Isomer-enriched 3-caranlactams and polyamides based thereon with high optical purity and adjustable crystallinity for high-performance applications

Patent metadata

Field	Value
Publication number	US-12152107-B2
Application number	US-201916978523-A
Country	US
Kind code	B2
Filing date	Mar 1, 2019
Priority date	Mar 9, 2018
Publication date	Nov 26, 2024
Grant date	Nov 26, 2024

Abstract

The present invention relates to a process for the preparation of an isomer-enriched mixture of 3S- and 3R-caranone from 3-carane epoxide, a 3S-caranone obtained therefrom, a process for the production of 3S-caranlactam from 3-carene, a process for the production of 3R-caranlactam from 3-carene, a 3S-caranoxime, a 3S-caranlactam, a 3S-polycaranamide, a 3R-polycaranamide, a 3S/3R-co-polycaranamide, a 3S-caranlactam-laurolactam co-polycaranamide, a 3R-caranlactam-laurolactam co-polycaranamide, a 3S-caranlactam-3R-caranlactam-laurolactam co-polycaranamide, a 3S-caranlactam-caprolactam co-polycaranamide, a 3R-caranlactam-caprolactam co-polycaranamide, as well as a 3S/3R-caranlactam-caprolactam co-polycaranamide.

First claim

The invention claimed is:

1. A polycaranamide, comprising a 3S-polycaranamide according to the formula:

or a 3R-polycaranamide according to the formula:

wherein n is a natural number greater than or equal to 2.

2. A polycaranamide, comprising a 3S/3R-co-polycaranamide according to the formula:

wherein a, b and n each is a natural number and n is greater than or equal to 2.

3. A plastic product comprising the polycaranamide according to claim 1 .

4. The plastic product of claim 3 , wherein the 3S-polycaranamide or the 3R-polycaranamide constitutes at least 5, 10, 15, 20, 30, 40, 50, 60, 70, 80, 90, 95 or 99 wt. % of the plastic product.

5. A plastic product comprising the polycaranamide according to claim 2 .

6. The plastic product of claim 5 , wherein the 3S/3R-co-polycaranamide constitutes at least 5, 10, 15, 20, 30, 40, 50, 60, 70, 80, 90, 95 or 99 wt. % of the plastic product.

Assignees

• Fraunhofer Ges Forschung

Inventors

• Stockmann Paul
• Strittmatter Harald
• Sieber Volker
• Falcke Claudia

Classifications

• C07D223/32

  containing carbocyclic rings other than six-membered · CPC title

• C07C251/44

  with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring · CPC title

• C07C225/10

  with doubly-bound oxygen atoms bound to carbon atoms not being part of rings · CPC title

• C07C2602/20

  the ring system containing seven carbon atoms · CPC title

• C07B2200/07

  Optical isomers · CPC title