US3377412A - Polyvinyl pyrrolidone in viscose and method of producing dye-receptive filaments - Google Patents

Polyvinyl pyrrolidone in viscose and method of producing dye-receptive filaments Download PDF

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Publication number
US3377412A
US3377412A US660250A US66025067A US3377412A US 3377412 A US3377412 A US 3377412A US 660250 A US660250 A US 660250A US 66025067 A US66025067 A US 66025067A US 3377412 A US3377412 A US 3377412A
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United States
Prior art keywords
viscose
pvp
filaments
yarns
polyvinyl pyrrolidone
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Expired - Lifetime
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US660250A
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English (en)
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Neal E Franks
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Akzona Inc
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American Enka Corp
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Priority to US660250A priority Critical patent/US3377412A/en
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    • D—TEXTILES; PAPER
    • D02—YARNS; MECHANICAL FINISHING OF YARNS OR ROPES; WARPING OR BEAMING
    • D02G—CRIMPING OR CURLING FIBRES, FILAMENTS, THREADS, OR YARNS; YARNS OR THREADS
    • D02G3/00—Yarns or threads, e.g. fancy yarns; Processes or apparatus for the production thereof, not otherwise provided for
    • D02G3/02—Yarns or threads characterised by the material or by the materials from which they are made
    • D02G3/04—Blended or other yarns or threads containing components made from different materials
    • D02G3/045—Blended or other yarns or threads containing components made from different materials all components being made from artificial or synthetic material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/08—Cellulose derivatives
    • C08L1/22—Cellulose xanthate
    • C08L1/24—Viscose
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
    • D01F2/08—Composition of the spinning solution or the bath
    • D01F2/10—Addition to the spinning solution or spinning bath of substances which exert their effect equally well in either
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06C—FINISHING, DRESSING, TENTERING OR STRETCHING TEXTILE FABRICS
    • D06C23/00—Making patterns or designs on fabrics
    • 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
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile

Definitions

  • ABSTRACT OF THE DISCLOSURE A process for the production of regenerated cellulose in the form of textile structures such as filaments, fibers and yarns, the combination including incorporating into a viscose, prior to extrusion thereof, an amount of polyvinyl pyrrolidone having an average molecular weight of about 360,000 and a K-value between 80-100 in order to permit dyeing with acid or premetallized dyestuffs.
  • the thus modified structures can then be combined with unmodified structures that are only susceptible to those dyestuffs normally used in dyeing regenerated cellulose in order to obtain a composite textile article of manufacture consisting of polyvinyl pyrrolidone modified textile structures and unmodified structures that are especially suitable for multicolored effect dyeing when utilizing a single dyebath and containing at least two distinct classes of dyestuffs, i.e., the above-mentioned acid or premetallized dyes and direct or substantive dyes.
  • This invention relates to the production of textile structures consisting of regenerated cellulose such as yarns, filaments, fibers or the like as well as fabrics made therefrom which have remarkable dyeing properties with respect to the acid and/or premetallized dyestuffs.
  • This application is a continuation-in-part of application Ser. No. 371,840 filed June 1, 1964, commonly assigned herewith now abandoned.
  • Compounds which the prior art teaches that can be uniformly incorporated in spinnable solutions or compositions include, for example, the polyalkylene amines, polyalkylene imines, various urea derivatives, basic condensation products from phenol, formaldehyde, aliphatic monoor diamines, reaction products of halogenated aliphatic or aromatic hydrocarbons, esters, ketones, polymerizates, etc.
  • the compounds when added to spinnable compositions such as viscose or the like, increase the affinity of the structures for acid and/or premetallized dyestuffs in some degree although, with most, serious practical disadvantages exist.
  • Another object of this invention is to provide a process for increasing the afiinity of viscose fibers and yarns for dyes, more specifically the acid and premetallized type dyes.
  • Still another object of this invention is to provide a modified fiber-forming viscose solution that will increase the action of conventional viscose treating dyestuffs and easily accept acid and premetallized dyes.
  • An additional object of this invention is to provide a process for obtaining a uniform dispersion and retention of the dye-influencing additive throughout the viscose fibers and yarns.
  • regenerated cellulose fibers and filaments can be modified to possess an increased afiinity for certain dyes by incorporating into a regenerated cellulose solution, such as viscose, prior to filament or fiber formation a small amount of high molecular weight polyvinyl pyrrolidone (hereinafter referred to as PVP).
  • PVP polyvinyl pyrrolidone
  • regenerated cellulose textile structures can be produced that have a remarkable increased and lasting aflinity for those dyestuffs normally used in dyeing the nitrogen-containing natural or synthetic filaments, fibers and yarns. Furthermore, the dyestuffs, i.e., acid and premetallized dyes, do not migrate or wash out when subjected to severe wash tests and evaluations.
  • the addition of the PVP to the viscose stream increases the number of dye sites available in the extruded filament for the attachment of the premetallized or acid dye molecules and the PVP is held in the regenerated cellulose by an attraction or bonding between the PVP molecule and hydroxyl hydrogen atoms of the cellulose molecules although a positive cross-linking or chemical reaction does not appear to take place to any appreciable extent between the polymer molecules.
  • the high molecular weight PVP is a readily available material and may be incorporated into the viscose solution in a number of ways. For example, it may be mixed batch-wise or it may be added directly to the flowing stream prior to spinning by a method such as that shown by Patent No. 2,934,448 to T. E. Patton. The exact method used to effectively mix the solutions is not critical, as long as a homogeneous dispersion of the PVP in the viscose is accomplished.
  • a high degree of retention of the PVP in. the final fiber is believed accomplished due to the unusual hydrogen bonding previously mentioned which prevents subsequent loss of the dye in normal washings of the dyed fabric.
  • the addition prior to spinning also allows a more uniform distribution of the PVP throughout the entire fiber product, thus in effect creating a more uniform coloring in the textile material.
  • the amount of the high molecular weight PVP added to the fiber-forming viscose solution can be varied, depending on the results desired. Amounts less than about 2% by weight PVP based on the weight of the cellulose in the viscose solution (CIV) are not generally sufficient to produce the degree of effect desired. It is preferred that amounts below 6% be used since greater amounts have been found to cause difficulties in spinning and processing of the viscose solution prior to fiber or filament formation. Preferably, amounts of PVP ranging from 2% to are employed in the process.
  • the molecular weight of the polymeric vinyl pyrrolidone to be employed may range from about 200,000 to 400,000 or higher. Optimumly,,it is preferred that the average molecular weight be approximately 360,000 as determined by appropriate viscosity measurement techniques.
  • Spinning procedures and equipment customarily used in production of viscose fibers can be used with the PVP-modified viscose and the fiber product may be processed into yarn by any known means.
  • the attached figure shows a schematic representation of one particularly suitable procedure for forming composite yarns of the invention. Modified and unmodified filament bundles can either be combined immediately after precipitation of the viscose in spinbath or they can be combined immediately before collection in a suitable package (spool or cake).
  • Combining immediately after spinning results in a heather coloring effect in the yarns, i.e., a random blending of one color into another, caused by filament placement, while combining the yarns immediately before collecting into a package results in a distinct contrasting two-color effect when two distinct color producing dyestuffs are used, or, alternatively, a contrasting two-tone effect when a one-color producing direct dyestuff is used.
