US3041199A - Wrinkle resistant cellulose fabric and method of production - Google Patents
Wrinkle resistant cellulose fabric and method of production Download PDFInfo
- Publication number
- US3041199A US3041199A US44014A US4401460A US3041199A US 3041199 A US3041199 A US 3041199A US 44014 A US44014 A US 44014A US 4401460 A US4401460 A US 4401460A US 3041199 A US3041199 A US 3041199A
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- US
- United States
- Prior art keywords
- fabric
- acid
- urea
- weight
- aldehyde
- 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
- 239000004744 fabric Substances 0.000 title claims description 52
- 238000000034 method Methods 0.000 title claims description 12
- 229920002678 cellulose Polymers 0.000 title description 9
- 239000001913 cellulose Substances 0.000 title description 9
- 230000037303 wrinkles Effects 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 37
- 239000000460 chlorine Substances 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 229920000742 Cotton Polymers 0.000 claims description 10
- 239000007844 bleaching agent Substances 0.000 claims description 9
- 238000002144 chemical decomposition reaction Methods 0.000 claims description 7
- VRKMYKBYPQNBDR-UHFFFAOYSA-N 4-(hydroxymethylamino)-4-oxobutanoic acid Chemical compound OCNC(=O)CCC(O)=O VRKMYKBYPQNBDR-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- -1 alkylene urea Chemical compound 0.000 description 29
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 23
- 239000004202 carbamide Substances 0.000 description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 17
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 239000000835 fiber Substances 0.000 description 16
- 239000004753 textile Substances 0.000 description 16
- 239000007859 condensation product Substances 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000014759 maintenance of location Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229920001187 thermosetting polymer Polymers 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 229920001807 Urea-formaldehyde Polymers 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 230000002939 deleterious effect Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- RCHKEJKUUXXBSM-UHFFFAOYSA-N n-benzyl-2-(3-formylindol-1-yl)acetamide Chemical compound C12=CC=CC=C2C(C=O)=CN1CC(=O)NCC1=CC=CC=C1 RCHKEJKUUXXBSM-UHFFFAOYSA-N 0.000 description 7
- 238000004061 bleaching Methods 0.000 description 6
- 238000010409 ironing Methods 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- PPBYBJMAAYETEG-UHFFFAOYSA-N ethene;formaldehyde;urea Chemical compound C=C.O=C.NC(N)=O PPBYBJMAAYETEG-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000007731 hot pressing Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- SAQWDZHRYAPCHZ-UHFFFAOYSA-N 2-(hydroxymethylcarbamoyl)benzoic acid Chemical compound OCNC(=O)C1=CC=CC=C1C(O)=O SAQWDZHRYAPCHZ-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004902 Softening Agent Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 229920003180 amino resin Polymers 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 2
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 206010003549 asthenia Diseases 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004049 embossing Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 235000019837 monoammonium phosphate Nutrition 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- HMJDPGYDUHLHTM-UHFFFAOYSA-N 2-hydroxy-4-(hydroxymethylamino)-4-oxobutanoic acid Chemical compound C(O)NC(CC(C(=O)O)O)=O HMJDPGYDUHLHTM-UHFFFAOYSA-N 0.000 description 1
- RTTYFXMXRFYCHM-UHFFFAOYSA-N 4-amino-2-hydroxy-4-oxobutanoic acid Chemical compound NC(=O)CC(O)C(O)=O RTTYFXMXRFYCHM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000322338 Loeseliastrum Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940070337 ammonium silicofluoride Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical class NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- 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
- Y10T442/2549—Coating or impregnation is chemically inert or of stated nonreactance
Definitions
- This invention is concerned with improved fibrous webs which have been treated to mitigate deleterious chlorine retention characteristics of the webs. More particularly, the invention is concerned with (a) finished textiles or other fibrous webs which comprise alkylene urea/ aldehyde resins without possessing deleterious chlorine retention properties, (b) new aqueous fabric treating compositions, and (0) methods for the treatment of textiles and other fibrous webs to simultaneously create desirable permanent effects therein and mitigate deleterious chlorine retention properties of the webs.
- the principal object of this invention is the provision ofnew improvements in treated fibrous webs which comprise alkylene urea/ aldehyde resins, but which do not, at the same time, possess deleterious chlorine retention properties. Further objects include:
- R is a radical selected from the group consisting of hydrogen and 1 to 6 carbon alkyl and R is a radical selected from the group consisting of alkylene, hydroxy alkylene and aryl, particularly monocyclic aryl, one to eight carbon alkylene, and one to eight carbon mono or dihydroxy alkylene, and subjecting the web with the applied precondensate and acid to conditions necessary to thermoset the precondensate to form in and on the web a resin finish which is water-insoluble and also insoluble to organic solvents encountered in drycleaning operations.
- fixation of the modifying acid is brought about on the organic fiber is not clear. It may be due to reaction with reactive groups, e.g., hydroxyl groups, in the organic fiber or to interaction with the alkylene urea/aldehyde resin during the thermosetting operation.
- the invention provides for modification of the known finishing of textiles with alkylene urea/ aldehyde resins by the additional fixation in the fabric finish of an N-methylol monoamide of a dicarboxylic acid as aforesaid.
- the modifying acid is conveniently applied to the fibrous web, along with the alkylene urea/aldehyde condensation product and fixed as a part of the finish at the same time as the condensation product is converted to a thermoset material.
- the modifying acid may also be applied separately, before or after, the application of the alkylene urea/ aldehyde material.
- the success of the present invention is due to the discovery that hydrochloric acid degradation of cellulose or other organic fibers finished with amino-aldehyde resins can be reduced or even prevented by the presence in the fabric finish of one of the monoamide acids of this invention.
- This protection against degradation appears to be due to a reaction between the hydrochloric acid set free upon hot pressing and the alkali salt of the acid component, which results in formation of alkali chloride and the fabric-fixed carboxylic acid, which, being a weak acid, does not attack the cellulose as does hydrochloric acid.
- the alkali carboxylate is regenerated and is then ready to protect the fabric against further bleaching treating.
- the cycle can be repeated indefinitely.
- Example 1 A bleached and mercerized cotton plain cloth of grey construction 80 X 80 of 30s/30s is saturated by being immersed in a water solution containing 4.5% of a precondensate of cyclic ethylene urea and formaldehyde,
- the resulting finished cloth is subjected to severe washing followed by three successive treatments in hypochlorite bleach solution and hot ironing. After the third ironing, the tensile strength of the cloth is tested and found to be 2.5% less than the tensile strength of the cloth before the bleaching and ironing treatments.
- the same cloth is treated in the same manner except that the impregnating solution contains no N-methylol succinamic acid.
- the bleached and ironed cloth is found to have lost 45% tensile strength as compared with its strength before the bleaching and ironing.
- Example 2 The procedure of Example 1 is repeated using a water solution containing 30% of a precondensate of urea and formaldehyde, 0.5% of emulsified paraflin wax, 0.25% of non-ionic softening agent, 1% ammonium dihydrogen phosphate and 2% N-methylol phthalamic acid.
- the resulting finished cloth after the bleaching and ironing treatments is found to have a tensile strength loss of 4.8% whereas the cloth finished without the N-methylol phthalamic acid in the solution is found to have a tensile strength loss of 34%.
- the preferred amino-aldehyde resins for use in the present invention include ethylene urea-formaldehyde resins (sec 11.8. 2,373,136 and 2,795,513), and 1,3-propylene urea-formaldehyde resins (see U.S. 2,690,404). Additional examples of cyclic amino organic compound condensation products with aldehydes are found in Us. patents 2,370,839; 2,374,647; 2,700,032; and 2,764,573. Any of the resins referred to in these patents may be used in carrying out the operations of this invention.
- the alkylene urea/ aldehyde condensation product is heat-reactive, i.e., will convert on being heated to a thermoset condition and is applied to the fibrous web in the stage of polymerization or condensation such that it may be dissolved in water.
- the aqueous treating solutions prefer-ably should contain an acidic catalyst.
- Suitable catalysts include free acids, e.g., hydrochloric, citric, phthalic and tartaric acids;a'cid-reacting metal salts, e.g., zinc nitrate, zinc chloride, magnesium chloride, zinc fluoroborate and acidreacting salts of ammonia or amines, e.g., ammonium chloride, ammonium dihydrogen phosphate, ammonium silico fluoride, amino-alkanol hydrohalides and the like.
- free acids e.g., hydrochloric, citric, phthalic and tartaric acids
- a'cid-reacting metal salts e.g., zinc nitrate, zinc chloride, magnesium chloride, zinc fluoroborate
- acidreacting salts of ammonia or amines e.g., ammonium chloride, ammonium dihydrogen phosphate, ammonium silico fluoride, amino-alkanol hydrohalides and the like.
- the amount of the alkylene urea/ aldehyde resin incorporated in the fibrous webs will depend to some extent both on the specific resin used and upon the particular permanent effect desired to be created in the fibrous web. As little as 1% and as great as 50% by Weight of the condensation product based upon the dry weight of the fibrous Web may be employed, depending on the nature of the fibrous Web and the amount and type of permanent effect to be obtained. However, with broadcloth shirting material of cotton and similar relatively lightweight fabrics of cellulosic material, to which the invention is particularly applicable, an alkylene urea/ aldehyde resin concentration of between about 3 and 15% or even up to 25% by Weight is recommended.
