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Liquid photo initiating compound and uses of the same

a technology of initiating compound and liquid photo, which is applied in the field of liquid photo initiating compound, can solve the problems of poor solubility of most UV inks, prone to precipitation of irgacure® 369, and require additional grinding and heating processes, and achieve the effect of improving all the aforementioned defects

Active Publication Date: 2019-08-20
CHITEC TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a photoinitiator derived from oxazolidine that has several advantages over conventional liquid photoinitiators for the black ink system. It is a liquid at a low temperature of 50°C, has high solubility in various monomers and oligomers, is odorless, and does not have acute oral toxicity. Furthermore, it complies with industry requirements for liquid photoinitiators with regards to light color and high purity. The technical effects of the present invention include improved performance, odorlessness, and safety.

Problems solved by technology

However, it suffers from poor solubility in most UV inks and thus requires additional grinding and heating processes to facilitate dissolution.
Even though, Irgacure® 369 is prone to precipitate when dosage is over 4 wt % and when handled in cold areas.
Still, it is not easy to use in its solid form that requires grinding and heating processes in order to dissolve into an ink composition.
Furthermore, Irgacure® 379 also has reproductive toxicity.
A photoinitiator in liquid form with high solubility is therefore highly desired to the low viscosity ink as these inks do not provide sufficient shearing force to perform the grinding and dispersion processes for solid photoinitiators.
But these compounds are not commercialized because their poor photospeeds as well as odor issues.
Even though the liquid photoinitiator is odorless, it is not commercialized due to its poor photo speed which is about one tenth that of Irgacure® 369.
Unfortunately, the compound I has a serious odor issue after curing.
However, the compound IIa has high acute oral toxicity.
Besides, it is in dark-brown color which is not satisfactory for some colors.
Therefore, conventional liquid photoinitiators with individual defects for dark and black inks are far from satisfactory.

Method used

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  • Liquid photo initiating compound and uses of the same
  • Liquid photo initiating compound and uses of the same
  • Liquid photo initiating compound and uses of the same

Examples

Experimental program
Comparison scheme
Effect test

example 1

on of Liquid Photo Initiating Compound Represented by Formula Ia

[0058]34 g 2-(dimethylamino)-1-[4-[(2-hydroxyethyl)amino]phenyl]-2-(phenylmethyl)-1-butanone (CAS 862589-48-8); the synthesis method of it may refer to TW 1277834), 13.0 g 2,2-dimethoxybutane (CAS 3453-99-4), 0.17 g PTSA (p-toluenesulfonic acid), and 100 mL toluene were added in sequence to a 250 mL three-necked flask at room temperature and then the reaction as shown below was carried out at reflux. The by-product methanol produced by this reaction was removed by Dean-Stark evaporator.

[0059]

[0060]The reaction was monitored by High Performance Liquid Chromatography (HPLC). After the reaction was completed, the reaction product was cooled to room temperature and washed with 17 g pure water for three times. The organic layer was collected and then concentrated under vacuum to obtain the compound represented by Formula Ia (hereinafter “photo initiating compound Ia”) as a yellowish and viscous liquid. The yield is 95%.

[0061...

example 2

on of a Liquid Photo Initiating Compound Represented by Formula Ib

[0063]34 g 2-(dimethylamino)-1-[4-[((2-hydroxyethyl)amino]phenyl]-2-(phenylmethyl)-1-butanone, 12.0 g 2,2-dimethoxypropane (CAS 77-76-9), 0.17 g PTSA (p-toluenesulfonic acid), and 100 mL toluene were added to a 250 mL three-necked flask at room temperature in sequence and the reaction as shown below was carried out at a condition the same as the previous example.

[0064]

[0065]The reaction was monitored by High Performance Liquid Chromatography (HPLC). After the reaction was completed, the reaction product was extracted with 17 g pure water for three times. The organic layer was collected and then concentrated under vacuum to obtain the compound represented by Formula Ib (hereinafter referred to as “photo initiating compound Ib”) as a yellowish and viscous liquid. The yield is 93%.

[0066]The photo initiating compound Ib was subjected to nuclear magnetic resonance analysis, and the results are as follows:

[0067]

Nuclear 1H N...

example 3

y Test

[0068]Mixtures I to III were prepared according to the composition provided below, and then 6 parts by weight of photoinitiator Trgacure® 369 (available from IGM), photoinitiator R-gen® 919 (available from Chitec Technology Co., Ltd.) or photo initiating compound Ia was added to each of the mixtures I to III. The obtained mixtures were ultrasonicated for 1 hour at room temperature, and the dissolution of each of Irgacure® 369, R-gen® 919 and photo initiating compound Ia was observed and described in the following Table 1.

[0069]

Mixture I: a mixture of 50 parts by weight of 1,6-hexanediol diacrylate (product name: EM221, Eternal MaterialsCo., Ltd.) and 50 parts by weight of polyestertetraacrylate (product name: Oligomer 6325-100, Eternal Materials Co., Ltd.) with a viscosity of 41.2 cPMixture II:a mixture of 50 parts by weight of trimethylolpropane triacrylate (product name: EM231, Eternal MaterialsCo., Ltd.) and 50 parts by weight of polyestertetraacrylate (product name: Oligom...

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Abstract

A liquid photo initiating compound and uses of the same are provided. The compound is represented by the following Formula I:in Formula I, R1 and R2 are independently H or C1-C3 alkyl, and R3 is H or methyl.

Description

CLAIM FOR PRIORITY[0001]This application claims the benefit of Taiwan Patent Application No. 107124654 filed on Jul. 17, 2018, the subject matters of which are incorporated herein in their entirety by reference.BACKGROUND OF THE INVENTIONField of the Invention[0002]The present invention relates to a liquid photo initiating compound and photopolymerizable compositions using the same.Descriptions of the Related Art[0003]A photoinitiator is a substance that forms free radicals via Norrish Type I photo-fragmentation after absorbing the energy of visible or UV light, which can initiate polymerization of monomers or oligomers to provide a curing effect.[0004]In 1990, Ciba Specialty Corporation introduced Irgacure® 369, which is the first photoinitiator specifically designed for dark color UV ink (related patent: U.S. Pat. No. 5,077,402). Irgacure® 369 is in solid form and its structure is shown below.[0005][0006]Irgacure® 369 has an outstanding photo speed and other advantages like odorle...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C08F2/46C08K5/06C08G61/04C08F2/50C08K5/08C08F20/18C08K5/353C08K5/5397
CPCC08K5/06C08F2/50C08K5/08C08K5/353C08K5/5397C08F20/18C07D263/04C08F2/48G03F7/031G03F7/027C07D263/06
Inventor CHANG, WEI-CHUNCHIU, CHINGFAN CHRISWU, HUANG-MIN
Owner CHITEC TECH
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