US2088227A - Impregnation of textile fabrics - Google Patents
Impregnation of textile fabrics Download PDFInfo
- Publication number
- US2088227A US2088227A US4078635A US2088227A US 2088227 A US2088227 A US 2088227A US 4078635 A US4078635 A US 4078635A US 2088227 A US2088227 A US 2088227A
- Authority
- US
- United States
- Prior art keywords
- acid
- solution
- urea
- crease
- heating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004744 fabric Substances 0.000 title description 23
- 239000004753 textile Substances 0.000 title description 23
- 238000005470 impregnation Methods 0.000 title description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 44
- 239000002253 acid Substances 0.000 description 42
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 35
- 239000000463 material Substances 0.000 description 30
- 238000010438 heat treatment Methods 0.000 description 25
- 150000003863 ammonium salts Chemical class 0.000 description 20
- 239000004202 carbamide Substances 0.000 description 19
- 235000013877 carbamide Nutrition 0.000 description 19
- 239000000126 substance Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- 239000011347 resin Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 9
- 239000007859 condensation product Substances 0.000 description 8
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000008098 formaldehyde solution Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- 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 3
- NGPGDYLVALNKEG-UHFFFAOYSA-N azanium;azane;2,3,4-trihydroxy-4-oxobutanoate Chemical compound [NH4+].[NH4+].[O-]C(=O)C(O)C(O)C([O-])=O NGPGDYLVALNKEG-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000012260 resinous material Substances 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 2
- 229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 2
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 2
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QYTOONVFPBUIJG-UHFFFAOYSA-N azane;cyanic acid Chemical compound [NH4+].[O-]C#N QYTOONVFPBUIJG-UHFFFAOYSA-N 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000019837 monoammonium phosphate Nutrition 0.000 description 2
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 2
- 229950005308 oxymethurea Drugs 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000012262 resinous product Substances 0.000 description 2
- -1 salt compound Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 239000004135 Bone phosphate Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- ZRIUUUJAJJNDSS-UHFFFAOYSA-N ammonium phosphates Chemical compound [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O ZRIUUUJAJJNDSS-UHFFFAOYSA-N 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- FFZMMILMNFFUCX-KVVVOXFISA-N azanium;[(z)-octadec-9-enyl] sulfate Chemical compound [NH4+].CCCCCCCC\C=C/CCCCCCCCOS([O-])(=O)=O FFZMMILMNFFUCX-KVVVOXFISA-N 0.000 description 1
- WBOXZLRDVULSGV-UHFFFAOYSA-N azanium;ethyl sulfate Chemical compound [H+].N.CCOS([O-])(=O)=O WBOXZLRDVULSGV-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- WCOATMADISNSBV-UHFFFAOYSA-K diacetyloxyalumanyl acetate Chemical compound [Al+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WCOATMADISNSBV-UHFFFAOYSA-K 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical group [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08L61/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08L61/24—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with urea or thiourea
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
- Y10T442/2393—Coating or impregnation provides crease-resistance or wash and wear characteristics
Definitions
- This invention relates to improvements in the treatment of fabrics or other textile materials of the kind known to be susceptible to treatment for the production of crease-resisting products by the aid of resinous condensation-products, hereafter termed resins for brevity.
- the objects of the invention are to provide improved processes of preparing the impregnating agents, and improved processes of eflecting the impregnation, and finalcondensation. Other objects will appear later.
- the scope of the invention is defined in the appended claims.
- the textile material is impregnated with a containing a potentially acid substance.
- ammonium ethyl sulphate ammonium oleyl sulphate or sulphonate
- compounds of similar bases such as monomethylamine, dimethyla-mine, the ethanolamines, the hydrazines, the cyclohexylamines, etc.
- the amino type of compounds appear to liberate acid by reaction between the salt compound and the methylol compounds of the urea-like substances and/or free formaldehyde which may be present or produced.
- the invention also includes broadly a process of producing crease-resisting textile materials in which final heating to insolubilize the resinous material is eilected by direct contact with steam.
- the viscosity should-be about 3 to 5 centlpoises.
- condensates consist mainly of monomethylol and/or dimethylol urea.
- free acid and particularly strong acid causes precipitation of a further condensation product, whereas if the acid is replaced by the corresponding ammonium salt a relatively stabilizing effect is obtained.
