EP0314944B1 - Zusammensetzung zum Ausrüsten und Verfahren zum Behandeln von Fasermaterialien - Google Patents

Zusammensetzung zum Ausrüsten und Verfahren zum Behandeln von Fasermaterialien Download PDF

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Publication number
EP0314944B1
EP0314944B1 EP88116823A EP88116823A EP0314944B1 EP 0314944 B1 EP0314944 B1 EP 0314944B1 EP 88116823 A EP88116823 A EP 88116823A EP 88116823 A EP88116823 A EP 88116823A EP 0314944 B1 EP0314944 B1 EP 0314944B1
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EP
European Patent Office
Prior art keywords
weight
process according
component
dispersion
treatment composition
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
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EP88116823A
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German (de)
English (en)
French (fr)
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EP0314944A3 (de
EP0314944A2 (de
Inventor
Hans-Burkhardt Vogel
Franz Mosch
Erich Rössler
Michael Dr. Bernheim
Johan Emiel De Witte
Rudolf Jozef Dams
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3M Co
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Minnesota Mining and Manufacturing Co
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Filing date
Publication date
Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Priority to AT88116823T priority Critical patent/ATE95584T1/de
Publication of EP0314944A2 publication Critical patent/EP0314944A2/de
Publication of EP0314944A3 publication Critical patent/EP0314944A3/de
Application granted granted Critical
Publication of EP0314944B1 publication Critical patent/EP0314944B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • D06M15/576—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them containing fluorine
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/227—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain

Definitions

  • the present invention describes aqueous finishing agents for the soft hydrophobic / oleophobic treatment of fiber materials based on perfluoroaliphatic compositions and extenders.
  • a method for soft hydrophobic / oleophobic treatment is also claimed.
  • Finishing agents have now been found which can be used for the simultaneous particularly smooth and soft hydrophobic / oleophobic treatment of fiber materials. These finishing agents contain perfluoroaliphatic group-containing hydrophobic / oleophobic agents, selected polyethylene emulsions and fluorine-free soft handle extender emulsions in selected proportions.
  • finishing agents of this invention namely the perfluoroaliphatic group-containing agent, the polyethylene emulsion and the fluorine-free polysiloxane softener extender are either available as a finished formulation or are added individually to the finishing bath. In this way, finishing agents are created which, surprisingly, are distinguished by overall very good effects, which also have excellent washing and dry cleaning resistance.
  • the present invention therefore describes in claims 1 to 10 aqueous finishing agents for the soft hydrophobic / oleophobic treatment of fiber materials. A method for the soft hydrophobic / oleophobic treatment of the fiber materials is then claimed in claims 11 to 13.
  • Ingredient A) is a hydrophobic / oleophobic agent containing perfluoroaliphatic groups, many of which are commercially available and which in the finished formulation have at least 5% by weight, in particular 5.5 to 15% by weight, very particularly preferably 7 to Contain 12% by weight fluorine.
  • the perfluoroaliphatic group R f can be straight-chain, branched-chain or, if the length is appropriate, also cyclic be. Combinations of these are of course also conceivable for R f .
  • the basic structure of the perfluoroaliphatic radical can contain oxygen and / or trivalent nitrogen heteroatoms in the chain, bound only to carbon atoms.
  • fluoroaliphatic agents are well known to those skilled in the art and he will have no difficulty in using the useful products.
  • the reaction of perfluoroaliphatic thioglycols with diisocyanates results in polyurethanes containing perfluoroaliphatic groups.
  • These products are typically used in aqueous dispersion for fiber treatment.
  • Such reaction products are described, for example, in US Pat. No. 4,054,592.
  • N-methylol condensation products containing perfluoroaliphatic groups are N-methylol condensation products containing perfluoroaliphatic groups. These compounds also belong to the prior art and are described in US Pat. No. 4,477,498, where the emulsification of such products is also discussed in detail.
  • the polycarbodiimides containing perfluoroaliphatic groups (R f groups) are prepared, for example, by reacting perfluoroaliphatic sulfonamide alkanols with polyisocyanates in the presence of suitable catalysts.
  • This class of compounds can also be used alone, but mostly it is used with other compounds containing R f groups, especially together with the (co) polymers. And this addresses another group of compounds that can be used in dispersion as component A).
  • fluoroaliphatic radical-containing polymers can be used, with condensation polymers such as polyesters and polyamides containing corresponding perfluoroaliphatic groups, and especially (co) polymers based on, for example, R f acrylates and R f methacrylates, different fluorine-free vinyl compounds being used as comonomers.
  • condensation polymers such as polyesters and polyamides containing corresponding perfluoroaliphatic groups
  • polymers based on, for example, R f acrylates and R f methacrylates different fluorine-free vinyl compounds
  • fluorochemical compounds can also be used as constituent A), for example guanidines containing R f groups (US Pat. No. 4,540,479), allophanates containing R f groups (US Pat. No. 4,606,737) and Biurete containing R f groups (US-A 4,668,406). These classes of component A) are mostly used in combination.
  • the active compounds of component A) generally have one or more perfluoroaliphatic radicals with preferably at least 4, in particular 6 to 14, carbon atoms.
  • Component A) is used in the finishing agents according to the invention in amounts of 25 to 65% by weight, based on the finishing agent. Since the components A) preferably contain about 7 to 12% by weight of fluorine, agents which have 30 to 55% by weight of these components are particularly suitable.
  • the emulsifiable polyethylene (polyethylene wax) contained in component B) is known and is described in detail in the prior art (DE-A-2 359 966, DE-A 2 824 716 and DE-A 1 925 993).
  • the emulsifiable polyethylene is one with functional groups, in particular COOH groups, which can be partially esterified. These functional groups are introduced by oxidation of the polyethylene.
  • functional groups in particular COOH groups, which can be partially esterified. These functional groups are introduced by oxidation of the polyethylene.
  • the emulsifiable polyethylenes contained in component B) have a density of at least 0.92 g / cm3 and an acid number at 20 ° C from at least 5 to.
  • the finishing agents according to the invention are particularly preferred of those emulsifiable polyethylenes which have a density at 20 ° C. of 0.95 to 1.05 g / cm 3, an acid number of 10 to 60 and a saponification number of 15 to 80.
  • This material is generally commercially available in the form of scales, lozenges and the like.
  • Component B that is to say the dispersion of the emulsifiable polyethylene, is used in the finishing agents in amounts of 10 to 35% by weight, based on the finishing agent and based on a 20 to 35% dispersion (based on polyethylene wax). It has been shown that higher amounts of component B) make the soft handle even more pleasant, flowing, even softer, so that amounts of 20 to 35% by weight of component B), based on the overall finishing agent, are particularly good are preferred.
  • the polyethylene wax is used in the form of emulsions. Different emulsifiers are required for this. These emulsifiers can support the soft hand effect of the finishing agents.
  • Modified hydrogen alkyl polysiloxanes in the form of aqueous dispersions are suitable as component C).
  • component C Modified hydrogen alkyl polysiloxanes in the form of aqueous dispersions.
  • compounds which are obtained by modification of hydrogen methyl polysiloxane with a long-chain alkyl radical are suitable as fluorine-free soft-grip extenders.
