WO2019156378A1 - High-fastness disperse dye composition and method for dyeing fibers by using same - Google Patents

High-fastness disperse dye composition and method for dyeing fibers by using same Download PDF

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Publication number
WO2019156378A1
WO2019156378A1 PCT/KR2019/000643 KR2019000643W WO2019156378A1 WO 2019156378 A1 WO2019156378 A1 WO 2019156378A1 KR 2019000643 W KR2019000643 W KR 2019000643W WO 2019156378 A1 WO2019156378 A1 WO 2019156378A1
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Prior art keywords
dye composition
fibers
alkyl
formula
disperse dye
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PCT/KR2019/000643
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French (fr)
Korean (ko)
Inventor
박소영
김혜진
명성일
김정록
한지민
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(주)경인양행
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Priority to CN201980006938.5A priority Critical patent/CN111511981A/en
Publication of WO2019156378A1 publication Critical patent/WO2019156378A1/en

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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/16General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/54Polyesters using dispersed dyestuffs

Definitions

  • the present invention relates to a disperse dye composition and a method of dyeing fibers using the same, and more particularly, to a composition and a method of disperse dyes having excellent fastnesses such as daylight, water, and sublimation in dyeing polyester fibers.
  • Synthetic fibers such as acetate and polyester have a very high hydrophobicity as compared with conventional cellulose and protein fibers, making it very difficult to be dyed with conventional hydrophilic dyes.
  • the dyeing of such hydrophobic fibers does not contain water-soluble groups, and has been used as a disperse dye which is dispersed in water as a dye insoluble in water.
  • the disperse dyes cannot sufficiently realize excellent dyeing rate and high daylight fastness in view of their properties, and furthermore, the affinity of polyester to blended fibers and the like is not clear.
  • the inventors after extensive research and various experiments, described a method of dyeing a blended fiber material including polyester using a disperse dye composition containing a combination of specific compounds as described below. It has been developed, and in this case, it has been found that excellent dyeing rate and fastness can be obtained, and the present invention has been completed.
  • the problem to be solved by the present invention is to provide a disperse dye composition having excellent fastness by mixing disperse dyes in an appropriate ratio.
  • Another problem to be solved by the present invention is to provide a method for dyeing a blend fiber material containing a polyester or the like using the disperse dye composition, in this case, it is possible to obtain excellent fastness compared to the conventional dye have.
  • the present invention provides a dispersion dye composition comprising 1 to 99 parts by weight of the compound of Formula 1 and 1 to 99 parts by weight of the compound of Formula 2 to achieve the above object.
  • R 1 is a hydrogen atom or (C1-C18) alkyl
  • R 2 is (C1-C18) alkyl or-(CH 2 ) n -CO 2 R a )
  • n is an integer of 1 to 8
  • R a is (C1-C18) alkyl or (C1-C8) alkoxy (C1-C8) alkyl.
  • the disperse dye composition of the red series prepared with the compound of Formula 1 had a problem that it is difficult to express a dark color due to the dyeing concentration, the disperse fastness of the red series disperse dye prepared with the compound of Formula 2 was poor.
  • the dispersion dye composition according to the present invention can obtain a high dyeing concentration and excellent daylight fastness and sublimation fastness, water fastness grade of the level to be obtained through the combination of the compounds of formula 1 and 2 in a specific content.
  • R 1 is (C1-C8) alkyl
  • R 2 is (C1-C8) alkyl
  • n is an integer of 1 to 3
  • R a is (C1 ⁇ C8) alkyl or (C1-C4) alkoxy (C1-C4) alkyl.
  • the disperse dye composition may include 20 to 80 parts by weight of the compound of Formula 1 and 80 to 20 parts by weight of the compound of Formula 2.
  • composition of this invention can be added to the composition of this invention within the range which does not impair the objective and effect of this invention.
  • Such other additives may be added in the range of approximately 1 to 20 weight percent based on the total weight of the composition.
  • the solubilizer is an additive component that prevents agglomeration of dyes and helps dissolution, and typical examples thereof include urea, thiourea, and caprolactam.
  • the buffer is a component that buffers the pH to prevent degradation of the dye during storage and storage, and representative examples thereof include sodium phosphate, potassium phosphate, sodium acetate and the like.
  • the freezing inhibitor lowers the freezing point during liquid freezing and serves as a component that does not freeze the liquid dye. Representative examples include ethylene glycol, polyethylene glycol, and polyalcohol compounds.
  • the present invention also provides a method for dyeing a fiber material using the dispersion dye composition.
  • fibrous material examples include semisynthetic fibers, synthetic fibers, regenerated fibers, or blended fibers of synthetic fibers and natural fibers.
  • semisynthetic fibers include, for example, acetate, synthetic fibers such as polyester, polyamide, poly Vinyl, polyurethane-based fibers, recycled fibers include cellulose and the like.
  • the disperse dye composition is also applied to the dyeing of blended fibers of polyester fibers, for example blended fibers comprising polyester and cellulose fibers, and exhibits high dyeing rates and good fastnesses.
  • a method for dyeing a semi-synthetic fiber, synthetic fibers, regenerated fibers, or blended fibers of synthetic fibers and natural fibers using the dispersion dye composition is provided.
  • the dispersion dye composition using the dispersion dye composition, there is provided a method for dyeing polyester fiber or polyester composite fiber.
  • the blend fiber may include polyester fibers and cellulose fibers.
  • the disperse dye composition according to the present invention can be used in various methods, for example, cold pad placement method, continuous dyeing method, dyeing method, printing method, printing method, and preferably used in continuous dyeing method and dyeing method.
  • an acid-binding agent for example, sodium carbonate, sodium bicarbonate, etc.
  • a padding liquid padded by a known method and dyed by dry heat or steaming
  • inorganic Neutral salts e.g., anhydrous sodium sulfate, salt, etc.
  • acid binders e.g., caustic soda, sodium silicate, etc.
  • the dyeings and printings obtained according to the present invention are excellent in build-up and leveling. In addition, it is excellent in coloration, high fiber-dye bonding stability, and excellent in light fastness as well as prevention of contamination to other fibers.
  • the disperse dye composition according to the present invention includes a combination of specific compounds, it exhibits excellent dyeing rate when dyeing blended fiber materials including polyester and the like, and has excellent fastness such as sunlight, water, and sublimation.
  • the pH is adjusted after milling to a particle size of 1 ⁇ m or less 90% or more. Thereafter, spray dry drying to obtain a dispersion dye composition comprising a compound of formula (1).
  • Disperse dye composition comprising the composition of Preparation Example 2 was prepared as shown in Table 1.
  • Disperse dye compositions comprising the composition of Preparation Example 1, and the composition selected from the compositions of Preparation Examples 2 to 4 were prepared as shown in Table 1.
  • Daylight fastness was carried out by AATCC 16E method, water fastness was progressed by ISO-105-E01, and sublimation fastness by ISO-105-P01.

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  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Abstract

The present invention relates to a disperse dye composition comprising 1-99 parts by weight of a compound of chemical formula 1 below and 1-99 parts by weight of a compound of chemical formula 2 below, and to a method for dyeing semi-synthetic fibers, synthetic fibers, regenerated fibers, or mixed fibers of synthetic fibers and natural fibers, by using the disperse dye composition. The disperse dye composition according to the present invention comprises a combination of specific compounds, and thus the disperse dye composition shows an excellent dye adsorption rate when dyeing a mixed fiber material including polyester or the like, has excellent allround fastness, such as sunlight fastness, water fastness, and sublimation fastness, and enables the expression of high-density colors. [Chemical formula 1] [Chemical formula 2] In chemical formula 2, R1 is a hydrogen atom or (C1-C18)alkyl; R2 is (C1-C18)alkyl or -(CH2)n-CO2Ra; n is an integer of 1 to 8; and Ra is (C1-C18)alkyl or (C1-C8)alkoxy(C1-C8)alkyl.

Description

고견뢰도 분산염료 조성물 및 이를 이용한 섬유의 염색방법High fastness disperse dye composition and dyeing method of fibers using the same
본 출원은 2018.02.08.자로 출원된 한국 특허출원 제10-2018-0015697호에 기초한 우선권의 이익을 주장하며, 해당 한국 특허출원의 문헌에 개시된 모든 내용은 본 명세서의 일부로서 포함된다.This application claims the benefit of priority based on Korean Patent Application No. 10-2018-0015697, filed Feb. 8, 2018, and all contents disclosed in the documents of that Korean Patent Application are incorporated as part of this specification.
