JP2011006671A - Reactive dye composition and dyeing method using the same - Google Patents
Reactive dye composition and dyeing method using the same Download PDFInfo
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- 239000000985 reactive dye Substances 0.000 title claims abstract description 202
- 239000000203 mixture Substances 0.000 title claims abstract description 132
- 238000004043 dyeing Methods 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 31
- 239000000975 dye Substances 0.000 claims abstract description 246
- 239000003513 alkali Substances 0.000 claims abstract description 20
- 229920003043 Cellulose fiber Polymers 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims description 44
- 239000000835 fiber Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 239000003086 colorant Substances 0.000 abstract description 7
- 238000012937 correction Methods 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- 238000009472 formulation Methods 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 235000017550 sodium carbonate Nutrition 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- GCFAQSYBSUQUPL-UHFFFAOYSA-I pentasodium 5-[[4-chloro-6-[3-(2-sulfonatooxyethylsulfonyl)anilino]-1,3,5-triazin-2-yl]amino]-3-[(1,5-disulfonatonaphthalen-2-yl)diazenyl]-4-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].Oc1c(N=Nc2ccc3c(cccc3c2S([O-])(=O)=O)S([O-])(=O)=O)c(cc2cc(cc(Nc3nc(Cl)nc(Nc4cccc(c4)S(=O)(=O)CCOS([O-])(=O)=O)n3)c12)S([O-])(=O)=O)S([O-])(=O)=O GCFAQSYBSUQUPL-UHFFFAOYSA-I 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- -1 t-butoxy group Chemical group 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- UIEBGVDTKLYGTN-UHFFFAOYSA-J tetrasodium;7-[[2-(carbamoylamino)-4-[[4-chloro-6-[3-(2-sulfonatooxyethylsulfonyl)anilino]-1,3,5-triazin-2-yl]amino]phenyl]diazenyl]naphthalene-1,3,6-trisulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C=1C=C(N=NC=2C(=CC3=CC(=CC(=C3C=2)S([O-])(=O)=O)S([O-])(=O)=O)S([O-])(=O)=O)C(NC(=O)N)=CC=1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC(S(=O)(=O)CCOS([O-])(=O)=O)=C1 UIEBGVDTKLYGTN-UHFFFAOYSA-J 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 239000001045 blue dye Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- NSDSIQGBHACTLY-UHFFFAOYSA-N Reactive Blue 5 Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S(O)(=O)=O)C=C1NC(C=1)=CC=C(S(O)(=O)=O)C=1NC(N=1)=NC(Cl)=NC=1NC1=CC=CC(S(O)(=O)=O)=C1 NSDSIQGBHACTLY-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000010014 continuous dyeing Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920000433 Lyocell Polymers 0.000 description 1
- 229920001407 Modal (textile) Polymers 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- HFIYIRIMGZMCPC-YOLJWEMLSA-J remazole black-GR Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(\N=N\C=3C=CC(=CC=3)S(=O)(=O)CCOS([O-])(=O)=O)C(O)=C2C(N)=C1\N=N\C1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 HFIYIRIMGZMCPC-YOLJWEMLSA-J 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 238000007447 staining method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Abstract
Description
本発明は、セルロース繊維又はセルロース繊維含有繊維の染色に適する反応染料組成物及びそれを用いる染色法に関する。 The present invention relates to a reactive dye composition suitable for dyeing cellulose fibers or cellulose fiber-containing fibers, and a dyeing method using the same.
反応染料を用いるセルロース繊維の染色においては、黄色、赤色、及び青色又は紺色の反応染料を三原色用染料として用い、それらを種々の割合で配合して染色する方法が知られている。 In dyeing cellulose fibers using reactive dyes, methods are known in which yellow, red, and blue or amber reactive dyes are used as the three primary color dyes, and they are blended in various proportions.
三原色に使用される反応染料に関しては、各染料のビルドアップ性や均染性が優れていること、三原色の染着速度がほぼ等しく温度依存性が揃っていること、三原色の諸堅牢度が優れていることが必要とされている。更に、実工程に対応できることが特に必要とされる。つまり、一般的に染色物が製品になるには実験室スケール（概ね５〜３０ｇ）、中実験スケール（概ね３〜２０ｋｇ）、工場スケール（概ね１００〜１０００ｋｇ）のステップ段階を踏むが、このスケールに由来する又はセルロース含有材料のセルロース混率による染色浴比を一定にするのは極めて困難である。 Regarding reactive dyes used for the three primary colors, the build-up and leveling properties of each dye are excellent, the dyeing speeds of the three primary colors are almost equal, and the temperature dependence is uniform, and the fastnesses of the three primary colors are excellent. It is necessary to be. Furthermore, it is particularly necessary to be able to deal with actual processes. In other words, in general, a dyed product becomes a product by taking the steps of a laboratory scale (approximately 5 to 30 g), a medium experiment scale (approximately 3 to 20 kg), and a factory scale (approximately 100 to 1000 kg). It is extremely difficult to keep the dye bath ratio constant depending on the cellulose mixing ratio of the cellulose-containing material.
従来の三原色用染料として使用する各染料は、セルロース繊維に対する親和性が異なり、染着挙動が異なるため、染色浴比の変化に伴う濃度や色相の変化による色違いの問題が生じ、色修正・脱色修正が現場では頻繁に行われている現状である。その為、同一の染色浴比変化挙動を示す三原色が染色現場では強く望まれている。
又、染色浴比に伴う問題とは別に、アルカリ添加温度による色違いの問題があり、実験室スケールと工場スケールでの再現性不良が起こっている。
Each dye used as a conventional dye for the three primary colors has different affinity for cellulose fiber and different dyeing behavior, so there is a problem of color difference due to changes in density and hue due to changes in the dye bath ratio. The present situation is that decolorization correction is frequently performed in the field. Therefore, the three primary colors showing the same dye bath ratio change behavior are strongly desired in the dyeing site.
In addition to the problem associated with the dye bath ratio, there is a problem of color difference due to the alkali addition temperature, resulting in poor reproducibility on the laboratory scale and factory scale.
このような問題を解決するために、例えば、下記の特許文献では様々な検討がなされているが、未だ満足な結果は得られていない。
又、特開２０００−１９２３７４号公報には染色再現性に優れる赤色反応染料組成物が記載されているが、溶解性が不十分であり実用化は難しい。
In order to solve such problems, for example, various studies have been made in the following patent documents, but satisfactory results have not yet been obtained.
Japanese Patent Application Laid-Open No. 2000-192374 describes a red reactive dye composition having excellent dye reproducibility, but its solubility is insufficient and practical application is difficult.
本発明は、上記の問題を解決してセルロース繊維又はセルロース繊維含有繊維を再現性よく、均染性もよく、高堅牢度に染色する反応染料組成物及びそれを用いた染色法の開発を目的とする。 The present invention aims to solve the above-mentioned problems and to develop a reactive dye composition for dyeing cellulose fibers or cellulose fiber-containing fibers with good reproducibility, good levelness and high fastness, and a dyeing method using the same. And
上記目的のために、本発明者等は鋭意研究の結果、特定の反応染料を含有する赤色反応染料組成物、特定の反応染料を含有する青色反応染料組成物又は紺色反応染料組成物、特定の黄色反応染料を組み合わせて含有する反応染料組成物とそれを用いる染色方法を見出し、本発明を完成させるに至った。 For the above purpose, the present inventors have intensively studied, and as a result, the red reactive dye composition containing a specific reactive dye, the blue reactive dye composition or the amber reactive dye composition containing a specific reactive dye, The inventors have found a reactive dye composition containing a combination of yellow reactive dyes and a dyeing method using the same, and have completed the present invention.
即ち、本発明は以下の１）〜１４）に関する。
１）遊離酸の形が下記式（１）で示される染料を１０重量％〜４０重量％、遊離酸の形が下記式（２）で示される染料を３０重量％〜６０重量％及び遊離酸の形が下記式（３）で示される染料を１０重量％〜４０重量％含有する赤色反応染料組成物。
1) 10% to 40% by weight of a dye represented by the following formula (1) in the form of the free acid, 30% to 60% by weight of a dye represented by the following formula (2) in the form of the free acid, and free acid A red reactive dye composition containing 10% by weight to 40% by weight of a dye having the form represented by the following formula (3).
２）遊離酸の形が式（１）で示される染料を２０重量％〜３０重量％、式（２）で示される染料を４０重量％〜６０重量％、式（３）で示される染料を２０重量％〜３０重量％含有する前記１）記載の赤色反応染料組成物。 2) 20% by weight to 30% by weight of the dye represented by the formula (1) in the form of the free acid, 40% by weight to 60% by weight of the dye represented by the formula (2), and a dye represented by the formula (3) The red reactive dye composition as described in 1) above, containing 20% by weight to 30% by weight.
３）遊離酸の形が式（４）で示される染料を１０重量％〜９０重量％と、遊離酸の形が式（５）及び式（６）で示される染料からなる群から選ばれる１種以上の染料を１０重量％〜９０重量％含有する青色反応染料組成物。
４）遊離酸の形が式（４）で示される染料を１０重量％〜３０重量％と、遊離酸の形が式（５）及び式（６）で示される染料からなる群から選ばれる１種以上の染料を７０重量％〜９０重量％含有する前記３）記載の青色反応染料組成物。
５）遊離酸の形が式（４）で示される染料を１０重量％〜３０重量％、遊離酸の形が式（５）で示される染料を５０重量％〜６０重量％及び遊離酸の形が式（６）で示される染料を２０重量％〜３０重量％含有する前記３）又は４）に記載の青色反応染料組成物。
4) 10% to 30% by weight of the dye represented by the formula (4) in the free acid form, and 1 selected from the group consisting of the dyes represented by the formulas (5) and (6). The blue reactive dye composition as described in 3) above, which contains 70% by weight to 90% by weight of at least one kind of dye.
5) 10% to 30% by weight of the dye represented by the formula (4) in the free acid form, 50% to 60% by weight of the dye represented by the formula (5), and the free acid form The blue reactive dye composition as described in 3) or 4) above, which contains 20 to 30% by weight of the dye represented by formula (6).
６）遊離酸の形が式（５）で示される染料を５重量％〜９５重量％及び式（７）で示される染料を５重量％〜９５重量％含有する紺色反応染料組成物。
７）遊離酸の形が式（５）で示される染料を８０重量％〜９５重量％及び式（７）で示される染料を５重量％〜２０重量％含有する前記６）記載の紺色反応染料組成物。
6) An amber reactive dye composition containing 5% to 95% by weight of the dye represented by the formula (5) and 5% to 95% by weight of the dye represented by the formula (7).
7) The amber reactive dye according to 6) above, wherein the free acid form contains 80% to 95% by weight of the dye represented by the formula (5) and 5% to 20% by weight of the dye represented by the formula (7). Composition.
８）前記１）又は２）に記載の赤色反応染料組成物と前記３）〜５）のいずれか一項に記載の青色反応染料組成物を含有する反応染料組成物。
９）前記１）又は２）に記載の赤色反応染料組成物と前記６）又は７）に記載の紺色反応染料組成物を含有する反応染料組成物。
１０）前記１）又は２）に記載の赤色反応染料組成物と遊離酸の形が式（８）で示される黄色反応染料を含有する反応染料組成物。
9) A reactive dye composition comprising the red reactive dye composition according to 1) or 2) and the amber reactive dye composition according to 6) or 7).
10) A reactive dye composition comprising the red reactive dye composition according to 1) or 2) above and a yellow reactive dye having a free acid form represented by formula (8).
１１）前記３）〜５）のいずれか一項に記載の青色反応組成物と、遊離酸の形が式（８）で示される黄色反応染料を含有する反応染料組成物。
１２）前記６）又は７）に記載の紺色反応組成物と、遊離酸の形が式（８）で示される黄色反応染料を含有する反応染料組成物。
１３）前記８）又は９）に記載の反応染料組成物と、遊離酸の形が式（８）で示される黄色反応染料を含有する反応染料組成物。
１４）前記８）〜１３）のいずれか一項に記載の反応染料組成物を用いることを特徴とするセルロース繊維又はセルロース繊維含有繊維の染色方法。
11) A reactive dye composition comprising the blue reactive composition according to any one of 3) to 5) above and a yellow reactive dye having a free acid form represented by formula (8).
12) A reactive dye composition comprising the amber reaction composition as described in 6) or 7) above and a yellow reactive dye whose free acid form is represented by formula (8).
13) A reactive dye composition comprising the reactive dye composition according to 8) or 9) above and a yellow reactive dye having a free acid form represented by formula (8).
14) A method for dyeing cellulose fibers or cellulose fiber-containing fibers, wherein the reactive dye composition according to any one of 8) to 13) is used.
本発明の反応染料組成物は、特定の反応染料を含有する赤色反応染料組成物、特定の反応染料を含有する青色反応染料組成物、特定の反応染料を含有する紺色反応染料組成物、特定の黄色反応染料を組み合わせて含有し、それを用いる染色により染色浴比の変化により色相が変わることが無く、且つ、濃度補正をする係数を掛け合わせて染色することで常に同様な濃度、色相を得ることができ、更に、アルカリ添加温度による色相変化も無く、セルロース繊維を再現性よく、高堅牢度に染色できる染色方法を提供する。 The reactive dye composition of the present invention comprises a red reactive dye composition containing a specific reactive dye, a blue reactive dye composition containing a specific reactive dye, an amber reactive dye composition containing a specific reactive dye, and a specific reactive dye composition. Contains yellow reactive dyes in combination, and there is no change in hue due to changes in the dyeing bath ratio due to dyeing using them, and the same density and hue are always obtained by dyeing with a coefficient for density correction. Furthermore, the present invention provides a dyeing method capable of dyeing cellulose fibers with high reproducibility and high fastness without hue change due to alkali addition temperature.
本発明の赤色反応染料組成物に含有される遊離酸の形が式（１）で示される染料は特許文献５に、遊離酸の形が式（２）で示される染料は特開２０００−１９２３７４号公報等に、遊離酸の形が式（３）で示される染料は特公平７−９１４８３号公報等に記載されている。しかしながら、それらの染料を含有する赤色反応染料組成物については知られていない。本発明の赤色反応染料組成物に含有される式（１）〜式（３）で示される染料は、該赤色反応染料組成物に対して式（１）で示される染料を１０重量％〜４０重量％、式（２）で示される染料を３０重量％〜６０重量％及び遊離酸の形が下記式（３）で示される染料を１０重量％〜４０重量％含有するのが好ましい。特に式（１）で示される染料を２０重量％〜３０重量％、式（２）で示される染料を４０重量％〜６０重量％、式（３）で示される染料を２０重量％〜３０重量％含有するのが好ましい。 The dye having the free acid form represented by the formula (1) contained in the red reactive dye composition of the present invention is disclosed in Patent Document 5, and the dye having the free acid form represented by the formula (2) is disclosed in JP-A 2000-192374. Japanese Patent Publication No. 7-91483 discloses a dye having a free acid form represented by the formula (3). However, red reactive dye compositions containing these dyes are not known. The dye represented by the formula (1) to the formula (3) contained in the red reactive dye composition of the present invention is 10% by weight to 40% by weight of the dye represented by the formula (1) with respect to the red reactive dye composition. It is preferable to contain 30% to 60% by weight of the dye represented by the formula (2) and 10% to 40% by weight of the dye represented by the following formula (3) in the form of the free acid. In particular, the dye represented by the formula (1) is 20 wt% to 30 wt%, the dye represented by the formula (2) is 40 wt% to 60 wt%, and the dye represented by the formula (3) is 20 wt% to 30 wt%. % Content is preferable.
