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EP0051138B1 - Verfahren zum Hydrophobieren von Fasermaterial - Google Patents

Verfahren zum Hydrophobieren von Fasermaterial Download PDF

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Publication number
EP0051138B1
EP0051138B1 EP81107352A EP81107352A EP0051138B1 EP 0051138 B1 EP0051138 B1 EP 0051138B1 EP 81107352 A EP81107352 A EP 81107352A EP 81107352 A EP81107352 A EP 81107352A EP 0051138 B1 EP0051138 B1 EP 0051138B1
Authority
EP
European Patent Office
Prior art keywords
atoms
reaction product
reaction
group
acid ester
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
Application number
EP81107352A
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German (de)
English (en)
French (fr)
Other versions
EP0051138A1 (de
Inventor
Hans Deiner
Willy Dr. Bernheim
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.)
Chemische Fabrik Pfersee GmbH
Original Assignee
Chemische Fabrik Pfersee GmbH
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Filing date
Publication date
Application filed by Chemische Fabrik Pfersee GmbH filed Critical Chemische Fabrik Pfersee GmbH
Priority to AT81107352T priority Critical patent/ATE6530T1/de
Publication of EP0051138A1 publication Critical patent/EP0051138A1/de
Application granted granted Critical
Publication of EP0051138B1 publication Critical patent/EP0051138B1/de
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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
    • 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
    • D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
    • D06M13/503—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms without bond between a carbon atom and a metal or a boron, silicon, selenium or tellurium atom
    • D06M13/507—Organic silicon compounds without carbon-silicon bond
    • 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 relates to a process for hydrophobicizing fiber material, the fiber materials being treated with aqueous liquors which contain an emulsified organopolysiloxane with at least two, optionally modified hydroxyl groups, a polysilicic acid ester emulsion and a reaction product which is produced by the action of at least one halohydrin and / or epoxy group organic compound containing a nitrogen-bonded hydrogen atom-containing organic compound is obtained, which is water-soluble in the form of its salt or at least water-dispersible, contained and then be finished in a conventional manner.
  • DE-B-1 282597 discloses a process for rendering textiles repellent to water, the same using aqueous emulsions of organopolysiloxanes containing hydroxyl groups, silicic acid esters and a catalyst combination of esters of zirconic or titanium acid with aliphatic tertiary amines containing at least 2-ß-hydroxyalkyl groups wear, and water-soluble salts of zinc or cadmium treated with organic or inorganic acids and then briefly heated.
  • This known method only provides inadequate water repellency effects which no longer meet today's requirements (see comparative experiments in Example 1).
  • alkyl hydrogen polysiloxanes As organopolysiloxanes or at least to use them as crosslinking agents for organopolysiloxanes which contain groups capable of crosslinking.
  • these emulsified alkyl hydrogen polysiloxanes tend to release hydrogen, which leads to a loss of their effectiveness.
  • warehousing is difficult.
  • the present invention was therefore based on the object of obtaining good hydrophobizing effects on fiber materials in the absence of organohydrogenpolysiloxanes. This object was achieved by the method according to the invention.
  • organopolysiloxanes used are known (see, for example, "Ullmann's Encyclopedia of Industrial Chemistry", Urban & Schwarzenberg Publishing House, Kunststoff-Berlin, Volume 15, (1964), pages 784ff, section "Silicone Rubber”). Those organopolysiloxanes which carry terminal hydroxyl groups are preferably used. These hydroxyl groups can, however, also be modified, although the ability of these groups to crosslink must be ensured. Otherwise, the organopolysiloxanes are customary dialkyl, in particular dimethylpolysiloxanes, which may have been modified by special substituents.
  • the alkyl, in particular methyl groups in the reactive end groups-containing polysiloxanes can be substituted by phenyl, benzyl, ethylphenyl or ethyl groups.
  • organopolysiloxanes also play a role in which some of the alkyl groups are replaced by unsaturated organic groups, e.g. Vinyl groups, is replaced.
  • the organopolysiloxanes described are emulsified with the aid of nonionic or cationic emulsifiers.
  • Polyvinyl alcohols are particularly suitable as nonionic emulsifiers.
  • ethylene oxide conversion products of higher fatty acids, fatty alcohols, fatty acid amides and higher amines are also suitable.
  • the ethoxylation products of the higher amines can also be used in the form of their salts with low carboxylic acids, such as acetic, formic or propionic acids, or mineral acids, such as hydrochloric acid, hydrobromic acid or sulfuric acid.
  • emulsifiers examples are e.g. in GB-A-1 404356 and US-A-3748275.
