US2581057A - Blue-fluorescent dyestuffs - Google Patents
Blue-fluorescent dyestuffs Download PDFInfo
- Publication number
- US2581057A US2581057A US2581057DA US2581057A US 2581057 A US2581057 A US 2581057A US 2581057D A US2581057D A US 2581057DA US 2581057 A US2581057 A US 2581057A
- Authority
- US
- United States
- Prior art keywords
- parts
- blue
- mixture
- stilbene
- product
- 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 - Lifetime
Links
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000000835 fiber Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000004753 textile Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- CIXSDMKDSYXUMJ-UHFFFAOYSA-N N,N-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000002087 whitening Effects 0.000 description 6
- KVZUCOGWKYOPID-UHFFFAOYSA-N 2,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(OC)=C(C(O)=O)C=C1OC KVZUCOGWKYOPID-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 239000007844 bleaching agent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- -1 2,4,5 trimethoxy benzoylamino Chemical group 0.000 description 2
- REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(E)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 description 2
- VYBWECOQLZIGJZ-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)C1(CC(=C(C=C1)C(=C(C1=C(C=CC=C1)S(=O)(=O)O)N)N)S(=O)(=O)O)C(C1=CC=CC=C1)=O Chemical class C(C1=CC=CC=C1)(=O)C1(CC(=C(C=C1)C(=C(C1=C(C=CC=C1)S(=O)(=O)O)N)N)S(=O)(=O)O)C(C1=CC=CC=C1)=O VYBWECOQLZIGJZ-UHFFFAOYSA-N 0.000 description 2
- NDEXODWVYKOCFH-UHFFFAOYSA-L C(C1=CC=CC=C1)(=O)NC(=C(C1=C(C(=CC=C1)S(=O)(=O)[O-])S(=O)(=O)[O-])NC(C1=CC=CC=C1)=O)C1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)(=O)NC(=C(C1=C(C(=CC=C1)S(=O)(=O)[O-])S(=O)(=O)[O-])NC(C1=CC=CC=C1)=O)C1=CC=CC=C1 NDEXODWVYKOCFH-UHFFFAOYSA-L 0.000 description 2
- BNDRECGBDISUAI-UHFFFAOYSA-L C1(C(C=CC=C1)(S(=O)(=O)[O-])S(=O)(=O)[O-])C=CC1=CC=CC=C1 Chemical compound C1(C(C=CC=C1)(S(=O)(=O)[O-])S(=O)(=O)[O-])C=CC1=CC=CC=C1 BNDRECGBDISUAI-UHFFFAOYSA-L 0.000 description 2
- 206010010071 Coma Diseases 0.000 description 2
- BKKCHPZQDBOJLI-UHFFFAOYSA-N NC1=CC(C(C=C1)C=CC1=CC=C(C=C1)N)(S(=O)(=O)O)S(=O)(=O)O Chemical compound NC1=CC(C(C=C1)C=CC1=CC=C(C=C1)N)(S(=O)(=O)O)S(=O)(=O)O BKKCHPZQDBOJLI-UHFFFAOYSA-N 0.000 description 2
- 210000004940 Nucleus Anatomy 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000020127 ayran Nutrition 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
Classifications
-
- 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
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
- C07C39/215—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring containing, e.g. diethylstilbestrol
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/134—Brightener containing
Definitions
- Example 1 A mixture of 25 parts of 4,4'-diamino-stilbene- 2',2'-disulfonic acid, 36 parts of 2,4,5-trimethoxybenzoic acid, 14.1 parts of phosphorus oxychloride and 150 parts of pyridine is heated at reflux for minutes. At the end of this time the reaction completey'as shown by treatment of a small portion of'the reaction mixture with cold nitrous acid and alkaline R-salt; a purple 'color indicates incomplete reaction. The hot mixture is drowned into 1000 parts-of water and made just alkaline with 19.5 parts of sodium hydroxide.
- the drowned product is treated with 100 parts of salt, cooled to 25 C., filtered, Washed free of excess alkali with 5% salt solution and dried.
- the pale tan product, sodium-4,4-bis(2,4,5 trimethoxy benzoylamino) stilbene 2,2 disulfonate is substantive. to cellulosic fiber from an aqueous bath and imparts thereto a strong blue fluorescence.
- a mixture of 25 parts of 4,4'-diamino-stilbene- 2,2'disulfonic acid, 32 parts of 2,4,5-trimethoxybenzoic acid, 81.1 parts of diethyl-cyclohexylamine, 217 parts of xylene and 43 parts of toluene is distilled, approximately 72 parts of distillate being taken ofi so as to remove traces of water.
- the mixture is cooled to 100 C., 10 parts of phosphorus oxychloride are added and the resultant slurry is heated at reflux for 2 hours. This is followed by two additions of 1.7 parts and one addition of 0.8 part of phosphor-us oxychlo- OCH;
- the product in' the above two examples has been isolated as the sodium salt of the sulionic acid groups.
- the product may be obtained as the di-potassium sulionate. Isolation as the free disulfonic acids can be effected by acidification of the condensation mass, and the products thus obtained may be reacted with ammonium hydroxide or any suitable organic or inorganic base, to yield the corresponding salt.
- our novel compounds may also be used for various other purposes where fluorescence or absorption of ultra-violet light is desirable, for instance to achieve fluorescent efiects in costumes or stage settings, to achieve novel efiects onphotographic paper, as ultraviolet filters when impregnated on cellulosic fibers used for wrapping materials, etc.
- M stands for a member of the group consisting of hydrogen, the alkali-metals and ammonia.
Description
Patented Jan. 1, 1952 UNITED STATES PATENT OFF-ICE 2,581,057 BLUE-FLUORESCENT DYES'I'UFFS Walter Stanley Earl Krahler,
signers to E. L'du Pont de Nemours pany, Wilmington, Del.
ware
No Drawing. Original application Valentine Wirth, Woodstown, N. J.,. and
Wilmington, Del; as- & Coma' corporation of Dela- October 15,
1948, Serial No; 54,814. Divided and this ap plication October 25, 1949, Serial 2 Claims.
No, 54,814, filed 00170- zoyl nuclei with alkoxy groups;
It is an object of this invention to provide new cellulose-substantive, blue-fluorescent dyestuffs, which are useful particularly for imparting whiteness to textile materials and related cellulosic fibers. Other and further important objects of this invention will appear as the description proceeds.
In copending application Ser. No. 29,664 it is taught that 4,4-dibenzoyl-diamino-2,2'-disulfostilbenes which carry in each benzoyl ring two alkyloxy radicals'in the positions 3,4 are substantive to cellulose and are characterized particularly by a pronounced bluish fluorescence, when illuminated by ultra-violet light. Thus, the compounds are characterized tby absorption of light in theultra-violet spectrum, with at leastone absorption maximum within theregion o-f 3000 to 4000 angstrom units. When cellulosic material, for instance textile fabric or paper, is treated with an aqueous solution of one of these compounds and then exposed to ultra-violet radiation, the cellulosic material glows with a bluish fluorescence.
We have now found that whitening agents of even greater potency are obtained by selecting for the purpose a bis-benzoylamino-stilbene disulfonate carrying in each benzoyl nucleus 3 methoxy groups, which are disposed in positions 2,4,5, the position of the CONE group being counted as 1, and the benzoyl radical being free of other substituents. Expressed in different words, we have discovered new and superior bluefluorescents in a limited group of compounds characterized by the following structure:
HaCO
division from our I30 and 2,497,131, respectively,
is essentially No.v 123,542
both issued on February 14, 1950.
Without limiting our invention, the following examples are given to illustrate-our preferred mode of procedure. Parts mentioned are by Weight.
Example 1 A mixture of 25 parts of 4,4'-diamino-stilbene- 2',2'-disulfonic acid, 36 parts of 2,4,5-trimethoxybenzoic acid, 14.1 parts of phosphorus oxychloride and 150 parts of pyridine is heated at reflux for minutes. At the end of this time the reaction completey'as shown by treatment of a small portion of'the reaction mixture with cold nitrous acid and alkaline R-salt; a purple 'color indicates incomplete reaction. The hot mixture is drowned into 1000 parts-of water and made just alkaline with 19.5 parts of sodium hydroxide. The drowned product is treated with 100 parts of salt, cooled to 25 C., filtered, Washed free of excess alkali with 5% salt solution and dried. The pale tan product, sodium-4,4-bis(2,4,5 trimethoxy benzoylamino) stilbene 2,2 disulfonate, is substantive. to cellulosic fiber from an aqueous bath and imparts thereto a strong blue fluorescence.
Example 2 [Using a procedure as described in U. S. Patent No. 2,497,131.]
A mixture of 25 parts of 4,4'-diamino-stilbene- 2,2'disulfonic acid, 32 parts of 2,4,5-trimethoxybenzoic acid, 81.1 parts of diethyl-cyclohexylamine, 217 parts of xylene and 43 parts of toluene is distilled, approximately 72 parts of distillate being taken ofi so as to remove traces of water. The mixture is cooled to 100 C., 10 parts of phosphorus oxychloride are added and the resultant slurry is heated at reflux for 2 hours. This is followed by two additions of 1.7 parts and one addition of 0.8 part of phosphor-us oxychlo- OCH;
OCH:
ride, each of which is followed by 1 hours reflux. The mixture is refluxed for 2 hours longer, cooled to below C., diluted with 500 parts of water and steam distilled with addition of a suflicient amount of sodium hydroxide to release the diethyl cyclohexylamine from its salts. Practically all the xylene, toluene and diethyl cyclohexylamine are contained in the oil layer of the distillate. After cooling the mixture, the product is filtered, washed with brine and dried. The product is identical with that obtained in Example 1.
