US3622261A - Buffered aldehyde fixation composition - Google Patents

Buffered aldehyde fixation composition Download PDF

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US3622261A
US3622261A US762366A US3622261DA US3622261A US 3622261 A US3622261 A US 3622261A US 762366 A US762366 A US 762366A US 3622261D A US3622261D A US 3622261DA US 3622261 A US3622261 A US 3622261A
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process according
percent
phosphate
formaldehyde
carbamate
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US762366A
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James F Cotton
John W Reed
Water C Monk
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Westpoint Pepperell Inc
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Westpoint Pepperell Inc
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Priority claimed from DE19712138503 external-priority patent/DE2138503C3/de
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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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/12—Aldehydes; Ketones
    • D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
    • C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
    • C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/12—Aldehydes; Ketones
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/425—Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes
    • 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

Definitions

  • the present invention is directed to an improvement in the process of fixing an aldehyde on cellulose using a carbamate carrier as disclosed in Cotton et al. application 451,033 filed Apr. 26, 1965 now US. Pat. No. 3,420,696, issued Jan. 7, 1969.
  • Another object is to which retain their wash degree.
  • a further object is to scavenge unreacted formaldehyde from the treated cellulosic fabric.
  • Glycolic acid is known to self condense to form polyglycolides when glycolic acid is used in the Cotton et al. process without bufiering, the fabric becomes highly acidic on standing as moisture is absorbed. Pickup of moisture apparently allows hydrolysis of the polyglycolides to glycolic acid. This hydrolysis appears to be self-catalyzing.
  • the use of the buffers prevents the generation of acidity on standing.
  • the cellulose can be in the form of cotton, alpha cellulose,
  • viscose rayon or paper.
  • cellulose esters there can be employed cellulose acetate, e.g. 38 percent acetate content, cellulose acetate butyrate and cellulose acetate-propionate.
  • the cellulose material can be blended with synthetic fibers such as polyesters, e.g. polyethylene terephthalates, acrylic fibers, e.g. polyacrylonitrile, acrylonitrile-vinyl chloride (85: 1 5 or :85), nylon, e.g. polymeric hexamethylene adipamide or polymeric caprolactam, polypropylene, ethylenepropylene copolymer, spandex (polyurethane fibers), vinyl chloride-vinyl acetate (e.g. 87:13), A particularly NCOOR,
  • synthetic fibers such as polyesters, e.g. polyethylene terephthalates, acrylic fibers, e.g. polyacrylonitrile, acrylonitrile-vinyl chloride (85: 1 5 or :85), nylon, e.g. polymeric hexamethylene adipamide or polymeric caprolactam, polypropylene, ethylenepropylene copolymer, spandex (polyurethane fiber
  • carbamates can be employed, e.g. the eutectic mixture of 52 percent ethyl carbamate and 48 percent methyl carbamate.
  • the preferred carbamates are methyl carbamate and ethyl carbamate.
  • the temperature of heating the product in order to fix the formaldehyde to the cellulosic material can be widely varied, e.g. from to 400 F. Temperatures of 180 to 300 F. are usually employed but the temperature is not critical. The use of a partial vacuum is recommended when drying and curing at temperatures in the order of 125 F.
  • carbamate e.g. l to 5 percent or more of methyl carbamate in the aqueous mixture
  • the improvement obtained by using over 1 percent of the carbamate does not justify the increase in cost.
  • the aldehyde is employed in the aqueous system in an amount normally between 1 and 8 percent thereof although as much as 10 or 15 percent or more of formaldehyde can be used if relatively large amounts of formaldehydes are to be fixed onto the cellulose.
  • the formaldehyde is employed in an amount of at least 2 moles and preferably at least 3 moles per mole of carbamate and can be employed in an amount of at least 3 moles per mole of carbamate and can be employed in an amount as much as 60 moles or even 100 moles per mole of carbamate.
  • alpha cellulose and paper there is usually employed an aqueous mixture containing 1.25-4 percent formaldehyde, in order to fix 0.25-1.25 percent formaldehyde, on the treated material.
  • rayon and cellulose esters there usually is employed an aqueous mixture containing 2.5-8.0 percent formaldehyde, in order to fix 0.5-2.5 percent fon'naldehyde, onto the treated material.
  • the glycolic acid bath through which the cotton or other cellulosic material is passed generally contains a water soluble polyvalent metal salt catalyst as well to accelerate the reaction of the formaldehyde and cellulose although such salts can be omitted.
  • Typical examples of such salts are magnesium chloride, calcium chloride, zinc nitrate, zinc chloride, zinc fluoborate (which gives excellent scorch protection), zinc silicofluoride, magnesium nitrate, magnesium fluoborate, aluminum chloride, aluminum bromide, magnesium sulfate, alualuminum sulfate, paper maker's alum, zinc bromide, magnesium bromide, zinc iodide, magnesium iodide, zinc fluoride, zirconium oxychloride, zirconium oxybromide, titanium tetrachloride, titanium tetrabromide, zinc sulfate, calcium sulfate, barium chloride, strontium chloride, barium bromide, chromic
  • the normal procedure for applying the formaldehyde and carbamate containing aqueous mixture to the material is to pass a fabric, fibers, sheet or continuous yarn through the aqueous mixture, and then to run the thus impregnated material through squeeze rolls to remove excess solution.
  • the procedure employed can be to pass the aqueous mixture through packages of the yarn in a kier.
  • additives such as wetting agents, hand modifier, softeners, lubricants, brighteners, and the like.
  • the process fixes formaldehyde on the base material, for example on cotton yarn or fabric with considerable reduction in loss of strength as compared with conventional resin finishing processes. Drying need not be carried to the end point of zero moisture and excellent results are obtained with drying to a residual moisture content of 2-4 percent measured with a resistance type moisture measuring device. Of course the fabric can be bone dried if desired.
  • the process of the present invention imparts better whiteness retention to cellulosic fabrics, e.g. viscose rayon and cotton fabrics and fabrics containing blends of synthetic and cellulosic fibers. Greatly reduced swelling properties are also imparted to cellulosic fabrics either alone or blended with synthetic fibers.
  • the reaction occurs rapidly so that the cellulosic fibers are not collapsed or highly swollen but are in their normal state. if the fibers were collapsed before the curing with the formaldehyde there would be a reduction in regain and an embrittlement of the fibers.
  • the present treatment also eliminates the chlorine pickup encountered when cellulose fabrics are treated with aminoplasts including formaldehyde-carbamate resins to bond nitrogen to the cellulose through methylene bridges.
  • the cellulose fabrics treated according to the invention are extremely durable to laundering and retain wash-wear properties for extended periods of time.
  • hexitol or pentitol formaldehyde scavenger there can be used mannitol, sorbitol, arabitol, xylitol, heptitols, rhamnitol, or mixtures such as Sutro l70-D which is hydrogenated invert sugar.
  • This latter mixture has the same effect as mannitol and a much greater efiect than sorbitol yet costs about onetenth as much as mannitol.
  • Commercially available polyols may also be used.
  • the preferred buffer system contains monosodium phosphate and trisodium phosphate.
  • the ratio of monosodium phosphate to trisodium phosphate can range from 1:1 to i021
  • a portion of the monosodium phosphate, e.g. up to 50 percent, can be replaced by disodium phosphate.
  • disodium phosphate When employing paraformaldehyde it is desirable to employ the trisodium phosphate but when employing formalin disodium phosphate can be used to replace the trisodium phosphate.
  • tetrasodium pyrophosphate and sodium tripolyphosphate but they are not as effective as the mixture of monosodium phosphate and trisodium phosphate.
  • the corresponding potassium compounds can be used in place of the sodium compounds.
  • monopotassium phosphate, dipotassium phosphate and tripotassium phosphate there can be used monopotassium phosphate, dipotassium phosphate and tripo
  • Sodium bisulfite can be employed to reduce the formaldehyde odor and to aid in preventing yellowing. It is employed in an amount of from 0.25 percent of the aqueous mix up to one part for two arts of formaldehyde. As stated it can be omitted, particularly with industrial fabrics which do not require as outstanding properties as better quality fabrics.
  • potassium bisulfite sodium sulfite, potassium sulfite. sodium metabisulfite, sodium bisulfite-acetone.
  • magnesium salts e.g. magnesium chloride
  • While the buffer is employed to increase the pH, normally it is not raised above about a pH of 7.
  • dimethylsulfone is employed to bring the pH from the acid side up to 7, it is used in an amount of 0.1 to 5 percent of the total mix. The use of higher amounts is not precluded but is wasteful of an expensive material.
  • Ammonium salts e.g. ammonium chloride. can be used in place of the metal salt.
