Mercaptosilanes and derivatives thereof
View Patent ↗Mercaptosilanes are disclosed of the formula I wherein R 1 is an alkyl polyether group —O—(R 5 —O) m —R 6 . They are prepared by a procedure in which a silane of the formula II is subjected to a catalyzed reaction with an alkyl polyether R 1 —H, R 7 —OH being split off, the molar ratio of the alkyl polyethers R 1 —H to the silane of the formula II is at least 0.5 and R 7 —OH is separated off from the reaction mixture continuously or discontinuously. They can be used in shaped articles.
1. A composition comprising a mixture of mercaptosilanes of formula I,
wherein R 1 is an alkyl polyether group —O—(R 5 —O) m —R 6 , where R 5 is identical or different and is a branched or unbranched, saturated or unsaturated, aliphatic divalent C1-C30 hydrocarbon group, m is on average 5, and R 6 comprises at least 11 C atoms and is an unsubstituted or substituted, branched or unbranched monovalent alkyl, alkenyl, aryl or aralkyl group, and
wherein one R 2 is an ethoxy group and the other R 2 is an R 1 , C1-C12 alkyl, or R 7 O group,
where R 7 is H, ethyl, propyl, a C9-C30 branched or unbranched monovalent alkyl, alkenyl, aryl or aralkyl group or (R 8 ) 3 Si group,
where R 8 is a C1-C30 branched or unbranched, alkyl or alkenyl group,
R 3 is a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic divalent C1-C30 hydrocarbon group, and
R 4 is H, CN or (C═O)—R 9 , where R 9 is a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic monovalent C1-C30 hydrocarbon group.
2. The composition according to claim 1 wherein R 1 has a molecular weight distribution.
3. The composition according to claim 1 , wherein R 6 is C 13 H 27 .
4. The composition according to claim 1 and further comprising
and/or hydrolysis and/or condensation products thereof.
5. The composition according to claim 1 , wherein both R 2 's are ethoxy groups.
6. The composition according to claim 1 , wherein the other R 2 is R 1 :
7. The composition according to claim 6 , wherein R 1 is a member selected form the group consisting of
—O—(C 2 H 4 —O) 5 —C 11 H 23 , —O—(C 2 H 4 —O) 5 —C 12 H 25 , —O—(C 2 H 4 —O) 5 —C 13 H 27 , —O—(C 2 H 4 —O) 5 —C 14 H 29 , —O—(C 2 H 4 —O) 5 —C 15 H 31 , —O—(C 2 H 4 —O) 3 —C 13 H 27 , —O—(C 2 H 4 —O) 4 —C 13 H 27 , —O—(C 2 H 4 —O) 6 —C 13 H 27 , —O—(C 2 H 4 —O) 7 —C 13 H 27 , —O—(CH 2 CH 2 —O) 5 —(CH 2 ) 10 CH 3 , —O—(CH 2 CH 2 —O) 5 —(CH 2 ) 11 CH 3 , —O—(CH 2 CH 2 —O) 5 —(CH 2 ) 12 CH 3 , —O—(CH 2 CH 2 —O) 5 —(CH 2 ) 13 CH 3 , —O—(CH 2 CH 2 —O) 5 —(CH 2 ) 14 —CH 3 , —O—(CH 2 CH 2 —O) 3 —(CH 2 ) 12 CH 3 , —O—(CH 2 CH 2 —O) 4 —(CH 2 ) 12 CH 3 , —O—(CH 2 CH 2 —O) 6 —(CH 2 ) 12 CH 3 , —O—(CH 2 CH 2 —O) 7 —(CH 2 ) 12 CH 3 ,
8. An inert organic or inorganic support having absorbed therein a composition according to claim 1 .
9. An organic or inorganic support having been pre-reacted with the composition according to claim 1 .
10. A rubber composition comprising:
(A) a rubber or a mixture of rubbers,
(B) a filler, and
(C) the composition according to claim 1 .
11. A process for the preparation of a rubber composition comprising mixing rubber or a mixture of rubbers, a filler, optionally further rubber auxiliaries and the composition according to claim 1 in a mixing unit.
12. A process for the preparation of a rubber composition comprising mixing rubber or a mixture of rubbers, a filler, thiuram sulfide and/or carbamate accelerator and/or the corresponding zinc salts, a nitrogen-containing co-activator, optionally further rubber auxiliaries and optionally further accelerators, and the weight ratio of accelerator to nitrogen-containing co-activator is equal to or greater than 1 and the composition according to claim 1 in a mixing unit.
13. A shaped article containing the composition according to claim 1 .
14. The shaped article according to claim 13 which is a pneumatic tire, tire tread, cable sheathing, hose, drive belt, conveyor belt, roller covering, tire, shoe sole, sealing ring or damping element.
15. The support according to claim 8 which is silica.
16. The support according to claim 9 which is silica.
17. A tire made from the rubber composition of claim 10 wherein the filler and the silane are present as a reaction product.
18. The composition according to claim 1 wherein one of the mercaptosilanes in the mixture is represented by the formula: