Amine compounds and curable compositions derived therefrom

Details Amine compounds and curable compositions derived therefrom Amine compounds and curable compositions derived therefrom

2001-06-29

2003-01-14

Shaver, Paul F. (Department: 1621)

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

Organic compounds

Silicon containing

C556S425000, C528S038000, C427S387000, C428S412000, C428S447000

Reexamination Certificate

active

06506921

ABSTRACT:

FIELD OF INVENTION
The present invention relates generally to amine compounds that find particular use in the sol-gel preparation of curable, high abrasion-resistant coating compositions. The present invention further relates to methods of making such amine compounds, curable compositions comprising the amine compounds, methods of curing such compositions and the cured products derived therefrom.
BACKGROUND OF THE INVENTION
High abrasion-resistant coating compositions find use in a wide variety of coatings applications. Because such compositions form coatings which tend to increase the hardness and abrasion resistance of substrates, they are desirable for use in protecting the surfaces of said substrates. For example, high abrasion resistant coating compositions are used in the manufacture of transparent articles, including building windows, aircraft windows, eyeglasses, and lenses, to prevent dulling, pitting and scratching of the surfaces thereon. Additionally, high abrasion resistant coating compositions are used to help metal substrates, such as those made from aluminum, maintain physical and structural qualities.
A useful class of such high abrasion resistant coating compositions are those derived via sol-gel procedures. Traditionally, such coating compositions have been produced by reacting one or more inorganic alkoxysilane compounds to form a curable composition comprising a network of siloxane bonded (—Si—O—Si—) moieties.
More recently, alkoxysilated amine compounds have been used in conjunction with inorganic compounds to form high abrasion resistant coating compositions via sol-gel procedures. For example, U.S. Pat. Nos. 5,316,855 and 5,371,261, issued to Wang et al., disclose the use of alkoxysilylated organic compounds containing urea (—NH—C(O)—NH—) and/or urethane (—NH—C(O)—O—) bonds in the preparation of sol-gel derived curable compositions. Such organic compositions are reacted with metal alkoxide or semi-metal alkoxide compounds to form curable compositions.
The present inventors have discovered that the use of organic compounds containing urea (—NH—C(O)—NH—) and/or urethane (—NH—C(O)—O—) bonds in curable compositions is disadvantageous for several reasons. For example, one disadvantage is that organic compounds containing urea and urethane moieties are susceptible to hydrolysis. The hydrolysis of such compounds in the water-alcohol borne sol-gel compositions leads to “dangling” side groups, which lowers the abrasion resistance of the resulting coatings. In addition, the hydrolysis raises the pH of such compositions which, in turn, shortens gelling time and reduces the shelf life of the compositions.
Recognizing these and other drawbacks of the prior art, the present inventors have perceived a need for new, stable alkoxysilated organic compouds for use in a variety of applications, especially sol-gel coatings applications. These and other objects are achieved by the present invention as described below.
SUMMARY OF THE INVENTION
The present invention is directed to a family of alkoxysilated amine compounds which find particular use in the preparation of coating compositions, especially those formed via sol-gel techniques, for use in various coatings applications. The amine compounds of the present invention overcome the disadvantages of the prior art by incorporating hydrolytically stable moieties which, when forming curable compositions, can be more readily exposed to water without risk of reduced shelf life. Moreover, the amine compounds of the present invention can be used to prepare curable compositions and coatings/films having longer shelf lives and greater abrasion resistance than those of the prior art.
According to one aspect of the present invention, provided are compounds produced by a process comprising the step of reacting an amine reactant with an epoxide reactant to form a hydrolytically stable carbon-nitrogen bond therebetween, wherein at least one of the amine or epoxide reactants comprises a terminal alkoxysiyl group. In preferred embodiments, the compounds provided by the present invention are compounds described by the formula 1 below.
wherein:
X and Y are independently hydrogen or lower alkyl, or independently X and Y are linked to form a cycloalkyl moiety;
R
10
is independently —(CR
13
R
14
)
k
—(O)
l
—(CR
15
R
16
)
m
—A;
A is independently lower alkyl or —Si(R
5
)(R
7
)OR
6
, provided at least one A is —Si(R
5
)(R
7
)OR
6
;
B is independently oxygen, —O—(CR
17
R
18
)
n
—O—, a substituted or unsubstituted cycloalkylene radical, a substituted or unsubstituted arylene radical, a substituted or unsubstituted aralkylene radical, wherein any of said cycloalkylene, arylene or aralkylene radicals may be further substituted with N, O, or S heteroatoms;
R
5
and R
7
are independently hydroxyl, lower alkyl or lower alkoxy;
R
1
, R
2
, R
3
, R
4
, R
8
, R
9
, R
11
, R
12
, R
13
, R
14
, R
15
, R
16
, R
17
R
18
are independently hydrogen, hydroxyl, lower alkyl or lower alkoxy;
a, c, e, f, h, j, l and p are independently 0 or 1;
b, d, g, i, k, m and n are independently about 0 to about 8.
Another aspect of the present invention is a family of curable compositions containing the compounds of the present invention. Accordingly, the curable compositions of the present invention comprise at least one amine produced by a process comprising the step of reacting an amine reactant with an epoxide reactant to form a hydrolytically stable carbon-nitrogen bond therebetween. In preferred embodiments, the curable compositions of the present invention comprise at least one amine compound of formula (1).
The curable compositions of the present invention are useful in the manufacture of abrasion-resistant coatings. Therefore, yet another aspect of the present invention is a method for producing a substrate having an abrasion-resistant coating comprising the steps of:
(a) applying a layer of the curable composition of the invention onto a substrate; and (b) curing the curable composition on the substrate.
The inventive method produces articles of manufacture having abrasion-resistant coatings. Therefore, still another aspect of the present invention is a substrate having an abrasion-resistant coating produced via the method of the present invention.
The curable compositions comprising amine compounds of the present invention may be cured to form films. Therefore, the present invention also includes the films produced by curing the curable compositions comprising at least one amine compound of the present invention.
DESCRIPTION OF THE INVENTION AND PREFERRED EMBODIMENTS
As employed above, and throughout the disclosure, the following terms, unless otherwise indicated, shall be understood to have the following meanings:
“Alkyl” means a straight-chain or branched aliphatic group. Preferred alkyls are those having from about 1 to about 20 carbon atoms. “Lower alkyl” is an alkyl group having from about 1 to about 6 carbon atoms and is most preferred. Examples of lower alkyl groups are methyl, ethyl, n-propyl, isopropyl, butyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, and n-hexyl.
“Alkylene” means a divalent straight-chain or branched aliphatic group. Preferred alkylenes are those having from about 1 to about 20 carbon atoms. “Lower alkylene” is an alkylene group having from about 1 to about 6 carbon atoms and is most preferred. Examples of lower alkyl groups are methylene, ethylene, n-propylene, isopropylene, butylene, sec-butylene, tert-butylene, n-pentylene, isopentylene, neopentylene, and n-hexylene.
“Alkoxy” means an aliphatic group comprising an alkyl group attached to an oxygen radical. Preferred alkoxys are those having from about 1 to about 20 carbon atoms. “Lower alkoxy” is an alkoxy group having from about 1 to about 6 carbon atoms and is most preferred. Examples of lower alkoxy groups are methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, sec-butoxy, tert-butoxy, n-pentoxy, isopentoxy, neopentoxy, and n-hexoxy.
“Alkoxysilyl” means a tri-substituted silyl group comprising at least one to about three alkoxy groups wherein any non-alkoxy substituent

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