GB962019A - Naphthalimide optical whitening agents - Google Patents
Naphthalimide optical whitening agentsInfo
- Publication number
- GB962019A GB962019A GB12963/62A GB1296362A GB962019A GB 962019 A GB962019 A GB 962019A GB 12963/62 A GB12963/62 A GB 12963/62A GB 1296362 A GB1296362 A GB 1296362A GB 962019 A GB962019 A GB 962019A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- aryl
- formula
- substituted
- treated
- 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
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
- D06L4/614—Optical bleaching or brightening in aqueous solvents
- D06L4/636—Optical bleaching or brightening in aqueous solvents with disperse brighteners
Abstract
The invention comprises optical whitening agents of formula: <FORM:0962019/C1/1> where R1 is an alkyl, aryl or cycloalkyl group, which may be substituted, and R2 is H or an alkyl, aryl, aralkyl or cycloalkyl group, which may be substituted, R1 being the same as, or different from, R2. The compounds may be made by treating a compound of the above formula, where X replaces R1O, X being a sulpho group, or a salt thereof, a nitro group or a halogen atom, in the presence of a condensing agent, with a compound of formula R, OH, or a salt thereof; or by etherifying a compound where X is OH, or a salt thereof; or by condensing an appropriate dicarboxylic acid, or anhydride thereof, with an amine of formula R2NH2. Representative of specified values for R1 are methyl, iso-pentyl, n-tridecyl, hydroxyethyl, propoxypropyl, aminopropyl, N,N-dimethylaminoethyl, N-trimethyl ammonium propyl, naphthyl, benzyl and cyclohexyl. Indicated substituents for R1 when aryl are alkyl, alkoxy, hydroxy, alkoxyalkyl, hydroxy-alkyl, amino, sec. and tert.-aminoalkyl, great-ammonium alkyl, nitro and halogen. Representative of indicated amines of formula R2NH2 are ethyl, iso-decyl and propanolamines, ethylene diamine, N,N-dimethylpropylene diamine, ethoxyethylamine, naphthylamine, benzylamine and cyclohexylamine. R2, when aryl may contain such groups as alkyl, alkoxy, hydroxy, alkoxyalkyl, hydroxy-alkyl, nitro, amino and halogen. R2 may also be <FORM:0962019/C1/2> The first method is preferably effected with caustic soda, or potash, as condensation agent and the second with conventional etherifying agents in the presence of alkaline substances. In all methods solvents or diluents may be present and temperatures of up to 200 DEG C. used. Numerous examples are provided of the preparation of the compounds and their uses for whitening textiles (see Division D1) and synthetic resins (see Division C3).ALSO:Moulded materials from synthetic resins e.g. polyvinyl chloride, polyacrylate, polyester, polycarbonate, polyurethane, polyamide, polyolefine and polystyrene resins, are white-enhanced by the addition, during, or after their manufacture, of an optional whitening agent of formula: <FORM:0962019/C3/1> where R1 is an alkyl, aryl or cycloalkyl group, which may be substituted, and R2 is H or an alkyl, aryl, aralkyl or cycloalkyl group, which may be substituted, R1 being the same as, or different from, R2. In Example 68 0.2%, by weight, of one of the agents, e.g. N-phenyl-4-methoxy-naphthalimid and, optionally, 2 to 5% by weight of titanium dioxide, is incorporated in a polystyrene, polyvinylchloride, polyacrylate, polyamide, polyester or polycarbonate resin which, after kneading, is formed into plates.ALSO:Textile materials are treated with an optical whitening agent of formula <FORM:0962019/D1-D2/1> where R1 is an alkyl, aryl or cycloalkyl group, which may be substituted, and R2 is H or an alkyl, aryl, aralkyl or cycloalkyl group, which may be substituted, R1 being the same as, or different from, R2. Materials treated are especially synthetic organic high molecular weight substances such as polyesters e.g. polyethylene terephthalate, polyvinyls e.g. polyacrylonitrile and polyvinylchloride, polyamides, polyolefines e.g. polypropylene and cellulose esters e.g. cellulose acetate. In examples (63) polyester material is treated with an aqueous dispersion of N-methyl-4-methoxy-naphthalimide in the presence of chlorobenzenes and a condensate of naphthalene-2-sulphonic acid and formaldehyde (65) and (66) the same naphthalimide, dispersed in water with a condensate of 2-mephthol-6-sulphonic acid, creol and formaldehyde, is used to treat cellulose acetate and polypropylene materials respectively, (64) polyester material is treated with N-butyl-4-methoxy-naphthalimide under the conditions of (65) and in (67) polyacrylonitrile material is treated with an acetic acid, sodium acetate aqueous solution of compounds where either R1 is Me and R2 is (CH2)3-N+(CH3)3 or R1 is (CH3)3N+-(CH2)2 and R2 is Me, all the treated textiles being soaped, rinsed and dried.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1258061 | 1961-04-12 | ||
JP2565261 | 1961-07-20 | ||
JP2565161 | 1961-07-20 | ||
JP2565061 | 1961-07-20 | ||
JP2836961 | 1961-08-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB962019A true GB962019A (en) | 1964-06-24 |
Family
ID=27519413
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB12963/62A Expired GB962019A (en) | 1961-04-12 | 1962-04-04 | Naphthalimide optical whitening agents |
Country Status (4)
Country | Link |
---|---|
CH (5) | CH442732A (en) |
DE (1) | DE1419350A1 (en) |
FR (1) | FR1344883A (en) |
GB (1) | GB962019A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4814453A (en) * | 1986-06-02 | 1989-03-21 | Hoechst Aktiengesellschaft | Naphthalimides containing sulfuric acid ester groups, a process for their preparation and their use |
US4845223A (en) * | 1985-12-19 | 1989-07-04 | Basf Aktiengesellschaft | Fluorescent aryloxy-substituted perylene-3,4,9,10-tetracarboxylic acid diimides |
WO2005075574A1 (en) * | 2004-02-07 | 2005-08-18 | Wella Aktiengesellschaft | Neutral and cationic naphthalene derivatives and dyes containing said compounds for dyeing keratin fibers |
Families Citing this family (5)
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 |
DE2944867A1 (en) * | 1979-11-07 | 1981-05-27 | Hoechst Ag, 6000 Frankfurt | CATIONIC COMPOUNDS OF THE NAPHTHALIMIDE SERIES, METHOD FOR THE PRODUCTION AND USE THEREOF |
US4782064A (en) * | 1986-07-21 | 1988-11-01 | American Cyanamid Co. | 2-heteroaryl-alkyl-1H-benz[de]-isoquinoline-1,3(2H)-diones |
DE10353328A1 (en) * | 2003-11-14 | 2005-06-16 | Basf Ag | New naphthalene-1,8-dicarboxylic monoimides for use as sole light stabilizer to protect organic material, e.g. plastics, polymer dispersions, paints and photographic emulsions, from damaging effects of light |
JP5847085B2 (en) | 2009-10-09 | 2016-01-20 | ザ オハイオ ステート ユニバーシティー リサーチ ファウンデーション | Thiazolidinedione energy limiting mimetics |
-
1962
- 1962-04-04 GB GB12963/62A patent/GB962019A/en not_active Expired
- 1962-04-10 CH CH1457762A patent/CH442732A/en unknown
- 1962-04-10 CH CH432462A patent/CH447096A/en unknown
- 1962-04-10 DE DE19621419350 patent/DE1419350A1/en active Pending
- 1962-04-12 FR FR894239A patent/FR1344883A/en not_active Expired
- 1962-07-18 CH CH863862A patent/CH416640A/en unknown
- 1962-07-18 CH CH863962A patent/CH416641A/en unknown
- 1962-07-18 CH CH863762A patent/CH416639A/en unknown
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4845223A (en) * | 1985-12-19 | 1989-07-04 | Basf Aktiengesellschaft | Fluorescent aryloxy-substituted perylene-3,4,9,10-tetracarboxylic acid diimides |
US4814453A (en) * | 1986-06-02 | 1989-03-21 | Hoechst Aktiengesellschaft | Naphthalimides containing sulfuric acid ester groups, a process for their preparation and their use |
WO2005075574A1 (en) * | 2004-02-07 | 2005-08-18 | Wella Aktiengesellschaft | Neutral and cationic naphthalene derivatives and dyes containing said compounds for dyeing keratin fibers |
US7544215B2 (en) | 2004-02-07 | 2009-06-09 | Wella Ag | Neutral and cationic naphthalene and colorants for keratin fibers containing these compounds |
Also Published As
Publication number | Publication date |
---|---|
CH447096A (en) | 1968-03-15 |
CH416639A (en) | 1966-07-15 |
CH432462A4 (en) | 1967-08-15 |
CH442732A (en) | 1967-08-31 |
CH416641A (en) | 1966-07-15 |
FR1344883A (en) | 1963-12-06 |
CH416640A (en) | 1966-07-15 |
DE1419350A1 (en) | 1969-04-30 |
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