US4101522A
Expired / Lapsed
US
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Azo compounds containing acylating function and azo containing polymers
Assignee: Arkema Inc
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Filing: 1976-02-25
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Granted: 1978-07-18
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Expires: 1996-02-25
Abstract
Abstract A. A novel class of azo compounds R-N═N-R 1 where R and/or R 1 are groups containing an acylating function, e.g., acyl chloride, chloroformate or anhydride. Example: Cis-4,4'-Azobis-(4-cyanovaleryl chloride). B. a novel class of azo containing polymers (R'--N═N--C(R.sub.2)(R.sub.2 ') --R.sub.2 "--Y).sub.m --E--(Z).sub.n wherein R' is t-aliphatic, formed by reacting a polymer having at least one group reactive with an acyl group and a compound as in "A" containing only one acylating function. Example: the reaction product of 4-t-butylazo-4-cyanovaleryl chloride and hydroxyl terminated polybutadiene liquid resin. C. a novel class of azo containing polymers Z(E--Y--R.sub.2 "--C(R.sub.2)(R.sub.2 ')--N═N--C(R.sub.2)(R.sub.2 ')--R 2 "--Y) m' --E--Z, formed by the reaction of a compound as in "A" having two acylating functions with (1) a monomer having two acyl-reactive groups and a monomer having two acylating functions, or (2) a polymer having at least one acyl-reactive group. D. polymers B and C are useful in the production of block and graft polymers and in curing unsaturated polyester resin-vinyl monomer systems. Polymer C forms block and graft polymers with vinyl monomers with substantially no formation of homopolymers. These block and graft polymers are compatibilizing agents for solutions of homopolymers.
Inventors
- 👤 Chester Stephen Sheppard
- 👤 Ronald Edward MacLeay
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 00:27
CPC Classifications
C; C08; C08G; C08G73/00; C08F; C08F299/00; C08F299/02; C08F299/04; C08F299/0442; C08F299/0457
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
274 words
A polymer having the formula: ##STR66## or ##STR67## wherein: (a) R' is t-aliphatic having 4-10 carbon atoms; (b) R 2 is lower alkyl of 1 to 8 carbons; (c) R' 2 is --CN, --C(═O)OR 6 , --OC(═O)R 6 , --CL, --Br, --OC(═O)H, --GC(═G)R 5 , --GC(═G)GR 5 , --GR 5 , --N 3 , --SCN, --NCS, --OCN, --OOR 8 , --R 5 , ##STR68## (d) R 2 " is aliphatic of 1 to 10 carbons, aromatic of 6 to 12 carbons, aromatic-aliphatic of 7 to 20 carbons, or cycloaliphatic of 3 to 10 carbons; (e) R 2 and R 2 ", when taken together with the tertiary carbon atom connected to the azo nitrogen atom, form a cycloaliphatic triradical of 3-10 carbons. (f) Y is a divalent radical selected from --C(═O)O--, --OC(═O)O--, and, --OC(═O)R 3 (COOH)C(═O)O--, (g) R 3 is an aromatic of 6 to 12 carbons, aliphatic of 1 to 10 carbons, or cycloaliphatic of 3 to 10 carbons; (h) R 5 is an alkyl or cycloalkyl radical of 1-12 carbons or an aromatic radical of 6-12 carbons; (i) R 6 is alkyl of 1 to 6 carbons; (j) R 7 is H, alkyl or cycloalkyl of 1-10 carbons, or aromatic of 6-12 carbons; (k) R 8 is tertiary aliphatic of 4 to 10 carbons; (l) R 9 is lower alkylene of 1 to 6 carbons; (m) G is oxygen or sulfur; (n) E is a divalent residue of a polyester; (o) m is 1 to 2; n is 0 to 1 and m plus n is 2; (p) m' is 1 to 100; and (q) Z is selected from -OH, and --H.
Claim 2
Dependent Claim
274 words
A polymer having the formula: ##STR66## or ##STR67## wherein: (a) R' is t-aliphatic having 4-10 carbon atoms; (b) R 2 is lower alkyl of 1 to 8 carbons; (c) R' 2 is --CN, --C(═O)OR 6 , --OC(═O)R 6 , --CL, --Br, --OC(═O)H, --GC(═G)R 5 , --GC(═G)GR 5 , --GR 5 , --N 3 , --SCN, --NCS, --OCN, --OOR 8 , --R 5 , ##STR68## (d) R 2 " is aliphatic of 1 to 10 carbons, aromatic of 6 to 12 carbons, aromatic-aliphatic of 7 to 20 carbons, or cycloaliphatic of 3 to 10 carbons; (e) R 2 and R 2 ", when taken together with the tertiary carbon atom connected to the azo nitrogen atom, form a cycloaliphatic triradical of 3-10 carbons. (f) Y is a divalent radical selected from --C(═O)O--, --OC(═O)O--, and, --OC(═O)R 3 (COOH)C(═O)O--, (g) R 3 is an aromatic of 6 to 12 carbons, aliphatic of 1 to 10 carbons, or cycloaliphatic of 3 to 10 carbons; (h) R 5 is an alkyl or cycloalkyl radical of 1-12 carbons or an aromatic radical of 6-12 carbons; (i) R 6 is alkyl of 1 to 6 carbons; (j) R 7 is H, alkyl or cycloalkyl of 1-10 carbons, or aromatic of 6-12 carbons; (k) R 8 is tertiary aliphatic of 4 to 10 carbons; (l) R 9 is lower alkylene of 1 to 6 carbons; (m) G is oxygen or sulfur; (n) E is a divalent residue of a polyester; (o) m is 1 to 2; n is 0 to 1 and m plus n is 2; (p) m' is 1 to 100; and (q) Z is selected from -OH, and --H.