The product in' the above two examples has been isolated as the sodium salt of the sulionic acid groups. lieu of sodium hydroxide, the product may be obtained as the di-potassium sulionate. Isolation as the free disulfonic acids can be effected by acidification of the condensation mass, and the products thus obtained may be reacted with ammonium hydroxide or any suitable organic or inorganic base, to yield the corresponding salt.
Evaluation of the product of Examples 1 and 2 above on textile fiber has shown it to be a bluefiuorescent dye capable of imparting a stronger whitening efiect to cellulosic fibers than other By using potassium hydroxide in weights of the particular substances required to achieve a certain degree of whitening assumed as standard.
Study of the above data shows the superiority on a weight basis of the new compounds of this invention as whitening agents over those previously disclosed.
In addition to producing a whitening eiiect upon textile material, our novel compounds may also be used for various other purposes where fluorescence or absorption of ultra-violet light is desirable, for instance to achieve fluorescent efiects in costumes or stage settings, to achieve novel efiects onphotographic paper, as ultraviolet filters when impregnated on cellulosic fibers used for wrapping materials, etc.
We claim as ourinvention:
l. A compound of the general formula OCHa , I WQGONHQCMH NHGOQM.
CH: 03M 80M CH3 compounds of the benzoylamino-stilbene-disulionic acid group which have previously been disclosed in the patent literature.
The following comparisons were made on dyeings of various fluorescents on paper, by using the beater-dyeing technique and judging the dyed paper in diffuse daylight:
General formula:
The column marked Grams shows the wherein M stands for a member of the group consisting of hydrogen, the alkali-metals and ammonia.
2. 4,4'-bis(2,4,5 trimethoxy benzoylamino)- stilbene-2,2-di(sodium sulfonate) WALTER VALENTINE W'IRTH. STANLEY EARL KRAHLER.
Z CMH NMOQY I OzNB OzNS REFERENCES CITED UNITED STATES PATENTS Name Date Eberhart Apr. 26, 1949 Number
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2581057A true US2581057A (en) | 1952-01-01 |
Family
ID=3438602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2581057D Expired - Lifetime US2581057A (en) | Blue-fluorescent dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2581057A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2635113A (en) * | 1950-10-27 | 1953-04-14 | Du Pont | Manufacture of bis(alkoxy-benzamido)-stilbene-disulfonates |
| US2671790A (en) * | 1952-01-29 | 1954-03-09 | American Cyanamid Co | Acylation of aminosulfonic acids |
| US2676982A (en) * | 1951-06-08 | 1954-04-27 | Gen Aniline & Film Corp | Fluorescent agents |
| US2688617A (en) * | 1951-07-17 | 1954-09-07 | American Cyanamid Co | Sulfonated dihalogeno diaminostilbenes |
| US2700053A (en) * | 1948-10-15 | 1955-01-18 | Du Pont | Blue-fluorescent dyestuffs |
| US2877218A (en) * | 1953-12-30 | 1959-03-10 | American Cyanamid Co | Dyes from stilbene dicarboxylic acid amides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2468431A (en) * | 1948-04-29 | 1949-04-26 | American Cyanamid Co | o-alkoxybenzoyl derivatives of 4, 4'-diaminostilbene-2, 2'-disulfonic acid |
-
0
- US US2581057D patent/US2581057A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2468431A (en) * | 1948-04-29 | 1949-04-26 | American Cyanamid Co | o-alkoxybenzoyl derivatives of 4, 4'-diaminostilbene-2, 2'-disulfonic acid |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2700053A (en) * | 1948-10-15 | 1955-01-18 | Du Pont | Blue-fluorescent dyestuffs |
| US2635113A (en) * | 1950-10-27 | 1953-04-14 | Du Pont | Manufacture of bis(alkoxy-benzamido)-stilbene-disulfonates |
| US2676982A (en) * | 1951-06-08 | 1954-04-27 | Gen Aniline & Film Corp | Fluorescent agents |
| US2688617A (en) * | 1951-07-17 | 1954-09-07 | American Cyanamid Co | Sulfonated dihalogeno diaminostilbenes |
| US2671790A (en) * | 1952-01-29 | 1954-03-09 | American Cyanamid Co | Acylation of aminosulfonic acids |
| US2877218A (en) * | 1953-12-30 | 1959-03-10 | American Cyanamid Co | Dyes from stilbene dicarboxylic acid amides |
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