本発明の青色反応染料組成物に含有される遊離酸の形が式（４）で示される染料は特許文献２に、遊離酸の形が式（５）で示される染料は特許文献３、４に、遊離酸の形が式（６）で示される染料は特公平３−１０６６９号公報に記載されている。しかしながら、それらの染料を含有する青色反応染料組成物については知られていない。本発明の青色反応染料組成物に含有される式（４）〜式（６）で示される染料は、該青色反応染料組成物に対して式（４）で示される染料を１０重量％〜９０重量％、式（５）及び式（６）で示される染料からなる群から選ばれる１種以上の染料を１０重量％〜９０重量％含有するのが好ましい。特に式（４）で示される染料を１０重量％〜３０重量％、式（５）及び式（６）で示される染料からなる群から選ばれる１種以上の染料を７０重量％〜９０重量％含有するのが好ましく、式（４）で示される染料を１０重量％〜３０重量％、式（５）で示される染料を５０重量％〜６０重量％及び式（６）で示される染料を２０重量％〜３０重量％含有するのが殊更好ましい。 The dye having the free acid form represented by the formula (4) contained in the blue reactive dye composition of the present invention is disclosed in Patent Document 2, and the dye having the free acid form represented by the formula (5) is disclosed in Patent Documents 3 and 4. In addition, a dye having a free acid form represented by the formula (6) is described in JP-B-3-10669. However, blue reactive dye compositions containing these dyes are not known. The dye represented by Formula (4) to Formula (6) contained in the blue reactive dye composition of the present invention is 10% by weight to 90% by weight of the dye represented by Formula (4) with respect to the blue reactive dye composition. It is preferable to contain 10% by weight to 90% by weight of one or more dyes selected from the group consisting of the dyes represented by weight% and the dyes represented by formula (5) and formula (6). In particular, the dye represented by the formula (4) is 10% by weight to 30% by weight, and one or more dyes selected from the group consisting of the dyes represented by the formulas (5) and (6) are 70% by weight to 90% by weight. It is preferable to contain 10 wt% to 30 wt% of the dye represented by the formula (4), 50 wt% to 60 wt% of the dye represented by the formula (5), and 20 wt% of the dye represented by the formula (6). It is particularly preferred to contain from 30% to 30% by weight.
本発明には式（５）で示される染料とＣ．Ｉ．Ｒｅａｃｔｉｖｅ Ｂｌａｃｋ ５として知られる式（７）で示される染料を含有する紺色反応染料組成物も含まれる。本発明の紺色反応染料組成物に含有される式（５）及び式（７）で示される染料は、該紺色反応染料組成物に対して式（５）で示される染料を５重量％〜９５重量％、式（７）で示される染料を５重量％〜９５重量％含有するのが好ましく、式（５）で示される染料を８０重量％〜９５重量％、式（７）で示される染料を５重量％〜２０重量％含有するのが特に好ましい。 In the present invention, the dye represented by the formula (5) and C.I. I. Also included is an amber reactive dye composition containing a dye of formula (7) known as Reactive Black 5. The dye represented by the formula (5) and the formula (7) contained in the amber reactive dye composition of the present invention is 5% to 95% by weight of the dye represented by the formula (5) with respect to the amber reactive dye composition. It is preferable to contain 5% by weight to 95% by weight of the dye represented by the formula (7), 80% to 95% by weight of the dye represented by the formula (5), and the dye represented by the formula (7). It is particularly preferable to contain 5 to 20% by weight.
本発明の反応染料組成物に含有される式（８）で示される黄色反応染料は特許文献６等に記載されている。 The yellow reactive dye represented by the formula (8) contained in the reactive dye composition of the present invention is described in Patent Document 6 and the like.
本発明の反応染料組成物に含有される式（１）〜式（８）で示される染料においてＹ１、Ｙ２、Ｙ３、Ｙ４、Ｙ５、Ｙ６、Ｙ７、Ｙ８はそれぞれ独立にＳＯ２ＣＨ＝ＣＨ２又はＳＯ２ＣＨ２ＣＨ２Ｚであり、Ｚはアルカリで脱離する基である。Ｚがアルカリで脱離するとＳＯ２ＣＨ＝ＣＨ２となる。Ｚとしては脱離基として知られる各種の基が使用可能であるが、例えば、ＯＳＯ３Ｈ等のスルホン酸基が挙げられ、中でもＯＳＯ３Ｈが好ましい。
式（７）で示される染料において両Ｙ７は同一であっても異なっていてもよい。
式（４）で示される染料においてＹ９はＳＯ２ＣＨ２ＣＨ２ＯＳＯ３Ｈ又はＳＯ２ＣＨ＝ＣＨ２であり、Ｒ１は水素原子、ハロゲン原子、又は（Ｃ１〜Ｃ４）アルコキシ基である。該ハロゲン原子としては、例えば、塩素原子、臭素原子等が挙げられ、該（Ｃ１〜Ｃ４）アルコキシ基としては、例えば、メトキシ基、エトキシ基、ｎ−プロポキシ基、イソプロポキシ基、ｎ−ブトキシ基、イソブトキシ基、ｔ−ブトキシ基等が挙げられる。
式（６）で示される染料におけるＲ２は水素原子又は（Ｃ１〜Ｃ４）アルキル基である。該（Ｃ１〜Ｃ４）アルキル基としては、例えば、メチル基、エチル基、ｎ−プロピル基、イソプロピル基、ｎ−ブチル基、イソブチル基、ｔ−ブチル基等が挙げられる。
本発明において置換基の置換位置は特に限定されていない場合、置換可能なすべての位置の置換体を本発明に含む。
Y 1 , Y 2 , Y 3 , Y 4 , Y 5 , Y 6 , Y 7 , Y 8 in the dyes represented by formula (1) to formula (8) contained in the reactive dye composition of the present invention are respectively Independently, SO 2 CH═CH 2 or SO 2 CH 2 CH 2 Z, where Z is a group leaving with an alkali. When Z is eliminated by alkali, SO 2 CH═CH 2 is obtained. As the Z can be used are various groups known as leaving group include, for example, a sulfonic acid group such as OSO 3 H, among them OSO 3 H is preferred.
In the dye represented by formula (7), both Y 7 may be the same or different.
In the dye represented by the formula (4), Y 9 is SO 2 CH 2 CH 2 OSO 3 H or SO 2 CH═CH 2 , and R 1 is a hydrogen atom, a halogen atom, or a (C1-C4) alkoxy group. . Examples of the halogen atom include a chlorine atom and a bromine atom. Examples of the (C1 to C4) alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, and an n-butoxy group. , Isobutoxy group, t-butoxy group and the like.
R 2 in the dye represented by the formula (6) is a hydrogen atom or a (C1-C4) alkyl group. Examples of the (C1 to C4) alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a t-butyl group.
In this invention, when the substitution position of a substituent is not specifically limited, the substituted substance of all the positions which can be substituted is included in this invention.
本発明の反応染料組成物に含有される式（１）〜（８）で示される反応染料は遊離酸の形で示しているが、塩であってもよく、その対カチオンとしては特に限定されない。中でもアルカリ金属塩又はアルカリ土類金属塩が好ましく、特にナトリウム塩、カリウム塩、リチウム塩が好ましい。
本発明の反応染料組成物に含有される各染料は前記のように文献記載の方法又はその方法に準じて製造することも、市場から容易に入手することもできる。
The reactive dyes represented by formulas (1) to (8) contained in the reactive dye composition of the present invention are shown in the form of a free acid, but may be a salt, and the counter cation is not particularly limited. . Of these, alkali metal salts or alkaline earth metal salts are preferable, and sodium salts, potassium salts, and lithium salts are particularly preferable.
Each dye contained in the reactive dye composition of the present invention can be produced according to the method described in the literature as described above, or its method, or can be easily obtained from the market.
本発明には、前記のように式（１）〜式（３）で示される染料を含有する赤色反応染料組成物と、式（４）で示される染料と式（５）及び式（６）で示される染料からなる群から選ばれる１種以上の染料を含有する青色染料組成物を含有する反応染料組成物も含まれる。
本発明には、前記のように式（１）〜式（３）で示される染料を含有する赤色反応染料組成物と、式（５）で示される染料と式（７）で示される染料を含有する紺色反応染料組成物を含有する反応染料組成物も含まれる。
本発明には、式（１）〜式（３）で示される染料を含有する赤色反応染料組成物と、式（８）で示される黄色反応染料を含有する反応染料組成物も含まれる。
In the present invention, as described above, the red reactive dye composition containing the dye represented by the formulas (1) to (3), the dye represented by the formula (4), the formula (5) and the formula (6). A reactive dye composition containing a blue dye composition containing one or more dyes selected from the group consisting of dyes represented by the formula
In the present invention, as described above, the red reactive dye composition containing the dye represented by the formulas (1) to (3), the dye represented by the formula (5), and the dye represented by the formula (7) are provided. A reactive dye composition containing an amber reactive dye composition is also included.
The present invention also includes a red reactive dye composition containing a dye represented by formulas (1) to (3) and a reactive dye composition containing a yellow reactive dye represented by formula (8).
又、本発明には、前記のように式（４）で示される染料と式（５）及び式（６）で示される染料からなる群から選ばれる１種以上の染料を含有する青色染料組成物と、式（８）で示される黄色反応染料を含有する反応染料組成物も含まれる。
本発明には、前記のように式（５）で示される染料と式（７）で示される染料を含有する紺色反応染料と、式（８）で示される黄色反応染料を含有する反応染料組成物も含まれる。
更に、本発明には、前記のように赤色反応染料組成物、青色染料組成物又は紺色反応染料組成物及び黄色反応染料を含有する反応染料組成物も含まれる。
これらの反応染料組成物が本発明の目的を達成していることは後記の実施例からも明らかである。
The present invention also includes a blue dye composition containing at least one dye selected from the group consisting of the dye represented by formula (4) and the dye represented by formula (5) and formula (6) as described above. And a reactive dye composition containing a yellow reactive dye represented by formula (8).
In the present invention, as described above, a reactive dye composition containing the dye represented by formula (5) and the amber reactive dye containing the dye represented by formula (7) and the yellow reactive dye represented by formula (8) Things are also included.
Furthermore, the present invention also includes a reactive dye composition containing a red reactive dye composition, a blue dye composition or an amber reactive dye composition and a yellow reactive dye as described above.
It is clear from the examples described later that these reactive dye compositions achieve the object of the present invention.
本発明の反応染料組成物において各反応染料の配合方法は特に制限されない。例えば、それぞれの反応染料を別々に製造し、その後に配合する方法、製造時生成した各反応染料を含有した反応液を混合し、その後に乾燥して組成物とする方法、更には、染色浴にそれぞれの反応染料を溶解し、染色浴中で各組成物と同じ組成とする方法等を採ることができる。その際に、赤色反応染料組成物、青色反応染料組成物、紺色反応染料組成物、黄色反応染料組成物の混合割合は、所望の色調に応じて適宜配合され、特に制限はない。又、必要に応じて、本発明の組成物中には水や公知の添加剤、例えば、濃度調整剤、分散剤、均染剤、沈殿防止剤、金属イオン封鎖剤、還元防止剤等を含有させてもよい。 The method for blending each reactive dye in the reactive dye composition of the present invention is not particularly limited. For example, a method in which each reactive dye is produced separately and then blended, a reaction solution containing each reactive dye produced at the time of production is mixed and then dried to form a composition, and further a dyeing bath Each reactive dye can be dissolved in and the same composition as each composition in a dyeing bath can be employed. At that time, the mixing ratio of the red reactive dye composition, the blue reactive dye composition, the amber reactive dye composition, and the yellow reactive dye composition is appropriately blended according to the desired color tone and is not particularly limited. Further, if necessary, the composition of the present invention contains water and known additives such as a concentration adjusting agent, a dispersing agent, a leveling agent, a suspending agent, a sequestering agent, and a reducing agent. You may let them.
染浴、パディング浴、捺染糊に本発明の反応染料組成物を構成する各染料及び必要に応じて前記の添加剤等を加えて染色する場合に、各染料、添加剤等を溶解する順序は任意の順序でよい。使用する各構成成分の使用量も公知の方法を参考にして決めればよい。 In the dyeing bath, padding bath, printing paste, each dye constituting the reactive dye composition of the present invention and, if necessary, adding the above-mentioned additives as necessary, the order of dissolving the respective dyes, additives, etc. Any order is acceptable. What is necessary is just to determine the usage-amount of each structural component to be used with reference to a well-known method.
本発明の反応染料組成物を用いた染色法においてそれらの使用量は通常、繊維重量に対して０．０００５重量％〜１５重量％程度である。 In the dyeing method using the reactive dye composition of the present invention, the amount used is usually about 0.0005 wt% to 15 wt% with respect to the fiber weight.
本発明の反応染料組成物はセルロース繊維及びそれを含有する繊維に有用である。対象となる繊維としては、例えば、木綿、麻、レーヨン、ポリノジック、キュプラ、リヨセル等のセルロース繊維、又は、これら同士の混合繊維が挙げられる。更にはこれらの繊維又は混合繊維と他の繊維、例えば、ポリエステル繊維、アセテート繊維、ポリアクリルニトリル繊維、羊毛、絹、ナイロン等のポリアミド繊維等との混紡、又は、交織品等を挙げることができる。 The reactive dye composition of the present invention is useful for cellulose fibers and fibers containing them. Examples of the target fiber include cellulose fibers such as cotton, hemp, rayon, polynosic, cupra, and lyocell, or mixed fibers of these. Furthermore, these fibers or mixed fibers and other fibers, for example, polyester fibers, acetate fibers, polyacrylonitrile fibers, blends of wool, silk, nylon and other polyamide fibers, or woven products can be mentioned. .
本発明において、染色法は、例えば、それ自体は公知の後記のような方法に従って行うことができるが、これらに限定されるものではない。例えば、木綿等のセルロース繊維の染色においては所望の色相及び濃度に応じた本発明の反応染料組成物を染浴に加え、無機中性塩、例えば、無水芒硝、食塩等と、酸結合剤、例えば、炭酸ナトリウム、重炭酸ナトリウム、苛性ソーダ、第三燐酸ナトリウム等をそれぞれ単独に、又は、併用して行う。この時用いる無機中性塩や酸結合剤の使用量についても特に制限はない。又、無機中性塩や酸結合剤の染浴への投入は一度に行ってもよいし、分割して投入してもよい。又、その他、浴中柔軟剤、均染剤等の公知の染色助剤を併用してもよいが、染色助剤としては特にこれらに限定されるものではない。染色温度は４０〜９０℃、好ましくは５０〜７０℃である。 In the present invention, the staining method can be carried out according to, for example, a method described below which is known per se, but is not limited thereto. For example, in dyeing cellulose fibers such as cotton, the reactive dye composition of the present invention according to the desired hue and concentration is added to the dyeing bath, and an inorganic neutral salt such as anhydrous sodium sulfate, sodium chloride, an acid binder, For example, sodium carbonate, sodium bicarbonate, caustic soda, sodium triphosphate and the like are used alone or in combination. There are no particular restrictions on the amount of inorganic neutral salt or acid binder used at this time. In addition, the inorganic neutral salt or the acid binder may be added to the dye bath at once or dividedly. In addition, known dyeing aids such as bath softeners and leveling agents may be used in combination, but the dyeing aids are not particularly limited thereto. The dyeing temperature is 40 to 90 ° C, preferably 50 to 70 ° C.
連続染色法である酸結合剤、例えば、炭酸ナトリウム、重炭酸ナトリウム、苛性ソーダ等を単独に、又は、併用して染料パディング液に加え、公知の方法に準じてパディング後、乾燥し、次いで公知の方法に準じて乾熱又は蒸熱することにより染色する一浴パディング法、あるいは、染料をパディングした後、乾燥し、次いで公知の無機中性塩、例えば、無水芒硝、食塩等と、酸結合剤、例えば、苛性ソーダ、珪酸ナトリウム等をパディングし、公知の方法に準じて乾熱又は蒸熱により染色する二浴パディング法を行ってもよいが、連続染色法としてはこれらに限定されない。 Acid binders that are continuous dyeing methods, such as sodium carbonate, sodium bicarbonate, caustic soda, etc., alone or in combination, are added to the dye padding solution, padded according to known methods, dried, then known One bath padding method for dyeing by dry heat or steaming according to the method, or drying after padding the dye, then known inorganic neutral salt, such as anhydrous sodium sulfate, sodium chloride, and acid binder, For example, a two-bath padding method in which caustic soda, sodium silicate or the like is padded and dyed by dry heat or steam according to a known method may be performed, but the continuous dyeing method is not limited thereto.
