US4233434A
Expired / Lapsed
US
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Polyamide from aromatic phosphorus containing diamine
Assignee: Ramot A T Plastics Ltd
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Filing: 1978-05-09
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Granted: 1980-11-11
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Expires: 1998-05-09
Abstract
Abstract The present invention relates to novel aromatic and araliphatic polymers and copolymers based on phosphoric acid and thiophosphoric acid amides, esters and thioesters, to monomers for the production of these and to various products prepared from such polymers and copolymers, such as films, membranes, fibers and shaped objects.
Inventors
- 👤 Menahem A. Kraus
- 👤 Moshe A. Frommer
- 👤 Mara Nemas
- 👤 Rodika Gutman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 23:05
CPC Classifications
B; B01; B01D; B01D71/00; B01D71/06; B01D71/56; A; A61; A61M; A61M1/00; A61M1/36; A61M1/3679; B01D67/00; B01D67/0002; B01D67/0006
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
191 words
A polymer consisting essentially of the following repeating unit: ##STR22## wherein X designates --NHAr, N(R)Ar, --NRR', NHR, --OR, --OAr, or SR, Y designates --O--, --NH--, --S--, or --N(CH 3 )--, Z designates ═O or ═S, Q, Q' and Q" designate p-C 6 H 4 , m-C 6 H 4 , R"C 6 H 3 , ##STR23## which Q, Q', and Q" may be identical or different, Ar designates --C 6 H 5 , or RC 6 H 4 , R designates --CH 3 , C 2 H 5 , or --n--C 3 H 7 , R' designates --CH 3 , C 2 H 5 , or --C 3 H 7 , and R" designates --CH 3 , --C 2 H 5 , n--C 3 H 7 , --OCH 3 , --OH, --COOH or --COOR, wherein R is as defined above, x is an integer of from 1 to 5, y is zero or an integer of 1 to 5, and n is an integer of from 50 to 200; wherein the repeating portions within the right-hand parentheses of said repeating unit when y is greater than 1 are alike or different.
Claim 2
Dependent Claim
191 words
A polymer consisting essentially of the following repeating unit: ##STR22## wherein X designates --NHAr, N(R)Ar, --NRR', NHR, --OR, --OAr, or SR, Y designates --O--, --NH--, --S--, or --N(CH 3 )--, Z designates ═O or ═S, Q, Q' and Q" designate p-C 6 H 4 , m-C 6 H 4 , R"C 6 H 3 , ##STR23## which Q, Q', and Q" may be identical or different, Ar designates --C 6 H 5 , or RC 6 H 4 , R designates --CH 3 , C 2 H 5 , or --n--C 3 H 7 , R' designates --CH 3 , C 2 H 5 , or --C 3 H 7 , and R" designates --CH 3 , --C 2 H 5 , n--C 3 H 7 , --OCH 3 , --OH, --COOH or --COOR, wherein R is as defined above, x is an integer of from 1 to 5, y is zero or an integer of 1 to 5, and n is an integer of from 50 to 200; wherein the repeating portions within the right-hand parentheses of said repeating unit when y is greater than 1 are alike or different.
Claim 3
Dependent Claim
30 words
A polymer according to claim 1 of the formula ##STR24## wherein y is an integer of from 1 to 5 and x and n are as defined in claim 1.
Claim 4
Dependent Claim
18 words
A polymer according to claim 1, of the formula ##STR25## wherein n is as defined in claim 1.
Claim 5
Dependent Claim
18 words
A polymer according to claim 1, of the formula ##STR26## wherein n is as defined in claim 1.
Claim 6
Dependent Claim
18 words
A polymer according to claim 1, of the formula ##STR27## wherein n is as defined in claim 1.
Claim 7
Dependent Claim
27 words
A polymer according to claim 1, being the polymerization product of an aromatic phosphoric acid ester diamine or thiophosphoric ester amide diamine with an aromatic diacid dichloride.