본 발명은 분산 염료 조성물 및 이를 이용한 섬유의 염색 방법에 관한 것이며, 보다 상세하게는 폴리에스터 섬유의 염색에서 일광, 물, 승화 등 제반 견뢰도가 우수한 분산 염료의 조성물 및 염색 방법에 관한 것이다.The present invention relates to a disperse dye composition and a method of dyeing fibers using the same, and more particularly, to a composition and a method of disperse dyes having excellent fastnesses such as daylight, water, and sublimation in dyeing polyester fibers.
아세테이트, 폴리에스테르 등의 합성 섬유는 종래의 셀룰로오스 및 단백질 섬유에 비하여 소수성이 매우 크기 때문에 종래의 친수성이 큰 염료에 의해 염색되기가 매우 힘들었다. 이러한 소수성 섬유의 염색은 수용성 그룹을 함유하지 않으며, 물에 녹지 않은 염료로서 물에 분산하여 이용하는 분산염료가 사용되어 왔다. Synthetic fibers such as acetate and polyester have a very high hydrophobicity as compared with conventional cellulose and protein fibers, making it very difficult to be dyed with conventional hydrophilic dyes. The dyeing of such hydrophobic fibers does not contain water-soluble groups, and has been used as a disperse dye which is dispersed in water as a dye insoluble in water.
그러나 분산염료는, 그 특성상 우수한 염착률 및 고일광 견뢰도를 충분히 실현할 수 없으며, 더욱이, 폴리에스테르의 혼방섬유 등에 대한 친화성도 명확하지 않다. However, the disperse dyes cannot sufficiently realize excellent dyeing rate and high daylight fastness in view of their properties, and furthermore, the affinity of polyester to blended fibers and the like is not clear.
이에, 수세 견뢰도 뿐만 아니라 발색성 및 염착률을 향상시키기 위하여, 분산염료 조성물들을 혼합하는 시도가 있지만, 우수한 견뢰도 및 염착률을 발휘하면서, 소망하는 발색성 등을 가지는 다양한 색상의 염료는 개발되지 못하고 있다.Thus, in order to improve color fastness and dyeing rate as well as washing fastness, attempts have been made to mix the disperse dye compositions, but dyes of various colors having desired color developing properties, etc., while exhibiting excellent fastness and dyeing rate, have not been developed.
이에 따라, 본 발명자들은 심도있는 연구와 다양한 실험을 거듭한 끝에, 이후 설명하는 바와 같이, 특정한 화합물들의 조합을 포함하는 분산염료 조성물을 이용하여 폴리에스테르 등을 포함하는 혼방 섬유 재료를 염색하는 방법을 개발하기에 이르렀고, 이 경우, 우수한 염착률 및 견뢰도를 얻을 수 있음을 발견하고, 본 발명을 완성하기에 이르렀다.Accordingly, the inventors, after extensive research and various experiments, described a method of dyeing a blended fiber material including polyester using a disperse dye composition containing a combination of specific compounds as described below. It has been developed, and in this case, it has been found that excellent dyeing rate and fastness can be obtained, and the present invention has been completed.
본 발명이 해결하고자 하는 과제는, 분산 염료를 적절한 비율로 혼합하여, 우수한 견뢰도를 가지는 분산염료 조성물을 제공하고자 하는 것이다. The problem to be solved by the present invention is to provide a disperse dye composition having excellent fastness by mixing disperse dyes in an appropriate ratio.
또한, 본 발명이 해결하고자 하는 다른 과제는, 상기 분산 염료 조성물을 사용하여 폴리에스테르 등을 포함하는 혼방 섬유 재료를 염색하는 방법을 제공하는 것으로, 이 경우, 종래의 염료에 비해 우수한 견뢰도를 얻을 수 있다.In addition, another problem to be solved by the present invention is to provide a method for dyeing a blend fiber material containing a polyester or the like using the disperse dye composition, in this case, it is possible to obtain excellent fastness compared to the conventional dye have.
본 발명은 위의 과제를 달성하기 위해, 하기 화학식 1의 화합물 1 내지 99 중량부 및 하기 화학식 2의 화합물 1 내지 99 중량부를 포함하는 분산염료 조성물을 제공한다.The present invention provides a dispersion dye composition comprising 1 to 99 parts by weight of the compound of Formula 1 and 1 to 99 parts by weight of the compound of Formula 2 to achieve the above object.