捺染方法としては、アルギン酸ナトリウム、エマルジョン糊等を元糊とし、反応染料組成物と、重炭酸ナトリウム等の酸結合剤を含む捺染糊を公知の方法に準じて印捺後、公知の方法に準じて乾熱又は蒸熱することにより行う方法が挙げられる。染色工程終了後、水洗、湯染の後、常法により、市販のソーピング剤を含むソーピング浴にて洗浄を行い染色を終了する。 As a printing method, based on sodium alginate, emulsion paste, etc., printing a paste containing a reactive dye composition and an acid binder such as sodium bicarbonate in accordance with a known method, and in accordance with a known method The method of performing by carrying out dry heat or steaming is mentioned. After completion of the dyeing process, washing with water and hot water dyeing are followed by washing in a soaping bath containing a commercially available soaping agent by a conventional method to complete dyeing.
以下、本発明を実施例により更に詳細に説明する。尚、本文中「部」は特別な記載がない限り重量部を表す。表中、Ｃ．Ｉ．Ｒｅａｃｔｉｖｅはカラーインデックスジェネリックネームを意味する。
実施例中、式（１）の染料におけるＹ１はパラ位のＳＯ２ＣＨ２ＣＨ２ＯＳＯ３Ｎａであり、式（２）の染料におけるＹ２はパラ位のＳＯ２ＣＨ２ＣＨ２ＯＳＯ３Ｎａであり、式（３）の染料におけるＹ３はＳＯ２ＣＨ２ＣＨ２ＯＳＯ３Ｎａ、Ｙ４はパラ位のＳＯ２ＣＨ２ＣＨ２ＯＳＯ３Ｎａであり、式（４）の染料は下記の通りであり、式（５）の染料におけるＹ５はパラ位のＳＯ２ＣＨ２ＣＨ２ＯＳＯ３Ｎａであり、式（６）の染料におけるＲ２はエチル基、Ｙ６はパラ位のＳＯ２ＣＨ２ＣＨ２ＯＳＯ３Ｎａであり、Ｙ４はパラ位のＳＯ２ＣＨ２ＣＨ２ＯＳＯ３Ｎａであり、式（７）の染料におけるＹ７はＳＯ２ＣＨ２ＣＨ２ＯＳＯ３Ｎａであり、式（８）の染料におけるＹ８はパラ位のＳＯ２ＣＨ２ＣＨ２ＯＳＯ３Ｎａである。
Hereinafter, the present invention will be described in more detail with reference to examples. In the text, “parts” represents parts by weight unless otherwise specified. In the table, C.I. I. Reactive means a color index generic name.
In the examples, Y 1 in the dye of formula (1) is the para position of the SO 2 CH 2 CH 2 OSO 3 Na, SO 2 CH 2 CH 2 OSO 3 of Y 2 is the para position in the dye of formula (2) Y 3 in the dye of formula (3) is SO 2 CH 2 CH 2 OSO 3 Na, Y 4 is para-position SO 2 CH 2 CH 2 OSO 3 Na, and the dye of formula (4) is Y 5 in the dye of formula (5) is SO 2 CH 2 CH 2 OSO 3 Na in the formula (5), R 2 in the dye of formula (6) is an ethyl group, and Y 6 is SO in the para position. 2 CH 2 CH 2 OSO 3 Na, Y 4 is para-position SO 2 CH 2 CH 2 OSO 3 Na, Y 7 in the dye of formula (7) is SO 2 CH 2 CH 2 OSO 3 Na, Y in the dye of formula (8) 8 of the para position A O 2 CH 2 CH 2 OSO 3 Na.
実施例１
反応染料の配合組成
表１に反応染料の配合組成を記した。
［表１］配合組成
Example 1
Composition of reactive dyes Table 1 shows the composition of reactive dyes.
[Table 1] Composition
本発明配合例１ Ｂｒｏｗｎ
赤色反応染料
式（１）の染料 ０．１０部
式（２）の染料 ０．１８部
式（３）の染料 ０．１０部
青色反応染料
式（４）の染料 ０．２７部
式（５）の染料 ０．１０部
式（６）の染料 ０．１４部
黄色反応染料
式（８）の染料 １．２６部
Invention Formulation Example 1 Brown
Red reactive dye
0.10 parts of the dye of formula (1)
0.18 parts of the dye of formula (2)
0.10 parts of dye of formula (3)
Blue reactive dye
0.27 parts of dye of formula (4)
Dye of formula (5) 0.10 parts
0.14 parts of dye of formula (6)
Yellow reactive dye
Dye of formula (8) 1.26 parts
本発明配合例２ Ｂｒｏｗｎ
赤色反応染料
式（１）の染料 ０．１２部
式（２）の染料 ０．１４部
式（３）の染料 ０．０８部
紺色反応染料
式（５）の染料 ０．３７部
式（７）の染料 ０．０４部
黄色反応染料
式（８）の染料 １．１４部
Invention Formulation Example 2 Brown
Red reactive dye
0.12 parts of dye of formula (1)
0.14 parts of the dye of formula (2)
0.08 parts of dye of formula (3)
Amber reactive dye
0.37 parts of dye of formula (5)
0.04 parts of dye of formula (7)
Yellow reactive dye
Dye of formula (8) 1.14 parts
本発明配合例３ Ｇｒｅｙ
赤色反応染料
式（１）の染料 ０．１２部
式（２）の染料 ０．２０部
式（３）の染料 ０．１１部
青色反応染料
式（４）の染料 ０．２６部
式（５）の染料 ０．７１部
式（６）の染料 ０．３５部
黄色反応染料
式（８）の染料 ０．７５部
Invention Formulation Example 3 Gray
Red reactive dye
0.12 parts of dye of formula (1)
0.20 parts of dye of formula (2)
0.11 part of dye of formula (3)
Blue reactive dye
0.26 parts of dye of formula (4)
0.71 part of dye of formula (5)
0.35 parts of dye of formula (6)
Yellow reactive dye
0.75 parts of dye of formula (8)
本発明配合例４ Ｇｒｅｙ
赤色反応染料
式（１）の染料 ０．０９部
式（２）の染料 ０．１８部
式（３）の染料 ０．０９部
紺色反応染料
式（５）の染料 ０．９３部
式（７）の染料 ０．１１部
黄色反応染料
式（８）の染料 ０．６０部
Invention Formulation Example 4 Gray
Red reactive dye
0.09 parts of dye of formula (1)
0.18 parts of the dye of formula (2)
Dye of formula (3) 0.09 part
Amber reactive dye
0.93 parts of dye of formula (5)
Dye of formula (7) 0.11 part
Yellow reactive dye
0.60 parts of the dye of formula (8)
比較配合例１ Ｂｒｏｗｎ
赤色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｒｅｄ １９５ ０．５０部
青色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｂｌｕｅ ２２２ ０．４０部
黄色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｙｅｌｌｏｗ １４５ １．２１部
Comparative Formulation Example 1 Brown
Red reactive dye C.I. I. Reactive Red 195 0.50 part
Blue reactive dye C.I. I. Reactive Blue 222 0.40 parts
Yellow reactive dye C.I. I. Reactive Yellow 145 1.21 parts
比較配合例２ Ｇｒｅｙ
赤色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｒｅｄ １９５ ０．５０部
青色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｂｌｕｅ ５ ０．７０部
黄色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｙｅｌｌｏｗ １４５ ０．６４部
Comparative Formulation Example 2 Gray
Red reactive dye C.I. I. Reactive Red 195 0.50 part
Blue reactive dye C.I. I. Reactive Blue 5 0.70 parts
Yellow reactive dye C.I. I. Reactive Yellow 145 0.64 parts
試験法について説明する。
浴比依存性試験
（１）浴比１：１０での染色
表１に示す各配合組成の染料及び無水硫酸ナトリウム１０部に水を加えて全量４９０部の染浴を調製した。この染浴に木綿メリヤス５０部を投入し、６０℃で１５分間処理後、炭酸ナトリウム１０部を投入し、同温度で６０分間染色した。次いで、水洗、湯洗の後、市販のソーピング剤（スコアロールＣ−１２００ 北広ケミカル（株）１ｇ／Ｌ）を含む水溶液１０００部中で１００℃にて１５分間のソーピングをし、次いで水洗、乾燥して染色物を得た。
The test method will be described.
