US2301676A - Water-repellent textile material and a process of preparing it - Google Patents
Water-repellent textile material and a process of preparing it Download PDFInfo
- Publication number
- US2301676A US2301676A US27703439A US2301676A US 2301676 A US2301676 A US 2301676A US 27703439 A US27703439 A US 27703439A US 2301676 A US2301676 A US 2301676A
- Authority
- US
- United States
- Prior art keywords
- stands
- group
- textile material
- acid
- water
- 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
- 239000000463 material Substances 0.000 title description 49
- 239000004753 textile Substances 0.000 title description 33
- 238000000034 method Methods 0.000 title description 15
- 239000005871 repellent Substances 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 description 18
- 239000004744 fabric Substances 0.000 description 17
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 239000007859 condensation product Substances 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- 229920000297 Rayon Polymers 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- -1 halogen alkyl compound Chemical class 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229920002955 Art silk Polymers 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 239000004890 Hydrophobing Agent Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002657 fibrous material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000005070 ripening Effects 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001595582 Octolasmis cor Species 0.000 description 2
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 238000004078 waterproofing Methods 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 description 1
- MKTYYYJWTPFTKB-UHFFFAOYSA-N 2,2-dichlorooctadecanamide Chemical compound ClC(C(=O)N)(CCCCCCCCCCCCCCCC)Cl MKTYYYJWTPFTKB-UHFFFAOYSA-N 0.000 description 1
- WWCCKLDZXKPCGQ-UHFFFAOYSA-N 8-methyl-2-phenoxynonanamide Chemical compound C(CCCCC(C)C)C(C(=O)N)OC1=CC=CC=C1 WWCCKLDZXKPCGQ-UHFFFAOYSA-N 0.000 description 1
- 101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- 101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000000047 abietol derivative Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 159000000013 aluminium salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical compound OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 101150111293 cor-1 gene Proteins 0.000 description 1
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- FMXLGOWFNZLJQK-UHFFFAOYSA-N hypochlorous acid;zirconium Chemical compound [Zr].ClO FMXLGOWFNZLJQK-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- LRZFEBJUJIQVDQ-UHFFFAOYSA-N methyl 2-(dimethylamino)acetate Chemical compound COC(=O)CN(C)C LRZFEBJUJIQVDQ-UHFFFAOYSA-N 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JHOKTNSTUVKGJC-UHFFFAOYSA-N n-(hydroxymethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCO JHOKTNSTUVKGJC-UHFFFAOYSA-N 0.000 description 1
- HNUFCQUTJXHEPI-UHFFFAOYSA-N n-methyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC HNUFCQUTJXHEPI-UHFFFAOYSA-N 0.000 description 1
- NOSILEXHUBACKG-UHFFFAOYSA-N n-octadecylacetamide Chemical compound CCCCCCCCCCCCCCCCCCNC(C)=O NOSILEXHUBACKG-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
- VJQGGZWPOMJLTP-UHFFFAOYSA-N octadecane-1,1-diol Chemical compound CCCCCCCCCCCCCCCCCC(O)O VJQGGZWPOMJLTP-UHFFFAOYSA-N 0.000 description 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
- IULGYNXPKZHCIA-UHFFFAOYSA-N octadecyl carbamate Chemical compound CCCCCCCCCCCCCCCCCCOC(N)=O IULGYNXPKZHCIA-UHFFFAOYSA-N 0.000 description 1
- FJSKBPJWQNFYKM-UHFFFAOYSA-N octadecyl n-methylcarbamate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)NC FJSKBPJWQNFYKM-UHFFFAOYSA-N 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 229950005308 oxymethurea Drugs 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—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
-
- 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
-
- 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
- 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
- Y10T442/2164—Coating or impregnation specified as water repellent
- Y10T442/2197—Nitrogen containing
Definitions
- the present invention relates to water-repellent textile material and to a process-of preparing it.
- Ra stands for hydrogen or an alkyl radical
- Ra for a low molecular aliphatic hydrocarbon radical which may, if desired, be substituted by halogen
- Y stands for a readily exchangeable halogen atom or the group R4 and R5 being aliphatic hydrocarbon radicals or R4 and R5 together standing for an alkylene radical with 4 or 5 carbon atoms or an alkylene radical with 4wcarbon atoms, being interrupted by oxygen, for instance, Y may stand for the groups CHr-CH:
- CHrCHa CHg-CHI to react with a tertiary alphatic or heterocyclic base or with a halogen alkyl compound, and then subjecting the impregnated fibrous material to a heat treatment at temperatures between and C.
- R, R1, R2, X, X1 and Ra have the aboveindicated meaning
- Hal means a halogen atom
- Z means that at the pentavalent nitrogen atom three aliphatic hydrocarbon radicals are attached or that this nitrogen atom is a member of an unsaturated heterocyclic ring system or a member of a saturated heterocyclic ring system, in which latter case an aliphatic hydrocarbon radical is also bound to the nitrogen atom.
- As compounds suitable for use in the present process there may, for instance, be named: The quaternary ammonium salts of pyridine with the ester-like condensation products from salts of chloracetic acid and the halogen-methyl derivatives of the following compounds: dodecylalcohol, hexadecylalcohol, octadecylalcohol, oleylalcohol, naphthene alcohols, montan alcohol, abietinols and the hydrogenation products thereof, octadecane-diol, 9.10-dichlorc-octadecanol, octadecyl-monoglycolether, para-butylphenylbutanol, octadecylphenylglycol ether, dodecylmercaptan, octadecyl-mercaptan, lauric acid amide, palmitic acid amide, stearic
- the process consists in impregnating the textile material with a solution or dispersion of the hydrophobing agent, removing the excess of the treating liquid by squeezing or centrifuging the material and exposing the material thus treated for some time to a temperature of 80 C. to 150 C. (ripening).
- the degree of the ripening temperature required for obtaining the desired eflect depends upon the kind of the hydrophobing agent used. In some cases. it may be preferable first to pro-dry the impregnated material at a low temperature and subsequently to heat it at a highertemperature.
- the water-proofing action of the products used in the present process may be increased by simultaneously using for the impregnation condensation products of the series of the so-called condensation resins, such as condensation products from urea, thio-urea, phenol, aniline, molemine, dicyanidiamide and the like with aidehydes, especially with formaldehyde and glyoxal.
- the fibrous material acquires a con siderabie resistance to creasing in addition to the improved waterproofing.
- a viscose artificial sill; fabric is impregnated with an aqueous solution of l per cent strength of the compound:
- the material is then freed, by centrifugi irom the excess solution and heated, for half an hour, at a temperature of C. to C.
- the fabric becomes, to a high degree, impermeable to water and immediately repels water dropped thereon. This efiect is not changed, even when the material has been washed several times.
- a cotton fabric is treated, for 10 minutes, with an aqueous solution of 1 per cent strength of the compound:
- the fabric is then freed, by centrifuging, from the excess of the adhering solvent and heated, for
- Muslin-delaine is introduced into an aqueous solution containing per litre 1.5 grams of the compound:
- the material After squeezing, the material is heated, for one hour. at 80 C. to 90 C.
- Viscose artificial silk is treated, for a short time, with an aqueous solution or 1 nor cent strength of the product:
- a mixed fabric consisting of wool and staple fiber (50:50) is treated with an aqueous solution containing per liter 15 grams of the product:
- the material is then squeezed and exposed, for one hour, to a temperature of 105 C.
- a fabric from cuprammonium artificial silk isimpregnated with an aqueous solution of 2 per cent strength of the, compound:
- the fabric After removal of the excess solvent, the fabric is exposed, for one hour, to a temperature of 120 C.
- Viscose artificial silk is treated, at 60 C. to 70 C., with an aqueous dispersion of 1 per cent strength of a mixture consisting of equal parts of stearic acid methylol amide and the compound:
- the material is freed, by squeezing, from the excess solution and then heated, for half an hour, at 105 C. to 110 C.
- a fabric made from viscose staple fiber is passed through a bath containing per liter 10 grams of the compound:
- Viscose artificial silk crepe is impregnated with an aqueous solution containing per liter 5 grams of melamine, 5 grams of lactic acid, 30 cc.
- the fabric is then centrifuged and heated, for half an hour, at 135 C.
