3-methacryloxy- and 3-acryloxyisobutylalkoxysilanes

Details 3-methacryloxy- and 3-acryloxyisobutylalkoxysilanes 3-methacryloxy- and 3-acryloxyisobutylalkoxysilanes

1999-11-24

2003-08-19

Shaver, Paul F. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Silicon containing

C524S859000, C524S860000, C524S866000

Reexamination Certificate

active

06608225

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel 3-organo-2-methylpropylalkoxysilanes. Such compounds are also referred to as 3-organoisobutylalkoxysilanes.
The present invention also relates to processes for the preparation of 3-organo-2-methylpropylalkoxysilanes and to their use.
2. Discussion of the Background
Most organofunctional alkoxysilanes have specific technical applications. Some are used as intermediates.
For example, 3-aminopropyltrialkoxysilanes, 3-aminopropylmethyldialkoxysilanes, N-aminoethyl-3-aminopropyltrimethoxy-silane, N-aminoethyl-3-aminopropyl-methyldimethoxysilane, 3-mercaptopropyltrimethoxysilane and 3-methacryloxypropyltrimethoxysilane are used as adhesion promoters between inorganic materials and organic polymers, as crosslinking agents or as surface modification agents. Compounds such as 3-aminoisobutyltrialkoxysilanes, 3-aminoisobutylmethyldialkoxysilanes, N-(2-aminoethyl)-3-amino-2-methylpropylalkoxysilanes and N-(2-aminoethyl) 3-amino-2-methylpropylmethyldialkoxysilanes are also known (EP 0 676 403 A1, German Patent 11 58 071, DE-B 11 52 695).
It is also known that reactions of 3-chloropropyltrimethoxysilanes with potassium methacrylate in the presence of a phase transfer catalyst give 3-methacrylpropyltrimethoxyslane (EP 0 483 480 B1, EP 0 437 653 B1, DE-A 44 37 667).
There is a need for novel 3-organoisobutylalkoxysilanes.
SUMMARY OF THE INVENTION
The present invention provides 3-methacryloxy- and 3-acryloxyisobutylalkoxysilanes of the general formula (I)
and
R is a linear alkyl radical having from 1 to 4 carbon atoms,
R
1
is a linear or branched alkyl radical having from 1 to 3 carbon atoms, and
m is 0 or 1.
DETAILED DESCRIPTION OF THE INVENTION
The present inventors have found that reacting a 3-chloro-2-methylpropyltrialkoxysilane or a 3-chloro-2-methylpropylmethyldiethylalkoxysilane with potassium methacrylate or potassium acrylate in the presence of a phase transfer catalyst, such as is disclosed in DE-A 44 37 667, European Patent 0 483 480 and EP-A 0 437 653, gives 3-methacryloxy- or 3-acryloxyisobutylalkoxysilanes of the general formula (I) with high selectivity.
The present invention thus provides a process for the preparation of 3-methacryloxy- or 3-acryloxyisobutylalkoxysilanes of the general formula (I) by reacting alkali metal methacrylate or alkali metal acrylate, preferably potassium methacrylate or potassium acrylate, with 3-chloroisobutylalkoxysilane of the general formula (II),
where R, R
1
and m are as defined above,
in the presence of at least one phase transfer catalyst and optionally in the presence of at least one stabilizer, and working up the product mixture.
In the process according to the invention, the 3-chloroisobutylalkoxysilane is preferably 3-chloroisobutyltrimethoxysilane, 3-chloroisobutyltriethoxysilane, 3-chloroisobutylmethyldimethoxysilane or 3-chloro-isobutylmethyldiethoxysilane.
The present “phase transfer process” is generally carried out as already disclosed by EP 0 483 480 B1, EP 0 437 653 B1 and DE-A 44 37 667. EP 0 483 480 B1, EP 0 437 653 B1 and DE-A 44 37 667, and the contents of their respective applications, are incorporated by reference herein in their entireties.
The phase transfer catalyst can be, e.g., tetrabutylammonium bromide.