  • Surfactant FW is a wetting agent of the ethylene oxide condensate type. It can be replaced by an equal weight of nonylphenol-ethylene oxide condensate having 10 ethylene oxide units in any examples in which Surfactant FW is employed. Any nonionic or anionic surfactant can be used which doesn't precipitate the salt, e.g. magnesium chloride is used.
  • Mykon SF is polyethylene emulsified in water, 30 percent solids.
  • Finish No. 4 is a softener emulsion of a higher fatty acid ester made by Proctor and Gamble. It can be replaced by glycerol monostearate.
  • Appearance ratings are according to the American Association of Textile Chemists and Colorists (AATCC) Test Method 88-A-l964T-Procedure lll C-l wherein l is the poorest appearance.
  • EXAMPLE l The procedure employed was to pad the aqueous mixture on the white twill cotton fabric (8 oz./sq. yd.), dry at 270 F. for 4 minutes and evaluate for wash-wear properties. The appearance, shrinkage, nitrogen and formaldehyde were measured afier five home launderings. All of the mixes had a pH between 2.4 and 2.8. Under each mixture number is the parts of carbamate employed.
  • the mix was prepared as follows. 50 gallons of water was heated to 160 F. Then the trisodium phosphate decahydrate was dissolved therein. The paraformaldehyde was added at 160 F. The mixture was diluted to 100 gallons and then the monosodium phosphate, sodium bisulfite. dimethyl sulfone. methyl carbamate, glycolic acid. magnesium chloride. Sutro l70-D added in order with stirring. The mixture was diluted to 180 gallons and temperature brought to l00l 10 F. Surfactant FW, Mykon SF and Proctor and Gamble Finish No. 4 was added with stirring. The mixture was diluted to 200 gallons.
  • the mixture is applied to the fabric and the fabric dried at a frame temperature of about 330 F.
  • the fabric temperature is about 240280 F.
  • the amount of formaldehyde fixed was about 0.8 percent.
  • EXAMPLE 3 The procedure of example 2 was repeated using polyethylene terephthalate/cotton blend (50:50) sheeting. The amount of paraformaldehyde was reduced to 60 pounds (3.3 percent) but all other components were unchanged except for the use of slightly more water to bring the mix to 200 gallons.
  • EXAMPLE 4 65 percent polyester (polyethylene terephthalate) 35 percent cotton broadcloth shirting fabrics were passed through the following mix in which percentages are by weight of the total mix.
  • Borax 0.5% Sodium bisulfitc 1.5% Zinc fluoboratc 1.0% Ethylene oxide condensate 0.25% (wetting agent) Fatty ester dispersion 3.0% (softener) Water balance
  • the fabric was padded through the mix and dried in a tenter dryer. Conditions for this application were Dryer temperature 250-260 F. Operating speed 1 10 yards/min. irri dwell time in drying 14 seconds Fabric temperature at the F.
  • exit end of the dryer 1 Indicates the sample was pressed in a garment press for 15 seconds including 5 seconds steaming, 5 seconds.
  • samples contained I00 grams of 10 percent methyl carbamate in water and I08 grams of 37 percent aqueous formaldehyde. All samples also contained sufficient water to make the samples up to i000 grams. Samples 1-15 contained 32 grams of 30 percent magnesium chloride and sample 22 contained 28 grams of 30 percent magnesium chloride.
  • Samples 16-19 contained 28 grams of 30 percent magnesium vacuum ex rac ion.
  • Samples 16-19 contained [5 grams of zinc nitrate Shms were ade from. Samples 2A and m bemg hexahydrate, samples 20 and 2i contained 120 grams ofS perlaundered 50 times the shirts were analyzed for nitrogen and cent aqueous zinc fluoborate p 1 21 comained 76 formaldehyde.
  • EXAMPLE 7 The following formulations were made and the bufi'ered A series of i8 samples were prepared using the formulations solutions prepared were padded on 65 percent polyester, 35 in the table- The Solutions made P to 2,000 grams were percent cotton twill fabric and dried at 350 F. for 1.5 5 padded n 67 p r n viscose r y 33 p r n cotton minutes. tablecloth fabric and dried at 350 F.
  • EXAMPLE 12 A series of eight mixes were prepared and 50 percent polyester, 50 percent cotton sheeting padded there through at room temperature and dried at 330 F. for 1 minute.
  • Each mix contained 80 grams of 10 percent monosodium phosphate, 40 grams of percent trisodium phosphate, 200 grams of percent sodium bisulfite, grams of dimethyl sulfone, 216 grams of 37 percent formaldehyde, 120 grams of 50 percent Sutro l70 D l00 grams of 10 percent glycolic acid, 56 grams percent magnesium chloride, 50 grams of 10 percent Surfactant FW, 20 grams of carbamate and water to make 2,000 grams.
  • the carbamates employed were as follows: (1) methyl carbamate, (2) ethyl carbamates, (3) N-ethyl methyl carbamate, (4) N-ethyl ethyl carbamate, (5) N-butyl carbamate, (6) hydroxyethyl carbamate, (7) hydroxypropyl carbamate, (8) hydroxypropyl-hydroxyethyl carbamate mixture. Except for the mix pH all tests were after 5 home launderings. The results are set forth below.
