Bio-Oil Polyols, Alkoxylated Bio-Oil Polyols and Bio-Oil Phenolic Resins

Patent metadata

Field	Value
Publication number	US-2016145285-A1
Application number	US-201414897956-A
Country	US
Kind code	A1
Filing date	Jun 11, 2014
Priority date	Jun 11, 2013
Publication date	May 26, 2016
Grant date	—

Abstract

Methods are provided for producing bio-oil polyols, alkoxylating bio-oil polyols to provide polyols, and for employing the alkoxylated bio-oil polyols for making polymers or copolymers of polyesters or polyurethanes. Compositions and methods are provided for incorporating bio-oils into phenolic resins such as phenol-formaldehyde resin and phenol-formaldehyde-urea resin, as well as hot melt adhesive compositions.

First claim

1 - 157 . (canceled)

158 . A method for preparing an alkoxylated bio-oil polyol, the method comprising:
providing a bio-oil polyol; and reacting the bio-oil polyol in the presence of a catalyst under reaction conditions effective to form the alkoxylated bio-oil polyol with one or more of: a cyclic alkylene oxide; and a reagent polyol.

159 . The method of claim 1 , the cyclic alkylene oxide comprising one or more of:
unsubstituted ethylene oxide or ethylene oxide substituted with a linear or branched C 1 -C 6 alkyl group or a C 3 -C 6 cycloalkyl group; 1,2-propylene oxide; a weight % compared to a weight of the bio-oil polyol of between about 5 weight % and about 70 weight %; and a weight % compared to a weight of the bio-oil polyol of greater than 10 weight %.

160 . The method of claim 158 , the reaction conditions comprising one or more of:
a presence of a catalytic alkali metal hydroxide or a catalytic alkali earth metal hydroxide or oxide; a presence of a catalytic amount of potassium hydroxide; a presence of a catalyst in a weight % compared to a weight of the bio-oil polyol of between about 0.01 weight % and about 5 weight %; a temperature between about 80° C. and about 180° C.; a pressure in pounds per square inch of between about 0 and about 600; and a presence of an acidified lignin.

161 . The method of claim 158 ,
the bio-oil polyol comprising one or more of: a bio-oil; an intermediate bio-oil polyol comprising the bio-oil modified by reaction with the bio-oil; and the intermediate bio-oil polyol comprising the bio-oil modified by reaction with a reagent polyol; and the bio-oil comprising one or more of: the bio-oil produced by pyrolysis of biomass or a catalytic bio-oil produced by catalytic pyrolysis of biomass.

162 . The method of claim 161 , further comprising pyrolyzing biomass to provide the bio-oil or catalytically pyrolyzing the biomass to provide the bio-oil as a catalytic bio-oil.

163 . The method of claim 158 , further comprising reacting a bio-oil with at least one of the bio-oil or the reagent polyol in the presence of a polyol-forming catalyst to provide the bio-oil polyol.

164 . The method of claim 158 , the reagent polyol comprising one or more of glycerol, ethylene glycol, propylene glycol, 1,3-propanediol, 2-methyl-1,3-propanediol, pentaerythritol, a sugar alcohol, an alcohol amine, a polyalkylene glycol, an alkylene glycol, a polyethylene glycol, a polypropylene glycol, a poly(tetramethylene ether) glycol, acidified and demethylated crude glycerol, and wet crude glycerol from steam splitting.

165 . The method of claim 158 , the catalyst comprising tin.

166 . The method of claim 158 , the catalyst comprising tin (II) oxalate.

167 . A method for producing a polymer composition, the method comprising:
providing a polymerization precursor mixture configured to form a polymer in combination with an alkoxylated bio-oil polyol; and reacting the alkoxylated bio-oil polyol with the polymerization precursor mixture under reaction conditions effective to form the polymer composition.

168 . The method of claim 167 , the polymerization precursor mixture comprising a polyurethane precursor comprising one or more of toluene diisocyanate, methylene diphenyl diisocyanate, 1,6-hexamethylene diisocyanate, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl-cyclohexane, and 4,4′-diisocyanato dicyclohexylmethane.

169 . The method of claim 167 , the polymerization precursor mixture comprising one or more of: a petroleum polyol, water, a foam-forming surfactant, a trialkylamine, a polyamino alkane, a polyalkylamino alkyl ether, an antioxidant, a flame retardant, an ultraviolet light stabilizer, a pigment, a dye, and a plasticizer.

170 . The method of claim 167 , the polymerization precursor mixture comprising a polyfunctional ester precursor effective to form the polymer composition comprising a polyester, the polyfunctional ester precursor comprising one or more of: a polycarboxylic acid, a polyacyl halide, and a cyclic anhydride.

171 . The method of claim 167 , the reaction conditions comprising one or more of:
a presence of a catalyst for one or more of: polyester polymerization, polyurethane polymerization, and phenolic resin formation; a temperature between about 0° C. and about 180° C.; a pressure in pounds per square inch of between about 15 and about 600; and a presence of a viscosity-reducing modifier.

172 . The method of claim 167 , the polymerization precursor mixture comprising an aliphatic phenolic resin precursor and a phenolic resin catalyst effective to produce the polymer composition comprising a phenolic resin.

173 . The method of claim 167 , the aliphatic phenolic resin precursor comprising one or more of: a reactive carbonyl compound, a reactive carbonyl compound that is at least partly water soluble, a urea derivative, a formaldehyde-urea resin, formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, glyoxal, propane-1,3-dial, butane-1,4-dial, glutaraldehyde, acetone, 2-butanone, 2-pentanone, 3-pentanone, butane-2,3-dione, and pentane-2,4-dione.

174 . The method of claim 167 , further comprising configuring the polymer composition as one or more of: a foam, a spray foam, an extrusion, an injection molding, a coating, an adhesive, an elastomer, a foundry resin, a sealant, a casting, a fiber, a potting compound, a reaction injection molded (RIM) plastic, a microcellular elastomer or foam, or an integral skin foam.

175 . A polymer composition, produced by a process comprising:
providing a polymerization precursor mixture configured to form a polymer in combination with an alkoxylated bio-oil polyol; and reacting the alkoxylated bio-oil polyol with the polymerization precursor mixture under reaction conditions effective to form the polymer composition.

176 . The polymer composition of claim 175 , comprising one or more of: a polyurethane, a polyester, and a phenolic resin.

177 . The polymer composition of claim 175 , configured as one or more of: a foam, a spray foam, an extrusion, an injection molding, a coating, an adhesive, an elastomer, a foundry resin, a sealant, a casting, a fiber, a potting compound, a reaction injection molded (RIM) plastic, a microcellular elastomer or foam, and an integral skin foam.

Assignees

• Battelle Memorial Institute

Inventors

• Garbark Daniel B
• Benecke Herman P
• Moore Megan S
• Perry Mark J
• Cafmeyer Jeffrey T

Classifications

• C08G65/2603 Primary

  the other compounds containing oxygen · CPC title

• C08G18/14

  Manufacture of cellular products · CPC title

• C08G8/20

  with polyhydric phenols · CPC title

• C07G1/00 Primary

  Low-molecular-weight derivatives of lignin (high-molecular-weight derivatives of lignin {C08H6/00}) · CPC title

• C09J167/04

  Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C09J167/06 takes precedence) · CPC title