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US5155167A Expired / Lapsed US ⏱️ 0.0 years remaining

Vinyl alcohol copolymers containing allylamine functionality

Assignee: University of Pittsburgh
•
Filing: 1989-10-30
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Granted: 1992-10-13
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Expires: 2009-10-30
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Abstract

Abstract A modified poly(vinyl alcohol) copolymer is provided containing copolymerized units of allylamine and/or diallylamine by copolymerizing a vinyl ester, such as vinyl acetate, and an N-allylamide and/or N,N-diallylamide, such as N-allylformamide and/or N,N-diallylformamide and hydrolyzing first the ester groups to hydroxy groups and then the amide groups to amine groups. The second hydrolysis is carried out on solvent-swollen particulate polymer slurried in an acidic or basic medium. The modified polymer can contain small amounts of unhydrolyzed ester and amide groups in addition to the hydroxy and amine functionality which characterizes the copolymer.

Inventors

  • 👤 Robert K. Pinschmidt, Jr.
  • 👤 Ta-Wang Lai
  • 👤 Lawrence K. Wempe

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 08:45
CPC Classifications
C; C08; C08F; C08F8/00; C08F8/12; C08F2810/00; C08F2810/20

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 55 words
A process for making a poly(vinyl alcohol) copolymer containing copolymerized units of allylamine or diallylamine or both which comprises suspending in methanol particles of a poly(vinyl alcohol) copolymer containing copolymerized units of N-allylamide or N,N-diallylamide or both and hydrolyzing said amide-containing copolymer particles under acidic or basic conditions to form particles of said amine-containing copolymer.
Claim 2
Dependent Claim 55 words
A process for making a poly(vinyl alcohol) copolymer containing copolymerized units of allylamine or diallylamine or both which comprises suspending in methanol particles of a poly(vinyl alcohol) copolymer containing copolymerized units of N-allylamide or N,N-diallylamide or both and hydrolyzing said amide-containing copolymer particles under acidic or basic conditions to form particles of said amine-containing copolymer.
Claim 3
Dependent Claim 22 words
The process of claim 1 wherein the hydrolysis is performed using basic conditions to yield salt free particles of said amine-containing copolymer.
Claim 4
Dependent Claim 25 words
The process of claim 1 wherein the hydrolysis is performed under acidic conditions to yield particles of the corresponding acid salt of said amine-containing copolymer.
Claim 5
Dependent Claim 119 words
The process of claim 1 wherein said poly(vinyl alcohol) amide-containing copolymer can be represented by the following structural formula having randomly copolymerized monomer units in the indicated molar proportions: ##STR6## wherein R is H, alkyl containing 1 to 11 carbons, phenyl, or trifluoromethyl; R 1 is H, alkyl containing 1 to 4 carbons, or 2-hydroxyalkyl containing 1 to 4 carbons, each R 2 is H, methyl or trifluoromethyl; m, n, x and y are integers which added together make a sum; m is 0 to 15 percent of said sum; n is 50 to 99 percent of said sum; and x or y can be zero but the total of x+y is 1 to 50 percent of said sum.
Claim 6
Dependent Claim 23 words
The process of claim 4 wherein the hydrolysis is performed under basic conditions and m is 0 to 2 percent of said sum.
Claim 7
Dependent Claim 18 words
The process of claim 4 wherein x is zero, and R is methyl and R 2 is hydrogen.
Claim 8
Dependent Claim 20 words
The process of claim 4 wherein y is zero, R is methyl, and R 1 and R 2 are hydrogen.
Claim 9
Dependent Claim 109 words
A process for making a poly(vinyl alcohol) copolymer containing copolymerized units of allylamine and/or diallylamine which comprises: (a) copolymerizing vinyl acetate with either or both of N-allylformamide and N,N-diallylformamide to form a poly(vinyl acetate) copolymer containing copolymerized units of N-allylformamide or N,N-diallylformamide or both in an alcohol solution, (b) hydrolyzing the acetate functionality of said poly(vinyl acetate) copolymer in a methanolic medium to form a poly(vinyl alcohol) copolymer containing copolymerized units of N-allylformamide or N,N-diallylformamide or both as a particulate gel swollen with methanol, and (c) hydrolyzing said particulate gel as a slurry in methanol with 0 to 20 percent water to form said amine-containing copolymer of poly(vinyl alcohol).
