Photo-latent titanium catalysts

Patent metadata

Field	Value
Publication number	US-10207261-B2
Application number	US-201013395467-A
Country	US
Kind code	B2
Filing date	Sep 9, 2010
Priority date	Sep 15, 2009
Publication date	Feb 19, 2019
Grant date	Feb 19, 2019

Abstract

The present invention provides a photolatent Ti-chelate catalyst formulation, comprising (i) at least one compound of the formula (I) wherein R 1 is C 1 -C 20 alkyl or C 2 -C 20 alkyl which is interrupted by one or more non-consecutive O-atoms; Y is formula (II) or optionally substituted phenyl; Y 1 is formula (III) or optionally substituted phenyl; Y 2 is formula (IV) or optionally substituted phenyl; Y 3 is formula (V) or optionally substituted phenyl; R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 independently of each other are hydrogen, halogen, optionally substituted C 1 -C 20 alkyl, or R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 independently of each other are optionally substituted C 6 -C 14 aryl, provided that only one of R 2 , R 3 , R 4 is hydrogen and only one of R 5 , R 6 , R 7 is hydrogen and only one of R 8 , R 9 , R 10 is hydrogen and only one of R 11 , R 12 , R 13 is hydrogen; and (ii) at least one chelate ligand compound of the formula IIa, IIb or IIc, wherein Y′ is formula (VI) or formula (VII); Y′ 1 is formula (VIII) or formula (IX); R′ 2 , R′ 3 , R′ 4 , R′ 5 , R′ 6 and R′ 7 independently of each other have on of the meanings as given for R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 ; and R′ 14 , R′ 15 and R′ 16 independently of each other have on of the meanings as given for R 14 , R 15 and R 16 .

First claim

The invention claimed is:

1. Ti-chelate catalyst formulation comprising:
(i) 95-70% by weight of at least one compound
selected from the group consisting of

based on the total catalyst formulation; and
(ii) at least one chelate ligand compound

wherein 5-30% by weight of at least one chelate ligand is present based on the total catalyst formulation.

2. A polymerizable composition comprising
(a) at least one blocked or unblocked isocyanate or isothiocyanate component,
(b) at least one polyol; and
(c) at least one Ti-chelate catalyst formulation as defined in claim 1 .

3. A polymerizable composition according to claim 2 , comprising in addition to components (a), (b) and (c), (d) a photosensitizer compound.

4. A method of using the polymerizable composition according to claim 2 comprising: incorporating the polymerizable composition according to claim 2 in adhesives, coatings, sealings, potting components, printing inks, printing plates, foams, moulding compounds, or photostructured layers.

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

6. A polymerizable composition comprises
(a) at least one blocked or unblocked isocyanate or isothiocyanate component,
(b) at least one polyol; and
(c) at least one Ti-chelate catalyst formulation as defined in claim 1 , which comprises 0.001 to 15% by weight of (c) based on the total composition.

7. A polymerizable composition according to claim 6 comprises 0.01 to 5% by weight of (c) based on the total composition.

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

9. A process according to claim 8 , wherein the component which is capable to crosslink in the presence of a Lewis acid is a mixture of (a) a blocked or unblocked isocyanate or isothiocyanate component and (b) a polyol.

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 process for polymerizing compounds, which are capable to crosslink in the presence of a Lewis acid, characterized in that a Ti-chelate catalyst formulation as defined in claim 1 is added to said compounds and the resulting mixture is subjected to a heat treatment, or the mixture is irradiated with electromagnetic radiation of a wavelength range of 200-800 nm and simultaneously with or after the irradiation subjected to a heat treatment.

12. A Ti-chelate catalyst formulation comprising:
(i) at least one compound of the formula I

wherein
R 1 is C 1 -C 8 alkyl or C 2 -C 12 alkyl, which is interrupted by 1-6 non-consecutive O-atoms;
Y is

Y 1 is

Y 2 is

Y 3 is

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 independently of each other are hydrogen, halogen, phenyl or C 1 -C 4 alkyl,
provided that only one of R 2 , R 3 , R 4 is hydrogen and only one of R 5 , R 6 , R 7 is hydrogen and only one of R 5 , R 9 , R 10 is hydrogen and only one of R 11 , R 12 , R 13 is hydrogen;
or R 5 and R 6 , and/or R 5 and R 9 , together with the C-atom to which they are attached form a 5 or 6 membered saturated ring,
R 14 , R 15 and R 16 independently of each other are hydrogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, benzoyl, nitro or NR 17 R 18 ;
or R 14 and R 15 together with the phenyl ring to which they are attached form thioxanthyl which is unsubstituted or is substituted by C 1 -C 4 alkyl;
R 17 and R 15 are C 1 -C 4 alkyl; and
(ii) at least one chelate ligand compound

wherein (i) 95-70% by weight of at least one compound of the formula I, and (ii) 5-30% by weight of at least one chelate ligand compound are present based on the total catalyst formulation.

Assignees

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

Inventors

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

Classifications

• B01J2531/46

  Titanium · CPC title

• B01J2231/34

  Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N · CPC title

• B01J31/0208

  Ketones or ketals · CPC title

• B01J31/2213

  At least two complexing oxygen atoms present in an at least bidentate or bridging ligand · CPC title

• B01J31/2234 Primary

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