Imidazolinone-containing copolymer
AssigneeMinnesota Mining and Manufacturing Company
InventorsJerald K. Rasmussen, Alan R. Katritzky, Larry R. Krepski, Howell K. Smith, II, Steven M. Heilmann, Kumars Sakizadeh
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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.
Claims40
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.
A copolymer comprising
- (a) 0.5 to less than 100 mole percent of 2-imidazolin-5-one units having formula I ##STR21## wherein R.sup.1 and R.sup.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.sup.1 and R.sup.2 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring;
- R.sup.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.sup.4 is a divalent organic group selected from the group consisting of ##STR22## wherein R.sup.1, R.sup.2, and X are as defined above and R.sup.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.
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.sup.1 and R.sup.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.sup.1 and R.sup.2 taken together with the carbon atom to which they are attached form a 5- to 12-membered carbocyclic ring,
- R.sup.6 is ##STR24## where Y is HO--, R.sup.7 O--, or CH.sub.3 COO--, R.sup.7 is lower alkyl of 1-4 carbon atoms, phenyl or phenyl substituted by at least one non-nucleophilic group, and R.sup.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.sup.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.
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.sup.7 O--, CH.sub.3 COO--, or ##STR27## R.sup.1 and R.sup.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.sup.1 and R.sup.2 taken together with the carbon atom to which they are attached form a 5- to 12 -membered carbocyclic ring,
- R.sup.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.sup.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.sup.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.
Dependencies are inferred from the claim text.