  • This alkyl radical should contain an average of at least 8 carbon atoms, in particular 8 to 18 carbon atoms. This condition does not preclude the presence of low-chain alkyl radicals, but it should be noted that the average carbon chain length is at least 8 carbon atoms. Compounds of this type are described in the aforementioned US-A-4,004,059.
  • those components C) which are modified to an even greater extent are particularly preferred, ie which, in addition to the above-mentioned groups, also include epoxyalkyl groups and possibly additionally aryl, in particular phenyl, groups contained in the molecule (US-A-4,625,010).
  • Such compounds then have an Si-H content of approximately 0.02 to 6, in particular 0.3 to 1.8% by weight, an epoxy number of approximately 0.01 to 0.06 and, moreover, hydrogen per g-atom of the siloxane, at least 0.2 g atom of the same is substituted by an alkyl radical (see above).
  • the constituents C) are present as an average of 25 to 40% dispersions and based on these dispersions 25 to 40% by weight, in particular 25 to 35% by weight, based on the finishing agent, of the component C) are used.
  • components C are prepared in a known manner (see the literature mentioned).
  • emulsifiers there are basically no restrictions with regard to dispersion or dispersion polymerization, i.e. Both nonionic and conventional cationic and anionic emulsifiers can be used.
  • the finished dispersions that is to say the constituents A), B) and C
  • the finishing agent according to the invention and, in addition, are frequently used in combination with other constituents
  • the emulsifiers that can be used individually are well known and do not require any special explanation.
  • the emulsifiers are used in customary amounts. In general, the amount of emulsifier is 3 to 50, preferably 8 to 40,% by weight, based on the respective solid.
  • finishing agents can be produced in a simple manner by combining components A) to C) in the stated amounts. These agents have the advantage of being a stable one-component finishing agent.
  • the fibers thus produced are used directly from fiber materials.
  • the amounts used depend on the desired effects and are usually 40 to 100, in particular 50 to 80 g / l, based on a 25 to 35% by weight finishing agent.
  • the use of the agents according to the invention is preferred due to the presence of a one-component finishing agent.
  • the equipment itself is carried out according to known methods.
  • fiber materials of all kinds can be finished as well as according to the known methods.
  • textiles are to be mentioned as fiber materials, these textiles in turn being particularly suitable, which consist of cellulose fibers or at least partially contain cellulose fibers.
  • synthetic fibers such as polyester, polyamide or polyacrylonitrile fibers and wool can also be considered as additional fibers.
  • the oil and water repellent finishing of cotton / polyester blended fabrics is particularly critical and it is precisely here that the finishing agents according to the invention show their superiority over the prior art.
  • Equipment I The following components are mixed together to produce an equipment (equipment I):
  • a commercially available dispersion emulsifier: polyethoxylated quaternary ammonium salt
  • emulsifier polyethoxylated quaternary ammonium salt
  • polymer X see DE-A 2 310 801
  • R f polycarbodiimide emulsion see example 1, DE-A 2 310 801 in a weight ratio of 2: 1.
  • polyetylene wax dispersion 50% nonylphenol ethoxylated with an average of 15 moles of ethylene oxide, based on polyethylene wax, as an emulsifier; polyethylene wax with a density at 20 ° C. of about 1, an acid number of about 13 and a saponification number of about 22).
  • an aqueous finishing liquor is prepared as follows: 60 g / l finishing agent I, 40 g / l of an approx. 60% aminoplast resin solution (contains dimethylol dihydroxyethylene urea etherified with methanol and pentamethylolmelamine in a ratio of 12: 1 and approx. 5% neutral salt), 6 g / l of a 30% zinc nitrate solution (pH approx. 1.0) and 2 g / l 60% acetic acid.
  • components A 1) to C 1) of the fleet are added separately but in equal amounts.
  • component C 1 Like fleet II, but instead of component C 1) the same amount of ⁇ , ⁇ -dihydroxy-polydimethylsiloxane (viscosity (20 ° C.) approx. 5000 mPa.s) is used in aqueous dispersion.
  • a polyester / cotton jacket Popeline 67/33 (approx. 210 g / m2) was padded with liquors I to V (liquor absorption approx. 65%), then dried at 110 ° C. for 10 minutes and condensed at 150 ° C. for 5 minutes.
  • the results of the equipment are summarized in the table below, the laundry being the usual 40 ° C. household machine wash and the chemical cleaning (CR) washing in the presence of 2 g / l of a conventional cleaning booster and 2 g / l of water (Fleet ratio 1:10).
  • the measurements were carried out after 5 days of exposure in a normal climate.
  • aqueous liquors are prepared with the finishing agents II and II a: 90 or 100 g / l of finishing agent II or IIa, 30 g / l of a 60% aqueous solution of pentamethylolmelamine trimethyl ether, 6 g / l of the catalyst solution mentioned in Example 1 and 2 g / l of 60% acetic acid ( Fleets I and II).
  • Example 1 The textile material described in Example 1 is finished with the two liquors produced and the following effects are obtained, a comparison based on the prior art (Fleet III with 80 g / l of an agent from A 2) and C2), ie without polyethylene dispersion) was also added.
  • a cotton fabric (170 g / m2) is soaked in an aqueous liquor which contains the following constituents, squeezed to a liquor absorption of about 70%, dried briefly at 105 ° C. and condensed for 5 minutes at 155 ° C.
  • Example 1 The fabric described in Example 1 is immersed in a liquor of the following composition, squeezed to a liquor absorption of 55%, dried and condensed at 160 ° C. for 3 minutes:
  • the washing and cleaning resistance is given in the same way as in the other examples.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP88116823A 1987-11-06 1988-10-11 Zusammensetzung zum Ausrüsten und Verfahren zum Behandeln von Fasermaterialien Expired - Lifetime EP0314944B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT88116823T ATE95584T1 (de) 1987-11-06 1988-10-11 Zusammensetzung zum ausruesten und verfahren zum behandeln von fasermaterialien.

