N,N'- and N,N',N'-substituted silylureas and process for their production

Claim 2

A N,N' or N,N',N'-substituted silylurea of the formula (I) ##STR46## where n is 0 or 1 R is C 1 -C 6 alkyl, phenyl, C 5 -C 8 cycloalkyl R 1 is --(CH 2 ) 3 --, ##STR47## R 2 , R 3 are C 1 -C 3 alkyl, terminally substituted by an amino-, thio- or cyano group, --(C 2 H 4 NH) m H where m is 2 or 3, C 3 -C 18 alkenyl, ##STR48## benzyl, pyridyl, triazyl or such a group having at least one substituent which is an amino, hydroxyl, thio, C 1 -C 3 alkoxy, nitro, or carboxyl group or a silyl group, R 2 and R 3 together with the nitrogen atom and 0, 1, or 2 further heteroatoms forms a monovalent 5 to 14 numbered saturated or unsaturated cyclic group having 2 to 12 carbon atoms, with the proviso that R 2 can also be hydrogen, C 1 -C 18 alkyl or C 3 -C 18 alkenyl.

Claim 3

A silylurea according to claim 1 wherein R 1 is ##STR49##

Claim 4

A silylurea according to claim 1 wherein at least one of R 2 and R 3 is alkenyl.

Claim 5

A silylurea according to claim 1 where ##STR50## form an imidazole, pyrazole, 1,2,3-triazole, 1,2,4-triazole, piperazine, pyrazoline, imidazolidine, morpholine, thiazolidine, indazole, azimidobenzene, benzimidazole, indole, or phenothiazine ring.

Claim 6

A silylurea according to claim 1 wherein R 2 is a C 1 -C 3 alkyl group having an amino, thio, or cyano group.

Claim 7

A silylurea according to claim 1 where R is C 1 -C 3 alkyl and n is 0.

Claim 8

A silylurea according to claim 6 wherein R 2 is alkyl of 8 to 18 carbon atoms.

Claim 9

A process of producing a compound of the formula (I) ##STR51## where n is 0 or 1 R is C 1 -C 6 alkyl, phenyl, C 5 -C 8 cycloalkyl R 1 is --(CH 2 ) 3 --, ##STR52## R 2 , R 3 are C 1 -C 18 alkyl, C 5 -C 8 cycloalkyl, C 1 -C 3 alkyl, terminally substituted by an amino-, thio- or cyano group, --(C 2 H 4 NH) m H where m is 2 or 3, C 3 -C 18 alkenyl, ##STR53## benzyl, phenyl, naphthyl, pyridyl, triazyl or such a group having at least one substituent which is an amino, hydroxyl, thio, C 1 -C 3 alkoxy, nitro, or carboxyl group or a silyl group of the formula (RO).sub.3-n (CH.sub.3).sub.n Si--R.sup.4 -- in which R 4 is C 1 -C 3 alkylene, ##STR54## or R 2 and R 3 together with the nitrogen atom and 0, 1, or 2 further heteroatoms forms a monovalent 5 to 14 numbered saturated or unsaturated cyclic group having 2 to 12 carbon atoms, with the proviso that R 2 can also be hydrogen comprising first adding to a solution of an amino compound of the formula (III) ##STR55## in an aprotic, polar, organic solvent an equimolar amount of alkali cyanate and subsequently adding an equimolar amount of a halosilane of the formula IV (RO).sub.3-n (CH.sub.3).sub.n Si--R.sup.1 --X, where R, R 1 and n are as defined above and X=Cl, Br, or I, heating to 120° to 155° C., stirring for 1 to 8 hours at 130° to 150° C., and separating the product after the reaction.

Claim 10

A process of producing a compound of the formula (I) ##STR51## where n is 0 or 1 R is C 1 -C 6 alkyl, phenyl, C 5 -C 8 cycloalkyl R 1 is --(CH 2 ) 3 --, ##STR52## R 2 , R 3 are C 1 -C 18 alkyl, C 5 -C 8 cycloalkyl, C 1 -C 3 alkyl, terminally substituted by an amino-, thio- or cyano group, --(C 2 H 4 NH) m H where m is 2 or 3, C 3 -C 18 alkenyl, ##STR53## benzyl, phenyl, naphthyl, pyridyl, triazyl or such a group having at least one substituent which is an amino, hydroxyl, thio, C 1 -C 3 alkoxy, nitro, or carboxyl group or a silyl group of the formula (RO).sub.3-n (CH.sub.3).sub.n Si--R.sup.4 -- in which R 4 is C 1 -C 3 alkylene, ##STR54## or R 2 and R 3 together with the nitrogen atom and 0, 1, or 2 further heteroatoms forms a monovalent 5 to 14 numbered saturated or unsaturated cyclic group having 2 to 12 carbon atoms, with the proviso that R 2 can also be hydrogen comprising first adding to a solution of an amino compound of the formula (III) ##STR55## in an aprotic, polar, organic solvent an equimolar amount of alkali cyanate and subsequently adding an equimolar amount of a halosilane of the formula IV (RO).sub.3-n (CH.sub.3).sub.n Si--R.sup.1 --X, where R, R 1 and n are as defined above and X=Cl, Br, or I, heating to 120° to 155° C., stirring for 1 to 8 hours at 130° to 150° C., and separating the product after the reaction.

Claim 11

A process according to claim 8 wherein the reaction is carried out at 140° C. for 4 hours.

Claim 12

A process according to claim 8 wherein 0.75 mole of trismethoxysilyl-3-chloropropane is reacted with 0.75 mole of ethylenediamine and 0.75 mole of potassium cyanate in 200 ml of dimethylformamide at 140° C. for 4 hours.

Claim 13

A process according to claim 8 wherein the solvent is dimethylformamide or dimethylsulfoxide.

Claim 14

A compound according to claim 1 wherein R 2 is hydrogen or C 1 -C 18 alkyl.

Claim 15

A compound according to claim 1 having the formula: ##STR56## where R 2 is H or C 1 -C 18 -alkyl.

Claim 16

A compound according to claim 13 wherein R 2 is hydrogen.

Claim 17

A compound according to claim 13 wherein R 2 is C 1 -C 18 -alkyl.