- a fabric made from viscose stapleflber is treated, at 20 C. 'to 25 C., with an aqueous dispersion containing per liter 3 grams of sodium carbonate, 16.5 grams of crystallized sodium acetate, 24 grams of zirconium-hydroxy chloride and 10 grams of the compound:
- a viscose artificial silk fabric is impregnated with a solution of l per cent strength of the compound:
- the material After the material has been freed by centrifuging from the excess of the solution it is dried at 40 C. to C. and then heated, for 10 minutes, at a temperature of 135 C. to 140 C.
- the fabric becomes, to a high degree, impermeable to water and immediately repels water dropped thereon. This effect is not changed, even when the material has been washed several times.
- a cotton fabric is impregnated with a solution of 1 per cent strength of the compound:
- the fabric After the fabric has been freed, by centrifuging, from the excess of solution, it is dried at 40 C. to 50 C. and thereupon heated, for 30 minutes, at a temperature of 135 C. to 140 C.
- the fabric becomes, to a high degree, impermeable to water and immediately repels water dropped thereon. This effect is not changed, even when the material has been washed several times.
- Xi stands for a member of the group consisting of R3 stands for a member of the group consisting of hydrogen and alkyl radicals; R: stands for a member of the group consisting of low molecular aliphatic hydrocarbon radicals and low molecu lar aliphatic hydrocarbon radicals substituted by halogen; Hal means halogen; NEZ stands for a member of the group consisting of tertiary aliphatic amines, tertiary heterocyclic bases alkyl GHQ-05, N ⁇
- Water-repellent textile material obtained by impregnating a textile material with a quaternary ammonium salt of one of the general formulae of the group consisting of wherein R stands fora radical of at least 11 carbon atoms selected from the group consisting of aliphatic, aliphatic-cycloaliphatic and araliphatic radicals and aliphatic, aliphaticmember of the group consisting of tertiary aliphatic amines, tertiary heterocyclic bases,
- condensation product from an aldehyde and a member of the group consisting of urea, thiourea, phenol, aniline, melamine,-dicyandiamide and a quaternary ammonium salt as defined in claim 4.
- X1 stands for amember oi the group consisting of and O CON formulae of the group consisting of R.X.CH2.O.COR:C1
- R stands for a radical of at least 11 carbon atoms selected from the group consisting of aliphatic, aliphatic-cycloaliphatic and araliphatic radicals and aliphatic, aliphaticcycloaliphatic and araliphatic radicals containand ing hetero-atoms as members of their carbon structure;
- R1 stands for an alkyl radical;
- x stands for a member of the group consisting of oxygen, sulfur,
- x1 stands for a member of the group consisting Hal means halogen; NEZ stands for a 7 and 0CON/ ing the textile material to a temperature between about 80 C. and about 150 C.
- -0CON X1 stands for a member of the group consisting of -CON /R and 0 0 ON
- R stands for a member of the group consisting of hydrogen and alkyl radicals
- R stands for stands for a member of the group consisting of oxygen, sulfur,
- -0 ON and -0CON Xl stands for a member of the group consisting of --CON ⁇ and -OCON
- Ra stands for a member of the group consisting of hydrogen and alkyl radicals
- R2 stands for a member of thegroup consistingof low molecular aliphatic hydrocarbon radicals substituted by halogen
- Hal means halogen
- NEZ stands for a member of the group consisting of tertiary aliphatic amines, tertiary heterocyclic bases,
- R stands for a radical of at least 11 carbon atoms selected from the group consisting of aliphatic, aliphatic-cycloaliphatic and araliphatic radicals and aliphatic, aliphaticcycloaliphatic and araliphatic radicals containing hetero-atoms as members of their carbon structure;
- Rl stands for an alkyl radical;
- X stands' for a member of the group consisting of oxygen, sulfur,
- x1 stands for a member of the group consisting of and 00 ON 8: stands for a member of the group consisting of hydrogen and alkyl radicals; R: stands for a member of the group consisting of low molecular aliphatic hydrocarbon radicals and low molecular aliphatic hydrocarbon radicals substituted by halogen: Hal means halogen: NEZ stands for a member oi the group consisting oi tertiary aliphatic amines, tertiary heterocyclic bases.
- Water-repellent textile material obtained by impregnating a textile material with a quaternary ammonium salt of the general formula:
- fi air aliphatic radical oi at least 12 carbon atoms
- X stands for a member oi the group consistingoi'oxygen
- sulfur Ra Ra Ra stands for a member of the group. consisting of hydrogen and alkyl radicals
- Ra stands for a member of the group consisting of low molecular aliphatic hydrocarbon radicals and low molecular aliphatic hydrocarbon radicals substituted by halogen
- NEZ stands for a member of the group consisting of tertiary aliphatic amines.
- alkyl era-cm CH:- H
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Patented Nov. 10, 1942 UNITED STATES PATENT OFFICE WATEB-REPELLENT TEXTILE MATERIAL ANP A PROCESS OF PREPARING IT 'tlon of Delaware No Drawing. Application June 2, 1939, Serial No. 277,034. In Germany June 7, 1938 15 Claims.
The present invention relates to water-repellent textile material and to a process-of preparing it.
We have found that natural or artificial fibro material of animal or vegetable origin and threads and fabrics made thereof may be rendered water-repellent by treating them with solutions or dispersions of quaternary ammonium salts obtainable by causing ester-like constituted compounds corresponding with one of the gen eral formulae:
Ra stands for hydrogen or an alkyl radical, Ra for a low molecular aliphatic hydrocarbon radical which may, if desired, be substituted by halogen, Y stands for a readily exchangeable halogen atom or the group R4 and R5 being aliphatic hydrocarbon radicals or R4 and R5 together standing for an alkylene radical with 4 or 5 carbon atoms or an alkylene radical with 4wcarbon atoms, being interrupted by oxygen, for instance, Y may stand for the groups CHr-CH:
CHrCHa CHg-CHI to react with a tertiary alphatic or heterocyclic base or with a halogen alkyl compound, and then subjecting the impregnated fibrous material to a heat treatment at temperatures between and C.
The manufacture of the quaternary ammonium salts used for treating the fibrous materials by the process of the present invention is described in the copending U. S. patent application, Serial No. 273,042, filed May 11, 1939, by Gerhard Balle, Johann Rosenbach and Ludwig Orthner, for Quaternary ammonium salts and process of preparing them.
The quaternary ammonium salts thus produced correspond with one of the general formulae:
RnXpCHg. 0.0 O Rg.NEZ
wherein R, R1, R2, X, X1 and Ra have the aboveindicated meaning, Hal means a halogen atom and Z means that at the pentavalent nitrogen atom three aliphatic hydrocarbon radicals are attached or that this nitrogen atom is a member of an unsaturated heterocyclic ring system or a member of a saturated heterocyclic ring system, in which latter case an aliphatic hydrocarbon radical is also bound to the nitrogen atom.
"As compounds suitable for use in the present process there may, for instance, be named: The quaternary ammonium salts of pyridine with the ester-like condensation products from salts of chloracetic acid and the halogen-methyl derivatives of the following compounds: dodecylalcohol, hexadecylalcohol, octadecylalcohol, oleylalcohol, naphthene alcohols, montan alcohol, abietinols and the hydrogenation products thereof, octadecane-diol, 9.10-dichlorc-octadecanol, octadecyl-monoglycolether, para-butylphenylbutanol, octadecylphenylglycol ether, dodecylmercaptan, octadecyl-mercaptan, lauric acid amide, palmitic acid amide, stearic acid amide, oleic acid amide, stearic acid methylamide, montanic acid amide, resinic acid amide, amides of the carboxylic acids obtainable by oxidation of paramn withat least 12 carbon atoms, furthermore: dichlorostearic acid amide, ricinoleic acid methylamide, acetic acid-N-octadecylamide, iso-octylphenoxy acetic acid amide, isododecylcyclohexyl-hydroxy-acetic acid amide corresponding with the formula:
tributylphenoxy-acetic acid butylamide.
There may further be used in the present process the products of reaction of pyridine with the condensation products from sodium chloracetate and the halogen-methyl derivatives of carbamic acid dodecyl ester, carbamic acidhexadecyl ester, carbamic acid octadecyl ester, N-methylcarbamic acid octadecyl ester and carbamic acid-isododecylphenyl ester.
There may further'benamed the products of reaction of pyridine with the products of reaction of salts of chloracetic acid and halogenmethyl derivatives from compounds of high molecular weight containing a nitrilo-grcup and formaldehyde, in the presence of hydrogen halides, such as, for instance, contained in the condensation product from heptadecylmitrile and formaldehyde in the presence of hydrochloric acid.
