US3811131A - Durable press process for treating cellulosic material with methylolamides and acetic acid or formic acid vapors - Google Patents
Durable press process for treating cellulosic material with methylolamides and acetic acid or formic acid vapors Download PDFInfo
- Publication number
- US3811131A US3811131A US00238983A US23898372A US3811131A US 3811131 A US3811131 A US 3811131A US 00238983 A US00238983 A US 00238983A US 23898372 A US23898372 A US 23898372A US 3811131 A US3811131 A US 3811131A
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- United States
- Prior art keywords
- fabric
- percent
- cotton
- acetic acid
- crosslinking
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title claims abstract description 69
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 235000019253 formic acid Nutrition 0.000 title claims abstract description 30
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 239000000463 material Substances 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims description 42
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical class NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 title description 4
- 239000004744 fabric Substances 0.000 claims abstract description 103
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 30
- 238000004855 creaseproofing Methods 0.000 claims abstract description 28
- 230000037303 wrinkles Effects 0.000 claims abstract description 27
- 229920000742 Cotton Polymers 0.000 claims abstract description 25
- 239000007864 aqueous solution Substances 0.000 claims abstract description 16
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical group OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000001035 drying Methods 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims description 18
- 238000004132 cross linking Methods 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 17
- ZEYUSQVGRCPBPG-UHFFFAOYSA-N 4,5-dihydroxy-1,3-bis(hydroxymethyl)imidazolidin-2-one Chemical compound OCN1C(O)C(O)N(CO)C1=O ZEYUSQVGRCPBPG-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000012808 vapor phase Substances 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 230000001143 conditioned effect Effects 0.000 claims description 4
- 230000003750 conditioning effect Effects 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims 1
- 239000000835 fiber Substances 0.000 abstract description 12
- 238000005470 impregnation Methods 0.000 abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 238000011084 recovery Methods 0.000 description 22
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 21
- 229940013688 formic acid Drugs 0.000 description 20
- 230000014759 maintenance of location Effects 0.000 description 20
- 238000005299 abrasion Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- ZHXAZZQXWJJBHA-UHFFFAOYSA-N triphenylbismuthane Chemical compound C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 ZHXAZZQXWJJBHA-UHFFFAOYSA-N 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- -1 polyacrylonitrite Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- 150000007974 melamines Chemical class 0.000 description 4
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 229920001903 high density polyethylene Polymers 0.000 description 3
- 239000004700 high-density polyethylene Substances 0.000 description 3
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- LGSKBXPWZKTEAX-UHFFFAOYSA-N bis(hydroxymethyl)carbamic acid Chemical compound OCN(CO)C(O)=O LGSKBXPWZKTEAX-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000004900 laundering Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229950005308 oxymethurea Drugs 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- IMTKRLUCQZWPRY-UHFFFAOYSA-N triazine-4-carbaldehyde Chemical compound O=CC1=CC=NN=N1 IMTKRLUCQZWPRY-UHFFFAOYSA-N 0.000 description 2
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical class NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 1
- GHGFADYXERRLID-UHFFFAOYSA-N NC(=O)N.C(O)C(=CO)O Chemical compound NC(=O)N.C(O)C(=CO)O GHGFADYXERRLID-UHFFFAOYSA-N 0.000 description 1
- XZAQBIOYFWCYIP-UHFFFAOYSA-N NC(=O)N.OC=CO Chemical class NC(=O)N.OC=CO XZAQBIOYFWCYIP-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000007730 finishing process Methods 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical group NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- WTXWKVALMHMPRJ-UHFFFAOYSA-N prop-1-ene;urea Chemical class CC=C.NC(N)=O WTXWKVALMHMPRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- PUNUCLJJWUUKFB-UHFFFAOYSA-N s-ethyl n-cyclohexylcarbamothioate Chemical compound CCSC(=O)NC1CCCCC1 PUNUCLJJWUUKFB-UHFFFAOYSA-N 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—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
-
- 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
-
- 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
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/04—Polyester fibers
-
- 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
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/09—Polyolefin
-
- 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
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/10—Polyvinyl halide esters or alcohol fiber modification
-
- 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
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/21—Nylon
Abstract
The dimensional stability, wrinkle resistance, smooth drying characteristics and total shape retentivity of cellulosic materials such as cotton fabrics are improved by treatment with acetic acid or formic acid vapors after impregnation of the materials with an aqueous solution of a water-soluble creaseproofing agent containing reactive N-methylol groups such as trimethylolmelamine or DHDMEU, whereby the cellulosic fibers become crosslinked.
Description
United States Patent [191 Gamarra et a1.
[451 May 21, 1974 I DURABLE PRESS PROCESS FOR TREATING CELLULOSIC MATERIAL WITH METHYLOLAMIDES AND ACETIC ACID OR FORMIC ACID VAPORS [75] Inventors: Jose P. Gamarra, San Jose; Ronald Swidler, Palo Alto; Katherine W. Wilson, Newport Beach, all of Calif.
[73] Assignee: Cotton, Incorporated, New York,
[22] Filed: Mar. 28, 1972 [21] Appl. No.: 238,983
Related U.S. Application Data [63] Continuation-in-part of Ser. No. 762,119, Sept. 24,
1968, Pat. NO. 3,653,805.
[52] U.S. C1 2/243 R, 8/1 15.6, 8/115.7, 8/129, 8/182, 8/183, 8/185, 8/186, 8/187,
8/D1G. 4, .8/D1G. 9, 8/D1G. 10, 8/D1G. 21,
[51] Int. Cl. D06m 1/16, D06m 15/56, D06m 15/58 [58] Field of Search 8/116.3, 149.1, 149.3, 8/186, 185, 183, 182, 187; 38/144; 2/243 [5 6] References Cited UNITED STATES PATENTS 2,235,141 3/1941 Dreyfus et a1. 8/1 16.3 2,441,859 5/1948 Weisberg et a1. 8/116.4 3,310,363 3/1967 Russell et a1 8/1 16.4 3,647,353 3/1972 Calzaferri et a1. 8/116.3 3,653,805 4/1972 Gamarra et a1 8/116.3 3,706,526 12/1972 Swidler et a1. 8/1164 FOREIGN PATENTS OR APPLICATIONS 437,642 11/1935 Great Britain 8/116.3 1,359,102 3/1964 France 8/116.3
OTHER PUBLICATIONS Prett, Melliand Textiberichte, 46(1) 73-74 (1965).
Primary Examiner-George F. Lesmes Assistant Examiner.l. Cannon Attorney, Agent, or Firm-Peter H. Smolka 57 ABSTRACT The dimensional stability, wrinkle resistance, smooth drying characteristics and total shape retentivity of cellulosic materials such as cotton fabrics are improved by treatment with acetic acid or formic acid vapors after impregnation of the materials with an aqueous solution of a water-soluble crease-proofing agent containing reactive N-methylol groups such as trimethylolmelamine or DHDMEU, whereby the cellulosic fibers become crosslinked.
9 Claims, No Drawings 1 DURABLE PRESS PROCESS FOR TREATING CELLULOSIC MATERIAL WITH METHYLOLAMIDES AND ACETIC ACID OR FORMIC ACID VAPORS CROSS-REFERENCE This application is a continuation-in-part of Ser. No. 762,119, which was filed Sept. 24, 1968 and is now U.S. Pat. No. 3,653,805.
