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EP0433034A2 Expired / Lapsed EP ⏱️ 0.0 years remaining

Method involving thermally sensitive alpha-amidoacetyl or beta-amidopropionyl linkages

Assignee: 3M Co
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Filing: 1990-12-12
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Granted: —
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Expires: 2010-12-12
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Abstract

Abstract Compounds containing alpha-amidoacetyl linkages are described that are thermally labile and yield nucleophilic and azlactone products. Nucleophiles are useful as curing agents for epoxy resin sealants and adhesives and azlactones are useful in crosslinking systems for polymers.

Inventors

  • 👤 Larry R. C/O Minnesota Mining And Krepski
  • 👤 Steven M. C/O Minnesota Mining And Heilmann
  • 👤 M. Dean C/0 Minnesota Mining And Moren
  • 👤 K Jerald C/O Minnesota Mining And Rasmunssen

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-27 12:05
CPC Classifications
C; C07; C07D; C07D265/00; C07D265/04; C07D265/06; C07D265/08; C07D265/10; C07D263/00; C07D263/02; C07D263/30; C07D263/34; C07D263/36; C07D263/42; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014; C08G59/50; C08G59/5046; C08G73/00

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 22 words
A method comprising the step: heating a compound comprising an alpha-amidoacetyl or beta-amidopropionyl structural linkage to provide an azlactone and a nucleophile.
Claim 2
Dependent Claim 326 words
A method according to claim 1 wherein said compound has the formula: wherein G is an alkyl, alkenyl, aryl, or cycloakyl, or monovalent terminal group having a number average molecular weight in the range of 15 to infinity; or an alkylene, alkenylene, arylene, cycloalkeylene or polyvalent polymeric linking group having a number average molecular weight in the range of 14 to infinity; or a carbon-to-carbon covalent bond; p is the valence of G and can have any positive integral value from 1 to infinity; m can have any positive integral value from 1 to P; R¹ and R² independently represent an alkyl group of 1 to 14 carbon atoms, a cycloalkyl group of 3 to 12 carbon atoms, an aryl group of 5 to 12 ring atoms, or R¹ and R² taken together with the carbon atom to which they are joined form a carbocyclic ring of 4 to 12 ring atoms; R³ and R⁴ are independently hydrogen or lower alkyl; n is 0 or 1; A is selected from the group consisting of ―SR⁵-R⁶, wherein R⁵ can be alkylene or arylene containing 1 to 14 carbon atoms and 5 to 12 ring atoms, respectively, and R⁶ can be hydrogen or G; -OH; -O-Ar-R⁶, wherein Ar is arylene of 5 to 12 ring atoms, wherein R⁶ is as defined above; -OCHR⁷R F R⁸, wherein R⁷ can be hydrogen or R F , R F is a substantially perfluorinated alkylene or cycloalkylene group from 2 to 14 carbon atoms, and R⁸ can be hydrogen, fluorine, or G (defined above); or substantially perfluorinated R⁷ and R F together with the carbon atom to which they are joined form a carbocyclic ring of 4 to 12 ring atoms; wherein R¹, R², R⁵, and R⁶ are as defined above or R¹, R², and R⁶ together with the atoms to which they are joined form a ring of 4 to 12 ring atoms, and R⁹ can be alkyl, cycloalkyl, or aryl.
Claim 3
Dependent Claim 82 words
The method according to claim 2 wherein G further comprises one or more of S, non-peroxidic O, N, P, S, Br, Cl, F, and Si atoms, or wherein G further comprises one or more functional groups selected from the group consisting of alkyl, alkenyl, aryl, amide, ester, nitrile, nitro, sulfide, sulfoxide, sulfone, disulfide, azide, isothiocyanate, amine, hydroxyl, mercaptan, ether, urethane, quaternary ammonium and phosphonium, halogen, silyl, and silyloxy, said functional group optionally being substituted by at least one alkyl or aryl group.
Claim 4
Independent Claim 20 words
The method according to claims 1 to 3 wherein said heating step takes place at a temperature less than 250°C.
Claim 5
Independent Claim 20 words
The method according to claims 1 to 4 wherein said azlactone is a monoazlactone or an azlactone homopolymer or copolymer.
Claim 6
Independent Claim 135 words
The method according to claims 1 to 5 wherein said nucleophile is 1) a thiol having the formula HSR⁵R⁶, wherein R⁵ and R⁶ are as previously defined, 2) water, 3) a phenol having the formula HO-Ar-R⁶, wherein Ar is an aromatic group having 5 to 12 ring atoms wherein the aromatic group can have a single ring or a multi or fused ring system, and R⁶ is as previously defined, 4) an alcohol having the formula HOCHR⁷R F R⁸ wherein R⁷, R⁸, and R F are as previously defined, 5) a secondary amine having the formula HN(R¹)R⁵R⁶ wherein R¹, R⁵ and R⁶ are as previously defined, 6) an amidine having the formula wherein R¹, R², R⁵, R⁶ are as previously defined, 7) a HN=C-(NR¹R²)-NR⁵R⁶ wherein R¹, R², R⁵, R⁶ and R⁹ are as previously defined.
Claim 7
Independent Claim 16 words
The method according to claims 1 to 6 wherein said nucleophile is a substantially perfluorinated alcohol.
Claim 8
Independent Claim 25 words
The method according to claims 1 to 7 wherein the heating step takes place in the presence of a chemically effective amount of a catalyst.
Claim 9
Independent Claim 25 words
The method according to claims 1 to 8 wherein said heating step takes place in the presence of a solvent for the azlactone and nucleophile.

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