  • the modified yarn can be crosswoven with untreated viscose yarns into fabrics or tufted into carpets and, when dyed with a direct dyestuff of a single color using standard procedures, a striking two-tone wash fast color effect is achieved in the finished product. Dyeing with dyes of two distinct color, i.e., one acid or premetallized and one direct, will give a two-color effect in the fabrics or carpets.
  • the tow can be cut into fibers of preselected length according to known practices.
  • the staple fibers can be manufactured from solely PVP-containing yarns and thereafter spun with synthetic staple, e.g., nylon, polyester or acrylic, to produce yarns having distinct multicolored characteristics when woven into fabrics; or, composite regenerated cellulose fibers (PVP modified and unmodified) can also be spun with synthetic staple fibers to produce fabrics having an even further increased multicoloring capacity.
  • Example I A fiber-forming viscose solution, prepared by conventional xanthation of alkali cellulose, followed by the usual treatment with dilute sodium hydroxide, was combined with a 20% aqueous solution of PVP (a clear viscous aqueous solution of polyvinyl pyrrolidone sold by General Aniline & Film Corporation, New York, N.Y., under the name K- and having an average molecular weight of about 360,000) at 49 F. to produce a resulting batch mixture containing 2.5% PVP-CIV (cellulose in viscose). The mixture was agitated for one-half hour to disperse and dissolve the PVP throughout the viscose. The result- 5 ing mixture was deaerated overnight at 63 F.
  • PVP clear viscous aqueous solution of polyvinyl pyrrolidone sold by General Aniline & Film Corporation, New York, N.Y., under the name K- and having an average molecular weight of about 360,000
  • Example II A viscose solution prepared as in Example I was injected with a 5.0% aqueous solution of PVP. The injection was made directly into the viscose stream and mixed according to the process defined by the aforementioned Patent No. 2,934,448. The final composition spun contained 2.5% by weight PVP to the CW. The composition was spun into a spinbath containing 11.2% sulfuric acid, 5.1% magnesium sulfate, 17.45% sodium sulfate, and 1.0% zinc sulfate, and the extruded filament was then conventionally purified and dyed.
  • Example III A skein composed of the viscose prepared by the process of Example II and an untreated viscose skein were scoured with Rohm & Haas Triton CF 10, 0.2% (a benzyl ether of an acetylphenol-ethylene oxide adduct) and 0.5% tetrasodium pyrophosphate at 180 F. for 20 minutes. After rinsing, the skeins were placed in a 1.0% Triton CF 10 bath at F. for ten minutes. The temperature of the bath was raised to 200 F. and 0.5% of Du Ponts Alkanol HCS (a non-ionic surfactant) and 0.3% ammo- V. A unique two-color effect was produced in the material.
  • Rohm & Haas Triton CF 10 0.2% (a benzyl ether of an acetylphenol-ethylene oxide adduct) and 0.5% tetrasodium pyrophosphate at 180 F. for 20 minutes. After
  • Example IV Skeins of treated and untreated viscose yarns were prepared and scoured in the same manner as Example III.
  • the skeins were then added to a solution containing 0.5% Triton CF 10 and Geigy Chemicals Erional NW 2.0% (a mixed condensate of naphthalene mono-sulfonic acid with dihydroxy diphenylsulfones and formaldehyde) at 115 F. and allowed to remain for 10 minutes.
  • the treating bath was then heated to 200 F., 15% sodium chloride was added, and a premetallized dye consisting of 0.5% CI Acid Red 182 was added. After 45 minutes, the skeins were removed, rinsed and dried. A slight staining was observed on the nontreated skein while the treated skein was a deep red.
  • Example V A knitted fabric composed of treated and untreated yarns was scoured and pretreated with Triton CF 10 and Erional NW as in Example IV. To the resulting solution was added a mixture of premetallized and direct dyestuffs consisting of Ciba Chemical & Dye Companys Cibalan Brilliant Blue RL 5.0%, Organic Chemical Corporations Orcolite Fast Yellow EFL 0.3%, and General Dyestuff Companys Fastusol Blue FL 3 GL 0.6%. After 45 minutes at 200 F. the knitted fabric was removed and rinsed. The resulting treated fabric produced a two-color efiect consisting of deep blue and green. Standard light fastness and wash fastness tests showed no significant loss in the treated yarn portions compared to the untreated yarn portions of the fabric.
  • Example VI A tufted carpet material produced by combination of the regenerated cellulosic fibers treated with PVP and such nontreated fibers was dyed according to Example Examples VIIX
  • the above samples in the table clearly show that the K-90 modified yarns will not solubilize in any appreciable amounts when used according to the invention and, moreover, will have a much improved dye affinity over the standard viscose yarns when treated with lower molecular weight polymer under identical conditions.
  • the Kvalue (Fikentscher) of any particular mixture of polymers is calculated from viscosity data and is useful as an indication of the average molecular weight of such mixture. Its determination is fully described in Modern Plastics, 23, No. 3, 157-61, 212, 214, 216, 218 (1945) and is defined as 1000 times k in the empirical relative viscosity equation:
  • C is the concentration in grams per hundred cc. of polymer solution and a is the ratio of the viscosity coefficient in order to avoid the use of decimals.
  • polymeric N-vinyl pyrrolidone having a K-value of 200, preferably of 80 to 100, and having an average molecular weight of about 360,000.
  • a fiber-forming composition of matter comprising a major amount of viscose including a wash-fast and lightfast dye improving quantity of at least about 2% by weight of polyvinyl pyrrolidone based on the weight of cellulose in said viscose, said polyvinyl pyrrolidone being of average molecular weight of about 360,000 and having a K-value of approximately 8090.
  • a process for the preparation of multifilament yarns of regenerated cellulose having a wash-fast and light-fast afiinity for acid and/ or premetallized dyestuffs comprising in combination:

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Mechanical Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Artificial Filaments (AREA)
  • Coloring (AREA)
US660250A 1964-06-01 1967-08-14 Polyvinyl pyrrolidone in viscose and method of producing dye-receptive filaments Expired - Lifetime US3377412A (en)

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US37184064A 1964-06-01 1964-06-01
US660250A US3377412A (en) 1964-06-01 1967-08-14 Polyvinyl pyrrolidone in viscose and method of producing dye-receptive filaments

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AT (1) AT256327B (enrdf_load_stackoverflow)
BE (1) BE664214A (enrdf_load_stackoverflow)
CH (1) CH452104A (enrdf_load_stackoverflow)
DE (1) DE1494547A1 (enrdf_load_stackoverflow)
ES (1) ES313581A1 (enrdf_load_stackoverflow)
FR (1) FR1444316A (enrdf_load_stackoverflow)
GB (1) GB1064905A (enrdf_load_stackoverflow)
NL (1) NL6506343A (enrdf_load_stackoverflow)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3919385A (en) * 1972-11-24 1975-11-11 Fmc Corp Process for producing high fluid-holding fiber mass
US3951889A (en) * 1972-11-24 1976-04-20 Fmc Corporation Fluid absorbent alloy fibers
US4041121A (en) * 1972-11-24 1977-08-09 Avtex Fibers Inc. Method for making high fluid-holding fiber mass
US4113674A (en) * 1976-12-27 1978-09-12 The Dow Chemical Company Poly-2-alkyl-2-oxazoline modified regenerated cellulosics
US4136697A (en) * 1972-11-24 1979-01-30 Avtex Fibers Inc. Fibers of high fluid-holding capacity
US4159362A (en) * 1977-12-30 1979-06-26 Owens-Corning Fiberglas Corporation Aqueous size composition for glass fibers containing epoxy resin, polyethylene glycol monostearate polyvinylpyrrolidone, methacryloxypropyltrialkoxysilane and a glucan-carboxymethyl cellulose mixture
US4699625A (en) * 1984-04-11 1987-10-13 Collins & Aikman Corporation Method of continuously dyeing fabrics containing blends of synthetic fibers and cellulosic fibers with premetallized dye and polyvinyl pyrrolison/styrene copolymer
US5684141A (en) * 1994-01-29 1997-11-04 Hoechst Aktiengesellschaft Aminated cellulosic synthetic fibers
US20080299305A1 (en) * 2004-04-07 2008-12-04 Urea Casale S.A. Fluid Bed Granulation Process
US20080307587A1 (en) * 2005-06-07 2008-12-18 Shah Ketan N Carpet decor and setting solution compositions
US20090019647A1 (en) * 2005-06-07 2009-01-22 Frazee Glenn R Composition for application to a surface
US20090271933A1 (en) * 2005-06-07 2009-11-05 S.C. Johnson & Son, Inc. Composition For Application To A Surface
US20100154146A1 (en) * 2008-07-02 2010-06-24 S.C. Johnson & Son, Inc. Carpet decor and setting solution compositions
US20110097506A1 (en) * 2005-06-07 2011-04-28 Shah Ketan N Devices for applying a colorant to a surface
US8061269B2 (en) 2008-05-14 2011-11-22 S.C. Johnson & Son, Inc. Multilayer stencils for applying a design to a surface
US8846154B2 (en) 2005-06-07 2014-09-30 S.C. Johnson & Son, Inc. Carpet décor and setting solution compositions
CN105420925A (zh) * 2015-10-30 2016-03-23 无锡市长安曙光手套厂 以静电喷浆制备具有防霉、抗菌及除臭功能纤维素不织布的方法
EP3690098A1 (en) * 2019-01-30 2020-08-05 Tessitura Clara S.r.l. Denim fabric and method for making said fabric
US20220033529A1 (en) * 2017-03-15 2022-02-03 Treetotextile Ab Regenerated cellulosic fibres spun from an aqueous alkaline spindope

