GB536047A - Process for the production of colourless halogen substituted urea sulphonic acids, and the resulting products - Google Patents
Process for the production of colourless halogen substituted urea sulphonic acids, and the resulting productsInfo
- Publication number
- GB536047A GB536047A GB50/41A GB5041A GB536047A GB 536047 A GB536047 A GB 536047A GB 50/41 A GB50/41 A GB 50/41A GB 5041 A GB5041 A GB 5041A GB 536047 A GB536047 A GB 536047A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- sulphonic acid
- chloride
- condensed
- sulphonic
- 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
- 239000002253 acid Substances 0.000 title abstract 5
- 150000007513 acids Chemical class 0.000 title abstract 5
- 150000003672 ureas Chemical class 0.000 title abstract 3
- 239000004202 carbamide Substances 0.000 title abstract 2
- 125000005843 halogen group Chemical group 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 229910052736 halogen Inorganic materials 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- 239000012948 isocyanate Substances 0.000 abstract 5
- 150000002513 isocyanates Chemical class 0.000 abstract 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 4
- 150000001555 benzenes Chemical class 0.000 abstract 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract 3
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 abstract 2
- -1 carbonic acid halide Chemical class 0.000 abstract 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 abstract 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- AWOGJPUHYGTHMO-UHFFFAOYSA-N 1-phenyltridecan-1-amine Chemical compound CCCCCCCCCCCCC(N)C1=CC=CC=C1 AWOGJPUHYGTHMO-UHFFFAOYSA-N 0.000 abstract 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 abstract 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 abstract 1
- KLPPPIIIEMUEGP-UHFFFAOYSA-N 4-dodecylaniline Chemical compound CCCCCCCCCCCCC1=CC=C(N)C=C1 KLPPPIIIEMUEGP-UHFFFAOYSA-N 0.000 abstract 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 abstract 1
- KXEKUVPQDXOCBG-UHFFFAOYSA-N 5-chloro-2-methoxy-4-methylaniline Chemical compound COC1=CC(C)=C(Cl)C=C1N KXEKUVPQDXOCBG-UHFFFAOYSA-N 0.000 abstract 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 abstract 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- 239000003899 bactericide agent Substances 0.000 abstract 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000645 desinfectant Substances 0.000 abstract 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 abstract 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 abstract 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical class C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 abstract 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 abstract 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- XNBKKRFABABBPM-UHFFFAOYSA-N n,n-diphenylcarbamoyl chloride Chemical compound C=1C=CC=CC=1N(C(=O)Cl)C1=CC=CC=C1 XNBKKRFABABBPM-UHFFFAOYSA-N 0.000 abstract 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 abstract 1
- LQKYCMRSWKQVBQ-UHFFFAOYSA-N n-dodecylaniline Chemical compound CCCCCCCCCCCCNC1=CC=CC=C1 LQKYCMRSWKQVBQ-UHFFFAOYSA-N 0.000 abstract 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C07D327/08—[b,e]-condensed with two six-membered carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- 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
- D06M13/402—Amides imides, sulfamic acids
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
-
- 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
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
-
- 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
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
- D06M16/006—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic with wool-protecting agents; with anti-moth agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