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE3737753 1987-11-06
DE19873737753 DE3737753A1 (de) 1987-11-06 1987-11-06 Waessriges ausruestungsmittel und verfahren zur weichen hydrophob/oleophob-behandlung von fasermaterialien
SG105394A SG105394G (en) 1987-11-06 1994-07-30 Finishing composition and process for the treatment of fiber materials

Publications (3)

Publication Number Publication Date
EP0314944A2 EP0314944A2 (de) 1989-05-10
EP0314944A3 EP0314944A3 (de) 1991-10-09
EP0314944B1 true EP0314944B1 (de) 1993-10-06

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP88116823A Expired - Lifetime EP0314944B1 (de) 1987-11-06 1988-10-11 Zusammensetzung zum Ausrüsten und Verfahren zum Behandeln von Fasermaterialien

Country Status (11)

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US (1) US5047065A (ja)
EP (1) EP0314944B1 (ja)
JP (1) JPH01156581A (ja)
KR (1) KR950012691B1 (ja)
CN (1) CN1036419A (ja)
AU (1) AU616214B2 (ja)
DE (2) DE3737753A1 (ja)
ES (1) ES2047011T3 (ja)
HK (1) HK495A (ja)
SG (1) SG105394G (ja)
ZA (1) ZA888291B (ja)

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US8231802B2 (en) 2003-06-03 2012-07-31 Rudolf Gmbh Preparations for making planar structures oil-repellent and water-repellent, and use thereof

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EP2302130A1 (de) 2009-09-26 2011-03-30 Huntsman Textile Effects (Germany) GmbH Zusammensetzung für die Öl- und/oder Wasserabweisende Ausrüstung von Fasermaterialien
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CN103342814B (zh) * 2013-07-19 2015-07-29 湖南工程学院 一种含短氟碳链涂层整理剂及其制备方法和应用
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JPH0647609B2 (ja) * 1985-08-30 1994-06-22 ティーディーケイ株式会社 フタロシアニン重合体の合成方法

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10211549B4 (de) * 2002-03-15 2004-07-29 Rudolf Gmbh & Co. Kg Chemische Fabrik Zubereitungen auf Basis von Wasser und/oder organischen Lösemitteln und deren Anwendung als Appretur auf Flächengebilden
DE10211549B9 (de) * 2002-03-15 2004-11-25 Rudolf Gmbh & Co. Kg Chemische Fabrik Zubereitungen auf Basis von Wasser und/oder organischen Lösemitteln und deren Anwendung als Appretur auf Flächengebilden
US7354458B2 (en) 2002-03-15 2008-04-08 Rudolf Gmbh & Co., Kg, Chemische Fabrik Preparations based on water and/or organic solvents and their use as a finish on flat materials
US8231802B2 (en) 2003-06-03 2012-07-31 Rudolf Gmbh Preparations for making planar structures oil-repellent and water-repellent, and use thereof

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Publication number Publication date
KR950012691B1 (ko) 1995-10-20
ES2047011T3 (es) 1994-02-16
DE3884746D1 (de) 1993-11-11
EP0314944A3 (de) 1991-10-09
KR890008391A (ko) 1989-07-10
AU616214B2 (en) 1991-10-24
SG105394G (en) 1995-03-17
US5047065A (en) 1991-09-10
HK495A (en) 1995-01-13
EP0314944A2 (de) 1989-05-10
ZA888291B (en) 1990-07-25
AU2401988A (en) 1989-05-11
DE3737753A1 (de) 1989-06-15
JPH01156581A (ja) 1989-06-20
CN1036419A (zh) 1989-10-18

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