US4451619A
Expired / Lapsed
US
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Method of hydrophilizing or hydrophobizing polymers
Assignee: 3M Co
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Filing: 1982-09-30
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Granted: 1984-05-29
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Expires: 2002-09-30
Abstract
Abstract A method of modifying the overall hydrophilic or hydrophobic nature of a high molecular weight free radical addition interpolymer, which is an azlactone-functional interpolymer, with a hydrophilic or hydrophobic nucleophilic compound is disclosed. Only the surface of the interpolymer can by hydrophilized or hydrophobized, as when the interpolymer is a coating, or the modification can take place throughout the entire bulk of the interpolymer.
Inventors
- 👤 Steven M. Heilmann
- 👤 Jerald K. Rasmussen
- 👤 Frederick J. Palensky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 11:00
CPC Classifications
C; C08; C08F; C08F8/00
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
337 words
A method for preparing thermoplastic, processable, hydrophilic- or hydrophobic-modified polymers comprising the steps: (a) interpolymerizing at a temperature in the range of room temperature to 100° C. in the presence of an amount of free radical initiator in the range of 0.01 to 5.0 weight percent (1) 1 to 50 mole percent of an alkenyl azlactone monomer, (2) 50 to 99 mole percent of at least one free radical addition polymerizable monomer, to form an interpolymer, said monomer being selected from the group consisting of vinyl aromatic compounds, α,β-unsaturated carboxylic acids and their derivatives, vinyl esters of carboxylic acids, vinyl halides, olefins, N-vinyl compounds, vinyl ketones, and vinyl aldehydes; (b) reacting in a ring-opening reaction at room or moderate temperatures in an unreactive solvent said resulting interpolymer with 0.1 to 1.0 equivalents, based on polymer-bound azlactone, of an alcohol- or amino-functional hydrophilic or hydrophobic nucleophile having a molecular weight greater than 100, said hydrophilic nucleophile having a Hydrophilicity Index greater than 30 or said hydrophobic nucleophile having a Hydrophilicity Index less than 20, and having the formula HXG wherein H is hydrogen, X is equal to --O--, or ##STR9## and wherein R 8 is equal to H, G, or G', wherein G' is any other hydrophilic or hydrophobic group other than G, or an alkyl group having from 1 to 4 carbon atoms, G is any hydrophilic group such that its Hydrophilicity Index has a value of at least 30 or G is any hydrophobic group such that its Hydrophilicity Index has a value of 20 or less, and G' is equal to G or can differ from G, provided that G' is alike in kind with G and the Hydrophilicity Index for the hydrophilic group or the hydrophobic group falls within the respective limitations for G; with the proviso that said reacting step takes place in the presence of 0.01 to 5.0 weight percent of a Bronsted or Lewis acid catalyst when said hydrophilic nucleophile is alcohol-functional; and (c) recovering the resulting hydrophilic- or hydrophobic-modified polymer.
Claim 2
Independent Claim
337 words
A method for preparing thermoplastic, processable, hydrophilic- or hydrophobic-modified polymers comprising the steps: (a) interpolymerizing at a temperature in the range of room temperature to 100° C. in the presence of an amount of free radical initiator in the range of 0.01 to 5.0 weight percent (1) 1 to 50 mole percent of an alkenyl azlactone monomer, (2) 50 to 99 mole percent of at least one free radical addition polymerizable monomer, to form an interpolymer, said monomer being selected from the group consisting of vinyl aromatic compounds, α,β-unsaturated carboxylic acids and their derivatives, vinyl esters of carboxylic acids, vinyl halides, olefins, N-vinyl compounds, vinyl ketones, and vinyl aldehydes; (b) reacting in a ring-opening reaction at room or moderate temperatures in an unreactive solvent said resulting interpolymer with 0.1 to 1.0 equivalents, based on polymer-bound azlactone, of an alcohol- or amino-functional hydrophilic or hydrophobic nucleophile having a molecular weight greater than 100, said hydrophilic nucleophile having a Hydrophilicity Index greater than 30 or said hydrophobic nucleophile having a Hydrophilicity Index less than 20, and having the formula HXG wherein H is hydrogen, X is equal to --O--, or ##STR9## and wherein R 8 is equal to H, G, or G', wherein G' is any other hydrophilic or hydrophobic group other than G, or an alkyl group having from 1 to 4 carbon atoms, G is any hydrophilic group such that its Hydrophilicity Index has a value of at least 30 or G is any hydrophobic group such that its Hydrophilicity Index has a value of 20 or less, and G' is equal to G or can differ from G, provided that G' is alike in kind with G and the Hydrophilicity Index for the hydrophilic group or the hydrophobic group falls within the respective limitations for G; with the proviso that said reacting step takes place in the presence of 0.01 to 5.0 weight percent of a Bronsted or Lewis acid catalyst when said hydrophilic nucleophile is alcohol-functional; and (c) recovering the resulting hydrophilic- or hydrophobic-modified polymer.