536,047. Halogenated urea sulphonic acids. GEIGY AKT.-GES., J. R. June, 15, 1939, Nos. 50/41 and 51/41. Convention dates, June 16, 1938 and Dec. 31, 1938. Divided out of 536,011. Samples furnished. [Class 2 (iii)] [Also in Group VIII] Colourless halogen-substituted urea sulphonic acids of the benzene series are made by treating with a carbonic acid halide or an isocyanate a colourless monoamine or monoamino sulphonic acid of the benzene series, which in the case of polynuclear compounds contains directly linked benzene nuclei, or benzene nuclei linked by O, S, SO, SO 2 NH. CH 2 , CONH or NH-CO-NH, the components being so selected that the products contain at least one halogen atom and one sulphonic group ; alternatively these may be introduced by subsequent halogenation or sulphonation. Heterocyclic compounds of the general formula where X is a direct linkage or O, and Y is O or S, may also be used as parent materials. The carbamic acid chlorides and isocyanates employed may be made by known processes from primary or secondary aliphatic, araliphatic or aromatic amines, e.g. aniline, p-toluidine, chloranilines, 3-chlor-4-methyl-6-methoxy-aniline, 4-nitraniline, ethylaniline, 4-laurylaniline, laurylphenylamine, diphenylamine, 4:4'-dichlor- 2 - aminodiphenylether, 4<SP>1</SP> - chlor - 4 - aminodiphenylsulphone, laurylamine, α-dodecylbenzylamine &c. A large number of amines and aminosulphonic acids of the benzene series is specified, including diphenyls, diphenylethers, diphenylmethane, diphenylsulphides, diphenylsulphones, diphenylamines, benzanilides, diphenylureas, and simple benzene compounds such as aniline, anisidine or nitraniline. The products are useful for moth-proofing wool and other substances, and as disinfectants, bactericides &c. In examples, (1) 4-amino-4<SP>1</SP>-chlor- 1:1<SP>1</SP>-diphenylether is condensed with 3:4- dichlorphenylisocyanate ; (2) 2-amino-4:4<SP>1</SP>- dichlor -1 : 1<SP>1</SP> - diphenylmethane -2<SP>1</SP>- sulphonic acid (Specification 536,011) is condensed With 3:4-dichlorphenylisocyanate; other isocyanates, such as the2-,3-and 4-chlor-, 4-nitro-, 2:4- and 2:5- dichlor-, and 2:4:5- and 3:4:5- trichlorphenylisocyanate may be used ; (3) 2- amino-4:4<SP>1</SP>-dichlor-1:1<SP>1</SP>-diphenylether-2<SP>1</SP>-sul - phonic acid is condensed with 3:4-dichlorphenylcarbamic chloride ; a long list of other aminochlordiphenylether sulphonic acids which may be used is given; (4) 1-amino-3:4-dichlorbenzene-6-sulphonic acid is condensed with 3 : 4 - dichlorphenylcarbamic chloride ; (5) metanilic acid is condensed with 3-chlor-6- (41 - chlorplenoxy) - phenylcarbamic chloride (made from 2-amino-4:4<SP>1</SP>-dichlor-1:1<SP>1</SP>-diphenylether and phosgene) ; (6) m-aminobenzoyl-3:4- dichloraniline-6-sulphonic acid (made by condensing 3-nitrobenzoyl chloride with 1- amino - 3 : 4 - dichlorbenzene - 6 - sulphonic acid and reducing) is condensed with 3:4- dichlorphenylcarbamic chloride ; (7) 4-amino- 4<SP>1</SP>-amyl-1:1<SP>1</SP>-diphenylether-2-sulphonic acid is condensed with 3:4-dichlorphenyl isocyanate; a long list of other aminodiphenylether sulphonic acids which may be used is given, and (8) 2-amino-4:4<SP>1</SP>-dichlor-1<SP>1</SP>1<SP>1</SP>-diphenylether- 2<SP>1</SP>-sulphonic acid is condensed with 2:5-dichlorphenylcarbamic chloride or diphenylcarbamic chloride or N-laurylphenylearbamic chloride. Samples have been furnished under Sect. 2 (5) of the products from (1) 4-chlor-3<SP>1</SP>- aminodiphenyleneoxide sulphonic acid and 3:4-dichlorphenylcarbamic chloride; (2) 1- amino-3:4-dichlorbenzene-6-sulphonic acid and 4-chlor-3<SP>1</SP>-diphenyleneoxide-isocyanic ester ; (3) 3-aminophenothioxine sulphonic acid and 3 : 4 : 5 - trichlorphenyl isocyanate ; (4) phenothioxine isocyanate and 1-amino-3:4- dichlorbenzene - 6 - sulphonic acid ; and (5) 31- methyl - 4<SP>1</SP> - aminodiphenylether - 2 - sulphonic acid and.3 : 4 - dichlorphenyl isocyanate, the product being chlorinated.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH536047X | 1938-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB536047A true GB536047A (en) | 1941-04-30 |
Family
ID=4518772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB50/41A Expired GB536047A (en) | 1938-06-16 | 1939-06-15 | Process for the production of colourless halogen substituted urea sulphonic acids, and the resulting products |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH209163A (en) |
| DE (1) | DE764891C (en) |
| GB (1) | GB536047A (en) |
| NL (1) | NL62582C (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0318431B1 (en) * | 1987-11-24 | 1993-03-03 | Ciba-Geigy Ag | Protectant against moths and beetles |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE289107C (en) * |
-
0
- NL NL62582D patent/NL62582C/xx active
-
1938
- 1938-06-16 CH CH209163D patent/CH209163A/en unknown
- 1938-08-16 DE DEG98473D patent/DE764891C/en not_active Expired
-
1939
- 1939-06-15 GB GB50/41A patent/GB536047A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE764891C (en) | 1952-05-12 |
| NL62582C (en) | |
| CH209163A (en) | 1940-03-31 |
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