US3177093A - Method of treating cellulose textile material and the treated material - Google Patents
Method of treating cellulose textile material and the treated material Download PDFInfo
- Publication number
- US3177093A US3177093A US200315A US20031562A US3177093A US 3177093 A US3177093 A US 3177093A US 200315 A US200315 A US 200315A US 20031562 A US20031562 A US 20031562A US 3177093 A US3177093 A US 3177093A
- Authority
- US
- United States
- Prior art keywords
- urea
- formaldehyde
- curing
- present
- imidazolidinone
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 29
- 239000000463 material Substances 0.000 title claims description 25
- 239000004753 textile Substances 0.000 title claims description 20
- 229920002678 cellulose Polymers 0.000 title claims description 12
- 239000001913 cellulose Substances 0.000 title claims description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 46
- 238000011084 recovery Methods 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 19
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 claims description 13
- 238000001035 drying Methods 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000004326 stimulated echo acquisition mode for imaging Methods 0.000 claims 1
- 229920005989 resin Polymers 0.000 description 24
- 239000011347 resin Substances 0.000 description 24
- 239000004744 fabric Substances 0.000 description 21
- 230000037303 wrinkles Effects 0.000 description 20
- 235000013877 carbamide Nutrition 0.000 description 15
- -1 cyclic ureas Chemical class 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 14
- 229920000742 Cotton Polymers 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 229920001807 Urea-formaldehyde Polymers 0.000 description 8
- 239000011701 zinc Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 150000003751 zinc Chemical class 0.000 description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- 238000004061 bleaching Methods 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 4
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical class NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- 230000011987 methylation Effects 0.000 description 3
- 238000007069 methylation reaction Methods 0.000 description 3
- 238000009988 textile finishing Methods 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- DWEQVNFWAKJCEY-UHFFFAOYSA-N 4-methylimidazolidin-2-one Chemical compound CC1CNC(=O)N1 DWEQVNFWAKJCEY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229920003180 amino resin Polymers 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- 229960001763 zinc sulfate Drugs 0.000 description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 description 2
- IVHPTCPLBMAFMT-UHFFFAOYSA-N 1-hydroxy-5-methylimidazolidin-2-one Chemical compound ON1C(NCC1C)=O IVHPTCPLBMAFMT-UHFFFAOYSA-N 0.000 description 1
- CIJBZJVYLYXASM-UHFFFAOYSA-N 1-hydroxyimidazolidin-2-one Chemical compound ON1CCNC1=O CIJBZJVYLYXASM-UHFFFAOYSA-N 0.000 description 1
- RTPNQRLGWKMEEK-UHFFFAOYSA-N 1-propan-2-ylimidazolidin-2-one Chemical compound CC(C)N1CCNC1=O RTPNQRLGWKMEEK-UHFFFAOYSA-N 0.000 description 1
- GJMPSRSMBJLKKB-UHFFFAOYSA-N 3-methylphenylacetic acid Chemical compound CC1=CC=CC(CC(O)=O)=C1 GJMPSRSMBJLKKB-UHFFFAOYSA-N 0.000 description 1
- 244000198134 Agave sisalana Species 0.000 description 1
- 241001156002 Anthonomus pomorum Species 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
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Inorganic materials [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 1
- SUPOBRXPULIDDX-UHFFFAOYSA-N [[4-amino-6-(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound NC1=NC(NCO)=NC(NCO)=N1 SUPOBRXPULIDDX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- YIBPLYRWHCQZEB-UHFFFAOYSA-N formaldehyde;propan-2-one Chemical compound O=C.CC(C)=O YIBPLYRWHCQZEB-UHFFFAOYSA-N 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- ARZLUCYKIWYSHR-UHFFFAOYSA-N hydroxymethoxymethanol Chemical compound OCOCO ARZLUCYKIWYSHR-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229950005308 oxymethurea Drugs 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229940117957 triethanolamine hydrochloride Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 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
- 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
- Y10S156/00—Adhesive bonding and miscellaneous chemical manufacture
- Y10S156/91—Bonding tire cord and elastomer: improved adhesive system
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2965—Cellulosic
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2971—Impregnation
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
- Y10T442/2393—Coating or impregnation provides crease-resistance or wash and wear characteristics
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2762—Coated or impregnated natural fiber fabric [e.g., cotton, wool, silk, linen, etc.]
- Y10T442/277—Coated or impregnated cellulosic fiber fabric
- Y10T442/2828—Coating or impregnation contains aldehyde or ketone condensation product
- Y10T442/2852—Amide-aldehyde condensate [e.g., modified urea-aldehyde condensate, etc.]
