Organosilicon compounds

Details Organosilicon compounds Organosilicon compounds

2001-04-05

2003-03-11

Dawson, Robert (Department: 1712)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

At least one aryl ring which is part of a fused or bridged...

C528S038000, C528S040000, C528S043000, C556S407000, C556S413000, C556S427000, C556S431000, C544S003000, C544S007000

Reexamination Certificate

active

06531539

ABSTRACT:

CROSS REFERENCE TO RELATED APPLICATIONS
The present application claims priority to German application 100 17 654.9 filed on Apr. 8, 2000, the subject matter of which is hereby incorporated by reference.
FIELD OF THE INVENTION
The present invention relates to organosilicon compounds, a process for their preparation and their use.
BACKGROUND OF THE INVENTION
It is known that sulfur-containing organosilicon compounds, such as 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 3-thiocyanatopropyltriethoxysilane or bis-(3-triethoxysilylpropyl)tetrasulfane and -disulfane, are employed as silane adhesion promoters or reinforcing additives in rubber mixtures comprising oxidic fillers. The rubber mixtures are used, inter alia, for industrial rubber articles and for components of car tires, in particular for treads (DE 2 141 159, DE 2 212 239, U.S. Pat. No. 3,978,103, U.S. Pat. No. 4,048,206).
It is also known that the alkoxysilyl function, usually a trimethoxysilyl or triethoxysilyl group, reacts with the silanol groups of the filler, usually silica, during preparation of the mixture and the silane is thus fixed on the filler surface. The filler-rubber bond is then formed during the vulcanization process via the sulfur functionality of the fixed silane. So-called blocked mercaptosilanes have proven to be particularly effective for this use (WO99/09036). These compounds contain a polymer-reactive monosulfane function which is saturated with carbonyl-like groups. These carbonyl-like blocking groups can also be, in addition to groups such as —C(═O)R, —C(═S)R and —C(═NR′)R, heterocarbonyls, such as sulfone groups, phosphone groups and others. The essential advantage of these compounds is that premature reaction of the polymer-reactive sulfur function can be suppressed by targeted activation of this function. The production reliability of rubber articles with a silica filler content is increased significantly by these products.
In addition, it is known from the literature that triazines are very active vulcanization accelerators. When these compounds are employed, nitrosamine formation can be suppressed, which represents an important toxicological and ecotoxicological advantage of these systems (H. Westlinning, Kautschuk, Gummi, Kunststoffe 23 (1970) 219; E. Morita, A. B. Sullivan, A. Y. Coran, Rubber Chem. Technol. 58 (1985) 284). Derivatives carrying amino groups and polysulfidic groups in particular are interesting alternatives to conventional accelerators, since in addition to their positive influence on the vulcanization, they also additionally act as sulfur donors (Ullmann's Encyclopedia of Industrial Chemistry, 4th edition, vol. A23, p. 375).
A disadvantage of the known organosilicon compounds is that they do not act simultaneously as good adhesion promoters and good vulcanization accelerators, sulfur donors, crosslinking agents or anti-ageing agents.
SUMMARY OF THE INVENTION
The object of the present invention is to provide triazine-functional adhesion promoters which, in addition to their function as adhesion promoters in the vulcanization products, simultaneously also act as vulcanization accelerators, sulfur donors, crosslinking agents or anti-ageing agents.
The invention provides an organosilicon compound of the general formula I
which is characterized in that the substituents X are identical or different and X is one of the following groups A, B or C:
A=Y—R
1
—S
n
—, where
where
R
2
=alkoxy radical having 1 to 4 C atoms,
R
3
=alkyl radical having 1 to 8 C atoms,
R
1
=linear or branched hydrocarbon having 1 to 10 C atoms,
n=1-8 or mixtures thereof,
B=OR
4
, NR
5
R
6
, SR
7
, SCN or —CO—R
8
where
R
4
, R
5
, R
6
, R
7
=H, branched or unbranched alkyl radical having 1-10 C atoms or substituted or unsubstituted aromatic radical having 6-30 C atoms, which is optionally interrupted by N, S or O atoms,
R
8
=linear or branched alkyl radical having 1-20 C atoms, preferably methyl or long-chain uneven-numbered alkyl radicals C
9
-C
17
,
C=(S
m
)/2 where
m=1-8 or mixtures thereof
with the proviso that the group C bridges two triazine units; at least one group A is present in the molecule; and the combination of a group A together with two mercapto groups or a mercapto group and an amino group NR
5
R
6
is excluded.
Appropriately substituted triazine compounds can act as crosslinking agents between rubber chains and filler. In these cases at least one substituent can react with the filler and at least one substituent can react with the polymer.
Appropriate substituents can act as sulfur donors.
Appropriately substituted triazine compounds can act as crosslinking agents between various rubber chains. In these cases at least two substituents of the triazine molecule can react with different rubber chains and join the rubber chains via the rigid triazine unit.
With appropriately substituted triazine compounds, an anti-ageing agent bonded as a substituent on the triazine ring can be introduced into the rubber. Substances which can have such actions are, for example, aromatic amines and phenols (Ullmann's Encyclopedia of Industrial Chemistry, 4th edition, vol. 23, p. 383 et seq.).
It is known that the three Cl atoms in cyanuric chloride can be replaced selectively by nucleophiles (V. I. Mur, Russian Chem. Rev. 33 (1964) 92, Ullmann's Encyclopedia of Industrial Chem., 4th edition, vol. A8, p. 195 f).
The invention also provides a process for the preparation of organosilicon compounds of the formula I, which is characterized in that group A is obtained:
by reaction (II) of a chlorine-substituted triazine base skeleton with mercaptosilanes of the corresponding structure in the presence of an acid-trapping agent, for example tertiary amines, alkali metal carbonates or by blowing out the HCl gas formed, a mono- di- or trisubstitution being obtained selectively, depending on the number of chlorine atoms on the triazine skeleton and on the molar ratio of triazine:mercaptosilane, or
by reaction (III) of a metallized mercaptotriazine with a chloroalkylsilane corresponding to grouping A and, for n>1, in the presence of elemental sulfur,
where M=H, metal, for example Na, K or Li;
group B is obtained:
by reaction (IV) of a chlorine-substituted triazine skeleton with corresponding alcohols, amines, and mercaptans in the presence of an acid-trapping agent, for example a tertiary amine (in the case of reaction with an amine in the presence of an excess of the same amine), alkali metal carbonates or by blowing out the HCl gas formed
where T=OR
4
, NR
5
R
6
or SR
7
,
by reaction (V) of a chlorine-substituted triazine skeleton with corresponding metallized alcohols, amines, and mercaptans or
by alkylation (VI) of corresponding amino- and mercaptyl-substituted triazines with highly alkylating substances Z=I, Br, Cl, (SO
4
)
0.5
,O
3
S—
and group C is obtained
by reaction of a chlorine-substituted triazine with a sodium polysulfide (VII)
or a mixture of sodium sulfide (VIIIa) or sodium hydrogen sulfide (VIIIb) and sulfur
by reaction (IX) of a mercaptotriazine or of a mercaptotriazine activated by metallization (X) with sulfur dichlorides
by reaction (XI) of a mercaptotriazine with elemental sulfur at elevated temperature or
by reaction (XII) of a mercaptotriazine activated by metallization with sulfur and a chlorine-substituted triazine derivative
The sequence of the reaction is unimportant. Preferably, group C can be introduced after group A.
The present invention also provides rubber mixtures which are characterized in that they comprise rubber, filler, preferably precipitated silica, at least one organosilicon compound of the formula (I) and, optionally, further rubber auxiliary substances. Natural rubber and/or synthetic rubbers can be used as the rubber. Preferred synthetic rubbers are described, for example, in W. Hofmann, Kautschuktechnologie [Rubber Technology], Genter Verlag, Stuttgart (1980). The rubbers can be used both by themselves an

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