[화학식 1] [Formula 1]
Figure PCTKR2019000643-appb-img-000001
Figure PCTKR2019000643-appb-img-000001
[화학식 2][Formula 2]
Figure PCTKR2019000643-appb-img-000002
Figure PCTKR2019000643-appb-img-000002
상기 화학식 2에서, R 1은 수소원자 또는 (C1~C18)알킬이고, R 2는 (C1~C18)알킬 또는 -(CH 2) n-CO 2R a이고, n은 1 내지 8의 정수이고, R a는 (C1~C18)알킬 또는 (C1~C8)알콕시(C1~C8)알킬이다.In Formula 2, R 1 is a hydrogen atom or (C1-C18) alkyl, R 2 is (C1-C18) alkyl or-(CH 2 ) n -CO 2 R a , n is an integer of 1 to 8 , R a is (C1-C18) alkyl or (C1-C8) alkoxy (C1-C8) alkyl.
상기 화학식 1 및 상기 화학식 2로 이루어진 군에서 선택되는 화합물들을 혼합할 경우, 기존의 염료 조성물보다 뛰어난 일광 견뢰도, 승화 견뢰도, 물 견뢰도 등을 가지는 분산염료 조성물을 제조할 수 있다.When the compounds selected from the group consisting of Formula 1 and Formula 2 are mixed, it is possible to prepare a dispersion dye composition having a light fastness, sublimation fastness, water fastness and the like than the conventional dye composition.
상기 화학식 1의 화합물로 제조된 적색 계열의 분산염료 조성물은 염색 농도가 떨어져 진한 색 발현이 어려운 문제점이 있었고, 화학식 2의 화합물로 제조된 적색 계열의 분산염료 조성물은 승화 견뢰도가 떨어졌다.The disperse dye composition of the red series prepared with the compound of Formula 1 had a problem that it is difficult to express a dark color due to the dyeing concentration, the disperse fastness of the red series disperse dye prepared with the compound of Formula 2 was poor.
이에, 본 발명에 따른 분산염료 조성물은 특정한 함량의 화학식 1 및 2의 화합물들의 배합을 통해 얻고자 하는 수준의 높은 염색 농도와 뛰어난 일광 견뢰도 및 승화 견뢰도, 물견뢰도 등급을 얻을 수 있다. Thus, the dispersion dye composition according to the present invention can obtain a high dyeing concentration and excellent daylight fastness and sublimation fastness, water fastness grade of the level to be obtained through the combination of the compounds of formula 1 and 2 in a specific content.
본 발명의 일 양태에서, 상기 화학식 2의 화합물에서 R 1은 (C1~C8)알킬이고, R 2는 (C1~C8)알킬이고, n은 1 내지 3의 정수이고, R a는 (C1~C8)알킬 또는 (C1~C4)알콕시(C1~C4)알킬이다.In one embodiment of the present invention, in the compound of Formula 2, R 1 is (C1-C8) alkyl, R 2 is (C1-C8) alkyl, n is an integer of 1 to 3, R a is (C1 ~ C8) alkyl or (C1-C4) alkoxy (C1-C4) alkyl.
본 발명의 일 양태에서, 분산염료 조성물은 상기 화학식 1의 화합물 20 내지 80 중량부 및 상기 화학식 2의 화합물 80 내지 20 중량부를 포함할 수 있다.In one embodiment of the present invention, the disperse dye composition may include 20 to 80 parts by weight of the compound of Formula 1 and 80 to 20 parts by weight of the compound of Formula 2.
본 발명의 조성물에는 발명의 목적 및 효과를 저해하지 않는 범위 내에서 가용화제, 완충제, 빙결방지제 등의 기타 성분을 첨가할 수 있다. 이러한 기타 첨가제는 조성물 전체 중량을 기준으로 대략 1 내지 20 중량%의 범위에서 첨가될 수 있다.Other components, such as a solubilizer, a buffer, an antifreezing agent, can be added to the composition of this invention within the range which does not impair the objective and effect of this invention. Such other additives may be added in the range of approximately 1 to 20 weight percent based on the total weight of the composition.