Definitions
- the present invention relates to the method of applying thermosetting cyclic urea-formaldehyde resins to cellulose-containing textile materials, and to the materials so treated, and more particularly to a method for obtaining higher than normal tensile strength on cellulose-containing textile materials with little or no sacrifice in wrinkle recovery.
- the textile industry has employed many finishes of the resin type to impart wrinkle resistance and dimensional stability to cellulosic materials, such as cotton, viscose rayon and the like.
- One of the first of these resins to be used was the urea-formaldehyde type. This product had serious defects in that it caused extensive tensile strength losses when the amount of resin applied was snificient to give satisfactory crease resistance. This was particularly true when used on cotton fabrics. In addition, the loss in tensile strength when a fabric was scorched after chlorine bleaching was extensive.
- the urea-formaldehyde resin was replaced with the methylated methylol melamine resins, which imparted satisfactory crease resistance to cellulose textile materials at lower concentrations and without serious loss in tensile strength due to chlorine belaching.
- certain methylated methylol melamines had the somewhat serious defect of discoloring when the fabrics were subjected to a bleaching operation in which chlorine was used.
- ethylene urea type resins In order to avoid the disadvantages of yellowing following chlorine bleaching which resulted when some methylated methylol melamine resins were used, recourse was had to the use of ethylene urea type resins. These materials had the advantage that they did not discolor fabric treated therewith after bleaching with chlorine and further that they could be used in high concentrations to obtain excellent high wrinkle recovery without imparting stiffness to the fabrics.
- the ethylene urea or cyclic urea type resin however, had the disadvantage that they gave a substantially greater loss in tensile strength than Accordingly,it is an object of the present invention to provide a process whereby a wrinkle resistance of high order may be achieved, while simultaneously maintaining a high order of tensile strength.
- a method for the treating of cellulose-containing textile materials whereby a high order of tensile strength and wrinkle recovery are obtained even at high resin solids on the fabric which comprises applying thereto a formaldehyde condensate of a cyclic urea, and thereafter curing said cyclic urea in the presence of a zinc salt catalyst in an atmosphere of steam. Following the effective curing of the above described conditions, the so finished fabric is allowed to dry, either at room temperature or under the normal drying conditions employed in textile finishing plants.
- formaldehyde condensates of cyclic ureas we refer to the methylol derivatives, of ethylene urea and certain of its homologs, as for example, 1,2-propylene urea, and certain alkyl substituted derivatives thereof, as well as hydroxyl substituted derivatives thereof.
- R through R are selected from the group consisting of hydrogen, saturated aliphatic alkyl groups containing from 1 to 4 carbon atoms, and hydroxyl.
- the preferred species within the above general formula is where R through R is hydrogen or where one of the values is methyl and the remainder are hydrogen. With respect to alkyl substitution for R through R the total number of carbon atoms in substituting groups should not exceed 6.
- dimethylol derivative is illustrated, it should be noted that while the dimethylol derivative is preferred, cyclic ureas having at least 1.5 mole of combined formaldehyde as methylol formaldehyde are fully contemplated in accordance with the present invention.
- Z-imidazolidinone (ethylene urea); .3-methyl-2-imidazolidinone, 1-2-propylene urea; 3,4-dirnethyl-2-imidazolidinone; 3,3,4-trimethyl-2 imidazolidinone; 3,3,4,4-tetramethyl-Z-imidazolidinone; 3,4-diethyI-Z-imidazolidinone; 3,3-dimethyl-4-ethyl-2-imidazolidinone; 3-methyl-3-ethyl-2-imidazolidinone; '3,4-dimethyl-3-n-propyl 2-imidazolidinone; 3-isopropyl-2-imidazolidinone;' 3methyl-3-isopropyl-4-ethyl-2-imidazolidinone; 3-n butyl-2-irnidazolid
- the methylolation may be carried out at a pH of inaccordance with the present procedure and more preffrom between 3 and and preferably at a pH of from between 7 and 10 at a temperature of from between '40 and reflux or about 100 C. until solution is achieved. Thereafter, the reaction mixture is cooled.
- the mole ratio between the cyclic urea and formaldehyde is 1 to 2, respectively.
- the degree of methylolation is not appreciably I increased and the presence of increased amounts of free formaldehyde increases handling difiiculties and presents other known problems.
- the mole ratio is 1 to 2,.
