CN101570648B - 一种红分散染料 - Google Patents
一种红分散染料 Download PDFInfo
- Publication number
- CN101570648B CN101570648B CN 200910115470 CN200910115470A CN101570648B CN 101570648 B CN101570648 B CN 101570648B CN 200910115470 CN200910115470 CN 200910115470 CN 200910115470 A CN200910115470 A CN 200910115470A CN 101570648 B CN101570648 B CN 101570648B
- Authority
- CN
- China
- Prior art keywords
- hydrogen
- nitro
- red
- dye
- methyl
- 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.)
- Active
Links
- 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 title claims abstract description 10
- 239000001044 red dye Substances 0.000 title claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 14
- 230000008878 coupling Effects 0.000 claims abstract description 12
- 238000010168 coupling process Methods 0.000 claims abstract description 12
- 238000005859 coupling reaction Methods 0.000 claims abstract description 12
- -1 monoazo compound Chemical class 0.000 claims abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 11
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 4
- 239000003513 alkali Substances 0.000 claims abstract description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical group [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims abstract 2
- CHJVFEINHNDFKC-UHFFFAOYSA-N phenyl 3-aminobenzenesulfonate Chemical compound NC1=CC=CC(S(=O)(=O)OC=2C=CC=CC=2)=C1 CHJVFEINHNDFKC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 3
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000006193 diazotization reaction Methods 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 10
- 239000000460 chlorine Chemical group 0.000 abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 abstract description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 5
- 238000005406 washing Methods 0.000 abstract description 3
- 238000000859 sublimation Methods 0.000 abstract description 2
- 230000008022 sublimation Effects 0.000 abstract description 2
- 210000004243 sweat Anatomy 0.000 abstract description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000049 pigment Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 229960005081 diclofenamide Drugs 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 3
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 3
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 2
- HWTDMFJYBAURQR-UHFFFAOYSA-N 80-82-0 Chemical group OS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O HWTDMFJYBAURQR-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000004308 accommodation Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
本发明涉及一种红分散染料，主要包括如下式的单偶氮化合物，
Description
技术领域
本发明涉及一种分散染料，尤其涉及一种红分散染料。
背景技术
聚酯染色所需的分散染料应具有以下特点：高强度、高染色牢度、较好的匀染性和提升率；目前国外染料供应商推荐的红分散染料品种为C.I.167、分散红C.I.R167，商品强度较低，对聚酯类纤维染色时，染料用量多、牢度差极易褪色、PH适应范围小，因此亟需要改进。
发明内容
本发明提供了一种红分散染料，克服了现有技术存在的上述缺陷。
为达到上述发明目的本发明所采用的技术方案是：一种红分散染料，主要包括如下式的单偶氮化合物，
式中：
R为甲基、乙基、甲氧基丙基，
X为氢、氯、硝基、甲氧基，
Y为氢、氯、硝基、磺酸苯酯基，
Z为氢、氯、甲基、甲氧基、硝基。
所述X为氯、硝基、甲氧基。
所述Y为氯、硝基、磺酸苯酯基。
所述Z为氯、硝基。
所述单偶氮化合物是按如下步骤制作的：在盐酸介质中，加入胺基物，用亚硝酸钠进行重氮，重氮的产物和红中间体在碱液里偶合。
