Curable composition comprising a thermolatent base

Patent metadata

Field	Value
Publication number	US-8969577-B2
Application number	US-200913130331-A
Country	US
Kind code	B2
Filing date	Nov 18, 2009
Priority date	Nov 24, 2008
Publication date	Mar 3, 2015
Grant date	Mar 3, 2015

Abstract

The present invention relates to curable compositions comprising a thermolatent amidine base and an organic material which is polymerizable or crosslinkable with a basic or nucleophilic catalyst. In particular, the invention relates to curable coating compositions, especially powder coating compositions, and curable adhesive compositions, as well as to the use a thermolatent amidine base as a curing catalyst for thermally induced base-catalyzed polymerization or crosslinking reactions.

First claim

The invention claimed is:

1. A curable composition comprising
(A) an organic material which is polymerisable or crosslinkable with a basic or nucleophilic catalyst,
(B) a compound of the formula

wherein
R 1 forms together with the carbon and nitrogen atom, it is linked to, a mono- or polycyclic C 2 -C 20 ring system selected from the group consisting of imidazole, benzimidazole, thiazole, benzothiazole, pyrazole, oxazole, benzoxazole, isoxazole, isothiazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, pyridine, quinoline, isoquinoline, phenanthridine, pyridazine, pyrimidine, pyrazine, cinnoline, phthalazine, chinazoline, chinoxaline, chinazolinone, 1,3,5-triazine, 1,2,4,5-tetrazine, purine, xanthine, hypoxanthine, guanine, adenine, pteridine, pterine, 1,10-phenanthroline, 2,2′-bipyridine, 4,4′-bipyridine,

said ring system is unsubstituted or substituted by C 1 -C 8 alkyl; C 5 -C 7 cycloalkyl; C 6 -C 12 aryl; C 6 -C 18 aryl, which is substituted by G; C 2 -C 18 heteroaryl; C 2 -C 18 heteroaryl, which is substituted by G; C 1 -C 8 alkoxy; C 1 -C 8 alkoxy, which is substituted by E and/or interrupted by D; C 7 -C 11 aralkyl; C 7 -C 11 aralkyl, which is substituted by G;
halogen, OH, oxo, CN, NH 2 , NHR 6 , NR 7 R 8 , CONH 2 , CONR 9 R 10 , COR 11 , C(O)OR 12 ,
wherein R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are independently of each other C 1 -C 8 alkyl; C 1 -C 8 alkyl, which is interrupted by —O—; C 6 -C 12 aryl; C 6 -C 12 aryl, which is substituted by C 1 -C 8 alkyl or C 1 -C 8 alkoxy; C 7 -C 11 aralkyl; C 7 -C 11 aralkyl, which is substituted by G;
or R 7 and R 8 form an organic bridging group completing, together with the nitrogen atom, they are linked to, a heterocyclic ring of 5 to 7 ring atoms in total;
or said ring system is further anellated by one or more benzene rings
R 2 , R 3 , R 4 and R 5 are independently of each other H; C 1 -C 18 alkyl; C 1 -C 18 alkyl, which is substituted by E and/or interrupted by D; C 5 -C 12 cycloalkyl; C 5 -C 12 cycloalkyl, which is substituted by E; C 6 -C 12 aryl; C 6 -C 18 aryl, which is substituted by G; C 2 -C 18 heteroaryl; C 2 -C 18 heteroaryl, which is substituted by G; C 1 -C 18 alkoxy; C 1 -C 18 alkoxy, which is substituted by E and/or interrupted by D; C 7 -C 18 aralkyl; C 7 -C 18 aralkyl, which is substituted by G; NHR 18 , NR 19 R 20 , COOH;
or R 2 and R 3 , R 4 and R 5 , or R 2 and R 4 form an organic bridging group completing, together with the carbon atom, they are linked to, a carbocyclic or heterocyclic ring of 5 to 12 ring atoms in total;
or two of R 5 , which are linked to adjacent carbon atoms, form an organic bridging group completing, together with the carbon atom, they are linked to, a carbocyclic or heterocyclic ring of 5 to 12 ring atoms in total;
D is —CO—; —COO—; —S—; —SO—; —SO 2 —; —O—; —NR 21 —; —SiR 22 R 23 —; —POR 24 —; —CR 25 ═CR 26 —; or —C≡C—;
E is OR 27 ; SR 28 ; SOR 29 ; SO 2 R 30 ; NR 31 R 32 ; COR 33 ; COOR 34 ; CONR 35 R 36 ; PO(R 37 ) 2 ; CN; or halogen; and
G is E or C 1 -C 18 alkyl;
R 18 , R 19 , R 20 , R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 , R 28 , R 29 , R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 and R 37 are independently of each other C 1 -C 18 alkyl; C 1 -C 18 alkyl, which is interrupted by —O—; C 6 -C 18 aryl; C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl or C 1 -C 18 alkoxy; C 7 -C 18 aralkyl; C 7 -C 18 aralkyl, which is substituted by G; C 2 -C 18 heteroaryl;
or R 19 and R 20 , R 31 and R 32 , or R 35 and R 36 form an organic bridging group completing, together with the nitrogen atom, they are linked to, a heterocyclic ring of 5 to 7 ring atoms in total;
L is a n-valent leaving group,
n is an integer of 1, 2, 3 or 4;
p is an integer of 1, 2, 3 or 4,
(C) a curing catalyst other than component (B) and
(D) at least one additive
if n is 1, L is halogen, OH, OR 40 , SR 40 , OCOR 40 , OCOOR 41 , OCONR 42 R 43 , OCSNR 42 R 43 , OSO 2 R 40 , OSO 3 R 40 , NR 42 R 43 , S + R 42 R 43 X − , N + R 42 R 43 R 44 X − , P + R 42 R 43 X − , NHCOR 40 , OPO(OR 40 ) 2 , OPO(R 46 )(OR 47 ), OSi(R 40 ) 3 ;
wherein
R 40 , R 42 , R 43 , R 44 , R 45 , R 46 and R 47 are independently of each other H, C 1 -C 18 alkyl or C 1 -C 18 alkyl, which is substituted by E and/or interrupted by D; C 5 -C 12 cycloalkyl, C 5 -C 12 cycloalkyl, which is substituted by E and/or interrupted by D; C 6 -C 18 aryl; C 6 -C 18 aryl, which is substituted by G; C 7 -C 18 aralkyl; C 7 -C 18 aralkyl, which is substituted by G; C 2 -C 18 heteroaryl; C 2 -C 18 heteroaryl, which is substituted by G;
or R 42 and R 43 form an organic bridging group completing, together with the nitrogen atom, they are linked to, a heterocyclic ring of 5 to 7 ring atoms in total;
or two of R 45 form a bridging group completing, together with the —OC—N—CO-group, they are linked to, a heterocyclic ring of 5 to 7 ring atoms in total;
R 41 is C 1 -C 18 alkyl or C 1 -C 18 alkyl, which is substituted by E and/or interrupted by D; C 5 -C 12 cycloalkyl, C 5 -C 12 cycloalkyl, which is substituted by E and/or interrupted by D; C 6 -C 18 aryl; C 1 -C 18 aryl, which is substituted by G; C 2 -C 18 heteroaryl; C 2 -C 18 heteroaryl, which is substituted by G;
X − is halide, hydroxide, C 1 -C 18 alkylsulfonate, C 6 -C 18 arylsulfonate, R 48 COO − , HSO 4 − or ½ SO 4 2− , wherein R 48 is H, C 1 -C 18 alkyl or C 1 -C 18 alkyl, which is substituted by E and/or interrupted by D; C 5 -C 12 cycloalkyl, C 5 -C 12 cycloalkyl, which is substituted by E and/or interrupted by D; C 6 -C 18 aryl; C 6 -C 18 aryl, which is substituted by G; C 2 -C 18 heteroaryl; C 2 -C 18 heteroaryl, which is substituted by G;
if n is 2, L is —OCO—O—,

