NO125638B - - Google Patents
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- NO125638B NO125638B NO13893561A NO13893561A NO125638B NO 125638 B NO125638 B NO 125638B NO 13893561 A NO13893561 A NO 13893561A NO 13893561 A NO13893561 A NO 13893561A NO 125638 B NO125638 B NO 125638B
- Authority
- NO
- Norway
- Prior art keywords
- group
- amino
- sulfonic acid
- residue
- dyes
- Prior art date
Links
- 239000000975 dye Substances 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 15
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 14
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 10
- -1 aminomonoazo Chemical group 0.000 claims description 10
- 238000009833 condensation Methods 0.000 claims description 10
- 230000005494 condensation Effects 0.000 claims description 10
- 239000007859 condensation product Substances 0.000 claims description 10
- 150000008049 diazo compounds Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 6
- 238000010168 coupling process Methods 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- IHDBZCJYSHDCKF-UHFFFAOYSA-N 4,6-dichlorotriazine Chemical class ClC1=CC(Cl)=NN=N1 IHDBZCJYSHDCKF-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 230000004048 modification Effects 0.000 claims description 4
- 238000012986 modification Methods 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 4
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical group C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims 1
- 229910006069 SO3H Inorganic materials 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical class NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 5
- PHRVJZNHPVJYOM-UHFFFAOYSA-N 5-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(N)C(S(O)(=O)=O)=C1 PHRVJZNHPVJYOM-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000001488 sodium phosphate Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- GINUIEXFKFIZSF-UHFFFAOYSA-N 1-(methylamino)ethanesulfonic acid Chemical compound CNC(C)S(O)(=O)=O GINUIEXFKFIZSF-UHFFFAOYSA-N 0.000 description 1
- VHYBUUMUUNCHCK-UHFFFAOYSA-N 2,4,6-tribromo-1,3,5-triazine Chemical compound BrC1=NC(Br)=NC(Br)=N1 VHYBUUMUUNCHCK-UHFFFAOYSA-N 0.000 description 1
- OMRXVBREYFZQHU-UHFFFAOYSA-N 2,4-dichloro-1,3,5-triazine Chemical group ClC1=NC=NC(Cl)=N1 OMRXVBREYFZQHU-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- FROLMIGPHKATQS-UHFFFAOYSA-N 2-amino-5-benzamidobenzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1NC(=O)C1=CC=CC=C1 FROLMIGPHKATQS-UHFFFAOYSA-N 0.000 description 1
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 1
- FOINSAWEWXUXPQ-UHFFFAOYSA-N 4-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(S(O)(=O)=O)C(N)=C1 FOINSAWEWXUXPQ-UHFFFAOYSA-N 0.000 description 1
- GHBWBMDGBCKAQU-OWOJBTEDSA-N 5-amino-2-[(e)-2-(4-nitro-2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O GHBWBMDGBCKAQU-OWOJBTEDSA-N 0.000 description 1
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- JTXJZBMXQMTSQN-UHFFFAOYSA-N amino hydrogen carbonate Chemical class NOC(O)=O JTXJZBMXQMTSQN-UHFFFAOYSA-N 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000009967 direct dyeing Methods 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003152 propanolamines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical group OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 229960005369 scarlet red Drugs 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F26—DRYING
- F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
- F26B13/00—Machines and apparatus for drying fabrics, fibres, yarns, or other materials in long lengths, with progressive movement
- F26B13/10—Arrangements for feeding, heating or supporting materials; Controlling movement, tension or position of materials
- F26B13/14—Rollers, drums, cylinders; Arrangement of drives, supports, bearings, cleaning
- F26B13/18—Rollers, drums, cylinders; Arrangement of drives, supports, bearings, cleaning heated or cooled, e.g. from inside, the material being dried on the outside surface by conduction
- F26B13/183—Arrangements for heating, cooling, condensate removal
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21F—PAPER-MAKING MACHINES; METHODS OF PRODUCING PAPER THEREON
- D21F5/00—Dryer section of machines for making continuous webs of paper
- D21F5/02—Drying on cylinders
Description
Fremgangsmåte til fremstilling av nye monoazo-fargestoffer. Process for the production of new monoazo dyes.
Foreliggende oppfinnelse angår nye verdifulle monoazofargestoffer, som inneholder minst to sterkt sure, vannoppløseliggjørende grupper, og en 4-amino-2-halogen-l,3,5-triazinrest, som er bundet til fargestoffmolekylet over en aminobro, fortrinnsvis over en aminogruppe med formelen -N- (hvori n betyr et helt The present invention relates to new valuable monoazo dyes, which contain at least two strongly acidic, water-solubilizing groups, and a 4-amino-2-halo-1,3,5-triazine residue, which is bound to the dye molecule via an amino bridge, preferably via an amino group with the formula -N- (where n means a hero
I IN
Cn-lH2n-l Cn-1H2n-1
positivt tall) i /^-stilling i en /?-aminonaftalin7 positive number) in the /^-position in a /?-aminonaphthalene7
sulfonsyre som er bundet til azogruppen i nabostilling til en oksygruppe og hvis 4-stående aminogruppe inneholder høyst 12 kullstoff atomer. sulfonic acid which is bound to the azo group in a neighboring position to an oxy group and whose 4-standing amino group contains no more than 12 carbon atoms.
