KR20040104856A - Antibacterial azo dye having sulfanilamides as diazo-component - Google Patents
Antibacterial azo dye having sulfanilamides as diazo-component Download PDFInfo
- Publication number
- KR20040104856A KR20040104856A KR1020030036115A KR20030036115A KR20040104856A KR 20040104856 A KR20040104856 A KR 20040104856A KR 1020030036115 A KR1020030036115 A KR 1020030036115A KR 20030036115 A KR20030036115 A KR 20030036115A KR 20040104856 A KR20040104856 A KR 20040104856A
- Authority
- KR
- South Korea
- Prior art keywords
- antibacterial
- azo dye
- diazo
- sulfanilamides
- antimicrobial
- Prior art date
Links
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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/08—Disazo dyes in which the coupling component is a hydroxy-amino compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
본 발명은 설파제를 디아조체로 하는 항균성 아조염료(antibacterial azo dye)에 관한 것이다.The present invention relates to an antibacterial azo dye comprising sulfa as a diazo.
아조기(-N-=N-)를 발색단으로 하는 염료를 아조염료라고하는데 일반적으로 아조 염료는 방향족 아민을 디아조화하고 이를 방향족 아민이나 페놀류에 결합시켜 제조되는데 여기에서 디아조화되는 방향족 아민을 디아조체라고 하며 페놀류를 아조체라 한다.Azo dyes, which are chromophores with azo groups (-N- = N-), are called azo dyes. Generally, azo dyes are prepared by diazotizing aromatic amines and binding them to aromatic amines or phenols. Phenols are called azo bodies.
다음 구조식 (I)의 모핵을 갖는 화학요법제를 설파제라 하는데Chemotherapeutic agents with the parent nucleus of formula (I)
설파제(sulfanilamide and its delivertives)는 미생물 발육의 필수인자인엽산(folic acid)을 미생물이 합성하는 것을 억제 시켜주는 특성을 갖고있어 광범위한 세균에 대한 정균(靜菌)작용이 있는 것으로 알려져 있다. 최근에는 새로 개발되는 우수한 항생제들이 설파제를 대체하여 사용되고 있기는 하지만 아직도 항균제로서 광범위하게 사용되고 있는 물질이다.Sulfanilamide and its delivertives are known to have bacteriostatic effects on a wide range of bacteria because they inhibit the synthesis of folic acid, an essential factor in microbial growth. Recently, excellent newly developed antibiotics have been used as a substitute for sulfa, but are still widely used as antibacterial agents.
종래 직물에 대한 항균처리방법으로서는 은사(銀絲: 은을 함유하는 실)을 섞어 직물을 제조하거나 직물에 항균물질을 패딩(padding)하는 방법으로 직물에 항균성을 부여하고 있으나 은사를 섞어 제조된 직물은 물리적 성질에 제한을 받게되어 용도에 있어서도 제한이 따르게될 뿐 아니라 항균력이 떨어지는 문제가 있고 항균물질을 패딩하는 방법은 지속적인 항균력을 유지시켜 주지 못한다는 문제가 있다.As an antimicrobial treatment method for a conventional fabric, a fabric is prepared by mixing silver (銀絲: silver-containing thread) or by padding an antimicrobial substance on the fabric. Silver is restricted in physical properties, so there are limitations in use as well as a drop in antimicrobial activity, and there is a problem in that the method of padding antimicrobial material does not maintain a continuous antimicrobial activity.
따라서 이분야에서는 직물에 나쁜 영향을 미치지 않으면서 직물에 지속적인 향균력을 유지 시켜 줄 수 있는 염료의 개발이 요망되는 실정에 있다.Therefore, in this field, it is desired to develop a dye that can maintain a continuous antimicrobial power on a fabric without adversely affecting the fabric.
본 발명의 목적은 설파제를 디아조체로 하는 항균성 아조염료를 제공하는데 있다.It is an object of the present invention to provide an antimicrobial azo dye comprising sulfa as a diazo.
본 발명자들은 설파제가 방향족 아민과 유사한 화학구조를 갖고있어 아조염료의 디아조체로 이용될 수 있는 점에 착안하여 설파제와 종래 아조염료에서 아조체로 이용되고 있는 화합물을 반응시켜 아조 염료를 제조하게 되면 이들 아조염료도 항균성을 나타내게 된다는 점을 확인하여 본 발명을 완성하게 되었다.The present inventors pay attention to the fact that sulfases have a chemical structure similar to aromatic amines and thus can be used as diazos of azo dyes. The present invention was completed by confirming that azo dyes also exhibit antimicrobial properties.
본 발명은 설파제를 디아조체로 하는 다음 일반식(Ⅱ)으로 표시되는 항균성 아조염료에 관한 것이다.The present invention relates to an antimicrobial azo dye represented by the following general formula (II) having sulfa as a diazo.