BACKGROUND OF THE INVENTION contribution to the cotton finishing art, the results have been far from perfect. For instance, in some cases the formaldehyde crosslinking treatment has tended to lack reproducibility, since control of the formaldehyde crosslinking reaction heretofore has been difficult. When high. curing temperatures were used with an acid or potential acidcatalyst, overreaction and degradation However, While formaldehyde has made a significant Another more specific object is to provide a process for crease-proofing cotton or other cellulosic materials using a water-soluble crease-proofing agent containing reactive N-methylol groups which permits the cure of the treated material to be safely delayed for long or indefinite periods until after completion of desired articles therefrom including, for instance, the cutting, sewing and pressing of garments.
Another specific object is to provide a creaseproofing process for use with cellulosic materials which produces good wrinkle recovery and smooth drying characteristics, keeps loss of tensile strength and abrasion resistance to a minimum, gives good laundering life and chlorine resistance, employs simple reactants and, if desired, can produce a pre-treated fabric which is relatively insensitive to surrounding conditions and has virtually infinite shelf life prior to final cure.
It is further an object of this invention to provide a process for treating cellulosic materials with an acidic catalyst in the vapor phase without the degrading characteristics of strong mineral acids such as hydrochloric acid.
These and other objects, as well as the scope, nature, and utilization of the invention will become more clearly apparent from the following more detailed description. Unless otherwise indicated, all proportions and percentages of materials or compounds are expressed on a weight basis throughout this specification and appended claims.
In accordance with the present invention, a process is provided for improving the dimensional stability,
' wrinkle resistance, smooth drying characteristics and of the cotton often happened which considerably impaired its strength. On the other hand, when attempts were made to achieve reproducibility at temperatures of 50C. or less, much longer reaction or finishing times were usually required. rendering the process economically relatively unattractive. See for example, British Patent 980,980. In other cases, formaldehyde crosslinking has not been able to meet commercial standards with respect to dry wrinkle recovery. For these and similar reasons, efforts have been continuing to develop new and better cellulosic and cotton finishing processes.
The use of an atmosphere containing hydrochloric acid to catalyze crosslinking between a crease-proofing agent and a cellulosic fabric material in which the agent is impregnated has been suggested in the prior art. Control of such a reaction is difficult but important since the strong mineral acid catalyst may degrade the fabric itself. Hydrochloric acid-catalyzed fabric materials also have been found to have low tensile strength properties, particularly if the crosslinked fabric is post-heated.
SUMMARY OF THE INVENTION Accordingly, a primary object of the present invention' is to provide a practical process for treating cellulosic materials with a suitable crease-proofing agent which process substantially prevents or alleviates the problems mentioned above.
A more specific object has been to develop a process for crosslinking cotton with the aid of a water-soluble crease-proofing agent containing reactive N-methylol groups, using an acid catalyst used in the vapor phase, so as to keep fiber injury to a minimum.
total shape 'retentivity of a cellulosic fiber-containing fabric which comprises: (a) applying to the fabric an aqueous solution of a water-soluble crease-proofing agent containing reactive N-methylol groups; and (b) heating the impregnated fabric containing the watersoluble crease-proofing agent containing reactive N- methylol groups in a non-reactive vapor atmosphere containing a catalyst selected from the group consisting of formic acid and acetic acid to a temperature De tween above C. up to about C. for a time of between about l0 seconds and 2 hours until the cellulose fibers become effectively crosslinked.
The process requires relatively short reaction times and gives high wrinkle recoveries while at the same time producing satisfactory tensile and tear strengths.
The process of the present invention has substantial advantages of use as compared with typical prior art processes such as hydrochloric acid vapor-catalyzed durable press systems. For example, the process of the DESCRIPTION OF PREFERRED EMBODIMENTS In the embodiment disclosed and claimed herein, the cotton or cellulose-containing fabric is impregnated with an aqueous solution containing about I to about 40 percent, preferably from about 2 to about 20 percent, most preferably from about 5 to l5 percent, of a water-soluble crease-proofing agent containing reactive N-methylol groups to give a wet pick-up of between about 50 and about 100 percent, preferably from about 60 to about 90 percent, most preferably from about 65 to 85 percent, based on dry fabric weight.
The present invention is useful for treating various natural or artificial cellulosic fibers alone or as mixtures with each other in various proportions or as mixtures with other fibers. Such natural cellulosic fibers include cotton, linen and hemp, and regenerated or an tificial cellulosic fibers useful herein include, for example, viscose rayon and cuprammonium rayon. Other fibers which may be used in blends with one or more of the above-mentioned cellulosic fibers are, for example, cellulose acetate, polyamides, polyesters, polyacrylonitrite, polyolefins, polyvinyl chloride, polyvinylidine chloride and polyvinyl alcohol fibers. Such blends preferably include at least about 20 percent by weight and most preferably at least about 40 percent by weight, of cotton or other cellulosic fibers.
The fabric may be knit, woven or non-woven, or be any otherwise constructed fabric. The fabric may be flat, creased, pleated, hemmed or sewn or otherwise formed to produce an article such as a garment of any desired shape prior to contact with the acetic acid or formic acid catalyst-containing atmosphere. After processing, the formed crosslinked fabric will maintain substantially the original configuration 'forthe life of the article, that is, a wash-wear or durable press fabric will be produced.
The crease-proofing agents useful herein include particularly the easily hardenable precondensates which are substantially water soluble and are obtained by condensation of formaldehyde with a compound such as a lower alkyl substituted melamine, a urea, or a phenol such as resorcinol. As is well known in the resin treating art, these precondensates are capable of being applied to the cellulosic material from an aqueous solution. Triazines obtained by condensing a lower alkyl substituted melamine and formaldehyde are examples of such precondensates. Good results are obtained, for instance, using precondensates obtained by condensing 1 mole of melamine or an alkyl substituted melamine with 2 to 6 moles of formaldehyde, i.e., using di-, trior hexamethylol melamine. Commercially available products of this kind include Aerotex 23, a triazineformaldehyde, precondensate; Aerotex M-3, a melamine-formaldehyde condensate; Aerotex P-225, hexakis-(methoxymethyl) melamine; and Aerotex 19, which is a less completely fractionated modification of Aerotex P-225. These products are supplied in the form of aqueous solutions by American Cyanamid Company.
Other suitable creaseproofing agents include products such as dihydroxydimethylolethyleneurea, DHDMEU, available as Permafresh 183 or in a somewhat modified, less reactive form as Permafresh 113B from Sun Chemical Company, as well as modified propylene urea compounds such as Fixapret PCL, available from Badische Anilin und Soda-Fabrik. Compounds having at least 1% moles of formaldehyde combined as methylol formaldehyde with a cyclic urea or cyclic propylene urea are suitable and the dimethylol derivatives are preferred. However, it is similarly feasible to use other known crease-proofing agents such as N-methylol carbamates and methylol urea compounds.
