US3677810A - Silicone-acrylate soil release treatment for organic textiles - Google Patents

Silicone-acrylate soil release treatment for organic textiles Download PDF

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US3677810A
US3677810A US85702A US3677810DA US3677810A US 3677810 A US3677810 A US 3677810A US 85702 A US85702 A US 85702A US 3677810D A US3677810D A US 3677810DA US 3677810 A US3677810 A US 3677810A
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fabric
weight
acid
soil release
water
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James K Campbell
Kenneth M Lee
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Dow Silicones Corp
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Dow Corning Corp
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/667Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain
    • D06M15/673Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain containing phosphorus and nitrogen in the main chain
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04Polysiloxanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/10Block- or graft-copolymers containing polysiloxane sequences
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423Amino-aldehyde resins
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/14Polysiloxanes containing silicon bound to oxygen-containing groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/14Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/14Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/20Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/22Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42Block-or graft-polymers containing polysiloxane sequences
    • C08G77/44Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences

Definitions

  • soil release refers to the phenomenon. This is to be distinguished from dry soiling or dry soil release which is particularly apropos to carpeting and drapes. In the latter, one is primarily concerned with soil build-up while the fabric is in use.
  • Applicants have found, however, quite unexpectedly that a combination of the organosiloxanes defined hereinafter and polymeric carboxylic acids as defined hereinafter, produce soil release properties equivalent to or superior to those of the polymeric carboxylic acids alone. It has also been found that the combination of silicones and the polymeric carboxylic acids give far superior hand, particularly in connection with crease resistance resins than do the polymer carboxylic acids alone. The presence of the silicone also greatly enhances the mechanical strength of the fabric which is often badly deteriorated by the use of aminoplast crease resistant resins. For example, the combination of the silicone and polymeric acid when applied in conjunction with the aminoplast resin improves the tear of the fabric by 40% or more and the flex abrasion by from 400 to 500% over the same fabric treated with the aminoplast resin alone.
  • This invention relates to a mixture of (A) an aminoplast textile resin and in amount sufiicient to increase soil release of an organic fabric to which the mixture is applied, (B) a combination of (1) from 10 to 99% by weight of a polymethylsiloxane containing at least one methyl group per silicon, the remaining substituents on the silicon being substantially all hydrogen or aliphatic hydrocarbon radicals of 1 to 2 carbon atoms and (2) from 1% to by weight of a polymeric, unsaturated, water-soluble carboxylic acid, the proportions of (l) and (2) being based on the combined weights of the two.
  • This invention also relates to the method of improving soil release of an organic fabric which comprises applying thereto the mixture of (1) and 2) of the preceding paragraph and thereafter drying the coating on the fabric.
  • drying includes curing the coating and merely removing the water or solvent under conditions where no curing occurs.
  • silicones which are operative herein are dimethylpolysiloxanes, methyl hydrogen polysiloxanes, methylvinylsiloxane and methylethylsiloxane or copolymers of these.
  • the siloxaue is a dimethylsiloxane, a methyl hydrogen siloxane or a dimethylsiloxane containing copolymerized therewith a minor amount i.e., 20 mol percent or less of methylvinylsiloxane or methylethylsiloxane.
  • the siloxanes can be endblocked with hydroxyl groups or functional groups such as alkoxy, acetoxy, etc., or they can be endblocked with R SiO units in which R is any hydrocarbon or halohydrocarbon radical.
  • the viscosity of the siloxane is not critical and it can range, for example, from 100 cs. to non-flowing gums.
  • the polysiloxane can be cured on the fabric or not depending upon the ultimate use of the fabric. If the siloxane is to be cured one can use any of the conventional crosslinkers and catalysts commonly used to cure polysiloxanes. For example, one can cure hydroxyl endblocked polysiloxanes with crosslinkers such as SiH containing siloxanes, alkoxysilanes or alkoxy silicates, acyloxysilanes, ketoxime silanes (i.e.
  • RSi(ON CR' where R and R are hydrocarbon radicals) and amineoxy silaues using catalysts such as metal salts of carboxylic acids such as dibutyl-tin-diacetate or ferric octoate or alkyl titanates such as tetrabutyl titanate or amines.
  • catalysts such as metal salts of carboxylic acids such as dibutyl-tin-diacetate or ferric octoate or alkyl titanates such as tetrabutyl titanate or amines.
  • the cure of the siloxane is not to be confused with the cure of the aminoplast resin although the two can be cured simultaneously, if desired.
  • the siloxane and polymeric acid are applied to the fabric without a curing catalyst for the siloxane and the coating is heated to remove any solvent or water.
  • the polymeric carboxylic acids used herein are polymers of unsaturated water-soluble carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid, vinylacetic acid or fumaric acid.
  • the polymeric carboxylic acid can be a homopolymer or it can be copolymer of two or more types of such acids.
  • vinylacetic or fumaric acid it is preferable to prepare a copolymer with either acrylic, methacrylic or itaconic acids.
  • the polymeric carboxylic acid of this invention can also contain small amounts of other vinylic polymers such as acrylic esters, styrene, vinylchloride, or the like.
  • the silicone and the polymeric carboxylic acid can be a copolymer or a mixture.
  • the polysiloxane can be prepared and then copolymerized with the unsaturated acid by means of standard emulsion polymerization techniques or by means of standard solvent polymerization techniques. In such techniques the preferred catalyst is potassium persulfate.
  • the siloxane contain alkenyl groups if it is desired to prepare copolymers.
  • the present invention operates perfectly well with mere blends of the polymeric carboxylic acid and the siloxane. In these circumstances the polysiloxane is prepared separately from the polymeric carboxylic acid, each being polymerized by conventional techniques.
  • the two polymers are then blended in any convenient fashion. It has been found that this can be done satisfactorily by mixing the two polymers and then passing the mixture through a colloid mill.
  • the siloxane will be in the form of a emuls1on.
  • the soil release treatment of this invention can be used in conjunction with aminoplast textile resins.
  • aminoplast textile resins These materials are well known articles of commerce. Examples of such resins are urea formaldehyde resins, melamine formaldehyde resins, ethylene urea formaldehyde resins, carbamate formaldehyde resins, amide formaldehyde resins, diurea formaldehyde resins and triazone formaldehyde resins.
  • the aminoplast resin can be cured on the textile by any of the conventional catalysts generally employed in commerce. These can be of the Lewis acid type, of the basic type or any other type desired. For a complete list of such catalysts columns 6 and 7 of the aforesaid patent are hereby incorporated by reference.
  • the aminoplast resin can be cured by other means such as by radiation.
  • the combination of this invention is applied to the fabric by any conventional means such as by padding, dipping or spraying.
  • concentration of the treating bath is not critical and can range from 0.1 to 5% or more of the combined weight of the siloxane and polymeric carboxylic acid.
  • the aminoplast resin can be applied to the normal concentration used with the particular type fabric empolyed. When aminoplast resins are used the bath can con- .4 tain conventional amounts of such resins such as from 2 to 30% or more shown in US. Pat. 3,377,249.
  • the amount of the combination of 1) and (2) on the dry fabric is not critical, nor is the relative amounts of the combination (1) and (2) and the aminoplast resin so long as the aforesaid combination is present in amount suflicient to impart soil release.
  • the wet pick up based on the dry weight of the fabric will run from 50 to of the weight of (1) and (2).
  • (l), (2) and the aminoplast resin can be applied to the fabric in combination or each ingredient can be applied alone and in any order. Preferably the materials are applied simultaneously.
  • the soil release properties of this invention are obtained with any organic fabric such as cellulosic fabrics such as cotton, rayon, cellulose acetate or viscose; polyamide fibers such as nylon; polyacrylic fabrics such as polyacrylonitrile and polyester fibers such as those arrived from ethylene glycol and terephthalic acid; protein fibers such as wool and polyvinylic fibers such as those from copolymers of vinyl chloride and vinylidene chloride or polypropylene. It should be understood that blends of any of these types of fibers can be employed, if desired.
  • Triton X-l00 is nonyl benzene poly-alkyleneoxide.
  • Permafresh-183 is dihydroxy dimethylol ethylene urea.
  • Emulphogen BC-720 is tridecyloxypoly(ethylenoxy) ethanol.
  • Abex 188 is an anionic surfactant.
  • EXAMPLE 1 An emulsion was prepared by polymerizing methacrylic acid with potassium persulfate in an emulsion of a copolymer of 98.5 mol percent dimethylsiloxane and 1.5 mol percent methylvinylsilox-ane in proportions such that the emulsion contain a weight ratio of 50% polysiloxane and 50% polyacrylic acid.
  • the resulting emulsion had a solids content of 13.7%. 26.7 g. of this emulsion was mixed with 44.7 g. of water, .3 g. of Triton X-100, 25 g. of a 45% solids water solution of Permafresh183 and 3.5 g. of a 50% water solution of magnesium chloride.
  • the resulting combination was applied to nylon fabric and cured at 250 F. for 15 minutes. After one wash in accordance with the aforesaid standard test the rating from a Sears chassis grease stain was 5, and from burnt motor oil stand was 5. This indicates excellent removal of the stain in one wash.
  • EXAMPLE 2 60 g. of methyl hydrogen polysiloxane was mixed with 136 g. of water and emulsified with 4 g. of Emulphogen 130-720. This gave a 30% solids emulsion. 25 g. of this 1 Except In Example 3.
  • emulsion was mixed with 98.8 g. of polymethacrylic acid water solution containing 7.5 g. of acid.
  • EXAMPLE 3 An emulsion of a copolymer of 98.5 dimethylsiloxane and 1.5 mol percent of methylvinylsiloxane having a concentration of 32% by weight siloxane was prepared. 56.6 g. of this emulsion was mixed with 312 g. of a 7.8% polymethacrylic acid solution. The mixture was put through a colloid mill at a setting of 20 mils followed by 3 passes at a 5 mil setting.
  • This mixture was applied to a white cloth composed of 5050 polyester-cotton blend and cured at 250 F. for 15 minutes.
  • the fabric was washed and stained in accordance with the aforementioned standard test. However, the stain removal was measured using a photovolt photoelectric cell measuring device which recorded the intensity of light reflected from the sample.
  • the cloth treated with the above mixture was checked against the same untreated unstained cloth, the same untreated stained cloth and the same cloth which was treated with the Permafresh-183 resin only and stained. Each sample was checked after one wash and after 23 washes.
  • 30.5 g. of the above emulsion was mixed with 45.7 g. of water, .3 g. of Triton X-100, 20 g. of a 45% water solution of Permafresh-183 and 3.5 g. of zinc nitrate solution.
  • the bath contained 4% of the combination of silicone and polymethacrylic acid.
  • the bath was applied to 5050 blend of polyester and cotton and cured 5 minutes at 250 F. and then 15 minutes at 250 F.
  • the fabric was stained with burnt motor oil and upon washing had much better stain removal than an identical fabric treated with a commercial acrylate soil release agent.
  • EXAMPLE 5 A 31% solids emulsion was made of a 5500 cs. copolymer of 80 mol percent dimethylsiloxane and 20 mol percent methylvinylsiloxane. 79 g. of this emulsion was mixed with 4 g. of Abex 18S and 300 g. of water and heated to 70 C. under nitrogen. 10.5 g. of a 2% potassium persulfate solution was then added, followed by 25 g. of acrylic acid over a 30 minute period. 10.5 additional grams of 2% potassium persulfate were then added and the mixture heated for 30 minutes at 70 C. and then 30' minutes at C.
  • EXAMPLE 6 This example shows use without aminoplast resin.
  • An emulsion was made of a copolymer of 98.5 mol percent dirnethylsiloxane and 1.5 mol percent methylvinylsiloxane using dodecyl benzene sulfonic acid. The solids content was 32.2% by weight. 23.9 g. of this emulsion was blended with 100 g. of 7.7% solution of a polymethacrylic acid.
  • the test with burnt motor oil showed a soil release of 2 after one wash.
  • the untreated fabric had a rating of 1 after one wash.
  • EXAMPLE 7 This example shows use of 80% dimethylpolysiloxane and 20% by weight methacrylic acid.
  • a 5050 blend of polyester-cotton fabric was immersed in the composition and put through squeeze rolls at 40 p.s.i. pressure. The fabric was treated 15 minutes at 25 0 F. The soil rating for burnt motor oil was 2 after one wash while the fabric with the Permafresh-183 alone was 1.
  • EXAMPLE 8 This example shows curing the siloxane. 3 g. of a 35% solids emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane was mixed with 0.3 g. of methyltrimethoxy silane, 0.3 g. of a 20% solids emulsion of dibutyl-tin-dilaurate, 26.3 g. of a 7.3% solids solution of polymethacrylic acid, and 69.2 g. of water.
  • This mixture was applied to a 50 50 polyester-cotton fabric and cured 20 minutes at 250 F.
  • the fabric was tested and was found after one Wash to have a stain rating of 2 against burnt motor oil and 3 against salad oil.
  • the untreated fabric gave a rating of 1 for each stain.
  • EXAMPLE 9 This example also shows curing the siloxane. It further shows that at lower concentrations the polymeric acid improves cleanability with good hand characteristics being obtainable.
  • compositions (A-H) were prepared and applied to a. white 50-50 polyester-cotton fabric.
  • the fabric samples were dipped into the compositions, nipped between rollers with 40 p.s.i. of pressure, dried, and then oven cured for 15 minutes at 250 F. The fabric samples were then tested for soil release.
  • the compositions employed are set forth below. Compositions A-C and a fabric sample without any composition were included for purposes of comparison.
  • Composition A consisted essentially of 3 g. of a 35% solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, 1 g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyl-tin-dilaurate, 0.1 g. of acetic acid and 95.6 g. of water.
  • Composition B consisted essentially of 3 g. of a 35% solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, 1 g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 1.3 g. of a 7.7% solids aqueous solution of polymethacrylic acid, and 94.4 g. of water.
  • Composition C consisted essentially of 3 g. of a 35% solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, l g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 6.5 g. of a 7.7% solids aqueous solution of polymethacrylic acid, and 89.2 g. of water.
  • Composition D consisted essentially of 3 g. of a 35% solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, 1 g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 13 g. of a 7.7% solids aqueous solution of polymethacrylic acid, and 82.7 g. of water.
  • Composition E consisted essentially of 3 g. of a 35% solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, l g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 26 g. of a 7.7% solids aqueous solution of polymethacrylic acid, and 69.7% water.
  • Composition F consisted essentially of 3 g. of a 35 solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, 1 g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 39 g. of a 7.7 solids aqueous solution of polymethacrylic acid, and 56.7% water.
  • Composition 6 consisted essentially of 3 g. of a 35 solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, 1 g. of methyltrimethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 65 g. of a 7.7% solids aqueous solution of polymethacrylic acid, and 31.7 g. of water.
  • Composition H consisted essentially of 3 g. of a 35 solids aqueous emulsion of a 100,000 cs. hydroxyl endblocked polydimethylsiloxane, 1 g. of methyltrirnethoxysilane, 0.3 g. of a 20% solids aqueous emulsion of dibutyltin-dilaurate, 94.8 g. of a 7.7 solids aqueous solution of polymethacrylic acid, and 0.9 g. of water.
  • the method of improving soil release of an organic fabric which comprises applying thereto a soil release effective amount of a combination of (1) from 10 to 99% by weight of a polymethylsiloxane containing at least one methyl group per silicon, the remaining substituents on the silicon being substantially all hydrogen or aliphatic hydrocarbon radicals of 1 to 2 carbon atoms and (2) from 1 to by Weight of a polymeric, unsaturated, Water-soluble carboxylic acid, the proportions of (1) and (2) being based on the combined Weights of (l) and (2) and thereafter drying the coating on the fabric.

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  • 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)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US85702A 1970-09-03 1970-10-30 Silicone-acrylate soil release treatment for organic textiles Expired - Lifetime US3677810A (en)

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US6946770A 1970-09-03 1970-09-03
US8570270A 1970-10-30 1970-10-30
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AT (1) AT353740B (enrdf_load_stackoverflow)
BE (1) BE772087A (enrdf_load_stackoverflow)
CA (1) CA953857A (enrdf_load_stackoverflow)
CH (3) CH559278A5 (enrdf_load_stackoverflow)
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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3770489A (en) * 1971-09-16 1973-11-06 United Merchants & Mfg Creaseproofing cellulose-based fabrics
US3787231A (en) * 1970-10-15 1974-01-22 Rhone Poulenc Sa Dentures having a dialkylpolysiloxane coating
US3871909A (en) * 1972-06-22 1975-03-18 Warnaco Inc Hosiery finishing process for treating fabrics containing spandex yarn
US3947366A (en) * 1973-07-27 1976-03-30 Andrianov Kuzma A Size for textile yarns and method of sizing thereof
US4001154A (en) * 1973-09-04 1977-01-04 The Dow Chemical Company Primer adhesive composition
US4291135A (en) * 1978-06-23 1981-09-22 Bayer Aktiengesellschaft Binders for coating compositions
US4421796A (en) * 1981-10-03 1983-12-20 Dow Corning Limited Treating textile fibres
US4477514A (en) * 1983-11-14 1984-10-16 Dow Corning Corporation Method for treating cellulosic textile fabrics with aqueous emulsions of carboxyfunctional silicone fluids
WO2002002862A3 (en) * 2000-06-30 2002-05-23 3M Innovative Properties Co Treatment of fibrous substrates with silsesquioxanes and stainblockers
US20040234868A1 (en) * 2003-05-20 2004-11-25 Cheng-Ming Lin Novel modification of mask blank to avoid charging effect

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3844825A (en) * 1972-11-30 1974-10-29 American Cyanamid Co Method of producing an acrylic fiber having an improved touch like animal hair
DE2608894A1 (de) 1976-03-04 1977-09-08 Pfersee Chem Fab Verfahren zur herstellung von modifizierten polymerisaten und deren verwendung
US4320172A (en) * 1979-07-09 1982-03-16 Shin-Etsu Chemical Co., Ltd. Organopolysiloxane resin compositions for release papers
US4425372A (en) 1981-10-09 1984-01-10 Burlington Industries, Inc. Process for making absorbent bioactive wettable medical fabric
US4448810A (en) * 1982-10-15 1984-05-15 Dow Corning Limited Treating textile fibres with quaternary salt polydiorganosiloxane
JPS63146976A (ja) * 1986-12-11 1988-06-18 Daikin Ind Ltd 撥水撥油剤組成物
DE69806056T2 (de) 1997-12-18 2003-01-23 Tremco Inc., Beachwood Polysiloxan mit dispergiertem copolymeren und dieses enthaltende dichtungsmassen
US6616980B2 (en) 2001-04-24 2003-09-09 Crompton Corporation Emulsion polymerized acrylated silicone copolymer for wrinkle reduction

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3236685A (en) * 1962-06-20 1966-02-22 Eastman Kodak Co Process for treating textile fibers and other shaped products with coatings

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3787231A (en) * 1970-10-15 1974-01-22 Rhone Poulenc Sa Dentures having a dialkylpolysiloxane coating
US3770489A (en) * 1971-09-16 1973-11-06 United Merchants & Mfg Creaseproofing cellulose-based fabrics
US3871909A (en) * 1972-06-22 1975-03-18 Warnaco Inc Hosiery finishing process for treating fabrics containing spandex yarn
US3947366A (en) * 1973-07-27 1976-03-30 Andrianov Kuzma A Size for textile yarns and method of sizing thereof
US4001154A (en) * 1973-09-04 1977-01-04 The Dow Chemical Company Primer adhesive composition
US4291135A (en) * 1978-06-23 1981-09-22 Bayer Aktiengesellschaft Binders for coating compositions
US4421796A (en) * 1981-10-03 1983-12-20 Dow Corning Limited Treating textile fibres
US4477514A (en) * 1983-11-14 1984-10-16 Dow Corning Corporation Method for treating cellulosic textile fabrics with aqueous emulsions of carboxyfunctional silicone fluids
WO2002002862A3 (en) * 2000-06-30 2002-05-23 3M Innovative Properties Co Treatment of fibrous substrates with silsesquioxanes and stainblockers
US20040234868A1 (en) * 2003-05-20 2004-11-25 Cheng-Ming Lin Novel modification of mask blank to avoid charging effect

Also Published As

Publication number Publication date
BE772087A (fr) 1972-03-02
CH559278A5 (enrdf_load_stackoverflow) 1975-02-28
DE2144337A1 (de) 1972-03-09
GB1367666A (en) 1974-09-18
DE2144337B2 (de) 1974-06-27
DE2144337C3 (de) 1975-02-20
AT353740B (de) 1979-11-26
CH1284371A4 (enrdf_load_stackoverflow) 1975-05-30
US3714287A (en) 1973-01-30
ATA771371A (de) 1979-05-15
CA953857A (en) 1974-09-03
CH568437B5 (enrdf_load_stackoverflow) 1975-10-31

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