GB1003083A - Novel 4-alkoxynaphthalimides - Google Patents
Novel 4-alkoxynaphthalimidesInfo
- Publication number
- GB1003083A GB1003083A GB2107/62A GB210762A GB1003083A GB 1003083 A GB1003083 A GB 1003083A GB 2107/62 A GB2107/62 A GB 2107/62A GB 210762 A GB210762 A GB 210762A GB 1003083 A GB1003083 A GB 1003083A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkoxy
- hydrogen
- hydroxyalkyl
- alkyl
- aryl
- 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
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 229910052783 alkali metal Chemical group 0.000 abstract 4
- 150000001340 alkali metals Chemical group 0.000 abstract 4
- 235000013350 formula milk Nutrition 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 125000003282 alkyl amino group Chemical group 0.000 abstract 3
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 238000005282 brightening Methods 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 230000003287 optical effect Effects 0.000 abstract 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 abstract 2
- 239000004952 Polyamide Substances 0.000 abstract 2
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 abstract 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 2
- 239000012954 diazonium Substances 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 2
- 229920002647 polyamide Polymers 0.000 abstract 2
- 229920000728 polyester Polymers 0.000 abstract 2
- 229920002635 polyurethane Polymers 0.000 abstract 2
- 239000004814 polyurethane Substances 0.000 abstract 2
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 2
- 239000004800 polyvinyl chloride Substances 0.000 abstract 2
- 239000005033 polyvinylidene chloride Substances 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- -1 sulpho Chemical group 0.000 abstract 2
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 abstract 1
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 abstract 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 abstract 1
- HBBNWQNDMASDAC-UHFFFAOYSA-N 4-sulfonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(S(O)(=O)=O)C2=C1 HBBNWQNDMASDAC-UHFFFAOYSA-N 0.000 abstract 1
- 244000198134 Agave sisalana Species 0.000 abstract 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 abstract 1
- 240000000491 Corchorus aestuans Species 0.000 abstract 1
- 235000011777 Corchorus aestuans Nutrition 0.000 abstract 1
- 235000010862 Corchorus capsularis Nutrition 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- 229920000297 Rayon Polymers 0.000 abstract 1
- 239000005708 Sodium hypochlorite Substances 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000010425 asbestos Substances 0.000 abstract 1
- 239000007844 bleaching agent Substances 0.000 abstract 1
- 239000001768 carboxy methyl cellulose Substances 0.000 abstract 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 abstract 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 abstract 1
- 210000000085 cashmere Anatomy 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 239000003365 glass fiber Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 210000000050 mohair Anatomy 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 229910052895 riebeckite Inorganic materials 0.000 abstract 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3437—Six-membered rings condensed with carbocyclic rings
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- 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
- D01F1/06—Dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Indole Compounds (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
4-Alkoxynaphthalimides of formula <FORM:1003083/C3/1> where R is C1- 5-alkoxy and R1 is hydrogen alkyl, hydroxyalkyl, aminoalkyl, aralkyl, cycloalkyl, aryl, alkaryl or heterocyclic, the aryl group being optionally substituted by halogen, hydroxyalkyl, alkylamino, alkoxy or -SO3M, where M is hydrogen or an alkali metal are added as optical brightening agents to polyamides, polyesters, polyurethanes, polyvinyl chloride, polyvinylidene chloride, polyacrylonitrile or polyvinyl alcohol.ALSO:The invention comprises compounds of for mula <FORM:1003083/C2/1> where R is C1- 5 alkoxy, and R1 is hydrogen, alkyl, hydroxyalkyl, aminoalkyl, aralkyl, cycloalkyl, aryl, alkaryl or a heterocyclic group, the aryl group being optionally substituted by halogen, hydroxyalkyl, alkylamino, alkoxy or -SO3M, where M is hydrogen or alkali metal. Specified heterocyclic radicals are 2,6-dihalo-5-triazinyl, pyridyl and pyrazolyl. The compounds may be prepared by reacting a 4-alkoxy-1,8-naphthalic acid or its anhydride with a compound R1NH2 or by reacting a compound of formula <FORM:1003083/C2/2> where X is halogen, hydroxy, nitro or sulpho with an alkali metal alcoholate, or where X is hydroxy with a dialkyl sulphate or alkyl halide or where X is amino, converting this to the diazonium salt and reacting this with an alcohol ROH. Alternatively compounds in which R1 is hydrogen can be reacted with alkyl &c. halides to convert R1 into other values. The products are used as optical brightening agents. The diazonium chlorides of a number of 4-aminonaphthalimides are prepared (Example 28). The