US4788288A
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Self-and Hydroxyl reactive formaldehyde-free cyclic hemiamidal and hemiamide ketal crosslinking monomers
Assignee: Air Products and Chemicals Inc
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Filing: 1987-06-12
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Granted: 1988-11-29
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Expires: 2007-06-12
Abstract
Abstract A compound represented by the following formula: ##STR1## wherein R is a C 3 -C 24 olefinically unsaturated organic radical having functionality which renders the nitrogen atom electron deficient, the olefinic unsaturation functionality being polymerizable, R 1 is hydrogen or a C 1 -C 4 alkyl radical, or R and R 1 together with the nitrogen atom can form an olefinically unsaturated 5 to 7-member ring which has functionality that renders the nitrogen atom electron deficient and the olefinic unsaturation functionality is polymerizable, R 2 and R 3 are hydrogen, a C 1 -C 4 alkyl or acyl radical, or R 2 and R 3 together are a C 2 -C 4 alkylene group, R 4 is hydrogen or a C 1 -C 4 alkyl, acyl, ester, amide or acid group, and n is an integer from 1 to 10, provided n is not 1 when R is (meth)acryloyl, R 2 and R 3 are methyl and R 1 and R 4 are hydrogen. Under acidic conditions the above compounds having R 1 =hydrogen afford cyclic hemiamidals and hemiamide ketals of the following formula ##STR2##
Inventors
- 👤 Robert K. Pinschmidt, Jr.
- 👤 Dale D. Dixon
- 👤 William F. Burgoyne, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 15:11
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/06; C07D239/08; C07D239/10; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/12; C07D207/46; C07D207/48; C07D251/00; C07D251/02; C07D251/12; C07D251/26; C07D251/40; C07D251/54; C07D251/70; C08; C08F; C08F20/00; C08F20/02; C08F20/10; C08F20/34; C08F20/36; C08F20/52; C08F20/54; C08F20/58; C08F22/00; C08F22/36; C08F22/38; C08F26/00; C08F26/06
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
211 words
A compound represented by the following formula: ##STR19## wherein R is an olefinically unsaturated organic radical represented by one of the following formulas ##STR20## where R 5 is a C 2 -C 23 organic radical of the formula ##STR21## where X is hydrogen, C 1 -C 10 alkyl, phenyl, --C(O)NH 2 , or --CO 2 R 8 where R 8 is hydrogen or a C 1 -C 9 alkyl group, Y is --O--, --CH 2 O--, --NR 6 --, --CH 2 NR 6 --, --(CO)--O--(CH 2 ) a --NR 6 --, where R 6 is hydrogen or a C 1 -C 4 alkyl radical and a is 1 to 4, --O(CO)--, --N(CO)--, a branched or unbranched C 1 to C 8 alkylene group, or --C 6 H 4 --, Z is hydrogen, C 1 -C 4 alkyl, --C(O)NH 2 , --CO 2 R 7 where R 7 is hydrogen or a C 1 -C 3 alkyl group, m is 0 or 1; ##STR22## where R 5 is as defined above, Q is hydrogen, hydroxyl, C 1 -C 4 alkoxy or alkylamino, ##STR23## where R 2 is hydrogen or a C 1 -C 4 alkyl group, R 4 is hydrogen or a C 1 -C 4 alkyl group, and n is 4.
Claim 2
Dependent Claim
211 words
A compound represented by the following formula: ##STR19## wherein R is an olefinically unsaturated organic radical represented by one of the following formulas ##STR20## where R 5 is a C 2 -C 23 organic radical of the formula ##STR21## where X is hydrogen, C 1 -C 10 alkyl, phenyl, --C(O)NH 2 , or --CO 2 R 8 where R 8 is hydrogen or a C 1 -C 9 alkyl group, Y is --O--, --CH 2 O--, --NR 6 --, --CH 2 NR 6 --, --(CO)--O--(CH 2 ) a --NR 6 --, where R 6 is hydrogen or a C 1 -C 4 alkyl radical and a is 1 to 4, --O(CO)--, --N(CO)--, a branched or unbranched C 1 to C 8 alkylene group, or --C 6 H 4 --, Z is hydrogen, C 1 -C 4 alkyl, --C(O)NH 2 , --CO 2 R 7 where R 7 is hydrogen or a C 1 -C 3 alkyl group, m is 0 or 1; ##STR22## where R 5 is as defined above, Q is hydrogen, hydroxyl, C 1 -C 4 alkoxy or alkylamino, ##STR23## where R 2 is hydrogen or a C 1 -C 4 alkyl group, R 4 is hydrogen or a C 1 -C 4 alkyl group, and n is 4.
Claim 3
Dependent Claim
11 words
The compound of claim 1 in which R 4 is hydrogen.
