US3131079A - Brightening of fiber material by coating with 1, 3-diaryl- and 1, 3, 5-triaryl pyrazoline derivatives - Google Patents

Description

8-197 SR a ouiiwn nuum FIP83U XR 5&131079 M 3331 mg s Umted states ratent ice C. for 2030 minutes and the fabric is treated at boiling 3131079 temperature for 30 minutes, then rinsed and dried. The

BRIGEITENWG 9F FE3ER MATERIAL BY CQATIPIG a b f .th VETH AND 1 ,5 Y fabric thus treated Shows a strong I'lgH-tfiilll'hg 61 601'. W1 @HNE DERIVATIVEg t a neutral white shade and good tfastness to light.

Annemarie Wagner and Siegfried Petersen, both of The bl'ightener Used above is p p y quatemizing Leverkusen, Germany, assignors to Farbenfabrilren the 1-p-dimethyl-aminopropyl-amido-sulfonyl phenyl-3- Bayer Aktiengesellschait, Leverkusen, Germany, a p-chlorophenyl-py-razoline (described in copending U15. corpomfiml of Germany patent application Ser. No. 642,356, now abandoned, filed p i Filled Y 1961 123625 February 26, 1957, and assigned to the same assignee and Chums pnomy aliphcanou Germany 1960 in the continuation thereof, co-pending application Serial 6 Clmms' 11733'5) No. 194,999, filed May 15, 1962) with dimethyl sulfate The present invention relates to brightening agents of in a hl r nl n S lution at 80-95" C. The product the diand tri-arylpyrazoline series; more particularly it has a melting point of about 200 C. concerns dior triaryil pyrazoline compounds containing Example 2 a quaternary ammonium group. 15

Especially suitable brightening agents are 1,3-diphenyland 1,3,5-triphenylpyrazoline compounds which contain a quaternary ammonium group bound to the phenyl radical in the l-position or in the 5-position directly or via a bridge member, such as an alkylene group, an -O-al kylene mu 3 a lane or a for 20 minutes. It is then rinsed and dried. The maalkyline group phgnyl i of the 1,3 di2pheny1 terial thus treated shows a strong neutral White effect. or 1,3,5-triphenylpyrazoline compounds may carry fur- Example 3 tal'liltzrlsu-bstituentsl,1 flor example alkyl groups, substituted Into 150 Ice of a bath containing 0005 g of (hp-triy groups a ogen l methyl ammonium 1 r0 1 amido sulfonyl henylt i q' of the PIQPOSed c0n 1pOunds possible 3 p chlorophenyl-pyii az ol ine)-methyl sulfate, th ere are r o brighten 111 an outstanding manner fibre materials of the introdu ed 5 0 of acetat fibr The bath 1o '1 most varied type such as those of wool, cellulose acetate, 116mm h i i j g 2 :23 Polyamldes l polymerisates' The applica minutes then rinsed and dried The acetate fibres show tail'on of the brightening agents is performed in conventiona strong bluish fluorescence manner. The following examples serve to illustrate the invenffiijiig: 222 g g; 22 2: ff;- tion without, however, limiting the scope, thereof. fouzwing compognay e 1 6 0 e 5 g. of a p'olyamide fabric are introduced into 200 cc. of a bath containing 0.01 g. of (l-p-trimethyl-ammoniumpropyl amido sulphonyl phenyl 3 p chlorophenylpyrazoline)-methyl sulfate. The bath is slowly heated to 95-98" C. and the fabric is treated at this temperature Example 1 orn 0.005 g. of (l-p trimethyl ammonium propylarnido sulfonylphenyl 3 p chlorophenyl-pyrazoline)-methy1 0 N sulfate of the formula H.('; H.

CHgCHg C11 CHZCH C2115 are dissolved in 2.0 cc. of hot water and diluted with 180 cc. of cold water. 5 g. of a polyacrylonitrile fabric are Q-fi 3)3 SOACHT CHr-CH;

introduced into this bath. The bath is heated to 98 phenyl substituted by lower alkyl; and Z is an anion group;

Q wherein p, q and m are whole numbers within the range f 1 the sum of 1 lus bein 1-2- and n i a whole N CH so on- O P P q g s 3); 4 3 number within the range of 0-3.

2. A process according to claim 1 wherein the fluorescent compound corresponds to the formula We claim: 3. A process according to claim 1 wherein the fluores- 1. A process for improving fibers which comprises cent compound corresponds to the formula applying thereto an aqueous solution of a fluorescent compound of the general formula. N(CH3)3 Ar %N\ Q l i N Xl (W)p Z9 H2C OH3 H o-0H 2 X 4. A process according to claim 1 wherein the fluorescent compound corresponds to the formula wherein X stands for a phenyl; X stands for a member 5. A process according to claim 1 wherein the fluoresselected from the group consisting of phenyl and hydrocent compound corresponds to the formula gen; W is a substituent of the phenyl ring having the 6. A process according to claim 1 wherein the fluoresformula cent compound corresponds to the formula R1 in which Y is a member selected from the group consist- H26 ing of oxygen, sulfonyl, and sulfonylamido; R and R References Cited in the file of this patent are lower alkyl groups; R is a member selected from the group consisting of lower alkyl, lower alkoxy alkyl, UNITED STATES PATENTS and henzyl; Ar is a member selected from the group con- 2,567,796 Ackerman Sept. 11, 1951 sisting of phenyl, phenyl substituted by halogen and 2,639,990 Kendall May 26, 1953

Claims (1)

1. A PROCESS FOR IMPROVING FIBERS WHICH COMPRISES APPLYING THERETO AN AQUEOUS SOLUTION OF A FLUORESCENT COMPOUND OF THE GENERAL FORMULA