Photo-latent titanium-oxo-chelate catalysts

Patent metadata

Field	Value
Publication number	US-9809727-B2
Application number	US-201214007688-A
Country	US
Kind code	B2
Filing date	Apr 2, 2012
Priority date	Apr 5, 2011
Publication date	Nov 7, 2017
Grant date	Nov 7, 2017

Abstract

A titanium-oxo-chelate catalyst formulation, comprising: (i) at least one compound of the formula (I), wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 independently of each other are for example hydrogen, halogen, C 1 -C 20 alkyl, C 6 -C 14 aryl which is unsubstituted or substituted; or R 1 , R 2 and R 3 and/or R 4 , R 5 and R 6 and/or R 7 , R 8 and R 9 and/or R 10 , R 11 and R 12 together with the C-atom to which they are attached each form a C 6 -C 14 aryl group which is unsubstituted or substituted; or R 1 and R 2 and/or R 4 and R 5 and/or R 7 and R 8 and/or R 10 and R 11 together with the C-atom to which they are attached form a 5- to 7-membered carbocyclic ring; at least one chelate ligand compound of the formula (IIa), (IIb) or (IIc), wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are defined as above for formula (I), is suitable as photolatent catalyst formulation for polymerizing compounds, which are capable to crosslink in the presence of a Lewis acid.

First claim

The invention claimed is:

1. A titanium-oxo-chelate catalyst formulation, comprising:
(i) 50-99% by weight of at least one compound of formula I

wherein
R 1 , R 2 , and R 3 together with the C-atom to which they are attached form a C 6 -C 14 aryl group which is unsubstituted or substituted by one, two or three C 1 -C 8 alkyl, halogen, OR 13 or NR 13 R 14 ;
R 10 , R 11 , and R 12 together with the C-atom to which they are attached form a C 6 -C 14 aryl group which is unsubstituted or substituted by one, two or three C 1 -C 8 alkyl, halogen, OR 13 , or NR 13 R 14 ;
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 independently of each other are hydrogen, halogen, C 1 -C 20 alkyl, or C 6 -C 14 aryl which is unsubstituted or substituted by one, two or three C 1 -C 8 alkyl, halogen, OR 13 , or NR 13 R 14 ;
provided that only one of R 4 , R 5 , and R 6 in the group

and only one of R 7 , R 8 , and R 9 in the group

can be hydrogen;
or R 4 , R 5 , and R 6 and/or R 7 , R 8 , and R 9 together with the C-atom to which they are attached each form a C 6 -C 14 aryl group which is unsubstituted or substituted by one, two or three C 1 -C 8 alkyl, halogen, OR 13 , or NR 13 R 14 ;
or R 4 and R 5 and/or R 7 and R 8 together with the C-atom to which they are attached form a 5- to 7-membered carbocyclic ring; and

(ii) 1-50% by weight of at least one chelate ligand compound of the formula IIa, IIb, or IIc

wherein R 1 , R 2 , and R 3 independently of each other are hydrogen, halogen, C 1 -C 20 alkyl, or C 6 -C 14 aryl which is unsubstituted or substituted by one, two or three C 1 -C 8 alkyl, halogen, OR 12 or NR 13 R 14 ; or
R 1 , R 2 and R 3 together with the C-atom to which they are attached form a C 6 -C 14 aryl group which is unsubstituted or substituted by one, two or three C 1 -C 8 alkyl, halogen, OR 13 , or NR 13 R 1 ; and
R 4 , R 5 , and R 6 independently of each other are hydrogen, halogen, C 1 -C 20 alkyl, or C 6 -C 14 aryl which is unsubstituted or substituted by one, two or three C 1 -C 8 alkyl, halogen, OR 13 or NR 13 R 14 ; or
R 4 , R 5 and R 6 together with the C-atom to which they are attached form a C 6 -C 14 aryl group which is unsubstituted or substituted by one, two or three C 1 -C 8 alkyl, halogen, OR 13 , or NR 13 R 14 ;
wherein
R 13 and R 14 independently of each other are C 1 -C 8 alkyl.

2. A polymerizable composition comprising:
(a) at least one component which is capable of a polyaddition or polycondensation reaction in the presence of Lewis-acid type reactants; and
(b) at least one titanium-oxo-chelate catalyst compound of the formula I as defined in claim 1 .

3. A polymerizable composition according to claim 2 comprising as component (a):
(a1) at least one blocked or unblocked isocyanate or isothiocyanate component, and
(a2) at least one polyol.

4. A polymerizable composition according to claim 2 , comprising in addition to components (a) and (b) a further additive (d), which further addititve is a photosensitizer compound.

5. A polymerizable composition according to claim 2 , which comprises 0.001 to 15% by weight, of the titanium-oxo-chelate catalyst compound of the formula I as defined in claim 1 , based on the total composition.