Bath ratio dependency test (1) Dyeing at a bath ratio of 1:10 A dye bath having a total amount of 490 parts was prepared by adding water to 10 parts of the dyes of each formulation shown in Table 1 and anhydrous sodium sulfate. 50 parts of cotton knitted fabric was added to this dye bath, treated at 60 ° C. for 15 minutes, then 10 parts of sodium carbonate was added, and dyed at the same temperature for 60 minutes. Next, after washing with water and hot water, soaping is performed at 100 ° C. for 15 minutes in 1000 parts of an aqueous solution containing a commercially available soaping agent (Scorerol C-1200 Kitahiro Chemical Co., Ltd. 1 g / L), then washed with water and dried. As a result, a dyed product was obtained.
（２）浴比１：３０での染色
表１に示す各配合組成の染料及び無水硫酸ナトリウム３０部に水を加えて全量１４７０部の染浴を調製した。この染浴に木綿メリヤス５０部を投入し、６０℃で１５分間処理後、炭酸ナトリウム３０部を投入し、同温度で６０分間染色した。次いで、水洗、湯洗の後、市販のソーピング剤（スコアロールＣ−１２００ 北広ケミカル（株）１ｇ／Ｌ）を含む水溶液１０００部中で１００℃にて１５分間のソーピングをし、次いで水洗、乾燥して染色物を得た。
(2) Dyeing at a bath ratio of 1:30 A dye bath having a total amount of 1470 parts was prepared by adding water to the dyes of each formulation shown in Table 1 and 30 parts of anhydrous sodium sulfate. 50 parts of cotton knitted fabric was added to this dye bath, treated at 60 ° C. for 15 minutes, then 30 parts of sodium carbonate was added, and dyed at the same temperature for 60 minutes. Next, after washing with water and hot water, soaping is performed at 100 ° C. for 15 minutes in 1000 parts of an aqueous solution containing a commercially available soaping agent (Scorerol C-1200 Kitahiro Chemical Co., Ltd. 1 g / L), then washed with water and dried. As a result, a dyed product was obtained.
（３）浴比１：６０での染色
表１に示す各配合組成の染料及び無水硫酸ナトリウム６０部に水を加えて全量２９４０部の染浴を調製した。この染浴に木綿メリヤス５０部を投入し、６０℃で１５分間処理後、炭酸ナトリウム６０部を投入し、同温度で６０分間染色した。次いで、水洗、湯洗の後、前記ソーピング剤を含む水溶液１０００部中で１００℃にて１５分間のソーピングをし、次いで水洗、乾燥して染色物を得た。
(3) Dyeing at a bath ratio of 1:60 A dye bath having a total amount of 2940 parts was prepared by adding water to 60 parts of the dyes of each composition shown in Table 1 and anhydrous sodium sulfate. 50 parts of cotton knitted fabric was put into this dye bath, treated at 60 ° C. for 15 minutes, and then 60 parts of sodium carbonate was added and dyed at that temperature for 60 minutes. Then, after washing with water and hot water, soaping was performed at 1000 ° C. for 15 minutes in 1000 parts of an aqueous solution containing the soaping agent, and then washed with water and dried to obtain a dyed product.
（４）浴比１：６０で濃度補正した染色
（３）の浴比１：６０の条件で表１に示す各配合組成の染料を１．３３倍使用して染色し染色物を得た。
(4) Dyeing Corrected at a Density Ratio of 1:60 Bath Ratio Dyeing was carried out by using 1.33 times the dye composition shown in Table 1 under the condition of (3) bath ratio 1:60 to obtain a dyed product.
（５）判定方法
（１）の浴比１：１０で得られた染色物を基準にそれぞれの条件で得られた染色物の色相差を、測色機カラ−アイＣＥ７１００（マクベス社製）、Ｄ６５光源下、Ｃ．Ｉ．Ｅ色差式を使用して求め、色相差ΔＥａ＊ｂ＊及び色差ΔＥを表２に示した。
(5) Judgment method The color difference of the dyed product obtained under each condition on the basis of the dyed product obtained at a bath ratio of 1:10 in (1) is measured by a colorimeter Color Eye CE7100 (manufactured by Macbeth), Under the D65 light source, C.I. I. Table 2 shows the hue difference ΔEa * b * and the color difference ΔE obtained using the E color difference formula.
［表２］
実施例２
反応染料の配合組成
表３に反応染料の配合組成を記した。
［表３］
Example 2
Composition of reactive dyes Table 3 shows the composition of reactive dyes.
[Table 3]
本発明配合例５ Ｂｒｏｗｎ
赤色反応染料
式（１）の染料 ０．２９部
式（２）の染料 ０．５６部
式（３）の染料 ０．２９部
青色反応染料
式（４）の染料 ０．３１部
式（５）の染料 ０．８３部
式（６）の染料 ０．３９部
黄色反応染料
式（８）の染料 ３．７８部
Invention Formulation Example 5 Brown
Red reactive dye
0.29 parts of dye of formula (1)
0.56 parts of dye of formula (2)
0.29 parts of the dye of formula (3)
Blue reactive dye
0.31 part of dye of formula (4)
0.83 parts of dye of formula (5)
0.39 parts of dye of formula (6)
Yellow reactive dye
3.78 parts of dye of formula (8)
本発明配合例６ Ｂｒｏｗｎ
赤色反応染料
式（１）の染料 ０．２６部
式（２）の染料 ０．４９部
式（３）の染料 ０．２７部
紺色反応染料
式（５）の染料 １．１０部
式（７）の染料 ０．１３部
黄色反応染料
式（８）の染料 ３．４２部
Invention Formulation Example 6 Brown
Red reactive dye
0.26 parts of dye of formula (1)
0.49 parts of dye of formula (2)
0.27 parts of dye of formula (3)
Amber reactive dye
Dye of formula (5) 1.10 parts
0.13 parts of dye of formula (7)
Yellow reactive dye
3.42 parts of dye of formula (8)
本発明配合例７ Ｇｒｅｙ
赤色反応染料
式（１）の染料 ０．３２部
式（２）の染料 ０．６３部
式（３）の染料 ０．３４部
青色反応染料
式（４）の染料 ０．７９部
式（５）の染料 ２．１４部
式（６）の染料 １．０３部
黄色反応染料
式（８）の染料 ２．２５部
Invention Formulation Example 7 Gray
Red reactive dye
0.32 parts of dye of formula (1)
0.63 parts of dye of formula (2)
0.34 parts of dye of formula (3)
Blue reactive dye
0.79 parts of dye of formula (4)
2.14 parts of dye of formula (5)
1.03 parts of dye of formula (6)
Yellow reactive dye
2.25 parts of dye of formula (8)
本発明配合例８ Ｇｒｅｙ
赤色反応染料
式（１）の染料 ０．２７部
式（２）の染料 ０．５３部
式（３）の染料 ０．２８部
紺色反応染料
式（５）の染料 ２．８０部
式（７）の染料 ０．３２部
黄色反応染料
式（８）の染料 １．８０部
Invention Formulation Example 8 Gray
Red reactive dye
0.27 parts of dye of formula (1)
0.53 parts of dye of formula (2)
0.28 parts of dye of formula (3)
Amber reactive dye
2.80 parts of dye of formula (5)
0.32 parts of dye of formula (7)
Yellow reactive dye
Dye of formula (8) 1.80 parts
比較配合例３ Ｂｒｏｗｎ
赤色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｒｅｄ １９５ １．５０部
青色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｂｌｕｅ ２２２ １．２０部
黄色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｙｅｌｌｏｗ １４５ ３．６３部
Comparative Blending Example 3 Brown
