EP0190672B1 - Procédé d'imprégnation de fibres organiques - Google Patents

Procédé d'imprégnation de fibres organiques Download PDF

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Publication number
EP0190672B1
EP0190672B1 EP86101240A EP86101240A EP0190672B1 EP 0190672 B1 EP0190672 B1 EP 0190672B1 EP 86101240 A EP86101240 A EP 86101240A EP 86101240 A EP86101240 A EP 86101240A EP 0190672 B1 EP0190672 B1 EP 0190672B1
Authority
EP
European Patent Office
Prior art keywords
bonded
radicals
organopolysiloxane
sic
basic nitrogen
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
EP86101240A
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German (de)
English (en)
Other versions
EP0190672A2 (fr
EP0190672A3 (en
Inventor
Karl Dr.Dipl.-Chem. Huhn
Ingomar Dr.Dipl.-Ing. Kovar
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.)
Wacker Chemie AG
Original Assignee
Wacker Chemie AG
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Filing date
Publication date
Application filed by Wacker Chemie AG filed Critical Wacker Chemie AG
Priority to AT86101240T priority Critical patent/ATE63583T1/de
Publication of EP0190672A2 publication Critical patent/EP0190672A2/fr
Publication of EP0190672A3 publication Critical patent/EP0190672A3/de
Application granted granted Critical
Publication of EP0190672B1 publication Critical patent/EP0190672B1/fr
Anticipated expiration legal-status Critical
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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
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • 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
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups

Definitions

  • all organic fibers can be impregnated in the form of threads, yarns, nonwovens, mats, strands, woven, knitted or knitted textiles which have also been impregnated with organosilicon compounds.
  • fibers which can be impregnated by the process according to the invention are thus those made of keratin, in particular wool, polyvinyl alcohol, copolymers of vinyl acetate, cotton, rayon, hemp, natural silk, polypropylene, polyethylene, polyester, polyurethane, polyamide, cellulose and mixtures from at least two such fibers.
  • the fibers can be of natural or synthetic origin.
  • the textiles can be in the form of fabric webs or items of clothing or parts of items of clothing.
  • the diorganosiloxane units in the organopolysiloxane (1), in which the two SiC-bonded organic radicals are monovalent hydrocarbon radicals, are preferably those represented by the formula can be reproduced, where R is the same or different, monovalent hydrocarbon radicals, R1 is hydrogen or from carbon and hydrogen atom (s) and optionally an ether oxygen atom, radicals free of multiple bonds with 1 to 15 carbon atoms per radical and a is 0 or 1.
  • radicals R preferably contain 1 to 18 carbon atoms per radical.
  • radicals R are alkyl radicals, such as the methyl, ethyl, n-propyl and isopropyl radical, and butyl, octyl, tetradecyl and octadecyl radicals; aliphatic hydrocarbon radicals with at least one double bond, those of the vinyl, allyl and butadienyl radical; cycloaliphatic hydrocarbon radicals, such as the cyclohexyl radical; aromatic hydrocarbon radicals such as the phenyl radical and naphthyl radicals; Alkaryl groups such as tolyl groups; and aralkyl radicals, such as the benzyl radical.
  • at least 80% of the number of SiC-bonded hydrocarbon residues in the organopolysiloxane (1) are preferably methyl residues.
  • hydrocarbon radicals R insofar as they represent free hydrocarbon radicals with a maximum of 15 carbon atoms per radical, also apply fully to the hydrocarbon radicals R 1, with the methyl, ethyl and isopropyl radicals being preferred.
  • a preferred example of a radical R 1 composed of carbon and hydrogen atoms and an ether oxygen is the rest of the formula CH3O (CH2) 2-.
  • the organopolysiloxanes (1) preferably contain at least 100 diorganosiloxane units, in which the two SiC-bonded organic radicals are monovalent hydrocarbon radicals, per molecule.
  • the monoorganosiloxane units in which the SiC-bonded radicals with basic nitrogen are present in the organopolysiloxane (1) are preferably those represented by the formula can be reproduced while the diorganosiloxane units, in which SiC-bound radicals with basic nitrogen are present in the organopolysiloxane (1), preferably those which are represented by the formula can be reproduced, where R, R1 and a each have the meaning given above, R2 is hydrogen or identical or different alkyl or aminoalkyl or iminoalkyl radicals and R3 is identical or different, divalent hydrocarbon radicals and b is 0, 1 or 2.
  • alkyl radicals R also apply fully to alkyl radicals R2.
  • radical R 3 is that of the formula - (CH2) 3- particularly preferred. Further examples of R3 radicals are those of the formula
  • the organopolysiloxane (1) or the organopolysiloxane (1) must have at least one monoorganosiloxane unit with a Sic-bonded radical contain with basic nitrogen and at least one diorganosiloxane unit with an SiC-bonded residue with basic nitrogen, one of these units per molecule of organopolysiloxane (1) being sufficient.
  • the sum of the number of monoorganosiloxane units with an SiC-bonded radical with basic nitrogen and the number of diorganosiloxane units with an SiC-bonded radical with basic nitrogen is at most 20% of the number of diorganosiloxane units, in which the two SiC-bonded organic radicals are monovalent hydrocarbon radicals in order to avoid a risk of yellowing of the impregnated fibers and to avoid unnecessary effort.
  • the ratio of the number of monoorganosiloxane units with basic nitrogen to the number of diorganosiloxane units with basic nitrogen is preferably 0.9: 3 to 3: 1, in particular 0.9: 1 to 1.1: 1.
  • the organopolysiloxane (1) or a mixture of at least two different types of organopolysiloxane (1) preferably has an average viscosity of 100 to 100,000 mPa.s at 25 ° C.
  • the organopolysiloxanes (1) can be prepared in a manner known per se for any of the organopolysiloxanes which contain monovalent SiC-bonded radicals containing basic nitrogen.
  • organopolysiloxanes (2) with at least 3 Si-bonded hydrogen atoms per molecule the same organopolysiloxanes containing at least 3 Si-bonded hydrogen atoms can also be used in the process according to the invention, which could be used in all previously known processes for impregnating organic fibers.
  • the silicon valences which are saturated by hydrogen and siloxane oxygen atoms, are preferably methyl, ethyl or Saturated phenyl radicals or a mixture of at least two such hydrocarbon radicals. It is further preferred that each silicon atom to which a hydrogen atom is bound also has one of the preferred hydrocarbon radicals mentioned above bound.
  • Particularly preferred organopolysiloxanes (2) with at least 3 Si-bonded hydrogen atoms per molecule are those of the formula wherein R4 is hydrogen or the methyl, ethyl or phenyl radical and p is an integer from 10 to 500, with the proviso that at most one hydrogen atom is bonded to a silicon atom and that the ratio of R 4th 2nd SiO units in which both R4 are hydrocarbon radicals to the units with Si-bonded hydrogen is 0: 1 to 4: 1.
  • R4 also preferably denotes a methyl radical if it is not hydrogen.
  • organopolysiloxane can also be used as organopolysiloxanes (2) with at least 3 Si-bonded hydrogen atoms per molecule.
  • Organopolysiloxane (2) with at least 3 Si-bonded hydrogen atoms per molecule can also be used in the process according to the invention in the same amounts as in the previously known processes for impregnating organic fibers in connection with directly on silicon bound organopolysiloxane containing condensable groups could be used.
  • Such organopolysiloxane is preferably used in amounts of 0.01 to 0.50 part by weight of Si-bonded hydrogen per 100 parts by weight of organopolysiloxane (1).
  • any catalysts for the condensation of condensable groups directly bonded to silicon can also be used in the process according to the invention which have hitherto been used to promote the condensation of directly bonded to silicon , condensable groups could be used.
  • catalysts are, in particular, carboxylic acid salts of tin or zinc, it being possible for hydrocarbon radicals to be bonded directly to tin, such as di-n-butyltin dilaurate, tin octoates, di-2-ethyltin dilaurate, di-n-butyltin di-2-ethylhexoate, di-2- ethylhexyltin di-2-ethylhexoate, dibutyl or dioctyltin diacylates, the acylate groups each being derived from alkanoic acids having 3 to 16 carbon atoms per acid, in which at least two of the valences of the carbon atom bonded to the carboxyl group are saturated by at least two carbon atoms other than that of the carboxy group , and zinc octoates.
  • catalysts (3) are alkyl titanates, such as butyl titanates and triethanolamine titanate, and zir
  • catalysts (3) The same or different molecules of this type of catalyst can also be used as catalysts (3).
  • the catalysts (3) can also be used in the process according to the invention in the same amounts in which they could previously be used to promote the condensation of condensable groups bonded directly to silicon.
  • Catalyst (3) is preferably used in amounts of 1 to 10 parts by weight per 100 parts by weight of organopolysiloxane (1).
  • further substances such as can conventionally be used for the impregnation of organic fibers, can optionally also be used in the process according to the invention.
  • further substances in the terminal units are dimethylpolysiloxanes each having an Si-bonded hydroxyl group and having a viscosity of at most 10,000 mPa.s at 25 ° C, dimethylpolysiloxanes endblocked by trimethylsiloxy groups and having a viscosity of at most 10,000 mPa.s at 25 ° C and, especially if the fibers to be impregnated consist at least in part of cellulose or cotton, so-called "crease-free finishes", such as dimethyldihydroxyethylene urea (DMDHEU) in a mixture with zinc nitrate or magnesium chloride.
  • DMDHEU dimethyldihydroxyethylene urea
  • the substances used in the process according to the invention can be applied to the fibers to be impregnated in undiluted form or in the form of solutions in organic solvent or in the form of aqueous emulsions. If aqueous emulsions are used, these emulsions can contain, in addition to water, dispersant and the above-mentioned substances to be dispersed, thickeners, such as poly-N-vinylpyrrolidone.
  • the substances used in the process according to the invention are preferably applied in the form of aqueous emulsions to the fibers to be impregnated. As dispersants in these dispersions are nonionic and cationogenic emulsifiers preferred. These emulsions can be prepared in a manner known for the emulsification of organopolysiloxanes.
  • the substances used in the process according to the invention can be applied to the fibers to be impregnated in any suitable and well-known manner for the impregnation of fibers, e.g. B. by dipping, brushing, pouring, spraying, including spraying from aerosol packaging, rolling, padding or printing.
  • the substances used in the process according to the invention are preferably applied in amounts such that the weight gain of the fiber by these substances, minus any diluents which may be used, is 1 to 20 percent by weight, based on the weight of the fiber.
  • the organosilicon compounds used in the process according to the invention are crosslinked on the fiber at room temperature. B. accelerated 50 ° to 180 ° C.
  • a fabric made of 50% cotton and 50% polyester with a weight of 210 g / m2 is immersed in an emulsion that 40 g / l of the emulsion, the preparation of which was described in Example 1 under b), 4 g / l of the emulsion, the preparation of which was described in Example 1 under c), 4 g / l of the emulsion, the preparation of which was described in Example 1 under d), 80 g / l DMDHEU 10 g / l magnesium chloride and contains the rest of water, and then squeezed to 80% fluid intake.
  • the fabric so impregnated is then heated to 150 ° C. for 10 minutes.
  • the impregnated fabric thus obtained has a soft, elastic handle, which is still present in a household washing machine even after 5 delicates at 60 ° C.
  • the knitted fabrics impregnated according to Example 1 and the knitted fabrics impregnated according to the two comparative tests were evaluated for their grip by 9 people who had no knowledge of which knitted fabrics according to the comparative tests and which knitted fabric was impregnated according to Example 1. Before and after 5 delicates at 40 ° C. in a household washing machine, the knitted fabric impregnated according to Example 1 was rated 5 times and the knitted fabric impregnated according to the two comparative tests was rated twice.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Silicon Polymers (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paper (AREA)

