Aluminosiloxane compound and process for preparing the same

Details Aluminosiloxane compound and process for preparing the same Aluminosiloxane compound and process for preparing the same

2001-02-14

2002-12-17

Nazario-Gonzalez, Porfirio (Department: 1621)

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

Organic compounds

Heavy metal containing

C556S173000, C252S182300

Reexamination Certificate

active

06495708

ABSTRACT:

TECHNICAL FIELD
The present invention relates to novel aluminosiloxane compounds represented by the following formulae (1) and (2), processes for preparing same and use thereof. Particularly, the compounds of formulae (1) and (2) according to the present invention have the characteristics to be prepared from waste silicone compounds and to be advantageously used as siloxylating agent for various organic and inorganic materials, specifically for materials containing hydroxy group.
in which
R is identical with or different from each other, and represents C
1
-C
6
-alkyl or phenyl,
n denotes a number of 6 to 90, and
M represents alkali metal.
BACKGROUND ART
Currently used siloxylating agents include silane or siloxane compounds containing reactive hydroxy group(—OH), alkoxy group(—OR), carboxyl group (—OCOR), amine group(—NHR, —NR
2
), epoxy group
hydrogen(—H), etc at terminal sites of the molecules, and modified silyl compounds wherein silyl groups are bound to the intramolecular side chains.
The novel aluminosiloxane compounds provided by the present invention belong to hetero metallic siloxane series(≡Si—O—M—O—Si≡) wherein a metal atom is placed between two siloxane groups. The aluminosiloxane compounds according to the present invention not only can replace the existing siloxylating, agent, but also exhibit more strong siliconic characteristics through the formation of a long chain wherein at least six(6) dialkyl(or phenyl)siloxyl units
are linked with each other. Particularly, the present compounds are expected to have a highly improved properties in reactivity for siloxylation, etc.
Many researches have been made on aluminosiloxanes. For example, aluminosilsesquioxane prepared from isopropoxyaluminum[(i-PrO)
2
Al] and trialkoxysilane is disclosed in J. Am. Chem. Soc. 1989, 111, 7288-7289 and Inorg Chem. 1999, 38, 210-211. This aluminosilsesquioxane compound is identical with the compounds of the present invention in that Al atom has a AlO
4
configuration, but different therefrom in that Si atom has a RSiO
3
configuration. Further, a method for endowing aluminum metal surface with anti-corrosion property and gloss by treating the metal surface with ethoxysilane vapour to form ═Al—O—Si≡ bond on the metal surface(see: Journal of the Electrochemical Society V.143, N.1, 1996); a method for forming ═Al—O—Si≡ structure on aluminum metal surface by treating the metal surface with alkoxysilane through a sol-gel method(see: Colloids and Surfaces A: Physicochem. Eng. Aspects 139, 299-310, 1998); a method for synthesizing phosphine ruthernium(Rh) complex by reacting isopropoxyaluminum with alkoxysilane through a sol-gel method(see: Inorg. Chem. 1997, 36, 862-866 and Chem. Mater. 1998, 10, 217-225); and a method for preparing mullite from aluminum and silicone oxide via aluminosiloxane(see: Chem. Mater, 1996, 8, 2056-2060) are disclosed. However, any of the intermediates or final products disclosed in these prior arts does not have a similar structure or property to the novel aluminosiloxane compound provided by the present invention.
Under the technical background as explained above, the present inventors have studied to develop an effective method for decomposition and recovery of siloxane bond-containing compound such as silicone rubber, silicone oil, etc., which ultimately results in decrease of pollution caused by waste silicone compounds and promotion of silicone chemical industry without any concern about waste. As a result, we filed an application for a novel process for decomposing siloxane bond-containing compound characterized in that secondary and/or tertiary aliphatic alcohols are used as a decomposition facilitator, and if desired, the decomposition product is further sonicated and treated with a terminator. The application has now been granted a patent(see, Korean Patent No 190,752, and U.S. Pat. No. 5,892,087). Specifically, the siloxane bond has the advantage of excellent weatherability whereby it is not aged nor decomposed But, such an advantage rather causes the impossibility of natural decomposition after waste of the siloxane bond-containing compounds, which makes them serious pollutional materials. Therefore, the development of said decomposition or recovery process is considered to have a great importance in the aspect of environmental protection.