  • Quaternary ammonium salts may be mentioned as cationic emulsifiers.
  • examples of such compounds are lauryl or cetylbenzyldimethylammonium chloride or octadecyloxymethylpyridinium chloride.
  • reaction products C) are particularly preferably used as emulsifiers for the organopolysiloxanes (see explanations below). This eliminates the need for these reaction products to be added separately to the equipment fleet, which considerably simplifies their manufacture.
  • the emulsifiers mentioned are in one Amount of at least 4% by weight, in particular 10-40% by weight, calculated as a 100% emulsifier, based on the organopolysiloxane with at least two, preferably terminal, optionally etherified or crosslinked esterified hydroxyl groups.
  • the organopolysiloxane emulsions A) can be prepared by known processes, so that further explanations are unnecessary.
  • a common procedure is e.g. in the aforementioned GB-A-1 404356.
  • the polysilicic acid esters used according to the invention which are derived from silicic acid esters of monohydric alcohols having 1 to 4 carbon atoms, are those with a molecular weight of about 300 to 750. Examples include methyl, n-propyl, n -Butyl polysilicate and especially called ethyl polysilicate. As comparative experiments have shown, monomeric silicic acid esters are less suitable for the process according to the invention, and it is surprising that the polysilicic acid esters described have such an excellent beneficial effect on the hydrophobizing effect.
  • the polysilicic acid esters mentioned are emulsified with the aid of nonionic emulsifiers.
  • the compounds already mentioned above can be used as nonionic emulsifiers, these compounds being used in an amount of about 4 to 40% by weight, based on the polysilicic acid ester.
  • the polysilicic acid ester emulsions can be prepared in a known manner. For this purpose, a pre-emulsion is first prepared, which is then e.g. is converted into a stable, storable emulsion by high-pressure homogenization. If nonionic emulsifiers are used to prepare emulsions B), it is readily possible to emulsify the organopolysiloxane together with the emulsification of the polysilicic acid ester.
  • reaction products C) further used according to the invention are known as such. They are described in the literature as emulsifiers for water-insoluble substances, but also as curing agents for silicones (see US Pat. Nos. 3,320,197, 3,848,022, 3,729,437 and 3,211,580 and GB-A-1,056,808). These reaction products are generally obtained by reacting organic compounds which contain at least one halohydrin and / or epoxy group with a compound which has nitrogen-bonded hydrogen atoms, reaction products being formed which are water-soluble or at least in the form of the salts are water dispersible.
  • organic compounds with at least one halohydrin and / or epoxy group are glycidyl or halogen, in particular chlorohydrin ethers of polyvalent phenols, such as 4,4'-dihydroxydiphenylpropane and methane, resorcinol or of polyvalent aliphatic alcohols, such as ethylene and propylene glycol, Glycerol, polyalkylene glycols and sorbitol or the glycidyl or halohydrin esters of dicarboxylic acids, such as adipic acid or terephthalic acid, and mixtures of the compounds mentioned.
  • Organopolysiloxanes containing epoxy groups are also quite suitable. The compounds containing epoxy groups are generally preferred for practical considerations.
  • di- or polyamines such as ethylene and propylene diamine, diethylenetriamine, triethylene tetramine, dipropylenetramine, cycloaliphatic diamines, such as 1,4-diaminocyclohexane and heterocyclic compounds with at least 2 secondary amine groups, such as piperazine.
  • Such compounds are also urea or imino urea or their derivatives (eg dicyandiamide, cyanamide, aryl or alkyl guanamines, melamine) or the heating products thereof. If these compounds are used to prepare the reaction products C), it is additionally necessary to use compounds of the formula to be used in which R is an alkyl group with 2 to 4 carbon atoms or an alkanol group with 2 to 5 carbon atoms, R 2 and R 3 are independently hydrogen, an alkyl group with 1 to 4 carbon atoms or an alkanol group with 2 to 5 carbon atoms and in the molecule at least 2 reactive hydrogen atoms are contained. If R 2 and R 3 are hydrogen, these compounds can also be used in the absence of urea or the urea derivatives to prepare the reaction products C). Examples of these compounds are described in US-A-3725502.
  • Both the organic compounds with at least one halohydrin and / or epoxy group and those with nitrogen-bonded hydrogen atoms can be wholly or partly by lipophilic residues, such as higher molecular weight alkyl, alkylcycloalkyl and / or alkylaryl residues with at least 8, preferably 12 to 18 C- Atoms are substituted.
  • lipophilic group-containing halohydrin and / or epoxy compounds are the reaction product of 1 mol of coconut fatty amine with 2 mol of epichlorohydrin and the bischlorohydrin ether of the glycerol monolauric acid ester.
  • N-stearylethylenediamine N-acylamidoamines and reaction products of fatty alcohol monochlorohydrin ethers or fatty acid chlorohydrin esters with di- or polyamines.
  • the starting material containing the lipophilic residues Compounds are also sufficient if only one of the reaction components for the preparation of the reaction products C) has all or part of lipophilic residues.
  • the amounts of the substances mentioned for the preparation of the reaction products C) are described in detail in the listed patents (see also patent claims).
  • the manufacture is also specified in detail.
  • the starting substances are reacted with one another in aqueous, aqueous / alcoholic or alcoholic solution at elevated temperature for up to 1 hour and then - if necessary - by adding volatile acids, e.g. Acetic acid or hydrochloric acid, the reaction is stopped and adjusted to the desired concentration with water.
  • volatile acids e.g. Acetic acid or hydrochloric acid
  • reaction products C) as emulsifiers for the organopolysiloxanes already described in more detail above, since this makes simplified storage and liquor production possible. In this case, too, better hydrophobic effects are obtained.
  • reaction products C particular preference is given to those whose preparation is described in US Pat. Nos. 3,320,197 and 3,211,580, since particularly favorable hydrophobicity values are obtained in this way.
  • the treatment liquors can be prepared in a simple manner by combining components A), B) and C) and diluting with water and adjusting the pH to 5.5 to 7.5, in particular 6 to 7, in a known manner with preferably volatile acids . So much of the 20 to 40% by weight polysiloxane emulsion A) is used that the liquor contains at least 6, in particular 8 to 50, g of organopolysiloxane per liter. From the polysilicic acid ester dispersion B), which generally contains 35 to 65% by weight of polysilicic acid ester, 2 to 30 g, in particular 2 to 20 g, per liter of finishing liquor are used.
  • the reaction product C which is generally an 8 to 25% solution, is used in amounts such that at least 6% by weight, in particular 10 to 40% by weight, of 100% reaction product C), based on organopolysiloxane, is used are present in the fleet. If the reaction product C) is used as an emulsifier for the organopolysiloxane emulsion A), which is preferred, the same will occur. Amounts to use and of course there is no need to add them later.
  • the treatment liquors obtained are extremely stable, so that the good hydrophobic effects are obtained even after a standing time of 12 to 24 hours.
  • the finishing liquor is applied to the material in customary quantities (pad pick-up, depending on the fiber material, 40 to 120% by weight) by padding, splashing, spraying or other known methods and is then completed by simple heating. In general, it is dried at up to 100 ° C. and condensed at 130 to 170 ° C. for about 2 to 5 minutes. However, it is also possible to carry out the aftertreatment at 110 ° C. for 10 to 20 minutes. It is a particular advantage of the method according to the invention that even low temperatures are sufficient to maintain the good hydrophobizing effects.
  • the present process for the hydrophobization of fiber materials, in particular textiles, can be combined with conventional crease-free finishing.
  • the known synthetic resins can be used.
  • Conventional compounds such as magnesium chloride, Zn salts and amine hydrochlorides are suitable as catalysts.
  • Fiber materials include leather, synthetic leather, paper, nonwovens and in particular textiles.
  • the fiber material preferably consists of natural or regenerated cellulose or mixtures of cellulose with animal or synthetic fibers.
  • fiber materials which contain animal, in particular wool, or synthetic fibers, in particular polyester, polyamide and polyacrylonitrile fibers, alone or in mixtures with one another, can also be finished according to the invention.
  • Textiles containing cellulose or cellulose are particularly preferably hydrophobized.
  • a cotton poplin fabric (approx. 230 g / m2) is impregnated with an aqueous liquor which contains 125 g / l of the emulsion given below and 40 g / l of the epoxyamine reaction product used in Example 1 of US-A-3320197 (pH 7, 2), squeezed to a liquor pickup of 72% and then dried at 100 ° C. for 10 minutes and condensed at 150 ° C. for 5 minutes.
  • the fabric equipped in this way has a what water absorption of 17% and a very good water repellent effect (4/4/4).
  • the fabric treated in this way has a water absorption of 72% and an insufficient beading effect (1).
  • the superiority of the method according to the invention is thus clearly recognizable.
  • the pH of the liquor is 7.3.
  • Example 1 The cotton poplin mentioned in Example 1 is equipped with these liquors immediately after production, after 2 hours and 12 hours of standing under the conditions mentioned in Example 1.
  • the cotton poplin described above is padded with these liquors (liquor absorption about 65%) and then dried at 110 ° C. for 15 minutes.
  • the fabric treated in this way has very good water repellency and a good beading effect.
  • an emulsion is prepared using 5 g of nonylphenol polyglycol ether (10 moles of ethylene oxide per mole of nonylphenol) as an emulsifier (emulsion B).