Claim 3
Dependent Claim
149 words
The method according to claim 1 wherein said alkenyl azlactone monomer has the formula ##STR10## wherein R 1 is hydrogen or methyl; R 2 is selected from a single bond or ##STR11## in which R 3 is alkylene having 1 to 12 carbon atoms preferably 1 to 6 carbon atoms, and W is --O--, --S-- or --NH--; R 4 and R 7 are independently selected from a single bond and methylene, or substituted methylene having 1 to 12 carbon atoms; R 5 and R 6 are independently alkyl or cycloalkyl having 1 to 12 carbon atoms, aryl or aralkyl having 6 to 12 carbon atoms, or R 5 and R 6 taken together with the carbon to which they are joined form a 5- or 6-membered carbocyclic ring, or R 5 and R 6 may be H when at least one of R 4 and R 7 is methylene.
Claim 4
Dependent Claim
15 words
The method according to claim 2 wherein said alkenyl azlactone monomer is a 2-alkenyl-4,4-disubstituted 2-oxazolin-5-one.
Claim 5
Dependent Claim
82 words
The method according to claim 1 wherein said interpolymer has the formula ##STR12## wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 are as defined in claim 2, A and B are numbers representing mole percent, A being in the range of 50 to 99 mole percent, and B being in the range of 1 to 50 mole percent, the A and B units being randomly positioned in the interpolymer.
Claim 6
Dependent Claim
25 words
The method according to claim 1 wherein said mole percent of polymerizable monomer units in said interpolymer is in the range of 70 to 95.
Claim 7
Dependent Claim
30 words
The method according to claim 1 wherein said alkenyl azlactone monomer is selected from the group consisting of 2-vinyl-4,4-dimethyl-2-oxazolin-5-one, 2-isopropenyl-4,4-dimethyl-2-oxazolin-5-one, 2-vinyl-4,4-diethyl-2-oxazolin-5-one, 2-vinyl-4,4-dibutyl-2-oxazolin-5-one, 2-vinyl-4-methyl-4-nonyl-2-oxazolin-5-one, 2-vinyl-4-methyl-4-dodecyl-2-oxazolin-5-one, 2-isopropenyl-4-methyl-4-phenyl-2-oxazolin-5-one, 2-isopropenyl-4-methyl-4-benzyl-2-oxazolin-5-one, 2-vinyl-4,4-pentamethylene-2-oxazolin-5-one, 2-isopropenyl-4,4-tetramethylene-2-oxazolin-5-one, and 2-vinyl-4,4-dimethyl-1,3-oxazin-6-one.
Claim 8
Dependent Claim
34 words
The method according to claim 1 wherein said at least one polymerizable monomer is selected from the group consisting of styrene, methyl methacrylate, butyl methacrylate, iso-octyl acrylate, octadecyl acrylate, N,N-dimethylacrylamide, vinyl chloride, and N-vinylpyrrolidone.
Claim 9
Dependent Claim
13 words
The method according to claim 3 wherein said 2-alkenyl-4,4-disubstituted 2-oxazolin-5-one monomer is 2-vinyl-4,4-dimethyl-2-oxazolin-5-one.
Claim 10
Dependent Claim
29 words
The method according to claim 1 wherein said nucleophile is selected from the group consisting of (a) hydrophiles: 2-(2-methoxyethoxy)ethanol, methoxyethoxypropylamine, and methoxydiethoxypropylamine, and (b) hydrophobes: octadecylamine, N-methyl-N-(4-hydroxybutyl)perfluorooctanesulfonamide, and perfluoroheptylmethanol.
References Cited (Backward Citations)
US2839430A
Cited
US3510342A
Cited
US3475196A
Cited
US3511894A
Cited
US3471458A
Cited
US3583950A
Cited
US3488706A
Cited
US3563937A
Cited
US3551391A
Cited
US4109070A
Cited
US4228523A
Cited
US4304705A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-05-29 | 1987-11-28 | 1988-05-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-05-29 | 1991-11-28 | 1992-05-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-05-29 | 1995-11-28 | 1996-05-29 | $7700.00 | Window Closed / Lapsed |