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US 5,849,847 AGranted
Telechelic polystyrene/polyethylene copolymers and processes for making same
AssigneeFMC Corporation
InventorRoderic P. Quirk
Life of this patent
Estimating the term…
Abstract
Polyalkenylaromatic-polyethylene copolymers are prepared using protected functional organolithium initiators. Polymerization of an alkenylsubstituted aromatic monomer followed by ethylene, results in a protected functional block polystyrene-co-polyethylenyllithium. Termination with a functionalizing agent followed by deprotection produces polymeric products with high functionalization at the initiating chain-end and at least partial functionalization at the terminal chain-end.
Claims109
A copolymer having the formula:
- FG--(A).sub.y (B).sub.z --(Q).sub.n --Z--J--Y(R.sup.1 R.sup.2 R.sup.3)!.sub.x (I)
- wherein:
- FG is H or a protected or non-protected functional group;
- each A and B is a hydrocarbyl group, one of which is derived by incorporation of one or more alkenylsubstituted aromatic compounds, and the other of which is derived by incorporation of ethylene;
- y and z represent the equivalents of A and B employed, respectively, and are integers from 10 to 200;
- Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic compounds, and mixtures thereof;
- n is an integer from 0 to 5;
- Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups;
- J is oxygen, sulfur, or nitrogen;
- Y(R.sup.1 R.sup.2 R.sup.3)!.sub.x is a protecting group, in which Y is an element selected from Group IVa of the Periodic Table of Elements;
- R.sup.1, R.sup.2, and R.sup.3 are each independently selected from the group consisting of hydrogen, alkyl, substituted alkyl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, aryl or substituted aryl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, and cycloalkyl and substituted cycloalkyl containing 5 to 12 carbon atoms;
- and
- x is dependent on the valence of J and varies from one when J is oxygen or sulfur to two when J is nitrogen.
10 more elements
A polymer produced by polymerizing ethylene singly to form a homopolymer, or in admixture with or sequentially with one or more alkenylsubstituted aromatic compound comonomers to form a random or block copolymer, respectively, with a protected functional organometallic initiator of the formula
- M--Q.sub.n --Z--J--Y(R.sup.1 R.sup.2 R.sup.3)!.sub.x (II)
- wherein:
- M is an alkali metal;
- Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic compounds, and mixtures thereof;
- n is an integer from 0 to 5;
- Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups;
- Y is an element selected from Group IVa of the Periodic Table of Elements;
- J is oxygen, sulfur, or nitrogen;
- R.sup.1, R.sup.2, and R.sup.3 are each independently selected from hydrogen, alkyl, substituted alkyl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, aryl or substituted aryl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, and cycloalkyl and substituted cycloalkyl containing 5 to 12 carbon atoms;
- and
- x is dependent on the valence of J and varies from one when J is oxygen or sulfur to two when J is nitrogen, to form a mono-protected, mono-functionalized living polymer, followed by quenching or functionalizing the living polymer with a functionalizing group to terminate and end-cap said living polymer.
8 more elements
A multi-branched or star-shaped polymer having at least one functional end produced by polymerizing ethylene singly, or sequentially or as mixture thereof with one or more alkenylsubstituted aromatic compound comonomers, with a protected functional organometallic initiator, having the formula:
- M--Q.sub.n --Z--J--Y(R.sup.1 R.sup.2 R.sup.3)!.sub.x (II)
- wherein:
- M is an alkali metal;
- Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic compounds, and mixtures thereof;
- n is an integer from 0 to 5;
- Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups;
- Y is an element selected from Group IVa of the Periodic Table of Elements;
- J is oxygen, sulfur, or nitrogen;
- R.sup.1, R.sup.2, and R.sup.3 are each independently selected from hydrogen, alkyl, substituted alkyl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, aryl or substituted aryl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, and cycloalkyl and substituted cycloalkyl containing 5 to 12 carbon atoms;
- and
- x is dependent on the valence of J and varies from one when J is oxygen or sulfur to two when J is nitrogen, to form a mono-protected, mono-functionalized living polymer;
- and
- coupling said living polymer with at least one other living polymer with a linking agent.
10 more elements
A process for preparing polymers including ethylene as a component thereof, comprising:
- polymerizing ethylene singly, as an admixture with an alkenylsubstituted aromatic hydrocarbon, or sequentially with one or more alkenylsubstituted aromatic compound comonomers, with a protected functional organometallic initiator of the formula
- M--Q.sub.n --Z--J--Y(R.sup.1 R.sup.2 R.sup.3)!.sub.x (II)
- wherein:
- M is an alkali metal;
- Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic compounds, and mixtures thereof;
- n is an integer from 0 to 5;
- Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups;
- J is oxygen, sulfur, or nitrogen;
- Y is an element selected from Group IVa of the Periodic Table of Elements;
- R.sup.1, R.sup.2, and R.sup.3 are each independently selected from hydrogen, alkyl, substituted alkyl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, aryl or substituted aryl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, and cycloalkyl and substituted cycloalkyl containing 5 to 12 carbon atoms;
- and
- x is dependent on the valence of J and varies from one when J is oxygen or sulfur to two when J is nitrogen, to form a mono-protected, mono-functionalized living polymer.
9 more elements
A process for preparing a multi-branched or star-shaped polymer, comprising:
- polymerizing ethylene singly, as an admixture with an alkenylsubstituted aromatic hydrocarbon, or sequentially with one or more alkenylsubstituted aromatic compound comonomers, with a protected functional organometallic initiator of the formula
- M--Q.sub.n --Z--J--Y(R.sup.1 R.sup.2 R.sup.3)!.sub.x (II)
- wherein:
- M is an alkali metal;
- Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic compounds, and mixtures thereof;
- n is an integer from 0 to 5;
- Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups;
- J is oxygen, sulfur, or nitrogen;
- Y is an element selected from Group IVa of the Periodic Table of Elements;
- R.sup.1, R.sup.2, and R.sup.3 are independently selected from hydrogen, alkyl, substituted alkyl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, aryl or substituted aryl groups containing lower alkyl, lower alkylthio, and lower dialkylamino groups, and cycloalkyl and substituted cycloalkyl containing 5 to 12 carbon atoms;
- and
- x is dependent on the valence of J and varies from one when J is oxygen or sulfur to two when J is nitrogen, to form a mono-protected, mono-functionalized living polymer;
- and
- coupling said living polymer with at least one other living polymer with a linking agent.
11 more elements
A copolymer having the formula
- FG--(A).sub.y (B).sub.z --(Q).sub.n --Z--J(H).sub.x
- wherein:
- FG is H or a protected or non-protected functional group;
- each A and B is a hydrocarbyl group, one of which is derived by incorporation of one or more alkenylsubstituted aromatic compounds, and the other of which is derived by incorporation of ethylene;
- y and z represent the equivalents of A and B employed, respectively, and are integers from 10 to 200;
- Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic compounds, and mixtures thereof;
- n is an integer from 0 to 5;
- Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups;
- J is oxygen, sulfur, or nitrogen;
- and
- x is dependent on the valence of J and varies from one when J is oxygen or sulfur to two when J is nitrogen.
8 more elements
A copolymer having the formula
- FG--(A).sub.y (B).sub.z --(Q.sub.n)--Z--J--X
- wherein:
- FG is H or a protected or non-protected functional group;
- each A and B is a hydrocarbyl group, one of which is derived by incorporation of one or more alkenylsubstituted aromatic compounds, and the other of which is derived by incorporation of ethylene;
- y and z represent the equivalents of A and B employed, respectively, and are integers from 10 to 200;
- Q is a saturated or unsaturated hydrocarbyl group derived by incorporation of a compound selected from the group consisting of conjugated diene hydrocarbons, alkenylsubstituted aromatic compounds, and mixtures thereof;
- n is an integer from 0 to 5;
- Z is a branched or straight chain hydrocarbon group which contains 3-25 carbon atoms, optionally containing aryl or substituted aryl groups;
- J is oxygen, sulfur, or nitrogen;
- and
- X is a polymer segment derived by reaction of a comonomer with J.
8 more elements
Dependencies are inferred from the claim text.