KR102002836B1 - Disperse dye composition for ssupercritical carbon dioxide dyeing - Google Patents
Disperse dye composition for ssupercritical carbon dioxide dyeing Download PDFInfo
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General 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
- D06P1/16—General 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
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- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
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Abstract
Description
본 발명은 초임계 이산화탄소 염색기에서 소수성 섬유재료를 염색하기 위한 염료 조성물에 관한 것이며, 더욱 상세하게는 PET 등의 폴리에스테르 섬유를 초임계 이산화탄소 염색 기술을 사용하여 염색하기 위한 분산염료 조성물에 관한 것이다. The present invention relates to a dye composition for dyeing a hydrophobic fiber material in a supercritical carbon dioxide dyeing machine, and more particularly to a disperse dye composition for dyeing polyester fibers such as PET using a supercritical carbon dioxide dyeing technique.
초임계 유체를 이용한 초임계 염색은 독일의 Schollmeyer 교수가 1991년 초임계 CO2를 이용한 섬유 염색에 대한 논문을 발표함으로서 본격적인 연구가 시작되었다. Supercritical dyeing using supercritical fluid was started in earnest by Professor Schollmeyer of Germany, who published a paper on fiber staining using supercritical CO 2 in 1991.
초임계 유체 염색공정을 통한 섬유 제품화된 사례는 아디다스와 제휴한 태국 Yeh Group의 "Dry Dye"와 나이키와 제휴한 대만 Far Estern Group의 "Color Dry"로 양분되고 있으나, 염색공정이나 사용염료와 같은 기술적인 내용은 기업 대외비로 일체 공개를 하지않고 있기 때문에 기술의 실체에 대한 접근이 상당히 어려운 상황이다. The case of fiber production through supercritical fluid dyeing process is divided into "Dry Dye" of Thailand Yeh Group which is affiliated with adidas and "Color Dry" of Far Estern Group of Taiwan which is affiliated with Nike, Because the technical content is not disclosed to the public by the confidentiality of the enterprise, it is very difficult to access the reality of the technology.
현재 DyeCoo사는 인도의 염료회사인 Colourtex사와 제휴를 통해 17종의 염료를 독점 개발하여 상기 염색공장에서 현장 적용시험을 거쳐 최종 15종의염료를 선정한 것으로 알려져 있다. Currently, DyeCoo has developed 17 kinds of dyestuff exclusively through a partnership with Colourtex, an Indian dye company, and it is known that 15 kinds of dyestuffs have been selected from the above-mentioned dyeing factory after being subjected to on-site application tests.
한국에서 초임계 유체를 이용한 섬유분야 연구는 실험실용 초임계유체 장치를 이용하여 1995년 영남대 배효광, 심재진 교수팀이 염료의 용해도를 측정한 이래, 장성호 등은 C.I Disperse Red 60, Blue 60, Orange 30의 PET, Nylon에 대한 염착평형과 이론해석을 실시하였고, 성환도 등은 여러 분산염료의 조용매 첨가 전후의 용해도 증진에 대한 연구를 실시하였다. 또한, PET외에도 Polypropylene, Aramid, PLA 등 여러 종류의 섬유에 대한 염색성과 물성저하 여부를 검토하는 연구도 이루어지고 있으나, 대상염료의 구조 및 컬러가 제한적이고 실제 상업화가 가능한 수준의 물성 달성에는 매우 미흡한 결과를 나타내고 있다. In Korea, supercritical fluid was used for the study of supercritical fluids in Korea. In 1995, Yeungnam University and Yeongnam University team measured the solubility of dyestuffs. Jang Seongho and others used CI Disperse Red 60, Blue 60,
한편, 초임계 CO2염색은 2009/2010 Herman Wijffels Innovation Award의 혁신적 친환경적 제품 부문 최고상을 수상하였으며, 물절약 100%, CO2저감 60%, 비용절감 30~50%의 효과로 2012 파퓰러 사이언스 혁신 대상에 선정되었다. Supercritical CO 2 staining was awarded the 2009/2010 Herman Wijffels Innovation Award for Best Innovative Eco-Product Product Award, and it was awarded the 2012 Popular Science Innovation Award with 100% water saving, 60% CO 2 reduction and 30% Respectively.
본 발명은 초임계 이산화탄소 염색기를 사용하여 물을 사용하지 않고 폴리에스테르 섬유를 친환경적으로 염색하는데 적합한 흑색 분산 염료 조성물을 제공하는 것이다. The present invention is to provide a black disperse dye composition suitable for environmentally dyeing polyester fibers without using water using a supercritical carbon dioxide dyeing machine.
상기 과제를 해결하기 위한 본 발명의 분산 염료 조성물은 다음 구조식 (1) 내지 (3)의 화합물을 포함한다:The dispersion dye composition of the present invention for solving the above-mentioned problems includes a compound of the following structural formulas (1) to (3):
본 발명의 염료 조성물은 색 재현성 및 견뢰도가 우수하고 초임계 이산화탄소 염색기를 사용하여 물을 사용하지 않고 폴리에스테르 섬유를 친환경적으로 염색할 수 있다. The dye composition of the present invention is excellent in color reproducibility and fastness, and is capable of dyeing polyester fibers environmentally without using water by using a supercritical carbon dioxide dyeing machine.
도 1은 본 발명의 염료의 합성 결과로 도 1a는 황색 염료, 도 1b는 적색 염료, 도 1c는 청색 염료의 합성 결과이다.
도 2는 본 발명의 실시 예의 조성물의 염료의 색 재현성 결과를 나타내는 사진이다. Fig. 1 shows the results of synthesis of the dyes of the present invention as a result of synthesis of a yellow dye, a red dye and a blue dye in Fig. 1a, Fig. 1b and Fig. 1c.
2 is a photograph showing a color reproducibility result of a dye of a composition of an embodiment of the present invention.
본 발명의 발명자들은 초임계 유체를 이용하여 폴리에스테르, 예를 들어 PET 섬유의 염색에 적합한 흑색 분산 염료를 선별하기 위해 다양한 분산염료를 혼합하여 시험하였으며, 그 가운데 다음의 세 염료를 선별하고 합성하였다. The inventors of the present invention have tested various disperse dyes in order to select black disperse dyes suitable for dyeing polyester, for example, PET fibers, using supercritical fluid, and selected three dyes among the following dyes .
일반적인 합성 방법은 다음과 같다: The general synthesis method is as follows:
1) H2SO4(90g)에 용해된 디아조 화합물(0.1mol)에 42% 니트로실황산(NSA)을 적가하여 디아조늄염을 생성한다(0-5℃).1) 42% nitrousulfuric acid (NSA) is added dropwise to the diazo compound (0.1 mol) dissolved in H 2 SO 4 (90 g) to form the diazonium salt (0-5 ° C.).
2) 커플러(0.11mol)를 MeOH(용매)에 용해시킨다. 2) Coupler (0.11 mol) is dissolved in MeOH (solvent).
3) 1)에서 생성된 디아조늄염 용액을 2)의 용액에 천천히 적가하여 커플링 반응을 진행시킨다(아조 커플링)(0-5℃)3) The diazonium salt solution produced in 1) is slowly added dropwise to the solution of 2) to proceed the coupling reaction (azo coupling) (0-5 ° C)
4) 3)에서 생성된 아조 염료를 세척 후 건조시킨다(수율 90-98%, 순도 91-96%). 4) The azo dye produced in 3) is washed and dried (yield: 90-98%, purity: 91-96%).
흑색 염료 조성물을 구성하는 각 황색, 적색, 청색 염료는 최대한 높은 순도의 염료를 사용하여야 하고, 순도가 낮을 경우 정제하여 사용하여야 한다. 순도가 낮으면, 염색 과정에서 염반이 발생한다. 또, 각 황색, 적색, 청색 염료는 적정 비율로 조합되어야 재현성의 확보가 가능하고 색상차를 줄일 수 있다. 본 발명자들의시험결과 가장 바람직한 배합비는 황색(20%), 적색(28%), 청색(52%)였다. For each yellow, red and blue dye constituting the black dye composition, a dye having a purity as high as possible should be used, and when the purity is low, it should be purified and used. If the purity is low, a dyestuff produces a dyestuff. In addition, each yellow, red, and blue dye should be combined at an appropriate ratio to ensure reproducibility and reduce the color difference. As a result of the tests conducted by the present inventors, the most preferable mixing ratio was yellow (20%), red (28%) and blue (52%).
또, 캐리어를 사용하여 피염물의 이동에 의한 불균염 문제를 해결하고 균염성을 확보한다. In addition, by using a carrier, the problem of unevenness due to the movement of the salt is solved and the uniformity is ensured.
또한, 초임계 유체 염색기에 사용하는 오일은 폴리에텔렌글리콜 오일, 예를 들어 PEG 400을 사용하는 것이 바람직하다. 파라핀계 오일을 사용하는 경우 냄새와 연기가 발생하고 세척에 문제가 생긴다. In addition, it is preferable to use a polyether glycol oil, for example, PEG 400, as the oil used in the supercritical fluid dyeing machine. When paraffin oil is used, odor and smoke are generated and there is a problem in washing.