.reactive atmosphere is performed at a temperature of 4 Pretreatment of the cloth, prior to the vapor phase catalytic treatment, with polymeric resinous additives that form soft films, such as conventional dispersions or latexes, can result in an unusually great incremental improvement in wrinkle recovery of the treated fabric. Polymer additives can also improve the flex abrasion resistance and tear strength, or alter the ratio of dry wrinkle recovery to wet wrinkle recovery, or in some instances shorten the reaction time needed to produce an acceptable durable press fabric. Polymeric additives suitable for such purposes are, in most cases, available commercially in concentrated aqueous latex form, and it is desirable to dilute these to a concentration of l to 10 percent polymer before padding onto the fabric. Suitable polymeric additives include solid resinous or rubbery acrylonitrile-butadiene copolymers and mixtures containing the same with various vinyl resins; polyethylene; deacetylated copolymers of ethylene-and vinyl acetate; polyurethanes and various polymers of alkyl acrylates, other polyesters and polyamides. g The impregnated fabric may be dried or conditioned to a moisture content of from about 2 up to about 100, preferably from about 3 to about percent by weight of the dry cellulosic fabric material. The impregnated fabric may thus be catalyzed in a condition ranging from about essentially dry to about essentiallywet condition.
The fabric is then passed into a non-reactive, catalyzing atmosphere containing a catalytically effective amount of formicacid or acetic acid which may be obtained from any convenient source. In addition to the catalyst, the treating atmosphere may contain inert .gases such as air, nitrogen, carbon dioxide, helium, steam and the like. The treating atmosphere is nonreactive in that it contains the gaseous catalyst and an inert gas. Gaseous materials or monomers that could react, condense or polymerize with the fabric or methylolamide crease-proofing agent should not be present in the treating atmosphere.
The non-reactive atmosphere can contain up to about 100, often from about 5 to volume percent acetic acid or formic acid, balance, (if any) inert gas.
Contact of theconditioned fabric with the nonfrom about 80 and 160C, preferably from about C. to about 140C. most preferably from about 1 10C. to about C., for atime of between about 10 seconds and 2 hours, preferably from about 1 to about 20 minutes, most preferably from about 2 to about 15 minutes.
Any suitable means to contact the fabric with the gaseous acetic acid orformic acid catalyst may be employed. For example, a batch system utilizing a closed vessel or tube containing the gaseous catalyst may be used into which the conditioned, crease-proofing agent-containing fabric may be placed and there exposed to the treating atmosphere for the appropriate time. In the alternative, a dynamic or continuous system can be used such as one wherein a gas stream containing acetic acid or formic acid catalyst, is passed through a closed elongated chamber through which the impregnated fabric or articles are also passed at an appropriate rate, either concurrently or countercurrently relative to the gas. It is also possible to use combinations of the above, that is, such as by passing a stream of the catalyst-containing atmosphere over a stationary fabric.
The crosslinked fabric is thereafter desirably heated to a temperature above about 100C., e.g., in the range of from about 100 to 180C, preferably from about 140C. to about '1 6090, to volatilize and remove water; vapor, residual catalyst and any unbound, volatile, crease-proofing agent. In addition, this heating step further cures the crosslinked fabric thus improving its durability to laundering as well as improving the duration press characteristics of the treated fabric. This heating and curing step may also allow a-reduction in the time of exposure to the gaseous catalyst-containing atmosphere without sacrificing durable press performance.
Heating the crosslinked fabric may advantageously be performed in any suitable fabric heating chamber.
The temperature of the post-heating 'step can be re-, duced or the post-heating step entirely eliminated without impairing wash-wear performance by using creaseproofmg agents more reactive than dihydroxydimethylolethyleneurea. These fabrics containing the more an insulating lank et. the gas content of the reactor is recirculated through an externalrecycle line byan aluminum pressure blower equipped with a heat slinger and high-temperature. lubricated sealed-bearings. An adjustable damper in the recycle line permits some control of the pressure within .the reactor, but during normal operation nearly atmospheric reactor pressure is preferred.
, This reactor was fitted with aluminum tubing through which a solution containing 85 percent by weight of formic acid is poured to fall onto an evaporating dish in' the bottom of the reactor. Substantially all of thevapors in the reactor'are in each of the following Examples'formic acid vapors evaporated from the evaporatingdish. Some water vapor is also present. The acetic acid and hydrochloric acid atmospheres in the Examples are provided in the same manner. 1
. EXAMPLE 1 v Cotton twill fabric samples and trouser cuffs were padded to 70 percent wet pickup with aqueous solu-' tions containing the amounts of crease-proofing agent and. polymeric additive shown in Table l. Creasereactive crease-proofing agents may be neutralized with a slightly alkaline solution (such as a l percent solution of sodium carbonate) and washed to remove all traces of catalyst or unbound crease-proofing agent.
The invention is additionally illustratedin connection with the following examples which are to be considered as illustrative of the present invention. It should be understood, however, that the invention is not limited to the specific details of the Examples.
EXAMPLES The reactor used in this work was a cylindrical vesselhaving a capacity of about 71 liters, constructed'of S's-inch aluminum (42 cm. inside-diameter and 57 cm. high). The walls of this reactor are heated with band heaters equipped with a three-way switch which permits operation at 600, 1,200 or 2,400 watts. The reactor wall temperature is controlled by an adjustable bimetallic thermostat, and the reactor is surrounded by proofing agents included trimethylolmelamine (Resloom HP, Monsanto Chemical 'Co.), methylated methylolmelaminetResloom M-75, Monsanto Chemical Co. amixed amide product including a methylolmelamine (Aerotex 23,American Cyanamid Co.) and di'-.
methylol dihydroxyethylene urea (Permafresh 183,
Sun Chemical Co.). Polymeric additives included polyethylene (Mykon SF), and an acrylic resin"(Rhoplex K-87). After impregnation, fabric samples 'were dried to moisture content of about 7-10 percent, exposed to formic acid vapor in the reaction chamber described above at about 115C. for various reaction times, washed, dried, and tested.
The tabulated data show that high levels of wrinkle recovery were achieved in all cases. Generally, shorterreaction times were necessary and higher tensile strength retentions recorded, when the melamine derivatives were used, which are more polymerizablethan the dihydroxyethylene urea derivative.
