KR101942305B1 - Pyridine red disperse dye composition and preparing method thereof - Google Patents
Pyridine red disperse dye composition and preparing method thereof Download PDFInfo
- Publication number
- KR101942305B1 KR101942305B1 KR1020160157952A KR20160157952A KR101942305B1 KR 101942305 B1 KR101942305 B1 KR 101942305B1 KR 1020160157952 A KR1020160157952 A KR 1020160157952A KR 20160157952 A KR20160157952 A KR 20160157952A KR 101942305 B1 KR101942305 B1 KR 101942305B1
- Authority
- KR
- South Korea
- Prior art keywords
- red
- dye composition
- disperse dye
- disperse
- red disperse
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 13
- 239000000986 disperse dye Substances 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- MGCGMYPNXAFGFA-UHFFFAOYSA-N 2-amino-5-nitrobenzonitrile Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C#N MGCGMYPNXAFGFA-UHFFFAOYSA-N 0.000 claims description 5
- -1 2-hydroxy-ethylamino Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- TUXJTJITXCHUEL-UHFFFAOYSA-N disperse red 11 Chemical compound C1=CC=C2C(=O)C3=C(N)C(OC)=CC(N)=C3C(=O)C2=C1 TUXJTJITXCHUEL-UHFFFAOYSA-N 0.000 abstract description 7
- 239000000975 dye Substances 0.000 abstract description 7
- 239000001044 red dye Substances 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000002845 discoloration Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LSPMHHJCDSFAAY-UHFFFAOYSA-N 2,6-dichloro-4-methylpyridine-3-carbonitrile Chemical compound CC1=CC(Cl)=NC(Cl)=C1C#N LSPMHHJCDSFAAY-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JPIGSMKDJQPHJC-UHFFFAOYSA-N 1-(2-aminoethoxy)ethanol Chemical compound CC(O)OCCN JPIGSMKDJQPHJC-UHFFFAOYSA-N 0.000 description 1
- GTACSIONMHMRPD-UHFFFAOYSA-N 2-[4-[2-(benzenesulfonamido)ethylsulfanyl]-2,6-difluorophenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=C(F)C=C1SCCNS(=O)(=O)C1=CC=CC=C1 GTACSIONMHMRPD-UHFFFAOYSA-N 0.000 description 1
- CCDGXDPMVHOHJS-UHFFFAOYSA-N 2-anilino-6-chloro-4-methylpyridine-3-carbonitrile Chemical compound CC1=CC(Cl)=NC(NC=2C=CC=CC=2)=C1C#N CCDGXDPMVHOHJS-UHFFFAOYSA-N 0.000 description 1
- WQFCFMPMUNOOTQ-UHFFFAOYSA-N 3-(2-phenoxyethoxy)propan-1-amine Chemical compound NCCCOCCOC1=CC=CC=C1 WQFCFMPMUNOOTQ-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- PJLOHVAAPSXEQI-UHFFFAOYSA-N 4-(3-aminopropoxy)butan-1-ol Chemical compound NCCCOCCCCO PJLOHVAAPSXEQI-UHFFFAOYSA-N 0.000 description 1
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 1
- 101710130081 Aspergillopepsin-1 Proteins 0.000 description 1
- 102100031007 Cytosolic non-specific dipeptidase Human genes 0.000 description 1
- MZYDHZVBNWKUHC-UHFFFAOYSA-N OCCNC1=NC(=C(C#N)C(=C1)C)NCCCCCOC1=CC=CC=C1 Chemical compound OCCNC1=NC(=C(C#N)C(=C1)C)NCCCCCOC1=CC=CC=C1 MZYDHZVBNWKUHC-UHFFFAOYSA-N 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0048—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a six-membered heterocyclic ring with one nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pyridine Compounds (AREA)
Abstract
본 발명은 신규의 적색 분산 염료 조성물에 관한 것으로 하기 구조식 (I)의 화합물 및 구조식 (II)의 화합물을 포함한다:
본 발명의 적색 분산 염료 조성물은 Disperse Red 279보다 심색의 적색염료로 사용될 수 있으며 같은 고일광 견뢰도의 특색을 지니고 있다. 또한, 고농도의 특성을 보이기에 고일광 흑색 염료의 성분으로 사용할 수 있는 장점을 갖고 있다.The present invention relates to a novel red disperse dye composition comprising a compound of formula (I) and a compound of formula (II): < EMI ID =
The red disperse dye composition of the present invention can be used as a red dye of a more reddish color than Disperse Red 279 and has the same high light fastness characteristics. In addition, it has an advantage that it can be used as a component of high-brightness black dyes because of its high concentration characteristics.
Description
본 발명은 신규의 피리딘 골격을 갖는 적색 분산 염료 조성물 및 그 제조방법에 관한 것으로, 더욱 상세하게는 고일광 견뢰도를 갖는 신규의 적색 분산 염료 및 그 제조방법에 관한 것이다. The present invention relates to a red disperse dye composition having a novel pyridine skeleton and a process for preparing the same. More particularly, the present invention relates to a novel red disperse dye having high light fastness and a process for producing the same.
피리딘 유도체를 커플러(coupler)로 하는 고일광 적색염료로 자동차 내장재 등에 사용되는 중요한 분산염료인 디스퍼스 레드(Disperse Red) 279란 염료가 있다. 한국등록특허 10-1238117호 등에서 알 수 있는 바와 같이 고일광 염료로 자동차나 UV 노출이 있는 분야에 사용되고 있다. Disperse Red 279, an important disperse dye used in automotive interiors and the like, is a high-bright red dye having a pyridine derivative as a coupler. As can be seen from Korean Patent No. 10-1238117, it is used as a high-light dyestuff in automotive and UV exposure applications.
이 염료는, 하기 반응식과 같이, 2,6-디클로로-4-메틸 니코티노니트릴(DCP)로부터 3-(2-페녹시에톡시)프로판-1-아민(PEPA)과 2-아미노에탄올(MEA), 4-(3-아미노프로폭시)부탄-1-올(HBPA), 아민을 치환시켜 합성된 4가지의 이성질체에 2-시아노-4-니트로 아닐린을 디아조화제(diazotizer)로 사용하여 합성한 염료이고 이는 고일광 견뢰도를 갖는 특성으로 고일광을 요구하는 환경에 적합하게 사용될 수 있다. This dye is obtained from 2,6-dichloro-4-methylnicotinonitrile (DCP) by reacting 3- (2-phenoxyethoxy) propane-1-amine (PEPA) and 2-aminoethanol ), 4- (3-aminopropoxy) butan-1-ol (HBPA), and 4 isomers synthesized by substituting amines with 2-cyano-4-nitroaniline as a diazotizer It is a synthetic dyestuff. It has high color fastness and can be used for environment requiring high light.
본 발명은 Disperse Red 279와 유사한 커플로 Disperse Red 279보다 심색을 갖는 신규의 적색 분산 염료를 제공하고자 하는 것이다. The present invention is to provide a novel red disperse dye having a more pale color than Disperse Red 279 with a couple similar to Disperse Red 279.
본 발명의 신규의 적색 분산 염료는 하기 구조식 (I)의 화합물 및 구조식 (II)의 화합물을 포함한다. The novel red disperse dyes of the present invention comprise a compound of formula (I) and a compound of formula (II).
이는 Disperse Red 279보다 심색의 적색염료로 사용될 수 있으며 같은 고일광 견뢰도의 특색을 지니고 있다.It can be used as a red dye of deep red color than Disperse Red 279 and has the same high light fastness.
또한, 고농도의 특성을 보이기에 고일광 흑색 염료의 성분으로 사용할 수 있는 장점을 갖고 있다.In addition, it has an advantage that it can be used as a component of high-brightness black dyes because of its high concentration characteristics.
도 1은 본 발명의 염료의 제조 단계별 HPLC 데이터를 나타낸 도면.
도 2는 Disperse Red 279와 본 발명의 신규 적색염료의 흡수곡선을 비교한 그래프. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a diagram showing HPLC data for the preparation step of a dye of the present invention. FIG.
2 is a graph comparing absorption curves of Disperse Red 279 with the novel red dye of the present invention.
본 발명의 적색 분산 염료는 디아조화제로 2-아미노-5-니트로 벤조니트릴을, 커플러로 6-(2-히드록시-에틸아미노)-4-메틸-2-(5-페녹시-펜틸아미노)-니코티노니트릴과 2-(2-(2-히드록시에톡시)에틸)아미노)-4-메틸-6-(펜틸아미노)니코티노니트릴로부터 합성된다. The red disperse dye of the present invention can be obtained by reacting 2-amino-5-nitrobenzonitrile as a diazotizing agent and 6- (2-hydroxy-ethylamino) -4- -Nicotinonitrile with 2- (2- (2-hydroxyethoxy) ethyl) amino) -4-methyl-6- (pentylamino) nicotinonitrile.
이러한 구조의 커플러를 얻고자 다음과 같이 역합성을 진행하여 얻어진 출발물질을 사용하여 각각 합성하였다.In order to obtain a coupler having such a structure, a reverse synthesis was carried out as follows to synthesize each of them using the obtained starting materials.
상기 역합성(Retro-analysis)을 통하여 출발물질은 2-아미노-5-니트로벤조니트릴을 디아조화제로 사용하고, 커플러로는, 6-디클로-4-메틸니코티노니트릴로부터 출발하여 아닐린과 2-(2-아미노에톡시)에탄-1-올을 차례대로 치환시켜 합성하였다. Through the above retro-analysis, the starting material was 2-amino-5-nitrobenzonitrile as a diazotizing agent, and as the coupler, starting from 6-dichloro-4-methylnicotinonitrile, - (2-aminoethoxy) ethan-1-ol in that order.
이하 실시 예를 통해 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail with reference to examples.
실시 예 1 6-클로로-4-메틸-2-(페닐아미노)니코티노니트릴 합성Example 1 6-Chloro-4-methyl-2- (phenylamino) nicotinonitrile Synthesis
6-디클로로-4-메틸니코티노니트릴 50g(2.67mol), 아닐린 35g(3.74mol, 1.4eq.), 디메틸포름아미드 50g, Na2CO3 20g(1.88mol, 0.7eq.) 혼합물을 3시간에 걸쳐 92℃까지 승온하여, 12시간 동안 반응시킨 후, TLC로 반응 완결을 확인하였다. 반응 혼합물의 온도를 70℃ 이하로 냉각하여 MeOH (100mL)를 서서히 첨가하여 30℃까지 냉각하였다. 20% 염산 수용액 30g과 정제수 70g 혼합용액을 서서히 적가하여 교반한 후, 정제수 50g을 추가 적가하여 2시간 동안 교반하였다.6-dichloro-4-methyl-nicotinoyl nitrile 50g (2.67mol), and yielded 35g (3.74mol, 1.4eq.), Dimethylformamide 50g, Na 2 CO 3 20g ( 1.88mol, 0.7eq.) Mixture of 3 hours The mixture was heated to 92 DEG C and reacted for 12 hours, and then the completion of the reaction was confirmed by TLC. The temperature of the reaction mixture was cooled to 70 DEG C or lower, and MeOH (100 mL) was gradually added thereto and cooled to 30 DEG C. [ 30 g of a 20% hydrochloric acid aqueous solution and 70 g of purified water were gradually added dropwise and stirred, and 50 g of purified water was further added dropwise and stirred for 2 hours.
이 반응 혼합물을 여과하고 뜨거운 물로 여액이 중성일 때까지 수세하여 아닐린이 치환된 목적물 62.1g(수율 95.5%)을 얻었다. HPLC 데이터는 도 1에 도시하였다. The reaction mixture was filtered and washed with hot water until the filtrate was neutralized to obtain 62.1 g (yield: 95.5%) of the target substance substituted with aniline. The HPLC data are shown in Fig.
실시 예 2 6-(2-히드록시-에틸아미노)-4-메틸-2-(5-페녹시-펜틸아미노)-니코티노니트릴 합성Example 2 Synthesis of 6- (2-hydroxy-ethylamino) -4-methyl-2- (5-phenoxy- pentylamino) -nicotinonitrile
PEG 400 46g에 2-(2-아미노에톡시)에탄-1-올 22g(2.08 mol, 1.64eq.)를 가하고, 실시 예 1의 생성물 31g(1.27mol)과 Na2CO3 10g(0.94mol, 0.7eq.)을 가하여 교반하며 승온하였다. 반응 중 생성된 물을 제거하면서 반응온도를 115℃까지 약 3시간에 걸쳐 승온한 후, 약 12시간 동안 반응시켰다. 반응물의 온도를 80℃까지 냉각하여 TLC로 반응 완료를 확인 한 후, 60℃ 이하로 냉각하고, 정제수 20g과 MeOH 100㎖를 서서히 가하여 완전히 풀어 주었다. 이때 별도의 정제 과정 없이 얻어진 반응 혼합물을 다음 반응에 사용하기로 하였다. HPLC 데이터는 도 1에 도시하였다. 2-
실시 예 3 커플링Example 3 Coupling
진한 황산 73g, 프로피온산 7g, 아세트산 29g 혼합 산 용매에 상온에서 2-ㅇ아미노-5-니트로벤조니트릴 20g(1.22mol)을 완전히 용해 시키고, 5℃ 이하로 냉각 한 후, 승온되지 않게 주의하면서 43% NSA 44g(1.28 mol, 1.05 eq.)를 서서히 가하여 니트로소 화합물을 생성 시킨다(약 3시간 소요).20 g (1.22 mol) of 2-amino-5-nitrobenzonitrile was completely dissolved in 73 g of concentrated sulfuric acid, 7 g of propionic acid and 29 g of acetic acid and the mixture was cooled to 5 ° C or lower. 44 g (1.28 mol, 1.05 eq.) Of NSA are slowly added to form the nitroso compound (takes about 3 hours).
