US4785070A
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US
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Imidazolinone-containing copolymer
Assignee: 3M Co
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Filing: 1987-02-17
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Granted: 1988-11-15
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Expires: 2007-02-17
Abstract
Abstract A novel class of heterocyclic polymers and copolymers containing the 2-imidazolin-5-one ring structure is described. These polymers are prepared by reaction of bisazlactones and diamines, with or without suitable condensation monomers; the resultant polyamides are then thermally cyclodehydrated in the presence of a catalyst to produce the imidazolinone-containing polymers. Many of the poly(imidazolinones) are water soluble and therefore find utility in various aspects of water treatment, or in paper or fabric sizing.
Inventors
- 👤 Jerald K. Rasmussen
- 👤 Alan R. Katritzky
- 👤 Larry R. Krepski
- 👤 II Howell K. Smith
- 👤 Steven M. Heilmann
- 👤 Kumars Sakizadeh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 01:07
CPC Classifications
C; C08; C08G; C08G73/00; C08G73/06; C08G73/0605; C08G73/0616; C08F; C08F220/00
Claims Analysis
Total Claims: 44
Claim 1
Independent Claim
26 words
A copolymer comprising one or more 2-imidazolin-5-one units of the formula ##STR20## in the polymer backbone and other units derived from at least one condensation monomer.
Claim 2
Dependent Claim
26 words
A copolymer comprising one or more 2-imidazolin-5-one units of the formula ##STR20## in the polymer backbone and other units derived from at least one condensation monomer.
Claim 3
Dependent Claim
213 words
A copolymer comprising (a) 0.5 to less than 100 mole percent of 2-imidazolin-5-one units having formula I ##STR21## wherein R 1 and R 2 independently represent an alkyl group of 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or R 1 and R 2 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring; R 3 is a divalent organic group having a number average molecular weight of up to 20,000 selected from the group consisting of (1) a hydrocarbyl group having 2 to 20 carbon atoms, (2) polyoxyalkylene, (3) polyamide, (4) polyester, (5) polyolefin, (6) polyacrylate, and (7) polysiloxane groups; and R 4 is a divalent organic group selected from the group consisting of ##STR22## wherein R 1 , R 2 , and X are as defined above and R 5 is a divalent organic group having a number average molecular weight up to 20,000, selected from the group consisting of (1) a hydrocarbyl group having 2 to 20 carbon atoms, (2) polyoxyalkylene, (3) polyester, (4) polyolefin, (5) polyacrylate, and (6) polysiloxane groups; and (b) 99.5 to more than 0 weight percent of other units derived from condensation monomers.
Claim 4
Dependent Claim
213 words
A copolymer comprising (a) 0.5 to less than 100 mole percent of 2-imidazolin-5-one units having formula I ##STR21## wherein R 1 and R 2 independently represent an alkyl group of 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or R 1 and R 2 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring; R 3 is a divalent organic group having a number average molecular weight of up to 20,000 selected from the group consisting of (1) a hydrocarbyl group having 2 to 20 carbon atoms, (2) polyoxyalkylene, (3) polyamide, (4) polyester, (5) polyolefin, (6) polyacrylate, and (7) polysiloxane groups; and R 4 is a divalent organic group selected from the group consisting of ##STR22## wherein R 1 , R 2 , and X are as defined above and R 5 is a divalent organic group having a number average molecular weight up to 20,000, selected from the group consisting of (1) a hydrocarbyl group having 2 to 20 carbon atoms, (2) polyoxyalkylene, (3) polyester, (4) polyolefin, (5) polyacrylate, and (6) polysiloxane groups; and (b) 99.5 to more than 0 weight percent of other units derived from condensation monomers.
Claim 5
Dependent Claim
24 words
The copolymer according to claim 2 in which R 1 and R 2 are independently selected from the group consisting of methyl and pentamethylene.
Claim 6
Dependent Claim
21 words
The copolymer according to claim 2 wherein R 3 is selected from the group consisting of alkylene, alkylene imine, and arylene.
Claim 7
Dependent Claim
24 words
The copolymer according to claim 2 wherein said condensation monomers are selected from the group consisting of dicarboxylic acids, and their anhydrides, and esters.
Claim 8
Dependent Claim
16 words
The polymer according to claim 2 which is comprised of units derived from tetramethylenebis(4,4-dimethyl-2-oxazolin-5-one) or p-phenylenebis(4,4-dimethyl-2-oxazolin-5-one).
Claim 9
Dependent Claim
14 words
The copolymer according to claim 2 wherein the a component is derived from tetramethylenebis(4,4-dimethyl-2-oxazolin-5-one).
Claim 10
Dependent Claim
19 words
The copolymer according to claim 2 wherein R 3 is selected from the group consisting of alkylene and arylene.
Claim 11
Dependent Claim
33 words
The copolymer according to claim 8 wherein said alkylene or arylene group is interrupted by one to five catenary heteroatoms selected from the group of atoms consisting of oxygen, nitrogen, silicon, and sulfur.
Claim 12
Dependent Claim
46 words
The copolymer according to claim 2 wherein any of the seven R 3 groups is substituted by at least one non-nucleophilic group selected from the class consisting of cyano, halo, ester, ether, keto, nitro, silyl, or sulfide, the carbon-containing groups having up to 10 carbon atoms.
Claim 13
Dependent Claim
16 words
The copolymer according to claim 2 wherein R 5 is an alkylene or an arylene group.
Claim 14
Dependent Claim
33 words
The copolymer according to claim 11 wherein said alkylene or arylene group is interrupted by one to five catenary heteroatoms selected from the group of atoms consisting of oxygen, nitrogen, silicon, and sulfur.
Claim 15
Dependent Claim
46 words
The copolymer according to claim 2 wherein any of the six R 5 groups are substituted by at least one non-nucleophilic group selected from the class consisting of cyano, halo, ester, ether, keto, nitro, silyl, or sulfide, the carbon-containing groups having up to 10 carbon atoms.
Claim 16
Dependent Claim
24 words
The copolymer according to claim 2 in which R 1 and R 2 are independently selected from the group consisting of methyl and pentamethylene.
Claim 17
Dependent Claim
21 words
The copolymer according to claim 2 wherein said condensation monomer is selected from the group consisting of aminocarboxylic acids and lactams.
Claim 18
Dependent Claim
21 words
The copolymer according to claim 2 wherein said condensation monomer is selected from the group consisting of hydroxycarboxylic acids and lactones.
Claim 19
Dependent Claim
25 words
The copolymer according to claim 2 wherein said condensation monomer is selected from the group consisting of a diol, polyether diol, and a polyester diol.
Claim 20
Dependent Claim
13 words
The copolymer according to claim 2 wherein said condensation monomer is a diisocyanate.
Claim 21
Independent Claim
291 words
The method for preparing a 2-imidazolin-5-one unit containing copolymer comprising the steps of (a) reacting (1) at least one azlactone-functional compound of the formula III ##STR23## wherein III R 1 and R 2 independently represent an alkyl group of 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or R 1 and R 2 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring, R 6 is ##STR24## where Y is HO--, R 7 O--, or CH 3 COO--, R 7 is lower alkyl of 1-4 carbon atoms, phenyl or phenyl substituted by at least one non-nucleophilic group, and R 5 is a divalent organic group having a number average molecular weight up to 20,000, selected from the group consisting of (1) a hydrocarbyl group having 2 to 20 carbon atoms, and (2) polyoxyalkylene, (3) polyester, (4) polyolefin, (5) polyacrylate, and (6) polysiloxane groups; (2) at least one condensation comonomer; and (3) with at least one nucleophilic group-substituted amine to provide a polyamide, said amine having formula II H.sub.2 N--R.sup.3 --XH II wherein X is ##STR25## --O--, or --S--, and R is hydrogen or an alkyl group of 1 to 12 carbon atoms or an aryl group of 6 to 12 carbon atoms, and R 3 having a number average molecular weight of up to 20,000 and is selected from the class consisting of (1) a hydrocarbyl group having 2 to 20 carbon atoms, and (2) polyoxylakylene, (3) polyamide, (4) polyester, (5) polyolefin, (6) polyacrylate, and (7) polysiloxane groups; and (b) thermally treating said resulting polyamide in the presence of a dehydration catalyst to provide said 2-imidazolin-5-one unit-containing polymer.
Claim 22
Independent Claim
291 words
The method for preparing a 2-imidazolin-5-one unit containing copolymer comprising the steps of (a) reacting (1) at least one azlactone-functional compound of the formula III ##STR23## wherein III R 1 and R 2 independently represent an alkyl group of 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or R 1 and R 2 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring, R 6 is ##STR24## where Y is HO--, R 7 O--, or CH 3 COO--, R 7 is lower alkyl of 1-4 carbon atoms, phenyl or phenyl substituted by at least one non-nucleophilic group, and R 5 is a divalent organic group having a number average molecular weight up to 20,000, selected from the group consisting of (1) a hydrocarbyl group having 2 to 20 carbon atoms, and (2) polyoxyalkylene, (3) polyester, (4) polyolefin, (5) polyacrylate, and (6) polysiloxane groups; (2) at least one condensation comonomer; and (3) with at least one nucleophilic group-substituted amine to provide a polyamide, said amine having formula II H.sub.2 N--R.sup.3 --XH II wherein X is ##STR25## --O--, or --S--, and R is hydrogen or an alkyl group of 1 to 12 carbon atoms or an aryl group of 6 to 12 carbon atoms, and R 3 having a number average molecular weight of up to 20,000 and is selected from the class consisting of (1) a hydrocarbyl group having 2 to 20 carbon atoms, and (2) polyoxylakylene, (3) polyamide, (4) polyester, (5) polyolefin, (6) polyacrylate, and (7) polysiloxane groups; and (b) thermally treating said resulting polyamide in the presence of a dehydration catalyst to provide said 2-imidazolin-5-one unit-containing polymer.
Claim 23
Dependent Claim
22 words
The method according to claim 19 wherein R 3 of said copolymer is selected from the group consisting of alkylene and arylene.
Claim 24
Dependent Claim
33 words
The method according to claim 20 wherein said alkylene or arylene group is interrupted by one to five catenary heteroatoms selected from the group of atoms consisting of oxygen, nitrogen, silicon, and sulfur.
Claim 25
Dependent Claim
46 words
The method according to claim 19 wherein any of the seven R 3 groups is substituted by at least one non-nucleophilic group selected from the class consisting of cyano, halo, ester, ether, keto, nitro, silyl, or sulfide, the carbon-containing groups having up to 10 carbon atoms.
Claim 26
Dependent Claim
19 words
The method according to claim 19 wherein R 5 of said copolymer is an alkylene or an arylene group.
Claim 27
Dependent Claim
33 words
The method according to claim 23 wherein said alkylene or arylene group is interrupted by one to five catenary heteroatoms selected from the group of atoms consisting of oxygen, nitrogen, silicon, and sulfur.
Claim 28
Dependent Claim
46 words
The method according to claim 19 wherein any of the six R 5 groups are substituted by at least one non-nucleophilic group selected from the class consisting of cyano, halo, ester, ether, keto, nitro, silyl, or sulfide, the carbon-containing groups having up to 10 carbon atoms.
Claim 29
Dependent Claim
27 words
The method according to claim 19 in which R 1 and R 2 of said copolymer are independently selected from the group consisting of methyl and pentamethylene.
Claim 30
Dependent Claim
23 words
The method according to claim 19 wherein said comonomer is selected from the group consisting of dicarboxylic acids, and their anydrides, and esters.
Claim 31
Dependent Claim
16 words
The method according to claim 19 wherein said dehydration catalyst is an acid or base catalyst.
Claim 32
Dependent Claim
25 words
The method according to claim 28 wherein said base catalyst is selected from the group consisting of metal salts of carboxylic acids, amines, and alkoxides.
Claim 33
Dependent Claim
20 words
The method according to claim 19 wherein said comonomer is selected from the group consisting of aminocarboxylic acids and lactams.
Claim 34
Dependent Claim
20 words
The method according to claim 19 wherein said comonomer is selected from the group consisting of hydroxycarboxylic acids and lactones.
Claim 35
Dependent Claim
25 words
The method according to claim 19 wherein said comonomer is selected from the group consisting of a diol, a polyether diol, and a polyester diol.
Claim 36
Dependent Claim
12 words
The method according to claim 19 wherein said comonomer is a diisocyanate.
Claim 37
Independent Claim
246 words
A method for preparing an intermediate polyamide comprising the steps of: reacting (a) at least one compound of the formula ##STR26## wherein W is --OH, R 7 O--, CH 3 COO--, or ##STR27## R 1 and R 2 independently represent an alkyl group of 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or R 1 and R 2 taken together with the carbon atom to which they are attached form a 5- to 12 -membered carbocyclic ring, R 5 is a divalent organic group having a number average molecular weight of up to 20,000, selected from the group consisting of (1) hydrocarbyl group having 2 to 20 carbon atoms, (2) polyoxyalkylene, (3) polyester, (4) polyolefin, (5) polyacrylate, and (6) polysiloxane groups, and R 7 is lower alkyl of 1 to 4 carbon atoms, phenyul or phenyl substituted by non-nucleophilic groups, with (b) at least one nucleophilic group-substituted amine having the formula H.sub.2 N--R.sup.3 --XH wherein X is ##STR28## --O--, or --S--, R is hydrogen or an alkyl group of 1 to 12 carbon atoms or an aryl group of 6 to 12 carbon atoms, and R 3 is a divalent organic group having a number average molecular weight of up to 20,000 selected from the group consisting of (1) hydrocarbyl group having 2 to 20 carbon atoms, (2) polyoxyalkylene, (3) polyamide, (4) polyester, (5) polyolefin, (6) polyacrylate, and (7) polysiloxane groups.
Claim 38
Independent Claim
246 words
A method for preparing an intermediate polyamide comprising the steps of: reacting (a) at least one compound of the formula ##STR26## wherein W is --OH, R 7 O--, CH 3 COO--, or ##STR27## R 1 and R 2 independently represent an alkyl group of 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, or R 1 and R 2 taken together with the carbon atom to which they are attached form a 5- to 12 -membered carbocyclic ring, R 5 is a divalent organic group having a number average molecular weight of up to 20,000, selected from the group consisting of (1) hydrocarbyl group having 2 to 20 carbon atoms, (2) polyoxyalkylene, (3) polyester, (4) polyolefin, (5) polyacrylate, and (6) polysiloxane groups, and R 7 is lower alkyl of 1 to 4 carbon atoms, phenyul or phenyl substituted by non-nucleophilic groups, with (b) at least one nucleophilic group-substituted amine having the formula H.sub.2 N--R.sup.3 --XH wherein X is ##STR28## --O--, or --S--, R is hydrogen or an alkyl group of 1 to 12 carbon atoms or an aryl group of 6 to 12 carbon atoms, and R 3 is a divalent organic group having a number average molecular weight of up to 20,000 selected from the group consisting of (1) hydrocarbyl group having 2 to 20 carbon atoms, (2) polyoxyalkylene, (3) polyamide, (4) polyester, (5) polyolefin, (6) polyacrylate, and (7) polysiloxane groups.
Claim 39
Dependent Claim
19 words
The method according to claim 34 wherein R 3 is selected from the group consisting of alkylene and arylene.
Claim 40
Dependent Claim
33 words
The method according to claim 35 wherein said alkylene or arylene group is interrupted by one to five catenary heteroatoms selected from the group of atoms consisting of oxygen, nitrogen, silicon, and sulfur.
Claim 41
Dependent Claim
46 words
The method according to claim 34 wherein any of the seven R 3 groups is substituted by at least one non-nucleophilic group selected from the class consisting of cyano, halo, ester, ether, keto, nitro, silyl, or sulfide, the carbon-containing groups having up to 10 carbon atoms.
Claim 42
Dependent Claim
16 words
The method according to claim 34 wherein R 5 is an alkylene or an arylene group.
Claim 43
Dependent Claim
33 words
The method according to claim 38 wherein said alkylene or arylene group is interrupted by one to five catenary heteroatoms selected from the group of atoms consisting of oxygen, nitrogen, silicon, and sulfur.
Claim 44
Dependent Claim
46 words
The method according to claim 34 wherein any of the six R 5 groups are substituted by at least one non-nucleophilic group selected from the class consisting of cyano, halo, ester, ether, keto, nitro, silyl, or sulfide, the carbon-containing groups having up to 10 carbon atoms.
References Cited (Backward Citations)
US3678005A
Cited
US4667012A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-11-15 | 1992-05-16 | 1992-11-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-11-15 | 1996-05-16 | 1996-11-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-11-15 | 2000-05-16 | 2000-11-15 | $7700.00 | Window Closed / Lapsed |