Organometallic compositions and coating compositions

• US 7,485,729 B2
• Filed: 07/17/2006
• Issued: 02/03/2009
• Est. Priority Date: 08/12/2004
• Status: Expired due to Fees

• Current Assignee: King Industries
• Original Assignee: King Industries
• Inventors: Ravichandran, Ramanathan, Abi-Karam, Farouk, Hsieh, Bing
• Primary Examiner(s): SANDERS, KRIELLION ANTIONETTE
• Application Number:
  US11/458,015
• Publication Number:
  US 20060247341A1
• Time in Patent Office: 932 Days
• Field of Search: 252/389.53, 252/389.54, 252/389.61, 252/401, 252/403, 252/407, 524/87, 524/99, 524/102, 524/103, 524/105, 524/106, 524/195, 524/315, 524/317, 524/318, 524/492, 548/103, 548/107, 548/352.1, 560/129
• US Class Current: 548/103
• CPC Class Codes: B01J 2531/26 Zinc
• CPC Class Codes: B01J 31/181 Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
• CPC Class Codes: C08G 18/163 covered by C08G18/18 and C08G18/22
• CPC Class Codes: C08G 18/222 metal compounds not provided for in groups C08G18/225 - C08G18/26
• CPC Class Codes: C08G 18/227 of antimony, bismuth or arsenic
• CPC Class Codes: C08G 18/244 tin salts of carboxylic acids
• CPC Class Codes: C08G 18/6216 Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
• CPC Class Codes: C08G 18/798 containing urethdione groups
• CPC Class Codes: C08G 18/8064 with monohydroxy compounds
• CPC Class Codes: C08G 18/807 with nitrogen containing compounds
• CPC Class Codes: C08G 18/8074 Lactams
• CPC Class Codes: C08G 2150/20 Compositions for powder coatings
• CPC Class Codes: C08K 5/0091 Complexes with metal-heteroatom-bonds
• CPC Class Codes: C08L 33/02 Homopolymers or copolymers of acids; Metal or ammonium salts thereof
• CPC Class Codes: C08L 75/00 Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
• CPC Class Codes: C09D 163/00 Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• CPC Class Codes: C09D 175/04 Polyurethanes

Abstract

The present invention is directed to novel organometallic complexes as catalysts for the reaction of compounds with isocyanate and hydroxyl functional groups to form urethane and/or polyurethane and the process employing such catalysts. More particularly, the present invention is directed to novel complexes of zinc(II) with substituted amidines. These novel catalysts are useful for the production of urethanes and polyurethanes which are important in many industrial applications.

Claims

1. An anhydrous compound of formula VI

Zn(X)₂(Y)₂ 

 

(VI)

wherein;

Zn may be substituted with a metal from the group consisting of aluminum, bismuth and zirconium;

Y is an aliphatic carboxylate with an equivalent weight of about 45 to about 465; and

X is an amidine of formula VII or VIII;

2. A compound according to claim 1 that is selected from the group consisting of Zn(tetramethylguanidine)₂(acetate)₂, Zn(tetramethylguanidine)₂(formate)₂, Zn(tetramethylguanidine)₂(2-ethylhexanoate)₂, Zn(1,3-diphenylguanidine)₂(acetate)₂, Zn(1,3-diphenylguanidine)₂(formate)₂ and Zn(1,3-diphenylguanidine)₂(2-ethylhexanoate)₂.

3. A compound according to claim 1 that is selected from the group consisting of Zn(1-methylimidazole)₂(acetate)₂, Zn(1-methylimidazole)₂(formate)₂, Zn(1-methylimidazole)₂(2-ethylhexanoate)₂, Zn(1,2-dimethylimidazole)₂(acetate)₂, Zn(1,2-dimethylimidazole)₂(formate)₂, Zn(1,2-dimethylimidazole)₂(2-ethylhexanoate)₂, Zn(1-butylimidazole)₂(acetate)₂, Zn(1-butylimidazole)₂(formate)₂, Zn(1-butylimidazole)₂(2-ethylhexanoate)₂, Zn(imidazole)₂(acetate)₂, Zn(imidazole)₂(formate)₂, Zn(imidazole)₂(2-ethylhexanoate)₂, Zn(1-(2-hydroxypropyl)imidazole)₂(acetate)₂, Zn(1-(2-hydroxypropyl)imidazole)₂(formate)₂, Zn(1-(2-hydroxypropyl)imidazole)₂(2-ethylhexanoate)₂, Zn(4,4-dimethyl-2-imidazoline)₂(acetate)₂, Zn(4,4-dimethyl-2-imidazoline)₂(formate)₂, Zn(4,4-dimethyl-2-imidazoline)₂(2-ethylhexanoate)₂, Zn(tall oil hydroxyethyl imidazoline)₂(acetate)₂, Zn(tall oil hydroxyethyl-imidazoline)₂(formate)₂, and Zn(tall oil hydroxyethyl imidazoline)₂(2-ethylhexanoate)₂.

4. A compound according to claim 1 that is selected from the group consisting of Zn(1,5-Diazabicyclo[4.3.0]non-5-ene)₂(acetate)₂, Zn(1,5-Diazabicyclo[4.3.0]non-5-ene)₂(formate)₂, Zn(1,5-Diazabicyclo[4.3.0]non-5-ene)₂(2-ethylhexanoate)₂, Zn(1,8-Diazabicyclo[5.4.0]undec-7-ene)₂(acetate)₂, Zn(1,8-Diazabicyclo[5.4.0]undec-7-ene)₂(formate)₂ and Zn(1,8-Diazabicyclo[5.4.0]undec-7-ene)₂(2-ethylhexanoate)₂.

5. A compound according to claim 1 that is Zn(1-methylimidazole)₂(acetate)₂.

6. A compound according to claim 1 that is Zn(1-methylimidazole)₂(2-ethylhexanoate)₂.