US3165424A - Treatment of cellulose textiles - Google Patents
Treatment of cellulose textiles Download PDFInfo
- Publication number
- US3165424A US3165424A US20268A US2026860A US3165424A US 3165424 A US3165424 A US 3165424A US 20268 A US20268 A US 20268A US 2026860 A US2026860 A US 2026860A US 3165424 A US3165424 A US 3165424A
- Authority
- US
- United States
- Prior art keywords
- cellulose
- water soluble
- textile material
- substance
- treated
- 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
- 229920002678 cellulose Polymers 0.000 title claims description 103
- 239000001913 cellulose Substances 0.000 title claims description 101
- 239000004753 textile Substances 0.000 title claims description 65
- 239000000463 material Substances 0.000 claims description 77
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 55
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 37
- 239000000126 substance Substances 0.000 claims description 37
- 238000010438 heat treatment Methods 0.000 claims description 24
- 239000003513 alkali Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 23
- -1 HYDROXYL GROUPS Chemical group 0.000 claims description 20
- 229920013820 alkyl cellulose Polymers 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000012261 resinous substance Substances 0.000 claims description 19
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 14
- 239000008103 glucose Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 239000002168 alkylating agent Substances 0.000 claims description 12
- 229940100198 alkylating agent Drugs 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 238000004132 cross linking Methods 0.000 claims description 10
- 235000010980 cellulose Nutrition 0.000 description 94
- 239000000243 solution Substances 0.000 description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 18
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 16
- 229920003086 cellulose ether Polymers 0.000 description 11
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 125000001033 ether group Chemical group 0.000 description 9
- 229940015043 glyoxal Drugs 0.000 description 9
- 238000005406 washing Methods 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 7
- 229960003750 ethyl chloride Drugs 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 6
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 5
- 229940102396 methyl bromide Drugs 0.000 description 5
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 5
- 229950005308 oxymethurea Drugs 0.000 description 5
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 5
- 229920000297 Rayon Polymers 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000004900 laundering Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002964 rayon Substances 0.000 description 4
- 230000037303 wrinkles Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229940093470 ethylene Drugs 0.000 description 3
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 230000036316 preload Effects 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910021538 borax Inorganic materials 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
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical class OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VGYFVNQYBUPXCQ-UHFFFAOYSA-N ethene;2-methyloxirane Chemical group C=C.CC1CO1 VGYFVNQYBUPXCQ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/12—Aldehydes; Ketones
- D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
- C08B11/14—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals with nitrogen-containing groups
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/12—Aldehydes; Ketones
-
- 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
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/03—Polysaccharides or derivatives thereof
- D06M15/05—Cellulose or derivatives thereof
- D06M15/09—Cellulose ethers
-
- 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
Definitions
- the present invention relates to the treatment of textile materials so as to render the same crease resistant and wrinkle resistant, and more particularly to the treatment of cellulose materials to impart crease resistant and wrinkle resistant properties to the same while maintaining the strength of the material.
- the textile material is coated with cellulose ethers of different kinds.
- alkyl cellulose products such as methyl cellulose or methyl ethyl cellulose, which preferably should be completely etherified because otherwise they are not sufiiciently water-soluble, are not suitable because they can not prevent the stiffness and brittleness of a textile mate rial caused by the deposition of synthetic resins.
- the present invention provides a method of providing crease resistance to cellulose material by a procedure which avoids all of the above and other enumerated disadvantages of the prior art.
- the present invention mainly concerns a method of improving the upon heating to a predetermined temperature below the temperature at which damage to the cellulose textile material occurs is transformed into an insoluble resinous substance, the water soluble resin-forming substance con taining hydroxyl. groups, and also containing in solution a water soluble alkyloxy cellulose containing free bydroxyl'groups, and heating the thus treated cellulose textile material to the predetermined temperature so as to convert the water soluble resin-forming substance into an insoluble resinous substance and to cause cross linking reaction between the' same and the water soluble alkyloxy cellulose, thereby forming a treated cellulose textile material having improved properties.
- the treating of the textile material may be carried out by spraying the same with the aqueous liquor, but is preferably accomplished by immersing thetextile material in the liquor.
