US2840557A - Oo-nhj - Google Patents
Oo-nhj Download PDFInfo
- Publication number
- US2840557A US2840557A US2840557DA US2840557A US 2840557 A US2840557 A US 2840557A US 2840557D A US2840557D A US 2840557DA US 2840557 A US2840557 A US 2840557A
- Authority
- US
- United States
- Prior art keywords
- materials
- parts
- fluorescent
- whiter
- fabrics
- 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
- 239000000203 mixture Substances 0.000 claims description 26
- 239000000463 material Substances 0.000 description 80
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 18
- 239000004744 fabric Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000003599 detergent Substances 0.000 description 12
- 239000000344 soap Substances 0.000 description 12
- 239000004753 textile Substances 0.000 description 12
- 238000005282 brightening Methods 0.000 description 10
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 235000020127 ayran Nutrition 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000007850 fluorescent dye Substances 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 229940113083 morpholine Drugs 0.000 description 8
- -1 morpholino, dimethylamino, diethylamino Chemical group 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 6
- 239000001913 cellulose Substances 0.000 description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 4
- 210000002268 Wool Anatomy 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 4
- 239000007844 bleaching agent Substances 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide group Chemical group NNC(=O)N DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000001187 sodium carbonate Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- TXVWTOBHDDIASC-UHFFFAOYSA-N 1,2-diphenylethene-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)=C(N)C1=CC=CC=C1 TXVWTOBHDDIASC-UHFFFAOYSA-N 0.000 description 2
- VERUFXOALATMPS-UHFFFAOYSA-N 5,5-diamino-2-(2-phenylethenyl)cyclohex-3-ene-1,1-disulfonic acid Chemical compound C1=CC(N)(N)CC(S(O)(=O)=O)(S(O)(=O)=O)C1C=CC1=CC=CC=C1 VERUFXOALATMPS-UHFFFAOYSA-N 0.000 description 2
- XDVZFVQLRRGUKX-UHFFFAOYSA-N 5,5-diamino-2-[2-(2-sulfophenyl)ethenyl]cyclohexa-1,3-diene-1-sulfonic acid Chemical compound C1=CC(N)(N)CC(S(O)(=O)=O)=C1C=CC1=CC=CC=C1S(O)(=O)=O XDVZFVQLRRGUKX-UHFFFAOYSA-N 0.000 description 2
- 229940040526 Anhydrous Sodium Acetate Drugs 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N Cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Dichlothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XHQYBDSXTDXSHY-UHFFFAOYSA-N Semicarbazide hydrochloride Chemical compound Cl.NNC(N)=O XHQYBDSXTDXSHY-UHFFFAOYSA-N 0.000 description 2
- 229940105648 Soma Drugs 0.000 description 2
- 229940055764 Triaz Drugs 0.000 description 2
- 241000933336 Ziziphus rignonii Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000003973 alkyl amines Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229910001919 chlorite Inorganic materials 0.000 description 2
- 229910052619 chlorite group Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000295 complement Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- 239000000049 pigment 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
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 230000002087 whitening Effects 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/68—Triazinylamino stilbenes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0208—Tissues; Wipes; Patches
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/08—Preparations for bleaching the hair
Definitions
- fluorescent agents While a wide variety of fluorescent agents have been suggested for treatment of fibrous materials, it has been found that for the treatment of cellulosic materials, either paper or textiles, the use of fluorescent agents which are substantive to cellulose is preferable since by'the use of substantive fluorescent agents a whitening or brightening the material so that after drying the material appears much whiter and brighter than untreated materials.
- fluorescent brightening agents are also useful in treating textile materials which are to be, or have been dyed or printed withdischarge paste.
- the whites of the materials so printed with pastes containing brightening agents are much whiter than is otherwise the case.
- the whites obtained upon discharge are decidedly whiter than those discharges made in the abfabrics.
- the fluorescent agent must be stable to light and notdiscolor on exposure. ,It must be stable to hyp'o-chlorite treatment,andnotj discolor under suchtreatment, and in addition, it must fluoresce overa fairly wide pH differential, including both alkali and acid.
- the present invention presents a series of compounds which have some of the characteristics of dyestuffs or pigments, which in addition show a strong bluish white fiuoresence of out-standing brilliance, which compounds in addition are readily incorporated into a wide range. of fabrics, fibers, felted materials and paper, to yield an outstanding whiteness in the material to which they are applied.