TABLE I-A Stoll HCO l-l Wrinkle Recovery Angle Tearing Flex Exposure Total (degrees) Strength Abrasion, Run Pad Bath Composition Time Add-On Warp (grams) Warp No. Methylol f Softener (min) Dry Wet Dry Wet Warp 7 Fill (cycles) Compound v 15% 1 Resloom M- 2% Mykon SF 5 2.4% 146 139 117 2420 1580 550 2 4 2.7 154 142 111 2090 1660 445 3 3 2.8 146 139 126 119 2620 1670 670 4 2 3.0 131 124 124 111 2820 1880 660 0% 5 Aerotex 23 3% Rhoplex K-87 4 I 7.6 149 148 128 136 1740 1020 580 6 3 7.9 148 147 126 132 1810 1100 560 7 2 8.7 148 150 132 136 1740 1080 460 8 1% 8.6 142 142 122 2120- 1180 520 9% a 9 Permafresh 183 2% Mykon SF 5 146 136 118 129 2860 1660 I 1550 10 10 144 114 122 2620 1780 1180 11 12% 144 140 119 132 2600 1570 730 12 15 148 139 126 128 2440 1620 680 13 n,a. n.a. n.a n.a. 90 84 82 v 4240 2780 620 [1.1L not applicable.
a. methylated methylolmelamine b. a misture of dimethylolurea and trimethylolmelamine c. dihydroxydimethylolethyleneurea TABLE l-C; Cohtinued "'Tasn btogzat? 'wiiiii"" Warp Fill Ratings Number of Work to Extension Tensile Work to Extension Tensile Tumble Dried Line Dried Wash-Dry Run Rupture at Break Strength Rupture at Break Strength Wash- Crease Wash- Crease Cycles No. (in.-lb) (lb) (in.-1b) (lb) Wear Retention Wear Retention to Holes Properties After 1 Washing 1 21.4 14.8 148 13.2 19.0 88 3% 4% 3% 4 2 21.0 14.0 151 10.9 17.1 82 4 4 4 3 16.2 12.4 135 7.7 16.2 66 4 5 3% 4 4 16.5 12.2 136 8.9 16.8 72 4 5 4 4 Properties Afler Washings 5 23.7 16.6 141 12.5 18.0 82 3% 3% 3 3 20 6 22.1 15.2 138 11.3 16.4 79 3% 4 3 A 4 18,20 7 17.5 13.4 128 9.8 16.0 72 4 4 4 4 10,12 8 19.4 13.7 132 7.5 15.4 61 4 4 4 4 11,14
9 29.5 13.7 156 16.1 19.9 86 n.a n.a n.a. n.a n.a
EXAMPLE ll 20 minutes at I 15C., and then heated in air for 5' minutes at 160C. Fabric samples were then washed, dried and t Resu t are hswnin Tabls .11. The tabulated results show that a high degree of useful reaction could be achieved with all crease-proofing agents used. Similarly, good results are achieved using 10 percent (solids) solutions of hexamethoxymethylmelamine, trimethylolmelamine and trimethylolmelaminedimethylolurea.
TABLE 11 Wrinkle Recovery Angle Tearing Stoll Flex Tensile (degrees) Strength Abrasion, Strength Dry Wet (grams) Warp (1b) Methylolamide Warp Fill Warp Fill Warp Fill (cycles) Warp Fill Properties After 1 Washing Dimethy1o1- 154 134 162 139 (a) 1060 550 30 propyleneurea Dimethyloluron 161 134 158 144 (a) 890 190 98 27 Dimethylol- Carbamate 131 147 2390 1520 960 110 46 Trimethylol- Melamine 164 142 154 146 (a) 940 200 105 33 Properties After 10 Washings Dimethylol- 158 130 154 2000 1190 480 98 36 propyleneurea Dimethyloluron 131 158 144 (a) 930 180 93 30 Dimethylolcarbamate 120 109 141 123 2590 1590 940 124 49 Trimethylolmelamine 155 138 158 133 (a) 970 230 104 30 v Untreated (unwashed) 78 71 74 78 3800 2060 640 66 Untreated (Washed) 7O 68 69 72 2840 1630 670 161 74 n.a. not applicable (:1) Fabric specimens tore across filling yarns only. 7
EXAMPLE 111 Samples of the same twill fabric as used in Eitample 11 were impregnated with an aqueous solution containing 9 percent (solids) of Permafresh 1 13B (dimethylol dihydroxyethylene urea) and 2.5 percent (solids) urein Table 111. The samples were then washed, dried and tested. Results are shown in Table 111.
TABLE I11 1 Exposure Heating Time Wrinkle Recovery Angle Tearing Stoll Flex Tensile Time and v and g (degrees) A Strength Abrasion, Strength Gaseous Temperature Temperature Dry 7 V v w Wet (grams) Warp (lb) Catalyst (min/C) (min/C) Warp Fill Warp Fill Warp Fill (cycles) Warp Fill HCOOH 3/115 /160 158 136 152 142 1990 1160 690 105 35 do. 2/115 5/160 150 132 151 134 2050 1270' 530 110 '40 do. 1.5/1'15 5/160 154 129 148 134 2150 1250 560 109 34 do. 1/115 5/160 154 128 148 136 2140 1340 570 112 39 dov 2/115 5/150 148 128 136 124 1900 1130 400 118 42 d0. 2/115 5/140 146 130 .131 122 2030 1200 510 119 45 do. 2/115 5/130 130 120 123 118 2280 1440 700 126 51 CH,COOH 3/115 5/160 131 122 140 130', 1 2440 1430 720 129 44 do. 2/115 5/160 132 124 137 128 2190 1280 670 111 43 do. 1.5/115 5/160 138 122 138 128 2430 1450 660 121 46 do. 1/115 5/160 140 123 138 128v 2410 1350 v650 127 43 um g d 7 8 71 74 78 3800 2060 640 175 66 amassed) v Untreated 70 68 69 72 2840 1630 670 161 74 (washed) These tabulated results show that a short exposure to acetic acid, as well as to formic acid, is sufficient to allow a high level of wrinkle recovery to be achieved after a subsequent heat treatment. The balance of wrinkle recovery gained to strength and abrasion resistance lost is about the same for each catalyst, andcomparable with a conventional pad/dry/cure system using the same crease-proofing agent.
EXAMPLE 1V These results show the advantages of the present inve i n as. swe wqz it hyd qslllqzi s stsm a Prior to the post-heating step, fabrics treated with the hydrochloric acid system showed good degrees of wrinkle recovery angles, but rather low tensile strength retentions. The post-heating step, however. proved to be highly detrimental to the strength of these HCl-system fabrics. As in the case of the Permafresh 1 13B-treated fabrics. the acid degradation was such that it was imposible to measure any of their physical properties. I
To show that post-heating at lower temperatures could yield fabrics with acceptable degrees of strength retention for formic acid but not hydrochloric acid systems, further runs were conducted in which fabrics impregnated with dimethylolurea (Permafresh 477) and urethane Latex-502 were exposed to formic or hydrochloric acid vapors for 5 min. at 120 or C., respec-' tively, and then post-heated at 100140C. The resulting fabric properties are listed in Table 1V-B.
