CH534713A - Verfahren zur Herstellung von Anthrachinonverbindungen - Google Patents

Verfahren zur Herstellung von Anthrachinonverbindungen

Info

Publication number: CH534713A
Authority: CH; Switzerland
Prior art keywords: sep; formula; parts; dye; radical
Prior art date: 1969-11-21

Application number

CH1735169A

Other languages

German (de)

English (en)

Inventor

Francois Dr Benguerel

Original Assignee

Sandoz 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.)

1969-11-21

Filing date

1969-11-21

Publication date

1973-03-15

Priority to BE759054D priority Critical patent/BE759054A/fr

1969-11-21 Application filed by Sandoz Ag filed Critical Sandoz Ag

1969-11-21 Priority to CH1735169A priority patent/CH534713A/de

1973-03-15 Publication of CH534713A publication Critical patent/CH534713A/de

Links

BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 title abstract 3
239000001000 anthraquinone dye Substances 0.000 title abstract 2
239000004952 Polyamide Substances 0.000 claims abstract description 9
238000004043 dyeing Methods 0.000 claims abstract description 9
229920002647 polyamide Polymers 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 5
229930195733 hydrocarbon Natural products 0.000 claims abstract description 5
125000001424 substituent group Chemical group 0.000 claims abstract description 5
-1 1-tert-butylphenoxy-2-aminopropane Chemical compound 0.000 claims description 31
239000000975 dye Substances 0.000 claims description 23
150000001875 compounds Chemical class 0.000 claims description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
239000004677 Nylon Substances 0.000 claims description 7
229920001778 nylon Polymers 0.000 claims description 7
150000003254 radicals Chemical group 0.000 claims description 7
210000002268 wool Anatomy 0.000 claims description 7
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 6
239000000835 fiber Substances 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
239000004744 fabric Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 claims description 4
125000000542 sulfonic acid group Chemical group 0.000 claims description 4
SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 claims description 3
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
239000010985 leather Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
FVXPBEUYCCZFJT-UHFFFAOYSA-N 9,10-dihydroxy-2,3-dihydroanthracene-1,4-dione Chemical compound C1=CC=C2C(O)=C(C(=O)CCC3=O)C3=C(O)C2=C1 FVXPBEUYCCZFJT-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
229960000583 acetic acid Drugs 0.000 claims description 2
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 2
229910052921 ammonium sulfate Inorganic materials 0.000 claims description 2
235000011130 ammonium sulphate Nutrition 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000012362 glacial acetic acid Substances 0.000 claims description 2
239000012299 nitrogen atmosphere Substances 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
238000010186 staining Methods 0.000 claims description 2
150000003871 sulfonates Chemical class 0.000 claims description 2
150000002367 halogens Chemical class 0.000 abstract description 6
APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical group OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 abstract 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
150000002430 hydrocarbons Chemical class 0.000 abstract 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
BGJCAFDTQVYZEX-UHFFFAOYSA-N 2-phenoxycyclohexan-1-amine Chemical compound NC1CCCCC1OC1=CC=CC=C1 BGJCAFDTQVYZEX-UHFFFAOYSA-N 0.000 description 3
229920000297 Rayon Polymers 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
229920003043 Cellulose fiber Polymers 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000002964 rayon Substances 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
CFOFDTGGGLESBH-UHFFFAOYSA-N 1-bromo-4-(propan-2-ylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2NC(C)C CFOFDTGGGLESBH-UHFFFAOYSA-N 0.000 description 1
CCHNWURRBFGQCD-UHFFFAOYSA-N 2-chlorocyclohexan-1-one Chemical compound ClC1CCCCC1=O CCHNWURRBFGQCD-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 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
238000006243 chemical reaction Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 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
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
RYGMFSIKBFXOCR-AHCXROLUSA-N copper-60 Chemical group [60Cu] RYGMFSIKBFXOCR-AHCXROLUSA-N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000005108 dry cleaning Methods 0.000 description 1
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009963 fulling Methods 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
239000013535 sea water Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
239000004753 textile Substances 0.000 description 1
230000008719 thickening Effects 0.000 description 1
125000004950 trifluoroalkyl group Chemical group 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
- C09B1/30—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups sulfonated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Coloring (AREA)