상기 가용화제는 염료의 뭉침을 방지하고 용해를 도와 주는 첨가제 성분으로서, 대표적인 예로는 우레아, 티오우레아, 카프로락탐 등을 들 수 있다. 상기 완충제는 저장 보관시 염료의 분해를 막아주기 위하여 pH를 완충하는 역할을 하는 성분으로서, 대표적인 예로는 인산나트륨, 인산칼륨, 초산나트륨 등을 들 수 있다. 상기 빙결방지제는 액상 냉동보관시 어는 점을 낮춰주어 액상 염료가 얼지 않게 하는 역할을 하는 성분으로서, 대표적인 예로는 에틸렌글리콜, 폴리에틸렌글리콜, 다가알콜 화합물 등을 들 수 있다.The solubilizer is an additive component that prevents agglomeration of dyes and helps dissolution, and typical examples thereof include urea, thiourea, and caprolactam. The buffer is a component that buffers the pH to prevent degradation of the dye during storage and storage, and representative examples thereof include sodium phosphate, potassium phosphate, sodium acetate and the like. The freezing inhibitor lowers the freezing point during liquid freezing and serves as a component that does not freeze the liquid dye. Representative examples include ethylene glycol, polyethylene glycol, and polyalcohol compounds.
또한, 본 발명은 상기 분산염료 조성물을 사용하여 섬유재료를 염색하는 방법을 제공한다.The present invention also provides a method for dyeing a fiber material using the dispersion dye composition.
상기 섬유재료의 예로는 반합성 섬유, 합성 섬유, 재생 섬유, 또는 합성 섬유와 천연 섬유의 혼방 섬유가 있으며, 이러한 반합성 섬유로는, 예를 들어, 아세테이트, 합성 섬유로는 폴리에스테르, 폴리아미드, 폴리비닐, 폴리우레탄계 섬유, 재생 섬유로는 셀룰로우즈 등이 있다.Examples of the fibrous material include semisynthetic fibers, synthetic fibers, regenerated fibers, or blended fibers of synthetic fibers and natural fibers. Examples of such semisynthetic fibers include, for example, acetate, synthetic fibers such as polyester, polyamide, poly Vinyl, polyurethane-based fibers, recycled fibers include cellulose and the like.
상기 분산염료 조성물은 또한, 폴리에스테르 섬유의 혼방 섬유, 예를 들어, 폴리에스테르와 셀룰로우즈 섬유를 포함하는 혼방 섬유 등의 염색에 적용되어 높은 염착률 및 우수한 견뢰도를 나타낸다.The disperse dye composition is also applied to the dyeing of blended fibers of polyester fibers, for example blended fibers comprising polyester and cellulose fibers, and exhibits high dyeing rates and good fastnesses.
본 발명의 일 양태에서, 상기 분산염료 조성물을 이용하여, 반합성 섬유, 합성 섬유, 재생 섬유, 또는 합성 섬유와 천연 섬유의 혼방 섬유를 염색하는 방법이 제공된다.In one aspect of the present invention, a method for dyeing a semi-synthetic fiber, synthetic fibers, regenerated fibers, or blended fibers of synthetic fibers and natural fibers using the dispersion dye composition is provided.
본 발명의 일 양태에서, 상기 분산염료 조성물을 이용하여, 폴리에스테르계 섬유 또는 폴리 에스테르계 복합섬유를 염색하는 방법이 제공된다.In one aspect of the present invention, using the dispersion dye composition, there is provided a method for dyeing polyester fiber or polyester composite fiber.
본 발명의 일 양태에서, 상기 혼방 섬유는 폴리에스테르 섬유와 셀룰로오스 섬유를 포함할 수 있다.In one aspect of the present invention, the blend fiber may include polyester fibers and cellulose fibers.
본 발명에 따른 분산염료 조성물은 예를 들어, 콜드패드배치법, 연속 염색법, 침염법, 날염법, 발염법 등 여러 방법에 사용될 수 있으며, 바람직하게는 연속 염색법, 침염법에 사용될 수 있다.The disperse dye composition according to the present invention can be used in various methods, for example, cold pad placement method, continuous dyeing method, dyeing method, printing method, printing method, and preferably used in continuous dyeing method and dyeing method.