Som slike fargestoffer skal fremfor alt nevnes slike med formelen As such dyes, those with the formula should above all be mentioned
hvori X betyr en NH2-gruppe eller resten av et organisk, fortrinnsvis primært monoamin, som inneholder høyst 12 kullstoffatomer og i tilfelle det er aromatisk, inneholder en sulfonsyre- eller karboksylgruppe, n betyr et helt positivt tall med en verdi på høyst 3, D betyr resten av en diazokomponent, R betyr en aromatisk rest, fortrinnsvis en bensolrest, som er bundet til en -N-gruppe direkte eller over i wherein X means an NH2 group or the residue of an organic, preferably primary monoamine, containing at most 12 carbon atoms and in case it is aromatic, containing a sulphonic acid or carboxylic group, n means an integer positive number with a value of not more than 3, D means the residue of a diazo component, R means an aromatic residue, preferably a benzol residue, which is attached to an -N group directly or through
Cn-lHan-l Cn-lHan-l
en -CO- eller -S02-gruppe, og m betyr et helt positivt tall med en verdi på høyst 2, og idet det i minst en av restene D, R og X er tilstede en sur vannoppløseliggjørende gruppe. a -CO- or -SO2 group, and m means an integer positive number with a value of at most 2, and in that at least one of the residues D, R and X is present an acidic water-solubilizing group.
Resten D kan være en usubstituert fenyl-rest eller en metyl-, alkoksy-, klor- eller nitro- The residue D can be an unsubstituted phenyl residue or a methyl, alkoxy, chlorine or nitro
fenylrest eller en ennå større rest, f. eks. en bicyklisk rest, slik som en naftalin- eller difenyl-rest. phenyl residue or an even larger residue, e.g. a bicyclic residue, such as a naphthalene or diphenyl residue.
Ved siden av en triazinsubstituent av den angitte art, inneholder fargestoffene ifølge oppfinnelsen ennå minst to sterkt sure, vannopp-løseliggjørende grupper, slik som karboksyl-eller fremfor alt sulfonsyregrupper. Disse vann-oppløseliggjørende grupper kan være fordelt vilkårlig i fargestoffmolekylet. In addition to a triazine substituent of the type indicated, the dyes according to the invention also contain at least two strongly acidic, water-solubilizing groups, such as carboxyl or, above all, sulfonic acid groups. These water-solubilizing groups can be distributed arbitrarily in the dye molecule.
Fargestoffene ifølge oppfinnelsen kan man fremstille av de tilsvarende fargestoffer som The dyes according to the invention can be produced from the corresponding dyes such as
oppviser en dihalogen-, særlig en 2,4-diklor-1,3,5-triazinrest ved kondensasjon, idet man i exhibits a dihalogen, in particular a 2,4-dichloro-1,3,5-triazine residue upon condensation, as in
slike diklortriazinfargestoffer erstatter et av de to kloratomer ved omsetning med ammoniakk eller med en fortrinnsvis primær amin, som such dichlorotriazine dyes replace one of the two chlorine atoms by reaction with ammonia or with a preferably primary amine, which
inneholder minst to kullstoffatomer, og som oppviser en karboksyl- eller sulfonsyregruppe, i tilfelle det inneholder en aromatisk kjerne, med en tilsvarende rest. De dihalogentriazinfargestoffer som skal anvendes for dette, kan fremstilles etter i og for seg kjente fremgangsmåter ved omsetning av aminomonoazofargestoffer, som inneholder en acylerbar aminogruppe i /J-stilling i en /V-aminonaftalinsulfon-syre som er bundet til azogruppen i nabostilling til en oksygruppe med cyanurhalogenider, særlig med cyanurklorid (2,4,6-triklor-l,3,5-tri-azin) i det molekylare forhold på minst 1 : 1 eller fås av de tilsvarende fargestoff komponenter som inneholder diklortriazinrester. containing at least two carbon atoms, and exhibiting a carboxylic or sulfonic acid group, in case it contains an aromatic nucleus, with a corresponding residue. The dihalotriazine dyes to be used for this can be produced according to methods known per se by reacting aminomonoazo dyes, which contain an acylatable amino group in the /J position in a /V-aminonaphthalenesulfonic acid which is bound to the azo group in the adjacent position to an oxy group with cyanuric halides, in particular with cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) in the molecular ratio of at least 1:1 or obtained from the corresponding dye components containing dichlorotriazine residues.
Hvis de dihalogentriazinfargestoffer som herved skal anvendes som utgangsstoffer, alle-rede inneholder to eller flere vannoppløselig-gjørende grupper kan man ved omsetningen anvende et for sure, vannoppløseliggjørende grupper fritt amin eller ammoniakk, mens det halogenatom som skal erstattes med resten av et amin, som oppviser en vannoppløseliggjør-ende gruppe, må ombyttes i tilfelle det i dihalo-gentriazinfargestoffet er tilstede en eneste vann-oppløseliggjørende gruppe. If the dihalotriazine dyes that are to be used as starting materials already contain two or more water-solubilizing groups, an acidic, water-solubilizing group-free amine or ammonia can be used during the reaction, while the halogen atom that is to be replaced with the remainder of an amine, which exhibits a water-solubilizing group, must be exchanged in the event that a single water-solubilizing group is present in the dihalotriazine dye.
For fremstilling av de acylerbare utgangsstoffer som skal kondenseres med cyanurklorid kommer som azokomponenter />-aminonaftalinsulfonsyrer i betraktning, som takket være nærvær av en aromatisk bundet oksygruppe kan koble. Som slike azokomponenter kan f. eks. nevnes: 2-amino-6-oksynaftalin-8-sulfonsyre, 2-amino-8-oksynaftalin-6-sulfonsyre, 2-N-metylamino-8-oksynaftalin-6-sulfonsyre, 2-alkyl- eller -arylamino-5-oksynaftalin-7-sul fonsyre, For the production of the acylatable starting materials to be condensed with cyanuric chloride, />-aminonaphthalenesulfonic acids are considered as azo components, which, thanks to the presence of an aromatically bound oxy group, can couple. As such azo components, e.g. are mentioned: 2-amino-6-oxynaphthalene-8-sulfonic acid, 2-amino-8-oxynaphthalene-6-sulfonic acid, 2-N-methylamino-8-oxynaphthalene-6-sulfonic acid, 2-alkyl- or -arylamino-5- oxynaphthalene-7-sul phonic acid,
2-amino-5-oksynaftalin-7-sulfonsyre, 2-amino-5-oksynaftalin-l,7-disulfonsyre, 2-(4'-aminobenzoylamino)-5-oksynaftalin-7-sulfonsyre, 2-amino-5-oxynaphthalene-7-sulfonic acid, 2-amino-5-oxynaphthalene-1,7-disulfonic acid, 2-(4'-aminobenzoylamino)-5-oxynaphthalene-7-sulfonic acid,
2-(4'-aminofenylamino)-5-oksynaftalin-7-sulfonsyre, 2-(4'-aminophenylamino)-5-oxynaphthalene-7-sulfonic acid,
2-(4'-aminofenylamino)-5-oksynaftalin-3',7-disulfonsyre. 2-(4'-Aminophenylamino)-5-oxynaphthalene-3',7-disulfonic acid.
De diazokomponenter som skal kobles med disse azokomponenter kan oppvise ikke-vann-oppløseliggjørende substituenter, og kan være både relativt enkle forbindelser f. eks. amino-bensolsulfonsyrer, aminonaftalinsulfonsyrer, aminopyren- eller -krysensulfonsyrer, aminonaftolsulfonsyrer eller aminofenolsulfonsyrer og også mer kompliserte diazoterbare forbindelser. The diazo components to be connected with these azo components can have non-water-solubilizing substituents, and can be both relatively simple compounds, e.g. aminobenzenesulfonic acids, aminonaphthalenesulfonic acids, aminopyrene or chrysenesulfonic acids, aminonaphtholsulfonic acids or aminophenolsulfonic acids and also more complicated diazotizable compounds.
Som eksempler på aminer, hvis diazofor-. bindelse kan anvendes for kobling med de angitte acylerbare aminogruppeholdige azokomponenter, kan det f. eks. nevnes følgende amino-sulfonsyrer. l-aminobensol-2-, -3- eller -4-sulfonsyre, l-aminobensol-2-, -3- eller -4-karbonsyre, - 2- amino-l-metoksybensol-4-sulfonsyre, 3- amino-2-oksybensosyre-5-sulfonsyre, 3- amino-6-oksybensosyre-5-sulfonsyre, 2-aminofenol-4-sulfonsyre, 5-acetylamino-2-aminobensol-l-sulfonsyre, 4- acetylamino-2-aminobensol-l-sulfonsyre, 5- acetylamino- eller 5-benzoylamino-2-amino- bensol-l-karbonsyre, 2-aminobensosyre-4- eller -5-sulfonsyre, 1- aminonaftalin-4-, -5-, -6-, eller -7-sulfonsyre, 2- aminonaftalin-4-, -6-, -7- eller -8-sulfonsyre, l-aminonaftalin-3,6-disulfonsyre, 1- aminobensol-2,5-disulfonsyre, 2- aminonaftalin-4,8-, -5,7 eller -6,8-disulfonsyre, l-(3'- eller 4'-aminobenzoyl)-aminobensol-3- sulfonsyre, 3- aminopyren-8- eller -10-monosulfonsyre, 3- aminopyren-5,8- eller -5,10-disulfonsyre, 4- nitro-4'-aminostilben-2,2'-disulfonsyre, videre O-acylderivater av aminonaftolsulfonsyrer, f.eks. 0- acylderivatene av l-amino-8-oksynaftalin-3,6-eller -4,6-disulfonsyre, dehydrotiotoluidin-mono- eller As examples of amines, if diazofor-. bond can be used for coupling with the specified acylatable amino group-containing azo components, it can e.g. the following amino-sulfonic acids are mentioned. l-aminobenzene-2-, -3- or -4-sulfonic acid, l-aminobenzene-2-, -3- or -4-carboxylic acid, - 2-amino-l-methoxybenzene-4-sulfonic acid, 3- amino-2 -oxybenzoic acid-5-sulfonic acid, 3-amino-6-oxybenzoic acid-5-sulfonic acid, 2-aminophenol-4-sulfonic acid, 5-acetylamino-2-aminobenzene-l-sulfonic acid, 4-acetylamino-2-aminobenzene-l-sulfonic acid , 5-acetylamino- or 5-benzoylamino-2-amino- benzol-l-carboxylic acid, 2-aminobenzoic acid-4- or -5-sulfonic acid, 1- aminonaphthalene-4-, -5-, -6-, or -7-sulfonic acid, 2- aminonaphthalene-4-, -6-, -7- or -8 -sulfonic acid, l-aminonaphthalene-3,6-disulfonic acid, 1- aminobenzene-2,5-disulfonic acid, 2- aminonaphthalene-4,8-, -5,7 or -6,8-disulfonic acid, l-(3'- or 4'-aminobenzoyl)-aminobenzene-3-sulfonic acid, 3-aminopyrene-8- or -10-monosulfonic acid, 3-aminopyrene-5,8- or -5,10-disulfonic acid, 4-nitro-4'-aminostilbene- 2,2'-disulfonic acid, further O-acyl derivatives of aminonaphtholsulfonic acids, e.g. The 0- acyl derivatives of l-amino-8-oxynaphthalene-3,6-or -4,6-disulfonic acid, dehydrothiotoluidine-mono- or
-disulfonsyre osv. -disulfonic acid etc.
Kondensasjonen av de aminomonoazofargestoffer som fås fra disse komponenter med cyanurklorid skal foretas således at det i det erholdte kondensasjonsprodukt ennå blir tilbake to utbyttbare halogenatomer av hvilke ett ifølge foreliggende fremgangsmåte utbyttes mot resten av en aminoforbindelse av den angitte art. Som slike aminoforbindelser kommer herved ved siden av ammoniakk aminer, slik som metyl, dimetyl, etyl, dietyl, propyl, isopropyl, butyl, heksyl eller cykloheksylamin, piperidin, morfolin, videre /y<->kloretylamin, me-toksyetylamin, y -metoksypropylamin, etanol-aminer, propanolaminer og acylerte aminer, slik som acetamid, smørsyreamid, urinstoff, tiourinstoff, hydrazin, tiosemikarbasid og tol-uolsulfonsyreamid, samt glykokol, aminokull-syreester, slik som metyl, eller etylester, amino-eddiksyreetylester, aminoacetamid og særlig 1- aminobensol-2,5-disulfonsyre, 1-aminobensol-2- , -3- eller -4-sulfonsyre, l-aminobensol-2-, -3-eller -4-karbonsyre, /V-aminoetansulfonsyre og N-metylaminoetansulfonsyre i betraktning. The condensation of the aminomonoazo dyes obtained from these components with cyanuric chloride must be carried out in such a way that two exchangeable halogen atoms are still left in the obtained condensation product, one of which is exchanged according to the present method for the remainder of an amino compound of the specified species. As such amino compounds, in addition to ammonia, amines such as methyl, dimethyl, ethyl, diethyl, propyl, isopropyl, butyl, hexyl or cyclohexylamine, piperidine, morpholine, further /y<->chloroethylamine, methoxyethylamine, y-methoxypropylamine , ethanolamines, propanolamines and acylated amines, such as acetamide, butyric acid amide, urea, thiourea, hydrazine, thiosemicarbazide and toluenesulphonic acid amide, as well as glycocol, amino carbonic acid esters, such as methyl, or ethyl ester, aminoacetic acid ethyl ester, aminoacetamide and especially 1 - aminobenzene-2,5-disulfonic acid, 1-aminobenzene-2-, -3- or -4-sulfonic acid, 1-aminobenzene-2-, -3- or -4-carboxylic acid, /V-aminoethanesulfonic acid and N-methylaminoethanesulfonic acid in consideration.
Kondensasjonen ifølge oppfinnelsen av disse amino-forbindelser med di-halogentriazinfarge-stoffer utfører man hensiktsmessig under an-vendelse av syrebindende middel, slik som natriumacetat, natriumkarbonat eller natriumhydroksyd, og under slike betingelser at det i det ferdige produkt ennå blir tilbake et utbytt-bart halogenatom, dvs. f. eks. i organiske oppløsningsmidler, eller ved relativt lave temperaturer i vandig middel. The condensation according to the invention of these amino compounds with dihalotriazine dyes is suitably carried out using an acid-binding agent, such as sodium acetate, sodium carbonate or sodium hydroxide, and under such conditions that in the finished product an exchangeable halogen atom, i.e. e.g. in organic solvents, or at relatively low temperatures in an aqueous medium.
Monoazofargestoffene ifølge oppfinnelsen kan likeledes fremstilles ifølge en modifikasjon av den nettopp forklarte fremgangsmåte. Denne modifikasjon av fremgangsmåten består i at man kondenserer de aminomonoazofargestoffer som skal anvendes som utgangsstoffer for fremstilling av diklortriazinfargestoffene, f. eks. de aminomonoazofargestoffer som kan fås av de ovenfor angitte komponenter med dihalogen-triaziner med formelen The monoazo dyes according to the invention can likewise be produced according to a modification of the method just explained. This modification of the method consists in condensing the aminomonoazo dyes that are to be used as starting materials for the production of the dichlorotriazine dyes, e.g. the aminomonoazo dyes which can be obtained from the above-mentioned components with dihalo-triazines of the formula
hvori Y betyr en aminogruppe som høyst inneholder 12 kullstoffatomer og som må inneholde en vannoppløseliggjørende gruppe, i tilfelle det i utgangsmonoazofargestoffet er tilstede en eneste sulfonsyregruppe. in which Y means an amino group containing at most 12 carbon atoms and which must contain a water-solubilizing group, in case a single sulfonic acid group is present in the starting monoazo dye.
Dihalogentriazinene med denne sammen-setning kan fremstilles etter i og for seg kjente fremgangsmåter av cyanurhalogenider, slik som cyanurbromid, eller cyanurklorid, idet man f. eks. omsetter 1 mol cyanurklorid med 1 mol ammoniakk eller med 1 mol av de ovenfor angitte aminer. De således erholdte dihalogen-triazinforbindelser med formel (2), kan for fremstilling av monoazofargestoffene ifølge oppfinnelsen kondenseres med ferdige aminomonoazofargestoffer av den angitte art, som oppviser en acylerbar aminogruppe, eller fordelaktig med de azokomponenter som skal anvendes til fremstilling av slike fargestoffer, og som ved siden av de grupper som er egnet til fargestoff-fremstilling, også inneholder en acylerbar aminogruppe. The dihalotriazines with this composition can be prepared according to methods known per se from cyanuric halides, such as cyanuric bromide or cyanuric chloride, e.g. reacts 1 mol of cyanuric chloride with 1 mol of ammonia or with 1 mol of the above-mentioned amines. The thus obtained dihalo-triazine compounds with formula (2) can, for the production of the monoazo dyes according to the invention, be condensed with ready-made aminomonoazo dyes of the specified type, which exhibit an acylatable amino group, or advantageously with the azo components to be used for the production of such dyes, and which next to the groups suitable for dye production, also contains an acylatable amino group.
Som eksempler på azokomponenter som kan fremstilles på denne måte, og som oppviser en 4- amino-2-halogentriazinrest av den angitte art, skal nevnes: De sekundære kondensasjonsprodukter av et mol cyanurklorid, 1 mol ammoniakk eller 1 mol av en aminobensolsulfonsyre og 1 mol 2-amino-8-oksynaftalin-6-sulfonsyre, 2-amino-5-oksynaftalin-7-sulfonsyre, 2-amino-6-oksynafta-lin-8-sulfonsyre eller 2-(4'-aminobenzoylamino)-5- oksynaftalin-7-sulfonsyre. As examples of azo components which can be prepared in this way, and which exhibit a 4-amino-2-halogenotriazine residue of the type indicated, the following should be mentioned: The secondary condensation products of one mole of cyanuric chloride, 1 mole of ammonia or 1 mole of an aminobenzene sulphonic acid and 1 mole 2-amino-8-oxynaphthalene-6-sulfonic acid, 2-amino-5-oxynaphthalene-7-sulfonic acid, 2-amino-6-oxynaphthalene-8-sulfonic acid or 2-(4'-aminobenzoylamino)-5-oxynaphthalene -7-sulfonic acid.
Ved fremstillingen av fargestoffene ifølge oppfinnelsen ved kondensasjon av et av de nevnte aminoazofargestoffer med cyanurklorid og et av de likeledes oppførte enklere aminer, kan for det meste rekkefølgen for kondensasjonen velges vilkårlig. De kondensasjoner som er nødvendige for fremstilling av de sekundære kondensasjonsprodukter, som skal anvendes som koblingskomponenter, kan likeledes foretas i vilkårlig rekkefølge. Hvis de således erholdte, sekundære kondensasjonsprodukter som skal anvendes som koblingskomponenter inneholder to eller flere enn to vannoppløseliggjørende grupper, kan de ikke bare kombineres med de som diazokomponenter angitte aminosulfon-syrer og aminobensolkarbonsyrer, men også med aminer, som er fri for sure, vannoppløselig-gjørende grupper, f. eks. med klor og/eller nitro-aniliner, alkoksy, alkyl eller acylamino-amino-bensoler. In the production of the dyes according to the invention by condensation of one of the aforementioned aminoazo dyes with cyanuric chloride and one of the similarly listed simpler amines, the order of the condensation can mostly be chosen arbitrarily. The condensations which are necessary for the production of the secondary condensation products, which are to be used as coupling components, can likewise be carried out in any order. If the thus obtained secondary condensation products to be used as coupling components contain two or more water-solubilizing groups, they can not only be combined with the aminosulfonic acids and aminobenzenecarboxylic acids specified as diazo components, but also with amines, which are free of acidic, water-soluble working groups, e.g. with chlorine and/or nitro-anilines, alkoxy, alkyl or acylamino-amino-benzenes.
Til tross for nærvær av labile halogenatomer i fargestoffene ifølge oppfinnelsen kan de, uten å tape sine verdifulle egenskaper isoleres og forarbeides til brukbare, tørre fargepreparater. Isoleringen ifølge oppfinnelsen foregår fortrinnsvis ved lavest mulige temperaturer ved utsalt-ning og filtrering. De filtrerte fargestoffer kan, eventuelt etter tilsetning av Coupagemidler og/ eller puffermidler, f. eks. etter tilsetning av en blanding av like deler mono- og dinatrium-fosfat, tørkes. Fortrinnsvis foretas tørkingen ved ikke for høye temperaturer, og under for-minsket trykk. Ved forstøvningstørking av hele fremstillingsblandingen kan man i visse tilfelle fremstille de tørre preparater ifølge oppfinnelsen, direkte, dvs. uten mellomisolering av fargestoffene.. Despite the presence of labile halogen atoms in the dyes according to the invention, they can, without losing their valuable properties, be isolated and processed into usable, dry color preparations. The isolation according to the invention preferably takes place at the lowest possible temperatures during salting out and filtration. The filtered dyes can, possibly after the addition of Coupage agents and/or buffer agents, e.g. after adding a mixture of equal parts of mono- and disodium phosphate, dry. Preferably, the drying is carried out at temperatures that are not too high, and under reduced pressure. By spray drying the entire manufacturing mixture, the dry preparations according to the invention can in certain cases be produced directly, i.e. without intermediate isolation of the dyes.
De nye fargestoffer ifølge oppfinnelsen egner seg til farging og påtrykning på de forskjelligste materialer, særlig celluloseholdige materialer av fiberaktig struktur, slik som lin, regenerert cellulose og fremfor alt bomull. De egner seg særlig til farging ifølge den såkalte Pad-farge-metode, ifølge hvilken varen impregneres med vandige, og eventuelt også saltholdige farge-stoffoppløsninger, og fargestoffene etter en alkalibehandling, fortrinnsvis i varmen, fikseres. Denne fremgangsmåte og direktfargemetoden som også kan anvendes med mange av de fargestoffer som fås ifølge foreliggende fremgangsmåte, gir farginger som, som regel ut-merker seg ved renhet i sine fargenyanser, ved en god lysekthet og fremfor alt ved fremragende vaskeektheter. The new dyes according to the invention are suitable for dyeing and printing on a wide variety of materials, especially cellulose-containing materials of a fibrous structure, such as linen, regenerated cellulose and, above all, cotton. They are particularly suitable for dyeing according to the so-called Pad-dye method, according to which the product is impregnated with aqueous, and possibly also saline, dye solutions, and the dyes are fixed after an alkali treatment, preferably in the heat. This method and the direct dyeing method, which can also be used with many of the dyes obtained according to the present method, give dyeings which, as a rule, are distinguished by the purity of their color shades, by good light fastness and, above all, by excellent washing fastness.
Ifølge trykk-fremgangsmåten får man likeledes verdifulle og ekte trykk når fargestoffene fikseres på den påtrykkede vare, ved varmebe-handling i nærvær av alkali. According to the printing method, valuable and genuine prints are also obtained when the dyes are fixed on the printed item, by heat treatment in the presence of alkali.