There may also he used in this invention com== pounds obtainable by causing the above-named chloroinethyl compounds to react, in an analogous manner, with salts of other halogen-mar boxylic acids containing an easily exchangeable halogen atom, for instance the salts of dichiow acetic acid, bromacetic acid and chloropropionic acid.
instead oi. the above-mentioned pyridiniurn salts there may likewise be used ammonium salts which are formed when the pyridine is exchanged for another tertiary base, such as, for instance, the homologues of pyridine, quinoline, trimethyl= amine, dimethylaminoacetic acid methyl ester, N w methylmorpholine, tetramethylethylenediamine.
The process consists in impregnating the textile material with a solution or dispersion of the hydrophobing agent, removing the excess of the treating liquid by squeezing or centrifuging the material and exposing the material thus treated for some time to a temperature of 80 C. to 150 C. (ripening). The degree of the ripening temperature required for obtaining the desired eflect depends upon the kind of the hydrophobing agent used. In some cases. it may be preferable first to pro-dry the impregnated material at a low temperature and subsequently to heat it at a highertemperature.
A special advantage is obtained, is some cases, by impregnating the textile material in the presence of agents having a feebly acid action, such as lactic acid, tartaric acid, glycolic acid, boric acid or the like. Frequently it is possible, thereby, to shorten the subsequent heat treatment or to obtain a suflicient eflfect though applying a considerably lower ripening temperature. ment of the textile material with agents having an acid action may also be performed before or after the impregnation.
It is, in many cases, of' advantage, to use the above-named compounds in admixture with other hydrophobing agents, such as parafiin, aluminium salts, zirconium salts, the methylola'mides of acids of high molecular weight, isocyanates of high-molecular weight or the addition compounds of halogen-methyl ethers or halogen-methyl amides of high-molecular weight to tertiary bass-s, and the ester-like condensation products .of salts of the halogen-cairboxylic acids with halogen-methyl derivatives of alcohols,
The treatamides and the like of high-molecular weight, which have already been mentioned above as in= termediate products for the manufacture of the treating agents used in this invention.
It has, furthermore, been found that in some cases the water-proofing action of the products used in the present process may be increased by simultaneously using for the impregnation condensation products of the series of the so-called condensation resins, such as condensation products from urea, thio-urea, phenol, aniline, molemine, dicyanidiamide and the like with aidehydes, especially with formaldehyde and glyoxal. In this case, the fibrous material acquires a con siderabie resistance to creasing in addition to the improved waterproofing.
The following examples serve to illustrate the invention but they are not inmnded to limit it thereto:
1. A viscose artificial sill; fabric is impregnated with an aqueous solution of l per cent strength of the compound:
The material is then freed, by centrifugi irom the excess solution and heated, for half an hour, at a temperature of C. to C. By this treatment, the fabric becomes, to a high degree, impermeable to water and immediately repels water dropped thereon. This efiect is not changed, even when the material has been washed several times.
2. A cotton fabric is treated, for 10 minutes, with an aqueous solution of 1 per cent strength of the compound:
The material is then suueezed and heated, for half an hour, at C. to ld0 C; After this treatment, the material is very water-=repellent.
3. Woollen piece goods are impregnated with an aqueous solution or 2 per cent strength of the product:
The fabric is then freed, by centrifuging, from the excess of the adhering solvent and heated, for
one hour, at 90 C. to 100 C.
4. Muslin-delaine is introduced into an aqueous solution containing per litre 1.5 grams of the compound:
After squeezing, the material is heated, for one hour. at 80 C. to 90 C.
5. Viscose artificial silk is treated, for a short time, with an aqueous solution or 1 nor cent strength of the product:
. impregnated with a solution of 2 per cent strength of the compound:
(32m /CH| Gumbo-oleo.NoH,.o.oo.cm-N om All CH:
After centrifuging, it is heated, for half an hour, at a temperature of 125 C.
8. A mixed fabric consisting of wool and staple fiber (50:50) is treated with an aqueous solution containing per liter 15 grams of the product:
The material is then squeezed and exposed, for one hour, to a temperature of 105 C.
9. A fabric from cuprammonium artificial silk isimpregnated with an aqueous solution of 2 per cent strength of the, compound:
on, I on.
