US4031138A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Stable substituted acrylamides or methacrylamides
Assignee: Huntsman Corp
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Filing: 1976-03-18
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Granted: 1977-06-21
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Expires: 1996-03-18
Abstract
Abstract Covers a new composition of matter comprising a stable N-(ω-monoalkylaminoalkyl) acrylamide or methacrylamide monomer characterized by the following structural formula: ##STR1## where R 1 and R 2 are hydrogen or methyl, R 3 is isopropyl or t-butyl and n is 2 or 3, with the proviso that when R 1 is hydrogen, R 3 is t-butyl. Also covers a method of preparing said monomer by condensing one mole of an acrylic or methacrylic compound with two moles of an appropriate amine to form an intermediate substituted amide, followed by heating said intermediate to split off one mole of reactant diamine leaving the desired substituted aminoalkyl acrylamide or acrylamide monomer.
Inventors
- 👤 Edward C. Y. Nieh
- 👤 Philip H. Moss
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 07:19
CPC Classifications
D; D21; D21H; D21H17/00; D21H17/03; D21H17/05; D21H17/07; C; C02; C02F; C02F1/00; C02F1/52; C02F1/54; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/16; C08G18/18; C08G18/1866
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
49 words
A stable N-(ω-monoalkylaminoalkyl) acrylamide or methacrylamide monomer characterized by the following structural formula: ##STR11## where R 1 and R 2 are hydrogen or methyl, R 3 is isopropyl or t-butyl and n is 2 or 3, with the proviso that when R 1 is hydrogen, R 3 is t-butyl.
Claim 2
Dependent Claim
49 words
A stable N-(ω-monoalkylaminoalkyl) acrylamide or methacrylamide monomer characterized by the following structural formula: ##STR11## where R 1 and R 2 are hydrogen or methyl, R 3 is isopropyl or t-butyl and n is 2 or 3, with the proviso that when R 1 is hydrogen, R 3 is t-butyl.
Claim 3
Dependent Claim
22 words
The monomer of claim 1 wherein R 1 is methyl, R 2 is hydrogen, R 3 is isopropyl and n is 3.
Claim 4
Dependent Claim
22 words
The monomer of claim 1 wherein R 1 is methyl, R 2 is hydrogen, R 3 is t-butyl and n is 3.
Claim 5
Independent Claim
192 words
A method of preparing a stable N-(ω-monoalkylaminoalkyl) acrylamide or methacrylamide monomer characterized by the following structural formula: ##STR12## where R 1 and R 2 are hydrogen or methyl, R 3 is isopropyl or t-butyl and n is 2 or 3, with the proviso that when R 1 is hydrogen, R 3 is t-butyl; which comprises the steps of condensing one mole of an acrylic or methyacrylic compound having the structure: ##STR13## where R 1 is hydrogen or methyl and X is selected from the group consisting of halo, OH, or OR 4 where R 4 is lower alkyl, with a diamine having the structure: R.sub.2 NHC.sub.n H.sub.2n NHR.sub.3 where R 2 is hydrogen or methyl, R 3 is isopropyl or t-butyl and n is 2 or 3, with the proviso that where R 1 is hydrogen, R 3 is t-butyl, to provide an intermediate compound having the structure: ##STR14## where R 1 , R 2 , R 3 , and n have a significance as above defined, and heating said intermediate compound at a sufficient temperature to split off one mole of said diamine reactant to yield said N-(ω-monoalkylaminoalkyl) acrylamide or methacrylamide.
Claim 6
Independent Claim
192 words
A method of preparing a stable N-(ω-monoalkylaminoalkyl) acrylamide or methacrylamide monomer characterized by the following structural formula: ##STR12## where R 1 and R 2 are hydrogen or methyl, R 3 is isopropyl or t-butyl and n is 2 or 3, with the proviso that when R 1 is hydrogen, R 3 is t-butyl; which comprises the steps of condensing one mole of an acrylic or methyacrylic compound having the structure: ##STR13## where R 1 is hydrogen or methyl and X is selected from the group consisting of halo, OH, or OR 4 where R 4 is lower alkyl, with a diamine having the structure: R.sub.2 NHC.sub.n H.sub.2n NHR.sub.3 where R 2 is hydrogen or methyl, R 3 is isopropyl or t-butyl and n is 2 or 3, with the proviso that where R 1 is hydrogen, R 3 is t-butyl, to provide an intermediate compound having the structure: ##STR14## where R 1 , R 2 , R 3 , and n have a significance as above defined, and heating said intermediate compound at a sufficient temperature to split off one mole of said diamine reactant to yield said N-(ω-monoalkylaminoalkyl) acrylamide or methacrylamide.
Claim 7
Dependent Claim
22 words
The method of claim 4 wherein R 1 is methyl, R 2 is hydrogen, R 3 is isopropyl and n is 3.
Claim 8
Dependent Claim
22 words
The method of claim 4 wherein R 1 is methyl, R 2 is hydrogen, R 3 is t-butyl and n is 3.
Claim 9
Dependent Claim
20 words
The method of claim 4 wherein said condensation step is carried out at a temperature of 150°-190° C. under pressure.
Claim 10
Dependent Claim
11 words
The method of claim 7 wherein said pressure is 1-20 atmospheres.
Claim 11
Dependent Claim
24 words
The method of claim 4 wherein said second step of splitting off diamine is carried out at a temperature of 180°-280° C. under vacuum.
Claim 12
Dependent Claim
12 words
The method of claim 9 wherein said vacuum reading is 1-75 mm.
Claim 13
Dependent Claim
19 words
The method of claim 4 wherein 2-3 moles of diamine are condensed per mole of acrylic or methacrylic compound.
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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) | 1980-06-20 | 1980-12-20 | 1981-06-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-20 | 1984-12-20 | 1985-06-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-20 | 1988-12-20 | 1989-06-21 | $7700.00 | Window Closed / Lapsed |