CN-117651742-B - Compounds using natural pigments

Abstract

The present invention provides a compound having a high biomass content (more preferably, a compound having a biomass content of 100%) obtained by using a natural pigment, and having excellent color development and light resistance. A compound formed by bonding natural pigment of curcumin and organic acid, wherein the number average molecular weight (Mn) of the compound is 400-4950.

Inventors

• OTSUBO Takahiko
• Guan Genjun
• Shan Bendun
• NEMOTO KOJI
• JI TIANSHENG
• SEKIYA AKIRA

Assignees

• DIC株式会社
• 国立研究开发法人产业技术综合研究所

Dates

Publication Date

20260512

Application Date

20220620

Priority Date

20210706

Claims (6)

1. 1. A compound obtained by bonding a natural pigment of curcumin with an organic acid, wherein the organic acid is a carboxylic acid having 2 or more carboxylic acid groups, and is capable of bonding with the curcumin to form a polymer of the natural pigment, the number average molecular weight of the compound, namely Mn, is 400-4950, and the compound is a natural pigment polymer.
2. 2. The compound according to claim 1, wherein the number average molecular weight, mn, of the compound is 600 to 4950.
3. 3. A compound obtained by bonding at least 1 or more natural pigments selected from alizarin, carminic acid, lac pigment or lac acid, capsanthin or capsanthin, hydroxysafflor yellow or safflower yellow, perillartine or perillartine pigment, and mycoflavin or monascus pigment, to an organic acid which is a carboxylic acid having 2 or more carboxylic acid groups capable of bonding to the natural pigments to form a polymer of the natural pigments, the compound being a natural pigment polymer, The number average molecular weight of the compound, namely Mn, is 300-100000.
4. 4. A compound according to claim 1 or 3, the organic acid being a dicarboxylic acid of natural origin.
5. 5. The compound according to claim 1 or 3, wherein the average particle diameter of the compound is 0.01 to 100 μm.
6. 6. A compound according to claim 1 or 3 for use as a colorant for inks, toners or paints.

Description

Compounds using natural pigments Technical Field The present invention relates to a compound using a natural pigment. Background In recent years, there has been a demand for an increasing call for the construction of a sustainable (sustainability) circulating society in consideration of the global environment, ecosystem, socioeconomic, and the like. The printing industry also desires to deviate from petrochemical resources, for example, non-toluene production of printing inks is being advanced for global environmental, biological, and security concerns. In addition, from the viewpoint of carbon neutralization, there is an increasing interest in replacing raw materials in the production of printing inks with biomass-derived chemicals, and studies on solvents and resins contained in the production of printing inks from biomass raw materials are being actively conducted. While the printing industry is also pushing environmental adaptation in this way, the current situation is limited to biomass of solvents and resins, and biomass of pigments has not been achieved. As a pigment used as a color material of a printing ink, a lake pigment obtained by precipitating a dye using a metal ion is widely used in view of excellent color development and light resistance. The method of precipitating a dye using metal ions discharges metal ions from wastewater at the time of production and purification, and thus requires a separate water discharge treatment step for removing metal ions. It is considered that the influence on the environment can be reduced by the separate drainage treatment step and the like. However, in the field of pigments, there is a demand for manufacturing products that take into account the global environment and the ecosystem, because of the recent increase in consumer awareness, by a method that has a lower possibility of affecting the environment. That is, it is desired to develop a pigment which can reliably prevent the discharge of metal ions and which is produced without using metal ions. As pigments produced without using metal ions, for example, bio-derived pigments such as pigments directly using algae have been reported (see patent document 1). Prior art literature Patent literature Patent document 1 U.S. patent application publication No. 2015/0243093 Disclosure of Invention Problems to be solved by the invention However, the pigment disclosed in patent document 1 is a pigment with a small environmental burden because it contains a bio-derived pigment produced without using metal ions, but is a pigment directly using algae, and therefore has a problem of insufficient color selectivity. The pigment disclosed in patent document 1 has inferior color development to conventional lake pigments in which a dye is precipitated using a metal ion. In addition, in order to be used as a colorant for ink, toner, and paint, various properties required for a color material such as color development and light resistance have been required, and it has been impossible to provide a compound excellent in color development and light resistance among compounds (for example, pigments) having a high biomass content using natural pigments. Accordingly, an object of the present invention is to provide an environmentally friendly compound that does not use a metal, particularly a compound having high biomass (more preferably, a compound having 100% biomass) obtained by using a natural pigment, and having excellent color development and light resistance. Means for solving the problems As a result of intensive studies to solve the above problems, the present inventors have found that a compound in which a specific natural pigment such as curcumin is bonded to an organic acid can solve the above problems, and have completed the present invention. That is, the present invention includes the following means. [1] A compound formed by bonding natural pigment of curcumin and organic acid, wherein the number average molecular weight (Mn) of the compound is 400-4950. [2] A compound which is obtained by bonding an organic acid to at least 1 natural pigment selected from alizarin, carminic acid, laccaine or laccaine, capsanthin or capsaicine, hydroxysafflor yellow or safflor yellow, perillyl or perillyl pigment, and at least 1 natural pigment selected from pyri, pyri-bil or perillyl pigment, and pyri-bil or perillyl pigment of red yeast コ. [3] The compound according to [1] or [2], wherein the organic acid has at least 1 or more carboxylic acid groups. [4] The compound according to [3], wherein the carboxylic acid is a carboxylic acid of natural origin. [5] The compound according to any one of [1] to [4], wherein the organic acid is any one of carboxylic acid, hydroxy acid and sulfonic acid. [6] The compound according to any one of [1] to [5], wherein the average particle diameter of the compound is 0.01 to 100. Mu.m. [7] The compound according to any one of [1] to [6], which is used as a colorant for ink, toner or paint. Effects o