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US 4,069,377 AGranted
Polymerization of ethylenically unsaturated monomers employing secondary-aliphatic .alpha.-substituted azoalkanes
AssigneePennwalt Corporation
InventorsRonald Edward MacLeay, Chester Stephen Sheppard
Life of this patent
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Abstract
Secondary-aliphatic .alpha.-substituted azoalkanes, such as 1-isopropylazo-1-azidocyclohexane, and processes using such azoalkanes as polymerization initiators for vinyl monomers and as curing agents for resins.
Claims8
A process which comprises polymerizing ethylenically unsaturated monomer in the presence of an initiating amount of a compound of the formula ##STR23## where:
- R' and R" are separately selected from alkyl of 1-12 carbons, cycloalkyl of 3-12 carbons, and aralkyl of 7-12 carbons, or join to form cycloalkyl of 3-12 carbons, and R" is further selected from aryl of 6-14 carbons;
- R.sub.1 and R.sub.2 are separately selected from alkyl of 1-8 carbons, cycloalkyl of 3-12 carbons and aralkyl of 7-12 carbons or join to form cycloalkyl of 4-12 carbons, and R.sub.2 is further selected from aryl of 6-14 carbons;
- X is selected from --Cl, --Br, --CN, --C(.dbd.O)NH.sub.2, --C(.dbd.NOH)NH.sub.2, --OH, --OR.sub.3, --OC(.dbd.O)OR.sub.3, --OOR.sub.5, --SR.sub.6, --N.sub.3, --SCN, --NCX', --NHC(.dbd.X')OR.sub.3, --NHC(.dbd.X')N(R.sub.8)R.sub.9, --NHC(.dbd.X')NHNHC(.dbd.X')R.sub.4, --NHC(.dbd.X')NHN(R.sub.8)C(.dbd.X')N(R.sub.8)R.sub.9, --NHC(.dbd.X')N(NH.sub.2)R.sub.10, --NHC(.dbd.X')NHNHR.sub.16, --NHC(.dbd.X')NHN(R'.sub.8)R'.sub.9, --NHC(.dbd.X')NHNHC(.dbd.X')X'R.sub.3, and ##STR24## X' is oxygen or sulfur;
- R.sub.3 and R.sub.4 are separately selected from alkyl of 1-12 carbons, cycloalkyl of 3-12 carbons, aralkyl of 7-12 carbons, and aryl of 6-14 carbons, and R.sub.4 is further selected from hydrogen;
- R.sub.5 is tertiary alkyl of 4-12 carbons or tertiary phenalkyl of 9-12 carbons;
- R.sub.6 is selected from alkyl of 1-12 carbons, cycloalkyl of 3-12 carbons, and aryl of 6-14 carbons;
- R.sub.8, r.sub.9, r'.sub.8 and R'.sub.9 are separately selected from alkyl of 1-8 carbons, cycloalkyl of 3-12 carbons, aralkyl of 7-12 carbons, and aryl of 6-14 carbons or R.sub.8 and R.sub.9 or R'.sub.8 and R'.sub.9 taken together form alkylene of 3-11 carbons, and R.sub.8 and R.sub.9 are further selected from hydrogen;
- R.sub.10 is primary or secondary alkyl of 1-12 carbons or cycloalkyl of 3-12 carbons;
- R.sub.15 is aryl of 6-10 carbons;
- and
- R.sub.16 is selected from hydrogen, tertiary alkyl of 4-8 carbons, tertiary aralkyl of 9-12 carbons, and aryl of 6-14 carbons.
8 more elements
A process which comprises polymerizing ethylenically unsaturated monomer in the presence of an initiating amount of a compound of the formula ##STR25## where:
- R' and R" are separately selected from alkyl of 1-12 carbons, cycloalkyl of 3-12 carbons, and aralkyl of 7-12 carbons, or join to form cycloalkyl of 3-12 carbons, and R" is further selected from aryl of 6-14 carbons;
- R.sub.1 and R.sub.2 are separately selected from alkyl of 1-8 carbons, cycloalkyl of 3-12 carbons and aralkyl of 7-12 carbons, or join to form cycloalkyl of 4-12 carbons, and R.sub.2 is further selected from aryl of 6-14 carbons;
- X is selected from --CN, --C(.dbd.O)NH.sub.2, --C(.dbd.NOH)NH.sub.2, --OH, --OR.sub.3, --OOR.sub.5, --SR.sub.6, --N.sub.3, --SCN, --NCX',
- X'is oxygen or sulfur;
- R.sub.3 is selected from alkyl of 1-12 carbons, cycloalkyl of 3-12 carbons, aralkyl of 7-12 carbons, and aryl of 6-14 carbons;
- R.sub.5 is tertiary alkyl of 4-12 carbons or tertiary aralkyl of 9-12 carbons;
- and
- R.sub.6 is alkyl of 1-12 carbons, cycloalkyl of 3-12 carbons or aryl of 6-14 carbons.
5 more elements
Dependencies are inferred from the claim text.