TABLE IV-A Exposure Postheated Wrinkle Recovery Angle, Tensile Strength Wash- Temp. at 150C Add-on W F (degrees), retention) Wear Catalyst (C) for 5 min Dry Wet -Warp Fill Ratings HCOOH 60 No 2.6 146 208 82 97 2.7 do. 80 do. 3.4 150 210 79 98 3.0 do. 100 do. 5.1 223 257 77 3.0 do. 120 do. 5.7 286 270 61 69 4.2 do. 60 Yes 5.2 293 292 56 60 4.4 do. do. 5.4 289 295 53 51 4.4 do. do. 5.4 306 307 54 55 4.3 do. do. 5 5 308 306 52 53 3.9 l-lCl 60 No 258 254 51 62 3.0 do. 80 do. 282 284 37 63 3.0 do. 100 do. 286 290 34 32 3.6 do. 120 do. 305 304 27 16 4.0 do. 60 Yes a a a a a do. 80 do. a a a a a do. 100 do. a a a a a do. 120 do. a a a a a 100 100 Untreated 152 (186 1b) (74 lb) Control Fabrics too weak to test. Neutralized with a 1 percent sodium carbonate solution and washed TABLE IV-B Exposure Postheating Wrinkle Recovery Angle Tensile Strength Wash-Wear Time/Temp Time/Temp W F (degrees) retention) Ratings Catalyst (min/C) (min/C) Dry Wet Warp Fill HCOOH 5/120 5/100 296 284 66 Y 61 4.2 do. do. 5/120 288 281 68 60 4.2 do. do. 5/130 302 297 66 65 4.2 do. do. 5/140 309 294 66 61 4.2
HCl 5/60 5/100 290 296 35 31 3.8 do. do. 5/120 275 304 17 4 3.7 do. do. 5/130 297 309 10 6 4.0 do. do. 5/140 294 304 I 8 3.5
Untreated 152 160 100 100 Control (186 lb) (74 lb) EXAMPLE V ration) to 65 percent wet pickup. The solution also contained percent (solids) of an acrylic emulsion Cotton twill fabric (7.8 ozI/sq. yd., .1. P. Stevens twist (Rhoplex K-14, Rohm and Haas Co.). The impregtwill having 1 12/50 threads per inch) was treated with nated fabric samples were dried, exposed to a formic a 20 percent solution of dihydroxydimethylole- 20 acid or hydrochloric acid atmosphere at varying temthylcneurca (Permafresh 1 138, Sun Chemicals Corpo-. peratures and times.
TABLE V-A HCOOH W Warp Exposure Wrinkle Recovery Angle, Tearing Strength Tensile Strength Stoll Flex Wash- Add-on Time/Temp. W +F, (degrees) retention) Q70 retention) Abrasion(% Wear (min/C) Dry Wet Warp Fill Warp Fill retgntion) Ratings Properties Prior to Post-heating 2.2 l/l20 236(207) 218(201) 155 144 71 82 308 2.0 4.0 5/120 274(224) 264(254) 105 118 68 77 272 2.2 5.0 /120 276(260) 285(270) 98 91 60 63 306 3.0 5.0 /120 281 (262) 280(272) 96 99 62 66 253 2.8 4.9 /120 302(271) 284(282) 91 95 63 65 279 2.4
1.6 l/lOO 190(179) 214(198) 106 114 92 82 185 2.0 2.5 5/100 225(217) 260(255) 96 74 83 162 2.6 5.2 10/100 268(260) 286(278) 76 77 68 67 153 3.2 6.2 15/100 274(264) 295(288) 73 79 65 71 v 151 3.4 6.2 20/100 268(260) 280(278) 73 75 65 65 156 3.3
mum -m1 5.0 1/120 248(212) 250(231) 127 132 72 69 394 3.0 4.8 5/120 286(275) 272(272) 97 93 60 56 312 3.6 5.4 10/120 296(285) 296(282) 80 84 58 56 151 3.8 5.5 15/120 290(282) 279(285) 93 98 66 60 283 4.0 6.0 20/120 310(285) 285(292) 78 80 60 61 220 3.6
(.onlrol 1. 2 v 160 101) 100 100 100 100 (3024 8) (11127 3) (1116111) (7411)) (6112 cyclclt) a. WRA! determined after luur'ideringa TABLE V-B HCl 1 v p Exposure Wrinkle Recovery Angle, Tearing Strength Tensile Strength Stoll Flex Wash- Add-on Time/Temp. W F, (degrees) retention) retention) Abrasion Wear (min/"C) Dry 1 Wet Warp Fill Warp 7 Fill retention) Ratings 5.5 1/120 309(302)" 308(305 66 74 51 54 89 3.0 4.8 2/120 314(305) 304(303) 44 75 23 17 59 3.4 5.0 3/120 322(a) 320(a) 31 11 24 16 21 4.3 48 4/120 312(a) 297(a) a 31 a a a a a 51120 a a a a a a a a a /120 a a a a a a a a 6.4 1/100 275(267) 299(285) 77 v'93 51 53 128 3.5 6.2 2/100 310(284) 312(289) 26 31 45, 34 3.6 5.9 3/100 310(293) 304(299) l7 18 47 14. 12 3.8 4/100 312(a) 314(a) 2 13 9 3 3.8
a 5/100 a a 2 a a a r a a a 10/100 a a 2 a a a a a 5 8 1/80 280(266) 295(252) 68 89 52 63 175 3.5 6.1 2/80 286(288) 308(280) 67 82 51 60 158 3.6 5.9 3/80 307(291) 303(290) 32 27 33 37 52 3.8 4.7 4/80' 293(290) 316(301) 26 28 27 '34 22 I 3.7 5.2 5/80 -304(294) 312(293) a 23 16 16 12 4.0 a 7 10/80 a, r a a a a a a a 48 1/60 286(260) 279(270) -87 94 67 72 166 I 3.6 5.5 2/60 299(262) 29.2(282) 53 78 59 55, 98 4.3 6.1 3/60 303(291) 304(296) 46 38 40 49 68 v 4.0 5.9 4/60 3021296) 316(298) a 31 35 50 4.2 5.7 5/60 306(291) 307(301) a 21 26- 29 16 v a 3.6
a 10/60 a a a a a a a a Control (3024s) (1827 g) (186 lb) (74 lb) (602 cycles) a. Too weak to test 7 b. WRAs determinedefter l0 launderings- With respect to the formic acid system, it is evident from these data that the degree of crosslinking of fabrics as measured by the development of WRAs (wrinkle recovery angles) increased as the length of exposure time or reaction temperature increased. Conversely, the strength retention of these fabrics diminished somewhat as the reaction temperature increased. However, strength losses exhibited by the postheated fabrics were considerably smaller than those shown by the control fabrics. Reaction time, on the other hand, had a less pronounced effect ,on' strength retention Fabrics exposed for 5 to 20 minutes exhibited similar degrees of strength retentions.
Thus, these results indicate that the process of this invention can be operated within a wide'range of reaction times without significantly adversely affecting the strength retention of the treated fabrics. The use of temperatures above 80C. (100 or 120C.) is preferred in order to obtain high levels of crosslinking when using Permafresh 1 13B. The use of other crosslinking agents such as methylated methylolmelamine (Resloom M-75, Monsanto), methylolmelamine (Resloom HP,
- Monsanto), and a triazineformaldehyde condensate longer than 5 minutes were too weak to be tested.
Due to the extreme acid degradation exhibited by all hydrochloric acid-catalyzed samples after the postheating step, it was impossible to measure any of their physical properties. From the above observations, it can be concluded that some of. the basic difi'erences between the hydrochloric and formic acid or acetic acid catalyzed systems using fabrics impregnated with methylolamides are: l the range of reaction times and temperatures uder which both systems operate, (2) the method ofremoving the volatile residues (i.e., by washing or heat soaking), and (3) the possibility of treating garments rather than flat goods due to the omission of the neutralizing and washing steps in the formic acidor acetic acidcatalyzed process.