Claims (3)

  1. Procédé d'imprégnation de fibres organiques avec
    1) un polyorganosiloxane à groupes condensables directement liés au silicium et qui comporte, en plus de motifs diorganosiloxaniques dont les deux radicaux organiques à liaison SiC sont des radicaux hydrocarbonés monovalents, au moins deux radicaux à azote basique monovalents à liaison SiC,
    2) un polyorganosiloxane ayant par molécule au moins trois atomes d'hydrogène liés à du silicum, et
    3) un catalyseur pour la condensation des groupes condensables directement liés au silicium, et
    procédé caractérisé en ce que les radicaux à azote basiques en liaison SiC du polyorganosiloxane (1) se trouvent aussi bien dans des motifs de mono-organosiloxane que dans ceux de diorganosiloxane.
  2. Procédé selon la revendication 1, caractérisé en ce que le rapport du nombre de motifs de monoorganosiloxane à azote basique au nombre de motifs de diorganosiloxane à azote basique est compris entre 0,1 : 3 et 3 : 1.
  3. Procédé selon la revendication 1 ou 2, caractérisé en ce que le rapport du nombre de motifs de monoorganosiloxane à azote basique au nombre de motifs de diorganosiloxane à azote basique est compris entre 0,9 : 1 et 1,1 : 1.
EP86101240A 1985-02-01 1986-01-30 Procédé d'imprégnation de fibres organiques Expired - Lifetime EP0190672B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT86101240T ATE63583T1 (de) 1985-02-01 1986-01-30 Verfahren zur impraegnierung von organischen fasern.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19853503457 DE3503457A1 (de) 1985-02-01 1985-02-01 Verfahren zur impraegnierung von organischen fasern
DE3503457 1985-02-01

Publications (3)

Publication Number Publication Date
EP0190672A2 EP0190672A2 (fr) 1986-08-13
EP0190672A3 EP0190672A3 (en) 1988-09-28
EP0190672B1 true EP0190672B1 (fr) 1991-05-15

Family

ID=6261426

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86101240A Expired - Lifetime EP0190672B1 (fr) 1985-02-01 1986-01-30 Procédé d'imprégnation de fibres organiques

Country Status (8)

Country Link
US (1) US4720520A (fr)
EP (1) EP0190672B1 (fr)
JP (1) JPS61179376A (fr)
KR (1) KR890001790B1 (fr)
AT (1) ATE63583T1 (fr)
BR (1) BR8600117A (fr)
CA (1) CA1274731A (fr)
DE (2) DE3503457A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4800026A (en) * 1987-06-22 1989-01-24 The Procter & Gamble Company Curable amine functional silicone for fabric wrinkle reduction
DE3727181A1 (de) * 1987-08-14 1989-02-23 Wacker Chemie Gmbh Verwendung von selbstvernetzenden vinylesterdispersionen mit reduziertem beziehungsweise ohne formaldehydgehalt zur verfestigung textiler fasergebilde
JPS6461576A (en) * 1987-08-27 1989-03-08 Lion Corp Gloss preventing composition
DE3730413A1 (de) * 1987-09-10 1989-03-30 Wacker Chemie Gmbh Verfahren zur impraegnierung von organischen fasern
GB8725921D0 (en) * 1987-11-05 1987-12-09 Precision Proc Textiles Ltd Treatment of wool
EP0360383A3 (fr) * 1988-09-21 1991-12-11 International Paper Company Fibre de coton élastique et sa méthode
GB8828414D0 (en) * 1988-12-06 1989-01-05 Precision Proc Textiles Ltd Method for treatment of cellulosic fibres
GB9303815D0 (en) * 1993-02-25 1993-04-14 Unilever Plc Use of fabric treatment compositions
DE102006052730A1 (de) 2006-11-08 2008-05-15 Wacker Chemie Ag Verfahren zur Behandlung von Füllfasern mit wässrigen Dispersionen von Organopolysiloxanen

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1419968A (fr) * 1963-12-07 1965-12-03 Shinetsu Chem Ind Co Perfectionnements apportés aux compositions et procédés pour imperméabiliser des étoffes
GB1434017A (en) * 1972-07-15 1976-04-28 Dow Corning Ltd Treatment of fibres
GB1570983A (en) * 1976-06-26 1980-07-09 Dow Corning Ltd Process for treating fibres
JPS5328468A (en) * 1976-08-27 1978-03-16 Citizen Watch Co Ltd Electronic wristwatch with electronic calculator
JPS57111354A (en) * 1980-12-29 1982-07-10 Toray Silicone Co Ltd Organopolysiloxane composition
DE3104582A1 (de) * 1981-02-10 1982-09-02 Wacker-Chemie GmbH, 8000 München "verfahren zur impraegnierung von textilen flaechengebilden"
JPS5825789A (ja) * 1981-08-07 1983-02-16 Matsushita Electric Ind Co Ltd 多方式受信用カラ−テレビ受像機
JPS61296184A (ja) * 1985-06-20 1986-12-26 信越化学工業株式会社 繊維処理剤

Also Published As

Publication number Publication date
JPS61179376A (ja) 1986-08-12
KR890001790B1 (ko) 1989-05-22
DE3503457A1 (de) 1986-08-07
BR8600117A (pt) 1986-09-23
US4720520A (en) 1988-01-19
KR860006597A (ko) 1986-09-13
CA1274731A (fr) 1990-10-02
ATE63583T1 (de) 1991-06-15
DE3679206D1 (de) 1991-06-20
EP0190672A2 (fr) 1986-08-13
EP0190672A3 (en) 1988-09-28
JPS641591B2 (fr) 1989-01-12

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