sodium salts of a number of 4-sulphonaphthalimides are prepared by reacting the sodium salt of 4-sulphonaphthalic acid with methylamine, butylamine, ethanolamine, benzylamine, cyclohexylamine, p-diethylamino-aniline, aniline, 2-ethylhexylamine and 3-dimethylaminopropylamine.ALSO:4-Alkoxynaphthalimides of formula <FORM:1003083/D1-D2/1> where R is C1-5 alkoxy, and R1 is hydrogen, alkyl, hydroxyalkyl, aminoalkyl, aralkyl, cycloalkyl, aryl, alkaryl or a heterocyclic group (particularly 2, 6-dihalo-s-triazinyl), the aryl group being optionally substituted by halogen, hydroxyalkyl, alkylamino, alkoxy, or -SO3M where M is hydrogen or an alkali metal, are used as optical brightening agents for textile materials. Specied are filaments, yarns, threads, and ribbons of cotton, capoc, linen, sisal, jute, wool, mohair, cashmere, asbestos, viscose rayon, cellulose acetate, polyamides, polyesters, polyurethanes, polyvinyl chloride, polyvinylidene chloride, polyacrylonitrile, polyvinyl alcohol and glass fibre. They may be used as aqueous or other solutions or dispersions with or without a dispersing agent. In Example 34, 4-methoxynaphthalimide is incorporated in a sodium hypochlorite bleach solution containing acetic acid and a chlorous dioxide gas generation inhibitor. Other compositions contain surfactant, carboxymethylcellulose, chlorobenzene-type carrier.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP194661 | 1961-01-21 | ||
| JP240561 | 1961-01-26 | ||
| JP240661 | 1961-01-26 | ||
| JP478261 | 1961-02-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1003083A true GB1003083A (en) | 1965-09-02 |
Family
ID=27453513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2107/62A Expired GB1003083A (en) | 1961-01-21 | 1962-01-19 | Novel 4-alkoxynaphthalimides |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE612955A (en) |
| CH (5) | CH427811A (en) |
| DE (1) | DE1445961C3 (en) |
| GB (1) | GB1003083A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1288787B (en) * | 1966-09-08 | 1969-02-06 | Bayer Ag | Polyamide molding compounds with compounds containing imide groups as mold release agents |
| US7714044B2 (en) | 2003-11-14 | 2010-05-11 | Basf Akitengesellschaft | Use of 4-cyano-naphthalene-1, 8-dicarboximide derivatives and related compounds to protect organic material from the damaging effects of light |
| US7875720B2 (en) * | 2000-04-27 | 2011-01-25 | Nalco Company | Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems |
| US8383656B2 (en) | 2009-10-09 | 2013-02-26 | The Ohio State University Research Foundation | Thiazolidinedione energy restriction-mimetic agents |
| US8894881B2 (en) | 2008-01-31 | 2014-11-25 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | 1,8-naphthalimide derivatives as scintillation agents, in particular for discriminating between fast neutrons and gamma rays |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES459497A1 (en) * | 1977-06-04 | 1978-04-16 | Made Labor Sa | N(Aminoalkyl)-naphthalimides and their derivatives |
| DE3618458A1 (en) * | 1986-06-02 | 1987-12-03 | Hoechst Ag | NAPHTHALIMIDES CONTAINING SULFURIC ACID ESTER GROUPS, METHOD FOR THE PRODUCTION AND USE THEREOF |
-
1962
- 1962-01-19 GB GB2107/62A patent/GB1003083A/en not_active Expired
- 1962-01-20 DE DE1445961A patent/DE1445961C3/en not_active Expired
- 1962-01-22 BE BE612955A patent/BE612955A/en unknown
- 1962-01-22 CH CH124363A patent/CH427811A/en unknown
- 1962-01-22 CH CH124163A patent/CH446713A/en unknown
- 1962-01-22 CH CH70962A patent/CH409850A/en unknown
- 1962-01-22 CH CH124263A patent/CH461495A/en unknown
- 1962-01-22 CH CH124463A patent/CH442315A/en unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1288787B (en) * | 1966-09-08 | 1969-02-06 | Bayer Ag | Polyamide molding compounds with compounds containing imide groups as mold release agents |
| US7875720B2 (en) * | 2000-04-27 | 2011-01-25 | Nalco Company | Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems |
| US7714044B2 (en) | 2003-11-14 | 2010-05-11 | Basf Akitengesellschaft | Use of 4-cyano-naphthalene-1, 8-dicarboximide derivatives and related compounds to protect organic material from the damaging effects of light |
| CN1902180B (en) * | 2003-11-14 | 2010-08-25 | 巴斯福股份公司 | Use of 4-cyano-naphthalene-1, 8-dicarboximide derivatives and related compounds for protecting organic materials from the damaging effects of light |
| US8894881B2 (en) | 2008-01-31 | 2014-11-25 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | 1,8-naphthalimide derivatives as scintillation agents, in particular for discriminating between fast neutrons and gamma rays |
| US8383656B2 (en) | 2009-10-09 | 2013-02-26 | The Ohio State University Research Foundation | Thiazolidinedione energy restriction-mimetic agents |
Also Published As
| Publication number | Publication date |
|---|---|
| CH409850A (en) | 1965-12-15 |
| CH446713A (en) | 1967-11-15 |
| BE612955A (en) | 1962-05-16 |
| DE1445961B2 (en) | 1978-09-28 |
| CH442315A (en) | 1967-08-31 |
| CH427811A (en) | 1967-01-15 |
| DE1445961A1 (en) | 1969-12-11 |
| DE1445961C3 (en) | 1979-05-17 |
| CH461495A (en) | 1968-08-31 |
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