US 6,646,153 B1Granted

Hydroxyl functional urethanes having a tertiary carbamate bond

AssigneeE. I. Du Pont de Nemours and Company

InventorJosef Huybrechts

Life of this patent

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Abstract

Hydroxy functional urethane compounds comprising the reaction product of a hydroxy functional urethane intermediate with a compound having at least 2 isocyanate groups, wherein the intermediate is represented by the formula: wherein R1 and R2=hydrogen, alkyl, cycloalkyl or a residue R6—O— or R6—CO—O— with R6; R6=an alkyl, cycloalkyl or benzylic group having up to 18 carbon atoms; R4 and R5=hydrogen or alkyl group containing eventually a hydroxyl group; and R3=alkyl, cycloalkyl or benzylic group eventually containing an ether linkage and/or a hydroxyl group, or HO—CH(R1)—CH(R2)—; and is prepared by reaction of a cyclic 5-ring carbonate with a beta-hydroxy functional, secondary amine. The hydroxy functional urethanes are useful in paints and coatings, particularly for automotive applications.

Claims7

Dependent claims

A hydroxy functional urethane compound comprising the reaction product of:

a) a hydroxy functional urethane intermediate containing a tertiary carbamate group prepared by reaction of a cyclic 5-ring carbonate with a beta-hydroxy functional, secondary amine, said intermediate represented by the formula:
wherein
R1 and R2=hydrogen, an alkyl of 1-4 carbon atoms, cycloalkyl or R6—O—, R6—CO—O— or R6 optionally substituted with R6—O— or R6—CO—O—;
R6=an alkyl, cycloalkyl or benzylic group having up to 18 carbon atoms;
R4 and R5=hydrogen or alkyl group optionally containing a hydroxyl group;
and
R3=alkyl, cycloalkyl or benzylic group optionally containing an ether linkage and/or a hydroxyl group, or HO—CH(R1)—CH(R2)—;
with
b) a compound having at least 2 isocyanate groups;
wherein said hydroxy functional urethane intermediate of a) and said compound having at least 2 isocyanate groups of b) has an OH:NCO ratio ranging from 2:1 to 4:1:
and
further wherein the hydroxy functional urethane compound produced is free from isocyanate groups.

9 more elements

A coating composition comprising a hydroxy functional urethane compound comprising the reaction product of:

a) a hydroxy functional urethane intermediate containing a tertiary carbamate group prepared by reaction of a cyclic 5-ring carbonate with a beta-hydroxy functional, secondary amine, said intermediate represented by the formula:
wherein
R1 and R2=hydrogen, an alkyl of 1-4 carbon atoms, cycloalkyl or R6—O—, R6—CO—O— or R6 optionally substituted with R6—O— or R6—CO—O—;
R6=an alkyl, cycloalkyl or benzylic group having up to 18 carbon atoms;
R4 and R5=hydrogen or alkyl group optionally containing a hydroxyl group;
and
R3=alkyl, cycloalkyl or benzylic group optionally containing an ether linkage and/or a hydroxyl group, or HO—CH(R1)—CH(R2)—;
with
b) a compound with at least 2 isocyanate groups;
wherein said hydroxy functional urethane intermediate of a) and said compound having at least 2 isocyanate groups of b) has an OH:NCO ratio ranging from 2:1 to 4:1:
and
further wherein the hydroxy functional urethane compound produced is free from isocyanate groups.

9 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/619,320Filed 19 Jul 2000
Granted: 11 Nov 2003
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

C09D 175/04
Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers: polyurethanes
C07C 271/16
With the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms: to carbon atoms of hydrocarbon radicals…
C08G 18/10
Processes: prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
C08G 18/3831
Containing -N-C=O groups: containing urethane groups