Claim 3
Dependent Claim
10 words
A polymer according to claim 1 having the formula: ##STR69##
Claim 4
Dependent Claim
10 words
A polymer according to claim 1 having the formula: ##STR70##
Claim 5
Dependent Claim
10 words
A polymer according to claim 1 having the formula: ##STR71##
Claim 6
Dependent Claim
10 words
A polymer according to claim 1 having the formula: ##STR72##
Claim 7
Dependent Claim
284 words
A polymer or polymeric reaction product having the formula: ##STR73## wherein: (a) R' is t-aliphatic having 4-10 carbon atoms; (b) R 2 is lower alkyl of 1 to 8 carbons; (c) R' 2 is --CN, --C(═O)OR 6 , --OC(═O)R 6 , --Cl, --Br, --OC(═O)H, --GC(═G)R 5 , --GC(═G)GR 5 , --GR 5 , --N 3 , --SCN, --NCS, --OCN, --OOR 8 , --R 5 , ##STR74## (d) R 2 " is aliphatic of 1 to 10 carbons, aromatic of 6 to 12 carbons, aromatic-aliphatic of 7 to 20 carbons, or cycloaliphatic of 3 to 10 carbons; (e) R 2 and R 2 ", when taken together with the tertiary carbon atom connected to the azo nitrogen atom, form a cycloaliphatic triradical of 3-10 carbons. (f) Y is a divalent radical selected from --C(═O)O--, --OC(═O)O--, --C(═O)S--, --OC(═O)S--, --OC(═O)R 3 (COOH)C(═O)O--, and --OC(═0)R 3 (COOH)C(═O)S--; (g) R 3 is an aromatic of 6 to 12 carbons, aliphatic of 1 to 10 carbons, or cycloaliphatic of 3 to 10 carbons; (h) R 5 is an alkyl or cycloalkyl radical of 1-12 carbons or an aromatic radical of 6-12 carbons; (i) R 6 is alkyl of 1 to 6 carbons; (j) R 7 is H, alkyl or cycloalkyl of 1-10 carbons, or aromatic of 6-12 carbons; (k) R 8 is tertiary aliphatic of 4 to 10 carbons; (l) R 9 is lower alkylene of 1 to 6 carbons; (m) G is oxygen or sulfur; (n) E is a divalent residue of a polyester; (o) m is 1 to 2; n is 0 to 1 and m plus n is 2; (p) m' is 1 to 100 and (q) Z is selected from --OH, --SH, --OR 2 and --H.
Claim 8
Dependent Claim
284 words
A polymer or polymeric reaction product having the formula: ##STR73## wherein: (a) R' is t-aliphatic having 4-10 carbon atoms; (b) R 2 is lower alkyl of 1 to 8 carbons; (c) R' 2 is --CN, --C(═O)OR 6 , --OC(═O)R 6 , --Cl, --Br, --OC(═O)H, --GC(═G)R 5 , --GC(═G)GR 5 , --GR 5 , --N 3 , --SCN, --NCS, --OCN, --OOR 8 , --R 5 , ##STR74## (d) R 2 " is aliphatic of 1 to 10 carbons, aromatic of 6 to 12 carbons, aromatic-aliphatic of 7 to 20 carbons, or cycloaliphatic of 3 to 10 carbons; (e) R 2 and R 2 ", when taken together with the tertiary carbon atom connected to the azo nitrogen atom, form a cycloaliphatic triradical of 3-10 carbons. (f) Y is a divalent radical selected from --C(═O)O--, --OC(═O)O--, --C(═O)S--, --OC(═O)S--, --OC(═O)R 3 (COOH)C(═O)O--, and --OC(═0)R 3 (COOH)C(═O)S--; (g) R 3 is an aromatic of 6 to 12 carbons, aliphatic of 1 to 10 carbons, or cycloaliphatic of 3 to 10 carbons; (h) R 5 is an alkyl or cycloalkyl radical of 1-12 carbons or an aromatic radical of 6-12 carbons; (i) R 6 is alkyl of 1 to 6 carbons; (j) R 7 is H, alkyl or cycloalkyl of 1-10 carbons, or aromatic of 6-12 carbons; (k) R 8 is tertiary aliphatic of 4 to 10 carbons; (l) R 9 is lower alkylene of 1 to 6 carbons; (m) G is oxygen or sulfur; (n) E is a divalent residue of a polyester; (o) m is 1 to 2; n is 0 to 1 and m plus n is 2; (p) m' is 1 to 100 and (q) Z is selected from --OH, --SH, --OR 2 and --H.
Claim 9
Dependent Claim
10 words
A polymer according to claim 6 having the formula: ##STR75##
Claim 10
Dependent Claim
15 words
A polymer according to claim 6 having the formula: ##STR76## and which is a liquid.
Claim 11
Dependent Claim
15 words
A polymer according to claim 6 having the formula: ##STR77## and which is a liquid.
Claim 12
Dependent Claim
16 words
A polymer according to claim 6 having the formula: ##STR78## and which is a rubbery solid.
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) | 1981-07-17 | 1982-01-16 | 1982-07-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-07-17 | 1986-01-16 | 1986-07-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-07-17 | 1990-01-16 | 1990-07-18 | $7700.00 | Window Closed / Lapsed |