having the formula: ##STR55## where R 1 , R 2 , R 3 , R 4 and Y are as defined in claim 1; Q 2 is ##STR56## ##STR57## A is H or ##STR58## and A 1 is H or the same as A.
Claim 5
Dependent Claim
12 words
A compound according to claim 3 wherein Y is CH 2 .
Claim 6
Dependent Claim
10 words
A compound according to claim 3 wherein Y is ##STR59##
Claim 7
Dependent Claim
26 words
A compound selected from the group consisting of: ##STR60## ##STR61## where Q 2 is ##STR62## and A 1 is Q 2 --O--CH 2 --CH═CH 2 .
Claim 8
Dependent Claim
26 words
A compound selected from the group consisting of: ##STR60## ##STR61## where Q 2 is ##STR62## and A 1 is Q 2 --O--CH 2 --CH═CH 2 .
Claim 9
Dependent Claim
121 words
A composition of matter made by reacting (1) an unsaturated glycidyl ether or ester having the formula: ##STR63## where R 3 is H or CH 3 ; R 4 is H or CH 3 and may be the same as or different from R 3 ; ##STR64## Q 3 is (O--R 6 ) n where n is zero or an integer from 1 to about 100 and R 6 is a linear or branched alkylene, alkoxylalkylene, cycloalkylene, cycloalkoxyalkylene, arylakylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, with (2) an omega-amino alkylene urea having the formula: ##STR65## where R 1 is alkylene having 2 to 3 carbon atoms; R 2 is alkylene having 2 to about 20 carbon atoms;
Claim 10
Dependent Claim
121 words
A composition of matter made by reacting (1) an unsaturated glycidyl ether or ester having the formula: ##STR63## where R 3 is H or CH 3 ; R 4 is H or CH 3 and may be the same as or different from R 3 ; ##STR64## Q 3 is (O--R 6 ) n where n is zero or an integer from 1 to about 100 and R 6 is a linear or branched alkylene, alkoxylalkylene, cycloalkylene, cycloalkoxyalkylene, arylakylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, with (2) an omega-amino alkylene urea having the formula: ##STR65## where R 1 is alkylene having 2 to 3 carbon atoms; R 2 is alkylene having 2 to about 20 carbon atoms;
Claim 11
Dependent Claim
232 words
Q 1 is (R 5 --O m where m is zero or an integer from 1 to about 100 and R 5 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylakylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 6 Q 4 is (R 7 --O) p where p is zero or an integer from 1 to about 100 and may be the same as or different from m, and R 7 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 and R 6 and Q 6 is (R 9 --O) r where r is zero or an integer from 1 to about 100 and may be the same as or different from m and p, and R 9 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 and R 7 , in a molar ratio of from about 0.5 to about 10 moles of unsaturated glycidyl ether or ester per mole of omega-amino alkylene urea and at a temperature in the range of from about 50° C. to about 250° C.
Claim 12
Dependent Claim
232 words
Q 1 is (R 5 --O m where m is zero or an integer from 1 to about 100 and R 5 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylakylene or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 6 Q 4 is (R 7 --O) p where p is zero or an integer from 1 to about 100 and may be the same as or different from m, and R 7 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 and R 6 and Q 6 is (R 9 --O) r where r is zero or an integer from 1 to about 100 and may be the same as or different from m and p, and R 9 is a linear or branched alkylene, alkoxyalkylene, cycloalkylene, cycloalkoxyalkylene, arylalkylene, or aryloxyalkylene residue having 2 to about 20 carbon atoms, and may be the same as or different from R 5 , R 6 and R 7 , in a molar ratio of from about 0.5 to about 10 moles of unsaturated glycidyl ether or ester per mole of omega-amino alkylene urea and at a temperature in the range of from about 50° C. to about 250° C.
Claim 13
Dependent Claim
40 words
A composition of matter according to claim 7 wherein the unsaturated glycidyl ether or ester is an ether having the formula: ##STR66## where R 3 is H or CH 3 ; and R 4 is H or CH 3 .
Claim 14
Dependent Claim
40 words
A composition of matter according to claim 7 wherein the omega-amino alkylene urea has the formula: ##STR67## where R 1 is alkylene having 2 to 3 carbon atoms; and R 2 is alkylene having 2 to about 10 carbon atoms.
Claim 15
Dependent Claim
48 words
A composition of matter made by reacting allyl glycidyl ether with 2-aminoethyl ethylene urea in a molar ratio of from about 0.5 to about 10 moles of allyl glycidyl ether per mole of 2-aminoethyl ethylene urea at a temperature of from about 50° C. to about 250° C.
Claim 16
Dependent Claim
48 words
A composition of matter made by reacting allyl glycidyl ether with 2-aminoethyl ethylene urea in a molar ratio of from about 0.5 to about 10 moles of allyl glycidyl ether per mole of 2-aminoethyl ethylene urea at a temperature of from about 50° C. to about 250° C.
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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) | 1985-03-08 | 1985-09-07 | 1986-03-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-03-08 | 1989-09-07 | 1990-03-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-03-08 | 1993-09-07 | 1994-03-09 | $7700.00 | Window Closed / Lapsed |