Urea-containing mercaptosilanes, process for preparation thereof and use thereof
View Patent ↗The invention relates to urea-containing mercaptosilanes of the formula I which are prepared by reacting a halosilane of the formula II with compounds of the formula III in an alcohol.
1. A urea-containing mercaptosilane of formula I
where each R 1 is independently selected from the group consisting of a C1-C10 alkoxy group, a C2-C10 cyclic dialkoxy group, a phenoxy group, a C4-C10 cycloalkoxy group, a C6-C20 aryl group, a C1-C10 alkyl group, a C2-C20 alkenyl group, a C7-C20 aralkyl group or a halogen, R 2 is a monovalent C1-C20 hydrocarbon group and each R is independently a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic divalent C1-C30 hydrocarbon group.
2. The urea-containing mercaptosilane according to claim 1 , wherein the urea-containing mercaptosilane is
(CH 3 CH 2 O) 3 Si—CH 2 —NH—CO—NH—CH 2 —S—C(O)—CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 —S—C(O)—CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 —NH—CO—NH—CH 2 CH 2 —S—C(O)—CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 —S—C(O)—CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 —S—C(O)—CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 —S—C(O)—CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 —S—C(O)—CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 —S—C(O)—CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 —S—C(O)—CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 —NH—CO—NH—CH 2 —S—C(O)—(CH 2 ) 6 CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 —S—C(O)—(CH 2 ) 6 CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 —NH—CO—NH—CH 2 CH 2 —S—C(O)—(CH 2 ) 6 CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 —S—C(O)—(CH 2 ) 6 CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 —S—C(O)—(CH 2 ) 6 CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 —S—C(O)—(CH 2 ) 6 CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 —S—C(O)—(CH 2 ) 6 CH 3 ,
(CH 3 CH 2 O) 3 Si—CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 —S—C(O)—(CH 2 ) 6 CH 3 or
(CH 3 CH 2 O) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 CH 2 —S—C(O)—(CH 2 ) 6 CH 3 .
3. The urea-containing mercaptosilane according to claim 1 , wherein the urea-containing mercaptosilane is
(EtO) 3 Si—CH 2 CH 2 CH 2 —NH—CO—NH—CH 2 CH 2 —S—C(O)—CH 3 .
4. A process for preparing the urea-containing mercaptosilane of claim 1 , comprising reacting in an alcohol a halosilane of formula II
with a compound of formula III
where R 1 , R 2 and R are each as defined in claim 1 , Hal is F, Cl, Br or I and M is an alkali metal.
5. The process of claim 4 , wherein the reaction is conducted under a protective gas atmosphere.
6. The process of claim 4 , wherein the reaction is conducted at temperatures between 0° C. and 150° C.
7. The process of claim 4 , wherein the alcohol is ethanol.
8. The process of claim 4 , wherein the halosilane of formula II is prepared by adding a base to a hydrochloride salt of an amine of formula IV
and an isocyanatosilane of formula V
where Hal, R 1 and R are each as defined in claim 4 .
9. The process of claim 8 , wherein the base is NaOEt.
10. The process of claim 4 , wherein the halosilane of formula II is prepared from an isocyanate-halogen compound of formula VI
and an aminosilane of formula VII
where Hal, R and R 1 are each as defined in claim 4 .
11. The process of claim 10 , wherein the reaction is conducted in ethanol.
12. The process of claim 4 , wherein the ethanol is distilled off.
13. The process of Process for preparing urea-containing mercaptosilane of the formula I according to claim 12 , wherein a product obtained from the reaction is dried.