- the resulting product may be identified as a dimethylol compound in that by analysis, as much. as 1.9 moles of the available 2 moles of formaldehyde. are combined.
- the present invention is ap plicable .to textile materials containing cellulose.
- cellulose textile material and similar expressions, as they are employed herein, is intended to include textile materials including fibers, filaments, yarns, formed fabrics, containing at least 50% cellulose.
- Materials,'as for example, flax, cotton, jute, hemp, sisal, and regenerated cellulose, as for example, viscose rayon, cuprammonium or the like are alsoincluded;
- expressions-such as are identified above and similar ex pressions are intended to include cotton and viscose rayon textile fabrics, whether they be woven, knitted, non-woven,
- V The methylol condensates of cyclic ureas as they. are
- heat-curable resinous materials may be applied by padding, dipping, spraying, immersion or other suitable techniques,
- the only catalysts that we have found to be suitable in accordance with our present invention are in-. organic salts of zinc.
- fZinc salts as that term is employed herein is intended to include the salts derived from the reaction of zinc oxide or zinc hydroxide with inorganic acids.
- the expression includes-zinc chloride, zinc sulfate, zinenitrate, and the like. Of these V enumerated, zinc nitrate is greatly preferred because .of its solubility and pad bath stability.
- zinc catalysts are employed in amountsof from between -1 and 36%, based on the weight of resin solids employed erably in amounts of from between5 and 15%, based on the weight of resin solids employed in a given treating solution.
- curing time's employed in the present process are somewhat longer than those conventionally used.
- time of cure may be shortened or. lengthened within given limits depending :uponv other variablesssuch as steam temperature, amount of vcatalysts, etc., it is usually preferred to effect cure at times between about 30 minutes and 2 /2 hours.
- EXAMPLE 1 Pad 'baths were prepared containing 19.0%, 27.5% and 35.0% resin solids of dimethylol ethylene urea and 12% on the weight of the resin solids in ther bath of zinc nitrate or magnesium'chloride as curing accelerators.
- Dimethylol ethylene urea can be cured on the fabric at 210 F. (in steam) with zinc nitrate as a catalyst to obtain approximately normal wrinkle recovery and higher than normal tensile strength. Good fixation of resin is obtained, as indicated by the nitrogen analysis.
- tensile strength values of the order of at least 80 pounds may be achieved for wrinkle recoveries of 240 and higher, and that for wrinkle recoveries higher than 280 tensile strengths of the order of greater than about 70 pounds are readily achieved by employment of the present process. Such values heretofore have not been possible.
- EXAMPLE 2 In separate applications, 17.65% of dimethylol ethylene urea was applied to cotton percale employing varying amounts of well known curing accelerators, based on the weight of resin solids. An 85% wet pick-up was obtained, leaving resin solids on the weight of the fabric. The fabric was then steam cured for 2.5 hours at i 210 F.
- the applied solutions were as follows.
- Table IV illustrates the unique character of the cyclic ureas in the present invention. Compare Examples 1 and 3.
- any of the cyclic ureas identified hereinabove or catalysts set forth therein suitable for use in the presentinvention maybe employed singly or in combination with one another, and to some extent with other known teX-' tile finishing resins, as for example, urea-formaldehyde resins and their alkylated derivatives, melamine-formaldehyde resins and their alkylated derivatives, 6-ring memberedcyclic ureas, such as 1,3-propylene urea-formaldehyde, condensates and derivatives thereof, epoxy resins,
- ishing assistants may be employed in the. processof the present invention, such as wetting agents, softeners and the like, insofar as their inclusion in the treating bath on the weight of resin solids, v V
- a cotton textile material prepared by the process of claim 1 having from 1 to 40% based ontheweight of V the textile material ofa cured formaldehyde condensate.
- a method for treating formed cotton fabric whereby high tensile strength andwrinkle recovery are obtained, which-comprises applying from" an aqueous solution from about 2.5 to about 25% of a formaldehyde condensate. of a S-membered cyclic ureaand a zinc salt of an inorganic acid as a catalyst therefor, said zinc salt being selected from the group consisting of zinc" chloride,
Description
United States Patent METHOD OF TREATING CELLULOSE TEXTILE MATERIAL AND THE TREATED MATERIAL William Julius van Loo, In, Midrliesex, and Samuel James OBrien, Dunellen, N.J., assignors to American Cyanamid Company, Stamford, Conn., a corporation of Maine No Drawing. Continuation of application Ser. No. 796,209, Mar. 2, 1959. This application June 6, 1962, Ser. No. 200,315
Claims. (Cl. 117-1394) The present invention relates to the method of applying thermosetting cyclic urea-formaldehyde resins to cellulose-containing textile materials, and to the materials so treated, and more particularly to a method for obtaining higher than normal tensile strength on cellulose-containing textile materials with little or no sacrifice in wrinkle recovery.
In the past, the textile industry has employed many finishes of the resin type to impart wrinkle resistance and dimensional stability to cellulosic materials, such as cotton, viscose rayon and the like. One of the first of these resins to be used was the urea-formaldehyde type. This product had serious defects in that it caused extensive tensile strength losses when the amount of resin applied was snificient to give satisfactory crease resistance. This was particularly true when used on cotton fabrics. In addition, the loss in tensile strength when a fabric was scorched after chlorine bleaching was extensive.
Gradually, the urea-formaldehyde resin was replaced with the methylated methylol melamine resins, which imparted satisfactory crease resistance to cellulose textile materials at lower concentrations and without serious loss in tensile strength due to chlorine belaching. However, during use, it was discovered that certain methylated methylol melamines had the somewhat serious defect of discoloring when the fabrics were subjected to a bleaching operation in which chlorine was used.
In order to avoid the disadvantages of yellowing following chlorine bleaching which resulted when some methylated methylol melamine resins were used, recourse was had to the use of ethylene urea type resins. These materials had the advantage that they did not discolor fabric treated therewith after bleaching with chlorine and further that they could be used in high concentrations to obtain excellent high wrinkle recovery without imparting stiffness to the fabrics. The ethylene urea or cyclic urea type resin, however, had the disadvantage that they gave a substantially greater loss in tensile strength than Accordingly,,it is an object of the present invention to provide a process whereby a wrinkle resistance of high order may be achieved, while simultaneously maintaining a high order of tensile strength.
It is a further object of the present invention to provide such a process which maybe readily and economically adapted by most textile finishing installations.
These and other objects and advantages of the present invention will become more apparent from the detailed description thereof set forth hereinbelow.
ice
In accordance with the present invention a method is provided for the treating of cellulose-containing textile materials whereby a high order of tensile strength and wrinkle recovery are obtained even at high resin solids on the fabric, which comprises applying thereto a formaldehyde condensate of a cyclic urea, and thereafter curing said cyclic urea in the presence of a zinc salt catalyst in an atmosphere of steam. Following the effective curing of the above described conditions, the so finished fabric is allowed to dry, either at room temperature or under the normal drying conditions employed in textile finishing plants.
By the expression formaldehyde condensates of cyclic ureas, as that term is employed herein, we refer to the methylol derivatives, of ethylene urea and certain of its homologs, as for example, 1,2-propylene urea, and certain alkyl substituted derivatives thereof, as well as hydroxyl substituted derivatives thereof.
In general, these compounds may be characterized by the following general formula:
wherein R through R, are selected from the group consisting of hydrogen, saturated aliphatic alkyl groups containing from 1 to 4 carbon atoms, and hydroxyl. The preferred species within the above general formula is where R through R is hydrogen or where one of the values is methyl and the remainder are hydrogen. With respect to alkyl substitution for R through R the total number of carbon atoms in substituting groups should not exceed 6.
While in the above general formula, the dimethylol derivative is illustrated, it should be noted that while the dimethylol derivative is preferred, cyclic ureas having at least 1.5 mole of combined formaldehyde as methylol formaldehyde are fully contemplated in accordance with the present invention.
I The cyclic ureas which are condensed with formaldehyde to form methylol derivatives employable in the process of the present invention may be prepared in accordance with'known prior art procedures by reacting a suitable diamine, including the substituted diamines, with urea, as for example, in accordance with the procedures described in US. Patents Nos. 2,436,311 and 2,517,750, which are incorporated herein by reference. As examples of suitable S-mernbered cyclic ureas within the purview of the present invention, the following are illustrative: Z-imidazolidinone (ethylene urea); .3-methyl-2-imidazolidinone, 1-2-propylene urea; 3,4-dirnethyl-2-imidazolidinone; 3,3,4-trimethyl-2 imidazolidinone; 3,3,4,4-tetramethyl-Z-imidazolidinone; 3,4-diethyI-Z-imidazolidinone; 3,3-dimethyl-4-ethyl-2-imidazolidinone; 3-methyl-3-ethyl-2-imidazolidinone; '3,4-dimethyl-3-n-propyl 2-imidazolidinone; 3-isopropyl-2-imidazolidinone;' 3methyl-3-isopropyl-4-ethyl-2-imidazolidinone; 3-n butyl-2-irnidazolidinone; 3-ethyl-4-sec-butyI-Z-imidazolidinone; 3-hydroxy-2-imidazolidinone; 3,4-dihydroxy-Z-imidazolidinone; 3-hydroxy-4-methyl-2-imidazolidinone; 3,4-dihydroxy-3,4-dirnethyl-Z-imidazolidinone; 3-hydroxy-3-methyl-4-n-propyl-2-imidazolidinone; and 3-hydr0xy-3-ethyl-4-methyl-4-isopropyLZ-imidazolidinone.
