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US3812201A - Textile finishing composition and process - Google Patents

Textile finishing composition and process Download PDF

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Publication number
US3812201A
US3812201A US00229482A US22948272A US3812201A US 3812201 A US3812201 A US 3812201A US 00229482 A US00229482 A US 00229482A US 22948272 A US22948272 A US 22948272A US 3812201 A US3812201 A US 3812201A
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Prior art keywords
composition
resins
textile
resin
fabric
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US00229482A
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A Bey
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Corning Inc
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Corning Inc
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Priority to US00229482A priority Critical patent/US3812201A/en
Priority to CA157,408A priority patent/CA1005183A/en
Priority to AU49382/72A priority patent/AU468734B2/en
Priority to IT33434/72A priority patent/IT972787B/en
Priority to JP48010646A priority patent/JPS4896899A/ja
Priority to DE19732307622 priority patent/DE2307622B2/en
Priority to AT146973A priority patent/AT353218B/en
Priority to NL7302388.A priority patent/NL157674B/en
Priority to BE795864D priority patent/BE795864A/en
Priority to CH268373D priority patent/CH268373A4/xx
Priority to CH268373A priority patent/CH588592B5/xx
Priority to FR7306487A priority patent/FR2173249B1/fr
Priority to GB889773A priority patent/GB1425858A/en
Application granted granted Critical
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • 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
    • D06M15/6433—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing carboxylic 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
    • 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
    • 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
    • D06M15/653—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain modified by isocyanate compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S525/906—Polysulfone
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S525/908—Polymer containing a hydantoin group

Definitions

  • Another object of this invention is to provide a composition and process for finishing textiles which imparts wash and wear properties thereto and which also imparts better flat appearance.
  • This invention also has as an object the provision of a textile finishing composition and process which imparts wash and wear properties to the textile with less durable press resin being required than if it were used alone.
  • any of the well known durable press resins can be used in the composition of this invention.
  • examples of such resins include the urea formaldehyde resins, melamineformaldehyde resins, dimethylolethylene urea resins, dimethylolpropylene urea resins, methylol imidazolidone resins, dimethylol dihydroxyethylene urea resins, glyoxal diurein resins, tetra-methoxymethyl dimethylene diureide resins, dimethylol uron resins, dimethylol-ethyl triazone resins, formaldehyde resins, glyoxal resins, methylol dimethyl hydantoin resins, epoxide resins, vinyl cyclohexene dioxide resins, 1:2 dichloropropanol resins, 1:3 dichloro- 2-propanol resins, pyridinium salt of ethylene bis-chloromethyl ether resins, tris
  • the composition of this invention can contain from 50 to 99% by weight of the durable press resin, but preferably contains from 70 to 97%.
  • the durable press resins commercially, are available neat or as pastes and creams in a carrier.
  • the durable press resins can be incorporated into the composition of this invention via any of the aforementioned forms, however, the amounts referred to above are with respect to the resin per se.
  • the carboxy functional siloxanes useful in this invention are well known types of materials whose general description and methods of preparation have been set forth in various places in the literature. Best results are believed to be obtained with a siloxane compolymer consisting essentially of about to 99 (preferably to 99) mole percent of units wherein R is selected from the group consisting of hydrocarbon, halohydrocarbon, cyanohydrocarbon, isocyanohydrocarbon, hydroxyhydrocarbon, mercaptohydrocarbon, etherhydrocarbon, esterhydrocarbon, thioetherhydrocarbon, thioesterhydrocarbon and nitrohydrocarbon radicals, and n has a value from 0 to 3, and about 1 to 25 (preferably 1 to 10) mole percent of R radical being ones wherein at least one of the R radicals is a methyl radical, at least 90 mole percent of all the siloxanes units in the copolymer having a degree of substitution of 2, and said siloxane copolymer having an overall degree of substitution in the
  • the composition of this invention can contain from 1 to 50% by weight of the carboxy functional siloxane, but preferably contains from 3 to 30%
  • the carboxy functional siloxanes employed herein can be used neat or in the form of a solution in an organic solvent or water. In the case of aqueous solutions, they can be mechanical emulsions of the siloxane copolymer or the emulsions obtained as a result of preparing the siloxane copolymer by emulsion polymerization. Preparation of these carboxy functional siloxane copolymers and the various types of solutions thereof are well known by those skilled in the art and will not be described in further detail here.
  • R radicals which can be present in the siloxane are the methyl, ethyl, propyl, butyl, amyl,
  • R radical contain from 1 to 18 carbon atoms.
  • divalent linking group R is the methylene, ethylene, propylene, hexamethylene, decamethylene, -CH CH(CH )CH phenyl, naphthylene, C H CH C H -CH --C H.,C H -CH radicals. It is preferred that the R' radical contain from 2 to 10 carbon atoms.
  • composition of this invention can be applied to the textile to be treated in the same manner and using the same equipment as presently used for durable press resins alone. This is of great benefit to textile finishers as no new equipment need be purchased, and no radically new processing techniques need be learned by them. Of course, other methods of applying the composition to the textile can be used if so desired.
  • compositions of this invention are best applied to the textile as a solution in a suitable organic solvent or as an aqueous emulsion.
  • compositions and process of this invention can be used in conjunction with any textile but the advantages thereof are mostly readily apparent with certain types of textile. For example, improvement in flat appearance is best seen with lightweight materials such as batiste or shirtweight materials such as cotton/polyester blends whereas the ability to reduce the durable press resin needed is best seen with mediumweight materials such as poplin.
  • a textile finishing composition was prepared which consisted essentially of 100 pounds of ethylene urea durable press resin (Proctor EU-SO), 24 pounds of magnesium chloride curing agent for the resin, 2 pounds of a nonionic polyether surfactant (Dexopal 555), 270 pounds of water, and 16 pounds of an emulsion consisting essentially of 35% of a siloxane copolymer consisting essentially of about 97.5 mole percent (CH SiO units and about 2.5 mole percent (CH )HOOCCH SCH CH S1O units, 2% of the ammonium salt of dodecylbenzenesulfonic acid, and 63% water.
  • This composition was prepared by adding the surfactant to half the water, then adding the resin, next adding the siloxane emulsion, and finally adding the curing agent in the remaining amount of water. Continuous mild agitation was used during mix- Ihe above prepared composition was applied to about 100 yards each of nine difierent styles of polyester/cotton, lightweight fabrics, which ranged from batiste weight to dress good weight. In some of these fabrics the poly ester/cotton ratio was 65/35 and in others 50/50. The fabrics were padded single dip, dried in a foot frame at a speed of about yards per minute at temperature stages of 300, 330 and 360 F.
  • the hand of the fabrics treated by the above process was extremely desirable.
  • the average flat appearance of the fabrics without any treatment (AATCC Test Method 124-1967) was 1.8 after one wash and less than 3.0 after five washes whereas the treated fabrics averaged 3.7 after one wash and 4.2 after five washes.
  • a textile finishing composition was prepared which consisted essentially of 100 pounds of ethylene urea durable press resin (Proctor EU-SOLF), 20 pounds of zinc chloride curing catalyst for the resin, 2 pounds of a nonionic surfactant (Actopal RS-l), 260 pounds of water, and 16 pounds of the siloxane copolymer emulsion used in Example 1.
  • This formulation was designed to give about a 1% pick up of the siloxane copolymer based on the dry weight of the fabric on the average fabric run.
  • the above composition was applied tovarious shirt fabrics running from lightweight batiste to mediumweight oxford weave fabrics.
  • the fabrics were dipped and nipped once. The speed of operation was about yards per minute. After treatment the fabrics were dried in a 110 foot frame at the foregoing speed at temperature stages of 300, 330 and 360 F. for about /2 a minute.
  • the gabricir were then cured in a box for 1% minutes at In Table I below the results of various tests conducted on the above treated fabrics are set forth.
  • Fabric A was a white 65/35 polyester/cotton oxford.
  • Fabric B was a gray 100% filament polyester (Fortrel).
  • Fabric C was a light blue 50/50 polyester/cotton material.
  • Fabric D was a sky blue 50/50 polyester/cotton material.
  • Fabric E was a burgundy 50/50 polyester/cotton material. Flat appear ance was measured according to AATCC Test Method 124-1967. Results of this test are an average of nine evaluations. Flex Abrasion was measured according to ASTM Test D1175-64T. Tear was measured according to ASTM Test D1424-63. Wrinkle Recovery was measured according to AATCC Test 66-1968. Handle, which is a subjective test, is reported in Table II.
  • vig y ssroft, smooth, full, and very good Dry, soft, full, and good body. Dry, soft, slightly smooth, full, and good 0 D Soft), ssome dryness, full, and very good Dry, soft, slightly smooth, full, and good Dgy, s oft, slightly smooth, full, and good o y. o E Dry, soft, smooth, full, and good body-.. Dry, soft, full, andgood body Dry, goft, full, and good body.
  • Composition C con- 38% 3,12% 18; g sisted essentially of about 1.5% carboxyfunctional silox- "i ane of composition A, about 83.2% water, about 0.3% :lggaggflgg; ggfigi? of a surfactant, about 12.5% of the glyoxal durable press resin of composition B, and about 2.5% of zinc nitrate curing agent for the durable press resin.
  • compositions were padded onto a 50/50 polyester/cotton fabric, dried, and then cured for three EXAMPLE 5 minutes at 330 F.
  • the fabric was then evaluated using Th compositions d ib d i T b VI below were various tests descnbed 1n Example 2.
  • the test results are prepared 'and applied to a 100% cotton fabric using the set forth in Table III. process described in Example 4.
  • the physical properties TABLE 111 of the fabrics were then evaluated using the the tests Flex wrinkle set forth in Example 2.'Results of; the evaluations are set abrasion recovery
  • Tensile forth m Table VII For all footnotes for Tables VI and Fabric treatment (cycles) (grams) (degrees) (pounds) 40 VII ee Table IV a d V,
  • HOKCHOzSlOhfl CH3HO0OCHCHIS10 ⁇ 11H HO (CH1) 231 195i (CH1) HOOCCHICHISCHzCHzSlO )5H CH: CH; H0O CCHzSCHzCHzlO (CHJhslO aoiCHrCI-IgS CHzCO OH JgH 35E;
  • a composition consisting essentially of about 50 to 99% by weight of a durable press resin selected from the group consisting of urea-formaldehyde, melamineformaldehyde, ethylene urea, dimethylolethylene urea, dimethylolpropylene urea, methylol imidazolidone, dimethylol dihydroxyethylene urea, glyoxal diurein, tetramethoxymethyl dimethylene diureide, dimethylol uron, dimethylol-ethyl triazone, formaldehyde, glyoxal, methylol dirnethyl hydantoin, epoxide resins, vinyl cyclohexene dioxide, 1:2 dichloropropanol, 1:3 dichloro-Z-propanol, pyridiniurn salt of ethylene bis-chloromethyl ether, tris-( laziridinyl) phosphine oxide, divinyl sul
  • composition as defined in claim 2 wherein (A) consists essentially of (CH SiO units and (B) consists essentially of (CH )HOOCCH SCH CH SiO units.
  • composition as defined in claim 3 wherein the durable press resin is an ethylene urea.
  • composition as defined in claim 3 wherein the durable press resin is a methylol imidazolidone.
  • a process for finishing a textile comprising applying as the finish a composition consisting essentially of a durable press resin and a carboxy functional siloxane as defined in claim 2, the finish composition being applied to the textile in an amount such that there is a pick up on the textile, based on the weight of the textile, of 5 to 25% by weight of the durable press resin and 0.25 to 5% by weight of the carboxy functional siloxane.
  • the durable press resin is a methylol imidazolidone and the siloxane 10 consists essentially of (A) about 90 to 99 mole percent (CH SiO units and (B) about 1 to 10 mole percent (CH )HOOCCH SCH CH SiO units.

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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)

Abstract

APPLICATION OF A COMPOSITION CONSISTING ESSENTIALLY OF A DURABLE PRESS RESIN AND A CARBOXY FUNCTIONAL SILOXANE TO SOME TEXTILES HAS BEEN FOUND TO IMPART IMPROVED TEAR STRENGTH, ABRASION RESISTANCE AND FLAT APPEARANCE.

Description

nited States Patent 3,812,201 TEXTILE FINISHING COMPOSITION AND PROCESS Alvin E. Bey, Midland, Mich., assignor to Dow Corning Corporation, Midland, Mich. No Drawing. Filed Feb. 25, 1972, Ser. No. 229,482
Int. Cl. C08g 37/38, 47/10 US. Cl. 260-824 R 9 Claims ABSTRACT OF THE DISCLOSURE Application of a composition consisting essentially of a durable press resin and a carboxy functional siloxane to some textiles has been found to impart improved tear strength, abrasion resistance and flat appearance.
The development of durable press resins for textile treating followed from the development of the urea-formaldehyde condensates in the early 1930s which were used to control the shrinkage of rayon and'cotton.
The simple urea-formaldehyde resins were followed by the melamine-formaldehyde resins, then dimethylolethylene urea, dimethylolpropylene urea, dimethylol dihydroxyethylene urea, glyoxol urein, dimethylolethyl triazone, and other resins. More recently, another group of materials, namely the epoxides, divinyl sulfone derivatives, epichlorohydrin compounds, ethyl carbonate, and others have also found use in this area.
While all of the foregoing materials are, or have been, used in the manufacture of textile products which are easy to care for in that they require little or no ironing, i.e., the wash and wear materials, they do not all achieve their goal in the same manner. The materials such as dimethylolethylene urea, its triazone, tr-azine and imidazoline variations, formaldehyde, formals, glyoxal, epoxy resins, and divinyl sulfone derivatives, for example, tend to crosslink the cellulose thereby immobilizing the fiber. This stiffening of the textile results in a poor, broady hand and a loss of tear strength and abrasion resistance. On the other hand other materials such as urea-formaldehyde and other resin condensates tend to fill up the amorphous areas of the textile and produce the same poor quality products.
In spite of the abovementioned drawbacks, durable press resin textile finishes have found wide use and acceptance, particularly in the last decade, and have almost eliminated the starch and oil finishes for garment fabrics. Many attempts have been made to eliminate or minimize the aforementioned problems, but generally such attempts have not been completely sucessful.
It is an object of this invention to provide a composition and process for finishing textiles which imparts wash and wear properties thereto with a minimal loss of tear strength and abrasion resistance.
Another object of this invention is to provide a composition and process for finishing textiles which imparts wash and wear properties thereto and which also imparts better flat appearance.
This invention also has as an object the provision of a textile finishing composition and process which imparts wash and wear properties to the textile with less durable press resin being required than if it were used alone.
It has now been found that by using a composition consisting essentially of 50 to 99% by weight of a durable press resin and 1 to 50% by weight of a carboxy functional siloxane as a textile finishing composition that the adverse effects of the durable press resin on some textiles can be substantially improved.
Other objects and advantages of this invention will be apparent from the following description and examples.
Any of the well known durable press resins can be used in the composition of this invention. Examples of such resins include the urea formaldehyde resins, melamineformaldehyde resins, dimethylolethylene urea resins, dimethylolpropylene urea resins, methylol imidazolidone resins, dimethylol dihydroxyethylene urea resins, glyoxal diurein resins, tetra-methoxymethyl dimethylene diureide resins, dimethylol uron resins, dimethylol-ethyl triazone resins, formaldehyde resins, glyoxal resins, methylol dimethyl hydantoin resins, epoxide resins, vinyl cyclohexene dioxide resins, 1:2 dichloropropanol resins, 1:3 dichloro- 2-propanol resins, pyridinium salt of ethylene bis-chloromethyl ether resins, tris (l-aziridinyl) phosphine oxide resins, divinyl sulfone derivative resins, sodium thiosulfate adduct of bis-hydroxyethyl sulfone resins, tris-(beta sulfate-ethyl) sulfonium salt resins, ethyl N,N-dimethylol carbamate resins, and tris (N-methylol-Z-carbamoyl ethyl amine) resins. The composition of this invention can contain from 50 to 99% by weight of the durable press resin, but preferably contains from 70 to 97%. The durable press resins, commercially, are available neat or as pastes and creams in a carrier. The durable press resins can be incorporated into the composition of this invention via any of the aforementioned forms, however, the amounts referred to above are with respect to the resin per se.
The carboxy functional siloxanes useful in this invention are well known types of materials whose general description and methods of preparation have been set forth in various places in the literature. Best results are believed to be obtained with a siloxane compolymer consisting essentially of about to 99 (preferably to 99) mole percent of units wherein R is selected from the group consisting of hydrocarbon, halohydrocarbon, cyanohydrocarbon, isocyanohydrocarbon, hydroxyhydrocarbon, mercaptohydrocarbon, etherhydrocarbon, esterhydrocarbon, thioetherhydrocarbon, thioesterhydrocarbon and nitrohydrocarbon radicals, and n has a value from 0 to 3, and about 1 to 25 (preferably 1 to 10) mole percent of R radical being ones wherein at least one of the R radicals is a methyl radical, at least 90 mole percent of all the siloxanes units in the copolymer having a degree of substitution of 2, and said siloxane copolymer having an overall degree of substitution in the range of about 1.8 to 2.1. The composition of this invention can contain from 1 to 50% by weight of the carboxy functional siloxane, but preferably contains from 3 to 30% The carboxy functional siloxanes employed herein can be used neat or in the form of a solution in an organic solvent or water. In the case of aqueous solutions, they can be mechanical emulsions of the siloxane copolymer or the emulsions obtained as a result of preparing the siloxane copolymer by emulsion polymerization. Preparation of these carboxy functional siloxane copolymers and the various types of solutions thereof are well known by those skilled in the art and will not be described in further detail here.
Specific examples of R radicals which can be present in the siloxane are the methyl, ethyl, propyl, butyl, amyl,
hexyl, octyl, decyl, dodecyl, octadecyl, myricyl, vinyl, allyl, hexenyl, cyclobutyl, cyclohexyl, phenyl, xenyl, naphthyl, benzyl, 2 phenylethyl, tolyl, xylyl, mesityl, 3 chloropropyl, 4 bromobutyl, 3,3,3 trifluoropropyl, chlorocyclohexyl, bromophenyl, chlorophenyl, alpha, alpha,alpha-trifiuorotolyl, dichloroxenyl, 2 cyanoethyl, 3-cyanopropyl, cyanophenyl, 3 isocyanopropyl, 6 1S0- cyanohexyl, 3-hydroxypropyl, 5 hydroxypentyl, hydroxyphenyl, hydroxynaphthyl, mercaptoethyl, mercaptopropyl, mercaptohexyl, mercaptophenyl, (CH OC H 2) s a 2) a z s,
-( 2 s a 2) s z s,
-(CH COSCH nitrophenyl and 3 nitropropyl radicals. It is preferred that the R radical contain from 1 to 18 carbon atoms.
Specific examples of the divalent linking group R are the methylene, ethylene, propylene, hexamethylene, decamethylene, -CH CH(CH )CH phenyl, naphthylene, C H CH C H -CH --C H.,C H -CH radicals. It is preferred that the R' radical contain from 2 to 10 carbon atoms.
The composition of this invention can be applied to the textile to be treated in the same manner and using the same equipment as presently used for durable press resins alone. This is of great benefit to textile finishers as no new equipment need be purchased, and no radically new processing techniques need be learned by them. Of course, other methods of applying the composition to the textile can be used if so desired.
In applying the finish composition of this invention to a textile enough should be applied so that a pick up by the textile, based on the weight of the textile, of 5 to 25% by weight of durable press resin and 0.25 to 5% by weight of the carboxy functional siloxane is achieved. The compositions of this invention are best applied to the textile as a solution in a suitable organic solvent or as an aqueous emulsion.
The compositions and process of this invention can be used in conjunction with any textile but the advantages thereof are mostly readily apparent with certain types of textile. For example, improvement in flat appearance is best seen with lightweight materials such as batiste or shirtweight materials such as cotton/polyester blends whereas the ability to reduce the durable press resin needed is best seen with mediumweight materials such as poplin.
While water-repellents, flame-proofers, wool-shrinkage control agents, pigment fixatives, nonwoven fabric binders, flock binders and other conventional textile finishing materials can also be applied to textiles treated with the composition of this invention, the compatibility of each must be checked as well as any possibility of deleterious effects on the performance of the composition of the instant invention.
Now in order that those skilled in the art may better understand how the present invention can be practiced, the following examples are given by way of illustration and not by way of limitation. All parts and percents referred to herein are by weight unless otherwise specified.
EXAMPLE 1 A textile finishing composition was prepared which consisted essentially of 100 pounds of ethylene urea durable press resin (Proctor EU-SO), 24 pounds of magnesium chloride curing agent for the resin, 2 pounds of a nonionic polyether surfactant (Dexopal 555), 270 pounds of water, and 16 pounds of an emulsion consisting essentially of 35% of a siloxane copolymer consisting essentially of about 97.5 mole percent (CH SiO units and about 2.5 mole percent (CH )HOOCCH SCH CH S1O units, 2% of the ammonium salt of dodecylbenzenesulfonic acid, and 63% water. This composition was prepared by adding the surfactant to half the water, then adding the resin, next adding the siloxane emulsion, and finally adding the curing agent in the remaining amount of water. Continuous mild agitation was used during mix- Ihe above prepared composition was applied to about 100 yards each of nine difierent styles of polyester/cotton, lightweight fabrics, which ranged from batiste weight to dress good weight. In some of these fabrics the poly ester/cotton ratio was 65/35 and in others 50/50. The fabrics were padded single dip, dried in a foot frame at a speed of about yards per minute at temperature stages of 300, 330 and 360 F. In tandem with the frame was a cure box (oven) with a capacity of 150 yards of fabric, and after drying the fabrics were cured in this box for about 1 /2 minutes at 320 F. A pickup of about 0.75% of siloxane based on the dry weight of the fabric was obtained.
The hand of the fabrics treated by the above process was extremely desirable. The average flat appearance of the fabrics without any treatment (AATCC Test Method 124-1967) was 1.8 after one wash and less than 3.0 after five washes whereas the treated fabrics averaged 3.7 after one wash and 4.2 after five washes.
EXAMPLE 2 A textile finishing composition was prepared which consisted essentially of 100 pounds of ethylene urea durable press resin (Proctor EU-SOLF), 20 pounds of zinc chloride curing catalyst for the resin, 2 pounds of a nonionic surfactant (Actopal RS-l), 260 pounds of water, and 16 pounds of the siloxane copolymer emulsion used in Example 1. This formulation was designed to give about a 1% pick up of the siloxane copolymer based on the dry weight of the fabric on the average fabric run.
The above composition was applied tovarious shirt fabrics running from lightweight batiste to mediumweight oxford weave fabrics. The fabrics were dipped and nipped once. The speed of operation was about yards per minute. After treatment the fabrics were dried in a 110 foot frame at the foregoing speed at temperature stages of 300, 330 and 360 F. for about /2 a minute. The gabricir were then cured in a box for 1% minutes at In Table I below the results of various tests conducted on the above treated fabrics are set forth. Fabric A was a white 65/35 polyester/cotton oxford. Fabric B was a gray 100% filament polyester (Fortrel). Fabric C was a light blue 50/50 polyester/cotton material. Fabric D was a sky blue 50/50 polyester/cotton material. Fabric E was a burgundy 50/50 polyester/cotton material. Flat appear ance was measured according to AATCC Test Method 124-1967. Results of this test are an average of nine evaluations. Flex Abrasion was measured according to ASTM Test D1175-64T. Tear was measured according to ASTM Test D1424-63. Wrinkle Recovery was measured according to AATCC Test 66-1968. Handle, which is a subjective test, is reported in Table II.
TABLE I Flat appearance Flex Wrinkle abrasion Tear recovery I wash 5 washes (cycles) (pounds) (degrees) 4. 1 4. 0 10, 000+ 7. 7 153 Included for comparison.
"Average 0! eight evaluations.
TABLEII Handle Fabric Initial I wash washes a......--.- sllgb tly dry, soft, full, and very good Dry, soft,fu1l, endgoodbody Dry, soft, full, and good body. A (untreated)..:..-..... Crisp, smooth andgood body.-. Dry, crisp and dead.-....; Dry, cris and dead. B.- e 1 Very smooth, 5011:, full, andgoodbody..- Dgy soft, slightly smooth, and good D ryzi sof z, slightly smooth, and good 0 0 B (untreated) Very smooth, soft, slick, and fair body... Soft, dry, and dead. Soft, s lightly smooth, dry, and dead.
... vig y ssroft, smooth, full, and very good Dry, soft, full, and good body. Dry, soft, slightly smooth, full, and good 0 D Soft), ssome dryness, full, and very good Dry, soft, slightly smooth, full, and good Dgy, s oft, slightly smooth, full, and good o y. o E Dry, soft, smooth, full, and good body-.. Dry, soft, full, andgood body Dry, goft, full, and good body.
Included for comparison.
EXAMPLE 3 TABLE v fi d Flex Wrinkle Thr text! 6 g lg 10135 were Prepare Fabric treatment abrasion Tear recovery Tensile" Composition A consisted essentlally of about 2.0% of :1 00111905100111 (cyc s) (g m g (p s) carboxyfunctional siloxane having the general formula None 1 680 2 477 227 125 5 A 11 020 2: 144 281 122' 0 HOKCHihSiO) -mltCH9HO0CCH;SCH;CH;S1Ol-250H, B-.. 1,025 ,208 205 117 0 0:." 10,047 5,700 200 100.0 about 97.7% water, and about 0.3% of a surfactant. D 8.689 5,700 278 111.5 102.-.- 0,430 5,700 201 103.0 Composmon B consisted essentrally of about 69.7% water, 9,11 4; 210 310 108.5 and 0.3% of a surfactant; about 25.0% of a glyoxal dura- 5 3,632 317 114.5 H-. s, 005 3, 648 310 110. 5 his press resin, and about 5.0% of mm nitrate curlng 91127 $992 325 m8 3 catalyst for the durable press resin. Composition C con- 38% 3,12% 18; g sisted essentially of about 1.5% carboxyfunctional silox- "i ane of composition A, about 83.2% water, about 0.3% :lggaggflgg; ggfigi? of a surfactant, about 12.5% of the glyoxal durable press resin of composition B, and about 2.5% of zinc nitrate curing agent for the durable press resin.
The above compositions were padded onto a 50/50 polyester/cotton fabric, dried, and then cured for three EXAMPLE 5 minutes at 330 F. The fabric was then evaluated using Th compositions d ib d i T b VI below were various tests descnbed 1n Example 2. The test results are prepared 'and applied to a 100% cotton fabric using the set forth in Table III. process described in Example 4. The physical properties TABLE 111 of the fabrics were then evaluated using the the tests Flex wrinkle set forth in Example 2.'Results of; the evaluations are set abrasion recovery Tensile forth m Table VII. For all footnotes for Tables VI and Fabric treatment (cycles) (grams) (degrees) (pounds) 40 VII ee Table IV a d V,
00 sitlon:
i2 8, 689 5, 700 278 111 13' 1 2,154 303 135 c 0, 387 3, 537 324 122 None (control).. 1, 680 2,368 209 133 TABLE VI Included for com arlson. "Grab tensile-A TM test 0-1682-59'1. Percent Durable Resin EXAMPLE 4 press cata- Surfac- Composltlon Water resin lyst tant' Siloxane The compositions described in Table IV below were 8 mo 20 (l3 0 prepared and applied to a /50 polyester/cotton fabric 75.7 20.0 4.0 0.3 2 by dipping the fabric into the composition, nipping begig 8:2 g, tween rollers at 40 p.s.i. of pressure, drying the fabric at 94.0 0.3 .0: 250 F. for 5 minutes, and then curing the composition at 25:3 $13 3:8 3:2 :3, 330 F. for 3 minutes. The physical properties of the 82.0 10.0 2.0 0.3 .0 fabrics were then evaluated using the tests set forth in Example 2. Results of the evaluations are set forth in TABLE v11 Table Flex Wrinkle TABLE IV Fabric treatment abrasion Tear recovery Tensile" composition (cycles) (grams) (degrees) (pounds) Percent None (0ontro1)' 745 1, e00 200 53. 2 Durable 11* 232 804 282 45.3 1 w t piesi fi i t sn 3 4 iii Composit on a er res n 00 a yst an oxane g3: 22 2.5 2.5 ii-I 25.0 5.0 1, 508 310 32.3 04.0 0.3 .0 81 1,305 308 43.8 04.0 0.3 .0 1,344 321 32.0 04.0 0.3 2.0 70.0 12.5 2.5 0.3 2.0 70.0 12.5 2.5 0.3 20 79.0 12.5 2.5 0.3 2.0 04.0 25.0 5.0 0.3 2.0 54.0 25.0 5.0 0.3 20 04.0 25.0 5.0 0.3 20 EXAMPLE 5 Moth lol imldezolidone-about 457 solids (Permafresh 183). 1 Zinc gitmtkabout 45% 501mm 0 The composmons descnbed in Table VHI below were e ew Sigma?) oi y e lgi r r 15 1 1 1 198116? gcggog H prepared and applied to a 50/50 polyester/cotton fabric a ,HO(cfibgsiom,(CHQHOOCCHZSCQCHMO E uslng the process described in Example 4. The phys1cal Hoi(cnsh lolnml(CHQHOOOCH SCH CHZ K)inn. properties of the fabrlcs were then evaluated using the Immdadm mpwam tests set forth in Example 2. Results of the evaluations are set forth in Table IX. For all footnotes in Tables VIII and IX see Tables IV and V.
TABLE VIII Percent Durable Resin press Cat- Suriac- Silox- Composition Water resin 1 alyst i tant 3 ane i TABLE IX Flex Wrinkle Fabric treatment abrasion Tear recovery Tensile" composition (cycles) (grams) (degrees) (pounds EXAMPLE 7 The compositions described in Table X below were prepared and applied to a 50/ 50 polyester/ cotton fabric using the process described in Example 4. The physical properties of the fabrics were then evaluated using the tests set forth in Example 2. Results of the evaluations are set forth in Table XI.
TAB LE X Percent Durable Resin press cate- Surfac- Composition Water resin 1 lyst I taut Siloxane 84. 7 l2. 5 2. 5 0. 3 69. 7 25. 0 5. 0 0. 3 59. 7 25. 0 5. 0 0. 3 a 2. 0 59.7 25.0 5.0 0.3 2.0 59.7 25.0 5.0 0.3 7 2.0 74. 7 12. 5 2. 5 0. 3 4 2. 0 74.7 12.5 2.5 0.3 2.0 74. 7 12. 5 2. 5 0. 3 2.0 89. 7 0. 3 4 2. 0 89. 7 O. 3 5 2. 0 89. 7 0. 3 2. 0
Methylol imidazolidone-about 45% solids (Permnfresh 183). Zinc nitrate-about 45% solution.
3 Octyl phenoxy polyethoxy ethanol (Triton X-l00).
5 HO 1 (CHmSiO i (CH1)HOOCCH1SCH2CH2S1O lmH.
HO t (CHmSiO hut (CHQHOOCCHzSCH CH SiO H.
' Included for comparison.
TABLE XI Flex Wrinkle Fabric treatment abrasion Tear recovery Tensile" composition (cycles) (grams) (degrees) (pounds) None (control)' 1, 522 2, 511 210 130. 0 A 930 2, 301 270 125. 8 B2. 621 2, 154 303 135. 5 C 6, 750 3, 388 310 141. 3 6, 031 3, 417 312 130. 6 4, 693 3, 334 307 125. 3 6, 435 3, 654 309 128. 7 o, 263 3, 711 302 122. 7 5, 095 3, 468 297 125. 5 6, 242 4, 575 239 109. 8 7, 931 4,508 229 121. 6 6, 659 4, 455 237 122. 8
Included for comparison. "AS'IM Test D2261-64T.
EXAMPLE 8 When the following carboxy functional siloxanes are substituted for those of the preceding examples similar results are obtained.
HOKCHOzSlOhfl (CH3)HO0OCHCHIS10}11H HO (CH1) 231 195i (CH1) HOOCCHICHISCHzCHzSlO )5H CH: CH; H0O CCHzSCHzCHzlO (CHJhslO aoiCHrCI-IgS CHzCO OH JgH 35E;
51(0 H: a Hgclfilshsio Ml (CH3) 0151131310 )11 (CHQHOOCCILSCEHCHI (CH3) 1.15%. HO (C Hz): 10 lololHSCHrCHiCHrSlOi/il :0! (CHHQHOOC- CHzSCH CH 10 H (oHmNofiroHroHrsiol(01191810101.5!(CH0H00C0H,
somomsiomstomornommom):
That which is claimed is:
1. A composition consisting essentially of about 50 to 99% by weight of a durable press resin selected from the group consisting of urea-formaldehyde, melamineformaldehyde, ethylene urea, dimethylolethylene urea, dimethylolpropylene urea, methylol imidazolidone, dimethylol dihydroxyethylene urea, glyoxal diurein, tetramethoxymethyl dimethylene diureide, dimethylol uron, dimethylol-ethyl triazone, formaldehyde, glyoxal, methylol dirnethyl hydantoin, epoxide resins, vinyl cyclohexene dioxide, 1:2 dichloropropanol, 1:3 dichloro-Z-propanol, pyridiniurn salt of ethylene bis-chloromethyl ether, tris-( laziridinyl) phosphine oxide, divinyl sulfone derivatives, sodium thiosulfate adduct of bis-hydroxyethyl sulfone, tris(beta sulfato-ethyl) sulfonium salt, ethyl N,N-dimethylol carbamate and tris (N-methylol-2-carbamoyl ethyl amine) resins, and about 1 to 50% by weight of a carboxy functional siloxane copolymer consisting essentially of (A) about to 99 mole percent of units wherein R is selected from the group consisting of hydrocarbon, halohydrocarbon, cyanohydrocarbon, isocyanohydrocarbon, hydroxyhydrocarbon, mercaptohydrocarbon, etherhydrocarbon, esterhydrocarbon, thioetherhydrocarbon, thioesterhydrocarbon, and nitrohydrocarbon radicals, and n has a value of from 0 to 3 and (B) about 1 to 25 mole percent of units wherein R is as defined above, R is a divalent linking group attached to the silicon atom via a silicon-carbon bond, said R being selected from the group consisting of divalent hydrocarbon radicals, divalent radicals consisting of carbon, hydrogen and oxygen atoms, and divalent radicals consisting of carbon, hydrogen and sulfur atoms, and m has a value of from 0 to 2, at least mole percent of all the siloxane units in the siloxane copolymer containing an R radical being ones wherein at least one of the R radicals is a methyl radical, at least 90 mole percent of all the siloxane units in the copolymer having a degree of substitution of 2, and said siloxane copolymer having an overall degree of substitution in the range of about 1.8 to 2.1.
2. A composition as defined in claim 1 wherein (A) is about 90 to 99 mole percent and (B) is about 1 to 10 mole percent.
3. A composition as defined in claim 2 wherein (A) consists essentially of (CH SiO units and (B) consists essentially of (CH )HOOCCH SCH CH SiO units.
4. A composition as defined in claim 3 wherein the durable press resin is an ethylene urea.
5. A composition as defined in claim 3 wherein the durable press resin is a glyoxal.
6. A composition as defined in claim 3 wherein the durable press resin is a methylol imidazolidone.
7. In a process for finishing a textile, the improvement which comprises applying as the finish a composition consisting essentially of a durable press resin and a carboxy functional siloxane as defined in claim 2, the finish composition being applied to the textile in an amount such that there is a pick up on the textile, based on the weight of the textile, of 5 to 25% by weight of the durable press resin and 0.25 to 5% by weight of the carboxy functional siloxane.
8. A process as defined in claim 7 wherein the textile is a polyester/cotton blend.
9. A process as defined in claim 8 wherein the durable press resin is a methylol imidazolidone and the siloxane 10 consists essentially of (A) about 90 to 99 mole percent (CH SiO units and (B) about 1 to 10 mole percent (CH )HOOCCH SCH CH SiO units.
References Cited UNITED STATES PATENTS 2,819,245 1/1958 Shorr 260'826 3,619,278 11/1971 Ogawa 117139.5 3,677,810 7/1972 Campbell et a1 260826 WILBERT J. BRIGGS, SR., Primary Examiner US. Cl. X.R.
117l39.5 A; 260-465 R, 824 EP, 826, 827, 830 R, 874
US00229482A 1972-02-25 1972-02-25 Textile finishing composition and process Expired - Lifetime US3812201A (en)

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CA157,408A CA1005183A (en) 1972-02-25 1972-11-24 Textile finishing composition and process
AU49382/72A AU468734B2 (en) 1972-02-25 1972-11-29 Composition and process for durable press finish
IT33434/72A IT972787B (en) 1972-02-25 1972-12-22 COMPOSITION AND PROCESS FOR THE AP PRICE OR FINISHING OF FABRICS
JP48010646A JPS4896899A (en) 1972-02-25 1973-01-25
DE19732307622 DE2307622B2 (en) 1972-02-25 1973-02-16 EQUIPMENT FOR TEXTILES AND PROCESS FOR EQUIPMENT OF TEXTILES
AT146973A AT353218B (en) 1972-02-25 1973-02-20 PROCEDURE FOR PERMANENTLY TEMPORARY EQUIPMENT OF TEXTILES AND MEANS OF CARRYING OUT THE PROCEDURE
NL7302388.A NL157674B (en) 1972-02-25 1973-02-21 PROCESS FOR PREPARING A MIXTURE OF A RESIN THAT FUNCTIONS AS A CROSSING AGENT FOR CELLULOSE MOLECULES AND AN ORGANOPOLYSILOXAN AND A PROCESS FOR PREPARING TEXTILE PRODUCTS WITH THIS MIXTURE.
BE795864D BE795864A (en) 1972-02-25 1973-02-23 COMPOSITION AND METHOD FOR FINISHING TEXTILES
CH268373D CH268373A4 (en) 1972-02-25 1973-02-23
CH268373A CH588592B5 (en) 1972-02-25 1973-02-23
FR7306487A FR2173249B1 (en) 1972-02-25 1973-02-23
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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3980729A (en) * 1974-06-19 1976-09-14 Shin-Etsu Chemical Company Limited Silicone resin compositions
US4011362A (en) * 1974-04-01 1977-03-08 Dow Corning Corporation Metal substrates with carboxyfunctional siloxane release coatings
US4311626A (en) * 1980-09-25 1982-01-19 Toray Silicone Company, Ltd. Silicone compositions for the treatment of fibers
US4477514A (en) * 1983-11-14 1984-10-16 Dow Corning Corporation Method for treating cellulosic textile fabrics with aqueous emulsions of carboxyfunctional silicone fluids
US4501619A (en) * 1983-11-14 1985-02-26 Dow Corning Corporation Aqueous emulsions of carboxyl-containing silicone fluids and a method for their preparation
US4702953A (en) * 1984-05-15 1987-10-27 Bayer Aktiengesellschaft Laminates of polyhydantoins
US4857212A (en) * 1987-04-24 1989-08-15 Toray Silicone Co., Ltd. Fiber-treating composition comprising microemulsion of carboxy-substituted siloxane polymer and use thereof
WO1998010648A1 (en) * 1996-09-13 1998-03-19 The Regents Of The University Of California Durable and regenerable microbiocidal textiles
WO1999058758A1 (en) * 1998-05-11 1999-11-18 The Procter & Gamble Company Durable press/wrinkle-free process
US6241783B1 (en) 1996-09-13 2001-06-05 The Regents Of The University Of California Formaldehyde scavenging in microbiocidal articles
US6309796B1 (en) * 1997-08-06 2001-10-30 Shin-Etsu Chemical Co., Ltd. High molecular weight silicone compounds resist compositions, and patterning method
US20040127667A1 (en) * 2002-06-14 2004-07-01 Worley Shelby D. N-halamine siloxanes for use in biocidal coatings and materials
US6962608B1 (en) 2002-10-01 2005-11-08 The Regents Of The University Of California Regenerable antimicrobial polymers and fibers with oxygen bleaches

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Publication number Priority date Publication date Assignee Title
DE3364275D1 (en) * 1982-11-16 1986-07-31 Dow Corning Organosiloxane polymers and treatment of fibres therewith
EP0360383A3 (en) * 1988-09-21 1991-12-11 International Paper Company Resilient cotton fiber and related method

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BE523008A (en) * 1952-09-23
FR1297502A (en) * 1960-08-15 1962-06-29 Thomson Houston Comp Francaise Waterproofing compositions
US3379564A (en) * 1965-01-07 1968-04-23 Du Pont Method of coating a synthetic polymeric material by cross-linking a polysiloxane containing 2-cyanoethyl and 2-carboxyethyl groups

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4011362A (en) * 1974-04-01 1977-03-08 Dow Corning Corporation Metal substrates with carboxyfunctional siloxane release coatings
US3980729A (en) * 1974-06-19 1976-09-14 Shin-Etsu Chemical Company Limited Silicone resin compositions
US4311626A (en) * 1980-09-25 1982-01-19 Toray Silicone Company, Ltd. Silicone compositions for the treatment of fibers
US4477514A (en) * 1983-11-14 1984-10-16 Dow Corning Corporation Method for treating cellulosic textile fabrics with aqueous emulsions of carboxyfunctional silicone fluids
US4501619A (en) * 1983-11-14 1985-02-26 Dow Corning Corporation Aqueous emulsions of carboxyl-containing silicone fluids and a method for their preparation
EP0146756A1 (en) * 1983-11-14 1985-07-03 Dow Corning Corporation Aqueous emulsions of carboxyl-containing silicone fluids and a method for their preparation
US4702953A (en) * 1984-05-15 1987-10-27 Bayer Aktiengesellschaft Laminates of polyhydantoins
US4857212A (en) * 1987-04-24 1989-08-15 Toray Silicone Co., Ltd. Fiber-treating composition comprising microemulsion of carboxy-substituted siloxane polymer and use thereof
US6241783B1 (en) 1996-09-13 2001-06-05 The Regents Of The University Of California Formaldehyde scavenging in microbiocidal articles
WO1998010648A1 (en) * 1996-09-13 1998-03-19 The Regents Of The University Of California Durable and regenerable microbiocidal textiles
US5882357A (en) * 1996-09-13 1999-03-16 The Regents Of The University Of California Durable and regenerable microbiocidal textiles
US6077319A (en) * 1996-09-13 2000-06-20 The Regents Of The University Of California Processes for preparing microbiocidal textiles
US6730453B2 (en) 1997-08-06 2004-05-04 Shin Etsu Chemical Co., Ltd. High molecular weight silicone compounds, resist compositions, and patterning method
US6309796B1 (en) * 1997-08-06 2001-10-30 Shin-Etsu Chemical Co., Ltd. High molecular weight silicone compounds resist compositions, and patterning method
US20020058205A1 (en) * 1997-08-06 2002-05-16 Mutsuo Nakashima High molecular weight silicone compounds, resist compositions, and patterning method
WO1999058758A1 (en) * 1998-05-11 1999-11-18 The Procter & Gamble Company Durable press/wrinkle-free process
US20040127667A1 (en) * 2002-06-14 2004-07-01 Worley Shelby D. N-halamine siloxanes for use in biocidal coatings and materials
US6969769B2 (en) 2002-06-14 2005-11-29 Vanson Halosource, Inc. N-halamine siloxanes for use in biocidal coatings and materials
US20080003438A1 (en) * 2002-06-14 2008-01-03 Auburn University Heterocyclic siloxanes for use in biocidal coatings and materials
US6962608B1 (en) 2002-10-01 2005-11-08 The Regents Of The University Of California Regenerable antimicrobial polymers and fibers with oxygen bleaches

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JPS4896899A (en) 1973-12-11
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GB1425858A (en) 1976-02-18
CH588592B5 (en) 1977-06-15
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DE2307622B2 (en) 1976-04-29
FR2173249B1 (en) 1978-08-04
AT353218B (en) 1979-11-12
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CH268373A4 (en) 1976-10-15

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