EP0436524B1 - Dispersions for preparing fibrous material - Google Patents
Dispersions for preparing fibrous material Download PDFInfo
- Publication number
- EP0436524B1 EP0436524B1 EP87904867A EP87904867A EP0436524B1 EP 0436524 B1 EP0436524 B1 EP 0436524B1 EP 87904867 A EP87904867 A EP 87904867A EP 87904867 A EP87904867 A EP 87904867A EP 0436524 B1 EP0436524 B1 EP 0436524B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- aqueous dispersion
- compound
- carbon atoms
- optionally
- compounds
- 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
Links
- 239000006185 dispersion Substances 0.000 title claims abstract description 51
- 239000002657 fibrous material Substances 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 229920001577 copolymer Polymers 0.000 claims abstract description 15
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 14
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- 229920000742 Cotton Polymers 0.000 claims abstract description 8
- 229920000642 polymer Polymers 0.000 claims abstract description 8
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 239000000178 monomer Substances 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 5
- 150000002830 nitrogen compounds Chemical group 0.000 claims description 5
- 239000004753 textile Substances 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 239000004744 fabric Substances 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000010148 water-pollination Effects 0.000 abstract 1
- -1 unsaturated alkyl radical Chemical class 0.000 description 14
- 239000000203 mixture Substances 0.000 description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 3
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 2
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical compound O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 description 2
- ASKIVFGGGGIGKH-UHFFFAOYSA-N 2,3-dihydroxypropyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(O)CO ASKIVFGGGGIGKH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- ACFCVXXZCDHCRO-UHFFFAOYSA-N 1-(2-heptadec-1-enyl-4,5-dihydroimidazol-1-yl)ethanol Chemical compound CCCCCCCCCCCCCCCC=CC1=NCCN1C(C)O ACFCVXXZCDHCRO-UHFFFAOYSA-N 0.000 description 1
- PUMIBBNWDCWIKR-UHFFFAOYSA-M 1-(octadecoxymethyl)pyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC[N+]1=CC=CC=C1 PUMIBBNWDCWIKR-UHFFFAOYSA-M 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000004665 cationic fabric softener Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 150000002193 fatty amides Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical class NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XAVCZNYPFYJSJJ-UHFFFAOYSA-N n-(pyridin-1-ium-1-ylmethyl)octadecanamide;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC(=O)NC[N+]1=CC=CC=C1 XAVCZNYPFYJSJJ-UHFFFAOYSA-N 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
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
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
-
- 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
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
- D06M13/352—Heterocyclic compounds having five-membered heterocyclic rings
-
- 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
-
- 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
- D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
- D06M15/29—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides containing a N-methylol group or an etherified N-methylol group; containing a N-aminomethylene group; containing a N-sulfidomethylene group
-
- 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
- D06M15/65—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing epoxy groups
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
Definitions
- Cationic fabric softeners are known. However, the effectiveness of these compounds is adversely affected by remaining residues of anionic detergents on textile material washed with them. According to the subject of US-A-4 179 382, this disadvantage is eliminated in that small amounts of certain polymeric cationic salts are used together with the cationic plasticizers.
- One possibility of combining the known plasticizing equipment with a hydrophilizing equipment is not mentioned in this document and is also not suggested.
- copolymers based on alkyl acrylates for finishing textiles has long been known (DE-B-1 119 609 and DE-C-1 209 989).
- the feel of the fiber materials treated with it is favorably influenced.
- By varying the monomers and their proportions in the copolymer it is also possible to have other effects such as reduced wet soiling.
- the object of this invention was therefore to find means which remedy this deficiency in the prior art.
- Claims 11 to 17 describe processes for producing the dispersions according to the invention.
- the use of the aqueous dispersions is claimed.
- At least one quaternary nitrogen compound with at least one long-chain alkyl radical is used as compound (1).
- These compounds are generally known and have as the long-chain alkyl radical at least one saturated and / or unsaturated alkyl radical having at least 12, in particular 16 to 22, carbon atoms.
- Examples include octadecyloxymethyl-pyridinium chloride and stearylamido-methyl-pyridinium chloride.
- quaternary compounds are particularly suitable as compounds (1) Imidazolinium derivatives and quaternary ammonium derivatives.
- the amounts of compounds (1) used range from 20 to 70 g, in particular 30 to 60 g, per 1000 g of aqueous dispersion.
- the known polymers or copolymers based on alkyl acrylates with alkyl radicals having at least 4 C atoms are used as compounds (2).
- the alkyl radicals in these compounds (2) preferably have 4 to 10, in particular 4 to 8, carbon atoms.
- the following may be mentioned as examples of such base monomers, which are contained in the same in amounts of 60 to 100% by weight, based on the total polymer: 2-ethylhexyl acrylate, Decyl acrylate and above all Butyl acrylate.
- Homopolymers of butyl acrylate are particularly suitable as compounds (2), while ethyl acrylate cannot be used as the base monomer.
- copolymers based on the corresponding monomers can also be used as compounds (2).
- These compounds (2) are commercially available in the form of 30 to 70% strength aqueous dispersions, 20 to 80 g, in particular 20 to 60 g, compounds (2), calculated as 100% polymer, being used to prepare the aqueous dispersions according to the invention reach.
- emulsifier (3) can be up to 100% by weight, based on compound (2).
- the aqueous dispersion additionally contains at least one hydrophilizing silicone, in amounts of 5 to 70 g, in particular 15 to 55 g per 1000 g aqueous dispersion.
- These additionally used compounds (4) are also known to the person skilled in the art. In general, these are dimethylpolysiloxanes which contain epoxy groups (a) and / or polyethoxy or polypropoxy or polyethoxy / propoxy groups (b) incorporated.
- Silicones which have groups (a) and (b) in the same molecule are particularly suitable.
- a typical representative of the compounds (4) is UCARSIL® EPS (Union Carbide Corp.). Those skilled in the art will have no difficulty in finding similar useful compounds.
- the compounds (2) are prepared in the presence of the compounds (1) and, if appropriate, the compounds (4).
- the invention therefore furthermore relates to a process for the preparation of the aqueous dispersions according to the invention.
- the production of such dispersions is known in principle.
- a monomer emulsion is prepared which, in addition to the alkyl acrylates with alkyl radicals having at least 4 carbon atoms and optionally further comonomers and possibly the emulsifier (3), contains the quaternary compound with at least one long-chain alkyl radical and preferably also the compound (4).
- the actual polymerization is now carried out in a known manner.
- the aqueous dispersions obtained serve for the softening and hydrophilizing finishing of fiber materials of all kinds, in particular terry goods, especially cotton terry goods, but also of bed linen.