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE398360B (sv) * 1975-10-28 1977-12-19 Avtex Fibers Inc Rayonfiber bestaende av en grundmassa av cellulosa med deri dispergerad polyvinylpyrrolidon
DE19520804C3 (de) * 1995-02-21 2000-08-24 Cellcat Gmbh Cellulosepartikel, die im Innern kationische Gruppen aufweisen, Verfahren zu ihrer Herstellung und ihre Verwendung

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1629769A (en) * 1926-07-20 1927-05-24 Thayer P Gates Cross-dyeing cellulose fabric
US2336341A (en) * 1940-12-28 1943-12-07 Rohm & Haas Changing the capacity of cellulosic fibers for dyes
US2882253A (en) * 1955-11-16 1959-04-14 Dow Chemical Co Method for stabilizing polyvinylpyrrolidone and compositions thereby obtained
US2897182A (en) * 1957-09-06 1959-07-28 Rohm & Haas Oxazine and oxazoline polymers
US2901457A (en) * 1954-11-15 1959-08-25 Gen Aniline & Film Corp Process of reacting a polymeric n-vinyl lactam with a polymeric carboxylic acid and product obtained thereby
US2975019A (en) * 1954-11-03 1961-03-14 American Viscose Corp Producing all skin viscose rayon
US2989360A (en) * 1957-05-31 1961-06-20 Gen Aniline & Film Corp Continuous dyeing process
US3255275A (en) * 1961-01-30 1966-06-07 Dow Chemical Co Process for enhancing the dye-receptivity of continuous, coherent articles and products therefrom

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1629769A (en) * 1926-07-20 1927-05-24 Thayer P Gates Cross-dyeing cellulose fabric
US2336341A (en) * 1940-12-28 1943-12-07 Rohm & Haas Changing the capacity of cellulosic fibers for dyes
US2975019A (en) * 1954-11-03 1961-03-14 American Viscose Corp Producing all skin viscose rayon
US2901457A (en) * 1954-11-15 1959-08-25 Gen Aniline & Film Corp Process of reacting a polymeric n-vinyl lactam with a polymeric carboxylic acid and product obtained thereby
US2882253A (en) * 1955-11-16 1959-04-14 Dow Chemical Co Method for stabilizing polyvinylpyrrolidone and compositions thereby obtained
US2989360A (en) * 1957-05-31 1961-06-20 Gen Aniline & Film Corp Continuous dyeing process
US2897182A (en) * 1957-09-06 1959-07-28 Rohm & Haas Oxazine and oxazoline polymers
US3255275A (en) * 1961-01-30 1966-06-07 Dow Chemical Co Process for enhancing the dye-receptivity of continuous, coherent articles and products therefrom