Claim 8
Dependent Claim
25 words
A polymer according to claim 1, being the polymerization product of an aromatic phosphoric triester diamine or thiophosphoric triester diamine with an aromatic diacid dichloride.
Claim 9
Dependent Claim
26 words
A polymer according to claim 1, being the polymerization product of an aromatic phosphoric triamide diamine with a diamine aromatic hydrocarbon and an aromatic diacid dichloride.
Claim 10
Dependent Claim
40 words
A polymer according to claim 1, of the formula ##STR28## wherein y' and y" are integers which added together total y, y is an integer of from 1 to 5, and x and n are as defined in claim 1.
Claim 11
Dependent Claim
28 words
A polymer according to claim 1, of the formula ##STR29## wherein y is an integer of from 1-5 and x and n are as defined in claim 1.
Claim 12
Dependent Claim
25 words
A polymer according to claim 1, in the form of a membrane, and having the formula ##STR30## wherein n is as defined in claim 1.
Claim 13
Dependent Claim
19 words
A polymer in accordance with claim 1, in the form of a membrane, film, fiber or other shaped product.
Claim 14
Dependent Claim
36 words
A polymer according to claim 1, in the form of a membrane and having the formula ##STR31## wherein y is an integer of 1 to 5 and x and n are as defined in claim 1.
Claim 15
Dependent Claim
35 words
A process for producing the polymer defined in claim 1, wherein y is zero, comprising polymerizing a diamine monomer of the formula XP(═Z)(YQNH 2 ) 2 with an aromatic diacid dichloride of the formula ClCO--Q'--COCl.
Claim 16
Dependent Claim
81 words
A process in accordance with claim 14 wherein said diamine monomer is prepared by treating a phosphorus oxyhalide or thiohalide (POhal 3 or PShal 3 ) with a nucleophile to yield a N-phenyl-phosphoramide or phosphoric ester dihalide, or thiophosphoramide or thiophosphoric ester dihalide; condensing this reaction product with 2 equivalents of a nitro-aromatic nucleophile of the formula HYQNO 2 , to yield a compound of the formula XP(═Z)(YQNO 2 ) 2 ; and reducing by catalytic hydrogenation to the diamine monomer.
Claim 17
Dependent Claim
53 words
A process for producing the polymer defined in claim 1, wherein y is an integer of 1 to 5, comprising polymerizing a diamine monomer of the formula XP(═Z)(YQNH 2 ) 2 with an additional aromatic diamine of the formula NH 2 Q"NH 2 and with an aromatic diacid dichloride of the Formula ClCO--Q'--COCl.
Claim 18
Dependent Claim
81 words
A process in accordance with claim 16 wherein said diamine monomer is prepared by treating a phosphorus oxyhalide or thiohalide (POhal 3 or PShal 3 ) with a nucleophile to yield a N-phenyl-phosphoramide or phosphoric ester dihalide, or thiophosphoramide or thiophosphoric ester dihalide; condensing this reaction product with 2 equivalents of a nitroaromatic nucleophile of the formula HYQNO 2 , to yield a compound of the formula XP(═Z)(YQNO 2 ) 2 ; and reducing by catalytic hydrogenation to the diamine monomer.
Claim 19
Dependent Claim
57 words
A process according to claim 14, wherein the additional aromatic diamine is selected from the group consisting of phenylene diamines, naphthalene diamines and biphenyl diamines, and the aromatic diacid dichloride is a member selected from the group consisting of isophthalic and terephthalic acid chloride, p,p'-biphenyl diacid dichloride, p,p'-diphenylmethane diacid dichloride, p,p'-diphenylsulfone diacid dichloride, and 4,6-naphthalene diacid dichloride.
Claim 20
Dependent Claim
21 words
A process according to claim 15 or 17 wherein the ratio of HYQNO 2 to ##STR32## is from 2:1 to 4:1.
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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) | 1983-11-11 | 1984-05-12 | 1984-11-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-11 | 1988-05-12 | 1988-11-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-11 | 1992-05-12 | 1992-11-11 | $7700.00 | Window Closed / Lapsed |