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US 6,204,381 B1Granted
Process for the preparation of triazine carbamates
AssigneeCytec Technology Corp.
InventorHong Zhao
Life of this patent
Estimating the term…
Abstract
Disclosed is the preparation of 1,3,5-triazine carbamates which are suitable for use as crosslinking agents in curable compositions, particularly in coating compositions which are capable of curing at relatively low temperatures without releasing formaldehyde during cure. The process includes the step of contacting a 1,3,5-triazine derivative having cyanate-displaceable leaving groups (i.e. cyanuric chloride), a cyanate-containing reagent (i.e. potassium cyanate), and an isocyanate-reactive compound such as an alcohol, in the presence of a polar solvent or in the presence of a non-polar solvent in combination with a phase transfer catalyst.
Claims33
A process for preparing a 1,3,5-triazine carbamate derivative having the formula (I):
- wherein R is selected from the group consisting of—NHCOOR3, hydrogen, hydrocarbyl, hydrocarbyloxy, hydrocarbylthio, amido, sulfonamido, and a leaving group;
- and
- wherein R1, R2 or R3 is, independently, a hydrocarbyl or a hydrocarbyloxyhydrocarbyl,
- said process comprising the steps of contacting:
- (i) a 1,3,5-triazine derivative having at least two cyanate-displaceable leaving groups, represented by the formula (II):
- wherein L1 is selected from the group consisting of hydrogen, hydrocarbyl, hydrocarbyloxy, hydrocarbylthio, amido, sulfonamido, amino and a leaving group;
- and
- wherein each of L2 and L3 is, independently, a leaving group;
- wherein said leaving group is selected from the group consisting of halogen, a tertiary amino group and a sulfonate group;
- (ii) a cyanate-group containing reagent capable of reaction therewith;
- (iii) an isocyanate-reactive compound;
- and
- (iv) an isocyanate-unreactive organic solvent,
- wherein said contacting is carried out at a temperature and length of time sufficient to produce a 1,3,5-triazine carbamate derivative having at least two carbamate groups, with the proviso that if the organic solvent is not sufficiently polar to produce a bis-carbamate derivative, contacting is carried out in the presence of a phase-transfer catalyst.
11 more elements
A process for preparing a 1,3,5-triazine carbamate derivative having the formula (I):
- wherein R is selected from the group consisting of —NHCOOR3, hydrogen, hydrocarbyl, hydrocarbyloxy, hydrocarbylthio, amido, sulfonamido, and a leaving group;
- and
- wherein R1, R2 or R3 is, independently, a hydrocarbyl or a hydrocarbyloxyhydrocarbyl,
- said process comprising the steps of contacting:
- (i) a 1,3,5-triazine derivative having at least two cyanate-displaceable leaving groups, represented by the formula (II):
- wherein L1 is selected from the group consisting of hydrogen, hydrocarbyl, hydrocarbyloxy, hydrocarbylthio, amido, sulfonamido, amino and a leaving group;
- and
- wherein each of L2 and L3 is, independently, a leaving group;
- wherein said leaving group is selected from the group consisting of halogen, a tertiary amino group and a sulfonate group;
- (ii) a cyanate-group containing reagent capable of reaction therewith;
- (iii) a hydroxy-functional compound;
- and
- (iv) an isocyanate-unreactive polar organic solvent,
- wherein said contacting is carried out at a temperature and length of time sufficient to produce a 1,3,5-triazine carbamate derivative having at least two carbamate groups.
11 more elements
A process for preparing a 1,3,5-triazine carbamate derivative having the formula (I):
- wherein R is selected from the group consisting of —NHCOOR3, hydrogen, hydrocarbyl, hydrocarbyloxy, hydrocarbylthio, amido, sulfonamido, and leaving group;
- and
- wherein R1, R2 or R3 is, independently, a hydrocarbyl or a hydrocarbyloxyhydrocarbyl,
- said process comprising the steps of contacting:
- (i) a 1,3,5-triazine derivative having at least two cyanate-displaceable leaving groups, represented by the formula (II):
- wherein L1 is selected from the group consisting of hydrogen, hydrocarbyl, hydrocarbyloxy, hydrocarbylthio, amido, sulfonamido, amino and a leaving group;
- and
- wherein each of L2 and L3 is, independently, a leaving group;
- wherein said leaving group is selected from the group consisting of halogen, a tertiary amino group and a sulfonate group;
- (ii) a cyanate-group containing reagent capable of reaction therewith;
- (iii) a hydroxy-functional compound;
- (iv) an isocyanate-unreactive non-polar organic solvent;
- and
- (v) a phase-transfer catalyst;
- wherein said contacting is carried out at a temperature and length of time sufficient to produce a 1,3,5-triazine carbamate derivative having at least two carbamate groups.
12 more elements
A process for preparing a 1,3,5-triazine carbamate derivative having at least two carbamate groups, represented by the formula (I):
- wherein R is selected from the group consisting of —NHCOOR3, hydrogen, hydrocarbyl, hydrocarbyloxy, hydrocarbylthio, amido, sulfonamido, and a leaving group;
- and
- wherein R1, R2 or R3 is, independently, a hydrocarbyl or a hydrocarbyloxyhydrocarbyl,
- said process comprising the steps of contacting:
- (i) a 1,3,5-triazine derivative having at least two cyanate-displaceable leaving groups, represented by the formula (II):
- wherein L1 is selected from the group consisting of hydrogen, hydrocarbyl, hydrocarbyloxy, hydrocarbylthio, amido, sulfonamido, amino and a leaving group;
- and
- wherein each of L2 and L3 is, independently, a leaving group;
- wherein said leaving group is selected from the group consisting of halogen, a tertiary amino group and a sulfonate group;
- (ii) a cyanate-group containing reagent capable of reaction therewith;
- (iii) a hydroxy-functional compound;
- and
- (iv) an isocyanate-unreactive organic solvent,
- wherein said contacting is carried out at a temperature in the range of from about 25° C. to about 160° C. and length of time in the range of from about 1 hour to about 24 hours, with the proviso that if the organic solvent has a dipole moment of less than 3.0 Deby Units, contacting is carried out in the presence of a phase-transfer catalyst.
11 more elements
Dependencies are inferred from the claim text.