from one to three moles of the formaldehyde and pref-.
erably with from betweentwo to three moles of formaldehyde. The methylolation may be carried out at a pH of inaccordance with the present procedure and more preffrom between 3 and and preferably at a pH of from between 7 and 10 at a temperature of from between '40 and reflux or about 100 C. until solution is achieved. Thereafter, the reaction mixture is cooled. Preferably, the mole ratio between the cyclic urea and formaldehyde is 1 to 2, respectively. When the formaldehyde is increased, thedegree of methylolation is not appreciably I increased and the presence of increased amounts of free formaldehyde increases handling difiiculties and presents other known problems. When the mole ratio is 1 to 2,.
the resulting product may be identified as a dimethylol compound in that by analysis, as much. as 1.9 moles of the available 2 moles of formaldehyde. are combined.
As indicated hereinabove, the present invention-is ap plicable .to textile materials containing cellulose. The term cellulose textile material and similar expressions, as they are employed herein, is intended to include textile materials including fibers, filaments, yarns, formed fabrics, containing at least 50% cellulose. Materials,'as for example, flax, cotton, jute, hemp, sisal, and regenerated cellulose, as for example, viscose rayon, cuprammonium or the like are alsoincluded; In its more preferred sense, expressions-such as are identified above and similar ex pressions, are intended to include cotton and viscose rayon textile fabrics, whether they be woven, knitted, non-woven,
felted or otherwise formed. V The methylol condensates of cyclic ureas as they. are
identified hereinabove may be applied to textile materials in amountsvarying betweenl to 40%, based on the dry weight of the material, and preferably-in amounts of from between 2.5 and by weight. These heat-curable resinous materials may be applied by padding, dipping, spraying, immersion or other suitable techniques,
but are preferablyapplied by conventional padding proc- I esses, as in the case of formed fabrics, in that most textile finishing installations areequipped for such-applications.
It is a unique characteristic of the present process that the ureas in accordance with this invention and the unexpected results obtained therefrom are only'realized when the: resinis cured in the presence ofzinc salts as curing accelerators or catalysts. Thus, for example, mostfof the better known curing accelerators presently employed in 'alkanol amine salts, such as triethanolamine hydrochloride, and free acids, such as oxalic,.tartaric, and the like,
are not applicable irraccordance with thepresent process. As noted, the only catalysts that we have found to be suitable in accordance with our present invention are in-. organic salts of zinc. fZinc salts as that term is employed herein, is intended to include the salts derived from the reaction of zinc oxide or zinc hydroxide with inorganic acids. Thus, for example, the expression includes-zinc chloride, zinc sulfate, zinenitrate, and the like. Of these V enumerated, zinc nitrate is greatly preferred because .of its solubility and pad bath stability.
In general, zinc catalysts are employed in amountsof from between -1 and 36%, based on the weight of resin solids employed erably in amounts of from between5 and 15%, based on the weight of resin solids employed in a given treating solution.
In addition to the present invention beinglimited to cyclic urea resins and zinc salt curing accelerators in order to achieve unexpected properties, it isessential that Q curing be accomplished in anatmosphere of steam so that in'eifectthe cure is accomplished'when' thefinished material is in the wet state. Althoughan atmosphere of steam atmosphere below about .212 F. is readily accom:
plished by curing at sub-atmospheric pressures. -In general, longer time cycles are required at the lower temperatures. and shorter cycles for the higher. temperatures. Although curing in an atmosphere of steam is "greatly preferred, the curing may be'accomplished in the absence of added steam and only that steam which is generated through the drying of the impregnated, fabric need be employed. Normally, this may be accomplished by placing the treated material prior to cure in a substantially' (almost completely) closed container or chamber. Additionally, a partially saturated atmosphere of steam may. be employed. A confined or unconfined atmosphere may be used. i i
' Ingeneral, curing time's employed in the present process are somewhat longer than those conventionally used.
Thus, in general, times from about 15 minutesto about 3 hours are employed to bestadvantages. While the time of cure may be shortened or. lengthened within given limits depending :uponv other variablesssuch as steam temperature, amount of vcatalysts, etc., it is usually preferred to effect cure at times between about 30 minutes and 2 /2 hours.
In order to illustrate the present-invention, the following examples are given by way of illustration. No details or enumerations contained therein should be construed as limitations onthe present invention, except insofar as they appear in the appendedclaims. All parts and percentages are by. weightunless otherwise indicated.
EXAMPLE 1 Pad 'baths were prepared containing 19.0%, 27.5% and 35.0% resin solids of dimethylol ethylene urea and 12% on the weight of the resin solids in ther bath of zinc nitrate or magnesium'chloride as curing accelerators.
l6.l%,. 23f.4%' and 29.6% applications of dimethylol ethylene urea were made on x 80. cotton .percale by padding with the above solutions,'using a pick-up of Y 'Two'methods of curing were used:
A. Dried at 225 F. for 2 minutes and then heated at 350 F. for 1.5 minutes by the standard procedure.
B. The wet fabric was rolled and placed in ,a test tube having a small vent forescape of pressure; 1 The test tube- Wrinkle Recovery Tester following the tentativeTest 1 Method 66-1956 described on page 158 of the 1957Technical; Manualand. .Year Bookv of the American Association of Textile Chemists and Coloristsj vol; 33. ,Thetensilestrength was measured .on a Scott Tester according to A.S.T.M.; standards and the values reported are in. pounds; 3 i
5 The results of these applications are shown in Table I below.
ther illustrates the unique character of zinc salts in the. present invention. Compare with Example 1.
Table 1 Percent Percent Nitrogen Tensile Wrinkle Resin on Catalyst Curing Strength, Recovery Fabric Conditions Pounds Total Orig. Washes 16.1 Zl1(NO3)2- 2. 7 2. 2 52 299 16.1. Zn(NOa)2 2. 5 1.7 74 285 23.4. Zn(Na)a A 3. 7 2. 4 57 311 23.4 Zn(NOa)2- 3. 5 2.2 73 293 23.4. MgOlo 3. 3 2. 6 52 291 23.4 MgClg 3.1 0. 6 94 223 29.6 ZIl(NO3)z 4. 2 2. 6 56 297 29.6 Zn(N,O )g 4.9 2.5 77 285 29.6- MgOlv A" 4.0 2. 6 52 295 29.6- MgOlq B 3. 7 0.6 94 226 The following conclusions may be drawn from these results:
(1) Dimethylol ethylene urea can be cured on the fabric at 210 F. (in steam) with zinc nitrate as a catalyst to obtain approximately normal wrinkle recovery and higher than normal tensile strength. Good fixation of resin is obtained, as indicated by the nitrogen analysis.
(2) Curing under the same conditions with magnesium chloride as the catalyst gives poor fixation of the resin and lower than normal wrinkle recovery. In addition, Table I hereinabove clearly illustrates the merit of the present invention, in that as will be 'seen the conditions of the present process result in wrinkle recoveries substantially as good as are those obtained under normal curing conditions, but with tensile strengths of the order of at least about 70 pounds, which is considerably higher than that normally obtained when wrinkle recovery values of this magnitude are obtained. This tensile strength is of the order of 20 pounds higher than normally obtained for Wrinkle recoveries of this magnitude. In general, it has been found that tensile strength values of the order of at least 80 pounds may be achieved for wrinkle recoveries of 240 and higher, and that for wrinkle recoveries higher than 280 tensile strengths of the order of greater than about 70 pounds are readily achieved by employment of the present process. Such values heretofore have not been possible.
EXAMPLE 2 In separate applications, 17.65% of dimethylol ethylene urea was applied to cotton percale employing varying amounts of well known curing accelerators, based on the weight of resin solids. An 85% wet pick-up was obtained, leaving resin solids on the weight of the fabric. The fabric was then steam cured for 2.5 hours at i 210 F. The applied solutions were as follows.
The results of the applications according to Example 2 are set forth in Table II below.
Table 11 Treatment: Wrinkle recovery (total W-l-F A 175 Untreated 150 No tensile strength determinations were made since they were not warranted in view of the wrinkle recovery obtamed employing these known catalysts. Table II fur- EXAMPLE 3 In separate applications, solutions containing 9.4, 13.5 and 17.65 solids of dimethylol melamine and of dimethylol ether of trimethylol melamine were applied to cotton percale. The solutions contained 1 2% of either mag- 'nesium chloride or zinc nitrate based on the weight of resin solids as catalyst. An wet pick-up was obtained in all cases, leaving the solids content indicated in Table III below on the fabric. The cures identified as A and B in said table are the same as those described in Example 1 hereinabove.
tained. Table IV illustrates the unique character of the cyclic ureas in the present invention. Compare Examples 1 and 3.
' EXAMPLE 4 In separate applications, solutions containing 24.9 and 32.5% (solids basis) of the dimethyl ether of dimethylol urea (UF) was applied to cotton percale employing 12%, based on resin solids, of either magnesium chloride or zinc nitrate as catalyst. An 85% wet pick-up was obtained and the finished fabric cured by the cures identified as A and B in Examples 1 and 2 above. The results are recorded in Table IV below.
Table IV MgOh (N a)2 UF Solids Cure A Cure B Cure A Cure B WR TS WR TS WR TS WR Ts 35:33:32: 3Z3 3:: iii :1: 53% 22 it? it In Table IV above, tensile strength determinations for fabrics having a urea-formaldehyde resin thereon cured with magnesium chloride were deemed unwarranted, since the wrinkle recovery obtained by steam cure was not satisfactory. While good wrinkle recovery can be obtained employing urea-formaldehyde resins by steam cur- '3' ing where a zinc salt is the catalyst, no significant advantage in tensile strength is obtained with respect to those achieved by conventional cure. The present table further demonstrates that the advantages of the present invention are for the most part limited to cyclic ureas "of the type contemplated by the present invention.
While the present invention has been described specifically with respect to the methylol condensates of ring membered cyclic ureas, it isto be understood that the term as it isemployed hereinabove is intended to include their alkylated and in particular their methylated derivatives. Sir1ce alkylationiand particularly methylation are, in general, employed to stabilize aminoplast resins, alkylations of the condensates contemplated in accordance with the present; invention are in general 7 unnecessary, in that thesematerials are themselves sufiiciently stable.
However, should alkylation or methylation be desired, this may be carried out in accordance with the prior art procedures known for the methylation' of aminoplast resins.
Any of the cyclic ureas identified hereinabove or catalysts set forth therein suitable for use in the presentinvention maybe employed singly or in combination with one another, and to some extent with other known teX-' tile finishing resins, as for example, urea-formaldehyde resins and their alkylated derivatives, melamine-formaldehyde resins and their alkylated derivatives, 6-ring memberedcyclic ureas, such as 1,3-propylene urea-formaldehyde, condensates and derivatives thereof, epoxy resins,
such as thediglycidyl ether of ethylene glycol, diglycidyl ether per se and the like guanamine-formaldehyde resins and their alkylated derivatives, acetone-formaldehyde resins and other knowntextile finishing resins wherein their incorporation with the cyclic ureas in accordance with the present invention does not significantly affect the properties sought to be achieved. 7
In addition, it will be apparent that other textile fin-.
ishing assistants may be employed in the. processof the present invention, such as wetting agents, softeners and the like, insofar as their inclusion in the treating bath on the weight of resin solids, v V
4. A method according to claimxl wherein the catalyst is zinc nitrate. V I
5. A process according to: claim-'hwherein the cyclic urea is ethylene urea.
6. A process according to claim v 1, wherein the cyclic urea is 1,2-propylene urea.
7. A'process according to claim 1',x wherein-the curing takes place at a temperature of from between qabout 80 F. to about250 F.
8. A cellulose containingmaterial prepared: by the process of claim 1 having from 1 to 140% based on the'weight of the textile material, of a water-soluble cured formaldehyde condensate of a S-membered cyclic urea thereon and characterized by .high tensile strength and Wrinkle recovery.
9. A cotton textile material prepared by the process of claim 1 having from 1 to 40% based ontheweight of V the textile material ofa cured formaldehyde condensate.
of ethylene urea thereon;
10. A method for treating formed cotton fabric whereby high tensile strength andwrinkle recovery are obtained, which-comprises applying from" an aqueous solution from about 2.5 to about 25% of a formaldehyde condensate. of a S-membered cyclic ureaand a zinc salt of an inorganic acid as a catalyst therefor, said zinc salt being selected from the group consisting of zinc" chloride,
zinc sulfate and zinc nitrate, and'immediately, without intermed1ate drying, wet curing said cyclic urea in the presenceof said zinc salt catalyst in an atmosphere of wet invno way significantly impairs the effect sought to be achieved.
