High recycle content polyols from thermoplastic polyesters and lignin or tannin

A process for making a polyester polyol, comprising:

• (a) heating a thermoplastic polyester with a glycol to give a digested intermediate;
• and
• (b) reacting the intermediate with a lignin, a tannin, or a mixture thereof to give the polyol;
• wherein the molar ratio of glycol to thermoplastic polyester recurring units is at least 0.8, the amount of lignin, tannin, or mixture thereof incorporated into the polyol is within the range of 0.1 to 35 wt. %, and the polyol has a hydroxyl number within the range of 25 to 800 mg KOH/g.

A process for making a polyester polyol, comprising:

• reacting a thermoplastic polyester;
• a glycol;
• a lignin, a tannin, or a mixture of lignin and tannin;
• and an optional hydrophobe to produce the polyol;
• wherein the molar ratio of glycol to thermoplastic polyester recurring units is at least 0.8, the amount of lignin, tannin, or mixture of lignin and tannin incorporated into the polyol is within the range of 0.1 to 35 wt. %, and the polyol has a hydroxyl number within the range of 25 to 800 mg KOH/g.

A process for making a polyester polyol, comprising:

• (a) heating an aromatic polyacid source with a glycol to give a digested intermediate;
• and
• (b) reacting the intermediate with a lignin, tannin, or mixture thereof and a hydrophobe selected from the group consisting of dimer fatty acids, oleic acid, ricinoleic acid, tung oil, corn oil, canola oil, soybean oil, sunflower oil, triglycerides having saturated C6-C36 fatty acid units, triglycerides having unsaturated C6-C36 fatty acid units, alkyl carboxylate esters having saturated C6-C36 fatty acid units, alkyl carboxylate esters having unsaturated C6-C36 fatty acid units, castor oil, alkoxylated castor oil, saturated C6-C18 dicarboxylic acids, unsaturated C6-C18 dicarboxylic acids, cardanol-based products, recycled cooking oil, branched C6-C36 fatty alcohols, linear C6-C36 fatty alcohols, hydroxy-functional materials derived from epoxidized fatty esters fatty acids, hydroxy-functional materials derived from ozonized fatty esters, hydroxy-functional materials derived from hydroformylated fatty esters, hydroxy-functional materials derived from epoxidized fatty acids, hydroxy-functional materials derived from ozonized fatty acids, hydroxy-functional materials derived from hydroformylated fatty acids, and mixtures thereof;
• wherein the molar ratio of glycol to aromatic polyacid source recurring units is at least 0.8, the amount of lignin, tannin, or mixture thereof incorporated into the polyol is within the range of 0.1 to 35 wt. %, and the polyol has a hydroxyl number within the range of 25 to 800 mg KOH/g.

A polyurethane or polyurethane/polyisocyanurate made from a polyester polyol, the polyol comprising recurring units from:

• (a) a digested thermoplastic polyester;
• (b) a glycol;
• (c) a lignin, a tannin, or a mixture thereof;
• and
• (d) optionally, a hydrophobe;
• wherein the molar ratio of glycol to thermoplastic polyester recurring units is at least 0.8, the amount of lignin, tannin, or mixture thereof incorporated into the polyol is within the range of 0.1 to 35 wt. %, and the polyol has a hydroxyl number within the range of 25 to 800 mg KOH/g.

An aqueous polyurethane dispersion made from a polyester polyol, the polyol comprising recurring units from:

• (a) a digested thermoplastic polyester;
• (b) a glycol;
• (c) a lignin, a tannin, or a mixture thereof;
• and
• (d) optionally, a hydrophobe;
• wherein the molar ratio of glycol to thermoplastic polyester recurring units is at least 0.8, the amount of lignin, tannin, or mixture thereof incorporated into the polyol is within the range of 0.1 to 35 wt. %, and the polyol has a hydroxyl number within the range of 25 to 800 mg KOH/g.

A two-component polyurethane coating made from a polyester polyol, the polyol comprising recurring units from:

• (a) a digested thermoplastic polyester;
• (b) a glycol;
• (c) a lignin, a tannin, or a mixture thereof;
• and
• (d) optionally, a hydrophobe;
• wherein the molar ratio of glycol to thermoplastic polyester recurring units is at least 0.8, the amount of lignin, tannin, or mixture thereof incorporated into the polyol is within the range of 0.1 to 35 wt. %, and the polyol has a hydroxyl number within the range of 25 to 800 mg KOH/g.

A curable resin comprising a reaction product of an acrylate or methacrylate source and a polyester polyol, the polyol comprising recurring units from:

• (a) a digested thermoplastic polyester;
• (b) a glycol;
• (c) a lignin, a tannin, or a mixture thereof;
• and
• (d) optionally, a hydrophobe;
• wherein the molar ratio of glycol to thermoplastic polyester recurring units is at least 0.8, the amount of lignin, tannin, or mixture thereof incorporated into the polyol is within the range of 0.1 to 35 wt. %, and the polyol has a hydroxyl number within the range of 25 to 800 mg KOH/g.