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 PDF

Info

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
Application number
US4746A
Other languages
English (en)
Inventor
Gunter Rosch
Werner Linke
Otto Smerz
Erich Schinzel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
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.)
Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Application granted granted Critical
Publication of US3690947A publication Critical patent/US3690947A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06Heterocyclic 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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60Optical bleaching or brightening
    • D06L4/679Fixing treatments in optical brightening, e.g. heating, steaming or acid shock
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/35Heterocyclic 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)
US4746A 1969-01-30 1970-01-21 Process for the optical brightening of fibrous materials made from polyacrylonitrile Expired - Lifetime US3690947A (en)

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 (ja)
JP (1) JPS5310196B1 (ja)
AT (1) AT299877B (ja)
BE (1) BE745278A (ja)
BG (1) BG21419A3 (ja)
BR (1) BR7016461D0 (ja)
CH (2) CH114570A4 (ja)
CS (1) CS150901B2 (ja)
DE (1) DE1904424C3 (ja)
ES (1) ES376024A1 (ja)
FI (1) FI48589C (ja)
FR (1) FR2029718B1 (ja)
GB (1) GB1288545A (ja)
IL (1) IL33754A (ja)
NL (1) NL7000762A (ja)
PL (1) PL80451B1 (ja)
RO (1) RO57994A (ja)
SE (1) SE364319B (ja)
YU (1) YU34723B (ja)

Cited By (5)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (6)

* Cited by examiner, † Cited by third party
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
BE745278A (fr) 1970-07-30
CH552708A (ja) 1974-08-15
FR2029718A1 (ja) 1970-10-23
FI48589C (fi) 1974-11-11
RO57994A (ja) 1975-06-15
CS150901B2 (ja) 1973-09-17
FR2029718B1 (ja) 1974-03-01
IL33754A0 (en) 1970-03-22
NL7000762A (ja) 1970-08-03
BG21419A3 (bg) 1976-05-20
ES376024A1 (es) 1972-03-16
GB1288545A (ja) 1972-09-13
DE1904424B2 (de) 1973-07-12
YU20970A (en) 1979-07-10
YU34723B (en) 1979-12-31
BR7016461D0 (pt) 1973-01-18
IL33754A (en) 1973-01-30
SE364319B (ja) 1974-02-18
CH114570A4 (ja) 1974-02-28
JPS5310196B1 (ja) 1978-04-12
PL80451B1 (ja) 1975-08-30
DE1904424C3 (de) 1974-03-07
DE1904424A1 (de) 1970-08-13
AT299877B (de) 1972-07-10
FI48589B (ja) 1974-07-31

Similar Documents

Publication Publication Date Title
EP0310083A1 (de) Verfahren zum Löschen oder Unterdrücken der Fluoreszenz von optisch aufgehellten Substraten
US3690947A (en) Process for the optical brightening of fibrous materials made from polyacrylonitrile
US2370031A (en) Process for improving fibrous material and the material treated by such process
US4499282A (en) Quaternary ammonium compounds
US3951965A (en) Bis-triazinyl-amino)-stilbene-disulfonic acid derivatives
US2956898A (en) Certification of correction
US3049446A (en) Process for the manufacture of urea, glyoxal and formaldehye reaction product useful for improving cellulosic textile materials
US4072464A (en) Epoxypropyl ammonium salt and boric acid assisted dyeing process
US5133779A (en) Cationic reaction products of basic carbamides and epihalohydrins: quaternary ammonium salts as dyeing aids for cellulose
US3382086A (en) Finishing textile fabric
US5372610A (en) Process for the after-bleaching of dyed raw cellulose using cationic compounds
US4592758A (en) After-treatment of dyed textile materials of natural polyamides or nylons with quaternized piperazine condensate
US3853583A (en) Fluorescent whitening compositions
EP0438380B1 (de) Polymerisierte quaternäre Diallylammoniumverbindungen
JPS6334189B2 (ja)
US3766083A (en) Fluorescent whitening compositions
US4468228A (en) Quaternary ammonium compounds and method for preparation thereof
US3619234A (en) Process for the optical brightening of fibrous materials of synthetic polyamides or cellulose esters
DE1469269A1 (de) Ausruestungsmittel fuer Textilgut
US2528323A (en) Method of treating textile mate
US4579560A (en) Method for dyeing of fibers in the presence of quaternary alkoxyalkylammonium retarding or leveling agent
US5322525A (en) Process for treating polyamide containing articles to enhance their moulding stability
JPS60155784A (ja) 改良された堅牢性を有する染色のためののりつけ染色法
US4705865A (en) Cationic reaction products formed from 1-aminoalkyl-imidazole compounds and epihalohydrins
US4008172A (en) Agent for brightening and removing greyness from textiles