Method of manufacturing crystalline and amorphous forms of 6,6′-diphenyl-2,2′-bis(2-hydroxyethoxy)-1,1′-binaphthyl and thermoplastic resin therefrom

Patent metadata

Field	Value
Publication number	US-12540215-B2
Application number	US-202217587571-A
Country	US
Kind code	B2
Filing date	Jan 28, 2022
Priority date	Feb 27, 2019
Publication date	Feb 3, 2026
Grant date	Feb 3, 2026

Abstract

Methods for forming a crystalline form or an amorphous form of 6,6′-diphenyl-2,2′-bis(2-hydroxyethoxy)-1,1′-binaphthyl and thermoplastic resin therefrom. According to one embodiment, a crystal solvate form of 6,6′-diphenyl-2,2′-bis(2-hydroxyethoxy)-1,1′-binaphthyl, which contains in its crystals from 0.3 to 1.2 mol of an organic solvent per 1 mol of 6,6′-diphenyl-2,2′-bis(2-hydroxyethoxy)-1,1′-binaphthyl, where the organic solvent is selected from the group consisting of methanol, toluene, and methyl ethyl ketone.

First claim

The invention claimed is:

1 . A method of manufacturing a crystalline form A of 6,6′-diphenyl-2,2′-bis(2-hydroxyethoxy)-1,1′-binaphthyl, wherein the crystalline form A comprises less than 0.1 mol of organic solvents per 1 mol of 6,6′-diphenyl-2,2′-bis(2-hydroxyethoxy)-1,1′-binaphthyl and which in an X-ray powder diffraction diagram at 22° C. and Cu-Kα radiation displays the following three reflections, quoted as 20 values: 20.9±0.2°, 21.4±0.2° and 23.7±0.2°; and at least 3 of the following reflections, quoted as 2θ values: 6.5±0.2°, 8.6±0.2°, 11.0±0.2°, 13.2±0.2°, 14.9±0.2°, 16.2±0.2°, 17.3±0.2°, 17.8±0.2°, 18.4±0.2° and 19.0±0.2°; and
wherein the method comprises determining the contents of the solvent in the crystalline solvate form by gas chromatography and
obtaining the X-ray powder diffraction diagram of the crystalline solvate form at 22° C. using Cu-Kα radiation.

2 . The method of manufacturing the crystalline form of claim 1 , which in a DSC recorded according to ISO 11357-3:2018 at a heating rate of 20 K/min shows an endothermic peak having an onset in the range of 112-114° C. and a peak maximum in the range from 124-126° C.

3 . A method of manufacturing a crystalline form C of 6,6′-diphenyl-2,2′-bis(2-hydroxyethoxy)-1,1′-binaphthyl, wherein the crystalline form C comprises less than 0.1 mol of organic solvents per 1 mol of 6,6′-diphenyl-2,2′-bis(2-hydroxyethoxy)-1,1′-binaphthyl and which in an X-ray powder diffraction diagram at 22° C. and Cu-Kα radiation displays the following three reflections, quoted as 2θ values: 5.1±0.2°, 7.6±0.2° and 21.0±0.2°; and at least 3 of the following reflections, quoted as 2θ values: 8.2±0.2°, 9.2±0.2°, 10.4±0.2°, 10.8±0.2°, 11.6±0.2°, 12.8±0.2°, 13.4±0.2°, 14.5±0.2°, 15.2±0.2°, 15.6±0.2°, 16.6±0.2°, 17.4±0.2°, 17.9±0.2°, 18.5±0.2°, 19.2±0.2°, 19.9±0.2°, 20.4±0.2°, 21.8±0.2°, 22.2±0.2°, 22.6±0.2°, 13.4±0.2°, 24.0±0.2°, 25.7±0.2°, 27.3±0.2° and 27.9±0.2°; and
wherein the method comprises determining the contents of the solvent in the crystalline solvate form by gas chromatography, and
obtaining the X-ray powder diffraction diagram of the crystalline solvate form at 22° C. using Cu-Kα radiation.

4 . The method of manufacturing the crystalline form of claim 3 , which in a DSC recorded according to ISO 11357-3:2018 at a heating rate of 20 K/min shows an endothermic peak having an onset in the range of 112-114° C. and a peak maximum in the range from 124-126° C.

5 . The method of manufacturing the crystalline form of any one of claim 1 or 3 , wherein the crystals have an aspect ratio of at most 5:1.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Ikeda Shinya
• Kato Noriyuki
• Hirakawa Manabu
• Reuter Karl
• Andrushko Vasyl
• Kantor Mark
• Stolz Florian

Classifications

• C07B2200/13

  Crystalline forms, e.g. polymorphs · CPC title

• G02B1/041

  Lenses · CPC title

• C08G63/78

  Preparation processes · CPC title

• C08G63/66

  Polyesters containing oxygen in the form of ether groups (C08G63/42, C08G63/58 take precedence) · CPC title

• C07C43/202

  the aromatic ring being a naphthalene · CPC title