Ketal Compounds from Polyols and Oxocarboxylates
AssigneeSegetis, Inc.
InventorsDouglas Alan Wicks, Charles Todd Williams, Sergey A. Selifonov
Life of this patent
Estimating the term…
Abstract
Novel ketal compounds can be made from an oxocarboxylate and a triol. Novel polymeric structures are, in turn, synthesized from the ketal compounds. Such ketal compounds and associated polymers are useful in a broad range of applications as a substitute for materials derived from petroleum or other such nonrenewable resources.
Claims36
A polyester having a structure corresponding to (1):
- wherein
- R1 and R2 are ester residues and can be hydrogen or a carboxyl atom of a keto acid fragment, and wherein R2 is hydroxyl, an oxygen atom of a triol, or an oxygen atom of an esterified triol fragment,
- p is an integer of at least 2,
- a is 0 or 1,
- b is 0 or 1,
- R3 is methyl;
- and
- R4 is hydrogen, methyl, or ethyl.
A dihydroxy functional material comprising structures (2), (3), or a mixture thereof:
- wherein
- a equals 0 or 1;
- b equals 0 or 1;
- R2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;
- R3 methyl;
- and
- R4 is hydrogen, methyl, or ethyl.
A polyhydroxy functional compound having a structure corresponding to (4):
- wherein:
- a equals 0 or 1;
- b equals 0 or 1;
- R2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;
- R3 is methyl;
- R4 is hydrogen, methyl, or ethyl;
- α is an integer of about 1 to 100;
- and
- β is an integer of at least 2.
An isocyanate functional prepolymer having a structure corresponding to (5):
- wherein
- a equals 0 or 1;
- b equals 0 or 1;
- R2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;
- R3 is methyl;
- R4 is hydrogen, methyl, or ethyl;
- R5 is the residue of an organic diisocyanate having a molecular weight of about 100 to 1,000 g/mol;
- α is an integer of about 1 to 100;
- and
- β is an integer of at least 2.
A copolyester having a structure corresponding to (6)):
- wherein
- a equals 0 or 1;
- b equals 0 or 1;
- R2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;
- R3 is methyl;
- R4 is hydrogen, methyl, or ethyl;
- R5 is the residue of an organic diacid having a molecular weight of about 100 to 1,000 g/mol;
- α is an integer of about 1 to 100;
- and
- x, y and z represent molar fractions of the indicated residue in the copolymer, such that the sum of (x+y+z) equals 1.
A polyester having a structure corresponding to (7):
- wherein
- R1 and R2 are ester residues and can be hydrogen or a carboxyl atom of a keto acid fragment, and wherein R2 is hydroxyl, an oxygen atom of a triol, or an oxygen atom of an esterified triol fragment,
- p is an integer of at least 2,
- R3 is methyl;
- and
- R4 is hydrogen, methyl, or ethyl.
A dihydroxy functional material comprising structures (8), (9), or a mixture thereof:
- wherein
- R2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;
- R3 methyl;
- and
- R4 is hydrogen, methyl, or ethyl.
A polyhydroxy functional compound having a structure corresponding to (10):
- wherein:
- R2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;
- R3 is methyl;
- R4 is hydrogen, methyl, or ethyl;
- α is an integer of about 1 to 100;
- and
- β is an integer of at least 2.
An isocyanate functional prepolymer having a structure corresponding to (11):
- wherein
- R2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;
- R3 is methyl;
- R4 is hydrogen, methyl, or ethyl;
- R5 is the residue of an organic diisocyanate having a molecular weight of about 100 to 1,000 g/mol;
- α is an integer of about 1 to 100;
- and
- β is an integer of at least 2.
A copolyester having a structure corresponding to (12):
- wherein
- R2 represents an alkylene, cycloallylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;
- R3 is methyl;
- R4 is hydrogen, methyl, or ethyl;
- R5 is the residue of an organic diacid having a molecular weight of about 100 to 1,000 g/mol;
- α is an integer of about 1 to 100;
- and
- x, y and z represent molar fractions of the indicated residue in the copolymer, such that the sum of (x+y+z) equals 1.
Dependencies are inferred from the claim text.