ES248558A1 - New anthraquinone dyestuffs and their manufacture and use - Google Patents
New anthraquinone dyestuffs and their manufacture and useInfo
- Publication number
- ES248558A1 ES248558A1 ES0248558A ES248558A ES248558A1 ES 248558 A1 ES248558 A1 ES 248558A1 ES 0248558 A ES0248558 A ES 0248558A ES 248558 A ES248558 A ES 248558A ES 248558 A1 ES248558 A1 ES 248558A1
- Authority
- ES
- Spain
- Prior art keywords
- nitro
- benzene
- group
- sulphonic acid
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 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 title 1
- 150000004056 anthraquinones Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 3
- CULMSARXGDSDNE-UHFFFAOYSA-N 1-methyl-4-nitrobenzene;sulfuryl dichloride Chemical class ClS(Cl)(=O)=O.CC1=CC=C([N+]([O-])=O)C=C1 CULMSARXGDSDNE-UHFFFAOYSA-N 0.000 abstract 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- 229940117927 ethylene oxide Drugs 0.000 abstract 2
- 239000002657 fibrous material Substances 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- GIKMWFAAEIACRF-UHFFFAOYSA-N 2,4,5-trichloropyrimidine Chemical compound ClC1=NC=C(Cl)C(Cl)=N1 GIKMWFAAEIACRF-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- BRKFTWHPLMMNHF-UHFFFAOYSA-N 5-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C=C1S(O)(=O)=O BRKFTWHPLMMNHF-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000397 acetylating effect Effects 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- -1 dichlorotriazinylamino Chemical group 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
- 239000012991 xanthate Substances 0.000 abstract 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/004—Anthracene dyes
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
- D01F2/08—Composition of the spinning solution or the bath
- D01F2/16—Addition of dyes to the spinning solution
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
In Example 8, a dyestuff obtained by condensing in equimolecular proportions 1-amino-benzene -3-sulphonic acid, cyanuric chloride and a compound of the formula <FORM:0912372/IV(a)/1> dissolved in a viscose-xanthate solution is spun to form a filament.ALSO:3-aminobenzene-sulphonic acid N-(31-acetylamino-41-sulpho-phenyl)amide and the corresponding compounds containing chlorine or a methyl group in the 6-position are made by condensing 2:4-diamino-benzene sulphonic acid with 3-nitro-, 3-nitro-6-chloro- or 3-nitro-6-methyl-benzene sulphonyl chlorides respectively, acetylating the nitro compounds obtained and reducing the nitro groups. 3-amino-6-methyl-benzene sulphonic acid N - (51 - acetylamino-21-sulphophenyl)-amide is made by condensing 3-nitro-6-methyl-benzene sulphonyl chloride with 2-amino-4-acetylaminobenzene sulphonic acid and reducing the nitro group. An ethylene-oxide addition product is made by heating a commercial octadecenylamine with disintegrated sodium and ethylene oxide.ALSO:The invention comprises water-soluble dyestuffs of the formula- <FORM:0912372/IV (b)/1> wherein Z is hydrogen or sulphonic acid, n and m are each whole numbers, R is a benzene residue, R1 is a benzene residue or an alkylene bridge, X is -CO- or -SO2-and Y is an acylated amino group in which the acyl group is known to be capable of entering into chemical combination with cellulosic fibrous material. Specified acyl radicals are those derived from acrylic, a -chloracrylic, a - or b -chloro-b -carboxy-acrylic, propiolic, chloracetic, sulphochloracetic, a - and b -chloro- and b -bromo-propionic and a :b -dichloropropionic acids and those derived from cyanuric chloride or trichloropyrimidine such as residues of the formula <FORM:0912372/IV (b)/2> where X is a substituted or unsubstituted amino group or a substituted hydroxyl group, e.g. an ether group. The dyestuffs are made by acylating a compound of the formula (1) above where Z, R, R1, X, m and n are as above but Y is an acylatable amino group with the anhydride or halide of an acid whose acyl group is known to be capable of entering into chemical combination with cellulosic fibrous material. When cyanuric chloride is the acylating agent, the dichlorotriazinylamino product formed may be further condensed with ammonia, an amine, an alcohol or a phenol. The dyestuffs dye and print wool, superpolyamides, leather and silk from an acid to neutral bath, and cellulosic materials from an alkaline bath or in conjunction with a treatment with an p acidbinding agent at raised temperature in reddish-blue shades. Specifications 781,930, 784,221, 798,121, 803,473, 822,047, 826,375, 831,371, 832,400, 846,765, 848,742, 852,911, 857,186, 858,184, 867,571, 868,492, 885,814 and 885,815 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5762458A CH367916A (en) | 1958-03-28 | 1958-03-28 | Process for the production of new dyes of the anthraquinone series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES248558A1 true ES248558A1 (en) | 1960-01-01 |
Family
ID=4521224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0248558A Expired ES248558A1 (en) | 1958-03-28 | 1959-03-26 | New anthraquinone dyestuffs and their manufacture and use |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH367916A (en) |
| ES (1) | ES248558A1 (en) |
| GB (1) | GB912372A (en) |
| NL (2) | NL122024C (en) |
-
0
- NL NL237560D patent/NL237560A/xx unknown
-
1958
- 1958-03-28 CH CH5762458A patent/CH367916A/en unknown
-
1959
- 1959-03-26 ES ES0248558A patent/ES248558A1/en not_active Expired
- 1959-03-26 GB GB1068759A patent/GB912372A/en not_active Expired
- 1959-03-26 NL NL237560A patent/NL122024C/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| NL237560A (en) | 1966-11-15 |
| NL122024C (en) | 1967-03-16 |
| GB912372A (en) | 1962-12-05 |
| CH367916A (en) | 1963-03-15 |
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