- the textiles are treated in a known manner with liquors which contain 15 to 80 g / l, in particular 20 to 60 g / l, of the aqueous dispersion, based on a dispersion with a solids content of about 20% by weight, so that a A coating of about 0.3 to 3% solid substance results on the fiber material.
- the hydrophilicity can be increased by brief post-condensation.
- a heavy cotton terry fabric (450 g / m2) is immersed in the liquor, squeezed to 110% liquor absorption and dried for 15 minutes at 120 o C equipped (solid support approx. 1%).
- the finished material has the following effects: The above results make it clear that only through the aqueous dispersions according to the invention are simultaneously obtained with a soft, pleasant feel and good to very good hydrophilicity.
- Example 1 is repeated in the same way, but using compound (1 d) as the quaternary compound having at least one long-chain alkyl radical.
- the cotton terry finished with the aqueous liquors prepared in accordance with Example 1 now shows the following effects:
- an aqueous dispersion is prepared in this example using the compound (1 e) corresponding to B), in addition, 50 parts of glycerol monoisostearate are melted at the beginning and the amount of hot water is increased to 740 parts.
- the cotton toweling finished with this dispersion B) also has a soft, fluffy feel and good to very good hydrophilicity.
- a light cotton terry towel (240 g / m2) is finished by immersing it in the liquor, squeezing to 100% liquor absorption and drying at 120 ° C. for 10 minutes.
- the goods treated in this way show a very soft, fluffy feel and is also characterized by a particularly good hydrophilicity.
- Example 3 is repeated, but the absence of the acetate of an ethoxylated C-16 fatty amine used there (on average 10 ethylene oxide groups).
- aqueous dispersion produced in this way is somewhat more difficult to filter, but can also be used very well to equip a wide variety of terry goods.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Inorganic Fibers (AREA)
- Paper (AREA)
- Colloid Chemistry (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
Description
Die vorliegende Erfindung betrifft wäßrige Dispersionen zur gleichzeitigen weichmachenden und hydrophilisierenden Ausrüstung von Fasermaterialien, die mindestens eine quaternäre Stickstoff-Verbindung mit mindestens einem gesättigten und/oder ungesättigten Alkylrest mit mindestens 12 C-Atomen und ein Polymerisat bzw. Copolymerisat auf Basis von Alkylacrylaten mit Alkylresten mit mindestens 4 C-Atomen enthalten, ein Verfahren zu deren Herstellung und deren Verwendung. Hierbei ist das genannte Polymerisat bzw. Copolymerisat in Gegenwart der quaternären Stickstoff-Verbindung hergestellt worden.The present invention relates to aqueous dispersions for the simultaneous softening and hydrophilizing finishing of fiber materials which contain at least one quaternary nitrogen compound with at least one saturated and / or unsaturated alkyl radical with at least 12 carbon atoms and a polymer or copolymer based on alkyl acrylates with alkyl radicals contain at least 4 carbon atoms, a process for their preparation and their use. The polymer or copolymer mentioned has been prepared in the presence of the quaternary nitrogen compound.
Kationische Textilweichmacher sind bekannt. Diese Verbindungen werden aber in ihrer Wirkung durch verbleibende Reste an anionischen Detergentien auf damit gewaschenem Textilmaterial ungünstig beeinflußt. Nach dem Gegenstand der US-A-4 179 382 wird dieser Nachteil dadurch beseitigt, daß geringe Mengen an bestimmten polymeren kationischen Salzen zusammen mit den kationischen Weichmachern eingesetzt werden. Eine Möglichkeit, die bekannte weichmachende Ausrüstung mit einer hydrophilisierenden Ausrüstung zu kombinieren, wird in dieser Druckschrift nicht erwähnt und auch nicht nahegelegt.Cationic fabric softeners are known. However, the effectiveness of these compounds is adversely affected by remaining residues of anionic detergents on textile material washed with them. According to the subject of US-A-4 179 382, this disadvantage is eliminated in that small amounts of certain polymeric cationic salts are used together with the cationic plasticizers. One possibility of combining the known plasticizing equipment with a hydrophilizing equipment is not mentioned in this document and is also not suggested.
Außerdem ist die Verwendung von Copolymeren auf Basis von Alkylacrylaten zur Ausrüstung von Textilien längst bekannt (DE-B-1 119 609 und DE-C-1 209 989). Der Griff der damit behandelten Fasermaterialien wird günstig beeinflußt. Auch ist es durch Variation der Monomeren und deren Mengenverhältnisse im Copolymerisat durchaus möglich, andere Effekte wie z.B. eine verringerte Naßanschmutzung, zu erhalten.In addition, the use of copolymers based on alkyl acrylates for finishing textiles has long been known (DE-B-1 119 609 and DE-C-1 209 989). The feel of the fiber materials treated with it is favorably influenced. By varying the monomers and their proportions in the copolymer it is also possible to have other effects such as reduced wet soiling.
Der Stand der Technik hat aber bis heute noch keinen Weg aufgezeigt, auf dieser Basis gleichzeitig einen angenehmen weichen, flauschigen Griff und eine verbesserte Hydrophilität der ausgerüsteten Fasermaterialien, insbesondere von Baumwoll-Frottee-Waren, zu erzielen.To date, however, the prior art has not shown any way of simultaneously achieving a pleasant soft, fluffy feel and improved hydrophilicity of the finished fiber materials, in particular cotton terry goods, on this basis.
Aufgabe dieser Erfindung war es deshalb, Mittel aufzufinden, die diesen Mangel des Standes der Technik beheben.The object of this invention was therefore to find means which remedy this deficiency in the prior art.
Erfindungsgemäß gelingt es nunmehr, wäßrige Dispersionen bereitzustellen, die gleichzeitig eine weichmachende und hydrophilisierende Ausrüstung von Fasermaterialien bewirken, wenn die im Patentanspruch 1 näher beschriebenen Bedingungen eingehalten werden. In den Unteransprüchen 2 bis 10 werden detaillierte Einzelheiten der wäßrigen Dispersionen unter Schutz gestellt.According to the invention, it is now possible to provide aqueous dispersions which at the same time bring about a softening and hydrophilizing finish on fiber materials if the conditions described in more detail in claim 1 are observed. In sub-claims 2 to 10 detailed details of the aqueous dispersions are protected.
Die Patentansprüche 11 bis 17 beschreiben Verfahren zur Herstellung der erfindungsgemäßen Dispersionen. Im Patentanspruch 18 wird die Verwendung der wäßrigen Dispersionen beansprucht.Claims 11 to 17 describe processes for producing the dispersions according to the invention. In claim 18, the use of the aqueous dispersions is claimed.
