Photochemical preparation of hydroxyl-terminated polyisobutylenes and related methods and uses
AssigneeThe University of Akron
InventorsJoseph Kennedy, Nihan Nugay, Turgut Nugay
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Abstract
The present invention relates to novel hydroxyl-terminated polyisobutylenes and methods of making and using them. The hydroxyl-terminated polyisobutylenes contain a sulfur unit, —S—, within each terminal end group. The well-defined, sulfur containing, primary hydroxyl-terminated polyisobutylenes of the present invention can be simply, rapidly, and essentially quantitatively obtained by subjecting the unsaturated telechelic PIBs and mercapto alcohols to UV light-activated thiol-ene reactions. The resultant sulfur containing, primary hydroxyl-terminated polyisobutylenes can then be used in the production of polyurethanes and like materials.
Claims19
A telechelic polyisobutylene composition having at least one
- primary alcohol end group, a single sulfur atom being present within each of the at least one primary alcohol end group.
A telechelic polyisobutylene composition comprising the photochemical thiol-ene reaction product of:
- a polyisobutylene polymer having at least one end group selected from —CH2—CH(CH3)═CH2, —CH═C(CH3)2, and —CH2—CH═CH2 and combinations;
- and
- a mercapto alcohol, in the presence of UV light.
A polyurethane composition having improved hydrolytic-oxidative stability comprising the reaction products of:
- one or more telechelic polyisobutylenes having at least two alcohol-terminated end groups, the at least two alcohol-terminated end groups each having a single sulfur atom present therein;
- and
- one or more diisocyanates.
A method of making a telechelic polyisobutylene composition having one or more alcohol-terminated end groups, each having a single sulfur atom contained therein, the method comprising:
- (a) providing a polyisobutylene polymer having at least one end group selected from the end groups —CH2—CH(CH3)═CH2, —CH2═C(CH3)2, and CH2—CH═CH2, and combinations thereof;
- (b) combining the polyisobutylene polymer with a stoichiometricly sufficient quantity of a mercapto alcohol to provide a mixture;
- (c) irradiating the mixture with UV light.
A method for the production of a polyisobutylene-based polyurethane having improved hydrolytic-oxidative stability, the method comprising:
- (a) providing a photochemically-prepared telechelic polyisobutylene having at least two primary alcohol-terminated end groups, wherein a single sulfur atom is present within each of the primary alcohol-terminated end groups;
- and
- (b) adding a diisocyanate selected from the group consisting 4,4-methylene dicyclohexyl diisocyanate (HDMI), 4,4-methylene diphenyl diisocyanate (MDI),
- and combinations thereof, and a catalyst, to the photochemically-prepared telechelic polyisobutylene, to provide a polyurethane having improved hydrolytic-oxidative stability.
Dependencies are inferred from the claim text.