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3919385A (en) * 1972-11-24 1975-11-11 Fmc Corp Process for producing high fluid-holding fiber mass
US3951889A (en) * 1972-11-24 1976-04-20 Fmc Corporation Fluid absorbent alloy fibers
US4041121A (en) * 1972-11-24 1977-08-09 Avtex Fibers Inc. Method for making high fluid-holding fiber mass
US4136697A (en) * 1972-11-24 1979-01-30 Avtex Fibers Inc. Fibers of high fluid-holding capacity
US4113674A (en) * 1976-12-27 1978-09-12 The Dow Chemical Company Poly-2-alkyl-2-oxazoline modified regenerated cellulosics
US4159362A (en) * 1977-12-30 1979-06-26 Owens-Corning Fiberglas Corporation Aqueous size composition for glass fibers containing epoxy resin, polyethylene glycol monostearate polyvinylpyrrolidone, methacryloxypropyltrialkoxysilane and a glucan-carboxymethyl cellulose mixture
US4699625A (en) * 1984-04-11 1987-10-13 Collins & Aikman Corporation Method of continuously dyeing fabrics containing blends of synthetic fibers and cellulosic fibers with premetallized dye and polyvinyl pyrrolison/styrene copolymer
US5684141A (en) * 1994-01-29 1997-11-04 Hoechst Aktiengesellschaft Aminated cellulosic synthetic fibers
US5865858A (en) * 1994-01-29 1999-02-02 Hoechst Aktiengesellschaft Aminated cellulosic synthetic fibers
US20080299305A1 (en) * 2004-04-07 2008-12-04 Urea Casale S.A. Fluid Bed Granulation Process
US20090271933A1 (en) * 2005-06-07 2009-11-05 S.C. Johnson & Son, Inc. Composition For Application To A Surface
US8846154B2 (en) 2005-06-07 2014-09-30 S.C. Johnson & Son, Inc. Carpet décor and setting solution compositions
US20080307587A1 (en) * 2005-06-07 2008-12-18 Shah Ketan N Carpet decor and setting solution compositions
US7727289B2 (en) 2005-06-07 2010-06-01 S.C. Johnson & Son, Inc. Composition for application to a surface
US20090019647A1 (en) * 2005-06-07 2009-01-22 Frazee Glenn R Composition for application to a surface
US7776108B2 (en) 2005-06-07 2010-08-17 S.C. Johnson & Son, Inc. Composition for application to a surface
US7780744B2 (en) 2005-06-07 2010-08-24 S.C. Johnson & Son, Inc. Carpet decor and setting solution compositions
US20100256263A1 (en) * 2005-06-07 2010-10-07 S.C. Johnson & Son, Inc. Composition for application to a surface
US20110097506A1 (en) * 2005-06-07 2011-04-28 Shah Ketan N Devices for applying a colorant to a surface
US8734533B2 (en) 2005-06-07 2014-05-27 S.C. Johnson & Son, Inc. Composition for application to a surface
US8557758B2 (en) 2005-06-07 2013-10-15 S.C. Johnson & Son, Inc. Devices for applying a colorant to a surface
US8499689B2 (en) 2008-05-14 2013-08-06 S. C. Johnson & Son, Inc. Kit including multilayer stencil for applying a design to a surface
US8061269B2 (en) 2008-05-14 2011-11-22 S.C. Johnson & Son, Inc. Multilayer stencils for applying a design to a surface
US20100154146A1 (en) * 2008-07-02 2010-06-24 S.C. Johnson & Son, Inc. Carpet decor and setting solution compositions
CN105420925A (zh) * 2015-10-30 2016-03-23 无锡市长安曙光手套厂 以静电喷浆制备具有防霉、抗菌及除臭功能纤维素不织布的方法
US20220033529A1 (en) * 2017-03-15 2022-02-03 Treetotextile Ab Regenerated cellulosic fibres spun from an aqueous alkaline spindope
EP3690098A1 (en) * 2019-01-30 2020-08-05 Tessitura Clara S.r.l. Denim fabric and method for making said fabric

Also Published As

Publication number Publication date
CH452104A (de) 1968-05-31
AT256327B (de) 1967-08-10
NL6506343A (enrdf_load_stackoverflow) 1965-12-02
ES313581A1 (es) 1965-10-01
GB1064905A (en) 1967-04-12
BE664214A (enrdf_load_stackoverflow) 1965-09-16
DE1494547A1 (de) 1969-04-24
FR1444316A (fr) 1966-07-01

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