GB1353051A - Amides and hydrazides - Google Patents
Amides and hydrazidesInfo
- Publication number
- GB1353051A GB1353051A GB2045071A GB2045071A GB1353051A GB 1353051 A GB1353051 A GB 1353051A GB 2045071 A GB2045071 A GB 2045071A GB 2045071 A GB2045071 A GB 2045071A GB 1353051 A GB1353051 A GB 1353051A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- amino
- group
- substituted
- hydrazine
- 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
- 150000001408 amides Chemical class 0.000 title abstract 4
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 title abstract 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 10
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 abstract 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 4
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 229960004909 aminosalicylic acid Drugs 0.000 abstract 3
- 238000005282 brightening Methods 0.000 abstract 3
- 230000003287 optical effect Effects 0.000 abstract 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 2
- AKEUNCKRJATALU-UHFFFAOYSA-N 2,6-dihydroxybenzoic acid Chemical compound OC(=O)C1=C(O)C=CC=C1O AKEUNCKRJATALU-UHFFFAOYSA-N 0.000 abstract 2
- IOMZCWUHFGMSEJ-UHFFFAOYSA-N 4-(azaniumylamino)benzenesulfonate Chemical compound NNC1=CC=C(S(O)(=O)=O)C=C1 IOMZCWUHFGMSEJ-UHFFFAOYSA-N 0.000 abstract 2
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical class OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- -1 amino, substituted amino, phenyl Chemical group 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 2
- 150000001555 benzenes Chemical class 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 229960004889 salicylic acid Drugs 0.000 abstract 2
- 229920002994 synthetic fiber Polymers 0.000 abstract 2
- RHLPAVIBWYPLRV-UHFFFAOYSA-N 2-hydroxy-4-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1O RHLPAVIBWYPLRV-UHFFFAOYSA-N 0.000 abstract 1
- 229920001131 Pulp (paper) Polymers 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical class 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical class 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003599 detergent Substances 0.000 abstract 1
- 239000004744 fabric Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002429 hydrazines Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- HRRDCWDFRIJIQZ-UHFFFAOYSA-N naphthalene-1,8-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=CC2=C1 HRRDCWDFRIJIQZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003870 salicylic acids Chemical class 0.000 abstract 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 125000004306 triazinyl group Chemical group 0.000 abstract 1
Classifications
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
- C07C309/60—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
Abstract
1353051 Amides and hydrazides ALBRIGHT & WILSON (AUSTRALIA) Ltd 19 April 1971 [2 Feb 1970] 20450/71 Heading C2C Amides and hydrazides suitable for use as optical brightening agents for paper, natural or synthetic fibres and fabrics and detergent compositions, are prepared by reacting an amine or hydrazine with an aromatic carboxylic acid which has a hydroxyl, amino or carboxyl group in a position ortho to the carboxylic acid group and which may also contain a sulphonate group, an optionally substituted triazinylamino group or an optionally substituted triazinyloxy group. The invention also comprises per se the compound 4,4<SP>1</SP>-bis-(sulphosalicyl) hydrazide. The amines or hydrazines have the formula R<SP>11</SP>-NH-R<SP>1</SP> with R<SP>1</SP> and R<SP>11</SP> preferably being hydrogen, amino, substituted amino, phenyl, substituted phenyl, triazinyl, naphthyl or substituted naphthyl. Suitable carboxylic acids are salicylic acid, substituted salicylic acids, e.g. sulphosalicylic acids, substituted o-phthalic acid (or anhydride), naphthalic acid (or anhydride), o-amino benzoic acid and 1,2-amino naphthoic acid. Further substituents, other than those referred to above, on the benzene nucleus are, for example, hydroxyl, nitrile, phenyl carboxylate, carbonyl, -SO 3 M (M is H or an alkali or alkaline earth metal), SO 3 W (W is a substituted amide, alkyl or aryloxy group), a primary or secondary amino group, an amido group or a substituted oxy or heterocyclic group. Although these groups are normally present in the benzene nucleus of the carboxylic acid before the reaction with the amine or hydrazine it is also possible to introduce the groups after the reaction. Examples describe the preparation of optical brightening agents from (1) 2-hydroxy-4- sulphobenzoic acid and (a) hydrazine, (b) psulphophenyl hydrazine, (c) p-phenylene diamine with further reaction of the product with cyanuric chlorides, and (d) 1-naphthylamine; (2) the sodium salt of 1-amino-2-naphthol-4- sulphonic acid and p-aminosalicylic acid; (3) 2,6-dihydroxybenzoic acid and (a) p-sulphophenyl hydrazine, with further reaction of the product with cyanuric chloride, (b) 1-naphthylamine and (c) 1-amino-2-naphthol-4-sulphonic acid; (4) p-sulphobenzoguanamine and salicylic acid; (5) p-aminosalicylic acid and (a) 1- naphthylamine, (b) p-phenylene diamine, (c) p-sulphophenyl hydrazine; (6) 2-hydroxy-5- sulphobenzoic acid and 1-amino-2-naphthol-4- sulphonic acid; and (7) 4-amino-salicylic acid and hydrazine; and also their use in the optical brightening of textiles and paper pulp.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU20970 | 1970-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1353051A true GB1353051A (en) | 1974-05-15 |
Family
ID=3691035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2045071A Expired GB1353051A (en) | 1970-02-02 | 1971-04-19 | Amides and hydrazides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1353051A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007128744A3 (en) * | 2006-05-08 | 2008-01-03 | Ciba Sc Holding Ag | Triazine derivatives |
-
1971
- 1971-04-19 GB GB2045071A patent/GB1353051A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007128744A3 (en) * | 2006-05-08 | 2008-01-03 | Ciba Sc Holding Ag | Triazine derivatives |
| JP2009536174A (en) * | 2006-05-08 | 2009-10-08 | チバ ホールディング インコーポレーテッド | Triazine derivative |
| US8444879B2 (en) | 2006-05-08 | 2013-05-21 | Basf Se | Triazine derivatives |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |