GB1071346A - Benzoxazole compounds and their use as optical brighteners - Google Patents
Benzoxazole compounds and their use as optical brightenersInfo
- Publication number
- GB1071346A GB1071346A GB20696/64A GB2069664A GB1071346A GB 1071346 A GB1071346 A GB 1071346A GB 20696/64 A GB20696/64 A GB 20696/64A GB 2069664 A GB2069664 A GB 2069664A GB 1071346 A GB1071346 A GB 1071346A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- aryl
- alkoxy
- hydrogen
- compounds
- 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
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title 1
- 230000003287 optical effect Effects 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 abstract 12
- 125000000217 alkyl group Chemical group 0.000 abstract 9
- 125000003545 alkoxy group Chemical group 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 3
- 239000003599 detergent Substances 0.000 abstract 3
- 125000001188 haloalkyl group Chemical group 0.000 abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 abstract 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 abstract 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 abstract 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 abstract 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000005642 Oleic acid Substances 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- -1 alkylaryl sulphonate Chemical compound 0.000 abstract 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 abstract 1
- 235000011130 ammonium sulphate Nutrition 0.000 abstract 1
- 239000001166 ammonium sulphate Substances 0.000 abstract 1
- 239000007844 bleaching agent Substances 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000002657 fibrous material Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 abstract 1
- 229940048086 sodium pyrophosphate Drugs 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 abstract 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 abstract 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 abstract 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
-
- 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
-
- 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
- D06L4/657—Optical bleaching or brightening combined with other treatments, e.g. finishing, bleaching, softening, dyeing or pigment printing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Detergent Compositions (AREA)
Abstract
Detergent compositions contain compounds of the formula <FORM:1071346/C4-C5/1> wherein R is hydrogen, alkyl, cycloalkyl, halogenoalkyl, hydroxyalkyl, alkoxyalkyl, N,N-dialkylamino alkyl, trialkylammonium alkyl, aryl or aralkyl, R1 is hydrogen, alkyl, alkoxy or aryl, R2 is alkyl, alkoxy or aryl or R1 and R2 together form an annulated aromatic or hydroaromatic nucleus for embellishing materials to be washed. In examples 4 and 5 detergent compositions specified are a mixture of an alkylaryl sulphonate, oleylaminooctaglycol ether, potassium pyrophosphate and the sodium salt of p-toluenesulphonic acid and a mixture of oleic acid methyl tauride, ammonium sulphate and sodium pyrophosphate.ALSO:The invention comprises compounds of the formula <FORM:1071346/C2/1> wherein R is hydrogen, alkyl, cycloalkyl, halogenoalkyl, hydroxyalkyl, alkoxyalkyl, N:N-dialkylaminoalkyl, trialkylammonium alkyl, aryl or aralkyl, R1 is hydrogen, alkyl, alkoxy or aryl, R2 is alkyl, alkoxy or aryl or R1 and R2 together stand for an annulated aromatic or hydroaromatic nucleus. They may be obtained by the reaction of substituted o-aminophenols or o-amino-naphthols with the acid chlorides of 2-, 3- or 4-carbalkoxycinnamic acids and subsequent heating of the N-acyl-compounds obtained in a solvent having a boiling point above 200 DEG C. in an atmosphere of an inert gas, optionally in the presence of a catalyst, e.g. zinc chloride.ALSO:Textile materials are optically brightened by treatment with a compound of the formula: <FORM:1071346/D1-D2/1> wherein R is hydrogen, alkyl, cycloalkyl, halogenoalkyl, hydroxyalkyl, alkoxyalkyl, N,N-dialkylamino alkyl, trialkylammonium-alkyl, aryl or aralkyl, R1 is hydrogen, alkyl, alkoxy or aryl, R2 is alkyl, alkoxy or aryl or R1 and R2 together form an annulated aromatic or hydroaromatic nucleus. Fibrous materials brightened may be made from polyethylene glycol terephthalate, polyamides, acetylated cellulose or polyacrylonitrile. The compounds may be used in the form of solutions in water or in organic solvents or in the form of dispersions, optionally in the presence of dispersants, and bleaching agents and detergents may be present.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0039765 | 1963-05-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1071346A true GB1071346A (en) | 1967-06-07 |
Family
ID=7097929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB20696/64A Expired GB1071346A (en) | 1963-05-17 | 1964-05-19 | Benzoxazole compounds and their use as optical brighteners |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE648091A (en) |
| CH (2) | CH454079A (en) |
| DE (1) | DE1444014A1 (en) |
| DK (1) | DK112023B (en) |
| FR (1) | FR1397629A (en) |
| GB (1) | GB1071346A (en) |
| NL (1) | NL142207B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140091283A1 (en) * | 2012-09-28 | 2014-04-03 | Polyera Corporation | Semiconducting Compounds and Optoelectronic Devices Incorporating Same |
-
1963
- 1963-05-17 DE DE19631444014 patent/DE1444014A1/en active Pending
-
1964
- 1964-05-12 NL NL646405251A patent/NL142207B/en unknown
- 1964-05-14 CH CH1628165A patent/CH454079A/en unknown
- 1964-05-14 CH CH628064A patent/CH438202A/en unknown
- 1964-05-14 DK DK243164AA patent/DK112023B/en unknown
- 1964-05-19 BE BE648091A patent/BE648091A/xx unknown
- 1964-05-19 GB GB20696/64A patent/GB1071346A/en not_active Expired
- 1964-05-19 FR FR974900A patent/FR1397629A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140091283A1 (en) * | 2012-09-28 | 2014-04-03 | Polyera Corporation | Semiconducting Compounds and Optoelectronic Devices Incorporating Same |
| US9312501B2 (en) * | 2012-09-28 | 2016-04-12 | Polyera Corporation | Semiconducting compounds and optoelectronic devices incorporating same |
Also Published As
| Publication number | Publication date |
|---|---|
| CH1628165A4 (en) | 1967-12-29 |
| CH454079A (en) | 1968-06-14 |
| CH628064A4 (en) | 1967-03-15 |
| CH438202A (en) | 1967-11-30 |
| NL6405251A (en) | 1964-11-18 |
| FR1397629A (en) | 1965-04-30 |
| DK112023B (en) | 1968-11-04 |
| BE648091A (en) | 1964-11-19 |
| NL142207B (en) | 1974-05-15 |
| DE1444014A1 (en) | 1969-12-04 |
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