The present inventors proceeded with our studies to develop a compound which can be effectively utilized as a siloxylating agent by using a siloxane alkali metal salt represented by the following formula (3), which is obtained through the aforementioned decomposition process, as the starting material. Accordingly, the present inventors have synthesized the compounds of formulae (1) and (2) as above and identified structures and uses thereof, and then completed the present invention:
in which
R is identical with or different from each other, and represents C
1
-C
6
-alkyl or phenyl,
R′ represents hydrogen or C
1
-C
6
-alkyl,
M represents alkali metal, and
m denotes a number of 3 to 6.
The present invention will be more specifically explained hereinafter.
DISCLOSURE OF INVENTION
One object of the present invention is to provide aluminosiloxane compounds of the following formula (1) or (2):
in which
R is identical with or different from each other, and represents C
1
-C
6
-alkyl or phenyl,
n denotes a number of 6 to 90, and
M represents alkali metal.
As can be seen from the above formulae (1) and (2), silicon atoms in the aluminosiloxane compound of the present invention are identified through
29
Si-NMR to have the configuration of dialkyl(or phenyl)siloxyl unit
wherein two(2) oxygen atoms and two(2) alkyl(or phenyl) groups are attached to the silicon atom, and aluminum atoms are identified through
27
Al-NMR to have the configuration coordinated with four(4) oxygen atoms.
The present compounds characterized by such an unique structure have different molecular weights depending on R, M and n. Further, with the content of M, the compound of formula (1) seems to be associated to form the compound of formula (2). That is, according to G.P.C. molecular weight measurement, the compound of formula (2) having an average molecular weight of 2000 wherein R is methyl, n is 6, and M is natrium(Sample 1 of the following Table 1) may be converted to the compound of formula (1) having an average molecular weight of 1000(Sample 2 of the following Table 1) by the treatment with ammonium chloride(purification=removal of natrium) during which the content of natrium is significantly decreased(1.51%→0.55%). Elementary analysis results and n values calculated therefrom for some typical compounds according to the present invention are represented in the following Table 1.
TABLE 1
Molecular Weight
Sample
Found
n
No
C (%)
H (%)
O (%)
Si (%)
Al (%)
Na (%)
Calculated
by GPC
Si/Al
value
1
30.75
6.27
22.88
35.84
2.76
1.51
1963.70
2,000
12
 6
2
30.82
6.28
22.89
35.8
2.85
0.55
903.27
1,000
12
 6
3
31.59
6.59
23.9
36.82
0.52
0.3
5,250.60
5,462
70
35
4
32.41
7.67
23.21
36.68
0.3
0.2
10,042.70
10,948
130 
65
As can be seen from the elementary analysis results of the above Table 1, it has been found that aluminum content is 0.52% and average molecular weight is 5,462(see
FIG. 3
) in the case of Sample 3(object compound of Example 5) and aluminum content is 0.3% and average molecular weight is 10,948 in the case of Sample 4(object compound of Example 6). If calculated from the elementary analysis results, the n value of Sample 3 is 35 and that of Sample 4 is 65, respectively. Samples 3 and 4 are prepared using different amount of powdered aluminum metal from each other(see Examples 5 and 6). Therefore, it is realized that if the amount of aluminum(starting material) is controlled in the process for preparing the aluminosiloxane compound of the present invention, the n value may be optionally controlled. Upon conducting elementary analyses on the compounds having various molecular weights including the analyses of Table 1, it is identified that 12 to 180 silicon atoms are

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