EP1005584A1 - Laine a finissage sans feutre et isocyanates autodispersants utilises a cet effet - Google Patents

Laine a finissage sans feutre et isocyanates autodispersants utilises a cet effet

Info

Publication number
EP1005584A1
EP1005584A1 EP98946313A EP98946313A EP1005584A1 EP 1005584 A1 EP1005584 A1 EP 1005584A1 EP 98946313 A EP98946313 A EP 98946313A EP 98946313 A EP98946313 A EP 98946313A EP 1005584 A1 EP1005584 A1 EP 1005584A1
Authority
EP
European Patent Office
Prior art keywords
groups
isocyanates
nco
methyl
self
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.)
Withdrawn
Application number
EP98946313A
Other languages
German (de)
English (en)
Inventor
Bernhard Jansen
Ferdinand Kümmeler
Helga Thomas
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.)
Bayer Chemicals AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP1005584A1 publication Critical patent/EP1005584A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/703—Isocyanates or isothiocyanates transformed in a latent form by physical means
    • C08G18/705—Dispersions of isocyanates or isothiocyanates in a liquid medium
    • C08G18/706—Dispersions of isocyanates or isothiocyanates in a liquid medium the liquid medium being water
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • 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
    • D06M10/00—Physical treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, e.g. by ultrasonic waves, corona discharge, irradiation, electric currents or magnetic fields; Physical treatment combined with treatment with chemical compounds or elements
    • D06M10/02—Sonic or ultrasonic waves; Corona discharge
    • D06M10/025—Corona discharge or low temperature plasma
    • 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
    • D06M10/00—Physical treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, e.g. by ultrasonic waves, corona discharge, irradiation, electric currents or magnetic fields; Physical treatment combined with treatment with chemical compounds or elements
    • D06M10/04—Physical treatment combined with treatment with chemical compounds or elements
    • D06M10/08—Organic compounds
    • D06M10/10—Macromolecular compounds
    • 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
    • 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
    • D06M15/568—Reaction products of isocyanates with polyethers
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/10—Animal fibres
    • D06M2101/12—Keratin fibres or silk

Definitions

  • the invention relates to wool finished with a felt-free finish, a process for its production by a) a pretreatment with a low-pressure plasma b) a post-treatment with aqueous dispersions of self-dispersing isocyanates and water-dispersible isocyanates which can be used for this purpose.
  • Isocyanates for imparting felt to textiles have long been known and can be used, for example, as described in DE-OS 1.904.802, in organic solvents or, as described in DE-OS 1.769.121, in aqueous dispersion with the aid of emulsifiers. Both organic solvents and, if applicable, wastewater-polluting emulsifiers are no longer appropriate today for ecological and industrial hygiene reasons. In the following, therefore, we will either speak of self-dispersing isocyanates or of formulations which use as little as possible solvents and emulsifiers as auxiliaries and additives.
  • FR 1,542,831 describes the treatment of textile materials with baths, the polymers or copolymers of vinyl or divinyl compounds, an aqueous
  • DE-OS 4.415.451 (WO 95/30045) describes a process in which water-dispersible isocyanates are used for the finishing of wool without felt.
  • the examples describe that there However, the process described is such that the wool is first subjected to a pretreatment by oxidizing agents, followed by a reduction treatment, before the water-dispersible isocyanates are used.
  • this pretreatment causes wastewater which must be neutralized and clarified in accordance with the regulations.
  • These isocyanates also have a only limited storage stability
  • the present invention does not cause any wastewater due to the pretreatment by low-pressure plasma and is ecologically positive. Surprisingly, it was found that oxidative and / or reducing pretreatment agents are not required and a very good felt-free finish on wool can be achieved if a low-pressure plasma treatment is carried out before the treatment with aqueous dispersed isocyanates
  • the present invention relates to felt-free finished wool, which is characterized in that colored or undyed wool sliver
  • Another object of the present invention is a method for felt-free removal of wool, which is characterized in that dyed or undyed WoUkammzug
  • the self-dispersing isocyanates are also an object of the invention, they have an isocyanate content of 1 to 25% by weight. calculated as NCO (molecular weight 42) and based on the total weight of the isocyanates, and can be obtained by reaction in any order from:
  • n a number from 3 to 70
  • X and Y are hydrogen or methyl with the proviso that in the case of methyl only one of the radicals X and Y is methyl and the other is hydrogen,
  • R 1 and R 2 independently of one another are straight-chain or branched Ci-Cg-alkyl or C j -C 6 -acyl, where R 1 can be acyl, R 2 can also be hydrogen and R 1 and R 2 together can represent tetramethylene, pentamethylene or hexamethylene, in which one or two methylene groups can be replaced by O and / or NH and / or one or two methylene groups can be substituted by methyl, and
  • Z represents O, S or NH
  • NCO-reactive compounds which contain anionic or cationic or potentially anionic or cationic groups
  • self-dispersing in the present context means that the mixtures in a concentration of up to 70% by weight, preferably up to 50
  • ahphatic and cycloaliphatic polyisocyanates which contain uretdione and / or isocyanurate and / or allophanate and / or biuret - and / or oxadiazine structures and which can be prepared in a manner known per se from ahphatic, cycloahphatic, araliphatic or aromatic diisocyanates.
  • 1,4-dnsocyanate butane, 1,6-dusocyanatohexane, 15-dnsocyanato are suitable.
  • the preferred uretdione, isocyanurate, allophanate, oxadiazine groups reaction products of these dnsocyanates are essentially from t ⁇ merem 1,6-dusocyanatohexane or l-isocyanato-3,3,5-t ⁇ methyl-5- ⁇ socyanatomethyl-cyclohexane and from the corresponding higher homologues, isocyanurate groups and optionally containing uretdione groups containing polvisocyanate mixtures with an NCO content of 19 to 24% by weight.
  • isocyanate group-containing polyisocyanates of the stated NCO content are used, as described by known, catalyzed trimerization of 1,6-diisocyanatohexane or l-isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane with isocyanurate formation and which preferably have an (average) NCO functionality of 3.2 to 4 , 2 have.
  • polyisocyanates are aliphatic or aromatic diisocyanates such as hexamethylene diisocyanate, tolylene diisocyanate, 1,5-diisocyanatonaphthalene, diphenylmethane diisocyanate and their higher homologues with uretdione, isocyanurate, allophanate and biuret groups.
  • polyalkylene oxide ether alcohols ether amines and / or ether thiols of the formula (I)
  • the polyalkylene oxide ether alcohols are preferred.
  • the polyalkylene oxide ether alcohols are mono- or polyvalent polyalkylene oxide ether alcohols containing on average 3 to 70, preferably 6 to 60 alkylene oxide units per molecule, as are known in a manner known per se by alkylation of suitable starter molecules. Any secondary amines or acid amides can be reacted as starter molecules to produce these polyalkylene oxide ether alcohols. Heterocyclic nitrogen compounds such as morpholine are also suitable for the alkoxylation reaction. Identical compounds can also be obtained by using morpholinoethanol as a starter for the
  • Ethoxylation reaction used.
  • Acylation products of ethanolamine such as acetylethanolamine, can also be used as starters.
  • Alkylene oxides suitable for the alkoxylation reaction are ethylene oxide and propylene oxide, which can be used individually or in any order or in a mixture in the alkoxylation reaction.
  • the polyalkylene oxide ether alcohols are either pure polyethylene oxide polyethers, pure polypropylene polyethers or mixed polyalkylene oxide polyethers which have at least one polyether sequence which have at least 3, generally 3 to 70, preferably 6 to 60 and particularly preferably 7 to 20 alkylene oxide units, and their
  • At least 60 mol%, preferably at least 70 mol%, of alkylene oxide units consist of ethylene oxide units.
  • Preferred such polyalkylene oxide polyether alcohols are monofunctional polyalkylene oxide polyethers started on an aliphatic, nitrogen-containing starter according to structure (I) and having a statistical average of 6 to 60 Contain ethylene oxide units
  • NCO-reactive compounds which contain anionic or cationic and / or potential anionic or cationic groups are
  • hydroxyl-functional or amino-functional compounds with ammonium ions which in a manner known per se by alkylation or pro- toning, as described in EP-A 0 582 166, can be obtained from the tertiary amino groups of the compounds i).
  • any mixtures of NCO-reactive groups if chemically useful, for example from groups i) and iv), for example obtainable by partial alkylation of tertiary amino groups, or for example from groups ii) and iv), can also be used according to the invention.
  • the unmodified polyisocyanates to be used according to the invention can also be used in combination with external ionic or nonionic emulsifiers.
  • emulsifiers are described, for example, in Methods of Organic Chemistry, Houben-Weyl, Vol. XIV / 1, Part 1, pages 190-208 Thieme-Verlag, Stuttgart (1961), in US Pat. No. 3,428,592 and EP-A 0 013 112.
  • the emulsifiers are used in an amount which ensures dispersibility.
  • the starting components can be reacted in any order with the exclusion of moisture, preferably without a solvent.
  • component (II) With increasing amount of component (II), a higher viscosity of the end product is achieved, so that in certain cases (if the viscosity rises sharply) a solvent can be added, which is preferably miscible with water, but is inert towards the polyisocyanate.
  • Suitable solvents of this type are: alkyl ether acetates, glycol diesters, toluene, carboxylic acid esters, acetone, methyl ethyl ketone, tetrahydrofuran and dimethylformamide.
  • reaction can be accelerated Reaction is in the temperature range up to 130 ° C, preferably in the range between
  • reaction is carried out by titration of the NCO content or by measuring the IR spectra and evaluating the NCO band at 2260-2275 cm ⁇ l is tracked and ended when the isocyanate content is not more than 0.1% by weight above the value which is achieved for a given stochimetry with complete conversion. As a rule, reaction times of less than 24 hours are sufficient.
  • the solvent-free synthesis of the invention is preferred polyisocyanates to be used
  • polyisocyanates obtained by reacting polyisocyanates I) with polyalkylene oxide polyether alcohols, amines and / or thiols II), the ratio of equivalents of the isocyanate-reactive groups of component II to the NCO groups of component I) 1 1 to Amounts to 1 1000,
  • the number of NCO-reactive equivalents, the polyether content, the NCO content and the NCO functionality should be adjusted by the person skilled in the art by appropriate weighing in such a way that the mixture obtained is suitable for the water dispersions. has the required composition, in particular the preferred ranges already mentioned apply.
  • the self-dispersible polyisocyanate mixtures are technically easy to handle and can be stored for many months if moisture is excluded. This stability is one
  • the self-dispersible polyisocyanate mixtures are preferably used without organic solvents. They are very easy to emulsify in water at temperatures up to 100 ° C.
  • the active substance content of the emulsion can be up to 70
  • emulsions with an active substance content of 1 to 50% by weight, which can then optionally be further diluted before the metering point.
  • Mixing units customary in technology (stirrers, mixers with a rotor-stator principle and e.g. high-pressure emulsifying machines) are suitable for emulsification.
  • the preferred self-dispersible polyisocyanates are self-emulsifying, ie they can be easily emulsified after being added to the water phase without the action of high shear forces.
  • a static mixer is usually sufficient.
  • the emulsions obtained have a processing time of up to 24 hours, which depends on the structure of the polyisocyanates to be used according to the invention, in particular on their content of basic N atoms.
  • Self-dispersing isocyanate 2 (according to the invention):
  • Self-dispersing isocyanate 3 (according to the invention):
  • the self-dispersing isocyanates 2 (according to the invention) and 5 (for comparison) were each produced in kg and filled into 11 small bottles with a volume of 100 ml. After determining an initial value, these bottles were made for both the isocyanate content and the
  • the storage stability was checked by measuring the isocyanate content and the viscosity on a weekly basis (the last two measurements were carried out every two weeks); falling NCO content and increasing viscosity are indications of side reactions in the stored samples.
  • Fresh bottles were always opened, so that the test could not be influenced by the penetration of atmospheric humidity when the bottle was opened and closed again. Samples that had already been tested were then discarded. The following table gives an overview of the values found:
  • Viscosity NCO content Viscosity NCO content

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Plasma & Fusion (AREA)
  • Physics & Mathematics (AREA)
  • Dispersion Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention concerne une laine à finissage sans feutre et un procédé permettant de la produire, par a) traitement préalable avec un plasma basse pression et b) un traitement ultérieur avec des dispersions aqueuses d'isocyanates autodispersants. L'invention concerne par ailleurs des isocyanates dispersibles dans l'eau à stabilité au stockage améliorée, qui s'utilisent à cet effet.
EP98946313A 1997-08-22 1998-08-11 Laine a finissage sans feutre et isocyanates autodispersants utilises a cet effet Withdrawn EP1005584A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE1997136542 DE19736542A1 (de) 1997-08-22 1997-08-22 Filzfrei ausgerüstete Wolle und selbstdispergierende Isocyanate hierfür
DE19736542 1997-08-22
PCT/EP1998/005076 WO1999010590A1 (fr) 1997-08-22 1998-08-11 Laine a finissage sans feutre et isocyanates autodispersants utilises a cet effet

Publications (1)

Publication Number Publication Date
EP1005584A1 true EP1005584A1 (fr) 2000-06-07

Family

ID=7839823

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98946313A Withdrawn EP1005584A1 (fr) 1997-08-22 1998-08-11 Laine a finissage sans feutre et isocyanates autodispersants utilises a cet effet

Country Status (5)

Country Link
EP (1) EP1005584A1 (fr)
JP (1) JP2001514341A (fr)
AU (1) AU730514B2 (fr)
DE (1) DE19736542A1 (fr)
WO (1) WO1999010590A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19858736A1 (de) * 1998-12-18 2000-06-29 Bayer Ag Filzfrei ausgerüstete Wolle und Verfahren zur Filzfreiausrüstung
DE19953969A1 (de) * 1999-11-10 2001-05-17 Bayer Ag Filzfrei ausgerüstete Wolle und Verfahren zur Filzfreiausrüstung
DE10060048A1 (de) 2000-12-01 2002-06-06 Bayer Ag Filzfrei ausgerüstete Wolle und Verfahren zur Filzfreiausrüstung
FR2834523B1 (fr) * 2002-01-04 2006-02-03 Protex Procede de fabrication d'un agent de traitement destine a ameliorer le pouvoir antistatique d'un support textile

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1316505A (fr) * 1960-10-12 1963-02-01 Bayer Ag Procédé de fabrication de produits d'addition à partir de polyisocyanates et de composés contenant de l'hydrogène réactif combiné à l'azote
US3746858A (en) * 1971-12-21 1973-07-17 Us Agriculture Shrinkproofing of wool by low temperature plasma treatment
DE2314512C3 (de) * 1973-03-23 1980-10-09 Bayer Ag, 5090 Leverkusen Thermoplastische, nichtionische, in Wasser despergierbare im wesentlichen lineare Polyurethanelastomere
JP3265330B2 (ja) * 1994-03-02 2002-03-11 艶金興業株式会社 羊毛布帛の防縮加工法
DE4415451A1 (de) * 1994-05-03 1995-11-09 Basf Ag Verwendung von hydrophil modifizierten Polyisocyanaten zur Veredlung von Textilmaterialien
JPH08188969A (ja) * 1994-12-28 1996-07-23 Unitika Ltd 獣毛系繊維布帛の加工方法
DE19616776C1 (de) * 1996-04-26 1997-09-18 Bayer Ag Verfahren zur Antifilz-Ausrüstung von Wollmaterial mit Hilfe einer Niedertemperatur-Plasmabehandlung

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9910590A1 *

Also Published As

Publication number Publication date
AU9341098A (en) 1999-03-16
WO1999010590A1 (fr) 1999-03-04
JP2001514341A (ja) 2001-09-11
DE19736542A1 (de) 1999-02-25
AU730514B2 (en) 2001-03-08

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