Als Verbindung (1) wird mindestens eine quaternäre Stickstoff-Verbindung mit mindestens einem langkettigen Alkylrest eingesetzt. Diese Verbindungen sind allgemein bekannt und haben als langkettigen Alkylrest mindestens einen gesättigten und/oder ungesättigten Alkylrest mit mindestens 12, insbesondere 16 bis 22 C-Atomen.At least one quaternary nitrogen compound with at least one long-chain alkyl radical is used as compound (1). These compounds are generally known and have as the long-chain alkyl radical at least one saturated and / or unsaturated alkyl radical having at least 12, in particular 16 to 22, carbon atoms.
Als Beispiele seien Octadecyloxymethyl-Pyridiniumchlorid und Stearylamido-methyl-pyridiniumchlorid genannt. Besonders geeignet sind aber als Verbindungen (1) quaternäre Imidazoliniumderivate und quaternäre Ammoniumderivate. Für die besonders geeigneten Verbindungen seien als Beispiele nachfolgende aufgeführt:
1-Stearinsäureamidoethyl-2-stearyl-3-methyl-imidazoliniummethosulfat (Verbindung 1 a),
1-Methyl-2-Talgfettsäureamido-ethylimidazoliniummethosulfat (Verbindung 1 b),
1-Hydroxyethyl-2-heptadecenyl-imidazolinium-ethosulfat (Verbindung 1 c),
Dimethyl-distearyl-ammoniumchlorid (Verbindung 1 d) und
Diölsäureisopropylester-dimethyl-ammonium-ethosulfat (Verbindung 1 e).Examples include octadecyloxymethyl-pyridinium chloride and stearylamido-methyl-pyridinium chloride. However, quaternary compounds are particularly suitable as compounds (1) Imidazolinium derivatives and quaternary ammonium derivatives. The following are examples of the particularly suitable compounds:
1-stearic acid amidoethyl-2-stearyl-3-methyl-imidazolinium methosulfate (compound 1 a),
1-methyl-2-tallow fatty acid amido-ethyl imidazolinium methosulfate (compound 1 b),
1-hydroxyethyl-2-heptadecenyl imidazolinium ethosulfate (compound 1 c),
Dimethyl-distearyl-ammonium chloride (compound 1 d) and
Isopropyl diolate dimethyl ammonium ethosulfate (Compound 1 e).
Die verwendeten Mengen an Verbindungen (1) bewegen sich von 20 bis 70 g, insbesondere 30 bis 60 g auf 1000 g wäßrige Dispersion.The amounts of compounds (1) used range from 20 to 70 g, in particular 30 to 60 g, per 1000 g of aqueous dispersion.
Als Verbindungen (2) kommen die bekannten Polymerisate bzw. Copolymerisate auf Basis von Alkylacrylaten mit Alkylresten mit mindestens 4 C-Atomen zur Anwendung. Die Alkylreste in diesen Verbindungen (2) weisen dabei vorzugsweise 4 bis 10, insbesondere 4 bis 8 C-Atome auf. Als Beispiele für derartige Basismonomere, die in Mengen von 60 bis 100 Gew.%, bezogen auf das gesamte Polymerisat, in demselben enthalten sind, seien folgende genannt:
2-Ethylhexylacrylat,
Decylacrylat und vor allem
Butylacrylat.The known polymers or copolymers based on alkyl acrylates with alkyl radicals having at least 4 C atoms are used as compounds (2). The alkyl radicals in these compounds (2) preferably have 4 to 10, in particular 4 to 8, carbon atoms. The following may be mentioned as examples of such base monomers, which are contained in the same in amounts of 60 to 100% by weight, based on the total polymer:
2-ethylhexyl acrylate,
Decyl acrylate and above all
Butyl acrylate.
Homopolymere von Butylacrylat sind besonders gut als Verbindungen (2) geeignet, während Ethylacrylat als Basismonomer nicht verwendbar ist. Neben den Alkylacrylathomopolymeren sind als Verbindungen (2) auch auf den entsprechenden Monomeren basierende Copolymerisate verwendbar.Homopolymers of butyl acrylate are particularly suitable as compounds (2), while ethyl acrylate cannot be used as the base monomer. In addition to the alkyl acrylate homopolymers, copolymers based on the corresponding monomers can also be used as compounds (2).
Als Comonomere seien ohne Anspruch auf Vollständigkeit folgende genannt (jeweils bezogen auf Summe der Monomeren):
2-Hydroxyethyl- bzw. 3-Hydroxypropyl-(meth)acrylat (2 bis 10 Gew.%), Alkylmethacrylate mit mindestens 4 C-Atomen im Alkylrest (2 bis 20 Gew.%), Ethylacrylat (1 bis 40 Gew.%), (Meth)acrylsäure (1 bis 5 Gew.%), Amide oder N-Methylolamide bzw. mit Alkoholen mit 1 bis 4 C-Atomen veretherte Methylolamide α ,β-ungesättigter Carbonsäuren oder Gemische solcher Monomeren (0,5 bis 5 Gew.%), Vinylacetat (2 bis 40 Gew.%) und Acrylnitril (1 bis 10 Gew.%).The following may be mentioned as comonomers without any claim to completeness (in each case based on the sum of the monomers):
2-hydroxyethyl or 3-hydroxypropyl (meth) acrylate (2 to 10% by weight), alkyl methacrylates with at least 4 carbon atoms in the alkyl radical (2 to 20% by weight), ethyl acrylate (1 to 40% by weight) , (Meth) acrylic acid (1 to 5 wt.%), Amides or N-methylolamides or methylolamides α, β-unsaturated carboxylic acids etherified with alcohols with 1 to 4 carbon atoms or mixtures of such monomers (0.5 to 5 wt. %), Vinyl acetate (2 to 40% by weight) and acrylonitrile (1 to 10% by weight).
Diese Verbindungen (2) kommen in Form 30 bis 70%iger wäßriger Dispersionen in den Handel, wobei zur Herstellung der erfindungsgemäßen wäßrigen Dispersionen 20 bis 80 g, insbesondere 20 bis 60 g Verbindungen (2), gerechnet als 100%iges Polymerisat, zur Anwendung gelangen.These compounds (2) are commercially available in the form of 30 to 70% strength aqueous dispersions, 20 to 80 g, in particular 20 to 60 g, compounds (2), calculated as 100% polymer, being used to prepare the aqueous dispersions according to the invention reach.
Von Fall zu Fall, vor allem wenn relativ geringe Mengen an Verbindungen (1) zum Einsatz gelangen oder wenn erhöhte Anforderungen an die Verträglichkeit mit optischen Aufhellern gestellt werden, ist es notwendig, neben den Verbindungen (1) noch einen zusätzlichen Emulgator bei der Herstellung der wäßrigen Dispersionen einzusetzen.
Als Emulgatoren werden dabei die bekannten nicht-ionogenen und/oder von (1) verschiedenen kationaktiven Emulgatoren (3) verwendet.From case to case, especially if relatively small amounts of compounds (1) are used or if increased demands are placed on compatibility with optical brighteners, it is necessary to add an additional emulsifier in addition to the compounds (1) in the preparation of the to use aqueous dispersions.
The known nonionic and / or cationic emulsifiers (3) which are different from (1) are used as emulsifiers.
Der Fachmann kennt die ethoxylierten Fettalkohole, Fettamide, Fettsäuren, Alkylphenole und Fettamine bzw. deren Salze oder die verwendeten z.B. quaternären Ammoniumverbindungen und wird keine Schwierigkeiten haben, diese Verbindungen entsprechend auszuwählen. Die Mengen an Emulgator (3) können bis zu 100 Gew.%, bezogen auf Verbindung (2), betragen.The person skilled in the art knows the ethoxylated fatty alcohols, fatty amides, fatty acids, alkylphenols and fatty amines or their salts or the e.g. quaternary ammonium compounds and will have no difficulty in selecting these compounds accordingly. The amounts of emulsifier (3) can be up to 100% by weight, based on compound (2).
Ein besonders angenehmer und weicher Griff der behandelten Fasermaterialien und vor allem eine merklich gesteigerte Hydrophilität wird dann erhalten, wenn die wäßrige Dispersion zusätzlich mindestens ein hydrophilisierend wirkendes Silikon enthält, und zwar in Mengen von 5 bis 70 g, insbesondere 15 bis 55 g auf 1000 g wäßrige Dispersion. Diese zusätzlich verwendeten Verbindungen (4) sind dem Fachmann ebenfalls bekannt. Im allgemeinen handelt es sich um Dimethylpolysiloxane, die Epoxygruppen (a) und/oder Polyethoxy- bzw. Polypropoxy- bzw. Polyethoxy/Propoxy-Gruppen (b) eingebaut enthalten.A particularly pleasant and soft feel of the treated fiber materials and, above all, a noticeably increased hydrophilicity is obtained if the aqueous dispersion additionally contains at least one hydrophilizing silicone, in amounts of 5 to 70 g, in particular 15 to 55 g per 1000 g aqueous dispersion. These additionally used compounds (4) are also known to the person skilled in the art. In general, these are dimethylpolysiloxanes which contain epoxy groups (a) and / or polyethoxy or polypropoxy or polyethoxy / propoxy groups (b) incorporated.
Besonders geeignet sind solche Silikone, die im gleichen Molekül die Gruppen (a) und (b) aufweisen. Ein typischer Vertreter für die Verbindungen (4) ist UCARSIL® EPS (Union Carbide Corp.). Der Fachmann wird keine Schwierigkeiten haben, ähnliche verwendbare Verbindungen aufzufinden.Silicones which have groups (a) and (b) in the same molecule are particularly suitable. A typical representative of the compounds (4) is UCARSIL® EPS (Union Carbide Corp.). Those skilled in the art will have no difficulty in finding similar useful compounds.
Entscheidend für die Wirksamkeit der erfindungsgemäßen, wäßrigen Dispersionen ist, daß die Herstellung der Verbindungen (2) in Gegenwart der Verbindungen (1) und gegebenenfalls der Verbindungen (4) erfolgt. Gegenstand der Erfindung ist deshalb weiterhin ein Verfahren zur Herstellung der erfindungsgemäßen wäßrigen Dispersionen. Grundsätzlich ist die Herstellung solcher Dispersionen bekannt. Im allgemeinen wird eine Monomerenemulsion bereitet, die neben den Alkylacrylaten mit Alkylresten mit mindestens 4 C-Atomen und gegebenenfalls weiteren Comonomeren und eventuell dem Emulgator (3) die quaternäre Verbindung mit mindestens einem langkettigen Alkylrest und bevorzugt auch die Verbindung (4) enthält.
Die eigentliche Polymerisation wird nun in bekannter Weise vorgenommen. Selbstverständlich können der Monomeremulsion und/oder der fertigen wäßrigen Dispersion noch weitere bekannte Textilhilfsmittel, insbesondere Weichmacher und/oder griffgebende Substanzen in geringer Menge zugesetzt werden, um die Eigenschaften der wäßrigen Dispersion abzurunden.It is crucial for the effectiveness of the aqueous dispersions according to the invention that the compounds (2) are prepared in the presence of the compounds (1) and, if appropriate, the compounds (4). The invention therefore furthermore relates to a process for the preparation of the aqueous dispersions according to the invention. The production of such dispersions is known in principle. Generally a monomer emulsion is prepared which, in addition to the alkyl acrylates with alkyl radicals having at least 4 carbon atoms and optionally further comonomers and possibly the emulsifier (3), contains the quaternary compound with at least one long-chain alkyl radical and preferably also the compound (4).
The actual polymerization is now carried out in a known manner. Of course, other known textile auxiliaries, in particular plasticizers and / or substances which give grip, can be added to the monomer emulsion and / or the finished aqueous dispersion in small amounts in order to round off the properties of the aqueous dispersion.
Die erhaltenen wäßrigen Dispersionen dienen zur weichmachenden und hydrophilisierenden Ausrüstung von Fasermaterialien aller Art, insbesondere von Frottee-Waren, vor allem Baumwoll-Frottee-Waren, aber auch von Bettwäsche.The aqueous dispersions obtained serve for the softening and hydrophilizing finishing of fiber materials of all kinds, in particular terry goods, especially cotton terry goods, but also of bed linen.
Dazu werden die Textilien mit Flotten, die 15 bis 80 g/l, insbesondere 20 bis 60 g/l der wäßrigen Dispersion, bezogen auf eine Dispersion mit einem Feststoffgehalt von ca. 20 Gew.%, enthalten, in bekannter Weise behandelt, wodurch eine Auflage von etwa 0,3 bis 3 % Festsubstanz auf dem Fasermaterial resultiert. Durch kurze Nachkondensation kann dabei die Hydrophilität noch gesteigert werden.To this end, the textiles are treated in a known manner with liquors which contain 15 to 80 g / l, in particular 20 to 60 g / l, of the aqueous dispersion, based on a dispersion with a solids content of about 20% by weight, so that a A coating of about 0.3 to 3% solid substance results on the fiber material. The hydrophilicity can be increased by brief post-condensation.
Es ist überraschend, daß es auf diese einfache Art und Weise gelingt, einen weichen, flauschigen Griff und gleichzeitig eine gute bis hervorragende Hydrophilität der ausgerüsteten Materialien zu erhalten, nachdem durch einfaches Mischen der Verbindungen (1) und (2) (siehe auch nachfolgende Beispiele) ein solcher Kombinationseffekt nicht erreichbar ist.It is surprising that it is possible in this simple manner to obtain a soft, fluffy feel and at the same time a good to excellent hydrophilicity of the finished materials, after simply mixing the compounds (1) and (2) (see also the examples below ) such a combination effect cannot be achieved.
Die Erfindung wird durch die nachfolgenden Beispiele näher beschrieben, wobei Teile = Gewichtsteile und % = Gewichtsprozent sind.The invention is described in more detail by the following examples, parts = parts by weight and% = percent by weight.
-
A) Eine Voremulsion wird durch Vorlegen und Aufschmelzen bei 80 bis 90oC aus 37,5 Teilen 1-Methyl-2-Talgfettsäureamido-ethyl-imidazolinmethosulfat und 20 Teilen des Acetats eines ethoxylierten C-16-Fettamins (insgesamt 10 EO-Gruppen je Mol) als zusätzlicher Emulgator und nachfolgender Zugabe von 550 Teilen 90oC heißem Wasser, abkühlen auf 40oC und weiterer Zugabe von 2,5 Teilen Phosphorsäure (pH 5 bis 6), 60 Teilen Butylacrylat und 45 Teilen UCARSIL® EPS unter Rühren hergestellt.
Zur Polymerisation werden 100 Teile Wasser und 3 Teile des obengenannten Emulgators vorgelegt, mit 0,2 Teilen Phosphorsäure auf einen pH-Wert von 4 eingestellt und 100 Teile der wie oben beschrieben bereiteten Voremulsion zugegeben. Das Gemisch wird nunmehr auf 60oC erwärmt und mit 3 Teilen Natriumpersulfatlösung (25%ig) und 2 Teilen Rongalit C-Lösung (10%ig) geimpft. Unter Zulauf des restlichen Monomerengemisches erfolgt bei 65 bis 70oC die Polymerisation während 1 Stunde, wobei gleichzeitig kontinuierlich 3 Teile der Natriumpersulfatlösung und 8 Teile der® Rongalit C-Lösung (BASF) zugegeben werden. Anschließend werden nochmals 2 Teile Natriumpersulfatlösung und 2 Teile Rongalit C-Lösung nachgesetzt und der Ansatz 1 Stunde bei 65 bis 70oC nachgerührt.
Abschließend wird durch Zugabe eines Gemisches aus 0,5 g tert.-Butylhydroperoxid und 0,5 g des obengenannten Emulgators (50%ig in Wasser) der Restmonomergehalt auf unter 0,2 % gesenkt.
Bei 50oC wird danach mit 6 Teilen Triethanolamin auf einen pH-Wert von 6 bis 7 eingestellt und abschließend das Produkt in bekannter Weise filtriert. Es wird eine gut kältebeständige, stabile wäßrige Dispersion erhalten.A) A pre-emulsion is by charging and melting at 80 to 90 o C of 37.5 parts of 1-methyl-2-Talgfettsäureamido-ethyl-imidazolinmethosulfat and 20 parts of the acetate of ethoxylated C-16 fatty amine (a total of 10 EO groups per Mol) as an additional emulsifier and subsequent addition of 550 parts of 90 o C hot water, cooling to 40 o C and further addition of 2.5 parts of phosphoric acid (pH 5 to 6), 60 parts of butyl acrylate and 45 parts of UCARSIL® EPS with stirring .
For the polymerization, 100 parts of water and 3 parts of the above-mentioned emulsifier are introduced, adjusted to a pH of 4 with 0.2 part of phosphoric acid and 100 parts of the pre-emulsion prepared as described above are added. The mixture is now heated to 60 o C with 3 parts of sodium persulfate (25%) and 2 parts of Rongalit vaccinated C solution (10%). With addition of the remaining monomer mixture, the polymerization takes place at 65 to 70 ° C. for 1 hour, 3 parts of the sodium persulfate solution and 8 parts of the® Rongalit C solution (BASF) being added continuously at the same time. Subsequently, a further 2 parts of sodium persulfate and 2 parts of Rongalit are appended to C solution and the mixture stirred for 1 hour at 65 to 70 ° C.
Finally, by adding a mixture of 0.5 g of tert-butyl hydroperoxide and 0.5 g of the above-mentioned emulsifier (50% in water), the residual monomer content is below Reduced 0.2%.
At 50 ° C., the pH is then adjusted to 6 to 7 using 6 parts of triethanolamine, and the product is then filtered in a known manner. A good cold-resistant, stable aqueous dispersion is obtained. - B) Zur Herstellung der wäßrigen Dispersion B wird in gleicher Weise wie oben gearbeitet, wobei jedoch in Abwesenheit von UCARSIL® EPS polymerisiert wird.B) The aqueous dispersion B is prepared in the same manner as above, but polymerisation is carried out in the absence of UCARSIL® EPS.
- C) Wie Dispersion B), wobei aber 45 Teile UCARSIL® EPS abschließend kalt eingerührt werden.C) Like dispersion B), but 45 parts of UCARSIL® EPS are then stirred in cold.
- D) Zum Vergleich wird die unter A) beschriebene Arbeitsweise in gleicher Weise in Abwesenheit der Verbindung (1 b) und des UCARSIL® EPS durchgeführt. Dafür werden aber nach erfolgter Polymerisation 37,5 Teile der Verbindung (1 b) kalt eingerührt.D) For comparison, the procedure described under A) is carried out in the same way in the absence of the compound (1 b) and the UCARSIL® EPS. However, 37.5 parts of compound (1 b) are stirred in cold after the polymerization.
Mit 40 g/l der wie oben beschrieben hergestellten wäßrigen Dispersionen A) bis D) wird eine schwere Baumwoll-Frottee-Ware (450 g/m²) durch Eintauchen in die Flotte, Abquetschen auf 110 % Flottenaufnahme und Trocknen während 15 Minuten bei 120oC ausgerüstet (Feststoffauflage ca. 1 %).With 40 g / l of the aqueous dispersions A) to D) prepared as described above, a heavy cotton terry fabric (450 g / m²) is immersed in the liquor, squeezed to 110% liquor absorption and dried for 15 minutes at 120 o C equipped (solid support approx. 1%).
Das ausgerüstete Material weist folgende Effekte auf:
Die vorstehenden Ergebnisse machen deutlich, daß nur durch die erfindungsgemäßen wäßrigen Dispersionen gleichzeitig ein weicher, angenehmer Griff und eine gute bis sehr gute Hydrophilität erhalten werden.The finished material has the following effects:
The above results make it clear that only through the aqueous dispersions according to the invention are simultaneously obtained with a soft, pleasant feel and good to very good hydrophilicity.
Das Beispiel 1 wird in gleicher Weise wiederholt, wobei aber als quaternäre Verbindung mit mindestens einem langkettigen Alkylrest die Verbindung (1 d) zum Einsatz kommt. Der mit den entsprechend Beispiel 1 hergestellten wäßrigen Flotten ausgerüstete Baumwoll-Frottee zeigt nunmehr folgende Effekte:
Anstelle der in Beispiel 1 verwendeten Verbindung (1 b) wird in diesem Beispiel unter Verwendung der Verbindung (1 e) entsprechend B) eine wäßrige Dispersion hergestellt, wobei zusätzlich gleich zu Beginn 50 Teile Glycerinmonoisostearat mit aufgeschmolzen werden und dafür die Heißwassermenge auf 740 Teile erhöht wird. Die mit dieser Dispersion B) ausgerüstete Baumwoll-Frottee-Ware weist ebenfalls einen weichen, flauschigen Griff und eine gute bis sehr gute Hydrophilität auf.Instead of the compound (1 b) used in Example 1, an aqueous dispersion is prepared in this example using the compound (1 e) corresponding to B), in addition, 50 parts of glycerol monoisostearate are melted at the beginning and the amount of hot water is increased to 740 parts. The cotton toweling finished with this dispersion B) also has a soft, fluffy feel and good to very good hydrophilicity.
In gleicher Weise wie im Beispiel 1 beschrieben wird unter Verwendung von 40 g eines Emulgator-Gemisches aus
- 250 Teilen
- Ricinolsäurepolyglykolester (durchschnittlich 12 Ethylenoxideinheiten),
- 200 Teilen
- Stearylaminethoxylat (durchschnittlich 8 Ethylenoxideinheiten) und
- 6 Teilen
- Eisessig
- 40 Teilen
- Butylacrylat,
- 10 Teilen
- 2-Ethylhexylacrylat und
- 10 Teilen
- Vinylacetat
- 250 pieces
- Ricinoleic acid polyglycol ester (on average 12 ethylene oxide units),
- 200 parts
- Stearylamine ethoxylate (8 ethylene oxide units on average) and
- 6 parts
- Glacial acetic acid
- 40 parts
- Butyl acrylate,
- 10 parts
- 2-ethylhexyl acrylate and
- 10 parts
- Vinyl acetate
Unter Verwendung von 35 g/l dieser wäßrigen Dispersion wird eine leichte Baumwoll-Frottee-Handtuchware (240 g/m²) durch Eintauchen in die Flotte, Abquetschen auf 100 % Flottenaufnahme und Trocknen während 10 Minuten bei 120oC ausgerüstet. Die so behandelte Ware zeigt einen sehr weichen, flauschigen Griff und ist auch durch eine besonders gute Hydrophilität charakterisiert.Using 35 g / l of this aqueous dispersion, a light cotton terry towel (240 g / m²) is finished by immersing it in the liquor, squeezing to 100% liquor absorption and drying at 120 ° C. for 10 minutes. The goods treated in this way show a very soft, fluffy feel and is also characterized by a particularly good hydrophilicity.
In gleicher Weise wie im Beispiel 4 wird unter Verwendung des nachfolgend genannten Monomergemisches eine Monomeremulsion hergestellt und dann wie beschrieben, die wäßrige Dispersion bereitet:
- 40 Teile
- Butylacrylat,
- 5 Teile
- n-Decylacrylat,
- 8 Teile
- Acrylnitril und
- 2 Teile
- N-Methylolacrylamid.
- 40 parts
- Butyl acrylate,
- 5 parts
- n-decyl acrylate,
- 8 parts
- Acrylonitrile and
- 2 parts
- N-methylol acrylamide.
Wird die in Beispiel 4 beschriebene Frottee-Ware in gleicher Weise unter Verwendung von 50 g/l dieser Dispersion ausgerüstet, so werden ähnlich gute Effekte erhalten.If the terry cloth described in Example 4 is finished in the same way using 50 g / l of this dispersion, similarly good effects are obtained.
Das Beispiel 3 wird wiederholt, wobei aber in Abwesenheit des dort verwendeten Acetats eines ethoxylierten C-16-Fettamins (durchschnittlich 10 Ethylenoxidgruppen) gearbeitet wird.Example 3 is repeated, but the absence of the acetate of an ethoxylated C-16 fatty amine used there (on average 10 ethylene oxide groups).
Die dabei hergestellte wäßrige Dispersion ist etwas schlechter filtrierbar, kann aber ebenfalls sehr gut zur Ausrüstung der verschiedensten Frottee-Waren herangezogen werden.The aqueous dispersion produced in this way is somewhat more difficult to filter, but can also be used very well to equip a wide variety of terry goods.
Claims (18)
- Aqueous dispersion for the simultaneous softening and hydrophilising of fibre materials, comprising(1) at least one quaternary nitrogen compound having at least one saturated and/or unsaturated alkyl radical of at least 12 carbon atoms,(2) a polymer or copolymer based on alkyl acrylates having alkyl radicals of at least 4 carbon atoms prepared in the presence of compound (1),(3) optionally additionally an emulsifier which differs from (1), and(4) optionally a hydrophilising silicone.
- Aqueous dispersion according to Claim 1, characterised in that compound (1) comprises quaternary compounds having at least one saturated and/or unsaturated alkyl radical of 16 to 22 carbon atoms.
- Aqueous dispersion according to Claims 1 and 2, characterised in that compound (1) comprises quaternary imidazolinium derivatives.
- Aqueous dispersion according to Claims 1 and 2, characterised in that compounds (1) are quaternary ammonium derivatives.
- Aqueous dispersion according to Claims 1 to 4, characterised in that the handle-forming (co)polymer (2) is based on alkyl acrylates having alkyl radicals of 4 to 10, in particular 4 to 8, carbon atoms as base monomer.
- Aqueous dispersion according to Claims 1 to 5, characterised in that 20 to 70 g of compound (1), 20 to 80 g of compound (2) and optionally up to 100% by weight, based on compound (2) of emulsifier (3) are contained per 1000 g of aqueous dispersion.
- Aqueous dispersion according to Claims 1 to 6, characterised in that compound (4) comprises at least one hydrophilising dimethylpolysiloxane.
- Aqueous dispersion according to Claim 7, characterised in that compound (4) contains epoxy groups and/or polyethoxy or polypropoxy or polyethoxy/propoxy groups.
- Aqueous dispersion according to Claims 7 and 8, characterised in that 5 to 70 g of compound (4) are contained per 1000 g of aqueous dispersion.
- Aqueous dispersion according to Claims 1 to 9, characterised in that it also contains customary textile auxiliaries.
- Process for preparing aqueous dispersions according to Claims 1 to 10, characterised in that polymers or copolymers (2) based on alkyl acrylates having alkyl radicals of at least 4 carbon atoms are prepared in the presence of at least one quaternary nitrogen compound having at least one saturated and/or unsaturated alkyl radical of at least 12 carbon atoms (1), optionally a customary non-ionic and/or cationic emulsifier (3) different from (1) and optionally at least one hydrophilising silicone (4) in a conventional manner.
- Process according to Claim 11, characterised in that the (co)polymers (2) are prepared in the presence of quaternary compounds having at least one saturated and/or unsaturated alkyl radical of 16 to 22 carbon atoms.
- Process according to Claims 11 and 12, characterised in that the (co)polymers (2) are prepared in the presence of quaternary imidazolinium derivatives as compound (1).
- Process according to Claims 11 and 12, characterised in that the (co)polymers (2) are prepared in the presence of quaternary ammonium derivatives as compound (1).
- Process according to Claims 11 to 14, characterised in that the (co)polymers (2) are prepared using alkyl acrylates having alkyl radicals of 4 to 10, in particular 4 to 8, carbon atoms as base monomers.
- Process according to Claims 11 to 15, characterised in that the (co)polymers (2) are prepared in the presence of 20 to 70 g of compounds (1), optionally up to 100% by weight, based on compounds (2), of emulsifiers (3) and optionally 5 to 70 g of compounds (4), each amount being based on 1000 g of aqueous dispersion, by polymerisation of 20 to 80 g of monomers, the base monomers used being alkyl acrylates having alkyl radicals of 4 to 10, in particular 4 to 8, carbon atoms.
- Process according to Claims 11 to 16, characterised in that the comonomers used comprise vinyl acetate, acrylonitrile, N-methylolacrylamide, optionally etherified with alcohols of 1 to 4 carbon atoms, in amounts of 0.5 to 40% by weight, based on the sum total of the polymerisable monomers used.
- Use of the aqueous dispersion according to Claims 1 to 10 for the softening and hydrophilic finishing of terry cotton.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT87904867T ATE82337T1 (en) | 1986-08-01 | 1987-07-18 | DISPERSIONS FOR FINISHING FIBER MATERIALS. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863626051 DE3626051A1 (en) | 1986-08-01 | 1986-08-01 | AQUEOUS DISPERSIONS FOR THE SIMULTANEOUS SOFTENING AND HYDROPHILIZING EQUIPMENT OF FIBER MATERIALS, METHOD FOR THEIR PRODUCTION AND THEIR USE |
| DE3626051 | 1986-08-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0436524A1 EP0436524A1 (en) | 1991-07-17 |
| EP0436524B1 true EP0436524B1 (en) | 1992-11-11 |
Family
ID=6306476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP87904867A Expired - Lifetime EP0436524B1 (en) | 1986-08-01 | 1987-07-18 | Dispersions for preparing fibrous material |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4966725A (en) |
| EP (1) | EP0436524B1 (en) |
| JP (1) | JPH01503791A (en) |
| AT (1) | ATE82337T1 (en) |
| AU (1) | AU616157B2 (en) |
| DE (2) | DE3626051A1 (en) |
| PT (1) | PT85462B (en) |
| WO (1) | WO1988000991A2 (en) |
| ZA (1) | ZA875678B (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8811955D0 (en) * | 1988-05-20 | 1988-06-22 | Allied Colloids Ltd | Absorbent products & their manufacture |
| DE3939549A1 (en) * | 1989-11-30 | 1991-06-06 | Henkel Kgaa | Lubricant for textiles, partic. for thread during high speed mfr. - or processing contains alkyl acrylate or methacrylate homo-polymer or copolymer of specified min. limiting viscosity |
| JPH04119174A (en) * | 1990-09-10 | 1992-04-20 | Toray Dow Corning Silicone Co Ltd | Textile-treatment agent |
| US5407728A (en) | 1992-01-30 | 1995-04-18 | Reeves Brothers, Inc. | Fabric containing graft polymer thereon |
| US5486210A (en) | 1992-01-30 | 1996-01-23 | Reeves Brothers, Inc. | Air bag fabric containing graft polymer thereon |
| DE4313085A1 (en) * | 1993-04-21 | 1994-10-27 | Stockhausen Chem Fab Gmbh | Stable aqueous dispersions of quaternary ammonium compounds and imidazoline derivatives |
| US5408012A (en) * | 1993-05-27 | 1995-04-18 | Comfort Technologies, Inc. | Polymers having enhanced durable hydrophilicity and durable rewetting properties and process of producing the same |
| DE4331642C1 (en) * | 1993-09-17 | 1995-02-16 | Peter Dr Kuhnle | Impregnation mixture and the use thereof |
| US5413811A (en) * | 1994-03-18 | 1995-05-09 | Kimberly-Clark Corporation | Chemical and mechanical softening process for nonwoven web |
| US5830240A (en) * | 1996-10-23 | 1998-11-03 | Solutia Inc. | Fibers and textile materials having enhanced dyeability and finish compositions used thereon |
| US5944852A (en) * | 1996-10-23 | 1999-08-31 | Solutia Inc. | Dyeing process |
| GB0029198D0 (en) * | 2000-11-30 | 2001-01-17 | Ciba Sc Holding Ag | Liquid dispersion polymer compositions their preparation and their use |
| DE10242762A1 (en) * | 2002-09-14 | 2004-03-18 | Cognis Deutschland Gmbh & Co. Kg | Aqueous dispersion of copolymerisates and emulsifiers which when combined with fluorinated compounds enable the proportion of these to be decreased without impairing hydrophobization efficiency of fibers and textiles |
| WO2006023853A1 (en) * | 2004-08-23 | 2006-03-02 | Nano-Tex, Inc. | Compositions and methods for treating textiles to impart wrinkle resistance, softness and hydrophilicity |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130155C (en) * | 1962-11-10 | 1900-01-01 | ||
| DE2631419A1 (en) * | 1975-07-16 | 1977-02-03 | Procter & Gamble Europ | COMPOSITIONS FOR TEXTILE TREATMENT |
| GB1549180A (en) * | 1975-07-16 | 1979-08-01 | Procter & Gamble | Textile treating compositions |
| JPS581231B2 (en) * | 1975-12-27 | 1983-01-10 | タケモトユシ カブシキガイシヤ | Shinkinagoseisen Iyojiyunanshigesai |
