Process for preparing silicon-containing azodicarbamides
View Patent ↗The invention relates to a process for preparing silicon-containing azodicarbamides of the general formula (I) (R 1 ) 3-a (R 2 ) a Si—R I —NH—C(O)—N═N—C(O)—NH—R I —Si(R 1 ) 3-a (R 2 ) a (I), by reaction of azobiscarboxy compounds of the general formula II R 3 —X 1 —C(O)—N═N—C(O)—X 1 —R 4 (II) with aminosilanes of the general formula III (R 1 ) 3-a (R 2 ) a Si—R I —NH 2 (III).
1. Process for producing silicon-containing azo-dicarbamides of the general formula I
(R 1 ) 3-a (R 2 ) a Si—R I —NH—C(O)—N═N—C(O)—NH—R I —Si(R 1 ) 3-a (R 2 ) a (I),
via reaction of azobiscarboxy compounds of the general formula II
R 3 —X 1 —C(O)—N═N—C(O)—X 1 —R 4 (II)
with aminosilanes of the general formula III
(R 1 ) 3-a (R 2 ) a Si—R I —NH 2 (III),
where a is mutually independently 1, 2 or 3,
R 1 are mutually independently substituted or unsubstituted Cl-C18-alkyl groups, C5-C18-cycloalkyl groups, or C6-C18-aryl groups,
R 2 are mutually independently an —OH, a substituted or unsubstituted Cl-C18-alkoxy group or a C5-C18-cycloalkoxy group,
R I is a branched or unbranched, saturated or unsaturated, aliphatic, aromatic or mixed aliphatic/aromatic divalent C 1 -C 30 -hydrocarbon group, optionally substituted with F—, Cl—, Br—, I—, —CN or HS—,
X 1 are mutually independently O, NH or N-A 1 , where
A 1 is C1-C12-alkyl group or aryl group and
R 3 and R 4 are mutually independently an H, a C1-C18-alkyl group, a benzyl group (—CH 2 —C 6 H 5 ) or an alkyl polyether group of the formula (CH 2 —CH 2 —O) n —R 5 or (CH(CH 3 )—CH 2 —O) n —R 5 , where the average of n is from 1 to 18 and
R 5 is mutually independently a branched or unbranched, saturated or unsaturated monovalent C1-C32-hydrocarbon chain.
2. Process for producing silicon-containing azocarbamides according to claim 1 , wherein the azobiscarboxy compound of the general formula II is H 2 N—C(O)—N═N—C(O)—NH 2 , R 3 —O—C(O)—N═N—C(O)—O—R 4 or R 3 —HN—C(O)—N═N—C(O)—NH—R 4 .
3. Process for producing silicon-containing azocarbamides according to claim 1 or 2 , wherein the aminosilane of the general formula III is 3-aminopropyl(trimethoxy-silane), 3-aminopropyl(triethoxysilane), 3-aminopropyl(dimethoxymethylsilane), 3-aminopropyl(methoxydimethylsilane), 3-aminopropyl(diethoxymethylsilane), 3-aminopropyl(ethoxydimethylsilane) or 3-aminopropyl(tripropoxysilane).
4. Process for producing silicon-containing azo-dicarbamides according to claim 1 , wherein the reaction is carried out in a solvent.
5. Process for producing silicon-containing azo-dicarbamides according to claim 1 , wherein the reaction is carried out with no solvent.
6. Process for producing silicon-containing azo-dicarbamides according to claim 1 , wherein the reaction is carried out with exclusion of air and/or with exclusion of water.
7. Process for producing silicon-containing azocarbamides according to claim 1 , wherein prior to, during or after the reaction stabilizers are added.
8. Process for producing silicon-containing azo-dicarbamides according to claim 2 , wherein the compound used of the general formula II is C 3 H 7 —O—C(O)—N═N—C(O)—O—C 3 H 7 or C 6 H 4 —CH 2 —O—C(O)—N═N—C(O)—O—CH 2 —C 6 H 4 .
9. Process for producing silicon-containing azo-dicarbamides according to claim 1 , wherein the reaction is carried out at temperatures from −50° C. to +200° C.