Triazabutadienes as additives in adhesive systems
AssigneeArizona Board of Regents on Behalf of the University of Arizona
InventorsJohn C. Jewett, Flora W. Kimani
Life of this patent
Estimating the term…
Abstract
Triazabutadiene molecules that provide adhesive functionality, e.g., triazabutadiene molecules as underwater adhesives or water-reactive adhesives. The triazabutadiene molecules mask an aryl diazonium ion, a highly reactive chemical functionality. Once unmasked, e.g., in water, the diazonium species is adapted to react with an electron rich aryl ring that can undergo diazonium chemistry (e.g., phenol species, resorcinol species, etc.). Triazabutadienes can be used as additives in adhesive systems such as but not limited to epoxy adhesive systems.
Claims13
A triazabutadiene molecule according to formula 1,
- wherein
- A=S, O, or N;
- D=H, —CH═CH—CH=E-, halides, cyano, sulfonates, alkyl chain, or trifluoromethyl;
- E=H, —CH═CH—CH=D-, halides, cyano, sulfonates, alkyl chain, or trifluoromethyl;
- Xl=—R1-Q1;
- wherein —R1=alkanes and Q1=sulfonate, phosphate, or a quaternary ammonium cation, or an alkyl, aryl or propargylic containing moiety that can facilitate coupling to other azides via [3+2]cycloaddition chemistry;
- Yl=tri-substituted aryl group or alkyl substituents;
- and
- Zl=polymerization residue.
A formulation comprising a triazabutadiene molecule and an epoxide resin, the triazabutadiene molecule comprises:
- wherein
- A=S, O, or N;
- D=H, —CH═CH—CH=E-, halides, cyano, sulfonates, alkyl chain, or trifluoromethyl;
- E=H, —CH═CH—CH=D-, halides, cyano, sulfonates, alkyl chain, or trifluoromethyl;
- Xl=—R1-Q1;
- wherein —R1=alkanes and Q1=sulfonate, phosphate, or a quaternary ammonium cation, or an alkyl, aryl or propargylic containing moiety that can facilitate coupling to other azides via [3+2]cycloaddition chemistry;
- Yl=tri-substituted aryl group or alkyl substituents;
- and
- Zl=polymerization residue.
A method of producing an adhesive, the method comprises:
- a) providing a composition A which comprises:
- or
- wherein
- A=S, O, or N;
- D=H, —CH═CH—CH=E-, halides, cyano, sulfonates, alkyl chain, or trifluoromethyl;
- E=H, —CH═CH—CH=D-, halides, cyano, sulfonates, alkyl chain, or trifluoromethyl;
- Xl=—R1-Q1;
- wherein —R1=alkanes and Q1=sulfonate, phosphate, or a quaternary ammonium cation, or an alkyl, aryl or propargylic containing moiety that can facilitate coupling to other azides via [3+2]cycloaddition chemistry;
- Yl=tri-substituted aryl group or alkyl substituents;
- and
- n=1-10;
- b) providing a composition B which comprises:
- or
- wherein m=1-5;
- and
- c) mixing composition A and composition B to form a product C, product C being the adhesive, product C comprises:
- wherein
- A=S, O, or N;
- D=H, —CH═CH—CH=E-, halides, cyano, sulfonates, alkyl chain, or trifluoromethyl;
- E=H, —CH═CH—CH=D-, halides, cyano, sulfonates, alkyl chain, or trifluoromethyl;
- Xl=—R1-Q1;
- wherein —R1=alkanes and Q1=sulfonate, phosphate, or a quaternary ammonium cation, or an alkyl, aryl or propargylic containing moiety that can facilitate coupling to other azides via [3+2]cycloaddition chemistry;
- Yl=tri-substituted aryl group or alkyl substituents;
- m=1-5;
- and
- n=1-10.
Dependencies are inferred from the claim text.