所述红中间体为4-羟基-N-甲基-1,8-萘酰亚胺。
所述胺基物为对硝基苯胺、邻氯对硝基苯胺、红色基3GL、邻甲氧基对硝基苯胺、间氨基苯磺酸苯酯、苯胺、2，5-二氯苯胺、3，4-二氯苯胺、邻硝基苯胺或间硝基苯胺。
本发明的优点：具有很强的日晒牢度和较强的水洗牢度、升华牢度，受汗渍、摩擦的影响小，PH适应范围广。
具体实施方式
实施例1：
将10ml30%的盐酸放入烧瓶内，加入20ml、4g对硝基苯胺，升温至95度，保温1小时后，降温至30度，加入40ml水，再加入30g冰，同进用冰浴保持瓶内温度在0-5度，加入2.5g亚硝酸钠10%的溶液，保持反应2小时，在完成反应后，于0-5度在2小时后，将上述混合物加入由20ml冰水、4gNaOH和4-羟基-N-甲基-1,8-萘酰亚胺（简称红中间体、结构见下式）组成的混合物中。
继续搅拌2小时后，滴加5ml盐酸，继续搅拌1小时，升温到80度，并保温2小时，所得染料进行抽滤，用清水洗涤并干燥，反应产物为：
R=CH3、CH2CH3或CH2CH2CH2OCH3，入max=520nm。染料经后处理，染聚酯后成艳黄光红色。
实施例2～10：
依次将实施例1中的对硝基苯胺换成邻氯对硝基苯胺、红色基3GL、邻甲氧基对硝基苯胺、间氨基苯磺酸苯酯、苯胺、2，5-二氯苯胺、3，4-二氯苯胺、邻硝基苯胺、间硝基苯胺，保持其它条件不变，反应产物分别为：
邻氯对硝基苯胺和红中间体偶合
红色基3GL和红中间体偶合
邻甲氧基对硝基苯胺和红中间体偶合
R=CH3、CH2CH3或CH2CH2CH2OCH3，入max=550nm
间氨基苯磺酸苯酯和红中间体偶合
R=CH3、CH2CH3或CH2CH2CH2OCH3，入max=510nm
苯胺和红中间体偶合
2，5-二氯苯胺和红中间体偶合
3，4-二氯苯胺和红中间体偶合
邻硝基苯胺和红中间体偶合
间硝基苯胺和红中间体偶合
R=CH3、CH2CH3或CH2CH2CH2OCH3，入max=500nm
染料经后处理，染聚酯后成艳黄光红色。
对上述10个实施例中的染料按GB/T3921-1997GB/T3920-1997GB/T5718-1997测试其牢度，得到各项牢度指标如下表数据：
Claims (2)
1.一种红分散染料，包括如下式的单偶氮化合物：
式中：
R为甲基、乙基、甲氧基丙基，
X为氢，
Y为磺酸苯酯基，
Z为氢。
2.根据权利要求1所述的红分散染料，其特征在于所述单偶氮化合物是按如下步骤制作的：在盐酸介质中，加入间氨基苯磺酸苯酯，用亚硝酸钠进行重氮化，重氮化的产物和红中间体在碱液里偶合，所述红中间体为4-羟基-N-甲基-1,8-萘酰亚胺。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200910115470 CN101570648B (zh) | 2009-06-01 | 2009-06-01 | 一种红分散染料 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200910115470 CN101570648B (zh) | 2009-06-01 | 2009-06-01 | 一种红分散染料 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101570648A CN101570648A (zh) | 2009-11-04 |
| CN101570648B true CN101570648B (zh) | 2013-11-06 |
Family
ID=41230139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200910115470 Active CN101570648B (zh) | 2009-06-01 | 2009-06-01 | 一种红分散染料 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101570648B (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102093756B (zh) * | 2011-01-12 | 2013-08-28 | 浙江山峪染料化工有限公司 | 一种节能型偶氮类分散染料的制备方法 |
| CN106748810B (zh) * | 2016-12-30 | 2021-04-27 | 浙江闰土研究院有限公司 | 一种分散染料中间体的处理方法 |
-
2009
- 2009-06-01 CN CN 200910115470 patent/CN101570648B/zh active Active
Non-Patent Citations (4)
| Title |
|---|
| A T Peters et al.4-Hydroxy-3-arylamino-1,8-naphthalimides and 3-(and 4-) hydroxy-2-(and 5-) arylamino-7H-benzimidazo-(2,1 -a)benz(d ,e )isoquinolin-7-one. Red dyes for synthetic-polymer fibres.《Journal of the Society of Dyers and Colourists》.1990,第106卷第275-280页. |
| A T Peters et al.4-Hydroxy-3-arylamino-1,8-naphthalimides and 3-(and 4-) hydroxy-2-(and 5-) arylamino-7H-benzimidazo-(2,1-a)benz(d,e )isoquinolin-7-one. Red dyes for synthetic-polymer fibres.《Journal of the Society of Dyers and Colourists》.1990,第106卷第275-280页. * |
| JP昭54-17735 1979.02.09 |
| JP特开2005－29750A 2005.02.03 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101570648A (zh) | 2009-11-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102604413B (zh) | 一种中温型分散染料化合物及其制备方法与应用 | |
| JP5922034B2 (ja) | 分散アゾ染料 | |
| EP2655518B1 (en) | Disperse azo dyes | |
| KR100847236B1 (ko) | 아조 염료, 염료 혼합물, 이들의 제조방법 및 이들을 사용한 소수성 섬유 재료의 염색 또는 날염 방법 | |
| ES2415929T3 (es) | Colorantes azoicos, procedimiento para la preparación de los mismos y uso de los mismos | |
