GB838994A - New anthradipyridazones and their use in polymeric materials - Google Patents

New anthradipyridazones and their use in polymeric materials

Info

Publication number
GB838994A
GB838994A GB3714256A GB3714256A GB838994A GB 838994 A GB838994 A GB 838994A GB 3714256 A GB3714256 A GB 3714256A GB 3714256 A GB3714256 A GB 3714256A GB 838994 A GB838994 A GB 838994A
Authority
GB
United Kingdom
Prior art keywords
dipyridazone
anthra
alkyl
hydrazine
appropriate
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
Application number
GB3714256A
Inventor
Francis Irving
Charles Hugh Reece
Neil Munro
Robert Hugh Wilson
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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.)
Filing date
Publication date
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB3714256A priority Critical patent/GB838994A/en
Priority to CH5338257A priority patent/CH367179A/en
Priority to BE562948A priority patent/BE562948A/xx
Priority to NL222995A priority patent/NL103584C/xx
Priority to FR1199252D priority patent/FR1199252A/en
Publication of GB838994A publication Critical patent/GB838994A/en
Priority to GB2041764A priority patent/GB1047213A/en
Priority to BE663424A priority patent/BE663424A/xx
Priority to FR17168A priority patent/FR87884E/en
Priority to NL6506215A priority patent/NL6506215A/xx
Expired legal-status Critical Current

Links

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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C09B5/16—Benz-diazabenzanthrones, e.g. anthrapyrimidones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
    • C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6856—Dicarboxylic acids and dihydroxy compounds
    • 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
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3462—Six-membered rings
    • C08K5/3465—Six-membered rings condensed with carbocyclic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The invention comprises anthra - dipyridazones having the general formula <FORM:0838994/IV (b)/1> wherein X and Y are the same or different and represent hydrogen or a monovalent organic radical such as a -CH2COOH group or an alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, alkyl-cycloalkyl, alkenyl, aralkyl which may be substituted by alkyl or halogen, e.g. chlorine, aryl which may be substituted by alkyl, alkoxy or halogen, e.g. chlorine, or a heterocyclic or alkyl-heterocyclic radical. The compounds give strongly blue fluorescent solutions and are useful in modifying the colour of textiles and polymeric materials (see Groups IV (a) and IV (c)) and of paints, lacquers and varnish, some being colouring agents and others whitening agents. They may be prepared by interacting a hydrazine of the formula NH2.NHY with an anthramono-pyridazone of the formula <FORM:0838994/IV (b)/2> wherein X and Y are as defined above and one Z represents hydrogen and the other Z represents a carboxyl group or functional derivative thereof, e.g. an ester, acid chloride, amide or nitrile group, the presence of water being necessary if the second Z represents a nitrile or amido group. Suitable hydrazines are hydrazine, methyl-, ethyl-, n-butyl-, hydroxy-ethyl- and allyl-hydrazines, hydrazino-acetic acid, phenyl-, a -naphthyl-, p-tolyl-, o-chlorphenyl-, 2 : 5-dichlorophenyl- and 2 : 6-dimethyl phenyl-hydrazines and 3-hydrazino pyridine. The reaction may be effected by heating, if desired in the presence of a liquid medium such as water, sulphuric acid, oleum, acetic acid or xylene. The anthra-di-pyridazones, wherein X and Y are identical are preferably formed directly from the appropriate anthraquinone dicarboxylic acid or its functional derivative by interaction with more than one equivalent of the appropriate hydrazine compound without isolation of the monopyridazone intermediate and in the presence of water if the functional p derivative is a nitrile or amide. The anthra monopyridazones used in the first method as starting materials may be prepared by reacting anthraquinone- 1 : 5- or -1 : 4-dicarboxylic acid or a functional derivative thereof with a hydrazine NH2.NHX in the presence of one molar proportion of an alkali or an amount of the hydrazine compound insufficient to cause formation of the dipyridazone. Examples describe the preparations of (1) and (2) 2-(211 : 611-dimethyl phenyl)-8 - n - butylanthra - 11 : 91 (N) : 101 (N) : 51 - dipyridazone; (3) 2 : 8-diphenylanthra-11 : 91 (N): 101 (N) : 51 - dipyridazone; (4) 2 : 8 - di - p - toly anthra - 1 : 91 (N) : 101 (N) - 51 - dipyridazone; (5) 2 : 8 - di - (211 - chlorophenyl) anthra - 11 : 91 (N) : 101 (N) - 51 - dipyridazone; (6) 2 : 8 - di - (211 : 511 - dichlorophenyl) anthra - 11 : 91 (N) : 101 (N) : 51 - dipyridazone; (7) 2 : 8 - dibutyl anthra - 11 : 91 (N) : 101 (N1) : 51 - dipyridazone; (8) 2 : 7 - diphenyl anthra - 11 : 91 (N) : 101 (N) : 41 - dipyridazone; (9) and (24) anthra-11 : 91 (N) : 101 : (N) : 51 - dipyridazone; (10) and (11) 2 : 8-di - (211 : 611 - dimethyl phenyl) anthra - 11 : 91 (N) : 101 (N) - 51 - dipyrisazone; (12) 2 : 8 : di(211 - hydroxyethyl) anthra - 11 : 91 (N) : 101 (N) : 51 - pyridazone; (13) 2-(211 : 611-dimethyl phenyl) - anthra - 11 : 91 (N) : 101 (N) - 5 - dipyridazone; (14) 2 : 8-di-(211 : 611-diethyl phenyl) anthra - 11 : 91 (N) : 101 (N) : 51 - dipyridazone; (15) 2 - (211 : 611 - diethyl phenyl) anthra - 11 : 91 (N) : 101 (N) : 51 - dipyridazone; (16) 2 : 8 - di - (o - bromo phenyl) anthra - 11 : 91 (N) : 101 (N) : 51 - dipyridazone; (17) 2 - (611 - chloro - 211 - methyl phenyl) anthra - 11 : 91 (N) : 101 (N) : 51dipyridazone; (18) and (19) 2-(211 : 611-dichlorophenyl) anthra - 11 : 91 (n) : 101 (N) : 51 - dipyridazone; (2) 2-(211 : 611-dimethyl phenyl)-7-n - butyl anthra - 11 : 91 (N) : 101 (N) : 41 - dipyridazone; (21) 2 : 7-di-n-butyl anthra-11 : 91 (N) : 101 (N) : 4 - dipyridazone; (22) 2 : 7 - di - o - chlorophenyl anthra - 11 : 91 (N) : 101 (N) : 41-dipyrazone; and (23) 2 : 7-di-(211 : 611-dimethyl phenyl) anthra - 11 : 91 (N) : 101 (N) : 4 - dipyridazone, by reaction of an appropriate hydrazine or hydrochloride or hydrate thereof with an appropriate anthra-mono-pyridazone carboxylic acid or in certain cases, where X and Y are the same, by reaction of excess of the appropriate hydrazine or hydrochloride, hydrate or sulphate thereof, with the appropriate anthraquinone carboxylic acid or dinitrile thereof. The preparation of most of the anthra-monopyridazone carboxylic acid starting materials by the above-described method are given in the corresponding examples. Specification 813,093 is referred to.ALSO:The invention comprises anthradipyridazones having the general formula <FORM:0838994/IV(c)/1> wherein X and Y may be the same or different and represent hydrogen or a monovalent organic radical such as a -CH2COOH group or an alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, alkylcycloalkyl, alkenyl, aralkyl which may be substituted by alkyl or halogen, e.g. chlorine, aryl which may be substituted by alkyl, alkoxy or halogen, e.g. chlorine, or a heterocyclic or alkyl-heterocyclic radical. The compounds give strongly blue fluorescent solutions and are useful in treating textile materials and in modifying the colour of polymeric materials (see Group IV (a)), some being colouring agents and others whitening agents. They may be prepared by interacting a hydrazine of the formula NH2.NHY with an anthramonopyridazone of the formula <FORM:0838994/IV(c)/2> wherein X and Y are as defined above and one Z represents hydrogen and the other Z represents a carboxyl group or functional derivative thereof, e.g. an ester, acid chloride, amide or nitrile group, the presence of water being necessary if the second Z represents a nitrile or amide group. Suitable hydrazines are hydrazine, methyl-, ethyl-, n-butyl-, hydroxyethyl- and allyl-hydrazines, hydrazinoacetic acid, phenyl-, a -naphthyl-, p-tolyl-, o-chlorphenyl-, 2 : 5-dichlorophenyl- and 2 : 6-dimethylphenyl-hydrazines and 3-hydrazinopyridine. The reaction medium may be water, sulphuric acid, oleum, acetic acid or xylene. Those anthradipyridazones of the above general formul wherein X and Y are identical are preferably formed directly from the appropriate anthraquinone dicarboxylic acid or functional derivative thereof by interaction with more than one equivalent of the appropriate hydrazine compounds without isolation of the monopyridazone intermediate and in the presence of water if the functional derivative used is a nitrile or an amide. Examples describe the preparations of: (1) and (2) 2-(211:611-dimethylphenyl) - 8 - n - butylanthra - 11 : 91-(N) : 101 - (N) : 51 - dipyridazone, (3) 2 : 8-diphenylanthra-11 : 91-(N) : 101-(N) 51-dipyridazone, (4) 2 : 8-di-p-tolylanthra-1 : 91-(N) : 101-(N) - 51 - dipyridazone, (5) 2 : 8 - di - (211-chlorophenyl)anthra - 11:91 - (N) : 101-(N) - 51-dipyridazone, (6) 2 : 8 - di - (211:511 - dichlorophenyl)anthra - 11:91 - (N) : 101 - (N) : 51 - dipyridazone, (7) 2 : 8 - dibutylanthra - 11:91-(N) : 101 - (N1) : 51 - dipyridazone, (8) 2 : 7-diphenylanthra - 11:91 - (N) : 101 - (N) : 41 - dipyridazone, (9) and (24) anthra-11:91-(N):101-(N) : 51-dipyridazone, (10) and (11) 2 : 8-di-(211:611 - dimethylphenyl)anthra - 11:91 - (N) : 101 - (N) - 51 - dipyridazone, (12) 2 : 8 - di - (211-hydroxyethyl)anthra - 11:91 - (N) : 101 - (N) : 51 - dipyridazone, (13) 2 - (211:611 - dimethylphenyl)anthra - 11:91 - (N) : 101 - (N) - 5 - di pyridazone, (14) 2 : 8 - di - (211:611 - diethylphenyl)anthra - 11:91 - (N) : 101 - (N) : 51-dipyridazone, (15) 2 - (211:611 - diethylphenyl)-anthra - 11:91 - (N) : 101 - (N) : 51 - dipyridazone, (16) 2 : 8 - di - (o - bromophenyl)anthra-11:91 - (N) : 101 - (N) : 51 - dipyridazone, (17) 2 - (611 - chloro - 211 - methylphenyl)anthra-11:91 - (N) : 101 - (N) : 51 - dipyridazone, (18) and (19) 2 - (211:611 - dichlorophenyl)anthra-11:91 - (N) : 101 - (N) : 51 - dipyridazone, (20) 2 - (211:611 - dimethylphenyl) - 7 - n - butylanthra - 11:91 - (N) : 101 - (N) : 41 - dipyridazone, (21) 2 : 7 - di - n - butylanthra - 11:91-(N) : 101 - (N) : 4 - dipyridazone, (22) 2 : 7-di - o - chlorophenylanthra - 11:91 - (N) : 101-(N) : 41 - dipyrazone, and (23) 2 : 7 - di - (211:611 - dimethylphenyl)anthra - 11:91 - (N) : 101-(N) : 4-dipyridazone, by reaction of an appropriate hydrazine or hydrochloride or hydrate thereof with an appropriate anthra-monopyridazone carboxylic acid or in certain cases, where X and Y are the same, by reaction of an excess of the appropriate hydrazine, or hydrochloride, hydrate or sulphate thereof, with the appropriate anthraquinone carboxylic acid or dinitrile thereof. Examples 25, 26, 27 and 35 describe the treatment of polyethylene terephthalate fabric with an aqueous dispersion containing a dipyridazone of the above kind and a wetting agent, whereby a whitening effect is obtained. Specification 813,093 is referred to.ALSO:Artificial resins, including polyamides, polyesters, polystyrene and cellulose acetate, are treated to modify their colour with anthradipyridazones having the general formula <FORM:0838994/IV (a)/1> in which X and Y may be the same or different and represent hydrogen or a monovalent organic radical such as a -CH2COOH group or an alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, alkylcycloalkyl, alkenyl, aralkyl which may be substituted by halogen, e.g. chlorine, or an alkyl group, aryl which may be substituted by alkyl, alkoxy or halogen, or a heterocyclic or alkylsubstituted heterocyclic radical. The pyridazones give blue fluorescent solutions and some serve as colouring matters and others as whitening agents. They may be added during the manufacture of the polymeric material or may be added to the polymeric material before it is spun, extruded or otherwise shaped. Alternatively, films and textile materials may be treated with a solution or suspe
GB3714256A 1956-12-05 1956-12-05 New anthradipyridazones and their use in polymeric materials Expired GB838994A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB3714256A GB838994A (en) 1956-12-05 1956-12-05 New anthradipyridazones and their use in polymeric materials
CH5338257A CH367179A (en) 1956-12-05 1957-12-04 Process for the production of polycyclic organic compounds
BE562948A BE562948A (en) 1956-12-05 1957-12-04
NL222995A NL103584C (en) 1956-12-05 1957-12-05
FR1199252D FR1199252A (en) 1956-12-05 1957-12-05 Polycyclic organic compounds, in particular of the anthradipyridazone series
GB2041764A GB1047213A (en) 1956-12-05 1964-05-15
BE663424A BE663424A (en) 1956-12-05 1965-05-04
FR17168A FR87884E (en) 1956-12-05 1965-05-14 Polycyclic organic compounds, in particular of the anthradipyridazone series
NL6506215A NL6506215A (en) 1956-12-05 1965-05-14

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB3714256A GB838994A (en) 1956-12-05 1956-12-05 New anthradipyridazones and their use in polymeric materials
GB3714356 1956-12-05

Publications (1)

Publication Number Publication Date
GB838994A true GB838994A (en) 1960-06-22

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ID=26263351

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Application Number Title Priority Date Filing Date
GB3714256A Expired GB838994A (en) 1956-12-05 1956-12-05 New anthradipyridazones and their use in polymeric materials

Country Status (4)

Country Link
BE (1) BE562948A (en)
FR (1) FR1199252A (en)
GB (1) GB838994A (en)
NL (1) NL103584C (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6291425B1 (en) 1999-09-01 2001-09-18 Guilford Pharmaceuticals Inc. Compounds, methods and pharmaceutical compositions for treating cellular damage, such as neural or cardiovascular tissue damage
US6306889B1 (en) 1997-09-03 2001-10-23 Guilford Pharmaceuticals Inc. Compounds, methods and pharmaceutical compositions for treating neural or cardiovascular tissue damage
US6348475B1 (en) 2000-06-01 2002-02-19 Guilford Pharmaceuticals Inc. Methods, compounds and compositions for treating gout
US6380211B1 (en) 1997-09-03 2002-04-30 Guilford Pharmaceutical Inc. Alkoxy-substituted compounds, methods, and compositions for inhibiting PARP activity
US6387902B1 (en) 1998-12-31 2002-05-14 Guilford Pharmaceuticals, Inc. Phenazine compounds, methods and pharmaceutical compositions for inhibiting PARP
US6395749B1 (en) 1998-05-15 2002-05-28 Guilford Pharmaceuticals Inc. Carboxamide compounds, methods, and compositions for inhibiting PARP activity
US6426415B1 (en) 1997-09-03 2002-07-30 Guilford Pharmaceuticals Inc. Alkoxy-substituted compounds, methods and compositions for inhibiting parp activity
US6514983B1 (en) 1997-09-03 2003-02-04 Guilford Pharmaceuticals Inc. Compounds, methods and pharmaceutical compositions for treating neural or cardiovascular tissue damage
US6635642B1 (en) 1997-09-03 2003-10-21 Guilford Pharmaceuticals Inc. PARP inhibitors, pharmaceutical compositions comprising same, and methods of using same
US6723733B2 (en) 2000-05-19 2004-04-20 Guilford Pharmaceuticals, Inc. Sulfonamide and carbamide derivatives of 6(5H)phenanthridinones and their uses

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6306889B1 (en) 1997-09-03 2001-10-23 Guilford Pharmaceuticals Inc. Compounds, methods and pharmaceutical compositions for treating neural or cardiovascular tissue damage
US6346536B1 (en) 1997-09-03 2002-02-12 Guilford Pharmaceuticals Inc. Poly(ADP-ribose) polymerase inhibitors and method for treating neural or cardiovascular tissue damage using the same
US6380211B1 (en) 1997-09-03 2002-04-30 Guilford Pharmaceutical Inc. Alkoxy-substituted compounds, methods, and compositions for inhibiting PARP activity
US6426415B1 (en) 1997-09-03 2002-07-30 Guilford Pharmaceuticals Inc. Alkoxy-substituted compounds, methods and compositions for inhibiting parp activity
US6514983B1 (en) 1997-09-03 2003-02-04 Guilford Pharmaceuticals Inc. Compounds, methods and pharmaceutical compositions for treating neural or cardiovascular tissue damage
US6635642B1 (en) 1997-09-03 2003-10-21 Guilford Pharmaceuticals Inc. PARP inhibitors, pharmaceutical compositions comprising same, and methods of using same
US6395749B1 (en) 1998-05-15 2002-05-28 Guilford Pharmaceuticals Inc. Carboxamide compounds, methods, and compositions for inhibiting PARP activity
US6387902B1 (en) 1998-12-31 2002-05-14 Guilford Pharmaceuticals, Inc. Phenazine compounds, methods and pharmaceutical compositions for inhibiting PARP
US6291425B1 (en) 1999-09-01 2001-09-18 Guilford Pharmaceuticals Inc. Compounds, methods and pharmaceutical compositions for treating cellular damage, such as neural or cardiovascular tissue damage
US6716828B1 (en) 1999-09-01 2004-04-06 Guilford Pharmaceuticals, Inc. Compounds, methods and pharmaceutical compositions for treating cellular damage, such as neural or cardiovascular tissue damage
US6723733B2 (en) 2000-05-19 2004-04-20 Guilford Pharmaceuticals, Inc. Sulfonamide and carbamide derivatives of 6(5H)phenanthridinones and their uses
US6348475B1 (en) 2000-06-01 2002-02-19 Guilford Pharmaceuticals Inc. Methods, compounds and compositions for treating gout

Also Published As

Publication number Publication date
NL103584C (en) 1963-01-15
FR1199252A (en) 1959-12-11
BE562948A (en) 1958-06-04

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