GB669590A - Improvements in or relating to a process for improving the whiteness of colour materials - Google Patents
Improvements in or relating to a process for improving the whiteness of colour materialsInfo
- Publication number
- GB669590A GB669590A GB15009/49A GB1500949A GB669590A GB 669590 A GB669590 A GB 669590A GB 15009/49 A GB15009/49 A GB 15009/49A GB 1500949 A GB1500949 A GB 1500949A GB 669590 A GB669590 A GB 669590A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphophenyl
- compounds
- substituted
- tolyl
- methoxyphenyl
- 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
- 239000000463 material Substances 0.000 title abstract 5
- 238000000034 method Methods 0.000 title abstract 2
- -1 pyrazoline compound Chemical class 0.000 abstract 41
- 150000001875 compounds Chemical class 0.000 abstract 17
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 9
- OFCFYWOKHPOXKF-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-chlorobenzene Chemical group C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=CC=C1 OFCFYWOKHPOXKF-UHFFFAOYSA-N 0.000 abstract 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract 6
- 125000002541 furyl group Chemical group 0.000 abstract 6
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 abstract 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 229920002994 synthetic fiber Polymers 0.000 abstract 5
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 239000004952 Polyamide Substances 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 230000001476 alcoholic effect Effects 0.000 abstract 3
- 150000001735 carboxylic acids Chemical class 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 230000002349 favourable effect Effects 0.000 abstract 3
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 229920002647 polyamide Polymers 0.000 abstract 3
- 102000004169 proteins and genes Human genes 0.000 abstract 3
- 108090000623 proteins and genes Proteins 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- 238000005266 casting Methods 0.000 abstract 2
- 229920002301 cellulose acetate Polymers 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D10/00—Physical treatment of artificial filaments or the like during manufacture, i.e. during a continuous production process before the filaments have been collected
-
- 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
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/10—Other agents for modifying properties
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
- G03C1/8155—Organic compounds therefor
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M8/00—Fuel cells; Manufacture thereof
- H01M8/04—Auxiliary arrangements, e.g. for control of pressure or for circulation of fluids
- H01M8/04276—Arrangements for managing the electrolyte stream, e.g. heat exchange
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Sustainable Energy (AREA)
- Electrochemistry (AREA)
- Mechanical Engineering (AREA)
- Coloring (AREA)
- Artificial Filaments (AREA)
- Paper (AREA)
Abstract
Natural and artificial fibres and films are brightened by the application of a fluorescent pyrazoline compound of the general formula <FORM:0669590/IV (a)/1> in which R1 is hydrogen, a furyl residue or an unsubstituted or substituted hydrocarbon group but excluding nitro-substituted groups, Ar1 is an unsubstituted or substituted aromatic hydrocarbon residue but excluding such residues containing sulphonic, carboxylic, nitro or cyano groups, and Ar2 is an unsubstituted or substituted aromatic hydrocarbon residue but excluding nitro-substituted residues, which compound is colourless in aqueous or alcoholic solution. Particularly favourable are compounds in which R1 or Ar2 contain carboxylic or sulphonic acid groups which in the form of their salts are substantive to the fibres and films and as free acids are substantive to protein and polyamide fibres. Many compounds falling within the general formula given are specified, including compounds in which R1 or Ar2 is phenyl, m-tolyl, methyl, p-chlorophenyl-phenyl, p-methoxyphenyl, p-sulphophenyl, p-chlorophenyl, m-sulphophenyl, p-methyl-m-sulphophenyl, p-methyl-o-sulphophenyl, 4-sulpho-2, 5-dichlorophenyl-4, 8-disulphonaphthyl, o-sulphophenyl, p-acetamidophenyl or furyl, and in which Ar1 is phenyl, m-tolyl, p-bromophenyl, p-tolyl, p-methoxyphenyl, p-ethoxyphenyl, p-phenoxyphenyl, p-phenylphenyl, p-ethoxy-m-methylphenyl, p-chlorophenylphenyl, p-methoxyphenyl or p-chlorophenyl. The compounds may be applied to white materials to improve the whiteness, or to dyed materials to improve the colour. In the case of artificial fibres and films, the compounds may be applied at any stage, e.g. they may be incorporated in cellulose acetate compositions before extruding or casting.ALSO:Natural and artificial fibres and films are brightened by the application of a fluorescent pyrazoline compound of the general formula <FORM:0669590/IV (b)/1> in which R1 is hydrogen, a furyl residue or an unsubstituted or substituted hydrocarbon group but excluding nitro-substituted groups, Ar1 is an unsubstituted or substituted aromatic hydrocarbon residue but excluding such residues containing sulphonic, carboxylic, nitro or cyano groups, and Ar2 is an unsubstituted or substituted aromatic hydrocarbon residue, but excluding nitro-substituted residues, which compound is colourless in aqueous or alcoholic solution. Particularly favourable are compounds in which R1 or Ar2 contain carboxylic or sulphonic acid groups which in the form of their salts are substantive to the fibres and films and as free acids are substantive to protein and polyamide fibres. Many compounds falling within the general formula given are specified, including compounds in which R1 or Ar2 is phenyl, m-tolyl, methyl, p-chlorophenylphenyl, p-methoxyphenyl, p-sulphophenyl, p-chlorophenyl, m-sulphophenyl, p - methyl - m - sulphophenyl, p-methyl-o-sulphophenyl, 4-sulpho-2,5-dichlorophenyl, 4,8-disulphonaphthyl, o-sulphophenyl, p-acetamidophenyl or furyl, and in which Ar is phenyl, m-tolyl, p-bromophenyl, p-tolyl, p-methoxyphenyl, p-ethoxyphenyl, p-phenoxyphenyl, p-phenylphenyl, p-ethoxy-m-methylphenyl, p - chlorophenylphenyl, p - methoxyphenyl or p-chlorophenyl. The compounds may be prepared by the process of Specification 669,591; by the condensation of an aryl hydrazine with a reaction product obtained from an acetophenone, formaldehyde and an amine; or by the condensation of a ketone of the type Ar-CO-CR=CH2 with an aryl hydrazine.ALSO:Natural and artificial fibres and films are brightened by the application of a fluorescent pyrazoline compound of the general formula <FORM:0669590/IV (c)/1> in which R1 is hydrogen, a furyl residue or an unsubstituted or substituted hydrocarbon group but excluding nitro-substituted groups, Ar1 is an unsubstituted or substituted aromatic hydrocarbon residue but excluding such residues containing sulphonic, carboxylic, nitro or cyano groups, and Ar2 is an unsubstituted or substituted aromatic hydrocarbon residue but excluding nitro-substituted residues, which compound is colourless in aqueous or alcoholic solution. Particularly favourable are compounds in which R1 or Ar2 contains carboxylic or sulphonic acid groups, which in the form of their salts are substantive to the fibres and films and as free acids are substantive to protein and polyamide fibres. Many compounds falling within the general formula given are specified, including compounds in which R1 or Ar2 is phenyl, m-tolyl, methyl, p-chlorophenylphenyl, p-methoxyphenyl, p-sulphophenyl, p-chlorophenyl, m-sulphophenyl, p - methyl - m - sulphophenyl, p - methyl - o - sulphophenyl, 4 - sulpho - 2,5 - dichlorophenyl, 4,8 - disulphonaphthyl, o - sulphophenyl, p-acetamidophenyl or furyl, and in which Ar1 is phenyl, m-tolyl, p-bromophenyl, p - tolyl, p - methoxyphenyl, p - ethoxyphenyl, p - phenoxyphenyl, p - phenylphenyl, p - ethoxy - m - methylphenyl, p - chlorophenylphenyl, p-methoxyphenyl or p-chlorophenyl. The compounds may be applied to white materials to improve the whiteness, or to dyed materials to improve the colour. In the case of artificial fibres and films, the compounds may be applied at any stage, e.g. they may be incorporated in cellulose acetate compositions before extruding or casting.
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB15009/49A GB669590A (en) | 1949-06-03 | 1949-06-03 | Improvements in or relating to a process for improving the whiteness of colour materials |
US165116A US2639990A (en) | 1949-06-03 | 1950-05-29 | Process for improving the whiteness or color of materials and products resulting therefrom |
NL153852A NL79254C (en) | 1949-06-03 | 1950-05-30 | |
FR1021379D FR1021379A (en) | 1949-06-03 | 1950-06-02 | Process for improving fibers and films and products obtained by this process |
CH288169D CH288169A (en) | 1949-06-03 | 1950-06-03 | Process for the preparation of an optical brightening agent. |
DEI1016A DE966411C (en) | 1949-06-03 | 1950-06-03 | Methods for improving the optical properties of fibers and films |
CH308746D CH308746A (en) | 1949-06-03 | 1952-08-25 | Process for the preparation of an optical brightening agent. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB15009/49A GB669590A (en) | 1949-06-03 | 1949-06-03 | Improvements in or relating to a process for improving the whiteness of colour materials |
Publications (1)
Publication Number | Publication Date |
---|---|
GB669590A true GB669590A (en) | 1952-04-02 |
Family
ID=10051454
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB15009/49A Expired GB669590A (en) | 1949-06-03 | 1949-06-03 | Improvements in or relating to a process for improving the whiteness of colour materials |
Country Status (6)
Country | Link |
---|---|
US (1) | US2639990A (en) |
CH (2) | CH288169A (en) |
DE (1) | DE966411C (en) |
FR (1) | FR1021379A (en) |
GB (1) | GB669590A (en) |
NL (1) | NL79254C (en) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3133080A (en) * | 1964-05-12 | Optical whitening agents of the | ||
US3141879A (en) * | 1964-07-21 | Chj-chz | ||
US2837485A (en) * | 1958-06-03 | Ari-ch | ||
US2785133A (en) * | 1954-03-26 | 1957-03-12 | Gen Aniline & Film Corp | Compositions for a method of whitening fine fabrics |
US2938292A (en) * | 1955-08-18 | 1960-05-31 | Ultra Violet Products Inc | Fingerprinting system |
DE1104483B (en) * | 1955-10-10 | 1961-04-13 | Bayer Ag | Whitening agents |
US2983604A (en) * | 1955-11-03 | 1961-05-09 | Gen Aniline & Film Corp | Quenching solution for fluorescent photographic paper employed in the manufacture ofhalftone negatives |
BE568156A (en) * | 1957-06-06 | |||
DE1157193B (en) * | 1957-10-30 | 1963-11-14 | Unilever Nv | Lightening of textiles |
US3181949A (en) * | 1958-06-02 | 1965-05-04 | Gevaert Photo Prod Nv | Light sensitive elements having optical bleaching compositions coated thereon |
US3181948A (en) * | 1958-06-02 | 1965-05-04 | Gevaert Photo Prod Nv | Method for optical bleaching of coated papers and resultant product |
NL242152A (en) * | 1958-08-09 | |||
BE581861A (en) * | 1958-08-20 | |||
BE581862A (en) * | 1958-08-22 | |||
US2985593A (en) * | 1958-09-26 | 1961-05-23 | Borden Co | Scintillator composition |
US3131079A (en) * | 1960-08-12 | 1964-04-28 | Bayer Ag | Brightening of fiber material by coating with 1, 3-diaryl- and 1, 3, 5-triaryl pyrazoline derivatives |
NL290832A (en) * | 1962-03-31 | |||
DE1419329B1 (en) * | 1962-04-21 | 1970-01-15 | Hoechst Ag | 1,3-diaryl-delta-pyrazoline compounds and their use as whitening agents |
US3434837A (en) * | 1964-06-05 | 1969-03-25 | Eastman Kodak Co | Photographic element |
GB1086068A (en) * | 1964-09-02 | 1967-10-04 | Ici Ltd | Process for the whitening of polymeric materials and nitrogen-containing polycyclic compounds for use therein |
DE1469222B1 (en) * | 1964-09-25 | 1972-03-09 | Hoechst Ag | Pyrazoline derivatives and their preparation and use |
DE1286897B (en) * | 1965-10-27 | 1969-01-09 | Kalle Ag | Two component diazotype material |
CH475255A (en) * | 1966-12-23 | 1969-07-15 | Geigy Ag J R | Process for the preparation of pyrazoline sulfonic acid esters |
US3754964A (en) * | 1971-02-26 | 1973-08-28 | Ciba Geigy Corp | Process for the continuous optical brightening of acylated cellulose fibre material |
US4595458A (en) * | 1985-05-17 | 1986-06-17 | Olin Corporation | Process for using selected fatty acid adducts of a 1,2,4-triazole as sizing or waterproofing agents for cellulosic materials |
IE59813B1 (en) * | 1986-05-09 | 1994-04-06 | Warner Lambert Co | Styryl pyrazoles, isoxazoles and analogs thereof having activity as 5-lipoxy-genase inhibitors and pharmaceutical compositions containing them |
EP0915370B1 (en) * | 1997-11-04 | 2002-03-13 | Konica Corporation | Silver halide light-sensitive photographic material |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2153615A (en) * | 1936-10-23 | 1939-04-11 | Du Pont | 1-aryl-5-pyrazolone-3-carboxylic acids |
FR878823A (en) * | 1941-02-18 | 1943-02-04 | Ig Farbenindustrie Ag | Process for emphasizing whites and the luminous power of the surface color of photographic images |
DE735478C (en) * | 1941-07-12 | 1943-05-18 | Ig Farbenindustrie Ag | Process for the preparation of 4,5-Diarylimidazolineabkoemmlingen |
GB566810A (en) * | 1943-05-20 | 1945-01-15 | Unilever Ltd | Method of and preparations for improving the whiteness of materials |
GB584435A (en) * | 1944-03-01 | 1947-01-15 | Unilever Ltd | Improvements in the laundering of white textile articles |
-
1949
- 1949-06-03 GB GB15009/49A patent/GB669590A/en not_active Expired
-
1950
- 1950-05-29 US US165116A patent/US2639990A/en not_active Expired - Lifetime
- 1950-05-30 NL NL153852A patent/NL79254C/xx active
- 1950-06-02 FR FR1021379D patent/FR1021379A/en not_active Expired
- 1950-06-03 CH CH288169D patent/CH288169A/en unknown
- 1950-06-03 DE DEI1016A patent/DE966411C/en not_active Expired
-
1952
- 1952-08-25 CH CH308746D patent/CH308746A/en unknown
Also Published As
Publication number | Publication date |
---|---|
CH308746A (en) | 1955-07-31 |
CH288169A (en) | 1953-01-15 |
FR1021379A (en) | 1953-02-18 |
US2639990A (en) | 1953-05-26 |
NL79254C (en) | 1955-10-15 |
DE966411C (en) | 1957-08-01 |
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