# US 10,766,842 B2 · Anhydrosugar alcohol composition having enhanced storage stability, and anhydrosugar alcohol storage method

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- Number: US 10,766,842 B2
- Document ID: US10766842B2
- Status: Granted
- Kind: B2
- Application number: 15/779,688
- Filed: 2016-10-25
- Published: 2019-09-19
- Granted: 2020-09-08
- Earliest claimed: 2015-11-30
- Assignees: Samyang Corporation
- Applicants: Samyang Corporation
- Inventors: Hoon Ryu; Seung Hyun Yoo; Hyun Seung Lee; Jun Seop Im; Young Jae Jung
- Web page: https://patentgrep.com/patent/US10766842B2

## CPC

- C07C 29/94: Use of additives, e.g. for stabilisation
- A61K 8/49: containing heterocyclic compounds
- A61K 31/135: having aromatic rings {, e.g. ketamine, nortriptyline (methadone A61K31/137)}
- A61K 31/34: having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K 47/18: Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- C07C 29/84: by extractive distillation
- C07C 31/26: Hexahydroxylic alcohols
- C07D 211/12: with only hydrogen atoms attached to the ring nitrogen atom
- C07D 233/58: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
- C07D 307/62: Three oxygen atoms, e.g. ascorbic acid
- C07D 487/04: Ortho-condensed systems
- C07D 493/04: Ortho-condensed systems
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to an anhydrosugar alcohol composition having enhanced storage stability, and an anhydrosugar alcohol storage method, and more specifically, to an anhydrosugar alcohol composition having enhanced storage stability by comprising anhydrosugar alcohol and an amine-based additive; and to a method by which anhydrosugar alcohol having excellent quality may be provided by having the storing of the anhydrosugar alcohol performed under the existence of the amine-based additive, thereby remarkably enhancing the storage stability of the anhydrosugar alcohol.

## Claims

### Claim 1

A composition comprising
a concentrated anhydrosugar alcohol; and
an amine compound as an additive for stabilization;
wherein the concentrated anhydrosugar alcohol is dianhydrohexitol in solid form,
wherein the amine compound is selected from the group consisting of piperidine, 1,8-diazabicycloundec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene and combinations thereof, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of linear or branched C1-C10alkyl, C3-C10cycloalkyl, aminoC1-C10alkyl, mono- or di-C1-C10alkylaminoC1-C10alkyl, carboxamide and amino, and
wherein an amount of the amine compound is 1 ppm or more and 300 ppm or less, based on a weight of the concentrated anhydrosugar alcohol.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the amine compound has a pKa of 8 to 15.

### Claim 3 (depends on 1)

The composition of claim 1, which shows a transmittance of 90% or higher to ultraviolet (UV) light with 275 nm wavelength when diluted as an aqueous solution of 20% by weight concentration.

### Claim 4 (depends on 1)

The composition of claim 1, which shows a pH of 6 to 8 when diluted as an aqueous solution of 20% by weight concentration.

### Claim 5

A method for storing concentrated anhydrosugar alcohol, wherein the concentrated anhydrosugar alcohol is mixed with an amine compound as an additive for stabilization and the storage thereof is conducted,
wherein the concentrated anhydrosugar alcohol is dianhydrohexitol in solid form,
wherein the amine compound is selected from the group consisting of piperidine, 1,8-diazabicycloundec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene and combinations thereof, each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of linear or branched C1-C10alkyl, C3-C10cycloalkyl, aminoC1-C10alkyl, mono- or di-C1-C10alkylaminoC1-C10alkyl, carboxamide and amino, and
wherein an amount of the amine compound mixed with the concentrated anhydrosugar alcohol is 1 ppm or more and 300 ppm or less, based on a weight of the concentrated anhydrosugar alcohol.

### Claim 6 (depends on 5)

The method for storing concentrated anhydrosugar alcohol of claim 5, wherein the concentrated anhydrosugar alcohol stored is that obtained by distilling a dehydration reaction product liquid resulting from dehydration reaction of hexitol, purifying the distillation product, and then concentrating the purified product.

### Claim 7 (depends on 6)

The method for storing concentrated anhydrosugar alcohol of claim 6, wherein an acid catalyst is used in the dehydration reaction of hexitol.

### Claim 8 (depends on 6)

The method for storing concentrated anhydrosugar alcohol of claim 6, wherein the distillation is conducted by using a thin-film evaporator.

### Claim 9 (depends on 6)

The method for storing concentrated anhydrosugar alcohol of claim 6, wherein the purification is conducted by one or more processes selected from crystallization, decolorization, cation exchange resin treatment or anion exchange resin treatment.

### Claim 10 (depends on 6)

The method for storing concentrated anhydrosugar alcohol of claim 6, wherein in the purification, crystallization of the distillation product, decolorization of the crystallization product, and cation exchange resin treatment followed by anion exchange resin treatment of the decolorization product are conducted subsequently.

### Claim 11 (depends on 6)

The method for storing concentrated anhydrosugar alcohol of claim 6, wherein the concentration is conducted at a temperature of 90° C. to 110° C. under a pressure condition of 10 mmHg to 100 mmHg for 30 minutes or longer.
