US4028344A
Expired / Lapsed
US
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α-ISOCYANATO AND α-ISOTHIOCYANATO AZOS AND THEIR DERIVATIVES
Assignee: Arkema Inc
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Filing: 1974-03-21
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Granted: 1977-06-07
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Expires: 1994-03-21
Abstract
Abstract Azoalkanes of the formula ##STR1## WHERE Z is isocyanate or isothiocyanate or derivatives thereof, such as 1-t-butylazo-1-isothiocyanatocyclohexane, which are useful as foaming agents for polyester resins and as free radical initiators for vinyl monomers.
Inventors
- 👤 Harold Carl Lange
- 👤 Ronald Edward MacLeay
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 21:40
CPC Classifications
C; C08; C08J; C08J9/00; C08J9/04; C08J9/06; C08J9/10; C08J9/102; C08F; C08F4/00; C08F4/04; C08J2367/00; C08J2367/06
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
297 words
A compound of the formula ##STR77## where: a. n is 1 or 2; b. R', R" and R'" are selected from alkyl of 1-8 carbons and and aralkyl of 7-12 carbons, or 2 or more of R', R" and R'" joined with the tertiary carbon atom to which they are attached form cycloalkyl of 3-12 carbons: or R" is aryl of 6-14 carbons; or R'" is cyano or Y; c. R 1 and R 2 are selected from alkyl of 1-8 carbons, cycloalkyl of 3-12 carbons, aralkyl of 7-12 carbons, or taken together are alkylene of 3-11 carbons; or R 2 is aryl of 6-14 carbons; d. Z, when n is 1, and Y have the same definition and are selected from: ##STR78## e. X is oxygen or sulfur; f. R 3 and R 4 are selected from hydrogen, alkyl of 1-12 carbons, cycloalkyl or 3-12 carbons, aralkyl of 7-12 carbons, aryl of 6-14 carbons and, taken together, alkylene of 3-11 carbons; g. R 5 is selected from alkyl of 1-12 carbons, cycloalkyl of 3-12 carbons, aralkyl of 7-12 carbons and aryl of 6-14 carbons; h. R 6 is selected from hydrogen, alkyl of 1-8 carbons, cycloalkyl of 3-8 carbons, aralkyl of 7-12 carbons and aryl of 6-14 carbons; i. R 7 is selected from primary or secondary alkyl of 1-12 carbons and cycloalkyl of 3-12 carbons; j. R 8 is selected from tertiary alkyl of 4-8 carbons and aryl of 6-14 carbons; and k. R 9 is a hydrocarbyl diradical selected from aliphatic hydrocarbyl of 2-20 carbons, cycloaliphatic hydrocarbyl of 3-20 carbons, aliphatic-cycloaliphatic hydrocarbyl of 4-20 carbons and aromaticaliphatic hydrocarbyl of 7-20 carbons optionally containing one or more nonadjacent and nonterminal oxygen, sulfur or nitrogen atoms in the backbone structure, and from aromatic of 6-12 carbons.
Claim 2
Dependent Claim
297 words
A compound of the formula ##STR77## where: a. n is 1 or 2; b. R', R" and R'" are selected from alkyl of 1-8 carbons and and aralkyl of 7-12 carbons, or 2 or more of R', R" and R'" joined with the tertiary carbon atom to which they are attached form cycloalkyl of 3-12 carbons: or R" is aryl of 6-14 carbons; or R'" is cyano or Y; c. R 1 and R 2 are selected from alkyl of 1-8 carbons, cycloalkyl of 3-12 carbons, aralkyl of 7-12 carbons, or taken together are alkylene of 3-11 carbons; or R 2 is aryl of 6-14 carbons; d. Z, when n is 1, and Y have the same definition and are selected from: ##STR78## e. X is oxygen or sulfur; f. R 3 and R 4 are selected from hydrogen, alkyl of 1-12 carbons, cycloalkyl or 3-12 carbons, aralkyl of 7-12 carbons, aryl of 6-14 carbons and, taken together, alkylene of 3-11 carbons; g. R 5 is selected from alkyl of 1-12 carbons, cycloalkyl of 3-12 carbons, aralkyl of 7-12 carbons and aryl of 6-14 carbons; h. R 6 is selected from hydrogen, alkyl of 1-8 carbons, cycloalkyl of 3-8 carbons, aralkyl of 7-12 carbons and aryl of 6-14 carbons; i. R 7 is selected from primary or secondary alkyl of 1-12 carbons and cycloalkyl of 3-12 carbons; j. R 8 is selected from tertiary alkyl of 4-8 carbons and aryl of 6-14 carbons; and k. R 9 is a hydrocarbyl diradical selected from aliphatic hydrocarbyl of 2-20 carbons, cycloaliphatic hydrocarbyl of 3-20 carbons, aliphatic-cycloaliphatic hydrocarbyl of 4-20 carbons and aromaticaliphatic hydrocarbyl of 7-20 carbons optionally containing one or more nonadjacent and nonterminal oxygen, sulfur or nitrogen atoms in the backbone structure, and from aromatic of 6-12 carbons.
Claim 3
Dependent Claim
14 words
A compound as in claim 1 wherein n is 1 and Z is -NCX.
Claim 4
Dependent Claim
8 words
A compound as in claim 1, 2-t-butylazo -1-isothiocyanatocyclohexane.
Claim 5
Dependent Claim
7 words
A compound as in claim 1, 2-t-butylazo-2-isocyanatopropane.
Claim 6
Dependent Claim
7 words
A compound as in claim 1, N-(1-(t-butylazo)cyclohexyl)-N',N'-diethylurea.
Claim 7
Dependent Claim
7 words
A compound as in claim 1, 2,2'-azobis(2-isothiocyanato-4-methylpentane).
Claim 8
Dependent Claim
7 words
A compound as in claim 1, 2,2'-azobis-(2-isocyanatobutane).
Claim 9
Dependent Claim
7 words
A compound as in claim 1, N-(1-(t-butylazo)-1,3-dimethylbutyl)-N'-butylthiourea.
Claim 10
Dependent Claim
7 words
A compound as in claim 1, 1-t-butylazo-1-(methoxythiocarbonyl-amino)-cyclohexane.
Claim 11
Dependent Claim
8 words
A compound as in claim 1, 2-t-butylazo-2-(methoxycarbonylamino) propane.
References Cited (Backward Citations)
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US3282912A
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US3649614A
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US3644406A
Cited
US3775395A
Cited
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-06-06 | 1980-12-06 | 1981-06-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-06 | 1984-12-06 | 1985-06-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-06 | 1988-12-06 | 1989-06-07 | $7700.00 | Window Closed / Lapsed |