  • a series of mixes were prepared and 50 percent polyester, 50 percent cotton sheeting padded there through at room temperature and dried at 330 F. for 1 minute.
  • Each mix contained 80 grams of 10 percent monosodium phosphate. grams of 5 percent trisodium phosphate, 20 grams of dimethyl carbamate, 216 grams of 37 percent formaldehyde, 120 grams of percent Sutro-l70-D, 100 grams of 10 percent glycolic acid, 56 grams of 30 percent magnesium chloride, 50 grams of 10 percent surfactant solution, 10 percent sodium bisulfite and 10 percent dimethyl sulfone (DMS0 in the amounts in grams set forth below and water to make 2,000 grams.
  • DMS0 dimethyl sulfone
  • EXAMPLE 14 acid, 56 grams of 30 percent magnesium chloride, 120 grams of 50 percent Sutro l70-D, the indicated amounts of 10 percent dimethyl sulfone and cold water sufficient to make 2,000 grams.
  • the mix was padded on sheeting which was 50 percent cotton-50 percent Dacron (polyethylene terephthalate) at room temperature and dried at 350 F. in an oven for 1 minute. The results are shown in the following table. The percent shrinkage and percent formaldehyde were measured after five launders.
  • EXAMPLE 18 The purpose of this experiment was to determine the minimum level of formaldehyde in the mix to yield 1 percent formaldehyde fixation.
  • the mixes prepared were padded on 50 percent Dacron50 percent viscose rayon sheeting. All of TABLE 24 5% trlsodlum 10% Percent Percent phosphate N8H2PO4 pH shrinkage CH1O Fabric pH 40 80 2. 1 0. 67 0. 48 5. 42 60 120 2. 3 1. 11 0. 45 e 20 80 160 2. 5 1. 17 0. 40 6. 10 100 200 2. 6 1. 05 0. 41 e 31 100 2. 4 1. 22 0. 48 6.00 150 75 2. 5 1. 11 0. 44 6. 68 200 100 2. 7 l. 17 0. 41 6. 72 250 125 3.0 1. 17 0. 40 6.
  • Each mix contained Puraformaldehyde e0 e0 60 80 grams of 5 percent trisodium phosphate, the indicated PlmsPhc amount of paraforrnaldehyde, 100 grams of 10 percent f f 1 monosodium phosphate, 150 grams of 10 percent sodium Glycolic acid .00 200 200 302 Magnesium chloride 1 l2 bisulfite, 5 grams of dimethyl sulfone, 20 grams of methyl car- 1" 1 50 bamate, 150 grams of 10 percent glycolic acid, 67 grams of 30 2g: g no as percent magnesium chloride, 120 grams of 50 percent Sutro 1; swam, Fw 50 50 50 170 D, 40 grams of 10 percent Surfactant FW, 48 grams of Methyl carbamate 40 40 40 40
  • the mix pH and fabric pH were determined as well as percent shrinkage and percent formaldehyde afier 5 launders. The results are shown below.
  • R and R are selected from the group consisting of hydrogen, alkyl and carbocyclic aryl and R is selected from the group consisting of alkyl, carbocyclic aryl, hydroxy lower alkyl and lower alkoxy lower alkyl and (3) glycolic acid.
  • the improvement comprising including in the aqueous mixture a buffer to counteract the tendency of the cellulosic material impregnated with said mixture to become highly acidic on standing.
  • treating solution includes a water soluble salt of a polyvalent metal capable of catalyzing the reaction between cellulose and formaldehyde.
  • the buffer includes an alkali metal phosphate
  • the aqueous mixture includes alkali metal bisulfite in an amount sufficient to reduce formaldehyde odor and also includes dimethyl sulfone in an amount ofO.l to 5 percent to raise the pH.
  • a process according to claim 6 wherein the phosphate comprises trisodium phosphate.
  • aqueous mix also contains mannitol as a formaldehyde scavenger and sodium bisulfite to reduce the formaldehyde odor.
  • aqueous mix also contains sugar alcohol of the group consisting of pentitols, hexitols and hepitols as a formaldehyde scavenger.
  • a process according to claim 18 wherein the treating mixture comprises 0.1 to 0.75 percent trisodium phosphate calculated as the decahydrate, 1.5 to 15 percent formaldehyde, 0.1 to 1 percent monosodium phosphate, sodium bisulfite in an amount of 0.25 percent to not more than l part for each two parts formaldehyde, 0.1 to 5 percent of the carbamate, 0.1 to 1.5 percent of glycolic acid.
  • a process according to claim 1 comprising treating a cellulose fabric with an aqueous mixture of l formaldehyde, (2) methyl carbamate or ethyl carbamate, glycolic acid and an alkali metal phosphate buffer.
  • a process according to claim 23 wherein the ratio of monosodium phosphate to trisodium phosphate is between 1:1 and 10:1.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
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US762366A 1968-09-16 1968-09-16 Buffered aldehyde fixation composition Expired - Lifetime US3622261A (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US76236668A 1968-09-16 1968-09-16
GB3386771 1971-07-20
DE19712138503 DE2138503C3 (de) 1971-08-02 Verfahren zum Fixieren von Formaldehyd auf Cellulosefasern und -geweben
NL7111687A NL7111687A (de) 1968-09-16 1971-08-25
LU63774 1971-08-25
FR7130916A FR2151211A5 (de) 1968-09-16 1971-08-26
BE772122A BE772122A (fr) 1968-09-16 1971-09-03 Fixation d'aldehyde sur matieres cellulosiques (

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US (1) US3622261A (de)
BE (1) BE772122A (de)
FR (1) FR2151211A5 (de)
GB (1) GB1349542A (de)
LU (1) LU63774A1 (de)
NL (1) NL7111687A (de)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3807952A (en) * 1971-10-08 1974-04-30 Raduner & Co Ag Method of crosslinking cellulosic fibres
US4182735A (en) * 1978-05-25 1980-01-08 International Paper Company Production of high crimp, high strength, hollow rayon fibers
US4242411A (en) * 1978-05-25 1980-12-30 International Paper Company High crimp, high strength, hollow rayon fibers
US4254005A (en) * 1980-02-06 1981-03-03 The United States Of America As Represented By The Secretary Of Agriculture Abrasion resistance and strength of cotton-containing fabric made resilient with N-methylolacrylamide-type reagent
US4255149A (en) * 1979-01-31 1981-03-10 The United States Of America As Represented By The Secretary Of Agriculture Abrasion resistance and strength of cotton-containing fabric made resilient with N-methylolacrylamide-type reagent
US4277243A (en) * 1979-01-31 1981-07-07 The United States Of America As Represented By The Secretary Of Agriculture Process for producing durable-press cotton fabrics with improved balances of textile properties
US4289673A (en) * 1979-01-31 1981-09-15 The United States Of America As Represented By The Secretary Of Agriculture Process for producing durable-press cotton fabrics with improved balances of textile properties
US4314806A (en) * 1980-09-08 1982-02-09 Basf Aktiengesellschaft Textile finish and processes for its preparation and use
US4447241A (en) * 1982-04-12 1984-05-08 Springs Industries, Inc. Oxidative afterwash treatment for crease resisting fabrics
EP0767231B1 (de) * 1995-10-06 2001-12-05 Basf Corporation Verfahren zur Herstellung einer Carbamat- oder Harnstoff-funktionellen Verbindung
US6437212B1 (en) * 2000-10-27 2002-08-20 Kimberly-Clark Worldwide, Inc. Reduced odor absorbent article and method
US20030114806A1 (en) * 2000-10-27 2003-06-19 Jeffrey Mark La Fortune Odor control absorbent article and method
DE19824656B4 (de) * 1997-05-29 2007-02-15 Huntsman Petrochemical Corp., Austin Verfahren zur Herstellung von Hydroxylalkylcarbamaten
CN110951310A (zh) * 2018-09-26 2020-04-03 万华化学（北京）有限公司 氨基甲酸酯类化合物作为有机溶剂的用途