Some of the disadvantages of the hydrochloric acidcatalyzed system are: (l) excessive degradation of the cotton fibers, (2) the need for neutralization of the fabric after treatment, (3) the need for afterwash, (4) lack of reproducibility due to the narrow range of reaction times and temperatures under which the process operates, and (5) the need for special controls and equipment for handling the highly corrosive and toxid hydrochloric acid. a
EXAMPLE V1 The twill samples of Example V were treated with an aqueous solution containing 20 percent dimethylolethyleneurea (Rhonite R-l, Rohm and Haas C0.) and 10 percent Rhoplex K-l4, dried and exposed to gaseous formic acid for 5 minutes at C. Conditions and results are shown in Table VI.
arp Washlostheating Wnnkle Recovery Angles, Tearing Strength Tensile Strength Stoll Flex Wear Add-on Time Temp W F, (degrees) retention) (2 retention) Abrasion Ratings (71 (mm/"C Dry Wet Warp F 111 Warp Fill Ql retention) (3024 g) (1827 g) (186 lb) (74 lb) (602 cycles) TABLE VII Acetic S1011 Tensile Propertiel Acid Wrinkle Recovery Tearing Flex Warp F111 Expo-1.111 Total Anglo (degrees) Strength Abrasion, Work-to- Eattlnlion Tensile Work-to Extension Tcns11e Additive 11m Add-0n Warp F111 (grim) Warp Rupture It Break Strength Rupture It Break Strength (1. 5011.0!) (min) (7.) Dry Hat Dry Wot Warp F111 (c ams) (in.-1h) (1.) (1b) 1 (inn-1b) ('1) (lb).
Pm rties Alter 1 Wilhinl 2.5% Latex E-502 6 10.1 155 132 143 116 2420 1570 540 17.1 12.2 138 5.6 13 .7 53
2.07 HDPE 121 10.4 156 136 95 2540 1660 440 16.3 13.2 116 4.6 12.0 45 10 10.4 150 1.35 122 104 2980 1900 841 20.0 14.8 124 5.5 13.8 42
32$ Rhop1eX K-67 8 10.0 150 127 146 118 2220 1290 740 16.6 11.6 140 6.9 15.6 54
Properties lute:- 1O washings 2.57. Latex 5-502 8 6.3 152 130 1:11. 105 2600 1840 900 17.3 13.3 134 7.5 15.9 51
2.07. HDPE 12 152 126 120 109 2450 1910 290 17.1 15.4 112 5. 1 13.0 43
n a n.3. n a 90 68 64 82 4240 2760 620 26.3 12.6 174 11.2 19.9 70
n.n. a not app1icab1a.
a. Fabric: exposed at 115C. 11. 111111 density po1yethy1eno.
EXAMPLE v11 Cotton twill fabrics (7.8 oz/sq yd NCC standard twill) were padded to 70 percent wet pickup with an aqueous solution containing 15 percent trimethylolmelamine (Resloom HP. Monsanto) and either 2.5 percent (solids) Urethane Latex E-502 (Wyandotte Chem. Corp.), 2.0 percent (solids) high density polyethylene or 3.2 percent (solids) Rhoplex K-87, dried, I
and then exposed to acetic acid vapor at l 15C. Condi- Lions and results are shown in T tble vll.
lt is evident from Table Vll that acetic acid is capable of producing samples with wrinkle recovery and tensile strengths retention comparable to those obtained with formic acid vapor.
The principles, preferred embodiments and modes of operation of the present invention have been described in the foregoing specification. The invention which is intended to be protected herein, however, is not to be construed as limited to the particular forms disclosed, since these are to be regarded as illustrative rather than restrictive. Variations and changes may be made by those skilled in the art without departing from the spirit of the invention.
3,8lli,131
What is claimed: 7 l. A process for improving the dimensional stability, wrinkle resistance, smooth drying characteristics and total shape retentivity of a cellulose fiber-containingfabric which process consists essentially of:
a. applying to the fabric an aqueous solution of a water-soluble crease-proofing agent containing reactive N-methylol groups;
b. heating the impregnated fabric containing the said crease-proofing agent in a non-reactive'vapor atmosphere containing a catalyst selected from the group consisting of formic acid and acetic acid vapor as essentially the only reactive component to a temperature between above 80C. and up to about 160C. for a time of between about 1 to about 20 minutes to crosslink the cellulose fibers to a first level of crosslinking; and
c. heating the said crosslinked fabric in an inert atmosphere in the absence of additional catalyst to a temperature of above about 100C. to further cure the said crosslinked fabric to a second level of cross-linking having increased Wrinkle Recovery Angles and Wash-Wear Ratings while dissipating residual reagents.
2. A process according to claim 1 wherein said aqueous solution contains from about I to about 40 percent of the said crease-proofing agent.
3. A process for improving the dimensional stability,
I crease resistance, smooth drying characteristics and total shape retentivity of cotton-containing fabrics which comprises in sequence the steps of:
a. applying to the fabric an aqueous solution consisting essentially of about 5 to about percent by weight of a water-soluble, crease-proofing agent containing reactive N-methylol groups;
b. conditioning or drying the fabric to give the cotton a moisture content of between about 2 to about 100 percent based on dry weight of the fabric;
c. exposing the conditioned fabric to a non-reactive vapor phase consisting essentially of a catalytically effective amount of formic acid or acetic acid as essentially the only reactive component in a reaction zone maintained at a temperature between about [00C. and about 140C. for a time of between about 1 and minutes to crosslink the cotton fibers to a first level of crosslinking;
d. at the end of said crosslinking step (c) heating said fabric in an inert gaseous atmosphere in the ab- 5. A process according to claim 3 wherein said nonreactive vapor phase consists essentially of acetic acid.
6. A process for improving the dimensional stability,
wrinkle resistance, smooth drying characteristics and total shape retentivity of cotton-containing fabrics which consists of the sequential steps of:
a. impregnating the fabric with an aqueous solution containing about 5 to 15 percent trimethylolmelamine or dihydroxydimethylolethyleneurea to give a wet pick-up between about 65 and percent based on dry cotton weight;
b. drying and conditioning the impregnated fabric to a moisture content of between about 3 to about 65 percent;
0. exposing the fabric to a non-reactive gaseous atmosphere consisting of from about 20 to 50 volume percent of a catalytic material taken from the group consisting of formic acid and acetic acid, balance inert gaseous material, at a temperature between and C. for a time of about 2 to about 15 minutes, thereby effecting a first level of crosslinking;
d. removing said fabric from said atmosphere; and
e. postheating the said fabric at a temperature of from about C. to about C. to further cure the fabric to a second level of crosslinking while dissipating residual reagents.
7. A process according to claim 6 wherein the fabric is introduced into the process as a flat fabric, and prior to step (c) is formed into a garment.
8. A process according to claim 6 which process is continuous and in which the fabric being treated is flat fabric.
9. A process according to claim 6 which process is continuous and in which the fabric being treated is a garment.
Claims (8)
- 2. A process according to claim 1 wherein said aqueous solution contains from about 1 to about 40 percent of the said crease-proofing agent.
