IP Library Granted Patent US 9,416,215
Granted Patent B2
US 9,416,215 · App. 12/990,664 · Granted Aug 16, 2016

Catalysts and use thereof in the production of polyurethanes

Inventors: Jens Krause (Mours Saint Eusebe, FR); Stephan Reiter (Köln, DE); Stefan Lindner (Köln, DE); Axel Schmidt (Singapore, SG); Klaus Jurkschat (Dortmund, DE); Markus Schürmann (Recklinghausen, DE); Gerrit Bradtmöller (Dorsten, DE)
Assignee: Covestro Deutschland AG
C08G18/24B01J31/0211B01J31/0228B01J31/0237B01J31/0241C08G18/10C08G18/792B01J2231/341B01J2531/42Y02P20/52
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Quick Facts
Patent No.
US 9,416,215
App. No.
12/990,664
Granted
Aug 16, 2016
Kind
B2
Abstract

The present invention relates to new catalysts and production thereof as well as the preferred use thereof in the production of polyisocyanate polyaddition products. The described catalysts are tetravalent tin compounds with at least one ligand bonded via at least one oxygen atom or sulfur atom and containing at least one nitrogen atom.

Claims (50)

1. A latent catalyst consisting of a tetravalent mononuclear tin compound of the formula I with at least one ligand bonded via at least one oxygen atom or sulfur atom and comprising at least one nitrogen atom,

Sn(IV)(L 1 ) n1 (L 2 ) n2 (L 3 ) n3 (L 4 ) n4   (I)

wherein n1, n2, n3, and n4 are, independently of one another, an integer from 0 to 1 and L 1 , L 2 , L 3 , and L 4 are, independently of one another, univalent, divalent, trivalent or tetravalent ligands

wherein at least one ligand per Sn atom has the following significance:

—X—Y

wherein

X=O, S, OC(O), OC(S), O(O)S(O)O, O(O)S(O)

Y=—R1-N(R2)(R3) or —R1-C(R4)=NR2

wherein R1, R2, R3, and R4 are, independently of one another, saturated or unsaturated, cyclic or acyclic, branched or unbranched, substituted or unsubstituted hydrocarbon residues optionally interrupted by heteroatoms, or R2, R3, and R4 are, independently of one another, hydrogen, R1-X, or R2 and R3 or R2 and R1 or R3 and R1 or R4 and R1 or R4 and R2 form a ring; and

wherein the remaining ligands are, independently of one another, —X—Y with the aforementioned significance or have the following significance:

halides, hydroxide, saturated or unsaturated, cyclic or acyclic, branched or unbranched, substituted or unsubstituted hydrocarbon residues bonded to the tin atom by way of at least one oxygen or sulfur.

2. A process for preparing a polyisocyanate polyaddition product which comprises reacting a polyisocyanate and a NCO-reactive compound with the latent catalyst according to claim 1 .

3. A polyisocyanate polyaddition product, obtained from reacting

a) a polyisocyanate; and

b) a NCO-reactive compound

in the presence of

c) a latent catalyst;

d) optionally, a further catalyst and/or activator different from c)

with addition of

e) optionally, a blowing agent;

f) optionally, a filler and/or fibrous material;

g) optionally, an auxiliary agent and/or additive;

wherein the latent catalyst comprises a tetravalent mononuclear tin compound of the formula I with at least one ligand bonded via at least one oxygen atom or sulfur atom and comprising at least one nitrogen atom

Sn(IV)(L 1 ) n1 (L 2 ) n2 (L 3 ) n3 (L 4 ) n4   (I)

wherein

n1, n2, n3, and n4 are, independently of one another, an integer from 0 to 1 and L 1 , L 2 , L 3 , and L 4 are, independently of one another, univalent, divalent, trivalent or tetravalent ligands or tetravalent polynuclear tin compounds based thereon,

wherein at least one ligand per Sn atom has the following significance:

—X—Y

wherein

X=O, S, OC(O), OC(S), O(O)S(O)O, O(O)S(O)

Y=—R1-N(R2)(R3) or —R1-C(R4)=NR2

wherein, R1, R2, R3, and R4 are, independently of one another, saturated or unsaturated, cyclic or acyclic, branched or unbranched, substituted or unsubstituted hydrocarbon residues optionally interrupted by heteroatoms, or R2, R3, and R4 are, independently of one another, hydrogen, R1-X, or R2 and R3 or R2 and R1 or R3 and R1 or R4 and R1 or R4 and R2 form a ring; and

wherein the remaining ligands are, independently of one another, —X—Y with the aforementioned significance or have the following significance:

halides, hydroxide, saturated or unsaturated, cyclic or acyclic, branched or unbranched, substituted or unsubstituted hydrocarbon residues bonded to the tin atom by way of at least one oxygen or sulfur.

