← Back to Patent Explorer
EP0449488A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Azlactone Michael adducts

Assignee: 3M Co
•
Filing: 1991-03-20
•
Granted: —
•
Expires: 2011-03-20
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Azlactone-functional Michael adducts are disclosed which are the Michael reaction products of 2-alkenyl azlactones and Michael donors selected from carbon and nitrogen nucleophiles. Reaction products which contain a plurality of azlactone groups are useful as step growth monomers in adhesives, sealants, and coatings.

Inventors

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

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-26 09:48
CPC Classifications
C; C07; C07D; C07D265/00; C07D265/04; C07D265/06; C07D263/00; C07D263/02; C07D263/30; C07D263/34; C07D263/36; C07D263/42

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 477 words
An azlactone-functional adduct having the formula wherein p¹ and p² independently have integral values of 1 to (the valence of X¹ or X²) -1, where p¹ relates to X¹ and p² to X²; R¹, R², R⁷, and R⁸ independently represent an alkyl group, a cycloalkyl group, an aryl group, or at least one of (R¹ and R²) and (R⁷ and R⁸) taken together with the carbon atom to which they are joined form a ring of 4 to 12 atoms; R³, R⁴, R⁹, and R¹⁰ are independently hydrogen or lower alkyl; R⁵ and R s independently are hydrogen or methyl; n¹ and n² independently are 0 or 1; X¹ and X² independently are selected from the group consisting of -CH₂ (when at least one of p¹ and p² =1); -CH(when at least one of p¹ and p² - 2); -C (when at least one of p¹ and p² = 3); -CR¹¹R¹² in which R¹¹ and R¹² are selected from the group consisting of alkyl, alkenyl, cycloalkyl, and aryl monovalent groups; a single bond; and polyvalent alkylene, alkenylene, cycloalkylene, or arylene linking groups; -CHR¹¹; -CR¹¹; -CW¹W² in which W¹ and W² are independently selected from R¹¹O₂C-, R¹¹(CO)-, N≡C-, R F (CO)- in which R F is a substantially perfluorinated alkyl, cycloalkyl, or aryl group, R¹¹NH(CO)-, R¹¹R¹²N(CO)-, R¹¹SO₂, R¹¹R¹²C=N-, R¹¹N=(R¹²)C-, R¹¹(CS)-, R¹¹S₂C-, R¹¹NH(CS)-, R¹¹R¹²N(CS)-, R¹¹R¹²C=CR¹³- in which R¹³ is defined the same as R¹¹ and R¹², and O₂N- groups; -CR¹¹W¹; -CHW¹; -CW¹; -NR¹⁴ in which R¹⁴ (linking at least one of X¹ to Y¹, X¹ to G, X¹ to X², X² to Y², and X² to G) is a single bond, alkylene, alkenylene, or arylene group such that the ring formed contains 4 to 6 ring atoms; and -NW¹; Z¹ and Z² independently are C, N, or S=O; Y¹ and Y² independently are doubly bonded oxygen (=O); doubly bonded sulfur (=S); =CR¹⁵R¹⁶, or -CR¹⁵ = CR¹⁶R¹⁷ in which R¹⁵ and R¹⁶ independently are defined the same as R¹¹, R¹², and R¹³, except that R¹⁵ can be an electron pair, and in which R¹⁷ is a monovalent group selected from alkyl, alkenyl, cycloalkyl, and aryl groups; =NR¹⁵ (to include triply bonded nitrogen (≡N:) when R¹⁵ is an electron pair and G is a single bond from at least one of Y¹ to Z¹ and Y² to Z²); or -NR¹⁸R¹⁹ in which R¹⁸ and R¹⁹ independently can be hydrogen, alkyl, cycloalkyl, aryl, a single bond, alkylene, cycloalkylene, or arylene, or together with the nitrogen atom to which they are joined form a ring of 4 to 12 ring atoms; G is -H; -NR²⁰R²¹ in which R²⁰ and R²¹ independently are defined the same as R¹¹, R¹², and R¹³; -NHR²⁰; -R²⁰; or -OR²⁰; =O; polymeric monovalent and polyvalent groups; an electron pair; or a single bond; and q is an integer 0 or greater and is equal to (the valence of G)-1.
Claim 2
Dependent Claim 21 words
The adduct according to claim 1 wherein G contains one or more of S, O, N, P, halogen, and Si atoms.
Claim 3
Dependent Claim 49 words
The adduct according to claims 1 and 2 wherein G includes at least one functional group selected from the group consisting of alkyl, alkenyl, aryl, amide, thioamide, ester, thioester, ketone, thioketone, nitrile, nitro, sulfide, sulfoxide, sulfone, disulfide, tertiary amine, ether, urethane, dithiocarbamate, quaternary ammonium, phosphonium, halogen, silyl, and silyloxy.
Claim 4
Dependent Claim 90 words
A process for preparing an azlactone-functional adduct according to claims 1 to 3 comprising the step of reacting at least one 2-alkenyl azlactone Michael acceptor of Formulae VIIa and VIIb: wherein R¹ , R² , R³ , R⁴ , R⁵ , R⁶ , R⁷ , R⁸ , R⁹ , R¹⁰ , n¹ , n² , p¹ , and p² are as defined in claim 1, with a Michael donor of Formula VIII wherein X¹, X², Y¹, Y², Z¹, Z², G, q, p¹ and p² are as defined in claim 1.
Claim 5
Dependent Claim 22 words
The process according to claim 4 wherein said alkenyl azlactone is selected from the group consisting of 2-vinyl-4,4-dimethyl-2-oxazolin-5-one, 2-isopropenyl-4,4-dimethyl-2-oxazolin-5-one, 2-vinyl-4-ethyl-4-methyl-2-oxazolin-5-one, and 2-vinyl-4,4-dimethyl-1,3-oxazin-6-one.
Claim 6
Dependent Claim 34 words
The process according to claims 4 and 5 wherein said Michael donor is selected from the group consisting of nitrogen nucleophiles whose conjugate acids have a pKa of at most 5 and carbon nucleophiles.
Claim 7
Dependent Claim 50 words
The process according to claims 4 to 6 wherein said carbon nucleophile is selected from the group consisting of carbon acids having a pKa of at most 15 or are suitably activated by having the carbon acidic function contained within a ring system of six atoms or less and enamines.
Claim 8
Dependent Claim 17 words
The process according to claims 4 to 7 further comprising a chemically effective amount of a catalyst.
Claim 9
Dependent Claim 22 words
The process according to claim 8 wherein said catalyst is selected from the group consisting of bicyclic amidines and trivalent phosphorus compounds.
Claim 10
Dependent Claim 31 words
The process according to claim 6 wherein said nitrogen nucleophile is selected from the group consisting of imidic compounds and nitrogen heterocycles having at least one electron withdrawing group on nitrogen.
Claim 11
Dependent Claim 26 words
The adduct according to claims 1 to 3 which is a precursor to an adhesive, a precursor to a sealant, or a precursor to a coating.

References Cited (Backward Citations)

GB1202119A Cited
EP0105665A1 Cited
EP0333361A2 Cited

USPTO Annuity & Maintenance Windows

Maintenance schedule is calculated for granted US utility patents.

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag