NITROGEN-CONTAINING COMPOUNDS

• US 3,700,713 A
• Filed: 07/10/1969
• Issued: 10/24/1972
• Est. Priority Date: 07/26/1968
• Status: Expired due to Term

• Current Assignee: John Beckett Plumb, John Heathcote Atherton
• Original Assignee: John Beckett Plumb, John Heathcote Atherton
• Inventors: Atherton, John Heathcote, Plumb, John Beckett
• Primary Examiner(s): Poer, James E.
• Assistant Examiner(s): Shaver, P. F.
• Application Number:
  US04/840,853
• Time in Patent Office: 1,202 Days
• Field of Search: 260/448.2N,448.2E,448.8R
• US Class Current: 556/419
• CPC Class Codes: C03C 25/40 Organo-silicon compounds
• CPC Class Codes: C07F 7/0834 Compounds having one or more O-Si linkage for compounds with C-O-Si linkages see C07F7/18
• CPC Class Codes: C08G 77/26 nitrogen-containing groups

Abstract

Nitrogen-containing compounds comprising organo-silicon compounds containing at least one unit of the average general formula WHERE A is a group of the general formula IN WHICH R is an organic group free from olefinic unsaturation and having a valency of c + 1 and is selected from the group consisting of hydrocarbon groups having from three to 11 carbon atoms and groups consisting of carbon, hydrogen and oxygen, the latter in the form of ethereal linkages, having from six to 17 carbon atoms, R1 is selected from the group consisting of lower alkylene groups, R2 is selected from the group consisting of hydrogen, hydrocarbyl groups having not more than 12 carbon atoms and groups of the general formula (R3NRR4R5), R3 is a divalent radical attached at its extremities to two nitrogen atoms and is selected from the group consisting of hydrocarbon groups having not more than 12 carbon atoms, polyimino groups of the general formula ((R7NH)qR8) where R7 and R8 are alkylene groups having not more than four carbon atoms and q is a positive integer not greater than 100, and groups forming a heterocyclic structure with the amino nitrogen and R4 or with R2, R4 and the two nitrogen atoms attached to the extremities of R3, R4, when not a member of a heterocyclic structure, is selected from the group consisting of hydrogen, hydrocarbyl and hydroxy substituted hydrocarbyl groups and amino-alkyl and N-substituted amino-alkyl groups, R5 is selected from the group consisting of hydrogen, hydrocarbyl groups, hydroxy substituted hydrocarbyl groups, amino-alkyl and N-substituted amino-alkyl groups, c is 1, 2 or 3, B is a hydrocarbyl group free from aliphatic unsaturation, D is selected from the group consisting of hydrocarbyl groups and groups of the general formula B(OCnH2n)x, r is 1 or 2, s is 0, 1, 2, or 3, t is 0, 1, 2 or 3 and r + s + t is not greater than 4.

Claims

2. Nitrogen-containing compounds according to claim 1 wherein r is 1 and R is a 1,3-propylene group.

3. Nitrogen-containing compounds according to claim 2 wherein R1 is selected from the group consisting of methylene and 1,2-ethylene groups.

4. Nitrogen-containing compounds according to claim 1 wherein the group R2 is selected from the group consisting of alkyl, aryl, aralkyl, alkenyl and cycloalkyl groups having not more than 12 carbon atoms, the group R3 is a divalent hydrocarbon group selected from the group consisting of ethylene, 1,3-propylene 1, 6-hexylene and 1,4-phenylene groups and the groups R4 and R5 are selected from the group consisting of alkyl, aryl and aralkyl groups.

5. Nitrogen-containing compounds according to claim 1 wherein the group B is present and is selected from the group consisting of methyl, ethyl, tetradecyl, octadecyl, cyclohexyl, phenyl, tolyl, benzyl, phenylethyl, chloromethyl, chlorophenyl, beta-cyanoethyl and gamma-cyanopropyl groups.

6. Nitrogen-containing compounds according to claim 1 wherein the group D is present and is selected from the group consisting of alkyl, aryl, aralkyl, alkaryl and cycloalkyl groups.

7. Nitrogen-containing compounds according to claim 1 wherein the organosilicon compound is a siloxane and the remainder of the units therein are selected from the group consisting of Z3SiO0.5, Z2SiO, ZSiO1.5 and SiO2 in which the group Z is selected from the group consisting of substituted and unsubstituted hydrocarbyl groups.

8. Nitrogen-containing compounds according to claim 7 wherein the group Z is selected from the group consisting of halogen substituted, cyano-substituted and unsubstituted alkyl, aryl, aralkyl and cycloalkyl groups.

9. A nitrogen-containing compound according to claim 1 wherein the average general formula is

10. A process for the production of nitrogen-containing compounds as claimed in claim 1 comprising reacting an organosilicon compound containing at least one group of the general formula wherein R is an organic group free from olefinic unsaturation and having a valency of c + 1 and is selected from the group consisting of hydrocarbon groups having from three to 11 carbon atoms and groups consisting of carbon, hydrogen and oxygen, the latter in the form of ethereal linkages, having from six to 17 carbon atoms, R1 is selected from the group consisting of lower alkylene groups, G is a hydrocarbyl group and c is 1, 2 or 3, with an amino compound of the general formula wherein R2 is selected from the group consisting of hydrogen and hydrocarbyl groups having not more than 12 carbon atoms, R3 is a divalent radical attached at its extremities to two nitrogen atoms and is selected from the group consisting of hydrocarbon groups having not more than 12 carbon atoms, R4 and R5 are selected from the group consisting of hydrogen and hydrocarbyl groups.

11. A process for the production of nitrogen-containing compounds as claimed in claim 1 comprising reacting a compound of the general formula wherein G1, G2 and G3 are groups such that the group is the same as group R1 which is selected from the group consisting of lower alkylene groups, G is a hydrocarbyl group and c is 1, 2 or 3 With an amino compound of the general formula wherein R2 is selected from the group consisting of hydrogen and hydrocarbyl groups having not more than 12 carbon atoms, R3 is a divalent radical attached at its extremities to two nitrogen atoms and is selected from the group consisting of hydrocarbon groups having not more than 12 carbon atoms, R4 and R5 are selected from the group consisting of hydrogen and hydrocarbyl groups, and then reacting the product with an organosilicon compound containing at least one silicon-bonded hydrogen atom and having at least one unit of the general formula wherein B is a hydrocarbyl group free from aliphatic unsaturation, D is a hydrocarbyl group or a group of the general formula B(OCnH2n)x, r is 1 or 2, s is 0, 1, 2 or 3, t is 0, 1, 2 or 3 and r + s + t is not greater than 4, n is 2, 3 or 4 and x is an integer not greater than 100.