CH450421A - Verfahren zur Herstellung von Azolyl-thiophenverbindungen - Google Patents

Verfahren zur Herstellung von Azolyl-thiophenverbindungen

Info

Publication number: CH450421A
Authority: CH; Switzerland
Prior art keywords: compounds; formula; radical; preparation; carboxyl group
Prior art date: 1962-12-21

Application number

CH1505862A

Other languages

German (de)

English (en)

Inventor

Erwin Dr Maeder

Peter Dr Liechti

Emil Dr Siegrist Adolf

Original Assignee

Ciba Geigy

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.)

1962-12-21

Filing date

1962-12-21

Publication date

1968-01-31

Priority to BE620372D priority Critical patent/BE620372A/fr

Priority to NL302367D priority patent/NL302367A/xx

Priority to NL281101D priority patent/NL281101A/xx

Priority to NL122317D priority patent/NL122317C/xx

1962-06-19 Priority to CH379364A priority patent/CH443664A/de

1962-07-13 Priority to FR903875A priority patent/FR1335174A/fr

1962-07-18 Priority to GB27631/62A priority patent/GB990397A/en

1962-07-18 Priority to DE1962C0027492 priority patent/DE1238873B/de

1962-12-21 Application filed by Ciba Geigy filed Critical Ciba Geigy

1962-12-21 Priority to CH1505862A priority patent/CH450421A/de

1963-11-25 Priority to DE1444006A priority patent/DE1444006C3/de

1963-11-27 Priority to GB4693863A priority patent/GB1016365A/en

1963-12-04 Priority to US328112A priority patent/US3264315A/en

1963-12-04 Priority to US328058A priority patent/US3328310A/en

1963-12-16 Priority to FR957342A priority patent/FR84935E/fr

1963-12-18 Priority to SE14131/63A priority patent/SE300603B/xx

1963-12-20 Priority to ES294732A priority patent/ES294732A2/es

1963-12-20 Priority to BE641607D priority patent/BE641607A/xx

1963-12-20 Priority to AT1028663A priority patent/AT243739B/de

1968-01-31 Publication of CH450421A publication Critical patent/CH450421A/de

Links

238000000034 method Methods 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 5
XCJMGRZQOXNTRE-UHFFFAOYSA-N 2-thiophen-2-yl-1h-pyrrole Chemical class C1=CNC(C=2SC=CC=2)=C1 XCJMGRZQOXNTRE-UHFFFAOYSA-N 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 5
AVRAFQYKQWOZHV-UHFFFAOYSA-N 2-thiophen-2-yl-1,3-oxazole Chemical class C1=CSC(C=2OC=CN=2)=C1 AVRAFQYKQWOZHV-UHFFFAOYSA-N 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
150000001735 carboxylic acids Chemical class 0.000 claims description 3
150000002763 monocarboxylic acids Chemical class 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
229930192474 thiophene Natural products 0.000 claims description 3
150000001805 chlorine compounds Chemical class 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
239000000463 material Substances 0.000 claims description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 5
125000002843 carboxylic acid group Chemical group 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000004952 Polyamide Substances 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
239000000835 fiber Substances 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
229920002647 polyamide Polymers 0.000 description 3
229920000728 polyester Polymers 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000009987 spinning Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
UZLSJAUHCCPJMC-UHFFFAOYSA-N 2-thiophen-2-yl-1h-imidazole Chemical class C1=CSC(C=2NC=CN=2)=C1 UZLSJAUHCCPJMC-UHFFFAOYSA-N 0.000 description 1
QGMFBCDNJUZQBZ-UHFFFAOYSA-N 5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CC=C1 QGMFBCDNJUZQBZ-UHFFFAOYSA-N 0.000 description 1
UFFRSDWQMJYQNE-UHFFFAOYSA-N 6-azaniumylhexylazanium;hexanedioate Chemical compound [NH3+]CCCCCC[NH3+].[O-]C(=O)CCCCC([O-])=O UFFRSDWQMJYQNE-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
VNQABZCSYCTZMS-UHFFFAOYSA-N Orthoform Chemical compound COC(=O)C1=CC=C(O)C(N)=C1 VNQABZCSYCTZMS-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000003943 azolyl group Chemical group 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
150000001733 carboxylic acid esters Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
-1 ethylene glycol ester Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000009998 heat setting Methods 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000002087 whitening effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/06—Dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
General Chemical & Material Sciences (AREA)
Manufacturing & Machinery (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Polyamides (AREA)
Artificial Filaments (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CH1505862A 1961-07-19 1962-12-21 Verfahren zur Herstellung von Azolyl-thiophenverbindungen CH450421A (de)

Priority Applications (18)

Application Number	Priority Date	Filing Date	Title
BE620372D BE620372A (es)	1961-07-19
NL302367D NL302367A (es)	1961-07-19
NL281101D NL281101A (es)	1961-07-19
NL122317D NL122317C (es)	1961-07-19
CH379364A CH443664A (de)	1961-07-19	1962-06-19	Verwendung von neuen Azolyl-thiophenderivaten als optische Aufhellmittel für nicht-textile organische Materialien
FR903875A FR1335174A (fr)	1961-07-19	1962-07-13	Nouveaux azolyl-thiofènes utilisables comme éclaircissants optiques et procédé pour les préparer
GB27631/62A GB990397A (en)	1961-07-19	1962-07-18	New azolylthiophene compounds useful as optical brightening agents and process for their production
DE1962C0027492 DE1238873B (de)	1961-07-19	1962-07-18	Optische Aufhellmittel
CH1505862A CH450421A (de)	1962-12-21	1962-12-21	Verfahren zur Herstellung von Azolyl-thiophenverbindungen
DE1444006A DE1444006C3 (de)	1961-07-19	1963-11-25	Verwendung von Azolyl-thiophenverbindungen als optische Aufhellmittel für organische Materialien
GB4693863A GB1016365A (en)	1961-07-19	1963-11-27	New azolyl-thiophene derivatives, process for their preparation and their use
US328112A US3264315A (en)	1961-07-19	1963-12-04	Azolyl-thiophene compounds
US328058A US3328310A (en)	1961-07-19	1963-12-04	Optically brightened organic compositions
FR957342A FR84935E (fr)	1961-07-19	1963-12-16	Nouveaux azolyl-thiophènes utilisables comme éclaircissants optiques et procédé pour les préparer
SE14131/63A SE300603B (es)	1961-07-19	1963-12-18
ES294732A ES294732A2 (es)	1962-12-21	1963-12-20	Procedimiento para la aclaración óptica de materiales orgánicos
BE641607D BE641607A (es)	1961-07-19	1963-12-20
AT1028663A AT243739B (de)	1962-12-21	1963-12-20	Optische Aufhellmittel

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1505862A CH450421A (de)	1962-12-21	1962-12-21	Verfahren zur Herstellung von Azolyl-thiophenverbindungen

Publications (1)

Publication Number	Publication Date
CH450421A true CH450421A (de)	1968-01-31

Family

ID=4405989

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1505862A CH450421A (de)	1961-07-19	1962-12-21	Verfahren zur Herstellung von Azolyl-thiophenverbindungen

Country Status (3)

Country	Link
AT (1)	AT243739B (es)
CH (1)	CH450421A (es)
ES (1)	ES294732A2 (es)

1962
- 1962-12-21 CH CH1505862A patent/CH450421A/de unknown
1963
- 1963-12-20 ES ES294732A patent/ES294732A2/es not_active Expired
- 1963-12-20 AT AT1028663A patent/AT243739B/de active

Also Published As

Publication number	Publication date
ES294732A2 (es)	1964-05-16
AT243739B (de)	1965-11-25

Publication	Publication Date	Title
DE1793482C3 (de)	1975-09-25	Neue Bis-stilbenverbindungen und Verfahren zu deren Herstellung
DE2238734A1 (de)	1973-02-22	Benzofuran-derivate, verfahren zu deren herstellung und verwendung als optische aufheller
DE1444006C3 (de)	1974-03-07	Verwendung von Azolyl-thiophenverbindungen als optische Aufhellmittel für organische Materialien
CH450421A (de)	1968-01-31	Verfahren zur Herstellung von Azolyl-thiophenverbindungen
DE1594835A1 (de)	1971-01-28	Neue Tolanderivate und deren Verwendung als optische Aufhellmittel
DE2247791A1 (de)	1973-04-12	Optische aufhellmittel
DE1281385B (de)	1968-10-24	Optische Aufheller
DE1958607A1 (de)	1970-06-11	Optische Aufheller
CH450342A (de)	1968-01-31	Verwendung von neuen Thiophenderivaten als optische Aufhellmittel ausserhalb der Textilindustrie
DE2258276C3 (de)	1981-08-13	Triazolyl-stilbene, sowie deren Herstellung und Verwendung als optische Aufheller
DE1670888C2 (de)	1984-06-14	1,4-Bis-Benzoxazolylnaphthalin-dicarbonsäuren und ihre Verwendung
CH442216A (de)	1967-08-31	Verfahren zum optischen Aufhellen von nicht-textilen organischen Materialien
DE2213839B2 (de)	1981-05-14	2-Stilbenyl-4-styryl-v-triazole und deren Verwendung zum optischen Aufhellen von organischen Materialien
DE1745622C2 (de)	1983-04-14	1,4-Bis-benzoxazolyl-naphthalin-dicarbonsäureester, Verfahren zu deren Herstellung und deren Verwendung als optische Aufheller
CH617669A5 (es)	1980-06-13
AT257530B (de)	1967-10-10	Optisches Aufhellmittel für organische Materialien
CH530439A (de)	1972-11-15	Verwendung von heterocyclisch substituierten Vinyl-v-triazolen der Cumarinreihe zum Aufhellen von nichttextilen organischen Materialien
DE2306515A1 (de)	1974-08-15	Benzo-difuran-verbindungen
CH561708A5 (en)	1975-05-15	Triazolylstyrene cpds - useful as polymer brighteners
AT273106B (de)	1969-08-11	Verfahren zur Herstellung von neuen Benzoxazolverbindungen
AT235234B (de)	1964-08-10	Optische Aufhellungsmittel
CH347188A (de)	1960-06-30	Verfahren zur Herstellung neuer a,B-Di-(benzoxazolyl-(2))-äthylene
EP0042536A1 (de)	1981-12-30	Benzoxazolyldihydronaphthothiophenverbindungen sowie deren Verwendung als optische Aufheller
CH647774A5 (en)	1985-02-15	Organic compounds and preparation and use thereof
DE1040555B (de)	1958-10-09	Verfahren zur Herstellung neuer, optisch aufhellend wirkender ª‡,ª‰-Di-[benzoxazolyl-(2)]-aethylene