특히, 상기 연속 염색법으로는, 산결합제(예를 들어, 탄산나트륨, 중탄산나트륨 등)를 패딩액에 혼합하고, 공지의 방법으로 패딩하여 건열 또는 증열에 의해 염색하는 일욕 패딩법, 및 염료 패딩 후 무기중성염(예를 들어, 무수황산나트륨, 식염 등)과 산결합제(예를 들어, 가성소다, 규산소다 등)를 패딩액에 혼합하여 패딩하고, 공지의 방법으로 건열 또는 증열에 의해 염색하는 이욕 패딩법이 사용될 수 있다.In particular, as the continuous dyeing method, an acid-binding agent (for example, sodium carbonate, sodium bicarbonate, etc.) is mixed with a padding liquid, padded by a known method and dyed by dry heat or steaming, and after the dye padding inorganic Neutral salts (e.g., anhydrous sodium sulfate, salt, etc.) and acid binders (e.g., caustic soda, sodium silicate, etc.) are mixed and padded in the padding solution, and the bathing padding is dyed by dry heat or steaming by a known method. Law can be used.
본 발명에 따라 수득된 염색물 및 날염물은 축적성(build-up) 및 균염성(levelness)이 뛰어나다. 또한, 착색도가 뛰어나고, 섬유-염료 결합 안정성이 높으며, 일광 견뢰도 뿐만 아니라 타 섬유로의 오염 방지성도 뛰어나다.The dyeings and printings obtained according to the present invention are excellent in build-up and leveling. In addition, it is excellent in coloration, high fiber-dye bonding stability, and excellent in light fastness as well as prevention of contamination to other fibers.
본 발명에 따른 분산염료 조성물은 특정한 화합물들의 조합을 포함하므로, 폴리에스테르 등을 포함하는 혼방 섬유 재료를 염색 시 우수한 염착률을 나타내며, 일광, 물, 승화 등 제반 견뢰도가 우수하다.Since the disperse dye composition according to the present invention includes a combination of specific compounds, it exhibits excellent dyeing rate when dyeing blended fiber materials including polyester and the like, and has excellent fastness such as sunlight, water, and sublimation.
이하, 본 발명이 속하는 기술 분야에서 통상의 지식을 가진 자가 용이하게 실시할 수 있도록 본 발명의 실시예에 대하여 상세히 설명한다. 그러나, 본 발명은 여러 가지 다양한 형태로 구현될 수 있으며 여기에서 설명하는 실시예에 한정되지 않는다. Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily practice the present invention. As those skilled in the art would realize, the described embodiments may be modified in various different ways, all without departing from the spirit or scope of the present invention.
[제조예 1] 화학식 1의 화합물을 포함하는 분산염료 조성물의 제조 Preparation Example 1 Preparation of Disperse Dye Composition Containing Compound of Formula 1
하기 화학식 1의 화합물에 물과 분산제를 사용하여 입자크기가 1㎛ 이하가 90% 이상이 되도록 밀링한 후 pH를 조정한다. 이후, 스프레이 드라이 건조하여 하기 화학식 1의 화합물을 포함하는 분산염료 조성물을 얻었다.Using a compound of water and a dispersant to the compound of the formula (1), the pH is adjusted after milling to a particle size of 1㎛ or less 90% or more. Thereafter, spray dry drying to obtain a dispersion dye composition comprising a compound of formula (1).
[화학식 1][Formula 1]
Figure PCTKR2019000643-appb-img-000003
Figure PCTKR2019000643-appb-img-000003
[제조예 2] 화학식 3의 화합물을 포함하는 분산염료 조성물의 제조 Preparation Example 2 Preparation of Disperse Dye Composition Containing Compound of Formula 3
하기 화학식 3의 화합물을 상기 제조예 1과 동일한 방법을 사용하여 하기 화학식 3의 화합물을 포함하는 분산염료 조성물을 얻었다.Using the same method as in Preparation Example 1 to the compound of formula 3 to obtain a disperse dye composition comprising a compound of formula (3).
[화학식 3][Formula 3]
Figure PCTKR2019000643-appb-img-000004
Figure PCTKR2019000643-appb-img-000004
[제조예 3] 화학식 4의 화합물을 포함하는 분산염료 조성물의 제조 Preparation Example 3 Preparation of Disperse Dye Composition Containing Compound of Formula 4
하기 화학식 4의 화합물을 상기 제조예 1과 동일한 방법을 사용하여 하기 화학식 4의 화합물을 포함하는 분산염료 조성물을 얻었다.Using the same method as Preparation Example 1 to the compound of formula 4 to obtain a disperse dye composition comprising a compound of formula (4).