- This material is a triazinostilbene compound containing a semicarbazide group with an associated alkyl amino group. Broadly the compound has the following molecular structure:
- X is selected from the group consisting of morpholino, dimethylamino, diethylamino or di-(hydroxyethynamino substituents.
- a w a I This compound, and a considerable group of analogous compounds, are readily preparedby condensingl molecular proportion of 4,4-diamino-2,2'-stilbene-disulfonic acid with 2 molecular proportions of cyanuric chloride.
- the primary condensation product can be :further condensed with 2 molecular proportions of semi-carbazide hydrochloride and finally with 2 molecular proportions of morpholine, dimethylamine, diethylamine or diethanolamine.
- These materials are particularly useful for application to paper or fabrics or other sheet or wrapping material to 5 improve the whiteness thereof. They are useful when applied to fabrics by methods well known in the art since the whiteness is remarkably improved.
- the white backimproved by incorporating some of the material into the By addition of the substances to dissence of said materials. If small quantities of these materials are used in soaps or other detergents, fabrics which are washed using these formulations will be much whiter in the case of whites and much brighter 'in the case'of colors th an fabrics which are washed with ordinary soaps or detergents. These materials may be usedto bleach In such cases, the amount of bleach necessary is materially reduced and one or more steps in the normal bleaching operation may be eliminated. 7
- the product of the invention outstandingly increases the apparent whiteness of a wide range of surfacing materials by the incorporationathereinto of a dye 3 type substance of the triazinostilbene series containing a semicarbazide group and an alkyl amine substituent.
- Example I Thirty-seven parts of'cyanuric' chloride are dissolved in 120 parts of acetone and poured into a mixture of ice and water; During the suspension in ice water, the temperatureof the aqueous suspension should not rise above 5 C. Thirty-seven parts of 4,4-diaminostilbene-2,2-disulfonic acid are dissolved in 150 parts of water with the additionof enough sodium carbonate to give a neutral The materialwhich is obtained is slightly tan in color and moderately soluble in water but very slightly soluble in acetone, alcohol, ether, etc.
- Example 11 The procedure of Example I was repeated up to and including the end of the secondary condensation whereupon, instead of adding 56 parts of morpholine, 142 parts of a 33% aqueous solution of dimethylamine were added and the pH increased to 7.5 to 7.8 with sodium carbonate solution. Then the mixture was heated slowly to 65 C. and maintained at that temperature for 8 hours, as before. Upon cooling and separating the product a material was obtained corresponding to the formula:
- the material which is obtained is slightly tan in color and moderately soluble in water but very slightly soluble in acetone, alcohol, ether and the like.
- Example Ill The procedure of Example I was repeated up to and including the secondary condensation; then instead of adding. 56 parts of morpholine, 73 parts of diethylamine were addedand the material neutralized and heated as be fore to yield a product corresponding to the formula:
- the material which is obtained is slightly tan in color and moderately soluble in water but very slightly soluble in acetone, alcohol, ether and the like.
- Example IV The procedure of Example I was repeated, as before,
- a whitener having the composition:
- the white materials thus washed are extraordinarily whiter in appearance and colored materials are brighter than similar materials 35 ethyl)-arnino.
- X is selected from the group consisting of morpholinyl, dimethylamino, diethylamino and di-(hydroxy- 1 TH N'HC ONH: in in;
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Biomedical Technology (AREA)
- Coloring (AREA)
Description
United States Patent FLUORESCENT AGENT William W. Williams, NeW York, N. Y., and William H.
' detergents, the fluorescent material which is employed Libby, St. Paul, Minn., assignors to General Aniline'&
Film Corporation, New York, N. Y., a corporation of Delaware 1 No Drawin Application March 30, 1950 Serial No. 575,000
5 cl ims. (Cl. 260-2471) The invention here presented is anew whitener in the form of a dye type of substance which is fluorescent under ultra violet to yield a brilliant bluish white fluorescence, which agent is found in the triaz inostilbene series. a
It is well known that cellulosic materials such as paper, cotton textiles and the like have a slight yellowish hue which, particularly in the case of textile materials, is apt to become more pronounced when the material is subjected to repeated launderings and use. Accordingly, it has long been the practice to treat many white cotton textiles, when they are washed, with a bluing substance, such as ultramarine. It has been'found that the slight blue coloration thus imparted to the material compensates for the yellowish tint or similar off-white shade of the material so that it appears whiter; such bluing operations, however, result in the absorption of a measurable portion of the total visible light falling upon the treated material and, accordingly, the treated material has a silghtly dull appearance. 7 I It has recently been proposed to treat paper or cotton textiles and similar cellulosic materials with agents which, while themselves colorless, fluoresce in the blue range of the spectrum so that in daylight or other light, which includes ultra violet radiation, the fluorescence of the treating agent compensates for the slight yellowish tint or similar oil-white shade, the blue'being complementary to yellow. Such fluorescent agents only absorb, a negligible portion of the visible light falling on the material and, accordingly, as a result-of the fluorescence the treated material is much brighter as well as whiter in appearance.
