IP Library Granted Patent US 9,458,097
Granted Patent B2
US 9,458,097 · App. 14/509,202 · Granted Oct 4, 2016

Process for the preparation of polyisocyanates and use thereof

Inventors: Frank Richter (Leverkusen, DE); Martin Brahm (Odenthal, DE)
Assignee: Covestro Deutschland AG
C07C263/16C07F9/5435C08G18/022C08G18/168
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Quick Facts
Patent No.
US 9,458,097
App. No.
14/509,202
Granted
Oct 4, 2016
Kind
B2
Abstract

The invention relates to a process for isocyanate modification which includes reacting a) at least one organic isocyanate having an NCO functionality greater than or equal to 1, b) a catalyst comprising at least one phosphonium salt comprising at least one cycloalkyl substituent bonded directly to a P atom of a phosphonium cation, c) optionally a solvent, and d) optionally additives. The present invention also relates to a catalyst for isocyanate modification comprising at least one phosphonium salt comprising at least one cycloalkyl substituent bonded directly to a P atom of a phosphonium cation.

Claims (24)

1. A process which comprises reacting

a) at least one organic isocyanate having an NCO functionality greater than or equal to 1,

b) a catalyst comprising at least one phosphonium salt comprising at least one cycloalkyl substituent bonded directly to a P atom of a phosphonium cation,

c) optionally a solvent, and

d) optionally additives,

wherein the phosphonium salt comprises a cation corresponding to the formula I:

wherein R 1 to R 4 independently of one another represent organic radicals selected from the group consisting of C 1 - to C 20 -alkyl which is optionally branched, cyclopentyl, and cyclohexyl which is optionally substituted, and wherein at least two of the radicals R 1 to R 4 represent an optionally substituted cyclopentyl, cyclohexyl radical, or combinations thereof which are each bonded directly to the P atom via a ring carbon atom,

and wherein the phosphonium cation of the formula (I) has a counter-ion X − wherein X − is selected from the group consisting of di- and poly-(hydrogen) fluoride ([F − ×(HF) m ], wherein m represents whole or fractional numbers from 0.001 to 20.

2. The process according to claim 1 , wherein the at least one organic isocyanate is selected from the group consisting of aliphatic di- or poly-isocyanates, cycloaliphatic di- or poly-isocyanates, araliphatic di- or poly-isocyanates, and mixtures thereof, and wherein the at least one organic isocyanate has a functionality greater than or equal to 2.

3. The process according to claim 1 , wherein the reaction is carried out at a temperature from 0 to 250° C.

4. The process according to any claim 1 , further comprising terminating the reaction when from 5 to 80% of the at least one organic isocyanate has been converted.

5. The process according to claim 1 , further comprising separating the unconverted isocyanates from the reaction mixture.

6. A isocyanate produced by a process comprising reacting

a) at least one organic isocyanate having an NCO functionality greater than or equal to 1,

b) a catalyst comprising at least one phosphonium salt comprising at least one cycloalkyl substituent bonded directly to a P atom of a phosphonium cation,

c) optionally a solvent, and

d) optionally additive,

wherein the phosphonium salt comprises a cation corresponding to the formula I:

wherein R 1 to R 4 independently of one another represent organic radicals selected from the group consisting of C 1 - to C 20 -alkyl which is optionally branched, cyclopentyl, and cyclohexyl which is optionally substituted, and wherein at least two of the radicals R 1 to R 4 represent an optionally substituted cyclopentyl, cyclohexyl radical, or combinations thereof which are each bonded directly to the P atom via a ring carbon atom,

wherein the phosphonium cation of the formula (I) has a counter-ion X − wherein X − is selected from the group consisting of di- and poly-(hydrogen) fluoride ([F − ×(HF) m ], wherein m represents whole or fractional numbers from 0.001 to 20.

7. The isocyanate according to claim 6 , wherein the at least one organic isocyanate is selected from the group consisting of aliphatic di- or poly-isocyanates, cycloaliphatic di- or poly-isocyanates, araliphatic di- or poly-isocyanates, and mixtures thereof, and wherein the at least one organic isocyanate has a functionality greater than or equal to 2.

8. The isocyanate according to claim 6 , wherein the reaction is carried out at a temperature from 0 to 250° C.

9. The isocyanate according to claim 6 , further comprising terminating the reaction when from 5 to 80% of the at least one organic isocyanate has been converted.

10. The isocyanate according to claim 6 , further comprising separating the unconverted isocyanates from the reaction mixture.

Assignments (2)
CHANGE OF NAME Recorded Aug 3, 2017
From: BAYER MATERIALSCIENCE AG
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 043428/0238 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 12, 2017
From: RICHTER, FRANK; BRAHM, MARTIN
To: BAYER MATERIALSCIENCE AG
Reel/Frame 042989/0478 →
Priority Claims (1)
DE 10 2010 038 845 · Aug 3, 2010 · national
Continuity (2)
Division 13193189 · Jul 28, 2011
Related Publication 20150025268A1 · Jan 22, 2015