| CN101570648B (zh) | 一种红分散染料 | |
| CN101245195B (zh) | 一种杂环偶氮阳离子染料及其制备方法 | |
| US2109552A (en) | Azo dyestuffs and their metalliferous derivatives | |
| ES2943652T3 (es) | Colorantes azo dispersados | |
| ES2354500T3 (es) | Colorantes azoico de ftalimidilo, procedimiento para la preparacion del mismo y el uso del mismo. | |
| CN101143970B (zh) | 一种染料化合物及其制备方法和用途 | |
| US2634263A (en) | Monoazo dyestuffs | |
| CN102898868A (zh) | 一种活性橙染料及其制备方法 | |
| KR20130092721A (ko) | 폴리에스테르 섬유용 분산염료 및 이를 포함하는 염료 조성물 | |
| CN103881412A (zh) | 一种单偶氮分散染料化合物及其制备方法 | |
| CN101942215A (zh) | 一种毛用橙色活性染料及其制备方法 | |
| CN105238094B (zh) | 一种具有高发色强度的红光蓝色偶氮分散染料及其制备方法 | |
| CN104478743B (zh) | 一种苯胺类化合物、其制备及应用 | |
| EP0923622B1 (en) | 1:2 iron azo-dyestuff complexes | |
| CN101792613B (zh) | 一种黄色毛用活性染料及其制备方法及用途 | |
| KR100686978B1 (ko) | 반응성 염료 조성물 및 이를 이용한 섬유의 염색방법 | |
| CN103952004B (zh) | 一种高温型分散棕染料化合物及其制备方法 | |
| CN101574665B (zh) | 重氮盐与氨基萘酚磺酸类物质偶合反应的复合催化剂及用途 | |
| ES2728684T3 (es) | Colorantes azoicos de antraquinona | |
| CN113462190B (zh) | 一种具有高水洗牢度的偶氮染料化合物、制备方法及应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| ASS | Succession or assignment of patent right |
Owner name: ZHEJIANG SHANYU DYESTUFF CHEMICAL CO., LTD. Free format text: FORMER OWNER: YAO GUOLAI Effective date: 20110330 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 318000 NO. 306, JIEPAI ROAD, BAIYUN SUBDISTRICT, JIAOJIANG DISTRICT, TAIZHOU CITY, ZHEJIANG PROVINCE TO: 318000 SANSHAN VILLAGE, JIAOJIANG DISTRICT, TAIZHOU CITY, ZHEJIANG PROVINCE |
|
| TA01 | Transfer of patent application right |
Effective date of registration: 20110330 Address after: Three, 318000 mountain village, Jiaojiang District, Zhejiang, Taizhou Applicant after: ZHEJIANG SHANYU DYESTUFF CHEMICAL Co.,Ltd. Address before: 318000, 306, Baiyun Road, Jiaojiang District, Zhejiang, Taizhou Applicant before: Tao Guolai |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| ASS | Succession or assignment of patent right |
Owner name: JIANGSU DI'AN CHEMICAL CO., LTD. Free format text: FORMER OWNER: ZHEJIANG SHANYU DYESTUFF CHEMICAL CO., LTD. Effective date: 20141225 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 318000 TAIZHOU, ZHEJIANG PROVINCE TO: 222523 LIANYUNGANG, JIANGSU PROVINCE |
|
| TR01 | Transfer of patent right |
Effective date of registration: 20141225 Address after: 222523 Jiangsu city of Lianyungang province guannaxian heap ditch town (Chemical Industrial Park) Patentee after: JIANGSU DIAN CHEMICAL Co.,Ltd. Address before: Three, 318000 mountain village, Jiaojiang District, Zhejiang, Taizhou Patentee before: ZHEJIANG SHANYU DYESTUFF CHEMICAL Co.,Ltd. |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20231010 Address after: 333300 Tashan Industrial Zone, Leping Industrial Park, Jingdezhen City, Jiangxi Province Patentee after: LEPING SAFELY PHARMACEUTICAL Co.,Ltd. Address before: 222523 heggou town (Chemical Industrial Park), Gunan County, Lianyungang, Jiangsu Patentee before: JIANGSU DIAN CHEMICAL Co.,Ltd. |