Reprocessable compositions

Patent metadata

Field	Value
Publication number	US-12030980-B2
Application number	US-202117538098-A
Country	US
Kind code	B2
Filing date	Nov 30, 2021
Priority date	Feb 1, 2021
Publication date	Jul 9, 2024
Grant date	Jul 9, 2024

Abstract

The present disclosure provides compositions comprising:
a) a copolymer prepared by a method comprising polymerizing in the presence of a metathesis catalyst:
i) a first monomer, wherein each instance of the first monomer is independently of the formula:

or salt thereof;
ii) a second monomer, wherein each instance of the second monomer is independently of the formula:

or a salt thereof;
iii) optionally a third monomer, wherein the third monomer is different from the first monomer and the second monomer; and iv) optionally a reprocessing catalyst; and

b) optionally the reprocessing catalyst;
wherein the reprocessing catalyst is a Brønsted acid, Lewis acid, Brønsted base, Lewis base, or a salt thereof;
provided that the composition comprises at least one of the reprocessing catalyst of iv) and the reprocessing catalyst of b).
The compositions may be reprocessed (e.g., remolded) under elevated temperature and/or elevated pressure.

First claim

What is claimed is:

1. A composition comprising:
a) a copolymer prepared by a method comprising polymerizing in the presence of a metathesis catalyst:
i) a first monomer, wherein each instance of the first monomer is independently of the formula:

or salt thereof, wherein:
each instance of Z is independently a single bond, C(R P ) 2 , or O;
each instance of R P is independently hydrogen, halogen, or substituted or unsubstituted, C 1-6 alkyl;
each instance of is independently a single or double bond;
each instance of R H is independently hydrogen, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —OR a , —OCN, —OC(═O)R a , —OC(═S)R a , —OC(═O)OR a , —OC(═O)N(R a ) 2 , —OS(═O)R a , —OS(═O)OR a , —OS(═O)N(R a ) 2 , —OS(═O) 2 R a , —OS(═O) 2 OR a , —OS(═O) 2 N(R a ) 2 , —OSi(R a ) 3 , —OSi(R a ) 2 (OR a ), —OSi(R a )(OR a ) 2 , —OSi(OR a ) 3 , oxo, —N(R a ) 2 , —N═C(R a ) 2 , ═NR a , —NC, —NCO, —N 3 , —NO 2 , —NR a C(═O)R a , —NR a C(═O)OR a , —NR a C(═O)N(R a ) 2 , —NR a S(═O)R a , —NR a S(═O)OR a , —NR a S(═O)N(R a ) 2 , —NR a S(═O) 2 R a , —NR a S(═O) 2 OR a , —NR a S(═O) 2 N(R a ) 2 , —SR a , —SCN, —S(═O)R a , —S(═O)OR a , —S(═O)N(R a ) 2 , —S(═O) 2 R a , —S(═O) 2 OR a , —S(═O) 2 N(R a ) 2 , —SeR a , halogen, —CN, —C(═NR a )R a , —C(═NR a )OR a , —C(═NR a )N(R a ) 2 , —C(═O)R a , —C(═O)OR a , —C(═O)SR a , —C(═S)OR a , or —C(═O)N(R a ) 2 ;
or the two instances of R H of one or more instances of

 are joined with the intervening carbon atoms to independently form a substituted or unsubstituted, monocyclic carbocyclic ring, substituted or unsubstituted, monocyclic heterocyclic ring, substituted or unsubstituted, monocyclic aryl ring, or substituted or unsubstituted, monocyclic heteroaryl ring; and
each instance of R a is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted, monocyclic carbocyclyl, substituted or unsubstituted, monocyclic heterocyclyl, substituted or unsubstituted, monocyclic aryl, substituted or unsubstituted, monocyclic heteroaryl, a nitrogen protecting group when attached to a nitrogen atom, an oxygen protecting group when attached to an oxygen atom, or a sulfur protecting group when attached to a sulfur atom, or two instances of R a are joined to form substituted or unsubstituted heterocyclyl or substituted or unsubstituted heteroaryl;
ii) a second monomer, wherein each instance of the second monomer is independently of the formula:

or a salt thereof, wherein:
each instance of Y is independently O or C(R Q ) 2 ;
each instance of R Q is independently hydrogen, halogen, or substituted or unsubstituted, C 1-6 alkyl;
each instance of R K is independently hydrogen, halogen, substituted or unsubstituted, C 1-10 alkyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or —OR N ;
each instance of R N is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted, C 1-10 alkyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or an oxygen protecting group;
each instance of j is independently 1, 2, or 3;
in Formula (B), each instance of k is independently 0, 1, 2, or 3; and
in Formula (B2):
W is silicon;
each instance of R Y is independently hydrogen, halogen, or substituted or unsubstituted, C 1-6 alkyl;
each instance of R Z is independently hydrogen, halogen, or substituted or unsubstituted, C 1-6 alkyl;
R K1 is hydrogen, halogen, substituted or unsubstituted, C 1-10 alkyl, substituted or unsubstituted, C 2-10 alkenyl, substituted or unsubstituted, C 2-10 alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, -L K1 -(substituted or unsubstituted carbocyclyl), -L K1 -(substituted or unsubstituted heterocyclyl), -L K1 -(substituted or unsubstituted aryl), -L K1 -(substituted or unsubstituted heteroaryl), or —OR N1 ;
L K1 is —O—, substituted or unsubstituted, C 1-10 alkylene, substituted or unsubstituted, C 2-10 heteroalkylene, substituted or unsubstituted carbocyclylene, substituted or unsubstituted heterocyclylene, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, or a combination thereof;
R N1 is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted, C 1-10 alkyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or an oxygen protecting group;
R K2 is halogen, substituted or unsubstituted, C 2-10 alkenyl, substituted or unsubstituted, C 2-10 alkynyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted heteroaryl, -L K2 -(substituted or unsubstituted carbocyclyl), -L K2 -(substituted or unsubstituted heterocyclyl), -L K2 -(substituted or unsubstituted aryl), or —OR N2 ;
L K2 is —O—, substituted or unsubstituted, C 1-10 alkylene, substituted or unsubstituted, C 2-10 heteroalkylene, substituted or unsubstituted carbocyclylene, substituted or unsubstituted heterocyclylene, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, or a combination thereof;
R N2 is independently hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted, C 1-10 alkyl, substituted or unsubstituted carbocyclyl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or an oxygen protecting group;
or R K1 and R K2 are joined with the intervening atom to form substituted or unsubstituted carbocyclyl or substituted or unsubstituted heterocyclyl; and
each instance of k is independently 1, 2, or 3;

iii) optionally a third monomer, wherein the third monomer is different from the first monomer and the second monomer; and
iv) optionally a reprocessing catalyst; and

b) optionally a reprocessing catalyst;
wherein the reprocessing catalyst is an unsubstituted C 2-20 alkanoic acid, a sulfonic acid, a sulfinic acid, a phosphoric acid, a phosphonic acid, a Lewis acid, a Lewis base, a urea, a thiourea, a carbamate, or a thiocarbamate;
provided that:
the reprocessing catalyst is not an ammonium halide; and
the composition comprises at least one of the reprocessing catalyst of iv) and the reprocessing catalyst of b).

2. A kit comprising:
a) a copolymer prepared by a method comprising polymerizing in the presence of a metathesis catalyst:
i) a first monomer, wherein each instance of the first monomer is independently of the formula:

or salt thereof, wherein:
each instance of Z is independently a single bond, C(R P ) 2 , or O;
each instance of R P is independently hydrogen, halogen, or substituted or unsubstituted, C 1-6 alkyl;
each instance of is independently a single or double bond;
each

Assignees

• Massachusetts Inst Technology

Inventors

• Johnson Jeremiah A
• Shieh Peyton
• Husted Keith
• Brown Christopher M
• Kristufek Samantha Lynn

Classifications

• C08G2261/70

  Post-treatment · CPC title

• C08G2261/418

  Ring opening metathesis polymerisation [ROMP] · CPC title

• C08G2261/3222

  containing one or more oxygen atoms as the only heteroatom, e.g. furan · CPC title

• C08G2261/314

  Condensed aromatic systems, e.g. perylene, anthracene or pyrene · CPC title

• C08G61/12

  Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule · CPC title