4. The polyisocyanate polyaddition product according to claim 3 , wherein the latent catalyst comprises a tin compound selected from the group consisting of

Formulae (a) and (d) to (j):

wherein iPr is isopropyl-, Me is methyl-, Bu is n-butyl-, Ph is phenyl-, and R and R′ are, identically or differently, alkyl groups.

5. The polyisocyanate polyaddition product according to claim 3 , wherein the latent catalyst comprises a tin compound selected from the group consisting of

Formulae (d) to (j):

wherein iPr is isopropyl-, Me is methyl-, Bu is n-butyl-, and Ph is phenyl-.

6. A process for preparing the polyisocyanate polyaddition product according to claim 3 , wherein the polyisocyanate (a) is converted with the NCO-reactive compound (b) in the presence of the latent catalyst (c) and, optionally, adding the catalyst and/or activator different from (c) with addition of, optionally, the blowing agent, optionally the filler and/or the fibrous material and, optionally, auxiliary substances and/or additives, wherein the latent catalyst comprises tetravalent mononuclear tin compounds of the formula I with at least one ligand bonded via at least one oxygen atom or sulfur atom and comprising at least one nitrogen atom

Sn(IV)(L 1 ) n1 (L 2 ) n2 (L 3 ) n3 (L 4 ) n4   (I)

wherein n1, n2, n3, and n4 are, independently of one another, an integer from 0 to 1 and wherein L 1 , L 2 , L 3 , and L 4 are, independently of one another, univalent, divalent, trivalent or tetravalent ligands or tetravalent polynuclear tin compounds based thereon, wherein at least one ligand per Sn atom has the following significance:

—X—Y

wherein

X=O, S, OC(O), OC(S), O(O)S(O)O, O(O)S(O)

Y=—R1-N(R2)(R3) or —R1-C(R4)=NR2

wherein R1, R2, R3, and R4 are, independently of one another, saturated or unsaturated, cyclic or acyclic, branched or unbranched, substituted or unsubstituted hydrocarbon residues optionally interrupted by heteroatoms, or R2, R3, and R4 are, independently of one another, hydrogen, R1-X, or R2 and R3 or R2 and R1 or R3 and R1 or R4 and R1 or R4 and R2 form a ring; and

wherein the remaining ligands independently of one another are —X—Y with the aforementioned significance or have the following significance:

halides, hydroxide, saturated or unsaturated, cyclic or acyclic, branched or unbranched, substituted or unsubstituted hydrocarbon residues bonded to the tin atom by way of at least one oxygen or sulfur.

Assignments (5)
CHANGE OF NAME Recorded Apr 6, 2016
From: BAYER MATERIALSCIENCE AG
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 038370/0892 →
CHANGE OF NAME Recorded Mar 21, 2016
From: BAYER MATERIALSCIENCE AG
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 038188/0408 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 10, 2016
From: BAYER INTELLECTUAL PROPERTY GMBH
To: BAYER MATERIALSCIENCE AG
Reel/Frame 038056/0732 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 24, 2015
From: BAYER MATERIALSCIENCE AG
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 035892/0536 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 2, 2010
From: KRAUSE, JENS; REITER, STEPHAN; LINDNER, STEFAN; SCHMIDT, AXEL; JURKSCHAT, KLAUS; SCHURMANN, MARKUS; BRADTMOELLER, GERRIT
To: BAYER MATERIALSCIENCE AG
Reel/Frame 025232/0287 →
Priority Claims (1)
DE 10 2008 021 980 · May 2, 2008 · national
Continuity (1)
Related Publication 20110054140A1 · Mar 3, 2011