Claim 10
Dependent Claim 109 words
A process for making a poly(vinyl alcohol) copolymer containing copolymerized units of allylamine and/or diallylamine which comprises: (a) copolymerizing vinyl acetate with either or both of N-allylformamide and N,N-diallylformamide to form a poly(vinyl acetate) copolymer containing copolymerized units of N-allylformamide or N,N-diallylformamide or both in an alcohol solution, (b) hydrolyzing the acetate functionality of said poly(vinyl acetate) copolymer in a methanolic medium to form a poly(vinyl alcohol) copolymer containing copolymerized units of N-allylformamide or N,N-diallylformamide or both as a particulate gel swollen with methanol, and (c) hydrolyzing said particulate gel as a slurry in methanol with 0 to 20 percent water to form said amine-containing copolymer of poly(vinyl alcohol).
Claim 11
Dependent Claim 59 words
The process of claim 8 wherein said alcohol is methanol, said solution of step (a) is diluted with methanol and unreacted vinyl acetate is distilled therefrom prior to step (b), said particulate gel from step (b) is filtered and washed with methanol prior to step (c), and the product of step (c) is separated, washed with methanol and dried.
Claim 12
Dependent Claim 25 words
The process of claim 8 wherein said hydrolyzing of step (b) is under basic conditions and said hydrolyzing of step (c) is under acidic conditions.
Claim 13
Dependent Claim 145 words
A copolymer of vinyl alcohol containing amine functionality and having the structural formula of randomly interpolymerized monomer units in the indicated molar proportions: ##STR7## wherein R is H, alkyl containing 1 to 11 carbons, phenyl, or trifluoromethyl; R 1 is H, alkyl containing 1 to 4 carbons, or 2-hydroxyalkyl containing 1 to 4 carbons; each R 2 is H, methyl or trifluoromethyl; m, n, x, y, a and b are integers which added together make a sum; m is 0 to 15 percent of said sum; n is 50 to 99 percent of said sum; x plus y are 0 to 30 percent of said sum; and a or b can be zero but the total of a and b is 1 to 50 percent of said sum, except that b is greater than zero when a is less than 5 percent of said sum.
Claim 14
Dependent Claim 145 words
A copolymer of vinyl alcohol containing amine functionality and having the structural formula of randomly interpolymerized monomer units in the indicated molar proportions: ##STR7## wherein R is H, alkyl containing 1 to 11 carbons, phenyl, or trifluoromethyl; R 1 is H, alkyl containing 1 to 4 carbons, or 2-hydroxyalkyl containing 1 to 4 carbons; each R 2 is H, methyl or trifluoromethyl; m, n, x, y, a and b are integers which added together make a sum; m is 0 to 15 percent of said sum; n is 50 to 99 percent of said sum; x plus y are 0 to 30 percent of said sum; and a or b can be zero but the total of a and b is 1 to 50 percent of said sum, except that b is greater than zero when a is less than 5 percent of said sum.
Claim 15
Dependent Claim 57 words
The copolymer of claim 11 wherein R is methyl, R 1 and R 2 are hydrogen, m is 0 to 2 percent of said sum, n is 80 to 97 percent of said sum, x plus y are 0 to 4 percent of said sum, and a plus b are 3 to 20 percent of said sum.
Claim 16
Dependent Claim 11 words
The copolymer of claim 12 wherein y and b are zero.
Claim 17
Dependent Claim 11 words
The copolymer of claim 12 wherein x and a are zero.
Claim 18
Dependent Claim 15 words
The copolymer of claim 13 wherein x is 0.5 to 4 percent of said sum.
Claim 19
Dependent Claim 15 words
The copolymer of claim 14 wherein y is 0.5 to 4 percent of said sum.

References Cited (Backward Citations)

US2748103A Cited
US3032539A Cited
US4421602A Cited
US4490557A Cited
US4393174A Cited
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US4774285A Cited
US4772359A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1995-10-13 1996-04-13 1996-10-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1999-10-13 2000-04-13 2000-10-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2003-10-13 2004-04-13 2004-10-13 $7700.00 Window Closed / Lapsed

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