| JPS52132194A (en) * | 1976-04-30 | 1977-11-05 | Lion Fat Oil Co Ltd | Softening agent composition for fiber article |
| DE2857180A1 (en) * | 1977-07-06 | 1980-01-31 | Procter & Gamble Europ | CONCENTRATED LIQUID SOFTENER COMPOSITION |
| US4155855A (en) * | 1977-07-06 | 1979-05-22 | The Procter & Gamble Company | Concentrated liquid fabric softener composition |
| DE2749386A1 (en) * | 1977-11-04 | 1979-05-10 | Roehm Gmbh | DISPERSIONS OF HYDROPHILIC ACRYLIC RESINS |
| US4179382A (en) * | 1977-11-21 | 1979-12-18 | The Procter & Gamble Company | Textile conditioning compositions containing polymeric cationic materials |
| GR67665B (en) * | 1979-05-21 | 1981-09-02 | Unilever Nv | |
| GB8428401D0 (en) * | 1984-11-09 | 1984-12-19 | Dow Corning Ltd | Organosiloxane-oxy-alkylene copolymers |
-
1986
- 1986-08-01 DE DE19863626051 patent/DE3626051A1/en not_active Withdrawn
-
1987
- 1987-07-18 DE DE8787904867T patent/DE3782665D1/en not_active Expired - Fee Related
- 1987-07-18 JP JP62504586A patent/JPH01503791A/en active Pending
- 1987-07-18 US US07/302,691 patent/US4966725A/en not_active Expired - Fee Related
- 1987-07-18 EP EP87904867A patent/EP0436524B1/en not_active Expired - Lifetime
- 1987-07-18 AT AT87904867T patent/ATE82337T1/en not_active IP Right Cessation
- 1987-07-18 WO PCT/EP1987/000391 patent/WO1988000991A2/en active IP Right Grant
- 1987-07-18 AU AU77842/87A patent/AU616157B2/en not_active Expired - Fee Related
- 1987-07-30 PT PT85462A patent/PT85462B/en not_active IP Right Cessation
- 1987-07-31 ZA ZA875678A patent/ZA875678B/en unknown
Non-Patent Citations (1)
| Title |
|---|
| Chemical Abstracts, vol. 88, no. 2, 9 January 1978 (Columbus, Ohio, US) see page 73,abstract 8447p * |
Also Published As
| Publication number | Publication date |
|---|---|
| PT85462B (en) | 1990-06-29 |
| DE3626051A1 (en) | 1988-02-11 |
| JPH01503791A (en) | 1989-12-21 |
| US4966725A (en) | 1990-10-30 |
| ATE82337T1 (en) | 1992-11-15 |
| ZA875678B (en) | 1988-03-30 |
| PT85462A (en) | 1987-08-01 |
| WO1988000991A2 (en) | 1988-02-11 |
| AU616157B2 (en) | 1991-10-24 |
| AU7784287A (en) | 1988-02-24 |
| WO1988000991A3 (en) | 1988-05-05 |
| EP0436524A1 (en) | 1991-07-17 |
| DE3782665D1 (en) | 1992-12-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0436524B1 (en) | Dispersions for preparing fibrous material | |
| DE102004002208B4 (en) | Preparations based on organopolysiloxane-polyammonium block copolymers and their use on textile substrates | |
| DE69805978T2 (en) | TEXTILE TREATMENT AGENT | |
| EP0471416B1 (en) | Aqueous dispersions of fluorinated polymers | |
| DE2631419A1 (en) | COMPOSITIONS FOR TEXTILE TREATMENT | |
| DE3402146A1 (en) | Novel quaternary ammonium compounds, their preparation and use as textile softeners | |
| EP0345552B1 (en) | Copolymers containing perfluoralkyl | |
| EP0424765A2 (en) | Dispersions of perfluoroalkyl groups containing copolymerizates | |
| EP0423565B1 (en) | Perfluoralkyl groups containing copolymers | |
| DE2011316A1 (en) | Copolymers making oil and water repellent and processes for producing the same | |
| EP0498050A2 (en) | Aqueous emulsions comprising fatty acid esters of N-methyl-N,N,N-trihydroxyethyl-ammonium-methyl-sulfate | |
| DE69101456T2 (en) | Liquid fabric softener composition. | |
| DE1935499A1 (en) | Softeners | |
| DE1469378C3 (en) | Making fibers and fiber structures dirt-repellent | |
| DE2011311B2 (en) | PROCESS FOR THE PRODUCTION OF OIL AND WATER-REPELLENT POLYMERIZES | |
| EP0354397A2 (en) | Treatment of wool and polyamide fibres | |
| EP0230910B2 (en) | Means for treating textiles | |
| DE2658575C3 (en) | ||
| EP1330569B1 (en) | Textile treatment agents | |
| DE2248829A1 (en) | PROCESS TO INCREASE THE RESISTANCE OF KERATINIC FIBERS AGAINST FELT SHRINKAGE | |
| DE102005018315B4 (en) | Aqueous preparations based on carboxy-functional organopolysiloxane-polyammonium copolymers and their use on cellulosic substrates | |
| DE4229649A1 (en) | Aqueous textile softener dispersions | |
| DE1419504C (en) | Aqueous dispersion for making textile fabrics water-repellent | |
| DE1211577B (en) | Process for antistatic finishing of fibers, threads and textiles made from them | |
| DE2757916A1 (en) | CATIONIC EMULSIFIERS |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 19881117 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE FR GB IT LI NL |
|
| 17Q | First examination report despatched |
Effective date: 19910903 |
|
| RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: PFERSEE CHEMIE GMBH |
|
| GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
| AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AT BE CH DE FR GB IT LI NL |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRE;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.SCRIBED TIME-LIMIT Effective date: 19921111 Ref country code: FR Effective date: 19921111 Ref country code: GB Effective date: 19921111 Ref country code: BE Effective date: 19921111 Ref country code: NL Effective date: 19921111 |
|
| REF | Corresponds to: |
Ref document number: 82337 Country of ref document: AT Date of ref document: 19921115 Kind code of ref document: T |
|
| REF | Corresponds to: |
Ref document number: 3782665 Country of ref document: DE Date of ref document: 19921217 |
|
| EN | Fr: translation not filed | ||
| NLV1 | Nl: lapsed or annulled due to failure to fulfill the requirements of art. 29p and 29m of the patents act | ||
| GBV | Gb: ep patent (uk) treated as always having been void in accordance with gb section 77(7)/1977 [no translation filed] |
Effective date: 19921111 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 19930707 Year of fee payment: 7 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: AT Effective date: 19930718 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Effective date: 19930731 Ref country code: CH Effective date: 19930731 |
|
| PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
| 26N | No opposition filed | ||
| REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Effective date: 19950401 |