Red reactive dye C.I. I. Reactive Red 195 1.50 parts
Blue reactive dye C.I. I. Reactive Blue 222 1.20 parts
Yellow reactive dye C.I. I. Reactive Yellow 145 3.63 parts
比較配合例４ Ｂｒｏｗｎ
赤色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｒｅｄ １９５ １．４４部
赤色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｂｌｕｅ ５ ０．８４部
赤色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｙｅｌｌｏｗ １４５ ３．９０部
Comparative Formulation Example 4 Brown
Red reactive dye C.I. I. Reactive Red 195 1.44 parts
Red reactive dye C.I. I. Reactive Blue 5 0.84 parts
Red reactive dye C.I. I. Reactive Yellow 145 3.90 parts
比較配合例５ Ｇｒｅｙ
赤色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｒｅｄ １９５ １．８９部
青色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｂｌｕｅ ２２２ ３．０５部
黄色反応染料
Ｃ．Ｉ．Ｒｅａｃｔｉｖｅ Ｙｅｌｌｏｗ １４５ １．８３部
Comparative Formulation Example 5 Gray
Red reactive dye C.I. I. Reactive Red 195 1.89 parts
Blue reactive dye C.I. I. Reactive Blue 222 3.05 parts
Yellow reactive dye C.I. I. Reactive Yellow 145 1.83 parts
アルカリ添加温度依存性試験
（１）アルカリ（炭酸ナトリウム） ６０℃添加での染色
表３に示す各配合組成の染料及び無水硫酸ナトリウム４０部に水を加えて全量４９０部の染浴を調製した。この染浴に木綿メリヤス５０部を投入し、２０分間で６０℃へ昇温した。６０℃で１０分間処理後、炭酸ナトリウム１０部を投入し、同温度で６０分間染色した。次いで、水洗、湯洗の後、市販のソーピング剤（スコアロールＣ−１２００ 北広ケミカル（株）１ｇ／Ｌ）を含む水溶液１０００部中で１００℃にて１５分間のソーピングをし、次いで水洗、乾燥して染色物を得た。
Alkali addition temperature dependency test (1) Alkali (sodium carbonate) Dyeing at 60 ° C. Addition of water to 40 parts of the dyes and the anhydrous sodium sulfate shown in Table 3 to prepare a dye bath having a total amount of 490 parts. 50 parts of cotton knitted fabric was added to this dye bath, and the temperature was raised to 60 ° C. in 20 minutes. After treatment at 60 ° C. for 10 minutes, 10 parts of sodium carbonate was added and dyed at the same temperature for 60 minutes. Next, after washing with water and hot water, soaping is performed at 100 ° C. for 15 minutes in 1000 parts of an aqueous solution containing a commercially available soaping agent (Scorerol C-1200 Kitahiro Chemical Co., Ltd. 1 g / L), then washed with water and dried. As a result, a dyed product was obtained.
（２）アルカリ（炭酸ナトリウム） ４０℃添加での染色
表３に示す各配合組成の染料及び無水硫酸ナトリウム４０部に水を加えて全量４９０部の染浴を調製した。この染浴に木綿メリヤス５０部を投入し、４０℃で２０分間処理後、炭酸ナトリウム１０部を投入し、２０分間で６０℃へ昇温した。同温度で６０分間染色し、次いで、水洗、湯洗の後、市販のソーピング剤（スコアロールＣ−１２００ 北広ケミカル（株）１ｇ／Ｌ）を含む水溶液１０００部中で１００℃にて１５分間のソーピングをし、次いで水洗、乾燥して染色物を得た。
(2) Dyeing by adding alkali (sodium carbonate) at 40 ° C. Dye baths having a total amount of 490 parts were prepared by adding water to 40 parts of the dyes having the blending compositions shown in Table 3 and anhydrous sodium sulfate. 50 parts of cotton knitted fabric was added to this dye bath, treated at 40 ° C. for 20 minutes, 10 parts of sodium carbonate was added, and the temperature was raised to 60 ° C. over 20 minutes. Dyeing at the same temperature for 60 minutes, followed by washing with water and washing with hot water, followed by 15 minutes at 100 ° C. in 1000 parts of an aqueous solution containing a commercially available soaping agent (Scorerol C-1200 Kitahiro Chemical Co., Ltd. 1 g / L) It was soaped, then washed with water and dried to obtain a dyed product.
（３）判定方法
６０℃添加で得られた染色物を基準に、４０℃添加で得られた染色物の色相差を、測色機カラ−アイＣＥ７１００（マクベス社製）、Ｄ６５光源下、Ｃ．Ｉ．Ｅ色差式を使用して求め、色差ΔＥを表４に示した。
(3) Judgment method Based on the dyed product obtained by adding 60 ° C, the hue difference of the dyed product obtained by adding 40 ° C was measured using a colorimeter Color Eye CE7100 (manufactured by Macbeth), under the D65 light source, C . I. The color difference ΔE was determined using the E color difference formula and is shown in Table 4.
［表４］
表２及び表４から明らかなように、本発明の配合例１、２、３、４、５、６、７、８の組み合わせで染色を行った場合、赤色反応染料、青色反応染料、紺色反応染料及び黄色反応染料の親和性が一致しており、浴比が大きく変動した場合でも濃度補正をしても色相変化が極めて小さく、又、アルカリ添加温度が変動した場合でも色相変化が極めて小さく、染色再現性が極めて優れている。 As is apparent from Tables 2 and 4, when dyeing is performed with a combination of Formulation Examples 1, 2, 3, 4, 5, 6, 7, and 8 of the present invention, a red reactive dye, a blue reactive dye, and an amber reaction The affinity of the dye and the yellow reactive dye are the same, and even when the bath ratio fluctuates greatly or even when the concentration is corrected, the hue change is extremely small, and even when the alkali addition temperature varies, the hue change is extremely small. Dyeing reproducibility is extremely excellent.
実施例３〜実施例１２
実施例１の配合例１の組み合わせ及び使用量に替えて、表５に示す染料の組み合わせ及び使用量を用い、無水硫酸ナトリウム１５部に水を加えて全量４９０部の染浴をそれぞれ調製した。この染浴に木綿メリヤス５０部を投入し、２０分間で６０℃へ昇温した。６０℃で１０分間処理後、炭酸ナトリウム１０部を投入し、同温度で６０分間染色した。次いで、水洗、湯洗の後、市販のソーピング剤（スコアロールＣ−１２００ 北広ケミカル（株）１ｇ／Ｌ）を含む水溶液５００部中で１００℃にて１５分間のソーピングをし、次いで水洗、乾燥して染色物を得た。
［表５］ 配合組成
Examples 3 to 12
In place of the combination and usage amount of Formulation Example 1 of Example 1, water was added to 15 parts of anhydrous sodium sulfate using the dye combinations and usage amounts shown in Table 5 to prepare a total amount of 490 parts of dye bath. 50 parts of cotton knitted fabric was added to this dye bath, and the temperature was raised to 60 ° C. in 20 minutes. After treatment at 60 ° C. for 10 minutes, 10 parts of sodium carbonate was added and dyed at the same temperature for 60 minutes. Next, after washing with water and hot water, soaping is performed for 15 minutes at 100 ° C. in 500 parts of an aqueous solution containing a commercially available soaping agent (Scorerol C-1200 Kitahiro Chemical Co., Ltd. 1 g / L), followed by washing with water and drying. As a result, a dyed product was obtained.
