US3690947A - Process for the optical brightening of fibrous materials made from polyacrylonitrile - Google Patents
Process for the optical brightening of fibrous materials made from polyacrylonitrile Download PDFInfo
- Publication number
- US3690947A US3690947A US4746A US3690947DA US3690947A US 3690947 A US3690947 A US 3690947A US 4746 A US4746 A US 4746A US 3690947D A US3690947D A US 3690947DA US 3690947 A US3690947 A US 3690947A
- Authority
- US
- United States
- Prior art keywords
- liquor
- polyacrylonitrile
- fibrous materials
- materials made
- weight
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
- D06L4/679—Fixing treatments in optical brightening, e.g. heating, steaming or acid shock
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
Definitions
- Fibrous materials made of polymers containing at least 85% of polyacrylonitrile can be optically brightened in a said material with a liquor containing a 1-(4'-B-alkoxyethyl sulfonyl)-phenyl-3-p-chlorophenyl-A -pyrazoline, adjusting the impregnated material to a liquor content of about 5 to 120% by weight, referred to the dry-weight of i the goods, and heating it for about 2 seconds to 30 minutes to a temperature of about 100 to 150 C,
- the present invention provides a process for the optical brightening of fibrous materials made from polyacrylonitrile.
- Example 7 of the cited patent specification also fibrous materials of polyacrylonitrile may be brightened therewith. However, it appeared that the brightening effect obtainable with the compounds of the said type under the conditions stated in that patent can still be improved.
- fibrous materials made from polyacrylonitrile or polymers containing at least 85% of polyacrylonitrile can be optically brightened in a particularly advantageous manner, when they are impreg-L nated with an optical brightener of Formula II in which A is a lower, optionally branched, alkylene radical, R is a lower alkyl group, R each represent a lower alkyl group which together with the nitrogen atom may form a saturated heterocyclic ring, X stands for a colorless anion and n is 1 or 2, and the impregnated fabric is adjusted to a liquor content of about 5 to referred to the weight of the goods, and heated, subsequently, for about two seconds to about 30 minutes to a temperature from about 100 to about 150 C. The heating is, preferably, achieved, with steam of about 100 to about C. It may also be advantageous to dry the impregnated fibrous material before heating or, preferably, steaming it. The described treatment is advantageously performed continuously.
- the brightening effect achieved in said manner can still be enhanced when a non-ionic nitrogen containing fatty acid oxethylate and/or a quaternary condensation product of a fatty acid is added to the brightening liquor.
- the additives mentioned provide, when used in conjunction with the above-identified optical brighteners, a degree of whiteness of exceptional brilliance. Moreover, they exert a brightening and softening eifect on the fibre which, for example, results in an essential improvement in the later spinning Process of spinning cables.
- the brightened fabric is to be printed simultaneously, it is advisable to subject it, after it has been padded with the optical brightener and, optionally, the said additives, to an intermediary drying at about 50 to about C.
- the thus dried fabric is, subsequently, printed and then heated in known manner, preferably by steaming.
- the heating process serves for fixing the printing ink which has been applied to the fabric.
- the optical brightener padded onto the material comes into its full effect.
- furthennore known thickeners such as starch ether, tragacanth, carob bean flour, crystal gum etc. may be added.
- Another preferred version of carrying out the instant process consists in using the brighteners corresponding to Formula II which have a blue fluorescence of a violet hue and yield thus brightenings of a violet to reddish tint, in
- the compounds of Formula III show a greenishblue fluorescence and are thus able, when applied in mixture with the compounds of Formula II, to compensate the reddish tint thereof. They are advantageously added in an amount of about 0.05 to about by weight, preferably about 0.5 to about 3% by weight, referred to compound II.
- the compounds of Formula III can be obtained by condensing di(p-chlorobenzoD-acetone with 4-hydrazinepheny1-,8-hydroxy-ethyl-sulfone, subsequent transformation of the fi-hydroxyethyl group viathe sulfuric acid ester into the vinylsulfone group and addition thereto of a correspondingly substituted alcohol.
- concentrations of optical brightener employed in the instant process are within the usual range. They can be easily determined by anyone skilled in the art by simple preliminary tests. As a guide-line the threshold values of about 0.1 to about 50 g. of optical brightener/l. of impregnation liquor may serve.
- concentration of the brightener in the impregnation liquor and the liquor content are adjusted such to yield a concentration of brightener on the goods of about 0.05-to about 5% by weight.
- EXAMPLE 1 A sliver consisting of at least 85% of polyacrylonitrile was treated with a bleaching liquor containing as the optical brightener 1 g./l. of the compound of Formula IV.
- the fabric was squeezed off to a moisture content of 80%, between rollers and dried for two minutes at C.
- the pH of the solution was adjusted to 2 by means of sulfuric acid.
- 2 g./l. of a quaternated condensation product of diethylene triamine and stearic acid were added to the padding liquor.
- the knit fabric was, after its impregnation with the said solution, squeezed off between rollers until its moisture content was about 100% and treated for 30 seconds with saturated steam of about 120 C. in an appropriate steamer.
- the thus brightened fabric showed an excellent degree of whiteness, substantially superior to that of the untreated goods.
- the impregnation liquor contains an adjuvant selected from the group consisting of a nonionic condensation product of a fatty acid and oxethylated ammonia and a quaternary condensation product of a fatty acid and a low-molecular aliphatic polyamine.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE1904424A DE1904424C3 (de) | 1969-01-30 | 1969-01-30 | Verfahren zum optischen Aufhellen von Fasermaterialien aus Polyacrylnitril |
Publications (1)
Publication Number | Publication Date |
---|---|
US3690947A true US3690947A (en) | 1972-09-12 |
Family
ID=5723727
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US4746A Expired - Lifetime US3690947A (en) | 1969-01-30 | 1970-01-21 | Process for the optical brightening of fibrous materials made from polyacrylonitrile |
Country Status (19)
Country | Link |
---|---|
US (1) | US3690947A (fr) |
JP (1) | JPS5310196B1 (fr) |
AT (1) | AT299877B (fr) |
BE (1) | BE745278A (fr) |
BG (1) | BG21419A3 (fr) |
BR (1) | BR7016461D0 (fr) |
CH (2) | CH552708A (fr) |
CS (1) | CS150901B2 (fr) |
DE (1) | DE1904424C3 (fr) |
ES (1) | ES376024A1 (fr) |
FI (1) | FI48589C (fr) |
FR (1) | FR2029718B1 (fr) |
GB (1) | GB1288545A (fr) |
IL (1) | IL33754A (fr) |
NL (1) | NL7000762A (fr) |
PL (1) | PL80451B1 (fr) |
RO (1) | RO57994A (fr) |
SE (1) | SE364319B (fr) |
YU (1) | YU34723B (fr) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4003889A (en) * | 1973-06-21 | 1977-01-18 | Sandoz Ltd. | 1,3-Diaryl-2-pyrazoline derivatives |
US4036851A (en) * | 1974-01-29 | 1977-07-19 | Sandoz Ltd. | 1,3-Diphenyl substituted pyrazolines |
US4085101A (en) * | 1973-07-18 | 1978-04-18 | Sandoz Ltd. | 1,3-Diaryl-2-pyrazoline derivatives |
US4263431A (en) * | 1978-05-29 | 1981-04-21 | Ciba-Geigy Corporation | Cationic fluorescent whitening agents |
US20050251931A1 (en) * | 2002-02-28 | 2005-11-17 | Gerhard Zirkenbach | Aqueous liquid formulations of pyrazoline brighteners |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3134942A1 (de) * | 1981-09-03 | 1983-03-17 | Bayer Ag, 5090 Leverkusen | Aufhellersalze und deren verwendung fuer das nassspinnen von acrylfasern |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1217013B (de) * | 1964-03-13 | 1966-05-18 | Hoechst Ag | Seifenzusatzmittel |
DE1469222B1 (de) * | 1964-09-25 | 1972-03-09 | Hoechst Ag | Pyrazolinderivate sowie ihre Herstellung und Verwendung |
-
1969
- 1969-01-30 DE DE1904424A patent/DE1904424C3/de not_active Expired
-
1970
- 1970-01-14 BG BG013744A patent/BG21419A3/xx unknown
- 1970-01-16 RO RO197062152A patent/RO57994A/ro unknown
- 1970-01-19 CS CS380A patent/CS150901B2/cs unknown
- 1970-01-20 NL NL7000762A patent/NL7000762A/xx unknown
- 1970-01-21 IL IL33754A patent/IL33754A/en unknown
- 1970-01-21 US US4746A patent/US3690947A/en not_active Expired - Lifetime
- 1970-01-23 FI FI700197A patent/FI48589C/fi active
- 1970-01-26 JP JP637370A patent/JPS5310196B1/ja active Pending
- 1970-01-27 CH CH114570A patent/CH552708A/xx unknown
- 1970-01-27 CH CH114570D patent/CH114570A4/xx unknown
- 1970-01-28 AT AT78970A patent/AT299877B/de not_active IP Right Cessation
- 1970-01-29 YU YU209/70A patent/YU34723B/xx unknown
- 1970-01-29 SE SE01112/70A patent/SE364319B/xx unknown
- 1970-01-29 PL PL1970138468A patent/PL80451B1/pl unknown
- 1970-01-29 ES ES376024A patent/ES376024A1/es not_active Expired
- 1970-01-29 GB GB1288545D patent/GB1288545A/en not_active Expired
- 1970-01-30 FR FR707003308A patent/FR2029718B1/fr not_active Expired
- 1970-01-30 BE BE745278D patent/BE745278A/fr unknown
- 1970-01-30 BR BR216461/70A patent/BR7016461D0/pt unknown
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4003889A (en) * | 1973-06-21 | 1977-01-18 | Sandoz Ltd. | 1,3-Diaryl-2-pyrazoline derivatives |
US4085101A (en) * | 1973-07-18 | 1978-04-18 | Sandoz Ltd. | 1,3-Diaryl-2-pyrazoline derivatives |
US4036851A (en) * | 1974-01-29 | 1977-07-19 | Sandoz Ltd. | 1,3-Diphenyl substituted pyrazolines |
US4263431A (en) * | 1978-05-29 | 1981-04-21 | Ciba-Geigy Corporation | Cationic fluorescent whitening agents |
US20050251931A1 (en) * | 2002-02-28 | 2005-11-17 | Gerhard Zirkenbach | Aqueous liquid formulations of pyrazoline brighteners |
US7300474B2 (en) | 2002-02-28 | 2007-11-27 | Clariant Produkte (Deutschland) Gmbh | Aqueous liquid formulations of pyrazoline brighteners |
Also Published As
Publication number | Publication date |
---|---|
FI48589C (fi) | 1974-11-11 |
BG21419A3 (bg) | 1976-05-20 |
YU20970A (en) | 1979-07-10 |
FI48589B (fr) | 1974-07-31 |
DE1904424B2 (de) | 1973-07-12 |
DE1904424C3 (de) | 1974-03-07 |
PL80451B1 (fr) | 1975-08-30 |
CH114570A4 (fr) | 1974-02-28 |
BR7016461D0 (pt) | 1973-01-18 |
RO57994A (fr) | 1975-06-15 |
CS150901B2 (fr) | 1973-09-17 |
GB1288545A (fr) | 1972-09-13 |
YU34723B (en) | 1979-12-31 |
FR2029718B1 (fr) | 1974-03-01 |
ES376024A1 (es) | 1972-03-16 |
SE364319B (fr) | 1974-02-18 |
BE745278A (fr) | 1970-07-30 |
NL7000762A (fr) | 1970-08-03 |
DE1904424A1 (de) | 1970-08-13 |
IL33754A0 (en) | 1970-03-22 |
AT299877B (de) | 1972-07-10 |
JPS5310196B1 (fr) | 1978-04-12 |
FR2029718A1 (fr) | 1970-10-23 |
CH552708A (fr) | 1974-08-15 |
IL33754A (en) | 1973-01-30 |
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