CA1070693A - Derives solubles dans l'eau du benzoxanthene et du benzothioxanthene, procede pour leur preparation et leur utilisation comme teintures - Google Patents

Derives solubles dans l'eau du benzoxanthene et du benzothioxanthene, procede pour leur preparation et leur utilisation comme teintures

Info

Publication number: CA1070693A
Authority: CA; Canada
Prior art keywords: radical; formula; compound; carbon atoms; alkyl
Prior art date: 1974-10-02
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA236,841A

Other languages

English (en)

Other versions

CA236841S (en

Inventor

Joachim Otten

Helmut Troster

Konrad Lohe

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1974-10-02

Filing date

1975-10-01

Publication date

1980-01-29

1974-10-02 Priority claimed from DE19742447024 external-priority patent/DE2447024C3/de

1975-10-01 Application filed by Hoechst AG filed Critical Hoechst AG

1980-01-29 Application granted granted Critical

1980-01-29 Publication of CA1070693A publication Critical patent/CA1070693A/fr

Status Expired legal-status Critical Current

Links

VVZRKVYGKNFTRR-UHFFFAOYSA-N 12h-benzo[a]xanthene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4OC3=CC=C21 VVZRKVYGKNFTRR-UHFFFAOYSA-N 0.000 title claims description 11
238000004519 manufacturing process Methods 0.000 title claims 2
YEBQUUKDSJCPIX-UHFFFAOYSA-N 12h-benzo[a]thioxanthene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4SC3=CC=C21 YEBQUUKDSJCPIX-UHFFFAOYSA-N 0.000 title description 6
-1 benzoxanthene- and benzothioxanthene-dicarboxylic acid imide compounds Chemical class 0.000 claims abstract description 47
238000004043 dyeing Methods 0.000 claims abstract description 28
239000004952 Polyamide Substances 0.000 claims abstract description 21
229920002647 polyamide Polymers 0.000 claims abstract description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 15
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 9
239000000835 fiber Substances 0.000 claims abstract description 8
125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 65
150000003254 radicals Chemical class 0.000 claims description 39
125000004432 carbon atom Chemical group C* 0.000 claims description 31
238000006243 chemical reaction Methods 0.000 claims description 21
238000000034 method Methods 0.000 claims description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 17
230000008569 process Effects 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 15
239000000463 material Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
150000003949 imides Chemical class 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 7
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
239000000975 dye Substances 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
210000002268 wool Anatomy 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000000542 sulfonic acid group Chemical group 0.000 claims description 5
229910052717 sulfur Chemical group 0.000 claims description 5
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
239000011593 sulfur Chemical group 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
239000004814 polyurethane Substances 0.000 claims description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical class [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 2
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 2
SWLJARIIAARGGG-UHFFFAOYSA-N 12h-benzo[a]thioxanthene-1,2-dicarboxylic acid Chemical class S1C2=CC=CC=C2CC2=C1C=CC1=CC=C(C(=O)O)C(C(O)=O)=C12 SWLJARIIAARGGG-UHFFFAOYSA-N 0.000 claims description 2
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
239000005711 Benzoic acid Substances 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
150000003863 ammonium salts Chemical class 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
235000010233 benzoic acid Nutrition 0.000 claims description 2
150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
239000004744 fabric Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
150000003385 sodium Chemical class 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 4
239000002657 fibrous material Substances 0.000 claims 2
150000001555 benzenes Chemical class 0.000 claims 1
239000010985 leather Substances 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
230000003381 solubilizing effect Effects 0.000 claims 1
239000003513 alkali Substances 0.000 abstract 1
125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 abstract 1
239000000243 solution Substances 0.000 description 24
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
239000000203 mixture Substances 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
239000001103 potassium chloride Substances 0.000 description 6
235000011164 potassium chloride Nutrition 0.000 description 6
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
159000000000 sodium salts Chemical class 0.000 description 5
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000006277 sulfonation reaction Methods 0.000 description 4
JAXUGYDPUMNJNF-UHFFFAOYSA-N 18-methoxy-7,14-dioxapentacyclo[11.8.0.02,10.05,9.015,20]henicosa-1(13),2(10),3,5(9),11,15(20),16,18-octaene-6,8-dione Chemical compound C1=CC2=C(CC=3C(=CC=C(C=3)OC)O3)C3=CC=C2C2=C1C(=O)OC2=O JAXUGYDPUMNJNF-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
229960003080 taurine Drugs 0.000 description 3
238000009736 wetting Methods 0.000 description 3
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
229910006069 SO3H Inorganic materials 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
150000002440 hydroxy compounds Chemical class 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
238000001694 spray drying Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
QJGHJWKPZQIOSN-UHFFFAOYSA-N (4-aminophenyl)methanesulfonic acid Chemical compound NC1=CC=C(CS(O)(=O)=O)C=C1 QJGHJWKPZQIOSN-UHFFFAOYSA-N 0.000 description 1
MXTPRJXPLFGHEE-UHFFFAOYSA-N 1-amino-2-sulfosulfanylethane Chemical compound NCCSS(O)(=O)=O MXTPRJXPLFGHEE-UHFFFAOYSA-N 0.000 description 1
SBHDBHLJFALKOP-UHFFFAOYSA-N 10-methoxy-12h-benzo[a]xanthene-3,4-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(CC=3C(=CC=C(C=3)OC)O3)C3=CC=C21 SBHDBHLJFALKOP-UHFFFAOYSA-N 0.000 description 1
ITFWCGBCGYMQRP-UHFFFAOYSA-N 12h-benzo[a]thioxanthene-3,4-dicarboxylic acid Chemical compound C1C2=CC=CC=C2SC2=C1C1=CC=C(C(=O)O)C(C(O)=O)=C1C=C2 ITFWCGBCGYMQRP-UHFFFAOYSA-N 0.000 description 1
YUHXJUHMUNEUKC-UHFFFAOYSA-N 17-methyl-7,14-dioxapentacyclo[11.8.0.02,10.05,9.015,20]henicosa-1(13),2(10),3,5(9),11,15(20),16,18-octaene-6,8-dione Chemical compound C1=CC2=C3C(=O)OC(=O)C3=CC=C2C2=C1OC1=CC(C)=CC=C1C2 YUHXJUHMUNEUKC-UHFFFAOYSA-N 0.000 description 1
YCJAUMBAFBAMFV-UHFFFAOYSA-N 1h,3h-thioxantheno(2,1,9-def)-2-benzopyran-1,3-dione Chemical compound C12=CC=CC=C2SC2=CC=C3C(=O)OC(=O)C4=CC=C1C2=C43 YCJAUMBAFBAMFV-UHFFFAOYSA-N 0.000 description 1
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000820057 Ithone Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
XYXNTHIYBIDHGM-UHFFFAOYSA-N ammonium thiosulfate Chemical group [NH4+].[NH4+].[O-]S([O-])(=O)=S XYXNTHIYBIDHGM-UHFFFAOYSA-N 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000007844 bleaching agent Substances 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
229960001506 brilliant green Drugs 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000005521 carbonamide group Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000009963 fulling Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000009998 heat setting Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical group Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
RUAIJHHRCIHFEV-UHFFFAOYSA-N methyl 4-amino-5-chlorothiophene-2-carboxylate Chemical compound COC(=O)C1=CC(N)=C(Cl)S1 RUAIJHHRCIHFEV-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000004957 naphthylene group Chemical group 0.000 description 1
238000013021 overheating Methods 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000004382 potting Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000005185 salting out Methods 0.000 description 1
239000013535 sea water Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/14—Benzoxanthene dyes; Benzothioxanthene dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Compositions Of Macromolecular Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA236,841A 1974-10-02 1975-10-01 Derives solubles dans l'eau du benzoxanthene et du benzothioxanthene, procede pour leur preparation et leur utilisation comme teintures Expired CA1070693A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19742447024 DE2447024C3 (de)		1974-10-02	Neue wasserlösliche Benzoxanthen- und Benzothioxanthenverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben und Bedrucken von natürlichem und synthetischem carbonamidgruppenhaltigem Fasermaterial

Publications (1)

Publication Number	Publication Date
CA1070693A true CA1070693A (fr)	1980-01-29

Family

ID=5927337

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA236,841A Expired CA1070693A (fr)	1974-10-02	1975-10-01	Derives solubles dans l'eau du benzoxanthene et du benzothioxanthene, procede pour leur preparation et leur utilisation comme teintures

Country Status (11)

Country	Link
JP (1)	JPS5945017B2 (fr)
BE (1)	BE834132A (fr)
BR (1)	BR7506390A (fr)
CA (1)	CA1070693A (fr)
CH (1)	CH614728A5 (fr)
FR (1)	FR2286863A1 (fr)
GB (1)	GB1518855A (fr)
IN (1)	IN144020B (fr)
IT (1)	IT1042982B (fr)
LU (1)	LU73481A1 (fr)
NL (1)	NL7511367A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS62165905U (fr) *	1986-04-11	1987-10-21
JPS6384174U (fr) *	1986-11-21	1988-06-02
US9751789B2 (en) *	2012-12-28	2017-09-05	Ecolab Usa Inc.	Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems

1975
- 1975-09-26 NL NL7511367A patent/NL7511367A/xx not_active Application Discontinuation
- 1975-09-29 CH CH1261575A patent/CH614728A5/xx not_active IP Right Cessation
- 1975-09-30 IT IT27787/75A patent/IT1042982B/it active
- 1975-09-30 LU LU73481A patent/LU73481A1/xx unknown
- 1975-09-30 IN IN1867/CAL/1975A patent/IN144020B/en unknown
- 1975-10-01 FR FR7530049A patent/FR2286863A1/fr active Granted
- 1975-10-01 CA CA236,841A patent/CA1070693A/fr not_active Expired
- 1975-10-01 JP JP50117773A patent/JPS5945017B2/ja not_active Expired
- 1975-10-01 BR BR7506390*A patent/BR7506390A/pt unknown
- 1975-10-02 BE BE160638A patent/BE834132A/fr unknown
- 1975-10-02 GB GB40368/75A patent/GB1518855A/en not_active Expired

Also Published As

Publication number	Publication date
GB1518855A (en)	1978-07-26
DE2447024B2 (de)	1976-11-04
FR2286863A1 (fr)	1976-04-30
BR7506390A (pt)	1976-08-17
DE2447024A1 (de)	1976-04-08
LU73481A1 (fr)	1977-05-11
BE834132A (fr)	1976-04-02
IN144020B (fr)	1978-03-11
CH614728A5 (en)	1979-12-14
NL7511367A (nl)	1976-04-06
FR2286863B1 (fr)	1979-05-11
JPS5945017B2 (ja)	1984-11-02
JPS5161531A (fr)	1976-05-28
IT1042982B (it)	1980-01-30

Legal Events

Date	Code	Title	Description
1997-01-29	MKEX	Expiry

Publication	Publication Date	Title
CA1064916A (fr)	1979-10-23	Procede pour la preparation de teintures a base de xanthene
US4577015A (en)	1986-03-18	Triphendioxazine vinyl sulphone dyestuffs
GB1568231A (en)	1980-05-29	Substituted 2,6-dioxo-2,6-dihydrobenzo (1:2-b; 4:5-6')-difuran or dipyrrole dyestuffs
EP0033583B1 (fr)	1983-10-12	Colorants contenant deux hétérocycles à 5 maillons condensés sur un cycle cyclohexadiène central, procédés pour leur préparation et leur utilisation pour la coloration de matières textiles synthétiques
US4604459A (en)	1986-08-05	Triphendioxazine reactive dyestuffs
CA1038377A (fr)	1978-09-12	Preparation et utilisation de colorants azoiques solubles dans l'eau
EP0252508B1 (fr)	1991-01-16	Colorants disazoiques solubles dans l'eau et procédé de teinture les utilisant
US3324151A (en)	1967-06-06	1-amino-4-anilino-anthraquinone-2-sulfonic acids
US3534038A (en)	1970-10-13	Anthrapyrimadone and anthrapyridone dyestuffs containing an n-methylenecarboxamide group
GB2103231A (en)	1983-02-16	Dyestuffs comprising two 5- membered heterocyclic nuclei fused to a central cyclohexa-1,4-diene nucleus
US5075428A (en)	1991-12-24	2,4-diamino-6-fluorotriazine disazo reactive dyestuffs
US3947435A (en)	1976-03-30	Disazo acid compounds containing one sulphonic acid group and one phosphonic or methyl-phosphinic acid group
CA1070693A (fr)	1980-01-29	Derives solubles dans l'eau du benzoxanthene et du benzothioxanthene, procede pour leur preparation et leur utilisation comme teintures
US4033980A (en)	1977-07-05	Phthalocyanine dyestuffs and process for preparing them
US5703215A (en)	1997-12-30	Water-soluble dyes which are polymerizable containing molecules which contain a nucleophilic group and an electrophilic group
US3236860A (en)	1966-02-22	Water-soluble phthalocyanine dyestuffs containing thiosulfuric acid groups
US3354182A (en)	1967-11-21	Anthraquinone dyestuffs
DE2531445C3 (de)	1978-05-11	Sulfogruppenfreie wasserlösliche Azofarbstoffe und deren Verwendung zum Färben und/oder Bedrucken von synthetischen Textilfasern
CA1097622A (fr)	1981-03-17	Colorants solubles dans l'eau, leur preparation et leur emploi pour la teinture et l'impression sur fibres de polyamides et de cellulose
US3294778A (en)	1966-12-27	Fiber-reactive dyestuffs
US3246004A (en)	1966-04-12	New dyestuffs containing benzazolylmercapto substituents
US3617210A (en)	1971-11-02	Process for dyeing polyamides with dyes containing sulfonic acid groups
US3926946A (en)	1975-12-16	Water soluble monoazo dyestuffs containing a diphenylamine group carrying a sulphamoyl substituent and a sulpho or sulphato substituent
US3126369A (en)	1964-03-24	Oh nhxr
CA1060436A (fr)	1979-08-14	Procede pour la preparation de teintures reactives a base de xanthene