[Table 5] Composition
実施例３ グリーン
赤色反応染料
式（１）の染料 ０．０５部
式（２）の染料 ０．１０部
式（３）の染料 ０．０５部
青色反応染料
式（４）の染料 ０．１６部
式（６）の染料 ０．６４部
黄色反応染料
式（８）の染料 ０．８０部
Example 3 Green
Red reactive dye
0.05 parts of dye of formula (1)
0.10 parts of dye of formula (2)
0.05 parts of dye of formula (3)
Blue reactive dye
0.16 parts of dye of formula (4)
0.64 parts of dye of formula (6)
Yellow reactive dye
0.80 parts of dye of formula (8)
実施例４ バイオレット
赤色反応染料
式（１）の染料 ０．２０部
式（２）の染料 ０．３９部
式（３）の染料 ０．２１部
青色反応染料
式（４）の染料 ０．２０部
式（５）の染料 ０．６０部
黄色反応染料
式（８）の染料 ０．２０部
Example 4 Violet
Red reactive dye
0.20 parts of dye of formula (1)
0.39 parts of dye of formula (2)
0.21 parts of dye of formula (3)
Blue reactive dye
0.20 parts of dye of formula (4)
0.60 parts of the dye of formula (5)
Yellow reactive dye
Dye of formula (8) 0.20 part
実施例５ エンジ
赤色反応染料
式（１）の染料 ０．３０部
式（２）の染料 ０．６１部
式（３）の染料 ０．２９部
青色反応染料
式（４）の染料 ０．０４部
式（５）の染料 ０．１０部
式（６）の染料 ０．０６部
黄色反応染料
式（８）の染料 ０．３２部
Example 5
Red reactive dye
0.30 parts of dye of formula (1)
0.61 part of dye of formula (2)
0.29 parts of the dye of formula (3)
Blue reactive dye
Dye of formula (4) 0.04 part
Dye of formula (5) 0.10 parts
Dye of formula (6) 0.06 part
Yellow reactive dye
0.32 parts of dye of formula (8)
実施例６ カーキ
赤色反応染料
式（１）の染料 ０．０７部
式（２）の染料 ０．１５部
式（３）の染料 ０．０８部
青色反応染料
式（４）の染料 ０．０６部
式（５）の染料 ０．２４部
黄色反応染料
式（８）の染料 ０．０９部
Example 6 Khaki
Red reactive dye
0.07 parts of dye of formula (1)
0.15 parts of dye of formula (2)
0.08 parts of dye of formula (3)
Blue reactive dye
Dye of formula (4) 0.06 part
0.24 parts of dye of formula (5)
Yellow reactive dye
Dye of formula (8) 0.09 part
実施例７ ネービー
赤色反応染料
式（１）の染料 ０．２０部
式（２）の染料 ０．４０部
式（３）の染料 ０．２２部
青色反応染料
式（４）の染料 ０．６０部
式（６）の染料 １．８０部
黄色反応染料
式（８）の染料 ０．８０部
Example 7 Navy
Red reactive dye
0.20 parts of dye of formula (1)
Dye of formula (2) 0.40 part
0.22 parts of dye of formula (3)
Blue reactive dye
0.60 parts of dye of formula (4)
Dye of formula (6) 1.80 parts
Yellow reactive dye
0.80 parts of dye of formula (8)
実施例８ グリーン
赤色反応染料
式（１）の染料 ０．０４部
式（２）の染料 ０．０８部
式（３）の染料 ０．０４部
紺色反応染料
式（５）の染料 ０．７０部
式（７）の染料 ０．１０部
黄色反応染料
式（８）の染料 ０．８０部
Example 8 Green
Red reactive dye
0.04 parts of dye of formula (1)
0.08 parts of dye of formula (2)
Dye of formula (3) 0.04 part
Amber reactive dye
0.70 parts of dye of formula (5)
0.10 parts of dye of formula (7)
Yellow reactive dye
0.80 parts of dye of formula (8)
実施例９ バイオレット
赤色反応染料
式（１）の染料 ０．１５部
式（２）の染料 ０．３０部
式（３）の染料 ０．１５部
紺色反応染料
式（５）の染料 ０．５２部
式（７）の染料 ０．０８部
黄色反応染料
式（８）の染料 ０．２０部
Example 9 Violet
Red reactive dye
0.15 parts of dye of formula (1)
0.30 parts of dye of formula (2)
0.15 parts of dye of formula (3)
Amber reactive dye
0.52 parts of dye of formula (5)
Dye of formula (7) 0.08 part
Yellow reactive dye
Dye of formula (8) 0.20 part
実施例１０ エンジ
赤色反応染料
式（１）の染料 ０．２６部
式（２）の染料 ０．５９部
式（３）の染料 ０．１９部
紺色反応染料
式（５）の染料 ０．１０５部
式（７）の染料 ０．０１５部
黄色反応染料
式（８）の染料 ０．３０部
Example 10
Red reactive dye
0.26 parts of dye of formula (1)
0.59 parts of dye of formula (2)
0.19 parts of the dye of formula (3)
Amber reactive dye
0.105 parts of the dye of formula (5)
0.015 parts of dye of formula (7)
Yellow reactive dye
Dye of formula (8) 0.30 part
実施例１１ カーキ
赤色反応染料
式（１）の染料 ０．０７部
式（２）の染料 ０．１１部
式（３）の染料 ０．０８部
紺色反応染料
式（５）の染料 ０．１７部
式（７）の染料 ０．０３部
黄色反応染料
式（８）の染料 ０．９０部
Example 11 Khaki
Red reactive dye
0.07 parts of dye of formula (1)
Dye of formula (2) 0.11 part
0.08 parts of dye of formula (3)
Amber reactive dye
0.17 parts of dye of formula (5)
0.03 part dye of formula (7)
Yellow reactive dye
0.90 parts of dye of formula (8)
実施例１２ ネービー
赤色反応染料
式（１）の染料 ０．１６部
式（２）の染料 ０．３３部
式（３）の染料 ０．１８部
紺色反応染料
式（４）の染料 １．７５部
式（６）の染料 ０．２０部
黄色反応染料
式（８）の染料 ０．６５部
Example 12 Navy
Red reactive dye
0.16 parts of dye of formula (1)
0.33 parts of dye of formula (2)
0.18 parts of the dye of formula (3)
Amber reactive dye
1.75 parts of the dye of formula (4)
Dye of formula (6) 0.20 part
Yellow reactive dye
0.65 parts of the dye of formula (8)
試験結果
実施例３〜１２で得られた染色物について前記と同様に浴比依存性試験及びアルカリ添加温度依存性試験を行ったところ、いずれの反応染料の組み合わせにおいても浴比が大きく変動した場合でも色相変化が極めて小さく、又、アルカリ添加温度が変動した場合でも色相変化が極めて小さく、染色再現性が極めて優れていた。
Test results When the bath ratio dependency test and the alkali addition temperature dependency test were performed in the same manner as described above for the dyed products obtained in Examples 3 to 12, the bath ratio greatly varied in any combination of reactive dyes. However, the hue change was extremely small, and even when the alkali addition temperature fluctuated, the hue change was extremely small and the dyeing reproducibility was extremely excellent.
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| CN102358803B (en) * | 2011-08-25 | 2013-09-11 | 浙江亿得化工有限公司 | Composite black active dye |
| CN104402781B (en) * | 2014-12-11 | 2016-06-29 | 吴江桃源染料有限公司 | A kind of half-finished preparation method of active soil yellow dye |
| CN111032790B (en) * | 2017-09-01 | 2021-11-23 | 日本化药株式会社 | Reactive dye composition and dyeing method using same |
| KR101960807B1 (en) * | 2017-11-07 | 2019-03-21 | (주)경인양행 | Method for preparing environment-friendly reactive dyes |
| CN111253776B (en) * | 2020-02-13 | 2022-03-04 | 浙江蓝天海纺织服饰科技有限公司 | Dark blue reactive dye formula for all-cotton and all-cotton blended fabric and application |
| CN114621602B (en) * | 2022-04-06 | 2023-06-30 | 浙江亿得新材料股份有限公司 | Compounding method of active dark blue dye suitable for dyeing composite cellulose fiber, product and application thereof |
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