Carbamate silicon compounds as latent coupling agents and process for preparation and use

Claim 2

A tert-alkyl carbamate silicon compound having the following unit structure: ##STR8## wherein R 3 contains 1 to 10 carbon atoms and represent a saturated or unsaturated aliphatic group or an aryl group with the proviso that the R 3 groups need not be the same and contain at least one alkyl group having an alpha-carbon with at least one hydrogen, and wherein the remainder of the molecule contains at least one silicon atom and from 1 to 90 carbon atoms, wherein the unit structure is attached to the silicon atom through a carbon linkage, and wherein the tert-alkyl carbamate silicon compound can also contain one or more of nitrogen, oxygen or halogen.

Claim 3

A tert-alkyl carbamate silicon compound selected from the group consisting of ##STR9## wherein: R contains 1 to 20 carbon atoms and represents an arylene group, an alkarylene group or a branched or straight chain, unsaturated or saturated group of the structure: --(CH.sub.2).sub.x --(CHR.sup.5).sub.y --(CR.sub.2.sup.5).sub.z --(V) wherein x, y, and z have a value of from 0 to 20 and wherein the sum of x, y, and z is at least 1, but not greater than 20 and wherein R 5 is an alkyl group of 1 to 6 carbon atoms, R 1 contains 1 to 10 carbon atoms, and represents a straight or branched chain alkyl group, an aryl group, or an alkaryl group; R 2 is the same as R 1 and may additionally represent hydrogen, acyl, alkoxyalkyl, CH 3 OCH 2 CH 2 --, CH 3 OCH(CH 3 )CH 2 --, N═C(R')(R") wherein R' and R" are lower alkyl, and silyl groups including the hydrolytic conensation products thereof; R 3 contains 1 to 10 carbon atoms, and represents a saturated or unsaturated aliphatic group or an aryl group with the proviso that the R 3 groups need not be the same and the formula (I) must contain at least one R 3 alkyl group and which contains an alpha-carbon with at least one hydrogen; R 4 represents hydrogen, aryl, or a straight or branched chain alkyl group of 1 to 10 carbon atoms, or --R--Si--(R.sub.(3-a).sup.1 (OR.sup.2).sub.a wherein R, R 1 and R 2 are as previously indicated; n has a value of 1 to 10, b has a value of 2 to 5 and a has a value of 1,2 or 3.

Claim 4

A tert-alkyl carbamate silicon compound selected from the group consisting of ##STR9## wherein: R contains 1 to 20 carbon atoms and represents an arylene group, an alkarylene group or a branched or straight chain, unsaturated or saturated group of the structure: --(CH.sub.2).sub.x --(CHR.sup.5).sub.y --(CR.sub.2.sup.5).sub.z --(V) wherein x, y, and z have a value of from 0 to 20 and wherein the sum of x, y, and z is at least 1, but not greater than 20 and wherein R 5 is an alkyl group of 1 to 6 carbon atoms, R 1 contains 1 to 10 carbon atoms, and represents a straight or branched chain alkyl group, an aryl group, or an alkaryl group; R 2 is the same as R 1 and may additionally represent hydrogen, acyl, alkoxyalkyl, CH 3 OCH 2 CH 2 --, CH 3 OCH(CH 3 )CH 2 --, N═C(R')(R") wherein R' and R" are lower alkyl, and silyl groups including the hydrolytic conensation products thereof; R 3 contains 1 to 10 carbon atoms, and represents a saturated or unsaturated aliphatic group or an aryl group with the proviso that the R 3 groups need not be the same and the formula (I) must contain at least one R 3 alkyl group and which contains an alpha-carbon with at least one hydrogen; R 4 represents hydrogen, aryl, or a straight or branched chain alkyl group of 1 to 10 carbon atoms, or --R--Si--(R.sub.(3-a).sup.1 (OR.sup.2).sub.a wherein R, R 1 and R 2 are as previously indicated; n has a value of 1 to 10, b has a value of 2 to 5 and a has a value of 1,2 or 3.

Claim 5

A tert-alkyl carbamate silicon compound of the formula: ##STR10## wherein: R-R 4 , and a are as indicated in claim 2.

Claim 6

A tert-alkyl carbamate silicon compound of the formula: ##STR11## wherein: R-R 4 , n and a are as indicated in claim 2.

Claim 7

The compound of claim 2 wherein R is alkylene, R 1 -R 3 are alkyl, R 4 is hydrogen and a is 3.

Claim 8

The compound of claim 2 wherein R is alkylene, R 1 -R 3 are alkyl, R 4 is hydrogen and a is 2.

Claim 9

The compound of claim 2 wherein R is alkylene, R 1 -R 3 are alkyl, R 4 is hydrogen and a is 1.

Claim 10

The compound of claim 2 wherein R is alkylene and contains at least 3 carbon atoms.

Claim 11

The compound of claim 2 wherein at least one R 3 group contains an alpha-carbon atom with at least one hydrogen.

Claim 12

The compound of claim 2 wherein R 2 and R 3 are lower alkyl and a is 3.

Claim 13

The compound of claim 2 which is tert-butyl N-(3-trimethoxysilylpropyl) carbamate.

Claim 14

The compound of claim 2 which is tert-butyl N-(3-triethoxysilylpropyl) carbamate.

Claim 15

The compound of claim 2 which is tert-butyl N-methyl-N-(3-trimethoxysilylpropyl) carbamate.

Claim 16

The compound of claim 2 which is di-(tert-butyl carbamate) of 3-[N-(2-aminoethyl)]aminopropyltrimethoxysilane

Claim 17

The compound of claim 2 which is tert-amyl-N-(trimethoxysilylpropyl) carbamate.

Claim 18

The compound of claim 2 which is tert-butyl N,N-bis(trimethoxysilylpropyl) carbamate.

Claim 19

The compound of claim 2 which is 2-(2-methyl-3-butenyl) N-(3-trimethoxysilylpropyl) carbamate.

Claim 20

A process for preparing a compound of the formula: ##STR12## wherein: R contains 1 to 20 carbon atoms and represents an arylene group, an alkarylene group or a branched or straight chain, unsaturated or saturated group of the structure: --(CH.sub.2).sub.x --(CHR.sup.5).sub.y --(CR.sub.2.sup.5).sub.z --(V) wherein x, y, and z have a value of from 0 to 20 and wherein the sum of x, y, and z is at least 1, but not greater than 20 and wherein R 5 is an alkyl group of 1 to 6 carbon atoms, R 1 contains 1 to 10 carbon atoms, and represents a straight or branched chain alkyl group, an aryl group, or an alkaryl group; R 2 is the same as R 1 and may additionally represent hydrogen, acyl, alkoxyalkyl, CH 3 OCH 2 CH 2 --, CH 3 OCH(CH 3 )CH 2 --, N═C(R')(R") wherein R' and R" are lower alkyl, and silyl groups including the hydrolytic conensation products thereof; R 3 contains 1 to 10 carbon atoms, and represents a saturated or unsaturated aliphatic group or an aryl group with the proviso that the R 3 groups need not be the same and the formula (I) must contain at least one alkyl group R 3 which contains an alpha-carbon with at least one hydrogen; wherein a has a value of 1, 2 or 3, which comprises reacting a compound of the formula: ##STR13## with a compound of the formula: OCNR--Si(R.sub.(3-a).sup.1)(OR.sup.2).sub.a wherein R-R 3 are as indicated and thereafter recovering said carbamate.

Claim 21

A process for preparing a compound of the formula: ##STR12## wherein: R contains 1 to 20 carbon atoms and represents an arylene group, an alkarylene group or a branched or straight chain, unsaturated or saturated group of the structure: --(CH.sub.2).sub.x --(CHR.sup.5).sub.y --(CR.sub.2.sup.5).sub.z --(V) wherein x, y, and z have a value of from 0 to 20 and wherein the sum of x, y, and z is at least 1, but not greater than 20 and wherein R 5 is an alkyl group of 1 to 6 carbon atoms, R 1 contains 1 to 10 carbon atoms, and represents a straight or branched chain alkyl group, an aryl group, or an alkaryl group; R 2 is the same as R 1 and may additionally represent hydrogen, acyl, alkoxyalkyl, CH 3 OCH 2 CH 2 --, CH 3 OCH(CH 3 )CH 2 --, N═C(R')(R") wherein R' and R" are lower alkyl, and silyl groups including the hydrolytic conensation products thereof; R 3 contains 1 to 10 carbon atoms, and represents a saturated or unsaturated aliphatic group or an aryl group with the proviso that the R 3 groups need not be the same and the formula (I) must contain at least one alkyl group R 3 which contains an alpha-carbon with at least one hydrogen; wherein a has a value of 1, 2 or 3, which comprises reacting a compound of the formula: ##STR13## with a compound of the formula: OCNR--Si(R.sub.(3-a).sup.1)(OR.sup.2).sub.a wherein R-R 3 are as indicated and thereafter recovering said carbamate.

Claim 22

The process of claim 18 wherein R is alkylene, R 1 -R 3 are alkyl and a is 3.

Claim 23

The process of claim 18 wherein R is alkylene, R 1 -R 3 are alkyl and a is 2.

Claim 24

The process of claim 18 wherein R is alkylene, R 1 -R 3 are alkyl and a is 1.

Claim 25

The process of claim 18 wherein R is alkylene and contains at least 3 carbon atoms.

Claim 26

The process of claim 18 wherein at least one R 3 group contains an alpha-carbon atom with at least one hydrogen.

Claim 27

The process of claim 18 wherein R 2 and R 3 are lower alkyl and a is 3.

Claim 28

The process of claim 18 which is tert-butyl N-(3-trimethoxysilylpropyl) carbamate.

Claim 29

A process for preparing a compound selected from the group consisting of: ##STR14## wherein: R contains 1 to 20 carbon atoms and represents an arylene group, an alkarylene group or a branched or straight chain, unsaturated or saturated group of the structure: --(CH.sub.2).sub.x --(CHR.sup.5).sub.y --(CH.sub.2.sup.5).sub.z --(V) wherein x, y, and z have a value of from 0 to 20 and wherein the sum of x, y, and z is at least 1, but not greater than 20 and wherein R 5 is an alkyl group of 1 to 6 carbon atoms, R 1 contains 1 to 10 carbon atoms, and represents a straight or branched chain alkyl group, an aryl group, or an alkaryl group; R 2 is the same as R 1 and may additionally represent hydrogen, acyl, alkoxyalkyl, CH 3 OCH 2 CH 2 --, CH 3 OCH(CH 3 )CH 2 --, N═C(R')(R") wherein R' and R" are lower alkyl, and silyl groups including the hydrolytic condensation products thereof; R 3 contains 1 to 10 carbon atoms, and represents a saturated or unsaturated aliphatic or aryl group with the proviso that the R 3 groups need not be the same and the formula (I) must contain at least one alkyl group R 3 which contains an alpha-carbon with at least one hydrogen; R 4 represents hydrogen, aryl, or a straight or branched chain alkyl group of 1 to 10 carbon atoms, or --R--Si--(R.sub.(3-a).sup.1)(OR.sup.2).sub.a wherein R, R 1 and R 2 are as previously indicated n has a value of from 1 to 10, b has a value of 2 to 5 and a has a value of 1, 2 or 3; which comprises reacting a compound selected from the group consisting of: ##STR15## with a compound of the formula: HSi(R.sub.(3-a).sup.1)(OR.sup.2).sub.a wherein R 1 -R 4 are as indicated, and R 6 contains 1 to 18 carbon atoms and represents an arylene group, and alkenylene group or a branched or straight chain unsaturated or saturated group and thereafter recovering said carbamate.

Claim 30

A process for preparing a compound selected from the group consisting of: ##STR14## wherein: R contains 1 to 20 carbon atoms and represents an arylene group, an alkarylene group or a branched or straight chain, unsaturated or saturated group of the structure: --(CH.sub.2).sub.x --(CHR.sup.5).sub.y --(CH.sub.2.sup.5).sub.z --(V) wherein x, y, and z have a value of from 0 to 20 and wherein the sum of x, y, and z is at least 1, but not greater than 20 and wherein R 5 is an alkyl group of 1 to 6 carbon atoms, R 1 contains 1 to 10 carbon atoms, and represents a straight or branched chain alkyl group, an aryl group, or an alkaryl group; R 2 is the same as R 1 and may additionally represent hydrogen, acyl, alkoxyalkyl, CH 3 OCH 2 CH 2 --, CH 3 OCH(CH 3 )CH 2 --, N═C(R')(R") wherein R' and R" are lower alkyl, and silyl groups including the hydrolytic condensation products thereof; R 3 contains 1 to 10 carbon atoms, and represents a saturated or unsaturated aliphatic or aryl group with the proviso that the R 3 groups need not be the same and the formula (I) must contain at least one alkyl group R 3 which contains an alpha-carbon with at least one hydrogen; R 4 represents hydrogen, aryl, or a straight or branched chain alkyl group of 1 to 10 carbon atoms, or --R--Si--(R.sub.(3-a).sup.1)(OR.sup.2).sub.a wherein R, R 1 and R 2 are as previously indicated n has a value of from 1 to 10, b has a value of 2 to 5 and a has a value of 1, 2 or 3; which comprises reacting a compound selected from the group consisting of: ##STR15## with a compound of the formula: HSi(R.sub.(3-a).sup.1)(OR.sup.2).sub.a wherein R 1 -R 4 are as indicated, and R 6 contains 1 to 18 carbon atoms and represents an arylene group, and alkenylene group or a branched or straight chain unsaturated or saturated group and thereafter recovering said carbamate.

Claim 31

The process of claim 26 wherein R is alkylene, R 1 -R 3 are alkyl, R 4 is hydrogen and a is 3.

Claim 32

The process of claim 26 wherein R is alkylene, R 1 -R 3 are alkyl, R 4 is hydrogen and a is 2.

Claim 33

The process of claim 26 wherein R is alkylene, R 1 -R 3 are alkyl, R 4 is hydrogen and a is 1.

Claim 34

The process of claim 26 wherein R is alkylene and contains at least 3 carbon atoms.

Claim 35

The process of claim 26 wherein at least one R 3 group contains an alpha-carbon atom with at least one hydrogen.

Claim 36

The process of claim 26 wherein R 2 and R 3 are lower alkyl and a is 3.

Claim 37

The process of claim 26 which is tert-butyl N-(3-trimethoxysilylpropyl) carbamate.

Claim 38

A process for preparing a carbamate compound selected from the group consisting of: ##STR16## wherein: R contains 1 to 20 carbon atoms and represents an arylene group, an alkarylene group or a branched or straight chain, unsaturated or saturated group of the structure: --(CH.sub.2).sub.x --(CHR.sup.5).sub.y --(CH.sub.2.sup.5).sub.z --(V) wherein x, y, and z have a value of from 0 to 20 and wherein the sum of x, y, and z is at least 1, but not greater than 20 and wherein R 5 is an alkyl group of 1 to 6 carbon atoms, R 1 contains 1 to 10 carbon atoms, and represents a straight or branched chain alkyl group, an aryl group, or an alkaryl group; R 2 is the same as R 1 and may additionally represent hydrogen, acyl, alkoxyalkyl, CH 3 OCH 2 CH 2 --, CH 3 OCH(CH 3 )CH 2 --, N═C(R')(R") wherein R' and R" are lower alkyl, and silyl groups including the hydrolytic conensation products thereof; R 3 contains 1 to 10 carbon atoms, and represents a saturated or unsaturated aliphatic or aryl group with the proviso that the R 3 groups need not be the same and the formula (I) must contain at least one alkyl group R 3 which contains an alpha-carbon with at least one hydrogen; R 4 represents hydrogen, aryl, or a straight or branched chain alkyl group of 1 to 10 carbon atoms, or --R--Si--(R.sub.(3-a).sup.1)(OR.sup.2).sub.a wherein R, R 1 and R 2 are as previously indicated n has a value of from 1 to 10, b has a value of from 2 to 5 and a has a value of 1, 2 or 3. which comprises reacting a compound selected from the group consisting of: HN(R.sup.4)RSi(R.sup.1).sub.(3-a))(OR.sup.2).sub.a and HN(R.sup.4)(C.sub.b H.sub.2b NH)RSi(R.sup.1).sub.(3-a))(OR.sup.2).sub.a with a compound of the formula: ##STR17## wherein x, n, a, R-R 4 are as indicated and X represents Cl, Br, I, or the groups --O--C 6 H 5 , --OC(R 3 ) 3 , or ##STR18## and thereafter recovering said carbamate.