- the heating temperature is generally above 100 C. and is most-preferably at a temperature between 100 and 150 C.
- the method of the present invention makes it possible to improve textile material of the cellulose type with respect to the crease resistance thereof while retaining the properties of strength and also while giving to the textile material a good feel.
- the method of the present invention is particularly advantageous in that the crease resistance which is imparted to the textiles remains even after laundering.
- This is achieved in accordance with the present inventionby the use of the cellulose mixed ether, that is the alkoxy cellulose which contains free hydroxyl groups in the cellulose molecule, these free hydroxyl Such" groups reacting with and cross linking the resin-forming substance, for example the dimethylol urea.
- the cellulose mixed ether also has the advantage'of a good water solubility and the possibility of producing stable, non-flocculating solutions.
- the alkyloxy alkyl celluloses which are utilized'in the present invention are produced by reacting an alkali cellulose with about 1 mol of a common alkylating agent and'about 3 mols of a common alkoxyl-ating agent, calculated per each mol of glucose anhydride of the cellulose.
- I alkoxylating agent it is possible to use a lower alkylene Particularly good properties of the treated textile with re spect to crease or wrinkle resistance and good feel are achieved by maintaining the mol ratios of the produced cellulose ether as set forth above.
- Celluloses of this type are suitable as starting material for the production of the mixed cellulose ethers of the present invention.
- alkylating agent it is possible to use a "lowe'r alkyl halogenide such as methyl bromide,
- oxide such as ethylene oxide, propylene oxide, ethylene I magnesium chloride, aluminum chloride, ammonium chlo-f ride,-ammonium nitrate, borax, etc. 1
- suitable resin-forming substances for the purpose of the present invention are formaldehyde or such as methylol urea, dimethylol urea, melamine-formal-v dehyde condensates, methylol biuret, dimethylol biuret, the reaction product in neutral to slightly alkaline medium of methylol urea and glyoxal and similar products;
- the textile material which has been treated with the liquor in accordance with the present invention, which actually have been impregnated with the liquor, for example'by spraying the liquor onto the textile material or preferably by immersing the material in the liquor, is
- this predried textile material can be heated to a temperature up to 150 C. depending upon the duration of heating. 7
- the Y drying and heating can also be carried out in a single step.
- samples of the same cotton fabric were treated under the same conditions withliquors which instead of containing the etherified cellulose ethyloxyethyl cellulose in a mol ratio of 1:113, contained ethyloxy cellulose which was produced in a ratio of 0121- 1 luloseicalculated as glucose anhydride) to ethyl chloride to ethylene oxide in a mol ratio of 1:1:2 andin another test in a mol ratio of 1:1;4'.
- Y The creaseangles'in Weft and warp threads and the feel characteristics of the treated samples and of the untreated samples were determined and are set forth in the following table:- e
- the yellowish-brown reaction"productq' is filtered 01f by suction, pressed sharply-and dried under vacuum over calcium chloride.
- the product is easilysoluble in cold water and no fiber residue remains upon dissolution.
- Y yieldof thevdry reaction product is 60 to .g.
- the diluting agent must be peroxide-free, ;To removethe peroxideithe. tetrahydrofurane is allowed to stand with concentrated potassium hydroxide with shaking frorn tirne to time, and after separation of the .potassium hydroxide liquor is'rectified.
- a v a I I I EXAMPLE .II' V A treating 'liquidis used containing aper"liter l00 grams of technicalglyoxal .(consisting of 20% glyoxalic ,acid, 50% acetic acid and 30% glyorgal),"25 grams of technical borax and 2 grams. of an ethyloxyethyl cellu- .lose (molar relationship 111:3) prepared asndescribed in: Example I The solution 11am pH or 3.7. V
- EXAMPLE III A rayon shirt material as described in Example II is soaked in a treating liquid containing 90 grams of the reaction product obtained by reaction of dirnethylol urea and glyoxal in aqueous solution at a pH of 7.5, 11.5 grams of AlCl .6H O, 10 grams of boric acid and 2 grams of the mixed cellulose ether described in Example II.
- the pH-of the treating liquid is 3.6. Liquidis squeezed off to a residual moisture content of 100% and the material is then dried at between 100 and 110 C.
- the thus treated material has a crease angle of 123/ 115, or of 108/ 120 after one washing'with sodium lauryl sulfonate, a rub resistance of 890 and pleasant'soft feel (touch).
- the material finished with the same treating liquid except for the absence of'cellulose ether and under otherwise similar conditions has a crease angle of 128/131, or 11 l/111. after one washing with sodiuin laurylsulfonate and a rub resistance of 659.
- a treating liquid is prepared which contains per liter 100 grams of dimethylol urea 100%, grams of NH NO and 2 grams of the ethyloxyethyl cellulose (molar relationship 1:1:3) similar to the ether used in Example Ill.
- a sample of the rayon shirtmaterial'of Example 111 is soaked in this treating liquid and after removal of excess liquid by squeezing, the sampleis subjected to'a single drying step carried out forfive minutes at 130 C.
- the crease angles in warp and Weft of the treated material are 142/140, or 122/130 after one washing with sodium lauryl sulfonate.
- a sample of similar material finished with a treating liquid free of the addition of cellulose ether has crease angles-of '129/129, or 115/127.a'fter one washing with sodium lauryl sulfonate.
- Method of improving properties such as the crease resistance and non-shrinking properties of cellulose textiles, comprising the steps of treating a cellulosetextile material with an acid aqueous liquor containing in solution a water soluble resin-forming substance which upon heating to a temperature between and C. is transformed into an insoluble resinousvsubstance, said water soluble resin-forming substance containing. hydroxyl groups, and also containing in solution a water soluble alkyloxy alkyl cellulose mixed ether.
- Method of improving properties such as the crease resistance and non-shrinking properties of cellulose textiles comprising the steps of treating acellulose textile material'with an acid aqueous liquor containing in. solution a water soluble resin-forming substance which upon heating to a predeterminedtemperature below the temterial occurs is transformed into an insoluble resinous substance, said Water soluble resin-forming substance containing hydroxyl groups, and also containing in solution a water soluble alkyloxy alkyl cellulose mixed containing ether groups and also containing free hydroxyl groups formed by the reaction of an alkali cellulose with about 1 mol ofa lower alkyl halogenide as, an alkylating agent and about 3 mols of a lower alkylene oxide as an alkoxylatingagent calculated per eachmol of glucose anhydride of saidalkali cellulose; and heating the thus treated cellulose textile material to said predetermined temperature so as. to convert said water soluble resin-forming substance into an insoluble resinous substance and to cause cross linking reaction
- Method of improving properties such'as the crease resistance and non-shrinking properties of cellulose textiles comprising the steps ;of treating a cellulose textile 'material'withan acid aqueous liquor containing in solution a water soluble resin-forming substance whichupon j heating-to a predetermined temperature below the temperature at which damage to said cellulose textile ma-zx terial occurs is transformed into an insoluble resinous,"- substance said water soluble resin-forming substance containing hydroxyl groups, and also containing in solution a Water soluble alkyloxy alkyl cellulose mixed ,ether 7 containing ether groups and also containing free hydroxyl groups formed by the reaction of an alkali cellulose with about 1 mol of an alkylating agent selected from the group consisting of methyl bromide, methyl chloride, ethyl bromide and ethyl chloride'and'about?
- an alkylating agent selected from the group consisting of methyl bromide, methyl chloride, ethyl bro
- an alkoxylating agent selected from the group consisting of ethylene oxide, propylene oxide and ethylene chlorohydrinycalculated ,per each mol of glucose an! hydride of said alkali cellulose; and heatingvithe thus 7 7:.-'Method of. improving properties such asi thecrease resistance and non-shrinkingproperties of cellulose textiles, comprising vthe stepsfof treatinga cellulose textile material with 'anyacid aqueousflliquorfliaving a pHbe ':tween 3 and 5 and containing in solution a water soluble resin-forming substance which upon'heatingato atemperature between '100 and 150" C.