- 3. A process for improving the dimensional stability, crease resistance, smooth drying characteristics and total shape retentivity of cotton-containing fabrics which comprises in sequence the steps of: a. applying to the fabric an aqueous solution consisting essentially of about 5 to about 15 percent by weight of a water-soluble, crease-proofing agent containing reactive N-methylol groups; b. conditioning or drying the fabric to give the cotton a moisture content of between about 2 to about 100 percent based on dry weight of the fabric; c. exposing the conditioned fabric to a non-reactive vapor phase consisting essentially of a catalytically effective amount of formic acid or acetic acid as essentially the only reactive component in a reaction zone maintained at a temperature between about 100*C. and about 140*C. for a time of between about 1 and 20 minutes to crosslink the cotton fibers to a first level of crosslinking; d. at the end of said crosslinking step (c) heating said fabric in an inert gaseous atmosphere in the absence of additional catalyst at a temperature of from about 100*C. to about 180*C., to further cure the fabric to a second, higher level of crosslinking while dissipating residual reagents thereby directly producing a dry, crosslinked, essentially neutral fabric.
- 4. A process according to claim 3 wherein said non-reactive vapor phase consists essentially of formic acid.
- 5. A process according to claim 3 wherein said non-reactive vapor phase consists essentially of acetic acid.
- 6. A process for improving the dimensional stability, wrinkle resistance, smooth drying characteristics and total shape retentivity of cotton-containing fabrics which consists of the sequential steps of: a. impregnating the fabric with an aqueous solution containing about 5 to 15 percent trimethylolmelamine or dihydroxydimethylolethyleneurea to give a wet pick-up between about 65 and 85 percent based on dry cotton weight; b. drying and conditioning the impregnated fabric to a moisture content of between about 3 to about 65 percent; c. exposing the fabric to a non-reactive gaseous atmosphere consisting of from about 20 to 50 volume percent of a catalytic material taken from the group consisting of formic acid and acetic acid, balance inert gaseous material, at a temperature between 110* and 125*C. for a time of about 2 to about 15 minutes, thereby effecting a first level of crosslinking; d. removing said fabric from said atmosphere; and e. postheating the said fabric at a temperature of from about 140*C. to about 160*C. to further cure the fabric to a second level of crosslinking while dissipating residual reagents.
- 7. A process according to claim 6 wherein the fabric is introduced into the process as a flat fabric, and prior to step (c) is formed into a garment.
- 8. A process according to claim 6 which process is continuous and in which the fabric being treated is flat fabric.
- 9. A process according to claim 6 which process is continuous and in which the fabric being treated is a garment.
Priority Applications (17)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US00238983A US3811131A (en) | 1968-09-24 | 1972-03-28 | Durable press process for treating cellulosic material with methylolamides and acetic acid or formic acid vapors |
GB1077373A GB1390318A (en) | 1972-03-28 | 1973-03-06 | Process for the wrinkle resistance and other properties of cellulosic fibre-containing fabric |
AU53084/73A AU468092B2 (en) | 1968-09-24 | 1973-03-08 | Durable press process for treating cellulosic materials with methylolamides and acentic acid or formic acid capors |
IN535/CAL/1973A IN137845B (en) | 1972-03-28 | 1973-03-12 | |
CA166,077A CA998806A (en) | 1968-09-24 | 1973-03-14 | Durable press process for treating cellulosic material with methylolamides and acetic acid or formic acid vapors |
DE19732314042 DE2314042A1 (en) | 1972-03-28 | 1973-03-21 | PROCESS FOR FINISHING PRODUCTS CONTAINING CELLULOSE FIBERS, SUCH AS CLOTH MADE FROM COTTON OR COTTON BLENDS |
NL7304066A NL7304066A (en) | 1972-03-28 | 1973-03-23 | |
CH438773A CH586783B5 (en) | 1972-03-28 | 1973-03-27 | |
ES413064A ES413064A1 (en) | 1972-03-28 | 1973-03-27 | Process for the wrinkle resistance and other properties of cellulosic fibre-containing fabric |
CH438773D CH438773A4 (en) | 1972-03-28 | 1973-03-27 | |
FR7310881A FR2178024B1 (en) | 1972-03-28 | 1973-03-27 | |
SE7304269A SE392924B (en) | 1972-03-28 | 1973-03-27 | WAY TO ALLOCATE CELLULOSA-CONTAINING MATERIAL PERMANENT PRESS PROPERTIES BY TREATMENT WITH AN AGENT CONTAINING REACTIVE N-METHYLOL GROUPS |
BE129316A BE797395A (en) | 1972-03-28 | 1973-03-27 | PROCESS FOR RENDERING CELLULOSIC MATERIALS WRINKLE BY MEANS OF METHYLOLAMIDES AND ACETIC OR FORMIC ACID VAPORS |
IT2222973A IT981674B (en) | 1972-03-28 | 1973-03-27 | DURABLE FORMING PROCESS FOR THE TREATMENT OF CELLULOSE MATERIAL WITH METHYLOLAMIDES AND ACETIC ACID OR FORMIC ACID VAPORS |
AR42729673A AR197805A1 (en) | 1972-03-28 | 1973-03-28 | PROCEDURE TO IMPROVE THE DIMENSIONAL STABILITY, RESISTANCE TO WRINKLES, UNIFORM DRYING CHARACTERISTICS AND TOTAL RETENTIVITY OF THE SHAPE OF A FABRIC CONTAINING CELLULOSE FIBERS |
BR224473A BR7302244D0 (en) | 1972-03-28 | 1973-03-28 | PROCESS TO IMPROVE DIMENSIONAL STABILITY, RESISTANCE OF BINDING, DRYING CHARACTERISTICS WITHOUT CRAFTING AND TOTAL RETENTION OF THE FORM OF A FABRIC CONTAINING CELLULOSIC FIBERS |
JP3552073A JPS496297A (en) | 1972-03-28 | 1973-03-28 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US76211968A | 1968-09-24 | 1968-09-24 | |
US00238983A US3811131A (en) | 1968-09-24 | 1972-03-28 | Durable press process for treating cellulosic material with methylolamides and acetic acid or formic acid vapors |
Publications (1)
Publication Number | Publication Date |
---|---|
US3811131A true US3811131A (en) | 1974-05-21 |
Family
ID=26932159
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00238983A Expired - Lifetime US3811131A (en) | 1968-09-24 | 1972-03-28 | Durable press process for treating cellulosic material with methylolamides and acetic acid or formic acid vapors |
Country Status (3)
Country | Link |
---|---|
US (1) | US3811131A (en) |
AU (1) | AU468092B2 (en) |
CA (1) | CA998806A (en) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3909199A (en) * | 1972-06-29 | 1975-09-30 | Us Agriculture | Catalyst assist agents using leaving group effects |
US4240943A (en) * | 1978-02-27 | 1980-12-23 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Textile finishing composition |
US4281998A (en) * | 1980-02-04 | 1981-08-04 | Eastman Kodak Company | Solvent-resistant alkylated melamine cross-linked cellulose ester articles |
US4964177A (en) * | 1988-08-03 | 1990-10-23 | Huang Ding S | Bustdart-free tailoring process for a fitted-waist dress to eliminate cutting of its backpiece |
US5112652A (en) * | 1989-08-29 | 1992-05-12 | East Central Wax Company, Inc. | Formaldehyde scavenging process useful in manufacturing durable press finished fabric |
