GB654028A - Manufacture of brightening agents for textile and other organic fibrous materials - Google Patents
Manufacture of brightening agents for textile and other organic fibrous materialsInfo
- Publication number
- GB654028A GB654028A GB27624/48A GB2762448A GB654028A GB 654028 A GB654028 A GB 654028A GB 27624/48 A GB27624/48 A GB 27624/48A GB 2762448 A GB2762448 A GB 2762448A GB 654028 A GB654028 A GB 654028A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloride
- reacted
- nitroaminostilbene
- reduced
- ammonia
- 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
- 238000005282 brightening Methods 0.000 title abstract 2
- 239000004753 textile Substances 0.000 title abstract 2
- 239000002657 fibrous material Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 20
- 239000002253 acid Substances 0.000 abstract 12
- 229910021529 ammonia Inorganic materials 0.000 abstract 10
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 6
- 150000002828 nitro derivatives Chemical class 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 239000000047 product Substances 0.000 abstract 5
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 abstract 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 4
- 239000007859 condensation product Substances 0.000 abstract 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 3
- 235000019253 formic acid Nutrition 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 3
- 125000001302 tertiary amino group Chemical group 0.000 abstract 3
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 abstract 2
- ABYSGRXBGLVRGO-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetyl chloride Chemical compound CC1=CC(Cl)=CC=C1OCC(Cl)=O ABYSGRXBGLVRGO-UHFFFAOYSA-N 0.000 abstract 2
- VRBVHQUSAOKVDH-UHFFFAOYSA-N 2-(4-chlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1 VRBVHQUSAOKVDH-UHFFFAOYSA-N 0.000 abstract 2
- SBSYFELXUYBRND-UHFFFAOYSA-N 3-phenoxypropanoyl chloride Chemical compound ClC(=O)CCOC1=CC=CC=C1 SBSYFELXUYBRND-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 2
- 229910052742 iron Inorganic materials 0.000 abstract 2
- 239000004677 Nylon Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- -1 halogen 1,3,5-triazine compound Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229920001778 nylon Polymers 0.000 abstract 1
- 238000009994 optical bleaching Methods 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Coloring (AREA)
Abstract
Compounds of the general formula <FORM:0654028/IV (b)/1> (in which Ar is an aromatic radical and Y is the radical of a 1,3,5-triazine ring which may be substituted in the 3,5-positions by primary, secondary or tertiary amino groups) are prepared by reacting 4,41-diaminostilbene compounds, mono-acylated by the Ar-O-alkylene-CO-group, with a halogen 1,3,5-triazine compound and, if desired, replacing further halogen atoms of the 1,3,5-traizine ring by primary, secondary or tertiary amino groups. Alternatively, an N-mono-1,3,5-triazinyl derivative of a 4,41-diaminostilbene is acylated to introduce the Ar-O-alkylene-CO-grouping. Compounds containing free amino groups may then be treated with formaldehyde as described in Specification 595,065. In examples: (1) the nitro-compound prepared by condensing 4,41-nitroaminostilbene-2,21-disulphonic acid with cyanuric chloride is reacted with concentrated ammonia, dimethylamine or diethanolamine, reduced with iron and hydrochloric acid, and then reacted with phenoxyacetyl chloride; (2) the nitro compound obtained by condensing 4,41 - nitroaminostilbene - 2,21 - disulphonic acid with aniline is reduced and then reacted with phenoxyacetyl chloride; (3) cyanuric chloride, 4,41 - nitroaminostilbene - 2,21 - disulphonic acid and ammonia are condensed and reduced, and the product reacted with p-cresoxyacetyl chloride; (4) the nitro compound obtained by condensing 4,41 - nitroaminostilbene - 2,21 - disulphonic acid with 4-chlorophenoxyacetyl chloride is reduced and reacted with cyanuric chloride and ammonia; (5) the reduced condensation product from cyanuric chloride, 4,41-nitroaminostilbene-2,21-disulphonic acid and ammonia is reacted with 4-chloro-2-methyl-phenoxyacetyl chloride; and (6) the condensation product from cyanuric chloride, 4,41-nitroaminostilbene-2,21-disulphonic acid and ammonia is reduced and reacted with phenoxypropionyl chloride. Many other compounds within the scope of the general formula are specified.ALSO:Compounds of the general formula <FORM:0654028/IV (c)/1> (in which Ar is an aromatic radical and Y is the radical of a 1,3,5-triazine ring which may be substituted in the 3,5-positions by primary, secondary or tertiary amino groups) are used for optical bleaching and for imparting a brilliance to dyed textile materials. Compounds containing free amino groups may be treated with formaldehyde as described in Specification 595,065. In examples : (1) the nitro-compound prepared by condensing 4,41 nitroaminostilbene-2,21-disulphonic acid with cyanuric chloride is reacted with concentrated ammonia, dimethylamine or diethanolamine, reduced with iron and hydrochloric acid, and then reacted with phenoxy-acetyl chloride ; (2) the nitro compound obtained by condensing 4,41 - nitroaminostilbene - 2,21 - disulphonic acid with aniline is reduced and then reacted with phenoxyacetyl chloride ; (3) cyanuric chloride, 4,41 - nitroaminostilbene - 2,21 - disulphonic acid and ammonia are condensed, reduced, and the product reacted with p-cresoxyacetyl chloride ; (4) the nitro compound obtained by condensing 4,41-nitroaminostilbene-2,21-disulphonic acid with 4-chlorophenoxyacetyl chloride is reduced and reacted with cyanuric chloride and ammonia; (5) the reduced condensation product from cyanuric chloride, 4,41 - nitroaminostilbene - 2,21 - disulphonic acid and ammonia is reacted with 4 - chloro - 2 - methyl - phenoxyacetyl chloride ; (6) the condensation product from cyanuric chloride, 4,41 - nitroaminostilbene - 2,21-disulphonic acid and ammonia is reduced and reacted with phenoxypropionyl chloride ; (7) silk is brightened by treatment with the product of (1) in presence of formic acid; (8) nylon is brightened by treatment with the product of (2) in presence of formic acid, and (9) bleached wool is dyed with Alizarin Light Blue AR in the presence of the product of (2) and formic acid. Many other brightening agents within the scope of the general formula are specified.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH654028X | 1947-10-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB654028A true GB654028A (en) | 1951-05-30 |
Family
ID=4526363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27624/48A Expired GB654028A (en) | 1947-10-24 | 1948-10-23 | Manufacture of brightening agents for textile and other organic fibrous materials |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB654028A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1026274B (en) * | 1954-10-25 | 1958-03-20 | Bayer Ag | Optical brighteners |
-
1948
- 1948-10-23 GB GB27624/48A patent/GB654028A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1026274B (en) * | 1954-10-25 | 1958-03-20 | Bayer Ag | Optical brighteners |
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