Citations (2)

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Publication number Priority date Publication date Assignee Title
US3196036A (en) * 1960-08-08 1965-07-20 West Point Pepperell Inc Process for controlling undesirable aldehyde and amine odors in treated textile material
US3420696A (en) * 1964-06-02 1969-01-07 West Point Pepperell Inc Aldehyde fixation on polymeric material

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3196036A (en) * 1960-08-08 1965-07-20 West Point Pepperell Inc Process for controlling undesirable aldehyde and amine odors in treated textile material
US3420696A (en) * 1964-06-02 1969-01-07 West Point Pepperell Inc Aldehyde fixation on polymeric material

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Hobart et al., Textile Research Journal, Vol. 38, pp. 824 830 (1968) *
Sakar et al., Textile Research Journal, Vol. 38, pp. 1145 1146 (1968) *

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3807952A (en) * 1971-10-08 1974-04-30 Raduner & Co Ag Method of crosslinking cellulosic fibres
US4182735A (en) * 1978-05-25 1980-01-08 International Paper Company Production of high crimp, high strength, hollow rayon fibers
US4242411A (en) * 1978-05-25 1980-12-30 International Paper Company High crimp, high strength, hollow rayon fibers
US4255149A (en) * 1979-01-31 1981-03-10 The United States Of America As Represented By The Secretary Of Agriculture Abrasion resistance and strength of cotton-containing fabric made resilient with N-methylolacrylamide-type reagent
US4277243A (en) * 1979-01-31 1981-07-07 The United States Of America As Represented By The Secretary Of Agriculture Process for producing durable-press cotton fabrics with improved balances of textile properties
US4289673A (en) * 1979-01-31 1981-09-15 The United States Of America As Represented By The Secretary Of Agriculture Process for producing durable-press cotton fabrics with improved balances of textile properties
US4254005A (en) * 1980-02-06 1981-03-03 The United States Of America As Represented By The Secretary Of Agriculture Abrasion resistance and strength of cotton-containing fabric made resilient with N-methylolacrylamide-type reagent
US4314806A (en) * 1980-09-08 1982-02-09 Basf Aktiengesellschaft Textile finish and processes for its preparation and use
US4447241A (en) * 1982-04-12 1984-05-08 Springs Industries, Inc. Oxidative afterwash treatment for crease resisting fabrics
EP0767231B1 (de) * 1995-10-06 2001-12-05 Basf Corporation Verfahren zur Herstellung einer Carbamat- oder Harnstoff-funktionellen Verbindung
DE19824656B4 (de) * 1997-05-29 2007-02-15 Huntsman Petrochemical Corp., Austin Verfahren zur Herstellung von Hydroxylalkylcarbamaten
US6437212B1 (en) * 2000-10-27 2002-08-20 Kimberly-Clark Worldwide, Inc. Reduced odor absorbent article and method
US20030114806A1 (en) * 2000-10-27 2003-06-19 Jeffrey Mark La Fortune Odor control absorbent article and method
US6867343B2 (en) 2000-10-27 2005-03-15 Kimberly-Clark Worldwide, Inc. Odor control absorbent article and method
CN110951310A (zh) * 2018-09-26 2020-04-03 万华化学（北京）有限公司 氨基甲酸酯类化合物作为有机溶剂的用途
CN110951310B (zh) * 2018-09-26 2022-07-12 万华化学（北京）有限公司 氨基甲酸酯类化合物作为有机溶剂的用途

Also Published As

Publication number Publication date
NL7111687A (de) 1973-02-27
BE772122A (fr) 1972-03-03
DE2138503A1 (de) 1973-03-01
DE2138503B2 (de) 1975-06-26
FR2151211A5 (de) 1973-04-13
LU63774A1 (de) 1972-01-05
GB1349542A (en) 1974-04-03

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