염색기의 포트 밀봉재는 나선형 타입의 밀봉재를 사용하는 것이 누출이 없고 밀봉에 유리하다. 염색기의 운전 조건은 125℃에서 40~60분, 압력은 250바아 내외로 하는 것이 바람직하다. The sponge type sealing material of the dyeing machine is free from leakage and is advantageous for sealing. The operating condition of the dyeing machine is preferably set at 125 ° C for 40 to 60 minutes and the pressure is set to about 250 bar.
이하 실시 예를 통해 본 발명을 더욱 상세하게 설명한다: The present invention is further illustrated by the following examples:
제조 예 1 황색 염료의 합성Production Example 1 Synthesis of yellow dye
H2SO4(90g)에 용해된 디아조 화합물(0.1mol)을 4℃로 유지하면서 42% 니트로실황산(NSA)을 적가하여 디아조늄염을 생성하였다. 상기 구조의 커플러(0.11mol)를 MeOH(용매)에 용해시켰다. 4℃로 유지하면서 디아조늄염 용액을 천천히 적가하여 커플링 반응을 진행시켰다. 세척 후 건조시켜 순도 96.8%의 염료를 얻었다(수율 93%). 분광학적(proton NMR, LC/MS 등) 데이터 결과는 도 1a에 나타내었다. 42% nitrosylsulfuric acid (NSA) was added dropwise to the diazonium salt while keeping the diazo compound (0.1 mol) dissolved in H 2 SO 4 (90 g) at 4 ° C. The coupler (0.11 mol) of the above structure was dissolved in MeOH (solvent). The diazonium salt solution was slowly added dropwise while maintaining the temperature at 4 ° C to conduct the coupling reaction. After washing and drying, a dye having a purity of 96.8% was obtained (yield: 93%). Spectroscopic (proton NMR, LC / MS, etc.) data results are shown in FIG.
제조 예 2 적색 염료의 합성Production Example 2 Synthesis of red dye
H2SO4(90g)에 용해된 디아조 화합물(0.1mol)을 4℃로 유지하면서 42% 니트로실황산(NSA)을 적가하여 디아조늄염을 생성하였다. 상기 구조의 커플러(0.11mol)를 MeOH(용매)에 용해시켰다. 4℃로 유지하면서 디아조늄염 용액을 천천히 적가하여 커플링 반응을 진행시켰다. 세척 후 건조시켜 순도 92.5%의 염료를 얻었다(수율 98%). 분광학적(proton NMR, LC/MS 등) 데이터 결과는 도 1b에 나타내었다. 42% nitrosylsulfuric acid (NSA) was added dropwise to the diazonium salt while keeping the diazo compound (0.1 mol) dissolved in H 2 SO 4 (90 g) at 4 ° C. The coupler (0.11 mol) of the above structure was dissolved in MeOH (solvent). The diazonium salt solution was slowly added dropwise while maintaining the temperature at 4 ° C to conduct the coupling reaction. Washed and dried to obtain a dye having a purity of 92.5% (yield: 98%). Spectroscopic (proton NMR, LC / MS, etc.) data results are shown in FIG.
제조 예 3 청색 염료의 합성Production Example 3 Synthesis of blue dye
H2SO4(90g)에 용해된 디아조 화합물(0.1mol)을 4℃로 유지하면서 42% 니트로실황산(NSA)을 적가하여 디아조늄염을 생성하였다. 상기 구조의 커플러(0.11mol)를 MeOH(용매)에 용해시켰다. 4℃로 유지하면서 디아조늄염 용액을 천천히 적가하여 커플링 반응을 진행시켰다. 세척 후 건조시켜 순도 92%의 염료를 얻었다(수율 97%). 분광학적(proton NMR, LC/MS 등) 데이터 결과는 도 1c에 나타내었다. 42% nitrosylsulfuric acid (NSA) was added dropwise to the diazonium salt while keeping the diazo compound (0.1 mol) dissolved in H 2 SO 4 (90 g) at 4 ° C. The coupler (0.11 mol) of the above structure was dissolved in MeOH (solvent). The diazonium salt solution was slowly added dropwise while maintaining the temperature at 4 ° C to conduct the coupling reaction. Washed and dried to obtain a dye having a purity of 92% (yield: 97%). Spectroscopic (proton NMR, LC / MS, etc.) data results are shown in Figure 1c.