Hvis fargestoffene inneholder metallkom-pleksdannende grupper, f. eks. 0,0'-dioksyazo-grupperinger eller O-oksykarboksy-grupperinger, slik som de forekommer f. eks. i salicylsyre-rester, kan de dermed erholdte farginger be-handles med metallavgivende, f. eks. krom-avgivende, fortrinnsvis med nikkel- og kobber-avgivende midler. Behandlingen med de metallavgivende midler kan foregå ifølge vanlige i og for seg kjente fremgangsmåter. Eventuelt kan det fås meget verdifulle farginger, når man arbeider ifølge den fremgangsmåte ifølge hvilken de farginger som er fremstilt med de metallfri fargestoffer, etterbehandles med slike vandige oppløsninger som inneholder vannoppløselige særlig komplekse kobberforbindelser, og basiske formaldehydkondensasjonsprodukter, av forbindelser som minst en gang inneholder atom-grupperingen If the dyes contain metal complex-forming groups, e.g. 0,0'-dioxyazo groups or O-oxycarboxy groups, as they occur e.g. in salicylic acid residues, the colorings thus obtained can be treated with metal-releasing agents, e.g. chrome-releasing, preferably with nickel and copper-releasing agents. The treatment with the metal-releasing agents can take place according to usual methods known per se. Optionally, very valuable dyeings can be obtained, when working according to the method according to which the dyeings produced with the metal-free dyes are post-treated with such aqueous solutions that contain water-soluble particularly complex copper compounds, and basic formaldehyde condensation products, of compounds that contain at least one atom - the grouping
i molekylet, eller som slik som f. eks. cyanamid, lett kan gå over i slike forbindelser. in the molecule, or as such as e.g. cyanamide, can easily pass into such compounds.
I de følgende eksempler betyr deler, såfremt intet annet angis, vektsdeler; prosentene vekts-prosenter og temperaturene er angitt i Celsius-grader. In the following examples, parts, unless otherwise stated, means parts by weight; the percentages by weight and the temperatures are given in degrees Celsius.
Eksempel 1. Example 1.
46,7 deler av dinatriumsaltet av det av 1 46.7 parts of the disodium salt of that of 1
mol diazotert l-aminobensol-3-sulfonsyre og 1 mol 2-amino-5-oksynaftalin-7-sulfonsyre i alkal- mol of diazotized l-aminobenzene-3-sulfonic acid and 1 mol of 2-amino-5-oxynaphthalene-7-sulfonic acid in alkaline
isk medium fremstillbare monbazofargestoff, oppløses i 2000 deler vann og settes til en iskald suspensjon av 18,4 deler cyanurklorid i 200 deler vann, hvoretter man i løpet av 1 til 2 timer lar omtrent 50 volumdeler 2-n.-natrium-karbonatoppløsning dryppe tii. Reaksjonen skal derved alltid forbli svakt sur, (pH = 5 til 6), og temperaturen holdes mellom 0 og 5°. Når det ikke lenger kan påvises noen fri aminogruppe tilsetter man 35 deler 10 %'s ammoniakkopp-løsning, og rører 4 timer ved 30—40°. Deretter utsaltes fargestoffet med natriumklorid, filtreres og tørkes. Det oppløser seg i vann med gul-oransje farge og farger bomull ifølge Pad-farge-metoden, eller fra sterkt saltholdig alkalisk oppløsning i rene oransje nyanser. monbazo dye, which can be prepared in an icy medium, is dissolved in 2000 parts of water and added to an ice-cold suspension of 18.4 parts of cyanuric chloride in 200 parts of water, after which, in the course of 1 to 2 hours, about 50 parts by volume of 2-n sodium carbonate solution are allowed to drip into . The reaction must therefore always remain slightly acidic, (pH = 5 to 6), and the temperature is kept between 0 and 5°. When no free amino group can be detected anymore, 35 parts of 10% ammonia solution are added, and stirred for 4 hours at 30-40°. The dye is then salted out with sodium chloride, filtered and dried. It dissolves in water with a yellow-orange color and colors cotton according to the Pad color method, or from strongly saline alkaline solution in pure orange shades.
Man får det samme fargestoff når kondensasjonen i ovenstående eksempel foretas om-vendt, dvs. når man først kondenserer ammoniakk med cyanurkloridet og omsetter det dannede primære kondensasjonsprodukt med mono-azofargestoffet. The same dye is obtained when the condensation in the above example is carried out in reverse, i.e. when ammonia is first condensed with the cyanuric chloride and the primary condensation product formed is reacted with the mono-azo dye.
23,9 deler 2-amino-5-oksynaftalin-7-sulfonsyre oppløses i vann under tilsetning av 5,6 deler natriumkarbonat. Oppløsningen lar man langsomt strømme til en iskald suspensjon av 18,4 deler cyanurklorid i 200 deler vann. Deretter tildryppes i løpet av 1 time 50 deler 2-n-natriumkarbonatoppløsning, og da på en slik måte at blandingens reaksjon forblir svakt kongosur. Det således erholdte primære kondensasjonsprodukt tilsettes den diazoforbindelse som fås av 17,3 deler l-aminobensol-2-sulfonsyre. Deretter tilsettes litt etter litt 25 deler natriumbikarbonat og omrøres så lenge under isavkjøling inntil denne ikke lenger kan påvises 23.9 parts of 2-amino-5-oxynaphthalene-7-sulfonic acid are dissolved in water while adding 5.6 parts of sodium carbonate. The solution is allowed to flow slowly into an ice-cold suspension of 18.4 parts cyanuric chloride in 200 parts water. Then, over the course of 1 hour, 50 parts of 2-n-sodium carbonate solution are added dropwise, and then in such a way that the reaction of the mixture remains weakly congoacidic. The primary condensation product thus obtained is added to the diazo compound obtained from 17.3 parts of 1-aminobenzene-2-sulfonic acid. 25 parts of sodium bicarbonate are then added little by little and stirred under ice cooling until this can no longer be detected
noen diazoforbindelse. Deretter utfelles det dannede fargestoff med natriumklorid og filtreres. Den erholdte pasta oppløses i 2000 deler vann og tilsettes 35 deler 10 %'s ammoniakk-oppløsning. Man holder under omrøring 4—6 timer ved 40° feller ved tilsetning av natriumklorid, filtrerer og tørker det dannede fargestoff i vakuum. Det farger bomull i oransje-nyanser. some diazo compound. The dye formed is then precipitated with sodium chloride and filtered. The obtained paste is dissolved in 2000 parts of water and 35 parts of 10% ammonia solution are added. The mixture is kept under stirring for 4-6 hours at 40°, then by the addition of sodium chloride, the dye formed is filtered and dried in a vacuum. It dyes cotton in orange shades.
