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
  • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino 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
• • 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
  • D06M2200/50—Modified hand or grip properties; Softening compositions

Definitions

• the invention relates to a method for the treatment of organic fibers with amino functional Organosilicon compounds.
• Siloxanes bearing ammonium groups are already from the literature has been known for a long time Ways described.
• a synthesis route, such as B. in GB-A 2 201 433 describes epoxy functional Silicones made by a hydrosilylation reaction of Si-H Group-bearing siloxanes with a vinyl group bearing epoxy (e.g. allyl glycidyl ether) can be obtained, and uses these epoxy-functional silicones with ammonium salts tertiary amines to form ammonium group-bearing silicones.
• a Another option is to start with To produce aminoalkyl siloxane and this then quaternize with alkylating agents like this is described for example in EP-A 436 359.
• the ones used today in textile finishing as plasticizers The vast majority of aminosiloxanes contribute Aminoethylaminopropyl side groups or Aminopropylpit phenomenon. This in neutralized form cationic side groups are aimed at the fiber surface and create an orientation of the siloxane on the Fiber surface. This leads to an extremely soft and pleasant grip on treated textile substrates.
• the Aminosiloxanes are usually in the form of emulsions applied. This represents the final step that so-called equipment, in the production of textiles Form structures and can by so-called forced application (e.g. in the foulard) or due to the cationic character of the aminosiloxanes in principle also in the exhaust process happen.
• a major disadvantage of today in textile finishing applied aminosiloxane is the drastically deteriorated Re-wettability of the textile substrate equipped with it. This is particularly troublesome in textile finishing practice insofar that once finished textile goods no longer can be over-colored. This is particularly important because Silicones are strong due to their low refractive index show color-deepening effect and thus to color shifts being able to lead. The bad is also in the case of incorrect staining Rewettability of silicone softeners Goods annoying, since it can hardly be corrected. About that There are also articles in consumer textiles for which a fluffy soft grip is desired, but a good one Resettability is absolutely necessary, e.g. B. Terry goods for towels, underwear, etc. Similar Requirements also apply to nonwovens items, e.g. B. in body care. For this article also strived for a soft grip, without this Absorbency should be affected.
• the task was to develop a procedure for the treatment of organic fibers with amino functional
• the amino-functional organosilicon compounds with it treated organic fibers such as textiles, a soft Grip and good rewettability give without that Thermal yellowing of the treated organic fibers negatively influence.
• the invention relates to a process for the treatment of organic fibers with aqueous preparations containing amino-functional organosilicon compounds of the general formula H 2 NR 1 -SiR 2 O (SiR 2 O) i SiR 2 -R 1 -NH 2 where i is an integer from 1 to 1000, preferably 20 to 650, R can be the same or different and represents a monovalent hydrocarbon radical having 1 to 18 carbon atoms per radical and R 1 represents a divalent hydrocarbon radical having 2 to 10 carbon atoms.
• organosilicon compounds according to the invention are preferably linear diorganopolysiloxanes with terminal SiC-bonded Amino groups.
• the organosilicon compounds according to the invention have preferably a viscosity of 30 to 10,000 mPa ⁇ s at 25 ° C, preferably a viscosity of 30 to 5000 mPa's at 25 ° C.
• the organosilicon compounds according to the invention have preferably an amine number of 1.35 to 0.035 mmol / g, preferred 1.35 to 0.042 mmol / g.
• radicals R are alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, iso-butyl, tert-butyl, n-pentyl, iso-pentyl, neo-pentyl, tert-pentyl, Hexyl radicals, such as the n-hexyl radical, heptyl radicals, such as the n-heptyl radical, octyl radicals, such as the n-octyl radical and iso-octyl radicals, such as the 2,2,4-trimethylpentyl radical, nonyl radicals, such as the n-nonyl radical, decyl radicals, such as the n-decyl radical, dodecyl radicals, like the n-dodecyl radical, and octadec
• the radical R is preferably an alkyl radical with 1 to 6 Carbon atom (s) per residue, preferably a methyl residue.
• radical R 1 examples are the ethylene, n-propylene, iso-propylene, n-butylene, cyclohexylene, phenylene and butenylene radical.
• the radical R 1 is preferably an alkylene radical, preferably an alkylene radical with 3 and 4 carbon atoms, particularly preferably an n-propylene radical.
• Organosilicon compounds are, for example, as follows Process manufactured: In a first stage, a short-chain dialkylpolysiloxane, which on the two End groups carries a reactive Si-H group, with N, N-bis (trimethylsilyl) allylamine with the addition of a Hydrosilylation catalyst implemented. In the second stage the resulting ⁇ , ⁇ -aminoalkylene diorganopolysiloxane under basic catalysis with methylsiloxancyclen coäquilibriert.
• aqueous preparations according to the invention are preferably an aqueous emulsion or an aqueous Solution.
• the aqueous emulsion preferably contains the amino functional according to the invention organosilicon compound optionally emulsifier, acid and water.
• the aqueous emulsions can be prepared by generally known methods.
• the emulsions can be produced in conventional mixing devices suitable for the production of emulsions, such as high-speed stator-rotor stirring devices according to Prof. P. Willems, as are known under the registered trademark "Ultra-Turrax".
• the organosilicon compounds according to the invention can be emulsified using the process described in the prior art, such as shear or phase inversion emulsification or in the heating process.
• the aqueous emulsion preferably contains known per se Emulsifiers.
• Preferred emulsifiers are nonionic emulsifiers, in particular those listed under 6 above Alkyl polyglycol ethers listed under 9 Addition products of alkylamines with ethylene oxide or Propylene oxide, the alkyl polyglycosides listed under 11 and the polyvinyl alcohol listed under 5.
• the aqueous emulsion contains emulsifiers in amounts of preferably 0 to 15% by weight, particularly preferably 1 to 10 % By weight, based in each case on the total weight of the emulsion.
• Organic or inorganic acids can be used.
• organic acids are monocarboxylic acids, such as formic acid, acetic acid, propionic acid, butyric acid, pivalic acid, sorbic acid, benzoic acid, salicylic acid, toluic acid and dicarboxylic acids, such as succinic acid, maleic acid, adipic acid, malonic acid and phthalic acid, with monocarboxylic acids being preferred and formic acid, acetic acid and propionic acid being particularly preferred.
• monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, pivalic acid, sorbic acid, benzoic acid, salicylic acid, toluic acid and dicarboxylic acids, such as succinic acid, maleic acid, adipic acid, malonic acid and phthalic acid, with monocarboxylic acids being preferred and formic acid, acetic acid and propionic acid being particularly preferred.
• acids are sulfonic acids, such as methanesulfonic acid, butanesulfonic acid, trifluoromethanesulfonic acid and toluenesulfonic acid, and also inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid and phosphoric acid. The use of these strong acids is not preferred.
• the acids are preferably used in amounts of 0.05 to 5% by weight, preferably from 0.05 to 1% by weight, based in each case on the Total weight of the aqueous emulsion used.
• the aqueous emulsions preferably contain water in Amounts of 20 to 95% by weight, preferably 30 to 85% by weight, each based on the total weight of the aqueous emulsion.
• the aqueous emulsions contain the inventive ones amino functional organosilicon compounds preferably in Amounts of 5 to 70% by weight, preferably 10 to 50% by weight, each based on the total weight of the aqueous emulsion.
• non-aqueous, but water compatible solvents like Isopropanol, diethylene glycol monomethyl ether, Diethylene glycol monobutyl ether, dipropylene glycol or Dipropylene glycol monomethyl ether can also be used.
• Impregnation of organic fibers can all organic Fibers in the form of threads, yarns or textile fabrics, such as fleeces, mats, strands, woven, knitted or knitted textiles that were previously treated Organosilicon compounds could be treated.
• fibers treated by the method according to the invention can be made of keratin, especially wool, Polyvinyl alcohol, mixed polymers of vinyl acetate, cotton, Rayon, hemp, natural silk, polypropylene, polyethylene, Polyester, polyurethane, polyamide, cellulose and mixtures of at least two such fibers.
• the fibers can be natural or be of synthetic origin.
• the textiles or textiles Fabric can be in the form of fabric or Items of clothing or parts of items of clothing are present.
• organic fibers to be treated can in any for the treatment of organic fibers suitable and well known manner, e.g. like at the beginning mentioned.
• the method according to the invention has the advantage that the treated the organosilicon compounds of the invention organic fibers have a soft feel and at the same time one have good rewettability and that they have no thermal yellowing exhibit.
• the yellow oil obtained has an amine number of 1.65 mmol / g and a viscosity of 19.3 mm 2 / s at 25 ° C.
• Example 1 Of the product obtained in Example 1 are in a Stirrer, reflux condenser and thermometer equipped 250 ml Three-neck flask 6.1 g with 193.0 g of octamethyltetrasiloxane as well 0.2 g of a 40% aqueous solution of Tetrabutylphosphonium hydroxide mixed and four with stirring Heated at 100 ° C for hours. Then it becomes the meantime clearly viscous oil again 0.1 g of the 40% aqueous Tetrabutylphosphonium hydroxide solution given and the approach stirred another two hours. It will be a clear colorless oil with a viscosity of 883 mPa * s at 25 ° C and obtained an amine number of 0.06 mmol / g.
• Example 1 Of the product obtained in Example 1 are in a Stirrer, reflux condenser and thermometer equipped 250 ml Three-necked flask 12.1 g with 187.9 g of octamethyltetrasiloxane as well 0.2 g of a 40% aqueous solution of Tetrabutylphosphonium hydroxide mixed and four with stirring Heated at 100 ° C for hours. Then it becomes the meantime clearly viscous oil again 0.1 g of the 40% aqueous Tetrabutylphosphonium hydroxide solution given and the approach stirred another two hours. It will be a clear colorless oil with a viscosity of 612 mPa * s at 25 ° C and an amine number of 0.11 mmol / g.
• Example 1 Of the product obtained in Example 1 are in a Stirrer, reflux condenser and thermometer equipped 250 ml Three-necked flask 24.2 g with 175.8 g of octamethyltetrasiloxane as well 0.2 g of a 40% aqueous solution of Tetrabutylphosphonium hydroxide mixed and four with stirring Heated at 100 ° C for hours. Then it becomes the meantime clearly viscous oil again 0.1 g of the 40% aqueous Tetrabutylphosphonium hydroxide solution given and the approach stirred another two hours. It will be a clear colorless oil with a viscosity of 180 mPa * s at 25 ° C and obtained an amine number of 0.24 mmol / g.
• Example 1 Of the product obtained in Example 1 are in a Stirrer, reflux condenser and thermometer equipped 250 ml Three-necked flask 36.4 g with 163.6 g of octamethyltetrasiloxane as well 0.2 g of a 40% aqueous solution of Tetrabutylphosphonium hydroxide mixed and four with stirring Heated at 100 ° C for hours. Then it becomes the meantime clearly viscous oil again 0.1 g of the 40% aqueous Tetrabutylphosphonium hydroxide solution given and the approach stirred another two hours. It will be a clear colorless oil with a viscosity of 132 mPa * s at 25 ° C and obtained an amine number of 0.48 mmol / g.
• 15 g of the aminosiloxane from Example 2 are stirred with 5 g of an isotridecylethoxypolyethylene glycol with an average of six ethylene oxide units, 5 g of an isotridecylethoxypolyethylene glycol with an average of eight ethylene oxide units, 1 g of glacial acetic acid and 15 g of isopropanol until a homogeneous mixture is obtained. A total of 59 g of water is then added to the mixture in small portions while stirring. A white emulsion is obtained.
• Example 3 The aminosiloxane obtained in Example 3 was prepared according to Example 6 emulsified and thereby a bluish, transparent emulsion receive.
• Example 4 The aminosiloxane obtained in Example 4 was prepared according to Example 6 emulsified and thereby a bluish, transparent emulsion receive.
• Example 5 The aminosiloxane obtained in Example 5 was prepared according to Example 6 emulsified and obtained a clear emulsion.
• a bleached, unfinished cotton terry ware with 400 g / m 2 was used for the determination of soft hand, water absorption time (hydrophilicity) and whiteness.
• the fabric was impregnated with the respective liquor, squeezed to 80% liquor absorption with a two-roll pad and dried at 120 ° C. for 10 minutes.
• the finished goods were then in the climate room for eight hours at a temperature of 23 ° C and a humidity of 50%.
• Example 16 in the table is a blank.
• the blank value water value
• Examples 10 11 12 13 14 15 16 B 6 emulsion 20 g / l B 7 emulsion 20 g / l B 8 emulsion 20 g / l B 9 emulsion 20 g / l Emulsion from V 1 20 g / l Emulsion from V2 20 g / l glacial acetic acid 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g / l 0.5 g /
• the finished sample was eight hours after finishing for acclimatization in a climate room at a temperature of 23 ° C and a humidity of 50%, then was a drop of deionized water on the surface of the fabric given and the time determined until the water drop from the fabric was soaked up, but no longer than three minutes. There were five Determinations carried out and the mean value formed.

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• Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
• Silicon Polymers (AREA)
• Paints Or Removers (AREA)

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• 2001
  • 2001-03-29 DE DE10115476A patent/DE10115476A1/de not_active Withdrawn
• 2002
  • 2002-03-14 EP EP02005359A patent/EP1245719A1/de not_active Withdrawn
  • 2002-03-26 US US10/106,662 patent/US6547981B2/en not_active Expired - Fee Related
  • 2002-03-26 JP JP2002085353A patent/JP2002363867A/ja active Pending
  • 2002-03-29 CN CN02108469A patent/CN1379147A/zh active Pending

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