- the potentially acid substance appears to liberate acid during the drying process and/or heating process. It is thus possible to add such quantities of the potentially acid substance as will, on heating, liberate larger quantities of acid than could be added as such-to the solution, or alternatively to use a salt of a stronger acid than could be added as such to the solution.
- the final heating necessary to insolubillze the resin can thus be completed in a shorter time or at a lower temperature than when using free acid in the smaller quantities which cannot be exceeded since otherwise the solution would be unstable.
- the condensation of the resinous material should be allowed to proceed to a certain extent before impregnation, otherwise undue loss of formaldehyde will occur during drying, which loss is undesirable technically and economically.
- the, quantity of the potentially acid substance is preferably suflicient to cause insolubilization of the greater part of the resinous material under the chosen conditions of final heating.
- solutions at 60 to 90% concentration mentioned above instead of being allowed to stand in the cold may be raised to say IO--80 C. and then cooled immediately. 7
- the heated fabric is washed in 0.5% warm soap solution for 5 minutes, well rinsed with water and dried in the usual manner.
- the crystalline product from the neutral reaction mixture gives a dimethylol urea of high solubility which is important since wecan prepare powders suitable for use in making solutions for impregnation.
- the material may be washed or finished according to desired known methods, either mechanical or chemical, e. g. the product may be treated with swelling agents or with substances which react with either or both the cellulose and condensation product.
- the mixture is then diluted to 50 to 60% and a suitable catalyst added, he. 1.5% tartaric acid or from 2 to 3% ammonium dihydrogen phosphate 'or ammonium tartrate, calculated on the concentrated mixture.
- a suitable catalyst added, he. 1.5% tartaric acid or from 2 to 3% ammonium dihydrogen phosphate 'or ammonium tartrate, calculated on the concentrated mixture.
- the cloth is impregnated, squeezed and thoroughly dried ata temperature preferably not exceeding 110 0., until, in the case of potentially acid substances, the necessary acidity which we prefer to be pH 4.5 has developed.
- the goods are then heated for 2 minutes at 170 C. in the case .of tartrate and either 1- min. at.
- the heating may be accomplished by passing the material through a chamber containing steam under similar conditionsof time and temperature. After heating, the goods are washed. dried and finished according to known means.
- Cotton goods may also be treated in the above manner but with less advantage than in the case of rayon, both as' filament and as staple fibre. This treatment is applicable broadly e. g. when using substances such as tartaric acid instead of potentially acid substances.
- Example 4 commenced to separate. Further cooling of the liquor produced a total yield of of monomethylol urea of melting point C.
- Process of improving the crease-resistance of textile fabrics which comprises impregnating the fabric with a solution of a reaction product of urea and formaldehyde consisting mainly of a methylol urea and containing a potentially acid ammonium salt and then heating the impregnated fabric to insolubilize the resin.
- Process of improving the crease-resistance of textile materials which consists in impregnating the material with a solution of a partial condensate of urea and formaldehyde containing an ammonium salt in quantity from 1 to 15 per cent of the amount of urea, and heating the impregnated material to insolubilize the resin and produce a crease-resisting product.
- Patent dated July 27, 1937. Disclaimer filed Nov. 25, 1946, by the assignee, Tootal Broadhurst Lee Oompagiy Limited.
- Process of improving the crease-resistance of textile fabrics which comprises impregnating the fabric with a solution of a reaction product of urea and formaldehyde consisting mainly of a methylol urea and containing a potentially acid ammonium salt and then heating the impregnated fabric to insolubilize the resin.
- Process of improving the crease-resistance of textile materials which consists in impregnating the material with a solution of a partial condensate of urea and formaldehyde containing an ammonium salt in quantity from 1 to 15 per cent of the amount of urea, and heating the impregnated material to insolubilize the resin and produce a crease-resisting product.
