Thermoplastic graft elastomers via reactive compatibilization of polyacrylated epoxidized high oleic soybean oil and polydiene-containing copolymers
OwnerEric W. COCHRAN, R. Chris WILLIAMS +4inventors
InventorsEric W. COCHRAN, R. Chris WILLIAMS, Nacu HERNANDEZ, Austin HOHMANN, Baker W. KUEHL, Michael J. FORRESTER
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Abstract
The present application relates to a thermoplastic graft copolymer including one or more thermoplastic polymers of formula (I): and a branched chain thermoplastic polymer of formula (II): where R1, R1′, R2, R2′, R3, R4, R4′, AETAG, a, b, c, e, f, g, h, i, and j are as described herein. Also disclosed is the process for preparing the thermoplastic copolymer and its uses.
Claims34
A thermoplastic graft copolymer comprising:
- one or more thermoplastic polymers of formula I:
- and
- a branched chain thermoplastic polymer of formula II:
- where
- R1 and R1′ are independently selected at each occurrence thereof from the group consisting of H and methyl;
- R2 and R2′ are independently selected at each occurrence thereof from the group consisting of H, OH, halogen, —COOR5, —C(O)NR5R6, C1-C23 alkyl, and benzyl, where the C1-C23 alkyl can be optionally substituted with an aryl, heteroaryl, or heterocyclyl;
- R3 is independently selected at each occurrence thereof from the group consisting of —X—R7—X—, C1-C23 alkylene, arylene, and heteroarylene;
- R4 and R4′ are independently selected at each occurrence thereof from the group consisting of C1-C23 alkyl and benzyl, where the C1-C23 alkyl can be optionally substituted with an aryl, heteroaryl, heterocyclyl, carboxylic acid, oxirane, ester, thioester, or carbonotrithioate;
- R5 and R6 are independently selected at each occurrence thereof from the group consisting of H and C1-10 alkyl, hydoxyalkyl, or alkyloxirane;
- R7 is independently selected at each occurrence thereof from the group consisting of
- C1-23 alkyl, where the C1-C23 alkyl can be optionally substituted with an aryl, heteroaryl, or heterocyclyl;
- X is independently selected at each occurrence thereof from the group consisting of methylene, —NH—, or —O—.
- AETAG is a (meth)acrylated epoxidized triacyl glyceride;
- a, b, c, d, e, and f represent number average degrees of polymerization for repeat units of formula I that are distributed throughout the polymer chain in a statistically defined manner;
- a, b, c, d, e, and f range from 0 to 100,000, where a+b+c+d+e+f ranges from 100 to 200,000;
- g ranges from 1 to 5;
- h, i, and j represent number average degrees of polymerization for repeat units of formula II that are distributed throughout the polymer chain in a statistically defined manner;
- h ranges from 100 to 100,000;
- and
- i and j range from 0 to 100,000, where the thermoplastic polymer of formula I is grafted to the thermoplastic polymer of formula II.
A thermoplastic polymeric mixture comprising:
- one or more thermoplastic polymers of formula I:
- a branched chain thermoplastic polymer of formula II:
- and
- the graft copolymer of the present application;
- where
- R1 and R1′ are independently selected at each occurrence thereof from the group consisting of H and methyl;
- R2 and R2′ are independently selected at each occurrence thereof from the group consisting of H, OH, halogen, —COOR5, —C(O)NR5R6, C1-C23 alkyl, and benzyl, where the C1-C23 alkyl can be optionally substituted with an aryl, heteroaryl, or heterocyclyl;
- R3 is independently selected at each occurrence thereof from the group consisting of —X—R7—X—, C1-C23 alkylene, arylene, and heteroarylene;
- R4 and R4′ are independently selected at each occurrence thereof from the group consisting of C1-C23 alkyl and benzyl, where the C1-C23 alkyl can be optionally substituted with an aryl, heteroaryl, heterocyclyl, carboxylic acid, oxirane, ester, thioester, or carbonotrithioate;
- R5 and R6 are independently selected at each occurrence thereof from the group consisting of H and C1-10 alkyl, hydoxyalkyl, or alkyloxirane;
- R7 is independently selected at each occurrence thereof from the group consisting of
- C1-23 alkyl, where the C1-C23 alkyl can be optionally substituted with an aryl, heteroaryl, or heterocyclyl;
- X is independently selected at each occurrence thereof from the group consisting of methylene, —NH—, or —O—.
- AETAG is a (meth)acrylated epoxidized triacyl glyceride;
- a, b, c, d, e, and f represent number average degrees of polymerization for repeat units of formula I that are distributed throughout the polymer chain in a statistically defined manner;
- a, b, c, d, e, and f range from 0 to 100,000, where a+b+c+d+e+f ranges from 100 to 200,000;
- g ranges from 1 to 5;
- h, i, and j represent number average degrees of polymerization for repeat units of formula II that are distributed throughout the polymer chain in a statistically defined manner;
- h ranges from 100 to 100,000;
- and
- i and j range from 0 to 100,000, where the thermoplastic polymer of formula I is grafted to the thermoplastic polymer of formula II.
A method of forming a thermoplastic graft copolymer, said method comprising:
- mixing one or more thermoplastic polymers of formula I:
- with a branched chain thermoplastic polymer of formula II:
- where
- R1 and R1′ are independently selected at each occurrence thereof from the group consisting of H and methyl;
- R2 and R2′ are independently selected at each occurrence thereof from the group consisting of H, OH, halogen, —COOR5, —C(O)NR5R6, C1-C23 alkyl, and benzyl, where the C1-C23 alkyl can be optionally substituted with an aryl, heteroaryl, or heterocyclyl;
- R3 is independently selected at each occurrence thereof from the group consisting of —X—R7—X—, C1-C23 alkylene, arylene, and heteroarylene;
- R4 and R4′ are independently selected at each occurrence thereof from the group consisting of C1-C23 alkyl and benzyl, where the C1-C23 alkyl can be optionally substituted with an aryl, heteroaryl, heterocyclyl, carboxylic acid, oxirane, ester, thioester, or carbonotrithioate;
- R5 and R6 are independently selected at each occurrence thereof from the group consisting of H and C1-10 alkyl, hydoxyalkyl, or alkyloxirane;
- R7 is independently selected at each occurrence thereof from the group consisting of
- C1-23 alkyl, where the C1-C23 alkyl can be optionally substituted with an aryl, heteroaryl, or heterocyclyl;
- X is independently selected at each occurrence thereof from the group consisting of methylene, —NH—, or —O—.
- AETAG is a (meth)acrylated epoxidized triacyl glyceride;
- a, b, c, d, e, and f represent number average degrees of polymerization for repeat units of formula I that are distributed throughout the polymer chain in a statistically defined manner;
- a, b, c, d, e, and f range from 0 to 100,000, where a+b+c+d+e+f ranges from 100 to 200,000;
- g ranges from 1 to 5;
- h, i, and j represent number average degrees of polymerization for repeat units of formula II that are distributed throughout the polymer chain in a statistically defined manner;
- h ranges from 100 to 100,000;
- and
- i and j range from 0 to 100,000, where the thermoplastic polymer of formula I is grafted to the thermoplastic polymer of formula II;
- heating the blend;
- and
- extruding the heated blend to form a thermoplastic graft copolymer.
Dependencies are inferred from the claim text.