[화학식 4][Formula 4]
Figure PCTKR2019000643-appb-img-000005
Figure PCTKR2019000643-appb-img-000005
[제조예 4] 화학식 5의 화합물을 포함하는 분산염료 조성물의 제조 Preparation Example 4 Preparation of Disperse Dye Composition Containing Compound of Formula 5
하기 화학식 5의 화합물을 상기 제조예 1과 동일한 방법을 사용하여 하기 화학식 5의 화합물을 포함하는 분산염료 조성물을 얻었다.Using the same method as Preparation Example 1 to the compound of formula 5 to obtain a disperse dye composition comprising a compound of formula (5).
[화학식 5][Formula 5]
Figure PCTKR2019000643-appb-img-000006
Figure PCTKR2019000643-appb-img-000006
[비교예 1]Comparative Example 1
제조예 2의 조성물을 포함하는 분산염료 조성물을 하기 표 1과 같이 제조하였다.Disperse dye composition comprising the composition of Preparation Example 2 was prepared as shown in Table 1.
[실시예 1 내지 3] [Examples 1-3]
제조예 1의 조성물, 및 제조예 2 내지 4의 조성물에서 선택되는 조성물을 포함하는 분산염료 조성물들을 하기 표 1과 같이 제조하였다.Disperse dye compositions comprising the composition of Preparation Example 1, and the composition selected from the compositions of Preparation Examples 2 to 4 were prepared as shown in Table 1.
Figure PCTKR2019000643-appb-img-000007
Figure PCTKR2019000643-appb-img-000007
[분산염료 조성물의 염색 및 견뢰도 평가][Dyeing and Fastness Evaluation of Dispersant Composition]
폴리에스테르 100 g, 실온에서 80% 초산에 의해 pH 4.0 ~ pH 5.0로 조절시킨 실시예 1 내지 3 및 비교예 1 내지 4의 분산염료 조성물 1 g, 균염화제 0.5 g/l를 포함하는 액중에 1:10의 액비로 침지시킨다. 3℃/분의 속도로 60℃로 가열한 후 1~2℃/분의 속도로 130℃까지 가열하여 60 분 동안 염색을 수행한다. 이어서, 염액을 80℃로 냉각시키고, 염색된 폴리에스테르 직물을 수세한 다음, 36% 수산화나트륨 용액 4 ml/l, 황산수소나트륨 용액 4 g/l 를 포함하는 욕중에서 20 분 동안 70~80℃의 온도 하에 환원 세정 한다. 이어서 가공된 염색물을 수세하고 건조시킨다.In a liquid containing 100 g of polyester, 1 g of the disperse dye composition of Examples 1 to 3 and Comparative Examples 1 to 4 and 0.5 g / l of a leveling agent, adjusted to pH 4.0 to pH 5.0 by 80% acetic acid at room temperature. Immerse in 1:10 liquid ratio. The dyeing is performed at 60 ° C. at a rate of 3 ° C./min and then to 130 ° C. at a rate of 1 to 2 ° C./min for 60 minutes. The salt solution is then cooled to 80 ° C., washed with dyed polyester fabric and then 70-80 ° C. for 20 minutes in a bath containing 4 ml / l of 36% sodium hydroxide solution and 4 g / l sodium hydrogen sulfate solution. Cleans under reduced temperature. The processed dyeings are then washed with water and dried.
일광 견뢰도는 AATCC 16E 방법으로 진행하였고 물 견뢰도는 ISO-105-E01로 진행하였으며, 승화 견뢰도 ISO-105-P01로 진행하였다. Daylight fastness was carried out by AATCC 16E method, water fastness was progressed by ISO-105-E01, and sublimation fastness by ISO-105-P01.
같은 농도에서의 염착률과 견뢰도 평가 결과는 하기 표 2에 나타내었다.The results of the evaluation of dyeing rate and fastness at the same concentration are shown in Table 2 below.
Figure PCTKR2019000643-appb-img-000008
Figure PCTKR2019000643-appb-img-000008
상기 표 2에서 보는 바와 같이, 제조예 1 내지 4의 화합물들을 혼합한 실시예 1 내지 3의 분산염료 조성물을 이용하여 폴리에스테르를 염색하는 경우, 비교예 1의 분산염료 조성물을 이용한 경우보다 우수한 염착률을 나타낸다. As shown in Table 2, when dyeing the polyester using the disperse dye composition of Examples 1 to 3 mixed with the compounds of Preparation Examples 1 to 4, the salt than the case of using the disperse dye composition of Comparative Example 1 Indicative coverage.
