Cure accelerators for anaerobic curable compositions
The present invention relates to cure accelerators useful for anaerobic curable compositions, such as adhesives and sealants. The cure accelerators are embraced within where X is CH 2 , O, S, NR 4 , CR 5 R 6 or C═O, wherein R 4 , R 5 , and R 6 are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; R is one or more of hydrogen, alkyl, alkenyl, alkynl, hydroxyalkyl, hydroxyalkenyl, or hydroxyalkynl; R 1 , R 2 , and R 3 are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; R 7 is hydrogen or CHR 8 R 9 , where R 8 and R 9 are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; and n is 0 or 1. A particularly desirable example is 1,2,3,4-tetrahydrobenzo-h-quinolin-3-ol.
1. An anaerobic curable composition comprising:
(a) a (meth)acrylate component;
(b) an anaerobic cure-inducing composition; and
(c) a cure accelerator embraced by
wherein X is CH 2 , O, S, NR 4 , CR 5 R 6 or C═O, wherein R 4 , R 5 , and R 6 are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; R is hydrogen, alkyl, alkenyl, alkynl, hydroxyalkyl, hydroxyalkenyl, or hydroxyalkynl; R 1 , R 2 , and R 3 are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; R 7 is hydrogen or CHR 8 R 9 , wherein R 8 and R 9 are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; and n is 0 or 1.
2. The composition according to claim 1 , wherein the anaerobic cure-inducing composition comprises a hydroperoxide selected from the group consisting of t-butyl hydroperoxide, p-methane hydroperoxide, cumene hydroperoxide, diisopropylbenzene hydroperoxide, and mixtures thereof.
3. The composition according to claim 1 , further comprising at least one co-accelerator.
4. The composition according to claim 3 , wherein the co-accelerator is selected from the group consisting of amines, amine oxides, sulfonamides, metal sources, acids, and mixtures thereof.
5. The composition according to claim 3 , wherein the co-accelerator is selected from the group consisting of triazines, ethanolamine, diethanolamine, triethanolamine, N,N dimethyl aniline, benzene sulphanimide, cyclohexyl amine, triethyl amine, butyl amine, saccharin, N,N-diethyl-p-toluidine, N,N-dimethyl-o-toluidine, acetyl phenylhydrazine, maleic acid, and mixtures thereof.
6. The composition according to claim 1 , further comprising at least one stabilizer.
7. The composition according to claim 6 , wherein the stabilizer is selected from the group consisting of benzoquinone, naphthoquinone, anthraquinone, hydroquinone, methoxyhydroquinone, butylated hydroxy toluene, ethylene diamine tetraacetic acid or a salt thereof, and mixtures thereof.
8. The composition according to claim 1 , wherein the cure accelerator is
wherein R is hydrogen, alkyl, alkenyl, alkynl, hydroxyalkyl, hydroxyalkenyl, or hydroxyalkynl; and R 1 and R 2 are each individually selected from halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl.
9. The composition according to claim 1 , wherein the cure accelerator is selected from one or more of
wherein R, R 1 and R 2 are as defined above.
10. The composition according to claim 1 , wherein the cure accelerator is
1,2,3,4-tetrahydrobenzo-h-quinolin-3-ol.