Claim 39

A process for preparing a carbamate compound selected from the group consisting of: ##STR16## wherein: R contains 1 to 20 carbon atoms and represents an arylene group, an alkarylene group or a branched or straight chain, unsaturated or saturated group of the structure: --(CH.sub.2).sub.x --(CHR.sup.5).sub.y --(CH.sub.2.sup.5).sub.z --(V) wherein x, y, and z have a value of from 0 to 20 and wherein the sum of x, y, and z is at least 1, but not greater than 20 and wherein R 5 is an alkyl group of 1 to 6 carbon atoms, R 1 contains 1 to 10 carbon atoms, and represents a straight or branched chain alkyl group, an aryl group, or an alkaryl group; R 2 is the same as R 1 and may additionally represent hydrogen, acyl, alkoxyalkyl, CH 3 OCH 2 CH 2 --, CH 3 OCH(CH 3 )CH 2 --, N═C(R')(R") wherein R' and R" are lower alkyl, and silyl groups including the hydrolytic conensation products thereof; R 3 contains 1 to 10 carbon atoms, and represents a saturated or unsaturated aliphatic or aryl group with the proviso that the R 3 groups need not be the same and the formula (I) must contain at least one alkyl group R 3 which contains an alpha-carbon with at least one hydrogen; R 4 represents hydrogen, aryl, or a straight or branched chain alkyl group of 1 to 10 carbon atoms, or --R--Si--(R.sub.(3-a).sup.1)(OR.sup.2).sub.a wherein R, R 1 and R 2 are as previously indicated n has a value of from 1 to 10, b has a value of from 2 to 5 and a has a value of 1, 2 or 3. which comprises reacting a compound selected from the group consisting of: HN(R.sup.4)RSi(R.sup.1).sub.(3-a))(OR.sup.2).sub.a and HN(R.sup.4)(C.sub.b H.sub.2b NH)RSi(R.sup.1).sub.(3-a))(OR.sup.2).sub.a with a compound of the formula: ##STR17## wherein x, n, a, R-R 4 are as indicated and X represents Cl, Br, I, or the groups --O--C 6 H 5 , --OC(R 3 ) 3 , or ##STR18## and thereafter recovering said carbamate.

Claim 40

The process of claim 34 wherein R is alkylene, R 1 -R 3 are alkyl, R 4 is hydrogen and a is 3.

Claim 41

The process of claim 34 wherein R is alkylene, R 1 -R 3 are alkyl, R 4 is hydrogen and a is 2.

Claim 42

The process of claim 34 wherein R is alkylene, R 1 -R 3 are alkyl, R 4 is hydrogen and a is 1.

Claim 43

The process of claim 34 wherein R is alkylene and contains at least 3 carbon atoms.

Claim 44

The process of claim 34 wherein x represents ##STR19## and R 3 is methyl.

Claim 45

The process of claim 34 wherein at least one R 3 group contains an alpha-carbon atom with at least one hydrogen.

Claim 46

The process of claim 34 wherein R 2 and R 3 are lower alkyl and a is 3.