또한, 실시예 1 내지 3의 조성물을 이용하여 폴리에스테르를 염색하는 경우, 비교예 1의 분산염료 조성물을 이용한 경우보다, 뛰어난 일광, 승화, 물견뢰도를 갖는 것을 확인할 수 있다. Moreover, when dyeing polyester using the composition of Examples 1-3, it can be confirmed that it has the outstanding daylight, sublimation, and water fastness compared with the case of using the dispersion dye composition of the comparative example 1.
이상으로 본 발명 내용의 특정한 부분을 상세히 기술하였는 바, 당업계의 통상의 지식을 가진 자에게 있어서, 이러한 구체적 기술은 단지 바람직한 실시 양태일 뿐이며, 이에 의해 본 발명의 범위가 제한되는 것이 아닌 점은 명백할 것이다. 따라서, 본 발명의 실질적인 범위는 첨부된 청구항들과 그것들의 등가물에 의하여 정의된다고 할 것이다. As described above in detail specific parts of the present invention, it is apparent to those skilled in the art that such specific descriptions are merely preferred embodiments, and thus the scope of the present invention is not limited thereto. something to do. Thus, the substantial scope of the present invention will be defined by the appended claims and their equivalents.

Claims (5)

  1. 하기 화학식 1의 화합물 1 내지 99 중량부 및 하기 화학식 2의 화합물 1 내지 99 중량부를 포함하는 분산염료 조성물:1 to 99 parts by weight of a compound of Formula 1 and 1 to 99 parts by weight of a compound of Formula 2
    [화학식 1][Formula 1]
    Figure PCTKR2019000643-appb-img-000009
    Figure PCTKR2019000643-appb-img-000009
    [화학식 2][Formula 2]
    Figure PCTKR2019000643-appb-img-000010
    Figure PCTKR2019000643-appb-img-000010
    상기 화학식 2에서,In Chemical Formula 2,
    R 1은 수소원자 또는 (C1~C18)알킬이고,R 1 is a hydrogen atom or (C 1 -C 18) alkyl,
    R 2는 (C1~C18)알킬 또는 -(CH 2) n-CO 2R a이고, R 2 is (C 1 -C 18) alkyl or-(CH 2 ) n -CO 2 R a ,
    n은 1 내지 8의 정수이고, n is an integer from 1 to 8,
    R a는 (C1~C18)알킬 또는 (C1~C8)알콕시(C1~C8)알킬이다.R a is (C 1 -C 18) alkyl or (C 1 -C 8) alkoxy (C 1 -C 8) alkyl.
  2. 제1항에 있어서, 상기 화학식 2의 화합물에서 R 1은 (C1~C8)알킬이고, R 2는 (C1~C8)알킬이고, n은 1 내지 3의 정수이고, R a는 (C1~C8)알킬 또는 (C1~C4)알콕시(C1~C4)알킬인 것인, 분산염료 조성물.The compound of claim 1, wherein in the compound of Formula 2, R 1 is (C1-C8) alkyl, R 2 is (C1-C8) alkyl, n is an integer of 1 to 3, R a is (C1-C8) It is an alkyl or (C1-C4) alkoxy (C1-C4) alkyl, Disperse dye composition.
  3. 제1항에 있어서, 상기 화학식 1의 화합물 20 내지 80 중량부 및 상기 화학식 2의 화합물 80 내지 20 중량부를 포함하는 분산염료 조성물.According to claim 1, Dispersed dye composition comprising 20 to 80 parts by weight of the compound of Formula 1 and 80 to 20 parts by weight of the compound of Formula 2.
  4. 제1항에 따른 분산염료 조성물을 이용하여, 반합성 섬유, 합성 섬유, 재생 섬유, 또는 합성 섬유와 천연 섬유의 혼방 섬유를 염색하는 방법.A method of dyeing semisynthetic fibers, synthetic fibers, regenerated fibers, or blended fibers of synthetic fibers and natural fibers using the dispersion dye composition according to claim 1.
  5. 제4항에 있어서, 상기 혼방 섬유는 폴리에스테르 섬유와 셀룰로오스 섬유를 포함하는 것인 방법.The method of claim 4 wherein the blended fiber comprises polyester fiber and cellulose fiber.
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