US5160679A (en) * | 1989-08-29 | 1992-11-03 | Greene Jack T | Process for making particle board including the use of acetoacetamide as a formaldehyde scavenger |
US5202077A (en) * | 1990-07-10 | 1993-04-13 | Milliken Research Corporation | Method for removal of substrate material by means of heated pressurized fluid stream |
US5404626A (en) * | 1993-10-25 | 1995-04-11 | Milliken Research Corporation | Method and apparatus to create an improved moire fabric by utilizing pressurized heated gas |
US5467512A (en) * | 1994-02-14 | 1995-11-21 | Burlington Industries, Inc. | Knitted fabric construction for an industrially launderable knitted garment |
US5477595A (en) * | 1994-02-14 | 1995-12-26 | Burlington Industries, Inc. | Knitted fabric construction for an industrially launderable soft hand knitted garment |
US6051034A (en) * | 1998-09-30 | 2000-04-18 | Springs Industries, Inc. | Methods for reducing pilling of towels |
WO2006092330A1 (en) * | 2005-03-04 | 2006-09-08 | Basf Aktiengesellschaft | Production of moulded bodies from lignocellulose-based fine particle materials |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB437642A (en) * | 1934-02-03 | 1935-11-04 | Calico Printers Ass Ltd | Improvements relating to the processing or treatment of fabrics or textile fibres |
US2235141A (en) * | 1937-10-15 | 1941-03-18 | Celanese Corp | Treatment of artificial materials |
US2441859A (en) * | 1945-06-12 | 1948-05-18 | Alrose Chemical Company | Treatment of textile materials with aldehydes |
FR1359102A (en) * | 1961-11-06 | 1964-04-24 | F M Hammerle Textilwerke Fa | Process for improving the use characteristics of cellulosic materials obtained from native or regenerated cellulose |
US3310363A (en) * | 1963-05-24 | 1967-03-21 | St Regis Paper Co | Process of reacting cellulose paper of low water content with gaseous formaldehyde |
US3647353A (en) * | 1966-08-26 | 1972-03-07 | Triatex International | Method and apparatus for processing cellulose-containing textiles with the vapors from an azeotropic liquid comprising an acidic catalyst |
US3653805A (en) * | 1968-09-24 | 1972-04-04 | Cotton Inc | Delayed cure process using formaldehyde vapor to cause creaseproofing |
US3706526A (en) * | 1971-12-06 | 1972-12-19 | Cotton Inc | Process for treating cellulosic material with formaldehyde and sulfur dioxide |
-
1972
- 1972-03-28 US US00238983A patent/US3811131A/en not_active Expired - Lifetime
-
1973
- 1973-03-08 AU AU53084/73A patent/AU468092B2/en not_active Expired
- 1973-03-14 CA CA166,077A patent/CA998806A/en not_active Expired
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GB437642A (en) * | 1934-02-03 | 1935-11-04 | Calico Printers Ass Ltd | Improvements relating to the processing or treatment of fabrics or textile fibres |
US2235141A (en) * | 1937-10-15 | 1941-03-18 | Celanese Corp | Treatment of artificial materials |
US2441859A (en) * | 1945-06-12 | 1948-05-18 | Alrose Chemical Company | Treatment of textile materials with aldehydes |
FR1359102A (en) * | 1961-11-06 | 1964-04-24 | F M Hammerle Textilwerke Fa | Process for improving the use characteristics of cellulosic materials obtained from native or regenerated cellulose |
US3310363A (en) * | 1963-05-24 | 1967-03-21 | St Regis Paper Co | Process of reacting cellulose paper of low water content with gaseous formaldehyde |
US3647353A (en) * | 1966-08-26 | 1972-03-07 | Triatex International | Method and apparatus for processing cellulose-containing textiles with the vapors from an azeotropic liquid comprising an acidic catalyst |
US3653805A (en) * | 1968-09-24 | 1972-04-04 | Cotton Inc | Delayed cure process using formaldehyde vapor to cause creaseproofing |
US3706526A (en) * | 1971-12-06 | 1972-12-19 | Cotton Inc | Process for treating cellulosic material with formaldehyde and sulfur dioxide |
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Title |
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Gagliardi et al., Textile Research Journal, 36, 168 177 (1966). * |
Gagliardi, from Proceedings of the Conference on the Conference on the Vapor Phase Finishing of Cotton, held at New Orleans, La. on Feb. 24, 1967 published March 1968, p. 35. * |
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Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3909199A (en) * | 1972-06-29 | 1975-09-30 | Us Agriculture | Catalyst assist agents using leaving group effects |
US4240943A (en) * | 1978-02-27 | 1980-12-23 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Textile finishing composition |
US4281998A (en) * | 1980-02-04 | 1981-08-04 | Eastman Kodak Company | Solvent-resistant alkylated melamine cross-linked cellulose ester articles |
US4964177A (en) * | 1988-08-03 | 1990-10-23 | Huang Ding S | Bustdart-free tailoring process for a fitted-waist dress to eliminate cutting of its backpiece |
US5112652A (en) * | 1989-08-29 | 1992-05-12 | East Central Wax Company, Inc. | Formaldehyde scavenging process useful in manufacturing durable press finished fabric |
US5160679A (en) * | 1989-08-29 | 1992-11-03 | Greene Jack T | Process for making particle board including the use of acetoacetamide as a formaldehyde scavenger |
US5674581A (en) * | 1990-07-10 | 1997-10-07 | Milliken Research Corporation | Textile fabric having a thermally modified narrow channel to facilitate separation |
US5202077A (en) * | 1990-07-10 | 1993-04-13 | Milliken Research Corporation | Method for removal of substrate material by means of heated pressurized fluid stream |
US5404626A (en) * | 1993-10-25 | 1995-04-11 | Milliken Research Corporation | Method and apparatus to create an improved moire fabric by utilizing pressurized heated gas |
US5467512A (en) * | 1994-02-14 | 1995-11-21 | Burlington Industries, Inc. | Knitted fabric construction for an industrially launderable knitted garment |
US5477595A (en) * | 1994-02-14 | 1995-12-26 | Burlington Industries, Inc. | Knitted fabric construction for an industrially launderable soft hand knitted garment |
US5515699A (en) * | 1994-02-14 | 1996-05-14 | Burlington Industries, Inc. | Knitted fabric construction for an industrially launderable soft hand knitted garment |
US5515700A (en) * | 1994-02-14 | 1996-05-14 | Burlington Industries, Inc. | Knitted fabric construction for an industrially launderable knitted garment |
US6051034A (en) * | 1998-09-30 | 2000-04-18 | Springs Industries, Inc. | Methods for reducing pilling of towels |
WO2006092330A1 (en) * | 2005-03-04 | 2006-09-08 | Basf Aktiengesellschaft | Production of moulded bodies from lignocellulose-based fine particle materials |
US20080246177A1 (en) * | 2005-03-04 | 2008-10-09 | Basf Aktiengesellschaft | Production of Moulded Bodies From Lignocellulose-Based Fine Particle Materials |
Also Published As
Publication number | Publication date |
---|---|
AU468092B2 (en) | 1975-12-18 |
AU5308473A (en) | 1974-09-12 |
CA998806A (en) | 1976-10-26 |
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