C.ilHI1.0.CH1.0.C0.CH-NCH2-CHz.O.CHa
After removal of the excess solvent, the fabric is exposed, for one hour, to a temperature of 120 C.
10. Viscose artificial silk is treated, at 60 C. to 70 C., with an aqueous dispersion of 1 per cent strength of a mixture consisting of equal parts of stearic acid methylol amide and the compound:
The material is freed, by squeezing, from the excess solution and then heated, for half an hour, at 105 C. to 110 C.
12. A fabric made from viscose staple fiber is passed through a bath containing per liter 10 grams of the compound:
5 grams of tartaric acid and 100 grams of dimethylolurea. After centrifuging, the fabric is heated, for'one hour, at 140 C.,
13. Viscose artificial silk crepe is impregnated with an aqueous solution containing per liter 5 grams of melamine, 5 grams of lactic acid, 30 cc.
of a formaldehyde solution of 35 per cent strength and 10 grams of the product:
The fabric is then centrifuged and heated, for half an hour, at 135 C.
14. A fabric made from viscose stapleflber is treated, at 20 C. 'to 25 C., with an aqueous dispersion containing per liter 3 grams of sodium carbonate, 16.5 grams of crystallized sodium acetate, 24 grams of zirconium-hydroxy chloride and 10 grams of the compound:
/CH| CiSHI'I-O.GH:.O.C0-CHi-N-CHI C] CH: After squeezing, the material is exposed, for half an hour, to a temperature of 135 C. to 140 C.
15. A viscose artificial silk fabric is impregnated with a solution of l per cent strength of the compound:
After the material has been freed by centrifuging from the excess of the solution it is dried at 40 C. to C. and then heated, for 10 minutes, at a temperature of 135 C. to 140 C. By this treatment, the fabric becomes, to a high degree, impermeable to water and immediately repels water dropped thereon. This effect is not changed, even when the material has been washed several times.
16. A cotton fabric is impregnated with a solution of 1 per cent strength of the compound:
CisH31O.CHz.O.CO.CH.CI.N(CH3) 01 After the fabric has been freed, by centrifuging, from the excess of solution, it is dried at 40 C. to 50 C. and thereupon heated, for 30 minutes, at a temperature of 135 C. to 140 C. By this treatment, the fabric becomes, to a high degree, impermeable to water and immediately repels water dropped thereon. This effect is not changed, even when the material has been washed several times.
We claim:
1. The process of manufacturing water-repellent textile material which comprises impregnating the textile material with a liquor containing a quaternary ammonium salt of one of the general formulae of the group consisting of R.X.CH,.O.COR1.NEZ
Hal
and
Rail. CH2. 0. c 0 Rm'zz Hal CON
Xi stands for a member of the group consisting of R3 stands for a member of the group consisting of hydrogen and alkyl radicals; R: stands for a member of the group consisting of low molecular aliphatic hydrocarbon radicals and low molecu lar aliphatic hydrocarbon radicals substituted by halogen; Hal means halogen; NEZ stands for a member of the group consisting of tertiary aliphatic amines, tertiary heterocyclic bases alkyl GHQ-05, N\
CH:- Ha alkyl CHr-CHa and alkyl CHPC l. and drying said impregnated textile material.
2. A modification of the process described in claim 1 which consists in treating the textile material with an acid agent before impregnating it with the liquor containing the quaternary ammonium salt.
3. A modification of the process described in claim 1 which consists in treating the textile material with an acid agent after impregnating it with the liquor containing the quaternary ammonium salt.
4. Water-repellent textile material obtained by impregnating a textile material with a quaternary ammonium salt of one of the general formulae of the group consisting of wherein R stands fora radical of at least 11 carbon atoms selected from the group consisting of aliphatic, aliphatic-cycloaliphatic and araliphatic radicals and aliphatic, aliphaticmember of the group consisting of tertiary aliphatic amines, tertiary heterocyclic bases,
alkyl I UHF-C alkyl GHZCHS CHa tile material impregnated with an acid agent,
a condensation product from an aldehyde and a member of the group consisting of urea, thiourea, phenol, aniline, melamine,-dicyandiamide and a quaternary ammonium salt as defined in claim 4.
8. The process of manufacturing water-repellent textile material which comprises impregnating the textile material with a liquor containing a quaternary ammonium salt which has been prepared from ester-like constituted compounds corresponding with one of the general cycloaliphatic and araliphatic radicals containing hetero-atoms as members of their carbon structure; R1 stand for an alkyl radical; X stands for a member of the group consisting of oxygen, sulfur,
X1 stands for amember oi the group consisting of and O CON formulae of the group consisting of R.X.CH2.O.COR:C1
wherein R stands for a radical of at least 11 carbon atoms selected from the group consisting of aliphatic, aliphatic-cycloaliphatic and araliphatic radicals and aliphatic, aliphaticcycloaliphatic and araliphatic radicals containand ing hetero-atoms as members of their carbon structure; R1 stands for an alkyl radical; x stands for a member of the group consisting of oxygen, sulfur,
x1 stands for a member of the group consisting Hal means halogen; NEZ stands for a 7 and 0CON/ ing the textile material to a temperature between about 80 C. and about 150 C.
9. The process of manufacturing water-repellent textile material which comprises impregnating the textile material with a liquor containing an acid agent and a quaternary ammonium salt of one of the general formulae of the group consisting of R.X.CH3.().CORLNEZ and RLXLCHl-O-CORl-NEZ wherein R stands for a radical of at least 11 carbon atoms selected from the group consisting of aliphatic, aliphatic-cycloa'liphatic and araliphatic radicals and aliphatic, aliphaticcycloaliphatic and araliphatic radicals containing hetero-atoms as" members of their carbon structure; R1 stands for an alkyl radical; X
I 5 ing of aliphatic, aliphatic-cycloaliphatic and araliphatic radicals and aliphatic, aliphaticcycloaliphatic and araliphatic radicals containing hetero-atoms as members of their carbon structure; Rl stands for an alkyl radical; X stands for a member of the group consisting of oxygen, sulfur,
and -0CON X1 stands for a member of the group consisting of -CON /R and 0 0 ON R: stands for a member of the group consisting of hydrogen and alkyl radicals; R: stands for stands for a member of the group consisting of oxygen, sulfur,
-0 ON and -0CON Xl stands for a member of the group consisting of --CON\ and -OCON Ra stands for a member of the group consisting of hydrogen and alkyl radicals; R2 stands for a member of thegroup consistingof low molecular aliphatic hydrocarbon radicals substituted by halogen; Hal means halogen; NEZ stands for a member of the group consisting of tertiary aliphatic amines, tertiary heterocyclic bases,
CHr-C H:
and
alkyl i om-orll CHr-CH:
and drying said impregnated textile material.
10. The process of manufacturing water-repellent textile material which comprises impregnating the textile material with a liquor containing a condensation product from an aldehyde and a member of the group consisting of urea, thiourea, phenol, aniline, melamine, dicyandiamide and a quaternary ammonium salt of one of the general formulae of the group consisting of R.X.CH.O.COR.I-IIZ Hal and Rbxl- CH1. 0 C O Rl-NEZ wherein It stands for a radical of at least 11 carbon atoms selected from the group consista member of the group consisting of low molecular aliphatic hydrocarbon radicals and low molecular aliphatic hydrocarbon radicals substituted by halogen; Hal means halogen; NEZ stands for a member of the group consisting of tertiary aliphatic amines, tertiary heterocyclic bases,
and
and drying said impregnated textile material.
11. The process of manufacturing water-repellent textile material which comprises impregnating the textile material with a liquor containing an acid agent, a condensation product from an aldehyde and a member of the group consisting of urea, thiourea, phenol, aniline, melamine, dicyandiamide, and a quaternary ammonium salt of one of the general formulea of the group consisting of 11.x. 03.0.0 0 R.NZ
al and Rl.Xl.C HI- 0. C O Rl-NEZ wherein R stands for a radical of at least 11 carbon atoms selected from the group consisting of aliphatic, aliphatic-cycloaliphatic and araliphatic radicals and aliphatic, aliphaticcycloaliphatic and araliphatic radicals containing hetero-atoms as members of their carbon structure; Rl stands for an alkyl radical; X stands' for a member of the group consisting of oxygen, sulfur,
x1 stands for a member of the group consisting of and 00 ON 8: stands for a member of the group consisting of hydrogen and alkyl radicals; R: stands for a member of the group consisting of low molecular aliphatic hydrocarbon radicals and low molecular aliphatic hydrocarbon radicals substituted by halogen: Hal means halogen: NEZ stands for a member oi the group consisting oi tertiary aliphatic amines, tertiary heterocyclic bases. a. I
Oar-CH I, v.
. CHI-C and alkyl CHE-CH: N o
CHI-C and drying said impregnated textile material. 12. Water-repellent textile material obtained by impregnating a textile material with a quaternary ammonium salt of the general formula:
' axcmmoolnmz-z wherein fi stands for air aliphatic radical oi at least 12 carbon atoms, X stands for a member oi the group consistingoi'oxygen, sulfur Ra Ra Ra stands for a member of the group. consisting of hydrogen and alkyl radicals, Ra stands for a member of the group consisting of low molecular aliphatic hydrocarbon radicals and low molecular aliphatic hydrocarbon radicals substituted by halogen, NEZ stands for a member of the group consisting of tertiary aliphatic amines.
tertiary heterocyclic bases,
alkyl era-cm CH:- H:
Gila-C 2 and I enroll,
N E CHI-CHI 13. Water-repellent textile material obtained by impregnating a textile material with the product of the formula:
14. water-repellent textile material obtained try-impregnating a textile material with the product of the formula:
15. Water-repellent textile material obtained by mpregnating a textile material with the product of the formula:
onnuco.NH.cH,.o.co.cH,.r
GERHARD BALLE.
JOHANN ROSENBACH. ORTHNER,
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2301676X | 1938-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2301676A true US2301676A (en) | 1942-11-10 |
Family
ID=7994155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US27703439 Expired - Lifetime US2301676A (en) | 1938-06-07 | 1939-06-02 | Water-repellent textile material and a process of preparing it |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2301676A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2545070A (en) * | 1947-07-09 | 1951-03-13 | Du Pont | Cellulose ether solutions and method of spinning the same |
| US2574114A (en) * | 1948-04-26 | 1951-11-06 | Bozel Maletra Prod Chimiques | Amide-glyoxal-formaldehyde reaction product and shrinkproofing cellulose textile fibers therewith |
-
1939
- 1939-06-02 US US27703439 patent/US2301676A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2545070A (en) * | 1947-07-09 | 1951-03-13 | Du Pont | Cellulose ether solutions and method of spinning the same |
| US2574114A (en) * | 1948-04-26 | 1951-11-06 | Bozel Maletra Prod Chimiques | Amide-glyoxal-formaldehyde reaction product and shrinkproofing cellulose textile fibers therewith |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2357273A (en) | Textile finishing | |
| US2211976A (en) | Process of imparting hydrophobic properties to cellulose fibers | |
| US2314968A (en) | Process of impregnating textile materials and the material thus obtained | |
| US2168535A (en) | Textile material and a process of preparing it | |
| GB723580A (en) | Improvements relating to the treatment of vinyl resin articles to reduce their tendency to accumulate charges of static electricity | |
| US2254001A (en) | Textile process | |
| US2327162A (en) | New water-repellent agent and process of making same | |
| JPH0665861A (en) | Easy care finishing without formaldehyde of cellulose-containing textile material | |
| US2220508A (en) | Improving the wash-fastness of sizes with aminomethylamide derivatives | |
| US2206928A (en) | Production of condensation products | |
| US2301676A (en) | Water-repellent textile material and a process of preparing it | |
| US2210442A (en) | Capillary active compounds and process of preparing them | |
| US2361185A (en) | Process of making ether compounds | |
| Schuyten et al. | Imparting water-repellency to textiles by chemical methods: a review of the literature | |
| US2338178A (en) | Condensation product | |
| US2343920A (en) | Textile treatment process | |
| US2407703A (en) | Amino amide compounds | |
| US2313742A (en) | Process of treating textile fiber | |
| US2989364A (en) | Process for the improvement of shaped thermoplastic materials containing carbonamide groups | |
| US2304157A (en) | Process for improving textiles | |
| US2445319A (en) | Method for the manufacture of quaternary nitrogen compounds | |
| US2317756A (en) | Process for improving materials containing cellulose | |
| GB636878A (en) | Process of producing an aqueous dispersion for treating fibrous materials and the treatment of such materials therewith | |
| US2270893A (en) | Process of imparting hydrophobic properties to fibrous materials | |
| US2358871A (en) | Textile treatment |