Claim 4
Dependent Claim
13 words
The compound of claim 1 in which R 2 is methyl or ethyl.
Claim 5
Dependent Claim
18 words
A compound of claim 1 in which R is R 5 --C(O)-- and R 5 is as defined.
Claim 6
Dependent Claim
22 words
The compound of claim 4 in which the olefinically unsaturated acyl radical is a C 3 -C 10 alpha,beta unsaturated alkenoyl radical.
Claim 7
Dependent Claim
13 words
The compound of claim 5 in which the alkenoyl radical is an acrylyl.
Claim 8
Dependent Claim
18 words
The compound of claim 1 in which R is ##STR24## and R 5 and Q are as defined.
Claim 9
Dependent Claim
14 words
The compound of claim 1 in which R is CH 2 ═CH--SO 2 --.
Claim 10
Dependent Claim
173 words
A compound represented by the following formula: ##STR25## wherein R is an olefinically unsaturated organic radical represented by the following formula ##STR26## where R 5 is a C 2 -C 23 organic radical of the formula ##STR27## where X is hydrogen, C 1 -C 10 alkyl, phenyl, --C(O)NH 2 , --CO 2 R 8 where R 8 is hydrogen or a C 1 -C 9 alkyl group, Y is --O--, --CH 2 O--, --NR 6 --, --CH 2 NR 6 --, --(CO)--O--(CH 2 ) a --NR 6 --, where R 6 is hydrogen or a C 1 -C 4 alkyl radical and a is 1 to 4, --O(CO)--, --N(CO)--, a branched or unbranched C 1 to C 8 alkylene group, or --C 6 H 4 --, Z is hydrogen, C 1 -C 4 alkyl, --C(O)NH 2 , --CO 2 R 7 where R 7 is hydrogen or a C 1 -C 3 alkyl group, m is 0 or 1, R 2 is a C 1 -C 4 alkyl group, and n is 4.
Claim 11
Dependent Claim
173 words
A compound represented by the following formula: ##STR25## wherein R is an olefinically unsaturated organic radical represented by the following formula ##STR26## where R 5 is a C 2 -C 23 organic radical of the formula ##STR27## where X is hydrogen, C 1 -C 10 alkyl, phenyl, --C(O)NH 2 , --CO 2 R 8 where R 8 is hydrogen or a C 1 -C 9 alkyl group, Y is --O--, --CH 2 O--, --NR 6 --, --CH 2 NR 6 --, --(CO)--O--(CH 2 ) a --NR 6 --, where R 6 is hydrogen or a C 1 -C 4 alkyl radical and a is 1 to 4, --O(CO)--, --N(CO)--, a branched or unbranched C 1 to C 8 alkylene group, or --C 6 H 4 --, Z is hydrogen, C 1 -C 4 alkyl, --C(O)NH 2 , --CO 2 R 7 where R 7 is hydrogen or a C 1 -C 3 alkyl group, m is 0 or 1, R 2 is a C 1 -C 4 alkyl group, and n is 4.
Claim 12
Dependent Claim
22 words
The compounds of claim 9 in which the olefinically unsaturated acyl radical is a C 3 -C 10 alpha,beta unsaturated alkenoyl radical.
Claim 13
Dependent Claim
14 words
The compounds of claim 10 in which the alkenoyl radical is acrylyl or methacrylyl.
Claim 14
Dependent Claim
13 words
The compounds of claim 9 in which R 2 is methyl or ethyl.
Claim 15
Dependent Claim
13 words
The compounds of claim 10 in which R 2 is methyl or ethyl.
Claim 16
Dependent Claim
13 words
The compounds of claim 11 in which R 2 is methyl or ethyl.
Claim 17
Dependent Claim
32 words
A compound represented by the formula ##STR28## wherein R 2 is a C 1 -C 4 alkyl radical, R 5 is a C 3 -C 10 alkenoyl radical, and n is 4.
Claim 18
Dependent Claim
32 words
A compound represented by the formula ##STR28## wherein R 2 is a C 1 -C 4 alkyl radical, R 5 is a C 3 -C 10 alkenoyl radical, and n is 4.
Claim 19
Dependent Claim
14 words
The compounds of claim 15 in which the alkenoyl radical is acrylyl or methacrylyl.
Claim 20
Dependent Claim
13 words
The compounds of claim 16 in which R 2 is methyl or ethyl.
Claim 21
Dependent Claim
12 words
A compound of the formula ##STR29## where R is methyl or ethyl.
Claim 22
Dependent Claim
12 words
A compound of the formula ##STR29## where R is methyl or ethyl.
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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) | 1991-11-29 | 1992-05-30 | 1992-11-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-11-29 | 1996-05-30 | 1996-11-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-11-29 | 2000-05-30 | 2000-11-29 | $7700.00 | Window Closed / Lapsed |