Water based lignin epoxy resins, methods of using and making the same
View Patent ↗Water based lignoepoxy resins, and methods for their preparation and use are provided. Methods of making lignoepoxy resins without the use of volatile organic compounds are also provided.
1. A method of making a lignomethylol or a lignosulphonate methylol, the method comprising contacting a lignin or a lignosulphonate with formaldehyde or paraformaldehyde or glyoxal under conditions sufficient to produce the lignomethylol or the lignosulphonate methylol, wherein
the lignomethylol has a formula of:
2. The method of claim 1 , further comprising epoxidizing the lignomethylol or the lignosulphonate methylol under basic pH conditions to produce a lignomethylol epoxy or a lignosulphonate methylol epoxy.
3. The method of claim 1 , further comprising contacting the lignomethylol or the lignosulphonate methylol with ammonia or an amino compound to produce a water soluble aminolignin derivative.
4. The method of claim 3 , wherein the aminolignin derivative has a formula of Formula I,
wherein each R 1 is independently selected from the group consisting of NH 2 , —NHCH 2 CH 2 NH 2 , diethylenetriamine, triethylenetetraamine, tetraethylenepentaamine, hydroxylamine, hydrazine, monoethanoloamine, diethanolamine, and triethanolamine.
5. The method of claim 3 , wherein the amino compound is a monoethanolamine, a monoalkylamine, dialkylamine, trialkyl amine, ethylene diamine, diethylenetriamine, tetraethylene pentamine, mono ethanol amine, diethanolamine, triethanolamine, isophorone diamine, hydroxylamine, or hydrazine.
6. The method of claim 3 , further comprising drying the water soluble aminolignin derivative.
7. The method of claim 3 , further comprising contacting the amino lignin with ethanolamine, a hydroxycarboxylic acid salt, a polyhydroxycarboxylic acid, an isocyanate terminated polyalkylene oxide, an epichlorohydrine, a hydroxycarboxylic acid salt, or a polyhydroxylic acid salt to produce a surfactant.
8. The method of claim 3 , further comprising contacting the aminolignin with epichlorohydrine at a temperature of about 0-10° C. to produce a ligno aminoepoxy resin.
9. The method of claim 8 , wherein the ligno aminoepoxy resin has a formula of:
10. The method of claim 8 , further comprising contacting the ligno amino resin with phosgene, carbon monoxide, or carbon dioxide to produce a lignoisocyanate derivatives.
11. The method of claim 1 , wherein the method does not comprise a volatile organic compound.
12. A method of curing an ligno amino epoxy resin, the method comprising contacting a ligno aminoepoxyresin with a water soluble aminolignin according to their epoxy equivalent weight for a sufficient time at room temperature until the resin is cured.
13. A composition comprising a compound having a formula of
wherein each R 1 is independently selected from the group consisting of NH 2 , NH 2 CH 2 CH 2 NH 2 , diethylenetriamine, triethylenetetraamine, tetraethylenepentaamine, hydroxylamine, hydrazine, monoethanoloamine, diethanolamine, and triethanolamine.
14. The composition of claim 13 , wherein the compound has a formula of
15. The composition of claim 13 , wherein the compound has a formula of Formula I,
wherein each R 1 is independently selected from the group consisting of NH 2 , NH 2 CH 2 CH 2 NH 2 , diethylenetriamine, triethylenetetraamine, tetraethylenepentaamine, hydroxylamine, hydrazine, monoethanoloamine, diethanolamine, and triethanolamine.
16. The composition of claim 13 , wherein the composition compound has a formula of
wherein R 1 is independently selected from the group consisting of NH 2 , NH 2 CH 2 CH 2 NH 2 , diethylenetriamine, triethylenetetraamine, tetraethylenepentaamine, hydroxylamine, hydrazine, monoethanoloamine, diethanolamine, and triethanolamine.
17. The method of claim 12 , wherein the ligno aminoepoxyresin has a formula of: