US 4,485,211 AGranted

Poly(glycidyl ether)block copolymers and process for their preparation

AssigneeThe B. F. Goodrich Company

InventorYoshihisa Okamoto

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Abstract

Under particular conditions, a cationic ring-opening polymerization of a first oxirane monomer selected from the group consisting of an acyclic glycidyl ether, a cyclic glycidyl ether, and a haloalkyl epoxide, in the presence of a hydroxyl-containing organic material ("HCM"), for example a polymer (referred to herein as a `hydroxyl-prepolymer`), and a particular catalyst, produces a polymerization having `living polymerization` characteristics. The result is that molecular weight (mol wt) of the resulting polymer is directly proportional to the conversion of the monomer to said resulting polymer. This HCM serves as a chain propagator which initially furnishes OH groups as propagation sites. Subsequently, a second oxirane monomer, different from said first, is sequentially polymerized to yield a block copolymer. Branched block copolymers, or linear block copolymers of a HCM and (a) one or more glycidyl ethers, or (b) a haloalkyl epoxide and at least one glycidyl ether, may be prepared. Halogen containing segments of the block copolymers of the invention may be aminated to produce amphophilic polymers.

Claims29

Dependent claims

A block copolymer having at least one polyglycidyl ether block said block copolymer having the structure ##STR6## wherein, R.sup.1 represents the residue of a hydroxyl-containing material (HCM) selected from a first compound having from 1 to 4 terminal hydroxy (OH) propagating sites, including a first hydroxyl-terminated prepolymer having from 1 to 4 terminal OH propagating sites;

and, a second compound having from 1 to about 200 pendant OH propagating sites;
A is derived from a first glycidyl ether having the structure ##STR7## wherein each R is independently selected from the group consisting of hydrogen, alkyl, haloalkyl, oxyalkylene, oxyhaloalkylene, alkoxyalkyl, aryl (Ar) and substituted aryl (Ar--Q), wherein Q is selected from the group consisting of alkyl, haloalkyl each having from 1 to about 10 carbon atoms, alkenyl and haloalkenyl each having from 2 to about 10 carbon atoms;
and, unsaturated hydrocarbyl radicals,
B is derived from a second glycidyl ether having different substituents from those in said first glycidyl ether but also having structure (I);
C is derived from a haloalkyl epoxide;
when R.sup.1 is polyglycidyl ether residue,
(i) at least one of A or B, and C is present;
(ii) at least two glycidyl ethers arbitrarily selected from A and B are present;
and,
(iii) when C is present, at least one of A or B is present;
so that the molecular weight of the resulting block copolymer is directly proportional to the amount of monomer converted;
and, a, b, and c represent integers in the range from about 5 to about 100;
D represents an integer in the range from 1 to about 200;
so that the molecular weight of each of the segments of the copolymer is in the range from about 500 to about 10,000, the segments are present in a heterogenous relative order, and the molecular weight of the block copolymer is in the range from about 1000 to about 2,000,000.

11 more elements

A process for preparing a block copolymer having at least one polyglycidyl ether block, said block copolymer having the structure ##STR9## which process comprises polymerizing (i) a hydroxyl-containing organic material with (ii) a first glycidyl ether

A having the structure ##STR10## wherein each R is independently selected from the group consisting of hydrogen, alkyl, haloalkyl, oxyalkylene, oxyhaloalkylene, alkoxyalkyl, aryl (Ar) and substituted aryl (Ar--Q), wherein Q is selected from the group consisting of alkyl, haloalkyl each having from 1 to about 10 carbon atoms, alkenyl and haloalkenyl each having from 2 to about 10 carbon atoms;
and, unsaturated hydrocarbyl radicals;
B represents a second glycidyl ether having different substituents from those in said first glycidyl ether but also having structure (I);
C represents a haloalkyl epoxide;
when R.sup.1 is a polyglycidyl ether residue,
(i) at least one of A or B, and C is present;
(ii) at least two glycidyl ethers arbitrarily selected from A and B are present;
and,
(iii) when C is present, at least one of A or B is present;
so that the molecular weight of the resulting block copolymer is directly proportional to the amount of monomer converted;
and, a, b, and c represent integers in the range from about 5 to about 100;
D represents an integer in the range from 1 to about 200;
so that the molecular weight of each of the segments of the copolymer is in the range from about 500 to about 10,000, the segments are present in a heterogenous relative order, and the molecular weight of the block copolymer is in the range from about 1000 to about 2,000,000.

10 more elements

Dependencies are inferred from the claim text.