실시 예 2에서 얻어진 커플러 반응 용액에 MeOH 100㎖를 더 가하여 흐름성을 좋게 만들어 놓고, 여분의 비이커에 물(350㎖)과 얼음(200g), SM-acid 0.5g, 유화제 0.5g을 가하여 교반한 후, 이 용액에 디아조 혼합물 및 커플러 혼합액을 동시에 3시간에 걸쳐 적가한다.Water (350 ml) and ice (200 g), 0.5 g of SM-acid and 0.5 g of emulsifier were added to the excess beaker, and the mixture was stirred Then, the diazo mixture and the coupler mixture are added dropwise to this solution at the same time over 3 hours.
이때 반응 온도는 0℃ 이하를 유지하기 위해 여분의 얼음을 추가할 수 있다. 적가가 완료된 후, 그 온도에서 3시간동안 유지 교반하여 반응을 완료시킨다. 반응이 완료되면 20℃ 이하에서 NaOH 수용액으로 반응물의 pH를 2~2.5로 조정하고 실온에서 3시간 동안 유지 교반한다. 이 반응 혼합물의 온도를 80~85℃로 승온하여 약 2시간 동안 유지하면서 생성된 염료 입자를 숙성시킨 후, 여과, 수세 과정을 거친다. 여액이 중성이 될 때까지 세척하여 신규 적색 염료 56.3g(수율 95%)을 얻었다.At this time, the reaction temperature can be increased by adding extra ice to keep the temperature below 0 ° C. After the dropwise addition is completed, the reaction is completed by maintaining stirring at that temperature for 3 hours. When the reaction is complete, the pH of the reaction mixture is adjusted to 2 to 2.5 with NaOH aqueous solution at 20 ° C or less, and the mixture is stirred at room temperature for 3 hours. The temperature of the reaction mixture is raised to 80 to 85 ° C, maintained for about 2 hours, and the resulting dye particles are aged and then filtered and washed. The filtrate was washed until it became neutral to obtain 56.3 g (yield: 95%) of a new red dye.
HPLC 데이터는 도 1에 도시하였다. The HPLC data are shown in Fig.
흡수곡선을 디스퍼스 레드와 비교한 데이터를 도 2에 도시하였다. 동일 농도에서 본 발명의 신규적색 염료의 흡수 강도가 월등히 높음을 알 수 있다. Data comparing the absorption curve with the disperse red is shown in Fig. The absorption intensity of the novel red dye of the present invention is remarkably high at the same concentration.
내광성 시험을 MS 210-05 4.5에 따라 한국의류시험연구원에 의뢰하여 실시하였다. 조사량은 84 MJ/㎡로 실시하였고, 변퇴색 판정은 Gray scale (변퇴색용 표준회색색표)를 이용하였다. 색차 측정 조건은 D65/10°, 45°/0°, 조사조도는 65.5 ± 2.5 W/㎡ (300∼400nm)였다. 외관은 육안으로 확인되는 변색이나 퇴색이 없었고, 변퇴색(급)은 4였으며 색차(△E*)는 2.17이었다. The light resistance test was carried out by the Korean Institute of Clothing and Textiles under MS 210-05 4.5. The irradiation dose was 84 MJ / ㎡. Gray scale (standard gray color chart for fading color) was used for the discoloration determination. The color difference measurement conditions were D65 / 10 ° and 45 ° / 0 °, and the irradiation intensity was 65.5 ± 2.5 W / m2 (300 to 400 nm). There was no discoloration or discoloration visible to the naked eye, and the discoloration (grade) was 4 and the color difference (ΔE *) was 2.17.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020160157952A KR101942305B1 (en) | 2016-11-25 | 2016-11-25 | Pyridine red disperse dye composition and preparing method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020160157952A KR101942305B1 (en) | 2016-11-25 | 2016-11-25 | Pyridine red disperse dye composition and preparing method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20180058964A KR20180058964A (en) | 2018-06-04 |
| KR101942305B1 true KR101942305B1 (en) | 2019-01-25 |
Family
ID=62628160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020160157952A Expired - Fee Related KR101942305B1 (en) | 2016-11-25 | 2016-11-25 | Pyridine red disperse dye composition and preparing method thereof |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR101942305B1 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020151235A1 (en) | 2000-11-27 | 2002-10-17 | Heike Bartl | Dyed and/or printed nonwoven fabric |
| JP2004339514A (en) | 2003-05-14 | 2004-12-02 | Dystar Textilfarben Gmbh & Co Deutscheland Kg | Disperse dye mixture |
| JP2006057004A (en) | 2004-08-20 | 2006-03-02 | Sumitomo Chemical Co Ltd | Disperse dye composition |
| KR101238117B1 (en) | 2004-06-10 | 2013-03-04 | 이 아이 듀폰 디 네모아 앤드 캄파니 | Poly(trimethylene terephthalate) fibers useful in high-uv exposure end uses |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR840001198B1 (en) * | 1981-03-16 | 1984-08-18 | 야마하 하쓰도오기 가부시기 가이샤 | Starting device for multi-fuel carburetor |
-
2016
- 2016-11-25 KR KR1020160157952A patent/KR101942305B1/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020151235A1 (en) | 2000-11-27 | 2002-10-17 | Heike Bartl | Dyed and/or printed nonwoven fabric |
| JP2004339514A (en) | 2003-05-14 | 2004-12-02 | Dystar Textilfarben Gmbh & Co Deutscheland Kg | Disperse dye mixture |
| KR101238117B1 (en) | 2004-06-10 | 2013-03-04 | 이 아이 듀폰 디 네모아 앤드 캄파니 | Poly(trimethylene terephthalate) fibers useful in high-uv exposure end uses |
| JP2006057004A (en) | 2004-08-20 | 2006-03-02 | Sumitomo Chemical Co Ltd | Disperse dye composition |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20180058964A (en) | 2018-06-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2771406B1 (en) | A bis-quinophthalone pigment and a process for preparing the same | |
| CH626389A5 (en) | ||
| US20040039182A1 (en) | Mono-and bis-hydrazone pigments | |
| JPH0713070B2 (en) | Thiofene-containing compound and process for producing the same | |
| KR101942305B1 (en) | Pyridine red disperse dye composition and preparing method thereof | |
| Gong et al. | Trisazo direct black dyes based on nonmutagenic 3, 3′-disubstituted benzidines | |
| US4354969A (en) | Dye mixtures | |
| US3108109A (en) | Process for producing quinoline yellow dyes | |
| KR100735711B1 (en) | Fluorescent Whitening Agent and Synthesis Method thereof | |
| Patel et al. | Monoazo disperse dyes derived from 11H-7-amino-2-chloro-isoindolo [2, 1-a] benzimidazole-11-one | |
| EP0281920A2 (en) | Dyestuffs with N-(2-aminomethyle)-piperazine groups and their use | |
| US9062000B2 (en) | Bis-quinaldine compound and a process for preparing the same | |
| JP4452420B2 (en) | New compounds | |
| US4081446A (en) | Process for the preparation of 4-amino-1,8-naphthalic acid-N-arylimides | |
| DE2617062C2 (en) | Water-soluble hydrazones of the phthalocyanine series, their production and use | |
| DE2308585A1 (en) | REACTIVE COLORS | |
| US1763216A (en) | Hans th | |
| Patel et al. | Synthesis and evaluation of a series of symmetrical hot brand bis azo reactive dyes using 4, 4′-methylene-bis-metanilic acid on various fibre | |
| JP2002309117A (en) | Monoazo compound, aminobenzothiazole derivative and method for producing the same | |
| DE4219421A1 (en) | Process for the production of fiber-reactive formazan dyes and aminophenols | |
| DE2617087C3 (en) | Process for the production of phthalocyanine azo dyes and their use for dyeing and printing cellulosic materials, cellulosic materials, and natural and synthetic polyamide materials | |
| CH620197A5 (en) | ||
| US5811529A (en) | Bis-pyridone compounds | |
| US334257A (en) | alexandee maetitjs | |
| SU1685927A1 (en) | 1,1'-binaphthyl-4,4',5,5'-tetracarboxy-8,8'-disulphoacid or its dianhydride as an intermediate product for synthesis of vat dyes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 20161125 |
|
| PA0201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20180521 Patent event code: PE09021S01D |
|
| PG1501 | Laying open of application | ||
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20181019 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 20190121 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 20190121 End annual number: 3 Start annual number: 1 |
|
| PG1601 | Publication of registration | ||
| PC1903 | Unpaid annual fee |
Termination category: Default of registration fee Termination date: 20221101 |