Eksempel 3. Example 3.
23 deler 5-acetylamino-2-aminobensol-l-sulfonsyre diazoteres i nærvær av saltsyre med 23 parts of 5-acetylamino-2-aminobenzene-1-sulfonic acid are diazotized in the presence of hydrochloric acid with
6,9 deler natriumnitritt på vanlig måte. Diazo-forbindelsen innføres deretter i en iskald opp-løsning av 38,7 deler av det primære kondensasjonsprodukt som kan fås ifølge den fremgangsmåte som er angitt i eksempel 2 av 1 mol 2-amino-5-oksynaftalin-7-sulfonsyre og 1 mol cyanurklorid, og 25 deler natriumbikarbonat. Etter avsluttet kobling utsaltes fargestoffet, frafiltreres, oppløses i 2000 deler vann og tilsettes en nøytral oppløsning av 17,3 deler l-aminobensol-3-sulfonsyre. Man tilsetter 10 deler krystallisert natriumbikarbonat og rører blandingen 4 til 6 timer ved 30—40°. Deretter utsaltes fargestoffet, frafiltreres og tørkes i vakuum ved 60°. Det oppløser seg med gulrød farge i vann og farger bomull fra sterkt saltholdig alkalisk bad i meget rene, lys- og vask-ekte skarlagensrød nyanser. 6.9 parts sodium nitrite in the usual way. The diazo compound is then introduced into an ice-cold solution of 38.7 parts of the primary condensation product which can be obtained according to the method indicated in example 2 of 1 mol of 2-amino-5-oxynaphthalene-7-sulfonic acid and 1 mol of cyanuric chloride , and 25 parts sodium bicarbonate. After coupling is complete, the dye is salted out, filtered off, dissolved in 2000 parts of water and a neutral solution of 17.3 parts of 1-aminobenzene-3-sulfonic acid is added. 10 parts of crystallized sodium bicarbonate are added and the mixture is stirred for 4 to 6 hours at 30-40°. The dye is then salted out, filtered off and dried in a vacuum at 60°. It dissolves with a yellow-red color in water and dyes cotton from a strongly saline alkaline bath in very clean, bright and wash-proof scarlet shades.
Eksempel %. Example %.
Den diazoforbindelse som er fremstilt på vanlig måte av 23 deler 5-acetylamino-2-aminobensol-l-sulfonsyre kobles i nærvær av natriumbikarbonat - med 52,3 deler av det sekundære kondensasjonsprodukt av 1 mol cyanurklorid, 1 mol 2-amino-5-oksynaftalin-7-sulfonsyre og 1 mol l-aminobensol-3-sulfonsyre. Det erholdte fargestoff viser praktisk talt de samme egenskaper som det fargestoff som er fremstilt ifølge eksempel 3. The diazo compound prepared in the usual way from 23 parts of 5-acetylamino-2-aminobenzene-l-sulfonic acid is coupled in the presence of sodium bicarbonate - with 52.3 parts of the secondary condensation product of 1 mole of cyanuric chloride, 1 mole of 2-amino-5- oxynaphthalene-7-sulfonic acid and 1 mol of 1-aminobenzene-3-sulfonic acid. The dye obtained shows practically the same properties as the dye produced according to example 3.
Eksempel 5. Example 5.
17,3 deler l-aminobensol-2-sulfonsyre opp-løses i 30Q deler vann under tilsetning av 5,3 deler natriumkarbonat. Den erholdte nøytrale oppløsning lar man strømme til en iskald vandig suspensjon av 18,4 deler cyanurklorid, og nøy-traliserer litt etter litt den dannede mineralsyre ved tilsetning av fortynnet natronlut. Så snart kondensasjonen er avsluttet, dvs. når det ikke lenger kan påvises noen fri aminogruppe, lar man en nøytral oppløsning av 23,9 deler 2-amino-5-oksynaftalin-7-sulfonsyre strømme til, og rører blandingen ved 20°. Det tildryppes litt etter litt omtrent 90 deler l-n.-natronlut på en slik måte at pH-verdien ikke går over 6. Kondensasjonen er fullstendig i løpet av omtrent 2 timer. 17.3 parts of 1-aminobenzene-2-sulfonic acid are dissolved in 30Q parts of water while adding 5.3 parts of sodium carbonate. The obtained neutral solution is allowed to flow into an ice-cold aqueous suspension of 18.4 parts of cyanuric chloride, and little by little the mineral acid formed is neutralized by the addition of diluted caustic soda. As soon as the condensation is finished, i.e. when no free amino group can be detected, a neutral solution of 23.9 parts of 2-amino-5-oxynaphthalene-7-sulfonic acid is allowed to flow in, and the mixture is stirred at 20°. About 90 parts of 1-n sodium hydroxide solution are added drop by drop in such a way that the pH value does not exceed 6. Condensation is complete in about 2 hours.
Den erholdte og avkjølte oppløsning tilsettes 20 deler natriumbikarbonat og den diazoforbindelse som er fremstilt av 23 deler 5-acetylamino-2-aminobensol-l-sulfonsyre ifølge eksempel 3. Fargestoffet utfelles delvis. Etter noen timer utsaltes det, frafiltreres og tørkes. Det farger bomull fra sterkt saltholdig alkalisk bad i meget rene, lys- og vaskeekte skarlagens-røde nyanser. To the obtained and cooled solution are added 20 parts of sodium bicarbonate and the diazo compound which is prepared from 23 parts of 5-acetylamino-2-aminobenzene-1-sulfonic acid according to example 3. The dye partially precipitates. After a few hours, it is salted out, filtered off and dried. It dyes cotton from a highly saline alkaline bath in very clean, light- and wash-fast scarlet-red shades.