- said water soluble resin- 4 forming substance containing hydroxyl groups, and also containing'in solutiona Water soluble alkyloxy alkyl cellulose mixed ether containing ether'groups and also containing free hydroxyl groups formed by the reaction of an alkali cellulose with about-l mol of an alkylati'ng agent and about-3 mols of an, alkoxylating agent'calculatedper' eachrnol of glucose anhydride of saidj'alkalicellulose;
- Method of improving properties such as the crease resistance and non-shrinkingproperties of cellulose textiles, comprising the steps of treatingacellulose textile material with an acid aqueous liquor containing in solu tion a Water soluble resin-forming substance which upon same' and saidwater soluble alkyloxy alkyl cellulose, thereby forming a treated'cellulose textile'rnaterial having improved properties.
- Methodho d of improving properties such as the crease resistance and 'nonshrinking properties of cellulose textiles comprising the steps of treating a cellulose textile material with an acid aqueous liquor containing in solu-- tion a 'waterisoluble resin-forming ,substancelwhiich upon heating to atemperature between 1.00 and 150 is transformed into an insoluble resinous substance; said '.water soluble resin-forming substance containing/hydroxyl groups, and "also containing in solution 1-;5 g.
- tiles comprising the stepsof treatingla cellulose textile "material with'an acid aqueous liquor' haying av pH'be tween 3 and, 5 and containing in solution a wate'r solublei resin-forming" substance which' upon heating'to atem perature between and 15Q-C,. is trahsforrned into an insoluble resinous substance,"said*watersoluble'resinforming substance.
- an alkali I cellulosel with about "1 fmol "of an alkylating agent”selected from the group;consist ing of methyl bromide, methyl chloride, 'eth yl bromide andiethyl chloride and about 3 mols of ani,,alkoxylating. agent selected from thegroup consisting of ethylene oxide; propylene oxide-and ethylene. chlorohydrin calculated pereach' molof glucose 'anhydridef of said'.
- Method of improving properties such as the crease resistance and non-shrinking properties of cellulose textiles, comprising the steps of treating a cellulose textile material with an acid aqueous liquor containing in solution a water soluble resin-forming substance selected from the group consisting of formaldehyde, glyoxal, dimethylol urea, methylol urea, melamine-formaldehyde condensate, methylol biuret, dimethylol biuret and the reaction product of methylol urea and glyoxal which upon heating to a predetermined temperature below the temperature at which damage to said cellulose textile material occurs is transformed into an insoluble resinous substance, said water-soluble resin-forming substance containing hydroxyl groups, and also containing in solution a water soluble alkyloxy alkyl cellulose mixed containing ether groups and also containing free hydroxyl groups formed by the reaction of an alkali cellulose
- Method of improving properties such as the crease resistance and non-shrinking properties of cellulose textiles, comprising the steps of treating a cellulose textile material with an acid aqueous liquor having a pH between 3 and 5 and containing in solution a Water soluble resin-forming substance selected from the group consisting of formaldehyde, glyoxal, dimethylol urea, methylol urea, melamine-formaldehyde condensate, methylol biuret, dimethylol biuret and the reaction product of methyiol urea and glyoxal which upon heating to a termperature between and C.
