Cyclic polyolefins derived from hexyne, octyne, nonyne, pentadecyne and their copolymers with acetylene

Patent metadata

Field	Value
Publication number	US-11155653-B2
Application number	US-202016792963-A
Country	US
Kind code	B2
Filing date	Feb 18, 2020
Priority date	Sep 22, 2017
Publication date	Oct 26, 2021
Grant date	Oct 26, 2021

Abstract

Disclosed are saturated cyclic monopolymers derived from hexyne, octyne, nonyne, pentadecyne and saturated cyclic copolymers derived from acetylene and a second alkyne monomer that is hexyne, octyne, nonyne, or pentadecyne.

First claim

What is claimed is:

1. A composition comprising a saturated cyclic homopolymer having a structural formula:

wherein: R is n-hexyl, or n-heptyl;
wherein the saturated cyclic homopolymer is formed by incorporation of a single type of alkyne monomers;
n is an integer greater than or equal to 1; and
m is an integer greater than or equal to 1.

2. The composition of claim 1 , wherein the single type of alkyne monomers is selected from the group consisting of 1-hexyne, 1-octyne, and 1-nonyne.

3. The composition of claim 1 , wherein a relative purity of the saturated cyclic homopolymer determined by an NMR analysis is about 75% to about 99%.

4. A method of preparing a saturated cyclic polymer comprising:
hydrogenating an unsaturated cyclic polymer using a hydrogenation catalyst to produce a saturated cyclic polymer;
wherein the saturated cyclic polymer comprises a saturated cyclic homopolymer or a saturated cyclic copolymer;
wherein the saturated cyclic homopolymer has a structural formula:

wherein: R is n-butyl, n-hexyl, n-heptyl, or n-tridecyl;
and
wherein the saturated cyclic copolymer has a structural formula:

wherein: R′ is n-butyl, n-hexyl, n-heptyl, or n-tridecyl;
when R′ is n-hexyl, a molar ratio of incorporated acetylene to incorporated second alkyne monomer is from 34 to 59: 41 to 66;
when R′ is n-heptyl, a molar ratio of incorporated acetylene to incorporated second alkyne monomer is from 15 to 43: 57 to 85;
n is an integer greater than or equal to 1; n′ is an integer greater; and
m′ is an integer greater than or equal to 1.

5. The method of claim 4 , wherein the saturated cyclic homopolymer is derived from a monomer selected from the group consisting of 1-hexyne, 1-octyne, 1-nonyne, and 1-pentadecyne.

6. The method of claim 4 , wherein the saturated cyclic copolymer is derived from acetylene and a second alkyne monomer selected from the group consisting of 1-hexyne, 1-octyne, 1-nonyne, and 1-pentadecyne.

7. The method of claim 6 , wherein the acetylene and the second alkyne monomer are randomly incorporated in the saturated cyclic copolymer at a variable ratio of comonomer units.

8. The method of claim 4 comprising purifying the saturated cyclic polymer, wherein the saturated cyclic polymer has a relative purity of about 75% to about 99% that is determined by a nuclear magnetic resonance spectroscopy (NMR) analysis.

Assignees

• Univ Florida

Inventors

• Veige Adam S

Classifications

• C08F4/22

  of chromium, molybdenum or tungsten · CPC title

• C08F38/00 Primary

  Homopolymers and copolymers of compounds having one or more carbon-to-carbon triple bonds · CPC title

• C08F8/04

  Reduction, e.g. hydrogenation · CPC title

• C08F2800/10

  as molar percentages · CPC title

• C08F138/00

  Homopolymers of compounds having one or more carbon-to-carbon triple bonds · CPC title