Polymer polyols and polymer dispersions made from vegetable oil-based hydroxyl-containing materials
View Patent ↗Polymer polyols and dispersions are prepared by polymerizing certain starting materials in a continuous phase. The continuous phase includes a polyol containing hydroxylmethyl groups, which is derived from a fatty acid. The dispersed phase may be, for example, a vinyl polymer, a polyurea or a polyurethane-urea.
1. A polymer polyol having a polyol continuous phase and dispersed polymer particles, wherein the polyol continuous phase includes at least one hydroxymethyl-containing polyester polyol derived from a fatty acid or ester of a fatty acid, wherein the dispersed polymer particles comprises polyurea polymer particles or polyurethane-urea particles formed in the presence of the at least one hydroxymethyl-containing polyester polyol derived from a fatty acid or ester of a fatty acid, and wherein the hydroxymethyl group-containing polyester polyol has the following structure:
[H—X] z-p) —R—[X—Z] p (I)
wherein R is the residue of an initiator compound having z hydroxyl and/or primary or secondary amine groups, where z is at least two; each X is independently —O—, —NH— or —NR′— in which R′ is an inertly substitute alkyl, aryl, cycloalkyl, or aralkyl group, p is a number from 1 to z representing the average number of [X—Z] groups per hydroxymethyl-containing polyester polyol molecule, Z is a linear or branched chain containing one or more A groups, provided that the average number of A groups per molecule is >=1.3 times z, and each A is independently selected from the group consisting of A1, A2, A3, A4 and A5, provided that at least some A groups are A1, A2 and A3, and provided that A1 has a molar ratio of between about 30 and about 80 mole-% of the total mole-% of A1+A2+A3, A2 has a molar ratio of between about 10 and about 60 mole-% of the total mole-% of A1+A2+A3, A3 has a molar ratio of between about 0.1 and about 10 mole-% of the total mole-% of A1+A2+A3, wherein A1 is:
wherein B is H or a covalent bond to a carbonyl carbon atom of another A group; m is number greater than 3, n is greater than or equal to zero and m+n is from 11 to 19; A2 is:
wherein B is as before, v is a number greater than 3, r and s are each numbers greater than or equal to zero with v+r+s being from 10 to 18, A3 is:
wherein B, v, each r and s are as defined before, t is a number greater than or equal to zero, and the sum of v, r, s and t is from 10 to 18; A4 is
where w is from 10-24, and A5 is
where R′ is a linear or branched alkyl group that is substitute with at least one cyclic ether group and optionally one or more hydroxyl groups or other ether groups.
2. The polymer polyol of claim 1 , wherein the hydroxymethyl-containing polyester polyol is prepared by reacting a hydroxymethyl group-containing fatty acid having from 12 to 26 carbon atoms, or an ester of such a hydroxymethyl group-containing fatty acid, with a polyol or polyamine initiator compound having an average of at least 2 hydroxyl, primary amine and/or secondary amine groups, such that the hydroxymethyl-containing polyester polyol contains an average of at least 1.3 repeating units derived from the hydroxymethyl-group-containing fatty acid or ester per total number of hydroxyl, primary amine and secondary amine groups in the initiator compound, and the hydroxymethyl-containing polyester polyol has an equivalent weight of at least 400 up to 15,000.
3. The polymer polyol of claim 1 or 2 , wherein the equivalent weight of the hydroxymethyl-containing polyester polyol is from 700 to 3500.
4. The polymer polyol of claim 1 , wherein the hydroxymethyl-containing polyester polyol contains an average of 2 to 5 hydroxyl, primary amine or secondary amine groups per molecule.
5. The polymer polyol of claim 1 , wherein the hydroxymethyl group-containing polyester polyol has an average of from 3 to 4 hydroxyl groups per molecule and an equivalent weight per hydroxyl group of from 500 to 1000.
6. The polymer polyol of claim 1 , wherein the hydroxymethyl group-containing polyester polyol constitutes from 50 to 100% by weight of the polyol continuous phase.
7. A polyurethane polymer made by reacting the polymer polyol of claim 1 with a polyisocyanate.
8. The polyurethane polymer of claim 7 , which is cellular.
9. The polyurethane polymer of claim 7 , which is a slabstock flexible foam.
10. The polyurethane polymer of claim 9 , which is a molded flexible foam.