EP0016907A2 - Produit antifeutrant pour laine - Google Patents

Produit antifeutrant pour laine Download PDF

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Publication number
EP0016907A2
EP0016907A2 EP80100297A EP80100297A EP0016907A2 EP 0016907 A2 EP0016907 A2 EP 0016907A2 EP 80100297 A EP80100297 A EP 80100297A EP 80100297 A EP80100297 A EP 80100297A EP 0016907 A2 EP0016907 A2 EP 0016907A2
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EP
European Patent Office
Prior art keywords
mol
und
bis
radical
radicals
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.)
Granted
Application number
EP80100297A
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German (de)
English (en)
Other versions
EP0016907A3 (en
EP0016907B1 (fr
Inventor
Götz Dr. Koerner
Friedhelm Nickel
Günter Dr. Schmidt
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.)
Evonik Goldschmidt GmbH
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TH Goldschmidt AG
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Publication date
Application filed by TH Goldschmidt AG filed Critical TH Goldschmidt AG
Publication of EP0016907A2 publication Critical patent/EP0016907A2/fr
Publication of EP0016907A3 publication Critical patent/EP0016907A3/de
Application granted granted Critical
Publication of EP0016907B1 publication Critical patent/EP0016907B1/fr
Expired 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
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences

Definitions

  • the invention relates to a preparation for shrink-proofing wool.
  • GB-PS 746 307 describes a method for preventing the shrinkage of the wool, the wool fibers being equipped with certain organopolysiloxanes. A certain degree is thereby achieved in shrink resistance, but this effect is not washable.
  • reaction products are used in the form of organic solutions, it can be seen that the effect which can be achieved is too small for successful use in practice. It also separates from the solvent-containing Liquors by the action of humidity after some time siloxane gel from which act e-B to the devices plugged the wool.
  • the invention is therefore based on the object of finding a preparation for shrink-proofing wool which contains compounds, both in emulsion form and in the form of an organic solution, which are suitable for making wool shrink-proof, these properties even after repeated washing of the wool in usual washing machines should be preserved. It is in particular an object of the invention to find a preparation which can be used selectively in the various stages of wool processing through different types of application. The aim should be that the treatment of the wool can also take place after the wool has been dyed and that the known treatment processes, such as the pull-out the block method can also be used.
  • the active ingredient contained in the preparation must not adversely affect the so-called feel of the wool or the knitted fabrics and fabrics made from the wool.
  • the organopolysiloxane skeleton which is formed from the units a 1 ) and a 2 ), is a slightly to moderately branched siloxane.
  • the units a 1 ). and a 2 ) are preferably randomly distributed in the siloxane molecule.
  • these organopolysiloxanes can have 0.1 to 10 mol% of polyoxyalkylene radicals.
  • wool-affine groups are bound to the organopolysiloxane skeleton. These wool-affine groups are mercaptoalkyl or mercaptoaryl residues, aminoalkyl residues or anionic groups bonded to Si atoms via C atoms. It is sufficient if, in addition to the polyoxyalkylene radicals, only one of the three types of wool-related groups shown, e.g. 0.03 to 3 mol% of mercaptoalkyl or mercaptoaryl radicals are contained.
  • aminoalkyl radicals are present in the molecule in amounts of 0.06 to 6 mol%.
  • polyoxyalkylene radicals 0.1 to 10 mol% of anionic groups bonded to Si atoms via C atoms are present.
  • these three different groupings can also exist side by side, e.g. Mercaptoalkyl residues together with aminoalkyl residues or mercaptoalkyl residues with anionic groups. All three different groups can also be incorporated into the molecule at the same time.
  • R 1 and R 2 groups are methyl groups, of which, however, up to 10 mol% through longer-chain alkyl. or aryl residues can be replaced.
  • alkyl or aryl radicals are the ethyl, propyl, dodecyl or phenyl radical.
  • the polyoxyalkylene radical preferably corresponds to the formula where Y is the or the trimethylsilyl radical and y has a value from 4 to 20.
  • polyoxyalkylene block contains oxypropylene units in addition to oxyethylene units, polyoxyalkylene radicals with at least 40 mol% of polyoxyethylene units are preferred.
  • R 1 and R 2 should consist of 0.1 to 10 mol% of polyoxyalkylene radicals, a range of 0.3 to 5 mol% is particularly preferred.
  • Examples of mercaptoalkyl or mercaptoaryl radicals bonded to the polysiloxane skeleton are the mercaptomethyl, 2-mercaptoethyl, 3-mercaptopropyl, 3-mercaptoisobutyl or mercaptophenyl radical.
  • the 3-mercaptopropyl radical is particularly preferred.
  • mercaptoalkyl or mercaptoaryl residues are bound to the organopolysiloxane molecule, preferably 0.1 to 1 mol%.
  • Suitable aminoalkyl radicals which are also preferably used, are the 3- (2-aminoethyl) aminopropyl or the. 3-aminopropyl group.
  • suitable aminoalkyl radicals are the 4- (2-aminoethyl) aminobutyl radical or the 3- (2-aminoethyl -) - aminoisobutyl radical.
  • aminoalkyl radicals form 0.06 to 6 mol% of the radicals R 1 and R 2 .
  • the preferred range is 0.2 to 2 mol%.
  • Anionic groups can also be bound to the organopolysiloxane molecule. These anionic groups are bound to the silicon atom by a divalent hydrocarbon radical.
  • the carbon chain of the divalent hydrocarbon radical can be interrupted by oxygen, nitrogen or sulfur atoms.
  • the groups are particularly suitable as anionic groups where m is 0 or 1 and X is an - ⁇ - residue or the group - OR 4 .
  • R 4 is a hydrogen radical or an alkyl radical with 1 to 4 carbon atoms.
  • Examples of such groups are 0.1 to 10 mol% of the groups R 1 and R 2 are formed by such anionic groups, but preferably 0.3 to 6 mol%.
  • the preparations according to the invention can be produced in two different ways.
  • the reaction can also be carried out in the form of cocondensation in an anhydrous medium.
  • cyclic siloxanes can be used in a known manner (US Pat. No. 2,891,920), optionally from their mixture with organomodified di (tri) alkoxysilanes, such as, for example. 3-mercaptopropyl-methyl-diethoxysilane, 3-aminopropyl-methyl-diethoxysilane or silanes of the formula the corresponding organomodified a, w-polydimethylsiloxane diols are prepared in the presence of anionic or cationic polymerization catalysts.
  • organomodified di (tri) alkoxysilanes such as, for example. 3-mercaptopropyl-methyl-diethoxysilane, 3-aminopropyl-methyl-diethoxysilane or silanes of the formula the corresponding organomodified a, w-polydimethylsiloxane diols are prepared in the presence of anionic or cationic polymerization catalysts.
  • This siloxane diols can then be reacted further with trialkoxysilanes modified or modified with polyalkylene glycol ether or with SH or amino groups and also with silanes, for example of the formula via which an anionic group can be introduced into the organopolysiloxane.
  • the synthesis of the organomodified alkoxysilanes is known to the person skilled in the art.
  • organopolysiloxanes in the non-aqueous phase, it is expedient to start from a sulfuric acid ester of an organosilicon alcohol of the formula out.
  • This starting product which also has a potential anionic group, can in the presence of an acid acceptor, such as, for example, an amine, with ⁇ , ⁇ -polydimethylsiloxane diols, for example of the formula be implemented.
  • an acid acceptor such as, for example, an amine
  • the reaction product also contains terminally reactive SiOH groups which are capable of cocondensation with the alkoxy groups of the silanes modified with polyalkylene glycol ether, optionally also with mercaptoalkyl.
  • the solvents are removed by simple distillation.
  • organopolysiloxanes thus prepared can also be converted into aqueous preparations according to the invention by incorporating water, possibly in the presence of suitable emulsifiers.
  • a suitable solvent such as methylene chloride
  • the reactants are diluted with methylene chloride to a volume of 500 ml.
  • the partially condensed partial hydrolyzate was obtained by the reaction of 3-mercaptopropyltriethoxysilane with 2% hydrochloric acid in methylene chloride.
  • the solvent is then removed by simple distillation.
  • the reaction product which is freed from the triethylammonium chloride by pressure filtration, is a low-viscosity, slightly yellowish organopolysiloxane, the residues R 1 and R 2 of which are methyl residues, of which, however, 1.35 mol% Residues, 0.71 mol% are replaced by - (CH 2 ) 3 - [OC 2 H 4 ] 16.3 H residues and 0.32 mol% by - (CH 2 ) 3 -SH residues.
  • aqueous preparations with active substance contents of 1 to 50% by weight can be produced from the organopolysiloxane.
  • the solvent is carefully distilled off and the reaction product is freed from triethylammonium chloride by pressure filtration.
  • the residues R 1 and R 2 of which are 3.13 mol% Residues, to 1.17 mol% Residues and 0.32 mol% consist of - (CH 2 ) 3 -SH residues - the remaining residues are methyl residues - stable preparations with siloxane contents of 1.0 to 50% can be prepared by simply stirring in water.
  • the finely divided preparation thus produced contains an organopolysiloxane in which the radicals R 1 and R 2 are 1.29 mol% and to 0.322 mol% consisting of - (CH 2 ) 3 -SH residues; the remaining residues are methyl residues.
  • the potassium hydroxide solution contained in the emulsion is neutralized by adding 12 g of a 10% acetic acid.
  • the finely divided aqueous preparation contains an organopolysiloxane, the residues R 1 and R 2 of which are methyl residues, of which 0.33 mol%, however Residues and 0.33 mol% are replaced by - (CH 2 ) 3 -SH residues.
  • a 95 ° C. hot emulsifier solution corresponding to Example 3 is added dropwise with vigorous stirring with 167 g (0.56 mol) of octamethylcyclotetrasiloxane and 15.95 g (0.03 mol) transferred. After the dropwise addition, stirring is continued for 1 h and 6.05 g (0.027 mol) of 3- (aminoethyl) aminopropyltrimethoxysilane are added. Following a further 30 minute stirring phase, the mixture is cooled to 40 ° C. and the emulsion is neutralized by adding 16 g of 10% acetic acid.
  • the finely divided aqueous preparation contains an organopolysiloxane in which the radicals R 1 and R 2 comprise 0.65 mol% Residues and 0.59 mol% consist of - (CH 2 ) 3 -NH- (CH 2 ) 2 -NH 2 residues; the remaining residues are methyl residues.
  • an emulsifier solution is prepared, which, after heating to 95 ° C. with vigorous stirring, is added via a dropping funnel to 167 g (0.56 mol) of octamethyl cyclotetrasiolxan adds. After stirring for a further 60 min, 27.98 g (0.03 mol) are added dropwise and stir again for 30 min. The emulsion is then cooled to 40 ° C. and neutralized by adding 12 g of 10% acetic acid.
  • the finely divided aqueous preparation contains an organopolysiloxane, the residues R 1 and R 2 of which are methyl residues, of which, however, 0.66 mol% Leftovers are replaced.
  • organopolysiloxanes a consisting of the units a 1 ) and a 2
  • 167.00 g (0.56 mol) of octamethylcyclotetrasiloxane, 5.61 g (O, O15 mol) 27.98 g (0.03 mol) and 2.95 g (0.015 mol) of 3-mercaptopropyltrimethoxysilane were added to the emulsifier solution via a dropping funnel. After the various components have been added, the mixture is stirred vigorously for 60 minutes. The emulsion is then cooled to 40 ° C. and the acid obtained is neutralized by adding 11 g of a 1 molar potassium hydroxide solution.
  • the finely divided aqueous preparation contains an organopolysiloxane in which the residues R 1 and R 2 are 0.33 mol% Residues, to 0.66 mol% Residues and 0.33 mol% consist of - (CH 2 ) 3 -SH residues; the remaining residues are methyl residues.
  • the unfinished sample showed a heavily matted surface.
  • the handle of the treated samples was also significantly softer after washing than the handle of the untreated material after washing and corresponded to the handle before washing.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Silicon Polymers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP80100297A 1979-03-23 1980-01-22 Produit antifeutrant pour laine Expired EP0016907B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB7910341 1979-03-23
GB7910341 1979-03-23

Publications (3)

Publication Number Publication Date
EP0016907A2 true EP0016907A2 (fr) 1980-10-15
EP0016907A3 EP0016907A3 (en) 1981-03-18
EP0016907B1 EP0016907B1 (fr) 1982-02-17

Family

ID=10504098

Family Applications (1)

Application Number Title Priority Date Filing Date
EP80100297A Expired EP0016907B1 (fr) 1979-03-23 1980-01-22 Produit antifeutrant pour laine

Country Status (5)

Country Link
US (1) US4283191A (fr)
EP (1) EP0016907B1 (fr)
JP (1) JPS584114B2 (fr)
AU (1) AU529018B2 (fr)
DE (1) DE3060191D1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0313867A3 (en) * 1987-10-16 1990-06-13 Th. Goldschmidt Ag Organopolysiloxanes with bunte salt groups
US5269950A (en) * 1989-06-05 1993-12-14 Sanyo Chemical Industries, Ltd. Textile treating compositions
EP2773647B1 (fr) * 2011-11-04 2016-12-28 Dow Corning Corporation Organosilanes hydrophiles

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3034380A1 (de) * 1980-09-12 1982-03-25 Th. Goldschmidt Ag, 4300 Essen Zubereitung zum schrumpffestmachen von wolle
JPS57171768A (en) * 1981-04-15 1982-10-22 Shinetsu Chem Ind Co Fiber treating agent
DE3417912C1 (de) * 1984-05-15 1985-07-25 Goldschmidt Ag Th Betaingruppen enthaltende Siloxane,deren Herstellung und Verwendung in kosmetischen Zubereitungen
US5336419A (en) * 1990-06-06 1994-08-09 The Procter & Gamble Company Silicone gel for ease of ironing and better looking garments after ironing
DE4100703A1 (de) * 1991-01-11 1992-07-16 Chu Tjoei Ho Textilausruestungsmittel
US5532023A (en) * 1994-11-10 1996-07-02 The Procter & Gamble Company Wrinkle reducing composition
JPH10508912A (ja) * 1994-11-10 1998-09-02 ザ、プロクター、エンド、ギャンブル、カンパニー しわを減少させる組成物
US20070190872A1 (en) * 2006-02-16 2007-08-16 Weber Robert F Fire retardant silicone textile coating

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB594901A (en) 1945-04-11 1947-11-21 Wolsey Ltd Improvements relating to the treatment of materials consisting wholly or partly of wool
GB613267A (en) 1946-06-14 1948-11-24 Wolsey Ltd Improvements relating to the shrinkproofing of materials consisting wholly or partlyof wool
GB629329A (en) 1947-05-05 1949-09-16 Wolsey Ltd Improvements relating to the shrinkproofing of materials consisting wholly or partlyof wool
US2728692A (en) 1953-04-20 1955-12-27 Dow Corning Method of preventing shrinkage of wool
US2891290A (en) * 1957-07-16 1959-06-23 Gen Bronze Corp Window scupper arrangement
NL279187A (fr) * 1961-06-01
CH106968D (fr) * 1965-01-21 1900-01-01
DE1594953A1 (de) * 1966-05-28 1969-07-03 Rotta Chem Fab Theodor Verfahren zur Ausruestung von Fasergut mit Polysiloxanen
GB1431321A (en) * 1973-01-30 1976-04-07 Ici Ltd Surface treating compositions
CH615968D (fr) * 1967-04-26 1900-01-01
GB1396509A (en) * 1971-08-28 1975-06-04 Dow Corning Ltd Treatment of keratinous fibres
US3876459A (en) * 1973-06-29 1975-04-08 Dow Corning Treatment of fibres
GB1502265A (en) * 1974-05-28 1978-03-01 Dow Corning Ltd Treatment of fibres
AU1823676A (en) * 1975-10-13 1978-04-06 Commw Scient Ind Res Org Treatment of wool with polyorganosiloxanes
GB1548224A (en) * 1976-02-12 1979-07-04 Goldschmidt Ag Th Organosilicon compounds and textile fibre dressings which contain these compounds
GB1572397A (en) * 1976-06-11 1980-07-30 Dow Corning Ltd Fibre treatment composition and process

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0313867A3 (en) * 1987-10-16 1990-06-13 Th. Goldschmidt Ag Organopolysiloxanes with bunte salt groups
US5269950A (en) * 1989-06-05 1993-12-14 Sanyo Chemical Industries, Ltd. Textile treating compositions
EP2773647B1 (fr) * 2011-11-04 2016-12-28 Dow Corning Corporation Organosilanes hydrophiles

Also Published As

Publication number Publication date
AU5673280A (en) 1980-09-25
JPS55128076A (en) 1980-10-03
EP0016907A3 (en) 1981-03-18
EP0016907B1 (fr) 1982-02-17
US4283191A (en) 1981-08-11
DE3060191D1 (en) 1982-03-25
JPS584114B2 (ja) 1983-01-25
AU529018B2 (en) 1983-05-19

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