The novel compounds of the general formula (I) have a general tendency to polymerize at elevated temperature or under the influence of UV light. The addition of one or more stabilizers can stabilize the compounds according to the invention in a suitable manner both during the synthesis and also afterward. Such stabilizers are disclosed in DE-A 44 37 666, DE-A 44 37 667, U.S. Pat. No. 5,103,032, EP-A 0 620 206, EP-A 0 472 438, EP-A 0 520 477. Examples of stabilizers include: benzoquinones; hydroquinones, such as 2,5-di-t-butylhydroquinone; monoalkyl ethers of hydroquinones; amides of organic acids; isocyanurates; organofunctional and sterically hindered phenols, such as 4-(2-aminoethyl) phenol, 4-(N, N-dimethylaminomethyl)-2,6-di-t-butylphenol, 4-(N, N-dibutylaminomethyl)-2,6-di-t-butylphenol, tetrakis[methylene-3-(3′,5′-di-t-butyl-4-hydroxyphenyl) propionate]methane, 2-t-butyl-6-(3′-t-butyl-5′-methyl-2-hydroxybenzyl)-4-methylphenyl acrylate, 4,4′-butylidenebis(2-t-butyl-5-methylphenol), 2,2′-butylidenebis(6-t-butyl4-methylphenol), 2,2′-ethylidene-bis(4,6-dibutylphenol), 2,2′-methylenebis(4-methyl-t-butylphenol),4,4′-methylenebis(2,6-di-t-butylphenol), n-octadecyl-3-(3′,5′-di-t-butyl4′-hydroxyphenyl)propionate, 2-t-butyl-4-methoxyphenol, 2,4-di-methyl-6-t-butylphenol, 2,6-di-t-butylphenol, 2,6-di-t-butyl-4-methylphenol, 2,6-di-t-butyl-4-(&agr;-dimethyl)aminomethylphenol, 2,6-di-butyl-4-ethylphenol, 2,6-di-t-butyl-4-methoxyphenol and (mono-, di-, tri-)&agr;-methylbenzylphenols; alkylamines, such as propylamine, 2,2,6,6-tetramethylpiperidinooxyl and 4-hydroxy-2,2,6,6-tetramethylpiperidinooxyl; aromatic amines and N-substituted imines, such as N,N′-diphenyl-p-phenylenediamine, N,N′-dinaphthyl-p-phenylenediamine, N,N′-di(1-methylheptyl)-p-phenylenediamine, N,N′-di(1-ethyl-3-methylpentyl)-p-phenylenediamine, N,N′-di(1,4-dimethylpentyl)-p-phenylenediamine, N,N′-di-sec-butyl-p-phenylenediamine, N-phenyl-N′-cyclohexyl-p-phenylenediamine, N-phenyl-N′-isopropyl-p-phenylenediamine, 4,4′-dioctyldiphenylamine, N-methylbis(3,5-di-t-butyl4-hydroxybenzyl)amine, N,N′-diphenyl-p-quinonediimine, N,N′-di(1-methylheptyl )-p-quinonediimine, N,N′-di(1-ethyl-3-methyl-pentyl)-p-quinonediimine, N,N′-di(1,4-dimethylpentyl)-p-quinonediimine, N,N′-di-sec-butyl-p-quinonediimine, N-phenyl-N′-cyclohexyl-p-quinonediimine, and N-phenyl-N-isopropylquinonediimine; and phenothiazines, such as bis(a-methylbenzyiphenothiazine, 3,7-dioctylphenothiazine, and bis(&agr;-dimethylbenzyl)phenothiazine.
Novel 3-methacryloxy- or 3-acryloxyisobutylalkoxysilanes of the general formula (I) already given above can be used, in particular, as adhesion promoters in filled polymers, as adhesion promoters in glass-fiber-reinforced plastics and inorganically filled organic polymers, as components for the coating of mineral wool, as components in scratch-resistant coatings, for example in the copolymerization with methyl methacrylate (MMA) in surface coatings, and as adhesion promoters in artificial stone, artificial stone slabs and artificial stone moldings, for example for sanitary articles.
The present-invention thus provides for the use of 3-methacryloxy- or 3-acryloxyisobutylalkoxysilanes of the general formula (I) already given above as adhesion promoters, as coating materials, as components in surface coatings, artificial stone and scratch-resistant coatings and also for modifying surface properties.
The present invention is illustrated in more detail by the examples below:


REFERENCES:
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patent: 5103032 (1992-04-01), Turner et al.
patent: 5117027 (1992-05-01), Bernhardt et al.
patent: 5145979 (1992-09-01), Takatsuna et al.
patent: 5646325 (1997-07-01), Monkiewicz et al.
patent: 5789611 (1998-08-01), Isoyama et al.
patent: 1 152 695 (1963-08-01), None
patent: 1 158 071 (1963-11-01), None
patent: 44 37 666 (1996-04-01), None
patent: 44 37 667 (1996-04-01), None
patent: 0 437 653 (1991-07-01), None
patent: 0 472 438 (1992-02-01), None
patent: 0 483 480 (1992-05-01), None
patent: 0 520 477 (1992-12-01), None
patent: 0 620 206 (1994-10-01), None
patent: 0 676 403 (1995-10-01), None

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