This applicationis a continuation application of application 'Serial No. 796,209, abandoned.
. We. claim:
1. A method of treating cellulose textile material wherefiled March 2, 1959, now
by high tensile strength and wrinkle recovery are ob-- tained, which comprises applying thereto,from anaqueoussolution, a formaldehyde condensate of a S-membered cyclic urea and a zinc saltof an inorganic acidas a catalyst therefor, and immediately, without'intermediate drying, wet curing said cyclic urea in an atmosphere of steam and thereafter drying the so-processed cotton fabric.
' References Cited by-the Examiner UNITED STATES. PATENTS 2,088,227 7/37 Battye etval'." .117 "139.4
2,254,001 8/41 Conway. 2,661,312 12/53 Richardson 117-1394 2,763,574 9/5 Ruperti 117-138.5 2,899,263: 8/59 Nuessle et a1. 117' -139.4 XR 2,917,412 12/59 Reinhardtetial. 117-"-139.4 2,974,065 4/61 WILLIAM D. MARTIN, Primary Examiner. V RICHARD D. NEVIU SQExaminerH Mann er al. 117-145 XR 1 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,177,093 April 6, 1965 William Julius van Loo, Jr. et ale It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected 'below.
Column 1, line 34, for "belaching" read bleaching column 2, line 15, strike out the comma; column 3, line 10, for "ureas" read urea line 34, for "cuprammonium" read cupramonium rayon column 4, line 38, for "catalysts" read catalyst column 7, line 31, after "like" insert a comma Signed and sealed this 5th day of October 1965,
%(SEAL) lAuest:
iERNEST W. SWIDER EDWARD J: BRENNER Attesting Officer 7 Commissioner of Patents
Claims (1)
1. A METHOD OF TREATING CELLULOSE TEXTILE MATERIAL WHEREBY HIGH TENSILE STRENGTH AND WRINGLE RECOVERY ARE OBTAINED, WHICH COMPRISES APPLYING THERETO, FROM AN AQUEOUS SOLUTION, A FORMALDEHYDE CONDENSATE OF A 5-MEMBERED CYCLIC UREA AND A ZINC SALT OF AN INORGANIC ACID AS A CATALYST THEREFOR, AND IMMEDIATELY, WITHOUT INTERMEDIATE DRYING, WET CURING SAID CYCLIC UREA IN AN ATMOSPHERE OF WET STEAM MAINTAINING THE TEXTILE MATERIAL IN THE WET STATE UNTIL COMPLETION OF THE CURE AND THEREAFTER DRYING THE FABRIC.
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Cited By (4)
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US3323939A (en) * | 1964-03-09 | 1967-06-06 | American Cyanamid Co | Process for imparting rot and wrinkle resistant finish to a cellulosic textile material and the resulting textile |
US3409462A (en) * | 1963-12-21 | 1968-11-05 | Pfersee Chem Fab | Process for treating textiles and textiles treated by such process |
US3523033A (en) * | 1968-03-12 | 1970-08-04 | Us Agriculture | Pressure wet-fixation of resins in cellulosic fabrics by the action of heat and pressure |
FR2124332A1 (en) * | 1971-02-01 | 1972-09-22 | Cotton Inc |
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US2899263A (en) * | 1949-08-15 | 1959-08-11 | Eneurea | |
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US2088227A (en) * | 1934-09-19 | 1937-07-27 | Tootal Broadhurst Lee Co Ltd | Impregnation of textile fabrics |
US2254001A (en) * | 1938-11-14 | 1941-08-26 | Du Pont | Textile process |
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US3409462A (en) * | 1963-12-21 | 1968-11-05 | Pfersee Chem Fab | Process for treating textiles and textiles treated by such process |
US3323939A (en) * | 1964-03-09 | 1967-06-06 | American Cyanamid Co | Process for imparting rot and wrinkle resistant finish to a cellulosic textile material and the resulting textile |
US3523033A (en) * | 1968-03-12 | 1970-08-04 | Us Agriculture | Pressure wet-fixation of resins in cellulosic fabrics by the action of heat and pressure |
US3546006A (en) * | 1968-03-12 | 1970-12-08 | Us Agriculture | Wet-fixation process for cellulosic fabrics using low add-ons of resins |
FR2124332A1 (en) * | 1971-02-01 | 1972-09-22 | Cotton Inc |
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