- a Water soluble resin-forming substance selected from the group consisting of formaldehyde, glyoxal, dimethylol urea, methylol urea, melamine-formaldehyde condensate, methylol biuret, dimethylol biuret and the reaction product of methyiol
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP22536A DE1093319B (de) | 1959-04-06 | 1959-04-06 | Verfahren zum Knitterfest- und Krumpffreimachen von Textilien aus nativer oder regenerierter Cellulose |
Publications (1)
Publication Number | Publication Date |
---|---|
US3165424A true US3165424A (en) | 1965-01-12 |
Family
ID=7368789
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US20268A Expired - Lifetime US3165424A (en) | 1959-04-06 | 1960-04-06 | Treatment of cellulose textiles |
Country Status (6)
Country | Link |
---|---|
US (1) | US3165424A (en)) |
CH (1) | CH369102A (en)) |
DE (1) | DE1093319B (en)) |
FR (1) | FR1250302A (en)) |
GB (1) | GB921058A (en)) |
NL (1) | NL249295A (en)) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1652868A1 (en) * | 2004-10-29 | 2006-05-03 | Clariant (France) | Aminoplast resin composition |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4233497A1 (de) * | 1992-10-06 | 1994-04-07 | Basf Ag | Verwendung von wäßrigen Polymerisatdispersionen als Textilhilfsmittel zur pflegeleichten Veredlung von Textilien |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1505043A (en) * | 1922-06-10 | 1924-08-12 | Lilienfeld Leon | Cellulose ether and process of making same |
US2190451A (en) * | 1935-11-09 | 1940-02-13 | Du Pont | Cellulose derivatives |
US2469431A (en) * | 1945-09-27 | 1949-05-10 | Carbide & Carbon Chem Corp | Insolubilization of water-soluble hydroxyl-containing polymeric materials |
US2644818A (en) * | 1949-02-25 | 1953-07-07 | British Celanese | Manufacture of cellulose ethers |
US2672427A (en) * | 1951-05-26 | 1954-03-16 | American Viscose Corp | Process for rendering films and the like water-repellent, greaseproof, and moistureproof |
US2949452A (en) * | 1956-04-30 | 1960-08-16 | Dow Chemical Co | Process for preparing alkyl hydroxyalkyl cellulose ethers and the product obtained thereby |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB516624A (en) * | 1938-06-29 | 1940-01-08 | Roger Wallach | Improvements in or relating to the treatment of textile materials |
US2469348A (en) * | 1945-04-07 | 1949-05-03 | Dow Chemical Co | Cellulose derivative compositions |
BE495775A (en)) * | 1949-05-20 | |||
GB683069A (en) * | 1949-09-13 | 1952-11-19 | Courtaulds Ltd | Improvements in and relating to the production of water-soluble mixed cellulose ethers |
US2802752A (en) * | 1953-12-30 | 1957-08-13 | Apponaug Company | Process of treating textile fabric |
-
0
- NL NL249295D patent/NL249295A/xx unknown
-
1959
- 1959-04-06 DE DEP22536A patent/DE1093319B/de active Pending
-
1960
- 1960-02-29 CH CH225960A patent/CH369102A/de unknown
- 1960-03-07 FR FR820621A patent/FR1250302A/fr not_active Expired
- 1960-04-05 GB GB12079/60A patent/GB921058A/en not_active Expired
- 1960-04-06 US US20268A patent/US3165424A/en not_active Expired - Lifetime
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1505043A (en) * | 1922-06-10 | 1924-08-12 | Lilienfeld Leon | Cellulose ether and process of making same |
US2190451A (en) * | 1935-11-09 | 1940-02-13 | Du Pont | Cellulose derivatives |
US2469431A (en) * | 1945-09-27 | 1949-05-10 | Carbide & Carbon Chem Corp | Insolubilization of water-soluble hydroxyl-containing polymeric materials |
US2644818A (en) * | 1949-02-25 | 1953-07-07 | British Celanese | Manufacture of cellulose ethers |
US2672427A (en) * | 1951-05-26 | 1954-03-16 | American Viscose Corp | Process for rendering films and the like water-repellent, greaseproof, and moistureproof |
US2949452A (en) * | 1956-04-30 | 1960-08-16 | Dow Chemical Co | Process for preparing alkyl hydroxyalkyl cellulose ethers and the product obtained thereby |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1652868A1 (en) * | 2004-10-29 | 2006-05-03 | Clariant (France) | Aminoplast resin composition |
US20060093843A1 (en) * | 2004-10-29 | 2006-05-04 | Clariant International Ltd. | Aminoplast resin compositions |
US7169881B2 (en) | 2004-10-29 | 2007-01-30 | Clariant (France) | Aminoplast resin compositions |
US20070100117A1 (en) * | 2004-10-29 | 2007-05-03 | Clariant (France) | Aminoplast resin composition |
US7399529B2 (en) | 2004-10-29 | 2008-07-15 | Clariant (France) | Aminoplast resin composition |
Also Published As
Publication number | Publication date |
---|---|
CH225960A4 (en)) | 1962-12-29 |
DE1093319B (de) | 1960-11-24 |
CH369102A (de) | 1963-06-29 |
FR1250302A (fr) | 1961-01-06 |
NL249295A (en)) | |
GB921058A (en) | 1963-03-13 |
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