- Patent dated July 27, 1937. Disclaimer filed Nov. 25, 1946, by the assignee, Tootal Broadhurst Lee Oompagiy Limited.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Treatment Of Fiber Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2687734A GB449243A (en) | 1934-09-19 | 1934-09-19 | Process of improving the crease-resisting properties of textile materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2088227A true US2088227A (en) | 1937-07-27 |
Family
ID=10250617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US4078635 Expired - Lifetime US2088227A (en) | 1934-09-19 | 1935-09-16 | Impregnation of textile fabrics |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2088227A (en)) |
| BE (1) | BE411328A (en)) |
| FR (1) | FR810347A (en)) |
| GB (1) | GB449243A (en)) |
| NL (1) | NL43314C (en)) |
Cited By (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2415564A (en) * | 1942-05-19 | 1947-02-11 | Rohm & Haas | Impregnation of regenerated cellulose fibers |
| US2441859A (en) * | 1945-06-12 | 1948-05-18 | Alrose Chemical Company | Treatment of textile materials with aldehydes |
| US2452005A (en) * | 1945-04-10 | 1948-10-19 | Westinghouse Electric Corp | Method of coating with synthetic resin containing an accelerator, and resin composition |
| US2467160A (en) * | 1948-02-02 | 1949-04-12 | Monsanto Chemicals | Curing catalysts for aminoplasts |
| US2466744A (en) * | 1947-02-14 | 1949-04-12 | Monsanto Chemicals | Curing catalysts for aminoplasts |
| US2468530A (en) * | 1944-08-14 | 1949-04-26 | American Enka Corp | Aftertreatment of viscose rayon |
| US2482755A (en) * | 1945-05-29 | 1949-09-27 | Bancroft & Sons Co J | Flameproofing of fibrous material |
| US2482756A (en) * | 1944-06-10 | 1949-09-27 | Bancroft & Sons Co J | Flameproofing of fibrous materials |
| US2484598A (en) * | 1945-06-05 | 1949-10-11 | Alrose Chemical Company | Reducing the crease and wrinkling tendencies of cellulosic textile fabrics |
| US2484599A (en) * | 1945-06-06 | 1949-10-11 | Alrose Chemical Company | Process of reducing the shrinkage and felting tendencies of protein textile materials |
| US2493381A (en) * | 1947-07-01 | 1950-01-03 | Us Finishing Company | Process for crease-proofing textiles |
| US2495233A (en) * | 1943-05-25 | 1950-01-24 | Comptoir Textiles Artificiels | Method of treating cellulosic materials with trimethylolphenol |
| US2495234A (en) * | 1944-06-05 | 1950-01-24 | Comptoir Textiles Artificiels | Method of treating cellulosic materials with trimethylolphenol |
| US2565152A (en) * | 1946-10-30 | 1951-08-21 | Westinghouse Electric Corp | Process of impregnating a fibrous sheet with a phenolic resin |
| US2631965A (en) * | 1950-05-24 | 1953-03-17 | Ernst O Schnell | Permanent waving of hair |
| US2653121A (en) * | 1949-02-08 | 1953-09-22 | Ernst O Schnell | Permanent waving of hair |
| US2662071A (en) * | 1949-02-16 | 1953-12-08 | Elod Egon | Process of producing dicyandiamideurea-formaldehyde impregnating agents |
| US2687397A (en) * | 1951-09-21 | 1954-08-24 | Shell Dev | Resin-forming compositions containing amine salts of sulfonic acids |
| US2729577A (en) * | 1953-02-27 | 1956-01-03 | Du Pont | Method of imparting antistatic properties to textile materials |
| US2737504A (en) * | 1953-11-05 | 1956-03-06 | Jacques Wolf & Co | Reaction product of dicyandiamide, formaldehyde and alkali metal salt of a sulfonic acid |
| US2739908A (en) * | 1950-10-24 | 1956-03-27 | Tootal Broadhurst Lee Co Ltd | Method of impregnating textile fabric with resin |
| US2774687A (en) * | 1952-09-03 | 1956-12-18 | Nottebohm Carl Ludwig | Process for the manufacture of porous flexible sheet material |
| US2842120A (en) * | 1953-04-15 | 1958-07-08 | Johnson & Johnson | Material for an orthopedic cast and process of making the same |
| US2859136A (en) * | 1950-07-08 | 1958-11-04 | Tootal Broadhurst Lee Co Ltd | Process for the treatment of fabrics with resinous condensation products |