- a variety of different modifying acids may be used in accordance with this invention. These acids are the N- methylol derivatives of monoamides of dicarboxylic acids and are readily prepared from the latter by reaction with formaldehyde. While it is preferable to prepare the N- methylol acid before addition to the alkylene urea/aldehyde precondensate, it is possible to add the dicarboxy acid monoamide to the precondensate solution and bring about its reaction with formaldehyde to form the N- methylol derivative either in the solution or on the fibrous web after application of the treating solution.
- N-methylol derivatives of succinamic, phthalamic, hydroxy-succinamic, tartramidic, maleamic and oxamic acids include the N-methylol derivatives of succinamic, phthalamic, hydroxy-succinamic, tartramidic, maleamic and oxamic acids.
- the amount of modifying acid incorporated in the treated fibrous webs may be varied. As previously indicated, the quantity of this material will depend to some extent upon the nitrogenous synthetic resin applied to the textile. Beneficial results against chlorine retention can be obtained with the use of as little as 0.1% by weight of the modifying acid. Satisfactory treated fibrous webs may include 0.1 to 20% by weight of the modifying acid and preferably about 0.1 to 5% by weight and especially 0.1 to 1%. Usually, the ratio of modifying acid to the alkylene urea/aldehyde resin, both in the treating compositions and in the final finished fabric, will be between about 1 to 20 and 1 to 5.
- the webs are dried at a temperature of, for example, 50 to 150 C., and are then heated to convert the active resin-forming material into a thermoset resinous product and fix the modifying acid on the fabric. This is preferably accomplished at a temperature of about to 200 C. for about 1 to 15 minutes. Drying and curing can take place at the same temperature and in the same oven or dryer, if desired. Further, as indicated, the application of the alkylene urea/aldehyde resin and modifying acid can be accom- If accomplished separately, drying and heating should follow each of the solution applications.
- aqueous solutions or dispersions in any other suitable known fashion, e.g., brushing, spraying and the like.
- Fibrous webs which may be operated upon in accordance with the present invention are formed of organic fibers.
- the webs may be in the form of non-woven fabrics, woven fabrics, knitted fabrics or any other similar sheet-like material made up basically of thread-like fibers or structures, whether in the form of a textile or other forms.
- the invention is particularly effective in treatment of webs composed .of fibers of cellulosic origin, e.g., cotton, viscose rayon, linen and the like but also any other fiber liable to be degraded by small amounts of hydrochloric acid are contemplated.
- the invention is also effective in treatment of webs composed partly of fibers of cellulosic origin and partly of other natural or synthetic fibers, e.g., protein fibers such as wool, silk, casein and the like, polyamide fibers, polyester fibers, polyvinyl alcohol fibers, polyacrylonitrile fibers and the like.
- protein fibers such as wool, silk, casein and the like
- polyamide fibers such as wool, silk, casein and the like
- polyester fibers such as polyamide fibers, polyester fibers, polyvinyl alcohol fibers, polyacrylonitrile fibers and the like.
- a resin treated cotton fabric resistant to chemical degradation by chlorine containing bleaching agents having thereon as a finish between about 3 and 15% by weight of ethylene urea-formaldehyde resin and between about 0.1 and 1% by weight of N-methylol succinamic acid. 7
- a resin treated cellulosic fiber fabric resistant to chemical degradation by chlorine containing bleaching agents having thereon as a finish between about 3 and 15% by weight of an aminoplast selected from the group consisting of ethylene urea-formaldehyde resins and 1,3- propylene urea-formaldehyde resins and an acid (I) having a structure selected from the group consisting of:
- R is a radical selected from the group consisting of hydrogen and one to six carbon alkyl and R is a radical selected from the group consisting of alkylene, hydroxy alkylene, and aryl, the ratio of said aminoplast to said acid being between about 20 to 1 and 5 to 1.
- a fabric as claimed in claim 2 wherein said acid is N-methylol succinamic acid.
- a fabric as claimed in claim 2 wherein said acid is N-rnethylol maleamic acid.
- a fabric as claimed in claim 2 wherein said acid is N-methylol phthalamic acid.
- a fabric as claimed in claim 2 wherein said acid is N-methylol hydroxy succinamic acid.
- a processv for finishing cotton fabric to impart Wrinkle-resistance thereto without causing the fabric to be prone to chemical degradation by chlorine containing bleaching agents which comprises impregnating cotton fabric with between about 3 and 15% by weight of a precondensate of ethylene urea and formaldehyde and with between about 0.1 and 1% by weight of N-methylol succinamic acid and heating the impregnated fabric at a temperature between about and 200 C. for between about 1 and 15 minutes to fix the precondensate and acid on the fabric.
