US2228317A - Process of producing dyeings fast to washing on cellulose esters and ethers and the dyed fiber obtained thereby - Google Patents

Process of producing dyeings fast to washing on cellulose esters and ethers and the dyed fiber obtained thereby Download PDF

Info

Publication number: US2228317A
Authority: US; United States
Prior art keywords: cellulose esters; ethers; fiber; washing; dyed
Prior art date: 1938-02-18
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 - Lifetime

Application number

US255865A

Other languages

English (en)

Inventor

Kirst Werner

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.)

GAF Chemicals Corp

Original Assignee

General Aniline and Film Corp

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.)

1938-02-18

Filing date

1939-02-11

Publication date

1941-01-14

1939-02-11 Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp

1941-01-14 Application granted granted Critical

1941-01-14 Publication of US2228317A publication Critical patent/US2228317A/en

1958-01-14 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000835 fiber Substances 0.000 title description 24
229920002678 cellulose Polymers 0.000 title description 22
238000000034 method Methods 0.000 title description 21
238000004043 dyeing Methods 0.000 title description 14
229920003086 cellulose ether Polymers 0.000 title description 11
150000002170 ethers Chemical class 0.000 title description 10
238000005406 washing Methods 0.000 title description 5
QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 15
238000010168 coupling process Methods 0.000 description 12
238000005859 coupling reaction Methods 0.000 description 12
230000008878 coupling Effects 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 5
239000002657 fibrous material Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000001624 naphthyl group Chemical group 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
235000010980 cellulose Nutrition 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000006193 diazotization reaction Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 2
229940081735 acetylcellulose Drugs 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002301 cellulose acetate Polymers 0.000 description 2
150000008049 diazo compounds Chemical class 0.000 description 2
239000000975 dye Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000004744 fabric Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
230000003472 neutralizing effect Effects 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000002699 waste material Substances 0.000 description 2
210000002268 wool Anatomy 0.000 description 2
FSBRKZMSECKELY-UHFFFAOYSA-N 5-aminonaphthalen-2-ol Chemical compound OC1=CC=C2C(N)=CC=CC2=C1 FSBRKZMSECKELY-UHFFFAOYSA-N 0.000 description 1
229920002955 Art silk Polymers 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
-1 aminonaphthol compound Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
125000000542 sulfonic acid group Chemical group 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
- C09B37/00—Azo dyes prepared by coupling the diazotised amine with itself

Definitions

the present invention relates to a process of producing dyeings fast to washing on cellulose esters and ethers and to the dyed fiber obtained thereby.
fast dyeings may be produced on cellulose esters and ethers, by applying to this material an organic compound containing an amino group capable of being diazotized, then diazotizing the compound on the fiber and developing it to the azo-dyestuff by treatment with a coupling component, for instance, p-naphthol.
a coupling component for instance, p-naphthol.
This invention relates to the production of dyeings fast to washing on cellulose esters or ethers in a much simpler manner by applying to the cellulose ester or ether or dissolving therein an aminonaphthol or a nuclear substitution product thereof, for instance a substitution product containing one or more alkyl groups or halogen atoms, which has in the naphthalene ring at least one free position capable of coupling with diazo-compounds, then diazotizing the aminonaphthol or derivative thereof and causing it to combine with itself by a treatment with an agent neutralizing the acid or having an alkaline action.
the combination may be brought about by adding to the diazo-bath an agent neutralizing the acid or having an alkaline action, after the diazotization isfinished, or by passing the diazotized goods through a bath containing one of the said agents.
aminonaphthol of the composition indicated above in the form of a dispersed paste or an alkali salt or an acid salt the aminon-aphthol being adsorbed practically only on the cellulose ester or ether; the aminonaphthol compound is then diazotized on the fiber and the dyeing developed by self-coupling.
the aminonaphthols may be applied to the fiber in an acid, neutral or alkaline solution.
the diazotization is performed with the usual agents; the coupling may be brought about by means of an inorganic base, an inorganic or organic salt of alkaline action or an organic base of alkaline action.
1 kilo of acetate silk is treated for about 1 hour at about 80 C. in a bath containing 50 grams of the sodium salt of 1-amino-.6-naphthol, if desired, in the presence of a. protective colloid, for instance, sulfite cellulose waste liquor or oleylmethyltaur'ine per 30 liters of liquor, rinsed, diazotized in the cold with a solution of 75 grams of sodium nitrite and 150 cc. of hydrochloric acid of 2 B. per 30 liters of water, centrifuged and developed in a cold bath containing per 30 liters of water 80 cc. of ammonia of 25 per cent strength. A black dyeing of very good f-astness to water and washing is obtained.
a protective colloid for instance, sulfite cellulose waste liquor or oleylmethyltaur'ine per 30 liters of liquor
diazotized in the cold with a solution of 75 grams of sodium
the material is then rinsed, diazotized for /g hour in the cold with a solution of 75 grams of sodium nitrite and 150 cc. of hydrochloric acid of 20 B. with addition of 500 grams of sodium sulfate in 30 liters of water, squeezed and developed at ordinary temperature with 120 cc. of ammonia of 25 per cent strength per 30 liters of Water. A black dyeing is obtained,
Iclaim 1. The process which comprises applying to fibrous materialof the group consisting oi! cellulose esters and ethers an aminonaphthol which has in the naphthalene ring at least one free po- 'sition capable of coupling .with diam-compounds,
Fibrous material oi the group consisting of cellulose esters. and ethers dyed with an azocompound obtainable on the fiber by the process claimed in claim 1.
Fibrous material of the group consisting of cellulose esters and ethers dyed with an azo-' compounds obtainable on the fiber by the process claimed in claim 3.

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)

US255865A 1938-02-18 1939-02-11 Process of producing dyeings fast to washing on cellulose esters and ethers and the dyed fiber obtained thereby Expired - Lifetime US2228317A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEI60577D DE711328C (de)	1938-02-18	1938-02-18	Verfahren zur Herstellung von Azofarbstoffen auf Celluloseestern und -aethern oder diese enthaltenden Faserstoffen

Publications (1)

Publication Number	Publication Date
US2228317A true US2228317A (en)	1941-01-14

Family

ID=7195279

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US255865A Expired - Lifetime US2228317A (en)	1938-02-18	1939-02-11	Process of producing dyeings fast to washing on cellulose esters and ethers and the dyed fiber obtained thereby

Country Status (3)

Country	Link
US (1)	US2228317A (fr)
DE (1)	DE711328C (fr)
FR (1)	FR850502A (fr)

1938
- 1938-02-18 DE DEI60577D patent/DE711328C/de not_active Expired
1939
- 1939-02-11 US US255865A patent/US2228317A/en not_active Expired - Lifetime
- 1939-02-18 FR FR850502D patent/FR850502A/fr not_active Expired

Also Published As

Publication number	Publication date
DE711328C (de)	1941-09-30
FR850502A (fr)	1939-12-19

Publication	Publication Date	Title
US2670265A (en)	1954-02-23	Process
US2192127A (en)	1940-02-27	Process of producing fast dyeings
US2078388A (en)	1937-04-27	Dyeing process and composition
US2243213A (en)	1941-05-27	Process of producting fast dyeings on cellulose esters and ethers and the dyed fiber obtained thereby
US2277551A (en)	1942-03-24	Process of producing fast dyeings and the dyed fiber obtained thereby
GB745641A (en)	1956-02-29	Manufacture of cobaltiferous and chromiferous azo-dyestuffs
US2643175A (en)	1953-06-23	Treatment with alcoholic solution to complete coupling of azo dyes in cellulose acetate textile material
US2203305A (en)	1940-06-04	Process of dyeing
US2263559A (en)	1941-11-25	Process of producing fast dyeings and the dyed fiber obtained thereby
US1600277A (en)	1926-09-21	Dyeing of cellulose acetate
US2178744A (en)	1939-11-07	Coloration of textile materials
US2169970A (en)	1939-08-15	Disazo dyestuffs
US2213193A (en)	1940-09-03	Process of producing fast dyeings
US2094770A (en)	1937-10-05	Dyeing of organic derivatives of cellulose
US1483797A (en)	1924-02-12	Dyeing and printing acetyl silk and materials containing it
US2112864A (en)	1938-04-05	Process for producing fast dyeings on the fiber
US2137810A (en)	1938-11-22	Direct dyes, process, and product
US2321816A (en)	1943-06-15	Process of producing fast dyeings on fibrous materials
US2518153A (en)	1950-08-08	Dyeing of cellulose esters with reduced vat dyes in alcoholic solution
US1958307A (en)	1934-05-08	Process relating to the dyeing of wool
US2211149A (en)	1940-08-13	Process for the production of azo dyestuffs on the fiber
US2144578A (en)	1939-01-17	Process for producing fast dyeings on the fiber
GB1117938A (en)	1968-06-26	New disazo dyestuffs containing a di(cyanoethyl) group and their application to the dyeing of synthetic fibres
US2938762A (en)	1960-05-31	Diazotization in presence of developer
US2275124A (en)	1942-03-03	Azo dye