While a wide variety of fluorescent agents have been suggested for treatment of fibrous materials, it has been found that for the treatment of cellulosic materials, either paper or textiles, the use of fluorescent agents which are substantive to cellulose is preferable since by'the use of substantive fluorescent agents a whitening or brightening the material so that after drying the material appears much whiter and brighter than untreated materials.
These fluorescent brightening agents are also useful in treating textile materials which are to be, or have been dyed or printed withdischarge paste. The whites of the materials so printed with pastes containing brightening agents are much whiter than is otherwise the case.
While numerous fluorescent bleaching or brightening agents have heretofore been suggested, including diaminostilbene sulfonic and carhoxylic acids and certain acylated derivatives thereof, only a few of them have been satis factory, particularly for use by incorporation in soap or other detergents. Inorder to be satisfactory for use as a brightening agentto be incorporated with soap or similar ground of photographic prints and diazotype prints can be i coating emulsions.
. charge pastes, the whites obtained upon discharge are decidedly whiter than those discharges made in the abfabrics.
should be itself colorless, or nearly so, and must not stain yellow tints to thetreated fabric. It must also have a proper degree of substantivity towards the materials as too small adegree of substantivity renders it valueless as if would be'removed in any rinse waters, and too high a degree of substantivity results in a gradual build-up of fluorescent agent on material during repeated launderings resulting in off-color shades. The fluorescent agent must be stable to light and notdiscolor on exposure. ,It must be stable to hyp'o-chlorite treatment,andnotj discolor under suchtreatment, and in addition, it must fluoresce overa fairly wide pH differential, including both alkali and acid. W The present invention presents a series of compounds which have some of the characteristics of dyestuffs or pigments, which in addition show a strong bluish white fiuoresence of out-standing brilliance, which compounds in addition are readily incorporated into a wide range. of fabrics, fibers, felted materials and paper, to yield an outstanding whiteness in the material to which they are applied. .This material is a triazinostilbene compound containing a semicarbazide group with an associated alkyl amino group. Broadly the compound has the following molecular structure:
X 2 K N C-NH- CH: C=N S O 3N8.
111a 1 TH C O NH: 2
Where X is selected from the group consisting of morpholino, dimethylamino, diethylamino or di-(hydroxyethynamino substituents. A w a I This compound, and a considerable group of analogous compounds, are readily preparedby condensingl molecular proportion of 4,4-diamino-2,2'-stilbene-disulfonic acid with 2 molecular proportions of cyanuric chloride. The primary condensation product can be :further condensed with 2 molecular proportions of semi-carbazide hydrochloride and finally with 2 molecular proportions of morpholine, dimethylamine, diethylamine or diethanolamine.
These materials are particularly useful for application to paper or fabrics or other sheet or wrapping material to 5 improve the whiteness thereof. They are useful when applied to fabrics by methods well known in the art since the whiteness is remarkably improved. The white backimproved by incorporating some of the material into the By addition of the substances to dissence of said materials. If small quantities of these materials are used in soaps or other detergents, fabrics which are washed using these formulations will be much whiter in the case of whites and much brighter 'in the case'of colors th an fabrics which are washed with ordinary soaps or detergents. These materials may be usedto bleach In such cases, the amount of bleach necessary is materially reduced and one or more steps in the normal bleaching operation may be eliminated. 7
Thus the product of the invention outstandingly increases the apparent whiteness of a wide range of surfacing materials by the incorporationathereinto of a dye 3 type substance of the triazinostilbene series containing a semicarbazide group and an alkyl amine substituent.
cooled and the product is separated in the usual manner. It corresponds to the formula:
other' objects' and details of theinvention will be apparent from thefollowing description.
" The following examples show the preferred method of practising the invention but various modifications will be obvious to those skilled in the art.
Example I Thirty-seven parts of'cyanuric' chloride are dissolved in 120 parts of acetone and poured into a mixture of ice and water; During the suspension in ice water, the temperatureof the aqueous suspension should not rise above 5 C. Thirty-seven parts of 4,4-diaminostilbene-2,2-disulfonic acid are dissolved in 150 parts of water with the additionof enough sodium carbonate to give a neutral The materialwhich is obtained is slightly tan in color and moderately soluble in water but very slightly soluble in acetone, alcohol, ether, etc.
Example 11 The procedure of Example I was repeated up to and including the end of the secondary condensation whereupon, instead of adding 56 parts of morpholine, 142 parts of a 33% aqueous solution of dimethylamine were added and the pH increased to 7.5 to 7.8 with sodium carbonate solution. Then the mixture was heated slowly to 65 C. and maintained at that temperature for 8 hours, as before. Upon cooling and separating the product a material was obtained corresponding to the formula:
The material which is obtained is slightly tan in color and moderately soluble in water but very slightly soluble in acetone, alcohol, ether and the like.
Example Ill The procedure of Example I was repeated up to and including the secondary condensation; then instead of adding. 56 parts of morpholine, 73 parts of diethylamine were addedand the material neutralized and heated as be fore to yield a product corresponding to the formula:
N-omon,
partstof semicarba'zide hydrochloride is added and immediately, afterward a solution of 160 parts of anhydrous sodium acetate in 400 parts of water is added. The mixture is allowed to warm to room temperature and may be heated to 35-40 C. ifnecessary to complete the condensation. When this secondary, condensation is complete, 56 parts of morpholineare added and the pH is increased to 7.5-8 with sodium carbonatesolution. Then the mixture is heated slowly to f C. and maintained SOrN SOxNa NCH:CH;
The material which is obtained is slightly tan in color and moderately soluble in water but very slightly soluble in acetone, alcohol, ether and the like.
Example IV The procedure of Example I was repeated, as before,
up to and including the secondary condensation; then instead of the 56 parts of morpholine, there were added at that temperature for 8 hours. The mixture is then 68 parts of diethanolamine, after which, the processing shown in Example I was repeated to yield a compound having the formula:
C-N some N=C soma N-CHiCHflOH N -ornomon mcrnon The material which is obtained is slightly tan in color a l embodiments of 'theprocess of the invention it is possible and moderately soluble in water but very slightly soluble to provide still other embodiments without departing from in acetone, alcohol, ether and the like. r vthe inventive concept'herein disclosed and it is there- It may be noted that in all of these 4 examples, the X foreJdesired that only' such limitations be imposed upon substituent, as shown in the first structural formula, may". theappended claims as are stated therein or required by consist of a morpholino, dimethylamino, diethylamino, or the prior art. 1
a dihydroxy ethylamino substituent. The invention claimed is:
When this material is incorporated into discharge pastes 1. A whitener having the composition:
and applied to fabrics, the whites thus obtained were re- 25 X markably whiter than those obtained using ordinary dis- I N charge pastes. When this material is applied to fibers of cellulose, wool or nylon, by methods well known in the N art, the white appearance of the fabric is thereby much C=N so improved. 30 NH If small amounts of this substance are added to soap or NHOONH: 2
detergent and the resulting mixture is used to wash fabrics of cellulose, wool or nylon, the white materials thus washed are extraordinarily whiter in appearance and colored materials are brighter than similar materials 35 ethyl)-arnino.
which are washed using ordinary soaps or detergents. 2. whitener having the composition:
where X is selected from the group consisting of morpholinyl, dimethylamino, diethylamino and di-(hydroxy- 1 TH N'HC ONH: in in;
6: N-JJ CHzC 1 C-N SOrNa N=C CHZCHQ \l l o 7 N so.Na 0 cflscg oflacfia The product and process of the invention thus provide 3. A whitener having the composition:
0 O-NHB I IH NHC ONHi I IH VNH N %CNHQCH=OH- 'NHC\ /N o-N SOzNa N=C H3C-IT SoaHa H;C11I (3E3 H3 material and procedures for outstandingly increasing the 4. A whitener having the composition:
H NHC ONH, r m NH Q K 1 CNH OH=GH@NHO\ /N C-N SOSNa N=C V SOaNa N-C'HzCHa N-CHzCH;
HzCH; aC a 7 smA Wvhitenem h -cmcmon HaCHlOH SOIN aving the composition 1 NHCONH,
References Cited in the file of this patent UNITED STATES PATENTS Hein et a1. Sept. 7, 1954
Claims (1)
1. A WHITENER HAVING THE COMPOSITION:
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2840557A true US2840557A (en) | 1958-06-24 |
Family
ID=3447129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2840557D Expired - Lifetime US2840557A (en) | Oo-nhj |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2840557A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3464886A (en) * | 1966-04-29 | 1969-09-02 | American Cyanamid Co | Das-triazine brighteners and paper made therewith |
| US3951965A (en) * | 1973-09-21 | 1976-04-20 | Hoechst Aktiengesellschaft | Bis-triazinyl-amino)-stilbene-disulfonic acid derivatives |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2595030A (en) * | 1952-04-29 | - diethanolamino - | ||
| US2616855A (en) * | 1948-01-15 | 1952-11-04 | Procter & Gamble | Detergent composition |
| US2624710A (en) * | 1945-04-12 | 1953-01-06 | Lever Brothers Ltd | Composition for laundering textiles and for imparting a whitening effect thereon |
| US2635969A (en) * | 1950-03-03 | 1953-04-21 | Goldstein Joseph | Phosphorescent yarns and method for producing same |
| US2649385A (en) * | 1953-08-18 | Optically bleached fibrous material | ||
| US2688617A (en) * | 1951-07-17 | 1954-09-07 | American Cyanamid Co | Sulfonated dihalogeno diaminostilbenes |
-
0
- US US2840557D patent/US2840557A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2595030A (en) * | 1952-04-29 | - diethanolamino - | ||
| US2649385A (en) * | 1953-08-18 | Optically bleached fibrous material | ||
| US2624710A (en) * | 1945-04-12 | 1953-01-06 | Lever Brothers Ltd | Composition for laundering textiles and for imparting a whitening effect thereon |
| US2616855A (en) * | 1948-01-15 | 1952-11-04 | Procter & Gamble | Detergent composition |
| US2635969A (en) * | 1950-03-03 | 1953-04-21 | Goldstein Joseph | Phosphorescent yarns and method for producing same |
| US2688617A (en) * | 1951-07-17 | 1954-09-07 | American Cyanamid Co | Sulfonated dihalogeno diaminostilbenes |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3464886A (en) * | 1966-04-29 | 1969-09-02 | American Cyanamid Co | Das-triazine brighteners and paper made therewith |
| US3951965A (en) * | 1973-09-21 | 1976-04-20 | Hoechst Aktiengesellschaft | Bis-triazinyl-amino)-stilbene-disulfonic acid derivatives |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2468431A (en) | o-alkoxybenzoyl derivatives of 4, 4'-diaminostilbene-2, 2'-disulfonic acid | |
| US3360479A (en) | Liquid optical brightening concentrate | |
| US3694211A (en) | Organic materials containing uv-absorbers | |
| US2618636A (en) | Bis(2-morpholino-4-amino-1,3,5-triazyl-(6)-)-4,4'-diaminostilbene sulfonic and carboxylic acids | |
| US2840557A (en) | Oo-nhj | |
| US2563493A (en) | Sulfonated | |
| US2567796A (en) | Water-soluble aminostilbene derivatives and process | |
| US2702759A (en) | Method of brightening fabrics with sulfonated dibenzothiophene dioxide derivatives | |
| US2624710A (en) | Composition for laundering textiles and for imparting a whitening effect thereon | |
| US3467600A (en) | Combination optical brightener for terephthalic acid polyester fibers | |
| US2793192A (en) | Optical bleaching compositions containing tertiary amino substituted 2-aryl aryleneazoles | |
| US2521665A (en) | Stilbene disulfonic acid derivatives | |
| US2643197A (en) | Fluorescent alkoxy benzoyl derivatives of 4,4' diamino stilbene-2,2' disulfonic acidand detergent compositions containing same | |
| US2671784A (en) | Chlorine-fast fluorescent optical | |
| US2763650A (en) | Derivatives of x | |
| US2528323A (en) | Method of treating textile mate | |
| US2676982A (en) | Fluorescent agents | |
| US3127270A (en) | New stilbene compounds | |
| US2723288A (en) | Fluorescent agents | |
| US2762801A (en) | Bis-triazinylamino stilbene compounds | |
| US2911415A (en) | Optical whitener | |
| US3558611A (en) | Novel stilbene derivatives | |
| US2595030A (en) | - diethanolamino - | |
| US3546218A (en) | Substituted bis-triazinylamino stilbene compounds and compositions thereof | |
| US2643198A (en) | Fluorescent compound and methods of imparting fluorescent effects to materials |