- a process for finishing a cellulosic fabric to impart wrinkle-resistance thereto without causing the fabric to be prone to chemical degradation by chlorine containing bleaching agents which comprises impregnating a cellulosic fabric with a cellulose reactant selected from the group consisting of ethylene urea-formaldehyde condensation products and 1,3-propylene urea-formaldehyde condensation products and an acid (I) as defined in claim 2, the ratio of said cellulose reactant to said acid being between about 20 to 1 and 5 to 1, and heating the impregnated fabric at a temperature between about 100 and 200 C. for between about 1 and 15 minutes to said cellulose reactant and fix said acid on the fabric.
- a cellulose reactant selected from the group consisting of ethylene urea-formaldehyde condensation products and 1,3-propylene urea-formaldehyde condensation products and an acid (I) as defined in claim 2
- the ratio of said cellulose reactant to said acid being between about 20 to 1 and 5
- a process of finishing cotton fabric to impart wrinkle-resistance thereto without causing the fabric to be prone to chemical degradation by chlorine containing bleaching agents which comprises impregnating cotton fabric with between about 3 and 15% by weight of a water-soluble cellulose reactant selected from the group consisting of ethylene urea-formaldehyde condensation products and 1,3-propylene urea-formaldehyde condensation products and an acid (1) as defined in claim 4, the ratio of said Water-soluble cellulose reactant to said acid being between about 20 to 1 and 5 to 1, heating the impregnated fabric at a temperature between about 100 and 200 C. for between about 1 and 15 minutes to fix said reactant and acid on the fabric, and thereafter washing the finished fabric in an alkaline solution to convert free carboxy groups in the fabric finish into the corresponding alkali metal car-boxylate.
- a water-soluble cellulose reactant selected from the group consisting of ethylene urea-formaldehyde condensation products and 1,3-propylene urea-formaldehy
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- Chemical & Material Sciences (AREA)
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Description
3,041,199 WRINKLE RESISTANT CELLULOSE FABRIC AND NETHOD F PRODUCTION William S. Miller, Ashton-on-Mersey, and Kenneth Wild,
Middleton, England, assignors to Calico Printers Association, Limited, Manchester, England No Drawing. Filed July 20, 1960, Ser. No. 44,014 Claims. (Cl. 117-62) This invention is concerned with improved fibrous webs which have been treated to mitigate deleterious chlorine retention characteristics of the webs. More particularly, the invention is concerned with (a) finished textiles or other fibrous webs which comprise alkylene urea/ aldehyde resins without possessing deleterious chlorine retention properties, (b) new aqueous fabric treating compositions, and (0) methods for the treatment of textiles and other fibrous webs to simultaneously create desirable permanent effects therein and mitigate deleterious chlorine retention properties of the webs.
It is known to finish textiles by applying thereto condensation products of an aldehyde, commonly formaldehyde, with an amide, commonly urea, thiourea, ethylene urea, propylene urea, guanidine, dicyandiamide,
v melamine and the like and converting said condensation products to the insoluble state in situ. By suitable 'choice of starting materials and processing conditions,
a variety of commercially valuable effects can be obtained, particularly with textiles which are of cellulosic origin. These include improved dimensional stability, improved recovery from creasing, improved fastness of fugitive dyestuffs and durability to washing of mechanical effects such as glazing, embossing, beetling, schreiner ing, pleating and the like. One of the disadvantages of such treatments is, that to varying degree, depending on the choice of starting material and on the manner of application, the nitrogenous resins fixed on the textile material have a tendency to absorb chlorine from bleaching solutions with formation of labile complexes of resin and chlorine. These complexes are broken down when the textile is subsequently heated to temperature as, for example, in hot pressing, some at least of the decomposition product being hydrochloric acid. With cellulosic textiles, loss in strength occurs which may be severe with some resins and less so with others.
- Even with the latter, however, there is a cumulative effect with repeated bleaching and inevitably therefore, the useful life of the fabric is reduced.
The principal object of this invention is the provision ofnew improvements in treated fibrous webs which comprise alkylene urea/ aldehyde resins, but which do not, at the same time, possess deleterious chlorine retention properties. Further objects include:
(1) The provision of new and novel textiles which include resin finishes to impart to the fabrics desirable permanent effects, and also, as a permanent part of the fabric, chemically reactive groups which function during washing of the fabrics with chlorine-containing bleaching agents, and subsequent ironing or hot pressing, to render inactive any hydrochloric acid set free by the elevated temperatures of the hot pressing or ironmg.
(2) The provision of new textile treating compositions which contain a combination of one or more alkylene urea/aldehyde resins with a modifying agent which renders the resin finish which may be formed on textiles from said composition resistant to chemical degradation by chlorine containing bleaching agents.
(3) The provision of new processes for treating textiles or other fibrous webs with alkylene urea/aldehyde resin compositions in order to impart wrinkle resistance and other permanent effects thereto, and, at the same time, mitigating or preventing the simultaneous formation in the webs of deleterious chlorine retention characteristics.
Other objects and further. scope of applicability of the present invention will become apparent from the detailed description given hereinafter; it should be understood, however, that the detailed description, while indicating preferred embodiments of the invention is given by way of illustration only, since various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description.
These object-s are accomplished according to the present invention by applying to a fibrous web of organic fibers a water-soluble, thermosetting alkylene urea/aldehyde precondensate and also an acid having the following structure:
wherein R is a radical selected from the group consisting of hydrogen and 1 to 6 carbon alkyl and R is a radical selected from the group consisting of alkylene, hydroxy alkylene and aryl, particularly monocyclic aryl, one to eight carbon alkylene, and one to eight carbon mono or dihydroxy alkylene, and subjecting the web with the applied precondensate and acid to conditions necessary to thermoset the precondensate to form in and on the web a resin finish which is water-insoluble and also insoluble to organic solvents encountered in drycleaning operations. This results in new treated fibrous webs which do not possess deleterious chlorine retention properties, composed of organic fibers having thereon a water-insoluble, organic solvent-insoluble finish comprising a thermoset, alkylene urea/aldehyde resin and an acid as aforesaid which constitutes a modifying agent for protection of the structure against deleterious effects of chlorine retention.
' The exact mechanism by which fixation of the modifying acid is brought about on the organic fiber is not clear. It may be due to reaction with reactive groups, e.g., hydroxyl groups, in the organic fiber or to interaction with the alkylene urea/aldehyde resin during the thermosetting operation. In any event, the invention provides for modification of the known finishing of textiles with alkylene urea/ aldehyde resins by the additional fixation in the fabric finish of an N-methylol monoamide of a dicarboxylic acid as aforesaid.
The modifying acid is conveniently applied to the fibrous web, along with the alkylene urea/aldehyde condensation product and fixed as a part of the finish at the same time as the condensation product is converted to a thermoset material. However, the modifying acid may also be applied separately, before or after, the application of the alkylene urea/ aldehyde material.
The success of the present invention is due to the discovery that hydrochloric acid degradation of cellulose or other organic fibers finished with amino-aldehyde resins can be reduced or even prevented by the presence in the fabric finish of one of the monoamide acids of this invention. This protection against degradation appears to be due to a reaction between the hydrochloric acid set free upon hot pressing and the alkali salt of the acid component, which results in formation of alkali chloride and the fabric-fixed carboxylic acid, which, being a weak acid, does not attack the cellulose as does hydrochloric acid. When the fabric is later washed in a liquor containing alkali, as in almost all domestic or commercial laundering operations, the alkali carboxylate is regenerated and is then ready to protect the fabric against further bleaching treating. Thus, the cycle can be repeated indefinitely.
A more complete understanding of the new products, compositions and processes of this invention may be had by reference to the following actual examples of operations conducted in accordance with the invention. In these examples, all parts and percentages are by weight unless otherwise specifically indicated.
Example 1 A bleached and mercerized cotton plain cloth of grey construction 80 X 80 of 30s/30s is saturated by being immersed in a water solution containing 4.5% of a precondensate of cyclic ethylene urea and formaldehyde,
' 0.5% of emulsified parafiin wax, 0.25% of a non-ionic softening agent, 1% of ammonium chloride and 0.5% of N-methylol succinamic aoid. After impregnation, the cloth is mangled so that it retains 80% of its own weight of impregnating solution. It is then dried in hot air (100 C.), following which it is heated for five minutes at 130 C. Finally, the finished cloth is Washed for five minutes at 50 C. in Water containing 0.1% sodium carbonate, rinsed in clear water and dried.
The resulting finished cloth is subjected to severe washing followed by three successive treatments in hypochlorite bleach solution and hot ironing. After the third ironing, the tensile strength of the cloth is tested and found to be 2.5% less than the tensile strength of the cloth before the bleaching and ironing treatments.
' In another case, the same cloth is treated in the same manner except that the impregnating solution contains no N-methylol succinamic acid. In this case, the bleached and ironed cloth is found to have lost 45% tensile strength as compared with its strength before the bleaching and ironing.
Example 2 The procedure of Example 1 is repeated using a water solution containing 30% of a precondensate of urea and formaldehyde, 0.5% of emulsified paraflin wax, 0.25% of non-ionic softening agent, 1% ammonium dihydrogen phosphate and 2% N-methylol phthalamic acid.
The resulting finished cloth after the bleaching and ironing treatments is found to havea tensile strength loss of 4.8% whereas the cloth finished without the N-methylol phthalamic acid in the solution is found to have a tensile strength loss of 34%.
The preferred amino-aldehyde resins for use in the present invention include ethylene urea-formaldehyde resins (sec 11.8. 2,373,136 and 2,795,513), and 1,3-propylene urea-formaldehyde resins (see U.S. 2,690,404). Additional examples of cyclic amino organic compound condensation products with aldehydes are found in Us. patents 2,370,839; 2,374,647; 2,700,032; and 2,764,573. Any of the resins referred to in these patents may be used in carrying out the operations of this invention.
The alkylene urea/ aldehyde condensation product is heat-reactive, i.e., will convert on being heated to a thermoset condition and is applied to the fibrous web in the stage of polymerization or condensation such that it may be dissolved in water. In order to aid in thermosetting or curing the condensation products to a water-insoluble and organic solvent insoluble stage, once applied to the fibrous web, the aqueous treating solutions prefer-ably should contain an acidic catalyst. A Wide variety of such materials have been developed and are known for use in catalyzing the curing of amino-aldehyde condensation products. Examples of suitable catalysts include free acids, e.g., hydrochloric, citric, phthalic and tartaric acids;a'cid-reacting metal salts, e.g., zinc nitrate, zinc chloride, magnesium chloride, zinc fluoroborate and acidreacting salts of ammonia or amines, e.g., ammonium chloride, ammonium dihydrogen phosphate, ammonium silico fluoride, amino-alkanol hydrohalides and the like.
plished simultaneously or in separate steps.
Other examples of suitable acid catalysts will be found in the disclosures of the patents referred to above. Usually, 1 to 10% by weight of the catalyst based upon the weight of the initial alkylene urea/ aldehyde condensation product is an effective amount for use in the operations of this invention.
The amount of the alkylene urea/ aldehyde resin incorporated in the fibrous webs will depend to some extent both on the specific resin used and upon the particular permanent effect desired to be created in the fibrous web. As little as 1% and as great as 50% by Weight of the condensation product based upon the dry weight of the fibrous Web may be employed, depending on the nature of the fibrous Web and the amount and type of permanent effect to be obtained. However, with broadcloth shirting material of cotton and similar relatively lightweight fabrics of cellulosic material, to which the invention is particularly applicable, an alkylene urea/ aldehyde resin concentration of between about 3 and 15% or even up to 25% by Weight is recommended.
A variety of different modifying acids may be used in accordance with this invention. These acids are the N- methylol derivatives of monoamides of dicarboxylic acids and are readily prepared from the latter by reaction with formaldehyde. While it is preferable to prepare the N- methylol acid before addition to the alkylene urea/aldehyde precondensate, it is possible to add the dicarboxy acid monoamide to the precondensate solution and bring about its reaction with formaldehyde to form the N- methylol derivative either in the solution or on the fibrous web after application of the treating solution.
Specific examples of compounds which may be used as the modifying acids for the purposes of this invention include the N-methylol derivatives of succinamic, phthalamic, hydroxy-succinamic, tartramidic, maleamic and oxamic acids. Also, the N-methylol monoamides of malonic; adipic; sebacic; terephthalic; 2,4-hexadienedioic; fumaric; 2,2'-diphenic; dimethyl malonic; phenyl succinic; [3,,8-diphenyl isosuccinic; a-methyl, (if-phenyl succinic; {i s-dimethyl glutaric and fl-phenyl glutaconic acids. Mixtures of two or more of the modifying acids may be used.
The amount of modifying acid incorporated in the treated fibrous webs may be varied. As previously indicated, the quantity of this material will depend to some extent upon the nitrogenous synthetic resin applied to the textile. Beneficial results against chlorine retention can be obtained with the use of as little as 0.1% by weight of the modifying acid. Satisfactory treated fibrous webs may include 0.1 to 20% by weight of the modifying acid and preferably about 0.1 to 5% by weight and especially 0.1 to 1%. Usually, the ratio of modifying acid to the alkylene urea/aldehyde resin, both in the treating compositions and in the final finished fabric, will be between about 1 to 20 and 1 to 5.
Once the aqueous treating solutions or dispersions have been applied to the fibrous webs, the webs are dried at a temperature of, for example, 50 to 150 C., and are then heated to convert the active resin-forming material into a thermoset resinous product and fix the modifying acid on the fabric. This is preferably accomplished at a temperature of about to 200 C. for about 1 to 15 minutes. Drying and curing can take place at the same temperature and in the same oven or dryer, if desired. Further, as indicated, the application of the alkylene urea/aldehyde resin and modifying acid can be accom- If accomplished separately, drying and heating should follow each of the solution applications.
No special equipment or unusual procedural methods are required for applying the treating compositions to fibrous webs. Thus, established padding or impregnation procedures may be used and these may be carried out in standard textile processing equipment. Likewise, the drying and heatingmay be carried out on standard textile handling apparatus. Furthermore, these fibrous web treattextile processing procedures such as water-proofing, calendering, embossing, pressing and the like. Other known finishing agents such as sizing agents, softeners, lubrieating material, water-repellent agents, moth-proofing agents, mildew-proofing agents, dyes, pigments and the like may be applied simultaneously or concurrently with the treating material of this invention. Since the alkylene urea/ aldehyde resins as referred to can also serve as fixing agents for dyestuffs, treatment of the fabrics as described can be used in conjunction with established dyeing or coloring operations.