Liknende fargestoffer som farger bomull i de i kolonne 4 angitte nyanser, fås når man i stedet for l-aminobensol-2-sulfonsyre anvender de i kolonne 3 nevnte forbindelser i stedet for 2-amino-5-oksynaftalin-7-sulfonsyre, anvender de i kolonne 2 oppførte forbindelser, og i stedet for den diazoforbindelse som fås av 5-acetylamino-2-aminobensol-l-sulfonsyre anvender de diazoforbindelser som fås av de i kolonne 1 nevnte aminer. oppløses ved oppkokning i 100 deler vann. Oppløsningen setter man til 3900 deler kaldt vann, tilsetter 40 deler trinatriumfosfat og 80 deler natriumklorid og går inn med 100 deler av en bomullsstoff i dette fargebad. Similar dyes that color cotton in the shades indicated in column 4 are obtained when, instead of 1-aminobenzene-2-sulfonic acid, the compounds mentioned in column 3 are used instead of 2-amino-5-oxynaphthalene-7-sulfonic acid, they use compounds listed in column 2, and instead of the diazo compound obtained from 5-acetylamino-2-aminobenzene-1-sulfonic acid, they use diazo compounds obtained from the amines mentioned in column 1. dissolves by boiling in 100 parts water. The solution is made up of 3,900 parts of cold water, 40 parts of trisodium phosphate and 80 parts of sodium chloride are added and 100 parts of a cotton cloth are introduced into this dye bath.
Man øker temperaturen i 45 minutter til 90°, idet det etter 30 minutter nok en gang tilsettes 80 deler natriumklorid. Man holder temperaturen 30 minutter på 90°, skyller og såpebehandler deretter fargingene i 15 minutter i en 0,3 prosents kokende oppløsning av et ionefritt vaskemiddel, skyller og tørker. The temperature is increased for 45 minutes to 90°, and after 30 minutes 80 parts of sodium chloride are once again added. The temperature is kept at 90° for 30 minutes, the dyes are then rinsed and treated with soap for 15 minutes in a 0.3 per cent boiling solution of an ion-free detergent, rinsed and dried.
Det resulterer i en vaske- og lysekte ren oransjefarging. This results in a wash- and light-fast pure orange colouring.
Eksempel 7. Example 7.
1 del av det fargestoff som fås ifølge eksempel 3 oppløses i 100 deler vann. Med den erholdte oppløsning impregneres et cellullstoff, således at det øker med 75 % av sin vekt, og tørkes deretter. 1 part of the dye obtained according to example 3 is dissolved in 100 parts of water. A cellular wool fabric is impregnated with the obtained solution, so that it increases by 75% of its weight, and is then dried.
Deretter impregnerer man stoffet med en 20° varm oppløsning som pr. liter inneholder 10 g natriumhydroksyd og 300 g natriumklorid, vrir til 75 %'s vektsøkning, damper fargingen i 60 sekunder ved 100 til 101°, skyller, såpebehandler i et kvarter i en 0,3 %'s kokende oppløsning av et ionefritt vaskemiddel, skyller og tørker. Man får en vaskeekte, skarlagensrød farging. The fabric is then impregnated with a 20° warm solution which per liter contains 10 g of sodium hydroxide and 300 g of sodium chloride, twist to 75% weight gain, steam the dye for 60 seconds at 100 to 101°, rinse, soap for a quarter of an hour in a 0.3% boiling solution of a non-ionic detergent, rinses and dries. You get a stain-resistant, scarlet colouring.
Anvender man i stedet for cellullstoffet et bomullsstoff, får man et liknende godt resultat. If you use a cotton fabric instead of the cellulose fabric, you get a similarly good result.
Claims (11)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US742660A | 1960-02-08 | 1960-02-08 | |
US307578A US3241251A (en) | 1963-09-09 | 1963-09-09 | Cylindrical dryer |
Publications (1)
Publication Number | Publication Date |
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NO125638B true NO125638B (en) | 1972-10-09 |
Family
ID=31497785
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO13893561A NO125638B (en) | 1960-02-08 | 1961-01-30 | |
NO15204364A NO133280C (en) | 1960-02-08 | 1964-02-17 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
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NO15204364A NO133280C (en) | 1960-02-08 | 1964-02-17 |
Country Status (2)
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GB (2) | GB939926A (en) |
NO (2) | NO125638B (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3299531A (en) * | 1964-08-21 | 1967-01-24 | Kimberly Clark Co | Papermaking machine |
US3367042A (en) * | 1966-08-01 | 1968-02-06 | Newport News S & D Co | Rotary heat exchanger with ribbed inner liner of higher thermal conductivity than outer shell |
CH598409A5 (en) * | 1975-05-12 | 1978-04-28 | Escher Wyss Gmbh | |
US4232455A (en) * | 1977-12-03 | 1980-11-11 | Beloit Corporation | Dryer drum condensate removal apparatus |
DE102005022233A1 (en) * | 2005-05-13 | 2006-11-16 | Voith Patent Gmbh | drying cylinders |
CN102419125A (en) * | 2011-12-16 | 2012-04-18 | 亿恒节能科技江苏有限公司 | Drying cylinder heat exchanger with exhaust function |
CN114541164B (en) * | 2022-04-22 | 2022-06-28 | 溧阳市江南烘缸制造有限公司 | Steel Yankee dryer |
-
1961
- 1961-01-30 NO NO13893561A patent/NO125638B/no unknown
- 1961-02-01 GB GB382861A patent/GB939926A/en not_active Expired
-
1963
- 1963-11-29 GB GB4729063A patent/GB1048578A/en not_active Expired
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1964
- 1964-02-17 NO NO15204364A patent/NO133280C/no unknown
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Publication number | Publication date |
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GB939926A (en) | 1963-10-16 |
NO133280C (en) | 1976-04-07 |
NO133280B (en) | 1975-12-29 |
GB1048578A (en) | 1966-11-16 |
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