6. A coated substrate coated on at least one surface with a composition according to claim 2 .

7. A polymerized or crosslinked composition according to claim 2 .

8. A process for polymerizing compounds, which are capable of crosslinking in the presence of a Lewis acid, characterized in that the titanium-oxo-chelate catalyst compound of formula I as defined in claim 1 is added to the compounds which are capable to crosslink in the presence of a Lewis acid and the resulting mixture is irradiated with electromagnetic radiation of a wavelength range of 200-800 nm.

9. A process according to claim 8 , characterized in that instead of irradiating with electromagnetic radiation the mixture is subjected to a heat treatment, or the mixture is irradiated with electromagnetic radiation and simultaneously with or after the irradiation subjected to a heat treatment.

10. A process according to claim 8 for the preparation of adhesives, sealings, coatings, potting components, printing inks, printing plates, foams, moulding compounds, or photostructured layers.

11. A titanium-oxo-chelate catalyst formulation, comprising
(i) a compound of formula

and
(ii) a chelate ligand compound of formula

12. A titanium-oxo-chelate catalyst formulation according to claim 1 , comprising
(i) at least one compound of formula I, wherein
R 1 , R 2 , and R 3 together with the C-atom to which they are attached form a phenyl group which is unsubstituted or substituted by one, two, or three C 1 -C 8 alkyl, halogen, OR 13 , or NR 13 R 14 ;
R 10 , R 11 , and R 12 together with the C-atom to which they are attached form a phenyl group which is unsubstituted or substituted by one, two, or three C 1 -C 8 alkyl, halogen, OR 13 , or NR 13 R 14 ;
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 independently of each other are hydrogen, halogen, C 1 -C 20 alkyl, or C 6 -C 14 aryl which is unsubstituted or substituted by one, two or three C 1 -C 8 alkyl, halogen, OR 13 , or NR 13 R 14 ; or
R 4 , R 5 , and R 6 and/or R 7 , R 8 , and R 9 together with the C-atom to which they are attached form a C 6 -C 14 aryl group which is unsubstituted or substituted by one, two or three C 1 -C 8 alkyl, halogen, OR 13 , or NR 13 R 14 ; or
R 4 and R 5 and/or R 7 and R 8 together with the C-atom to which they are attached form a 5- to 7- membered carbocyclic ring; and

(ii) at least one chelate ligand compound of the formula IIa, IIb, or IIc, wherein
R 1 , R 2 , and R 3 independently of each other are hydrogen, halogen, or C 1 -C 20 alkyl; or
R 1 , R 2 and R 3 together with the C-atom to which they are attached form a phenyl group which is unsubstituted or substituted by one, two or three C 1 -C 8 alkyl, halogen OR 13 , or NR 13 R 14 ; and
R 4 , R 5 , and R 6 independently of each other are hydrogen, halogen, C 1 -C 20 alkyl; or
R 4 , R 5 and R 6 together with the C-atom to which they are attached form a phenyl group which is unsubstituted or substituted by one, two or three C 1 -C 8 alkyl, halogen OR 13 , or NR 13 R 14 ;
wherein
R 13 and R 14 independently of each other are C 1 -C 8 alkyl.

13. A titanium-oxo-chelate catalyst formulation according to claim 1 , comprising
(i) at least one compound of formula I, wherein
R 1 , R 2 , and R 3 together with the C-atom to which they are attached form a phenyl group which is unsubstituted or substituted by one, two, or three C 1 -C 4 alkyl, OR 13 , or NR 13 R 14 ;
R 10 , R 11 , and R 12 together with the C-atom to which they are attached form a phenyl group which is unsubstituted or substituted by one, two, or three C 1 -C 4 alkyl, OR 13 , or NR 13 R 14 ;
R 4 , R 5 , R 6 , R 7 , R 8 , R 9 independently of each other are hydrogen, halogen, or C 1 -C 4 alkyl

Assignees

• Hintermann Tobias
• Carroy Antoine
• Lordelot Caroline
• Bauer Didier
• Steck Rachel Kohli
• Faller Marc
• Basf Se

Inventors

• Hintermann Tobias
• Carroy Antoine
• Lordelot Caroline
• Bauer Didier
• Steck Rachel Kohli
• Faller Marc

Classifications

• C09J175/04

  Polyurethanes · CPC title

• B01J31/2234

  Beta-dicarbonyl ligands, e.g. acetylacetonates · CPC title

• Y02P20/52

  using catalysts, e.g. selective catalysts · CPC title

• B01J2531/46

  Titanium · CPC title

• C09D175/16 Primary

  having terminal carbon-to-carbon unsaturated bonds · CPC title