CH1735169A 1969-11-21 1969-11-21 Verfahren zur Herstellung von Anthrachinonverbindungen CH534713A (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
BE759054D BE759054A (fr)	1969-11-21		Colorants anthraquinoniques portant des radicaux acide sulfonique, leurpreparation et leur utilisation
CH1735169A CH534713A (de)	1969-11-21	1969-11-21	Verfahren zur Herstellung von Anthrachinonverbindungen

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1735169A CH534713A (de)	1969-11-21	1969-11-21	Verfahren zur Herstellung von Anthrachinonverbindungen

Publications (1)

Publication Number	Publication Date
CH534713A true CH534713A (de)	1973-03-15

Family

ID=4424758

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1735169A CH534713A (de)	1969-11-21	1969-11-21	Verfahren zur Herstellung von Anthrachinonverbindungen

Country Status (2)

Country	Link
BE (1)	BE759054A (fr)
CH (1)	CH534713A (fr)

0
- BE BE759054D patent/BE759054A/fr unknown
1969
- 1969-11-21 CH CH1735169A patent/CH534713A/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE759054A (fr)	1971-04-30

Legal Events

Date	Code	Title	Description
1975-06-30	PL	Patent ceased

Publication	Publication Date	Title
DE1148341B (de)	1963-05-09	Verfahren zur Herstellung von Farbstoffen
DE2249643A1 (de)	1973-04-19	Nitrodiphenylamino-azo-farbstoffe, ihre herstellung und verwendung
DE1156527B (de)	1963-10-31	Verfahren zur Herstellung von Anthrachinonkuepenfarbstoffen
DE1070313B (de)	1959-12-03	Verfahren zur Herstellung von 1-Amino-4- phenylamino- anthrachinon- 2- sulfonsäuren
CH534713A (de)	1973-03-15	Verfahren zur Herstellung von Anthrachinonverbindungen
DE1066682B (fr)	1959-10-08
DE2423548A1 (de)	1975-11-27	Verfahren zur herstellung von 4-amino1,8-naphthalimid-verbindungen
DE1269266B (de)	1968-05-30	Verfahren zur Herstellung von wasserloeslichen Aminoanthrachinonfarbstoffen
DE2346047C3 (de)	1979-01-25	Blaue anthrachinoide Dispersionsfarbstoffe, deren Herstellung und Verwendung
DE2203460C3 (de)	1980-08-28	Monoazofarbstoffe und Verfahren zum Färben und Bedrucken
DE2902485A1 (de)	1979-07-26	6/7-halogen-anthrachinonverbindungen, deren herstellung und verwendung
CH635123A5 (de)	1983-03-15	Gemisch von 6/7-halogen-anthrachinonverbindungen und deren herstellung.
DE1644659C3 (de)	1976-07-22	Anthrachinonfarbstoffe, ihre Herstellung und deren Verwendung
DE1021970B (de)	1958-01-02	Verfahren zur Herstellung von Anthrachinonfarbstoffen
DE1644545C (de)	1972-07-06	Saure Anthrachinonfarbstoffgemische, deren Herstellung und Verwendung
DE1284539B (de)	1968-12-05	Verfahren zur Herstellung von 1-Amino-anthrachinonfarbstoffen
DE1644543C (de)	1973-04-19	Saure Anthrachinonfarbstoffe, deren Herstellung und Verwendung
DE2359411C3 (de)	1978-09-28	Sulfonsäuregruppenhaltige Anthrachinonfarbstoffe, deren Herstellung und deren Verwendung
DE1644334C3 (de)	1976-07-29	26.07.65 Schweiz 10436-65 Verfahren zum Färben, Klotzen oder Bedrucken von Textilien, die aus Acrylnitrilpolymerisaten oder -mischpolymerisaten oder durch saure Gruppen modifizierten Polyester- oder Polyoleflnfasern bestehen bzw. solche enthalten
AT234872B (de)	1964-07-27	Verfahren zur Herstellung neuer Küpenfarbstoffe
AT235431B (de)	1964-08-25	Verfahren zur Herstellung von neuen organischen Reaktivfarbstoffen
DE1644659B2 (de)	1975-12-18	Anthrachinonfarbstoffe, ihre Herstellung und deren Verwendung
DE2531557A1 (de)	1977-02-03	Anthrachinonfarbstoffe
CH507343A (de)	1971-05-15	Verfahren zur Herstellung von Anthrachinonfarbstoffen
DE1917051A1 (de)	1970-05-27	Anthrachinonverbindungen