실시 예 1 Example 1
제조 예 1,2,3에서 각각 제조된 황색, 적색, 청색 염료를 중량비로 24%, 24%, 52%로 배합하고 압력계가 달린 200mL 초임계 유체 염색장비에서 Oil-bath의 내부 오일 온도를 120℃로 맞추어 준 후 염색기 내부에 PET 섬유 10g, 배합한 염료 50mg을 준비하고, 염색기에 부착된 밸브를 통해 주입 이산화탄소 가스를 80g을 주입하여, 압력 250bar에서 125℃로 승온하여 60분간 염색을 진행하였다. 4개의 port를 탈리 후, CO2 가스를 제거, 염색이 된 PET 섬유를 꺼냈다. 과정을 반복하여 색상을 비교한 결과 미세한 색상 차이가 발견되었다. The yellow, red, and blue dyes prepared in Preparation Examples 1, 2 and 3 were blended in 24%, 24%, and 52% by weight, respectively. In a 200-mL supercritical fluid dyeing apparatus equipped with a pressure gauge, 10 g of PET fibers and 50 mg of dyes were added to the inside of the dyeing machine. 80 g of carbon dioxide gas was injected through a valve attached to the dyeing machine, and the temperature was raised to 125 ° C at a pressure of 250 bar, followed by dyeing for 60 minutes . After removing the four ports, the CO 2 gas was removed and the dyed PET fibers were taken out. As a result of repeating the process and comparing the colors, a slight color difference was found.
실시 예 2 Example 2
제조 예 1,2,3에서 각각 제조된 황색, 적색, 청색 염료를 중량비로 20%, 28%, 52%로 배합하고 압력계가 달린 200mL 초임계 유체 염색장비에서 Oil-bath의 내부 오일 온도를 120℃로 맞추어 준 후 염색기 내부에 PET 섬유 10g, 배합한 염료 50mg을 준비하고, 염색기에 부착된 밸브를 통해 주입 이산화탄소 가스를 80g을 주입하여, 압력 250bar에서 125℃로 승온하여 60분간 염색을 진행하였다. 4개의 port를 탈리 후, CO2 가스를 제거, 염색이 된 PET 섬유를 꺼냈다. 과정을 반복하여 색상을 비교한 결과 색상 차이가 0.2 이하로 우수한 재현성을 나타내었다. 결과 사진은 도 2에 게시하였다. The yellow, red, and blue dyes prepared in Preparation Examples 1, 2 and 3 were blended in 20%, 28%, and 52% by weight, respectively. In a 200-mL supercritical fluid dyeing apparatus equipped with a pressure gauge, 10 g of PET fibers and 50 mg of dyes were added to the inside of the dyeing machine. 80 g of carbon dioxide gas was injected through a valve attached to the dyeing machine, and the temperature was raised to 125 ° C at a pressure of 250 bar, followed by dyeing for 60 minutes . After removing the four ports, the CO 2 gas was removed and the dyed PET fibers were taken out. As a result of repeating the process, the color difference was less than 0.2 and the reproducibility was excellent. The resulting picture is posted in FIG.
한국 섬유 소재연구원에 의뢰하여 측정한 색차 및 견뢰도 측정 결과를 아래 표 1에 나타내었다.The results of colorimetric and fastness measurements measured by Korea Institute of Textile Research are shown in Table 1 below.
염료 흡진율은 다음의 방법으로 측정하였다. The dye absorption rate was measured by the following method.
1) 초임계 유체 염색이 끝난 후, 포트에서 천을 꺼낸다.1) Supercritical fluid After dyeing, remove the fabric from the port.
2) 빈 비커의 무게를 잰다.2) Weigh empty beakers.
3) 천을 꺼낸 포트에 아세톤을 넣어준다.3) Put acetone in the port from which cloth was taken out.
4) 포트의 뚜껑에 잔류하는 염료도 아세톤으로 녹여 비커에 넣는다.4) Dye remaining in the lid of the pot is also dissolved in acetone and put in a beaker.
5) 포트의 잔여 염료를 아세톤으로 완전히 녹인 후 비커에 담는다.5) Dissolve the remaining dyestuff in the pot thoroughly with acetone and place in a beaker.
6) 비커에 담은 염료가 용해되어 있는 아세톤을 증발시킨다.6) The acetone in which the dye contained in the beaker is dissolved is evaporated.
7) 아세톤이 완전히 증발된 것을 확인한다.7) Confirm that the acetone has completely evaporated.
8) 비커의 무게를 재어준다. 빈 비커 무게와 차이로 염료 흡진율을 구한다.8) Weigh the beaker. The dye absorption rate is determined by the difference between the weight of the empty beaker.
차car
(0.5% o.w.f)(0.5% o.w.f)
(%)(%)
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