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Silicon Polymers (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Artificial Filaments (AREA)
EP81107352A 1980-09-23 1981-09-17 Verfahren zum Hydrophobieren von Fasermaterial Expired EP0051138B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT81107352T ATE6530T1 (de) 1980-09-23 1981-09-17 Verfahren zum hydrophobieren von fasermaterial.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3035824 1980-09-23
DE19803035824 DE3035824A1 (de) 1980-09-23 1980-09-23 Verfahren zum hydrphobieren von fasermaterial

Publications (2)

Publication Number Publication Date
EP0051138A1 EP0051138A1 (de) 1982-05-12
EP0051138B1 true EP0051138B1 (de) 1984-03-07

Family

ID=6112637

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81107352A Expired EP0051138B1 (de) 1980-09-23 1981-09-17 Verfahren zum Hydrophobieren von Fasermaterial

Country Status (5)

Country Link
US (1) US4390650A (es)
EP (1) EP0051138B1 (es)
AT (1) ATE6530T1 (es)
DE (1) DE3035824A1 (es)
ES (1) ES8206701A1 (es)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4502869A (en) * 1983-07-05 1985-03-05 Texaco Inc. Synthesis gas generation process with control of ratio of steam to dry gas
US5191734A (en) * 1990-04-24 1993-03-09 Kimberly-Clark Corporation Biodegradable latex web material
DE4117864A1 (de) * 1991-05-31 1992-12-03 Pfersee Chem Fab Waessrige dispersionen von polysiloxanen
US5227200A (en) * 1992-03-09 1993-07-13 Dow Corning Corporation Silicone containing automotive vinyl and rubber protectant
DE4330967A1 (de) * 1993-09-13 1995-03-16 Pfersee Chem Fab Organische Siliciumverbindungen enthaltende Zusammensetzungen für die Behandlung von Fasermaterialien
DE19857106C2 (de) * 1998-12-10 2000-10-26 Heinz Neubaur Badebekleidung aus einem wasserabweisenden Stoff und Verfahren zu ihrer Herstellung
US6756076B2 (en) * 2000-10-13 2004-06-29 Michael Brier Process for producing fabric articles having water-resistant and/or antimicrobial characteristics
US8013097B2 (en) 2007-04-11 2011-09-06 Dow Corning Corporation Silicone polyether block copolymers having organofunctional endblocking groups
US8268975B2 (en) * 2009-04-03 2012-09-18 Dow Agrosciences Llc Demulsification compositions, systems and methods for demulsifying and separating aqueous emulsions

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1769666U (de) 1955-01-17 1958-07-03 Conrad Mollenhauer Holzblasins Mundlochansatz fuer querfloeten, boehmfloeten od. dgl.
US3004871A (en) * 1959-07-23 1961-10-17 Gen Electric Rendering cellulosic materials non-adherent
BE613193A (es) * 1961-01-30
NL132432C (es) * 1963-03-26
US3418162A (en) * 1963-12-07 1968-12-24 Shinetsu Chem Ind Co Composition of waterproof agent and process for manufacture of waterproof cloth using the same
BE602682A (fr) 1964-02-19 1961-10-17 Hoechst Ag Durcissants pour organo-polysiloxanes
DE1231432B (de) 1964-12-01 1966-12-29 Boehme Fettchemie Gmbh Wasserloesliche polymere Verbindungen als Emulgiermittel zum Emulgieren von Silikonen in Wasser
NL131557C (es) 1965-05-26
GB1181347A (en) * 1967-06-26 1970-02-11 Dow Corning Polydimethylsiloxane Coatings
FR1575695A (es) * 1968-04-10 1969-07-25
CH882868A4 (es) * 1968-06-13 1970-02-13
DE1936886C3 (de) * 1969-07-19 1973-12-20 Chemische Fabrik Pfersee Gmbh, 8900 Augsburg Verfahren zur Herstellung von wasserlöslichen bzw. in Wasser selbst dispergierenden, in der Hitze vernetzenden Kondensationsprodukten und Verwendung dieser Kondensationsprodukte als Härtungskatalysatoren für Organopolysiloxane
BE756758A (fr) * 1969-09-29 1971-03-29 Rhone Poulenc Sa Emulsions aqueuses concentrees pour l'hydrofugation des textiles
US3772351A (en) * 1970-10-12 1973-11-13 Dow Corning Urea-functional organosilicon compounds
BE791827A (fr) 1971-11-25 1973-03-16 Pfersee Chem Fab Procede pour la fabrication d'emulsions stables d'organopolysiloxanes fortement visqueux reticulables
JPS4947436A (es) 1972-09-08 1974-05-08
GB1478126A (en) * 1973-08-28 1977-06-29 Nat Res Dev Water-repellent treatment

Also Published As

Publication number Publication date
EP0051138A1 (de) 1982-05-12
ES505681A0 (es) 1982-08-16
DE3035824C2 (es) 1988-09-15
DE3035824A1 (de) 1982-05-06
ATE6530T1 (de) 1984-03-15
US4390650A (en) 1983-06-28
ES8206701A1 (es) 1982-08-16

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