In addition to padding or immersion of the fibrous webs in the described aqueous treating compositions in order to apply the treating materials to the fibrous webs, it is possible to apply the aqueous solutions or dispersions in any other suitable known fashion, e.g., brushing, spraying and the like.
Fibrous webs which may be operated upon in accordance with the present invention are formed of organic fibers. The webs may be in the form of non-woven fabrics, woven fabrics, knitted fabrics or any other similar sheet-like material made up basically of thread-like fibers or structures, whether in the form of a textile or other forms. The invention is particularly effective in treatment of webs composed .of fibers of cellulosic origin, e.g., cotton, viscose rayon, linen and the like but also any other fiber liable to be degraded by small amounts of hydrochloric acid are contemplated. The invention is also effective in treatment of webs composed partly of fibers of cellulosic origin and partly of other natural or synthetic fibers, e.g., protein fibers such as wool, silk, casein and the like, polyamide fibers, polyester fibers, polyvinyl alcohol fibers, polyacrylonitrile fibers and the like.
Having provided a complete description of the invenout the invention, the scope of patent protection to be granted the'invention is defined by the following claims.
We claim:
1. A resin treated cotton fabric resistant to chemical degradation by chlorine containing bleaching agents having thereon as a finish between about 3 and 15% by weight of ethylene urea-formaldehyde resin and between about 0.1 and 1% by weight of N-methylol succinamic acid. 7
2. A resin treated cellulosic fiber fabric resistant to chemical degradation by chlorine containing bleaching agents having thereon as a finish between about 3 and 15% by weight of an aminoplast selected from the group consisting of ethylene urea-formaldehyde resins and 1,3- propylene urea-formaldehyde resins and an acid (I) having a structure selected from the group consisting of:
wherein R is a radical selected from the group consisting of hydrogen and one to six carbon alkyl and R is a radical selected from the group consisting of alkylene, hydroxy alkylene, and aryl, the ratio of said aminoplast to said acid being between about 20 to 1 and 5 to 1.
3. A fabric as claimed in claim 2 wherein said acid is N-methylol succinamic acid.
4. A fabric as claimed in claim 2 wherein said acid is N-rnethylol maleamic acid.
5. A fabric as claimed in claim 2 wherein said acid is N-methylol phthalamic acid.
6. A fabric as claimed in claim 2 wherein said acid is N-methylol hydroxy succinamic acid.
7. A processv for finishing cotton fabric to impart Wrinkle-resistance thereto without causing the fabric to be prone to chemical degradation by chlorine containing bleaching agents which comprises impregnating cotton fabric with between about 3 and 15% by weight of a precondensate of ethylene urea and formaldehyde and with between about 0.1 and 1% by weight of N-methylol succinamic acid and heating the impregnated fabric at a temperature between about and 200 C. for between about 1 and 15 minutes to fix the precondensate and acid on the fabric.
8. A process as claimed in claim 7 wherein the heat treated fabric is washed in an alkaline solution to convert free carboxy groups in the'fabric finish to corresponding alkali metal carboxylate.
9. A process for finishing a cellulosic fabric to impart wrinkle-resistance thereto without causing the fabric to be prone to chemical degradation by chlorine containing bleaching agents which comprises impregnating a cellulosic fabric with a cellulose reactant selected from the group consisting of ethylene urea-formaldehyde condensation products and 1,3-propylene urea-formaldehyde condensation products and an acid (I) as defined in claim 2, the ratio of said cellulose reactant to said acid being between about 20 to 1 and 5 to 1, and heating the impregnated fabric at a temperature between about 100 and 200 C. for between about 1 and 15 minutes to said cellulose reactant and fix said acid on the fabric.
10. A process of finishing cotton fabric to impart wrinkle-resistance thereto without causing the fabric to be prone to chemical degradation by chlorine containing bleaching agents which comprises impregnating cotton fabric with between about 3 and 15% by weight of a water-soluble cellulose reactant selected from the group consisting of ethylene urea-formaldehyde condensation products and 1,3-propylene urea-formaldehyde condensation products and an acid (1) as defined in claim 4, the ratio of said Water-soluble cellulose reactant to said acid being between about 20 to 1 and 5 to 1, heating the impregnated fabric at a temperature between about 100 and 200 C. for between about 1 and 15 minutes to fix said reactant and acid on the fabric, and thereafter washing the finished fabric in an alkaline solution to convert free carboxy groups in the fabric finish into the corresponding alkali metal car-boxylate.
References Cited in the file of this patent UNITED STATES PATENTS 2,377,866 DAlelio June 12, 1945 2,898,238 Van Loo et al. Aug. 4, 1959 2,957,746 Buck et a1. Oct. 25, 1960
Claims (1)
- 7. A PROCESS FOR FINISHING COTTON FABRIC TO IMPART WRINKLE-RESISTANCE THERETO WITHOUT CAUSING THE FABRIC TO BE PRONE TO CHEMICAL DEGRADATION BY CHLORINE CONTAINING BLEACHING AGENTS WHICH COMPRISES IMPREGNATING COTTON FABRIC WITH BETWEEN ABOUT 3 AND 15% BY WEIGHT OF A PRECONDENSATE OF ETHYLENE UREA AND FORMALDEHYDE AND WITH BETWEEN ABOUT 0.1 AND 1% BY WEIGHT OF N-METHYLOL SUCCINAMIC ACID AND HEATING THE IMPREGNATED FABRIC AT A TEMPERATURE BETWEEN ABOUT 100* AND 200*C. FOR BETWEEN ABOUT 1 AND 15 MINUTES TO FIX THE PRECONDENSATE AND ACID ON THE FABRIC.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44014A US3041199A (en) | 1960-07-20 | 1960-07-20 | Wrinkle resistant cellulose fabric and method of production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44014A US3041199A (en) | 1960-07-20 | 1960-07-20 | Wrinkle resistant cellulose fabric and method of production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3041199A true US3041199A (en) | 1962-06-26 |
Family
ID=21930071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US44014A Expired - Lifetime US3041199A (en) | 1960-07-20 | 1960-07-20 | Wrinkle resistant cellulose fabric and method of production |
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| Country | Link |
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| US (1) | US3041199A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3300273A (en) * | 1963-06-24 | 1967-01-24 | Russell M H Kullman | Production of cellulosic materials with oxidizing power |
| US3304147A (en) * | 1963-06-24 | 1967-02-14 | Robert M Reinhardt | Method of making cellulosic materials with oxidizing power |
| US3465036A (en) * | 1964-07-07 | 1969-09-02 | American Cyanamid Co | 2-carboxyethoxymethyl-tris (2-(n-methylolcarbamoyl)-ethoxymethyl) methane |
| US3849169A (en) * | 1971-11-04 | 1974-11-19 | Grace W R & Co | Method for producing wrinkle free permanently pressed cellulosic textile materials |
| US3933426A (en) * | 1972-10-07 | 1976-01-20 | Ciba-Geigy Corporation | Process for making textiles containing cellulose crease-resistant |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2377866A (en) * | 1940-08-02 | 1945-06-12 | Gen Electric | Aminoplasts having intercondensed therein a partial amide of a polycarboxylic acid |
| US2898238A (en) * | 1956-08-20 | 1959-08-04 | American Cyanamid Co | Process for treating textiles with ethylene urea-formaldehyde reaction products |
| US2957746A (en) * | 1957-01-11 | 1960-10-25 | Nat Cotton Council Of America | Process of inducing a crease into creaseproofed cellulose fabrics by treating with an acid catalyst and hot pressing a crease in the treated area |
-
1960
- 1960-07-20 US US44014A patent/US3041199A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2377866A (en) * | 1940-08-02 | 1945-06-12 | Gen Electric | Aminoplasts having intercondensed therein a partial amide of a polycarboxylic acid |
| US2898238A (en) * | 1956-08-20 | 1959-08-04 | American Cyanamid Co | Process for treating textiles with ethylene urea-formaldehyde reaction products |
| US2957746A (en) * | 1957-01-11 | 1960-10-25 | Nat Cotton Council Of America | Process of inducing a crease into creaseproofed cellulose fabrics by treating with an acid catalyst and hot pressing a crease in the treated area |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3300273A (en) * | 1963-06-24 | 1967-01-24 | Russell M H Kullman | Production of cellulosic materials with oxidizing power |
| US3304147A (en) * | 1963-06-24 | 1967-02-14 | Robert M Reinhardt | Method of making cellulosic materials with oxidizing power |
| US3465036A (en) * | 1964-07-07 | 1969-09-02 | American Cyanamid Co | 2-carboxyethoxymethyl-tris (2-(n-methylolcarbamoyl)-ethoxymethyl) methane |
| US3849169A (en) * | 1971-11-04 | 1974-11-19 | Grace W R & Co | Method for producing wrinkle free permanently pressed cellulosic textile materials |
| US3852829A (en) * | 1971-11-04 | 1974-12-10 | Grace W R & Co | Composition and method for producing wrinkle-free permanently pressed cellulosic textile materials |
| US3933426A (en) * | 1972-10-07 | 1976-01-20 | Ciba-Geigy Corporation | Process for making textiles containing cellulose crease-resistant |
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