US2165265A - Process of imparting hydrophobic properties to cellulose fibers - Google Patents
Process of imparting hydrophobic properties to cellulose fibers Download PDFInfo
- Publication number
- US2165265A US2165265A US81122A US8112236A US2165265A US 2165265 A US2165265 A US 2165265A US 81122 A US81122 A US 81122A US 8112236 A US8112236 A US 8112236A US 2165265 A US2165265 A US 2165265A
- Authority
- US
- United States
- Prior art keywords
- fibers
- acid
- cellulose fibers
- solution
- formaldehyde
- 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
- 229920003043 Cellulose fiber Polymers 0.000 title description 11
- 238000000034 method Methods 0.000 title description 8
- 230000002209 hydrophobic effect Effects 0.000 title description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 19
- 239000000835 fiber Substances 0.000 description 17
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 12
- 229920000297 Rayon Polymers 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- -1 aliphatic aldehyde Chemical class 0.000 description 10
- 229920002955 Art silk Polymers 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 239000004310 lactic acid Substances 0.000 description 6
- 235000014655 lactic acid Nutrition 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 239000005871 repellent Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000007824 aliphatic compounds Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000008149 soap solution Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- PEMYVTWKMAMYEH-UHFFFAOYSA-N 1-aminononadecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCCCCCCC(N)S(O)(=O)=O PEMYVTWKMAMYEH-UHFFFAOYSA-N 0.000 description 1
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 1
- HPKUCQQHPHAOBZ-UHFFFAOYSA-N 1-heptadecyl-1-octadecylurea Chemical compound C(CCCCCCCCCCCCCCCCC)N(C(=O)N)CCCCCCCCCCCCCCCCC HPKUCQQHPHAOBZ-UHFFFAOYSA-N 0.000 description 1
- GKFPQWDKGDLIIE-UHFFFAOYSA-N 2,3-bis(4-methylpentyl)phenol Chemical compound C(CCC(C)C)C=1C(=C(C=CC1)O)CCCC(C)C GKFPQWDKGDLIIE-UHFFFAOYSA-N 0.000 description 1
- KHTJRKQAETUUQH-UHFFFAOYSA-N 2-(hydroxymethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCC(CO)C(N)=O KHTJRKQAETUUQH-UHFFFAOYSA-N 0.000 description 1
- CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
- MQBITTBZTXUIPN-UHFFFAOYSA-N 2-methylpropylurea Chemical compound CC(C)CNC(N)=O MQBITTBZTXUIPN-UHFFFAOYSA-N 0.000 description 1
- WAPXOSBOKUVUAS-UHFFFAOYSA-N 3-(octadecylamino)-2,6,8-trioxo-7,9-dihydropurine-1-carbonitrile Chemical compound C(CCCCCCCCCCCCCCCCC)NN1C(N(C(C=2NC(NC1=2)=O)=O)C#N)=O WAPXOSBOKUVUAS-UHFFFAOYSA-N 0.000 description 1
- PBGIBVPVUBXIKS-UHFFFAOYSA-N 3-chloro-2,6,8-trioxo-7,9-dihydropurine-1-carbonitrile Chemical compound ClN1C(N(C(C=2NC(NC1=2)=O)=O)C#N)=O PBGIBVPVUBXIKS-UHFFFAOYSA-N 0.000 description 1
- GVHSESMJDQCNGP-UHFFFAOYSA-N 36-aminohexatriacontan-18-one Chemical compound CCCCCCCCCCCCCCCCCC(=O)CCCCCCCCCCCCCCCCCCN GVHSESMJDQCNGP-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000009990 desizing Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- WRNOAELBRPKVHC-UHFFFAOYSA-N dodecylurea Chemical compound CCCCCCCCCCCCNC(N)=O WRNOAELBRPKVHC-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- OHOPIZUOANPWQS-UHFFFAOYSA-N n-butyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCCC OHOPIZUOANPWQS-UHFFFAOYSA-N 0.000 description 1
- LCTOXAHEDJCUII-UHFFFAOYSA-N n-carbamoyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC(N)=O LCTOXAHEDJCUII-UHFFFAOYSA-N 0.000 description 1
- HNUFCQUTJXHEPI-UHFFFAOYSA-N n-methyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC HNUFCQUTJXHEPI-UHFFFAOYSA-N 0.000 description 1
- MYSPBSKLIFPWDI-UHFFFAOYSA-N octacosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(N)=O MYSPBSKLIFPWDI-UHFFFAOYSA-N 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- GJNDMSSZEBNLPU-UHFFFAOYSA-N octadecylurea Chemical compound CCCCCCCCCCCCCCCCCCNC(N)=O GJNDMSSZEBNLPU-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/425—Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/402—Amides imides, sulfamic acids
- D06M13/432—Urea, thiourea or derivatives thereof, e.g. biurets; Urea-inclusion compounds; Dicyanamides; Carbodiimides; Guanidines, e.g. dicyandiamides
-
- 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
-
- 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
- D06M15/41—Phenol-aldehyde or phenol-ketone resins
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/17—Glyoxal and polyaldehyde treatment of textiles
-
- 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
- Y10T428/2904—Staple length fiber
- Y10T428/2907—Staple length fiber with coating or impregnation
Definitions
- the present invention relates to a process of imparting hydrophobic properties to cellulose fibers.
- fibers of cellulose or hydrated 5 cellulose such as cotton, artificial silk or staple fiber are extraordinarily hydrophil, that is to say they are very quickly wetted when in contact with water. This property is a great disadvantage for many of the applications of this material.
- This invention consists in a process for making cellulose fibers hydrophobe by applying to the fibers or incorporating with them a compound which contains at least one aliphatic or cycloaliphatic residue having at least 4 carbon atoms and capable of reacting with aldehyde and exposing the fibers thus treated simultaneously or subsequently to the action of an aliphatic aldehyde or dialdehyde, for instance, formaldehyde or glyoxal.
- Suitable aliphatic compounds are, for example,
- fatty amines and fatty acid amides such as dodecylamine, hexadecylamine, octadecenylamine, abietic acid amide, lauric acid amide, stearoyl-methylamide, stearoyl-butylamide, stearoyloctadecylamide; further compounds of the character of alkyl-substituted ureas having the general formula:
- R. stands for a radical selected from the group consisting of aliphatic and cycloaliphatic radicals containing at least 4 carbon atoms
- X 35 stands for a member selected from the group consisting of O, NH, N. alkyl
- R1 stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals, such as mono-isobutyl urea, monododecyl urea, monooctadecyl urea, stearoyl urea; further fatty acid imino ethers or arnidines.
- hydroxyl groups such as, for instance, dodecylphenol, diisohexyl-phenol.
- the cellulose fibers are first saturated with a solution of the aliphatic compound in an organic solvent, for instance, pyridine, or acetone 55 or in an aqueous emulsion of the aliphatic compounds. They are then dried and exposed to the atcion of, for instance, formaldehyde, the concentration of which, when it is used in the form of a solution, must not be more than 5%.
- formaldehyde may be added to the impregnating solution so that a subsequent treatment with formaldehyde becomes unnecessary; however, care must likewise be taken that the concentration of the aldehyde, for instance, of the formaldehyde, in the treating solution is not more than 5%. In this case the fiber needs only subsequent heating to ensure sufiicient reaction of the formaldehyde with the impregnating compound and the fiber.
- an acid medium there may be added, for example, to the aqueous emulsion, acetic acid, lactic acid or agents of acid reaction such' as sodium bisulfite.
- Fibers treated in this manner are characterized by a particularly high stability towards-water and even hot soap solution.
- such material can be subjected to the usual fulling treatment, that is to say heating for A; hour in a. solution of 50 grams of soap and 5 grams of sodium carbonate per liter at 50 C. without loss of the property of repellent water.
- the parent material and working conditions an effect can be obtained which is not notably diminished by several washings with boiling soap solution.
- Another process of rendering cellulose fibers water-repellent consists in treating the fibers with solutions or dispersions of the aldehyde condensation products.
- a catalyst an acid substance is suitably added to the solutions or dispersions.
- the fibers may also be pretreated withan acid substance.
- the said aldehyde condensation products may also be added directly to the spinning solutions from which the artifical cellulose threads are prepared.
- the fibers which are prepared from solutions containing such an addition may, if required, be treated subsequently with an aldehyde.
- the silk is then drained, dried, immersed for 5 minutes in aqueous formaldehyde solution of 30 per cent. strength, centrifuged, dried and heated for 16 hours at C.
- aqueous formaldehyde solution of 30 per cent. strength
- centrifuged dried and heated for 16 hours at C.
- the fibrous material may be suspended for hour in a chamber charged with formaldehyde vapor at C.
- octadecyl-heptadecyl urea another of the substances specified above may be used.
- Unsoaped dry viscose silk is immersed for 5 minutes in 10 times its weight of an aqueous emulsion containing 2 per cent. of stearin-amide, 0.2 per cent. of an emulsifying agent, obtainable by the reaction of ethylene-oxide with octadecenyl-alcohol, and0.3 per cent. of formaldehyde.
- the goods are centrifuged, dried and heated for 6 hours at 110 C. A subsequent washing is not necessary.
- Unsoaped, dry viscose silk is immersed for 5 minutes in 5 times its weight of a solution of 5-10 per cent. strength of methylol-stearinamide in pyridine.
- the goods are centrifuged, dried and heated for 15 hours at 110 C.
- Example 4 The operation is conducted as described in Example 2 but 7 per cent. of lactic acid is added to the emulsion. By this addition of acid the stability of the water repelling preparation is strongly increased, particularly towards treatment with boiling dilute acid.
- Dry viscose artificial silk is treated for 15 minutes with a solution of 5 grams of a condensation product, obtainable from stearic acid amide and aqueous formaldehyde, in 1 liter of carbon tetrachloride.
- the material is squeezed and dried in the air. Thereupon it is aftertreated at room temperature for 15 minutes with [I a solution of 5 grams of lactic acid in 1 liter of water, squeezed, dried in a current of air and heated for 2 hours at 110 C. The material is finally well rinsed and dried.
- Viscose artificial silk tissue is treated for 10 minutes with an aqueous solution of the sodium salt of stearyl aminomethanesulfonic acid or stearylmethylaminomethanesulfonic acid, 5 grams of lactic acid being added per liter.
- the material is squeezed and dried at a temperature of 40 C. to 50 C.
- the tissue is then heated for 5-10 minutes at a temperature of C. to C.
- cellulose fibers of all kinds for instance, copper artificial silk, artificial spinning fibers, cotton, also mixtures of wool and cellulose fibers as well as fabrics made from the said fibers and mixtures of fibers may be used. In some cases a preliminary cleansing or desizing of the fibers or fabric is advisable.
- R star ids for a radical selected from the group consisting of aliphatic and ,cycloali phatic radicals containing at least 4 carbon atoms
- X stands for a member selected from the group consisting of O, NH, N.alkyl
- R1 stands for a member of the group consisting of hydrogen and, aliphatic hydrocarbon radicals, at most 5 per cent. of aldehyde and an agent of acid action, and heating them after the impregnation.
- R stands for a radical selected from the group consisting of aliphatic and cycloaliphatic radicals, containing at least '4 carbon atoms, x
- R1 stands for a radical selected from the group consisting of O, NH, N.alkyl and R1 stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals, treating the fibers with aliphatic aldehydes and subsequently heating them.
- R stands for a radical selected from the group consisting of aliphatic and cycloaliphatic radicals containing at least 4 carbon atoms,'X
- R stands for a radical selected from the group consisting of aliphatic and cycloaliphatic radicals containing at least 4 carbon atoms
- X stands for a radical selected from the group consisting of 0, NH, N.alky1
- R1 stands for a member of the group consisting of hydrogen and aliphatic hydrocarbon radicals, in the presence of an agent of acid action, and heating them after the impregnation.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI52329D DE762964C (de) | 1935-05-12 | 1935-05-12 | Verfahren zum Wasserabweisendmachen von Cellulosefasern |
| DE2111698X | 1935-09-28 | ||
| DE485593X | 1935-11-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2165265A true US2165265A (en) | 1939-07-11 |
Family
ID=32045547
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US81122A Expired - Lifetime US2165265A (en) | 1935-05-12 | 1936-05-21 | Process of imparting hydrophobic properties to cellulose fibers |
| US102300A Expired - Lifetime US2111698A (en) | 1935-05-12 | 1936-09-24 | Process or preparing hydrophobic cellulose fibers |
| US166224A Expired - Lifetime US2211976A (en) | 1935-05-12 | 1937-09-28 | Process of imparting hydrophobic properties to cellulose fibers |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US102300A Expired - Lifetime US2111698A (en) | 1935-05-12 | 1936-09-24 | Process or preparing hydrophobic cellulose fibers |
| US166224A Expired - Lifetime US2211976A (en) | 1935-05-12 | 1937-09-28 | Process of imparting hydrophobic properties to cellulose fibers |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US2165265A (sl) |
| BE (3) | BE415480A (sl) |
| DE (1) | DE762964C (sl) |
| FR (3) | FR806170A (sl) |
| GB (4) | GB463300A (sl) |
| NL (3) | NL45055C (sl) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2446864A (en) * | 1944-06-26 | 1948-08-10 | Quaker Chemical Products Corp | Composition and process for imparting durable water repellent finish to textiles |
| US2507700A (en) * | 1946-11-27 | 1950-05-16 | Monsanto Chemicals | N, n', n''-triacylmelamines |
| US2510522A (en) * | 1944-12-09 | 1950-06-06 | Montclair Res Corp | Textile treating products and process of making |
| US2562161A (en) * | 1948-02-06 | 1951-07-31 | Cluett Peabody & Co Inc | Stabilization of regenerated cellulose fabric with glyoxal-amide reaction product |
| US2565194A (en) * | 1947-03-27 | 1951-08-21 | American Cyanamid Co | Chlorotriazine resins and process of making the same |
| US2608494A (en) * | 1948-08-28 | 1952-08-26 | Walkden Makin & Co Ltd | Treatment of textile fabrics for imparting antishrink properties thereto |
| US2641558A (en) * | 1948-12-24 | 1953-06-09 | Nat Lead Co | Water repellence fixative treatment |
| US3128272A (en) * | 1957-06-11 | 1964-04-07 | Minnesota Mining & Mfg | Perfluoroalkyl-substituted triazines |
| US3190763A (en) * | 1960-12-17 | 1965-06-22 | Hoechst Ag | Process for the anti-static finishing of high molecular weight compounds |
| US4289665A (en) * | 1977-12-23 | 1981-09-15 | Cassella Aktiengesellschaft | Process for the preparation of aqueous emulsions, stable in storage, of N.alkyl-N-alkylol-ureas and their application for the softening of leather |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE907163C (de) * | 1938-06-07 | 1954-03-22 | Hoechst Ag | Verfahren zum Wasserabstossendmachen von natuerlichen Faserstoffen tierischer oder pfanzlicher Herkunft oder kuenstlichen Faserstoffen |
| US2423185A (en) * | 1939-07-08 | 1947-07-01 | Hydronapthene Corp | Process for the manufacture of coated and impregnated materials |
| DE766083C (de) * | 1940-01-26 | 1954-02-01 | Ig Farbenindustrie Ag | Mittel zum Veredeln von Faserstoffen |
| US2418696A (en) * | 1942-03-09 | 1947-04-08 | Courtaulds Ltd | Modifying the dyeing properties of cellulose or cellulose derivative textile materials |
| US2451426A (en) * | 1943-11-25 | 1948-10-12 | Du Pont | Bright zinc plating |
| NL60268C (sl) * | 1944-08-14 | 1947-11-15 | ||
| US2431202A (en) * | 1945-03-01 | 1947-11-18 | Gen Aniline & Film Corp | Self-dispersing methylolstear-amides |
| US2594384A (en) * | 1946-11-12 | 1952-04-29 | Monsanto Chemicals | Fungi and bacteria resistant papermakers' felts and process for preparing same |
| US2540726A (en) * | 1946-12-03 | 1951-02-06 | Du Pont | Treatment of a heat set, oriented nylon fabric with formaldehyde |
| BE480227A (sl) * | 1947-08-14 | |||
| US2574114A (en) * | 1948-04-26 | 1951-11-06 | Bozel Maletra Prod Chimiques | Amide-glyoxal-formaldehyde reaction product and shrinkproofing cellulose textile fibers therewith |
| US2600698A (en) * | 1948-11-13 | 1952-06-17 | Monsanto Chemicals | Reaction products from an aldehyde, an aminotriazine, and a mono-nheterocyclic compound |
| US2805196A (en) * | 1952-02-11 | 1957-09-03 | Tno | Permselective electrodialysis |
| NL114029C (sl) * | 1958-02-20 | |||
| US3232697A (en) * | 1959-07-01 | 1966-02-01 | Nalco Chemical Co | Textile treatment |
| US3112155A (en) * | 1962-02-02 | 1963-11-26 | Sidney L Vail | Glyoxal-amide reaction products |
| US4103051A (en) * | 1975-11-03 | 1978-07-25 | Milliken Research Corporation | Pilling reduction in textiles |
| US4295930A (en) * | 1980-03-17 | 1981-10-20 | Nalco Chemical Company | Alkoxylated dioxolanes as paper sizing agents |
| US4563288A (en) * | 1982-08-03 | 1986-01-07 | Colgate-Palmolive Company | N-Alkyl isostearamide antistatic agents, detergent compositions containing such agents, and processes for washing laundry in the presence of such agents, and with such compositions |
| US4497715A (en) * | 1982-08-03 | 1985-02-05 | Colgate-Palmolive Company | N-Alkylisostearamides as antistatic agents |
| US7713215B2 (en) * | 2008-01-31 | 2010-05-11 | Shriver Edgar L | Steering, piercing, anchoring, distending extravascular guidewire |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE219848C (sl) * | 1906-04-24 | |||
| AT118595B (de) * | 1926-12-01 | 1930-07-25 | Tootal Broadhurst Lee Co Ltd | Verfahren zum Imprägnieren von Textilgarnen, Geweben und Stoffen mit synthetischen Harzen. |
| DE542186C (de) * | 1929-06-14 | 1932-01-21 | Alexander Nathansohn Dr | Verfahren zum Wasserfestmachen von rohen, chemisch nicht gereinigten Textilfaserstoffen |
| FR751641A (fr) * | 1932-02-29 | 1933-09-07 | Ig Farbenindustrie Ag | Procédé pour la préparation de produits de condensation auxiliaire |
| AT136377B (de) * | 1933-01-13 | 1934-01-25 | Heberlein & Co Ag | Veredlungsverfahren für vegetabilische Textilien. |
-
0
- BE BE418549D patent/BE418549A/xx unknown
- BE BE417657D patent/BE417657A/xx unknown
-
1935
- 1935-05-12 DE DEI52329D patent/DE762964C/de not_active Expired
- 1935-06-21 GB GB17898/35A patent/GB463300A/en not_active Expired
- 1935-06-21 GB GB4212/37A patent/GB463472A/en not_active Expired
- 1935-11-08 GB GB30934/35A patent/GB467166A/en not_active Expired
-
1936
- 1936-05-06 NL NL77672A patent/NL45055C/xx active
- 1936-05-11 BE BE415480D patent/BE415480A/xx unknown
- 1936-05-11 FR FR806170D patent/FR806170A/fr not_active Expired
- 1936-05-21 US US81122A patent/US2165265A/en not_active Expired - Lifetime
- 1936-09-22 NL NL79327A patent/NL44056C/xx active
- 1936-09-24 US US102300A patent/US2111698A/en not_active Expired - Lifetime
- 1936-09-28 FR FR47692D patent/FR47692E/fr not_active Expired
- 1936-11-23 FR FR813868D patent/FR813868A/fr not_active Expired
- 1936-11-23 GB GB32028/36A patent/GB485593A/en not_active Expired
-
1937
- 1937-09-28 US US166224A patent/US2211976A/en not_active Expired - Lifetime
-
1938
- 1938-03-31 NL NL87184A patent/NL50083C/xx active
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2446864A (en) * | 1944-06-26 | 1948-08-10 | Quaker Chemical Products Corp | Composition and process for imparting durable water repellent finish to textiles |
| US2510522A (en) * | 1944-12-09 | 1950-06-06 | Montclair Res Corp | Textile treating products and process of making |
| US2507700A (en) * | 1946-11-27 | 1950-05-16 | Monsanto Chemicals | N, n', n''-triacylmelamines |
| US2565194A (en) * | 1947-03-27 | 1951-08-21 | American Cyanamid Co | Chlorotriazine resins and process of making the same |
| US2562161A (en) * | 1948-02-06 | 1951-07-31 | Cluett Peabody & Co Inc | Stabilization of regenerated cellulose fabric with glyoxal-amide reaction product |
| US2608494A (en) * | 1948-08-28 | 1952-08-26 | Walkden Makin & Co Ltd | Treatment of textile fabrics for imparting antishrink properties thereto |
| US2641558A (en) * | 1948-12-24 | 1953-06-09 | Nat Lead Co | Water repellence fixative treatment |
| US3128272A (en) * | 1957-06-11 | 1964-04-07 | Minnesota Mining & Mfg | Perfluoroalkyl-substituted triazines |
| US3190763A (en) * | 1960-12-17 | 1965-06-22 | Hoechst Ag | Process for the anti-static finishing of high molecular weight compounds |
| US4289665A (en) * | 1977-12-23 | 1981-09-15 | Cassella Aktiengesellschaft | Process for the preparation of aqueous emulsions, stable in storage, of N.alkyl-N-alkylol-ureas and their application for the softening of leather |
Also Published As
| Publication number | Publication date |
|---|---|
| GB463300A (en) | 1937-03-22 |
| BE418549A (sl) | |
| DE762964C (de) | 1953-11-30 |
| US2111698A (en) | 1938-03-22 |
| US2211976A (en) | 1940-08-20 |
| GB467166A (en) | 1937-06-08 |
| NL50083C (sl) | 1941-04-15 |
| BE417657A (sl) | |
| NL44056C (sl) | 1938-09-15 |
| FR47692E (fr) | 1937-06-16 |
| NL45055C (sl) | 1939-02-15 |
| FR806170A (fr) | 1936-12-09 |
| BE415480A (sl) | 1936-06-30 |
| GB463472A (en) | 1937-03-22 |
| GB485593A (en) | 1938-05-23 |
| FR813868A (fr) | 1937-06-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2165265A (en) | Process of imparting hydrophobic properties to cellulose fibers | |
| US2284895A (en) | Treatment of textiles to impart water-repellence | |
| US2370405A (en) | Process for rendering material water-repellent and products therefrom | |
| US2205120A (en) | Process for rendering cellulosecontaining material crease-resistant and products obtained thereby | |
| GB842402A (en) | Process for fixing aminoplasts in the wet state on fibrous materials | |
| US2926063A (en) | Cellulose anthranilate textile fibers and process for making the same | |
| US3676053A (en) | Method of modifying fibrous materials | |
| US2313742A (en) | Process of treating textile fiber | |
| US2302777A (en) | Process of matting textiles | |
| US2294435A (en) | Process for rendering textiles water-repellent | |
| US2173029A (en) | Process for rendering textiles water-repellent and products therefrom | |
| US2303363A (en) | Process for rendering textiles water-repellent and product therefrom | |
| US2322333A (en) | Improving fastness of dyeings | |
| US2207740A (en) | Process for producing water-repellent cellulose-containing materials and products therefrom | |
| ES256483A1 (es) | Procedimiento para la preparaciën de derivados de amino plastos | |
| US2270893A (en) | Process of imparting hydrophobic properties to fibrous materials | |
| US2191982A (en) | Water repellent textile material | |
| US2786735A (en) | Process for producing cyanoethylated native cotton fibers by reacting cellulose fibers with acrylonitrile in vapor phase | |
| US2289275A (en) | Process of waterproofing textiles | |
| US3918903A (en) | Dehydration process to impart wrinkle resistance to cellulose-containing fibrous materials | |
| US2906776A (en) | Impregnating agent | |
| US2282701A (en) | Process of waterproofing | |
| US2297731A (en) | Processes for rendering textiles water repellent | |
| US2380133A (en) | Process for rendering textiles water-repellent | |
| US3234043A (en) | Process for treating fibrous materials and resulting products |