CS214844B2 - Method of making the dyes reacting to the celullose - Google Patents

Method of making the dyes reacting to the celullose Download PDF

Info

Publication number: CS214844B2
Authority: CS; Czechoslovakia
Prior art keywords: honors; methyl; dyes; hydrogen; formula
Prior art date: 1979-10-12

Application number

CS806832A

Other languages

Czech (cs)

English (en)

Inventor

Herbert F Andrew

Clive H Barlow

Original Assignee

Ici Ltd

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.)

1979-10-12

Filing date

1980-10-09

Publication date

1982-06-25

1980-10-09 Application filed by Ici Ltd filed Critical Ici Ltd

1982-06-25 Publication of CS214844B2 publication Critical patent/CS214844B2/cs

Links

239000000975 dye Substances 0.000 title abstract description 22
238000004519 manufacturing process Methods 0.000 title description 2
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
239000002253 acid Substances 0.000 claims abstract description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 9
229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
239000000985 reactive dye Substances 0.000 claims abstract description 8
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 5
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 4
125000004427 diamine group Chemical group 0.000 claims 1
150000003918 triazines Chemical class 0.000 claims 1
-1 ammonium radical Chemical class 0.000 abstract description 8
229920002678 cellulose Polymers 0.000 abstract description 5
239000001913 cellulose Substances 0.000 abstract description 5
238000005406 washing Methods 0.000 abstract description 2
229910006069 SO3H Inorganic materials 0.000 abstract 2
125000000896 monocarboxylic acid group Chemical group 0.000 abstract 2
PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
239000000463 material Substances 0.000 description 7
238000004043 dyeing Methods 0.000 description 4
239000004753 textile Substances 0.000 description 4
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical group NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
150000003254 radicals Chemical group 0.000 description 3
125000004306 triazinyl group Chemical group 0.000 description 3
VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000000370 acceptor Substances 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
238000003892 spreading Methods 0.000 description 2
ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 1
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
UMAPFAAAQBMYNJ-UHFFFAOYSA-N 1-n,2-n-dimethylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1NC UMAPFAAAQBMYNJ-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
RPKCLSMBVQLWIN-UHFFFAOYSA-N 2-n-methylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1N RPKCLSMBVQLWIN-UHFFFAOYSA-N 0.000 description 1
229940061334 2-phenylphenol Drugs 0.000 description 1
FKSRSWQTEJTBMI-UHFFFAOYSA-N 3,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1N FKSRSWQTEJTBMI-UHFFFAOYSA-N 0.000 description 1
MHQULXYNBKWNDF-UHFFFAOYSA-N 3,4-dimethylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1C MHQULXYNBKWNDF-UHFFFAOYSA-N 0.000 description 1
AXNUJYHFQHQZBE-UHFFFAOYSA-N 3-methylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N)=C1N AXNUJYHFQHQZBE-UHFFFAOYSA-N 0.000 description 1
XSZYBMMYQCYIPC-UHFFFAOYSA-N 4,5-dimethyl-1,2-phenylenediamine Chemical compound CC1=CC(N)=C(N)C=C1C XSZYBMMYQCYIPC-UHFFFAOYSA-N 0.000 description 1
AGAHETWGCFCMDK-UHFFFAOYSA-N 4-methoxybenzene-1,2-diamine Chemical compound COC1=CC=C(N)C(N)=C1 AGAHETWGCFCMDK-UHFFFAOYSA-N 0.000 description 1
DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
HKTWHHAJDJCUPC-UHFFFAOYSA-N 7-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 HKTWHHAJDJCUPC-UHFFFAOYSA-N 0.000 description 1
GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
239000004115 Sodium Silicate Substances 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000004984 aromatic diamines Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
239000002585 base Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 description 1
PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
150000005002 naphthylamines Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
150000004987 o-phenylenediamines Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000010292 orthophenyl phenol Nutrition 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000005628 tolylene group Chemical group 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
210000002268 wool Anatomy 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/043—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring containing two or more triazine rings linked together by a non-chromophoric link
- 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
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/09—Disazo or polyazo dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

CS806832A 1979-10-12 1980-10-09 Method of making the dyes reacting to the celullose CS214844B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7935503		1979-10-12

Publications (1)

Publication Number	Publication Date
CS214844B2 true CS214844B2 (en)	1982-06-25

Family

ID=10508468

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS806832A CS214844B2 (en)	1979-10-12	1980-10-09	Method of making the dyes reacting to the celullose

Country Status (10)

Country	Link
JP (1)	JPS5661459A (fr)
AU (1)	AU6150080A (fr)
BE (1)	BE885648A (fr)
CS (1)	CS214844B2 (fr)
DE (1)	DE3033764A1 (fr)
ES (1)	ES494883A0 (fr)
FR (1)	FR2467230A1 (fr)
IT (1)	IT1132704B (fr)
NL (1)	NL8004866A (fr)
ZA (1)	ZA805007B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0723586B2 (ja) *	1984-02-20	1995-03-15	住友化学工業株式会社	セルロ−ス系繊維材料の染色法
JPH0723587B2 (ja) *	1984-02-21	1995-03-15	住友化学工業株式会社	セルロ−ス系繊維材料の染色方法
JPH066676B2 (ja) *	1985-07-09	1994-01-26	日本化薬株式会社	アゾ化合物及びそれを用いる染色法
JP2572335B2 (ja) *	1992-10-30	1997-01-16	住友化学工業株式会社	セルロース系繊維材料の染色方法
GB0319234D0 (en) *	2003-08-15	2003-09-17	Dystar Textilfarben Gmbh & Co	Fibre reactive azo dyes

1980
- 1980-08-14 ZA ZA00805007A patent/ZA805007B/xx unknown
- 1980-08-15 AU AU61500/80A patent/AU6150080A/en not_active Abandoned
- 1980-08-28 NL NL8004866A patent/NL8004866A/nl not_active Application Discontinuation
- 1980-09-08 IT IT24534/80A patent/IT1132704B/it active
- 1980-09-08 ES ES494883A patent/ES494883A0/es active Granted
- 1980-09-08 DE DE19803033764 patent/DE3033764A1/de not_active Withdrawn
- 1980-10-09 CS CS806832A patent/CS214844B2/cs unknown
- 1980-10-10 FR FR8021754A patent/FR2467230A1/fr active Pending
- 1980-10-10 BE BE0/202421A patent/BE885648A/fr unknown
- 1980-10-13 JP JP14215480A patent/JPS5661459A/ja active Pending

Also Published As

Publication number	Publication date
ES8106751A1 (es)	1981-09-01
BE885648A (fr)	1981-04-10
JPS5661459A (en)	1981-05-26
AU6150080A (en)	1981-04-16
DE3033764A1 (de)	1981-04-23
ES494883A0 (es)	1981-09-01
IT8024534A0 (it)	1980-09-08
ZA805007B (en)	1981-08-26
FR2467230A1 (fr)	1981-04-17
NL8004866A (nl)	1981-04-14
IT1132704B (it)	1986-07-02

Publication	Publication Date	Title
SK279233B6 (sk)	1998-08-05	Azofarbivá, spôsob ich výroby a ich použitie na fa
US4670547A (en)	1987-06-02	Tetrakisazo compounds having two 1-hydroxy-3- or 4-sulfo-6- or 7-amino- or substituted amino-naphthalene coupling component radicals the amino or substituted amino groups of which are linked 1,3,5-triazine rings
JPH0529659B2 (fr)	1993-05-06
JPH0251565A (ja)	1990-02-21	アゾ染料
CS214844B2 (en)	1982-06-25	Method of making the dyes reacting to the celullose
CS222247B2 (en)	1983-05-27	Method of making the dyes reacting to the cellulose
JPH0218707B2 (fr)	1990-04-26
US5059681A (en)	1991-10-22	Bis-azotriazinyl reactive dyes having an n-alkyl-phenylenediamine link
AU641531B2 (en)	1993-09-23	Nickel phthalocyanine-chlorotriazinyl azo dyes
JPS59115361A (ja)	1984-07-03	水溶性モノアゾ化合物及びこれを用いて染色する方法
EP0692003B1 (fr)	1998-05-27	Colorant reactif mono-azo que
JPH0456036B2 (fr)	1992-09-07
JPS5857464B2 (ja)	1983-12-20	ハンノウセイアゾセンリヨウノセイホウ
JPH0411587B2 (fr)	1992-02-28
JP2000504765A (ja)	2000-04-18	繊維反応性染料
KR100236804B1 (ko)	2000-07-01	섬유-반응성 디스아조 화합물
GB2065159A (en)	1981-06-24	Reactive dyestuffs
US3890257A (en)	1975-06-17	Yellow to orange disazo cationic dyes containing two quaternary ammonium groups
CZ35895A3 (en)	1995-11-15	Water-soluble azo compounds, process of their preparation and their use as dyestuffs
DE2117462A1 (de)	1972-10-26	Disazofarbstoffe
JPH06157931A (ja)	1994-06-07	水溶性ジスアゾ化合物、その製法及び染料としてのその用途
KR101154986B1 (ko)	2012-06-12	반응성 청색 염료 조성물
DE1644270C3 (de)	1975-01-30	Verfahren zur Herstellung von Monoazofarbstoffen
JP2733011B2 (ja)	1998-03-30	水溶性ジスアゾ化合物及びその染料としての用途
PL150526B1 (pl)	1990-06-30	Sposób wytwarzania monoazowych barwników reaktywnych