상기 식에서In the above formula
A는 설파제로서A is a sulfa
R1R2는 OH 또는 NH2이다R 1 R 2 is OH or NH 2
상기 B에서 -OSO3Na는 Cl로 대체될 수 있다.-OSO 3 Na in B may be replaced with Cl.
상기 일반식(Ⅱ)으로 표시되는 화합물들은 청색의 염료들이다.The compounds represented by the general formula (II) are blue dyes.
또한 잘알려져 있는 설파제에는 다음과 같은 것이 있다Also, the well-known sulfa drugs include:
이하 실시예를 들어 본 발명을 구체적으로 설명한다.The present invention will be described in detail with reference to the following Examples.
(실시예 1)(Example 1)
일반식(Ⅱ)로 표시될 수 있는 다음 구조식(Ⅲ)의 청색염료화합물의 제조Preparation of Blue Dye Compound of Formula (III) Which Can Be Represented by Formula (II)
실버설파다이아진 398부를 빙수에 넣은후 염산 27.1부를 가하고 아초산 6.9부를 천천히 가하면서 디아조 반응을 진행한다.Was placed in ice water with silver diamine sulfamic Gene 39 8 parts of hydrochloric acid was added 27.1 parts of nitrite 6.9 parts of a diazonium reaction proceeds as slowly.
상기 반응에서 얻어진 디아조늄 이온에 H-acid 31.9부를 가하고 PH를 3.5~3.8로 정확하게 유지 하면서 산성 커플링을 진행한다.It was added to the diazonium ion obtained in the above reaction H-acid 31. 9 parts of the PH 3. 5 ~ 3. Proceed with acidic coupling, keeping 8 as accurate.
별도의 반응기에 염화시아눌 18.4부를 빙수에 넣고 분산제 0.1부를 가한다음 1시간정도 분산시킨 후 중성에서 용해된 MPDSa(m-phenylene diamine sulfomic acid) 18.8부를 분산된 염화시아눌액에 가하고 PH를 5.0~6.5로 조정하여 1차 축합을 진행한다.In press cyano chloride in a separate reactor, 18.4 parts put into ice water dispersant 0.1 dissolved in a neutral then was added, and then dispersed for 1 hour parts MPDSa (m-phenylene diamine sulfomic acid ) 18. 8 cyano chloride dispersed portion nulaek Adding PH 5. 0-6 . Adjust to 5 to proceed with the first condensation.
여기에서 얻어진 화합물을 상기한 바와 같은 방법으로 디아조반응을 진행한다.The compound obtained here is subjected to a diazo reaction in the same manner as described above.
상기커플링 반응에서 얻은 액에 상기축합반응에서 얻은 디아조늄 이온을 가하고 온도를 5℃ PH를 중성으로 하여 알카리 커플링을 진행한다.The diazonium ion obtained by the said condensation reaction is added to the liquid obtained by the said coupling reaction, and alkali coupling is performed by making temperature 5 degreeC neutral.
여기에서 얻어진 청색의 항균염료에 m-base 28.1부를 가하고 온도를 40℃로 승온하고 PH를 8.0조정하면서 2차 축합을 진행하여 2차 축합이 종결되면 최종 목적 화합물인 청색 항균염료가 완성된다.Antibacterial dyes of blue obtained here m-base 28. 1 parts was added and temperature was raised to 40 ℃ and the PH 8. 0 adjust secondary When the condensation proceeds to the second condensation was completed, the final target compound as a blue dye antibacterial Is completed.
<항균성 시험>Antimicrobial Test
상기 실시예에서 얻어진 화합물의 0.5% 수용액에 망초를 가하여 염색액을 만든다. 여기에 면직물을 가하고 60℃로 승온 후 20% 소다회 용액을 가하여 염착시킨다. 60℃로 60분정도 유지 후 소핑과 건조를 거쳐 염직물을 얻고 이염직물의 항균성 시험 결과를 다음[표1]에 나타냈다.To the 0.5% aqueous solution of the compound obtained in the above example was added forget-me-not to form a dye solution. A cotton fabric is added thereto, and the resultant is heated to 60 ° C., followed by dyeing by adding 20% soda ash solution. After holding at 60 ° C. for about 60 minutes, the dyeing material was obtained by soaping and drying, and the antimicrobial test results of the dyestuff material are shown in [Table 1].
(실시예2)Example 2
다음 일반식(Ⅱ)로 표시될 수 있는 다음 구조식(Ⅳ)의 청색염료의 제조Preparation of blue dye of the following structural formula (IV) which can be represented by the following general formula (II)
실버 설파다이아진과 H-산(H-acid)의 산성 커플링 공정은 실시예1과 동일한 방법을 사용하였다.The acidic coupling process of silver sulfadiazine and H-acid (H-acid) used the same method as in Example 1.
MPDSa 18.8부를 PH 7에서 용해시킨후 5℃이하로 냉각시키고 TFCP(5-chloro-2,4,6-trifluropyrimidine) 168부를 가하고 PH를 6~9사이로 유지시키면서 축합반응을 진행한다.MPDSa 18. advances the cooling unit 8 to less than 5 ℃ was dissolved in PH 7 and TFCP (5-chloro-2,4,6- trifluropyrimidine) was added 168 parts of a condensation reaction while maintaining the PH between 6 and 9.
축합반응이 종결되면 실시예 1과 동일한 방법으로 디아조 반응을 진행한다.When the condensation reaction is terminated, the diazo reaction is performed in the same manner as in Example 1.
상기 커플링 공정에서 얻어진 화합물과 축합반응에서 얻어진 화합물을 합친후 온도는 5℃ 이하에서 PH는 중성으로 하여 최종목적화합물을 얻는다.After the compound obtained in the coupling step and the compound obtained in the condensation reaction are combined, the pH is neutral at a temperature of 5 ° C. or lower to obtain a final target compound.
본 발명의 항균염료는 세탁후에도 항균력이 소멸되지 않아 지속적인 항균능력을 유지 할 수 있는 항균직물을 제공할 수 있는 효과가 있다.The antimicrobial dye of the present invention has an effect that can provide an antimicrobial fabric that can maintain a continuous antimicrobial ability does not disappear even after washing the antimicrobial power.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020030036115A KR100544947B1 (en) | 2003-06-04 | 2003-06-04 | Antibacterial azo dye having sulfanilamides as diazo-component |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020030036115A KR100544947B1 (en) | 2003-06-04 | 2003-06-04 | Antibacterial azo dye having sulfanilamides as diazo-component |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20040104856A true KR20040104856A (en) | 2004-12-13 |
KR100544947B1 KR100544947B1 (en) | 2006-01-24 |
Family
ID=37380099
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020030036115A KR100544947B1 (en) | 2003-06-04 | 2003-06-04 | Antibacterial azo dye having sulfanilamides as diazo-component |
Country Status (1)
Country | Link |
---|---|
KR (1) | KR100544947B1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100821896B1 (en) * | 2005-02-23 | 2008-04-16 | 주식회사 코오롱 | Antibacterail acid dyes containing silver and a method of preparing the same and antibacterial fiber thereby |
-
2003
- 2003-06-04 KR KR1020030036115A patent/KR100544947B1/en not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100821896B1 (en) * | 2005-02-23 | 2008-04-16 | 주식회사 코오롱 | Antibacterail acid dyes containing silver and a method of preparing the same and antibacterial fiber thereby |
Also Published As
Publication number | Publication date |
---|---|
KR100544947B1 (en) | 2006-01-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US11370921B2 (en) | Reactive dye compound and preparation method and application thereof | |
US8409300B2 (en) | Disperse azo dyes | |
US9938411B2 (en) | Disperse azo dyes | |
KR100544951B1 (en) | Antibacterial azo dye having sulfanilamides as diazo-component | |
JPS6218473A (en) | Aqueous liquid reactive dye composition | |
KR840000609B1 (en) | Manufacturing process of reactive dye | |
KR100544947B1 (en) | Antibacterial azo dye having sulfanilamides as diazo-component | |
KR101801993B1 (en) | Disperse Dyes | |
US3900460A (en) | Water-soluble disazo compounds containing a pyrazole component | |
DE60121363T2 (en) | DISORZOES AND THEIR COPPER COMPLEXES FOR PAPERING | |
US5997587A (en) | Azo dye mixtures, azo dyes, processes for their preparation, and their use | |
KR20150050817A (en) | Composition of reactive orange dyes | |
KR100910177B1 (en) | High light fastness antibiotic acid dye and synthetic method thereof | |
JPS6281455A (en) | Trisazo compound | |
KR20090038947A (en) | Antibiotic yellow azo dyes | |
JPH02117962A (en) | Metal complex compound | |
JP3090487B2 (en) | New azo black dye | |
US3814749A (en) | Blue phenylazonaphthylazo-n-aryl peri acids | |
JP2002539316A (en) | Azoxy dyes and their copper complexes | |
KR100896308B1 (en) | Dye composition comprising acid dye compound having antimicrobial activity | |
US4227879A (en) | Concentrated direct dye solution | |
US6028179A (en) | Trisazo dyes | |
US4211697A (en) | Azoanilino-toluene sulfonamidoalkyleneamine cationic dyes for paper | |
JPS62250058A (en) | Azo dye | |
KR100411189B1 (en) | Disperse-reactive dyes containing vinyl sulfone moiety |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
E701 | Decision to grant or registration of patent right | ||
N231 | Notification of change of applicant | ||
GRNT | Written decision to grant | ||
LAPS | Lapse due to unpaid annual fee |