—OSO 2 O—, —OCO—(CH 2 ) q —COO—, —OSi(CH 3 ) 2 O—, —OCON(CH 2 ) q , wherein q is 0 or an integer of 1 to 10; or
if n is 3 or 4, L is

2. A composition according to claim 1 , wherein R 2 , R 3 , R 4 and R 5 are independently of each other H; C 1 -C 8 alkyl; C 5 -C 8 cycloalkyl; C 6 -C 18 aryl; C 6 -C 18 aryl, which is substituted by G; C 2 -C 18 heteroaryl; C 2 -C 18 heteroaryl, which is substituted by G; C 1 -C 4 alkoxy; C 7 -C 10 aralkyl; NHR 6 , NR 7 R 8 ,
wherein R 6 , R 7 and R 8 are independently of each other C 1 -C 4 alkyl; C 6 -C 12 aryl; C 6 -C 12 aryl, which is substituted by C 1 -C 4 alkyl or C 1 -C 4 alkoxy; C 7 -C 10 aralkyl;
or R 7 and R 8 form an organic bridging group completing, together with the nitrogen atom, they are linked to, a heterocyclic ring of 5 to 7 ring atoms in total;
or R 2 and R 3 , R 4 and R 5 , or R 2 and R 4 form an organic bridging group completing, together with the carbon atom, they are linked to, a carbocyclic or heterocyclic ring of 5 to 7 ring atoms in total;
or two of R 5 , which are linked to adjacent carbon atoms, form an organic bridging group completing, together with the carbon atom, they are linked to, a carbocyclic or heterocyclic ring of 5 to 7 ring atoms in total.

3. A composition according to claim 1 , wherein R 2 , R 3 , R 4 and R 5 are independently of each other H or C 1 -C 4 alkyl, and
p is an integer of 1 or 2.

4. A composition according to claim 1

Assignees

• Nesvadba Peter
• Folger Lucienne Bugnon
• Knischka Ralf
• Basf Se

Inventors

• Nesvadba Peter
• Folger Lucienne Bugnon
• Knischka Ralf

Classifications

• C07D215/38

  Nitrogen atoms (nitro radicals C07D215/18) · CPC title

• C08G59/686

  containing nitrogen · CPC title

• C07D213/74 Primary

  Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C08G59/4246

  polymers with carboxylic terminal groups · CPC title