| DE1048864B (de) * | 1951-06-27 | 1959-01-22 | Tootal Broadhurst Lee Co Ltd | Verfahren zum Impraegnieren von ganz oder teilweise aus regenerierter Cellulose bestehenden Textilien |
| US2871209A (en) * | 1956-10-24 | 1959-01-27 | Rohm & Haas | Aminoplast resin coating compositions |
| US2930716A (en) * | 1956-10-12 | 1960-03-29 | Dow Chemical Co | Crease resistant resin composition for textiles |
| US3027365A (en) * | 1958-10-13 | 1962-03-27 | Marblette Corp | Production of reaction products of methylol urea with ammonium containing compounds |
| US3177093A (en) * | 1962-06-06 | 1965-04-06 | American Cyanamid Co | Method of treating cellulose textile material and the treated material |
| US3853604A (en) * | 1966-07-09 | 1974-12-10 | Vepa Ag | Method for the continuous high-grade finishing of textile materials |
| US4391770A (en) * | 1980-12-01 | 1983-07-05 | Imperial Chemical Industries Plc | Process for spinning amino-formaldehyde fibers |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL92811C (en)) * | 1951-06-27 | |||
| BE534102A (en)) * | 1954-02-03 | |||
| DE1002282B (de) * | 1955-05-23 | 1957-02-14 | Rotta Chem Fab Theodor | Verfahren zum Ausruesten von Textilien mit waermehaertbaren Kunstharzen |
-
0
- NL NL43314D patent/NL43314C/xx active
- BE BE411328D patent/BE411328A/xx unknown
-
1934
- 1934-09-19 GB GB2687734A patent/GB449243A/en not_active Expired
-
1935
- 1935-09-13 FR FR810347D patent/FR810347A/fr not_active Expired
- 1935-09-16 US US4078635 patent/US2088227A/en not_active Expired - Lifetime
Cited By (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2415564A (en) * | 1942-05-19 | 1947-02-11 | Rohm & Haas | Impregnation of regenerated cellulose fibers |
| US2495233A (en) * | 1943-05-25 | 1950-01-24 | Comptoir Textiles Artificiels | Method of treating cellulosic materials with trimethylolphenol |
| US2495234A (en) * | 1944-06-05 | 1950-01-24 | Comptoir Textiles Artificiels | Method of treating cellulosic materials with trimethylolphenol |
| US2482756A (en) * | 1944-06-10 | 1949-09-27 | Bancroft & Sons Co J | Flameproofing of fibrous materials |
| US2468530A (en) * | 1944-08-14 | 1949-04-26 | American Enka Corp | Aftertreatment of viscose rayon |
| US2452005A (en) * | 1945-04-10 | 1948-10-19 | Westinghouse Electric Corp | Method of coating with synthetic resin containing an accelerator, and resin composition |
| US2482755A (en) * | 1945-05-29 | 1949-09-27 | Bancroft & Sons Co J | Flameproofing of fibrous material |
| US2484598A (en) * | 1945-06-05 | 1949-10-11 | Alrose Chemical Company | Reducing the crease and wrinkling tendencies of cellulosic textile fabrics |
| US2484599A (en) * | 1945-06-06 | 1949-10-11 | Alrose Chemical Company | Process of reducing the shrinkage and felting tendencies of protein textile materials |
| US2441859A (en) * | 1945-06-12 | 1948-05-18 | Alrose Chemical Company | Treatment of textile materials with aldehydes |
| US2565152A (en) * | 1946-10-30 | 1951-08-21 | Westinghouse Electric Corp | Process of impregnating a fibrous sheet with a phenolic resin |
| US2466744A (en) * | 1947-02-14 | 1949-04-12 | Monsanto Chemicals | Curing catalysts for aminoplasts |
| US2493381A (en) * | 1947-07-01 | 1950-01-03 | Us Finishing Company | Process for crease-proofing textiles |
| US2467160A (en) * | 1948-02-02 | 1949-04-12 | Monsanto Chemicals | Curing catalysts for aminoplasts |
| US2653121A (en) * | 1949-02-08 | 1953-09-22 | Ernst O Schnell | Permanent waving of hair |
| US2662071A (en) * | 1949-02-16 | 1953-12-08 | Elod Egon | Process of producing dicyandiamideurea-formaldehyde impregnating agents |
| US2631965A (en) * | 1950-05-24 | 1953-03-17 | Ernst O Schnell | Permanent waving of hair |
| US2859136A (en) * | 1950-07-08 | 1958-11-04 | Tootal Broadhurst Lee Co Ltd | Process for the treatment of fabrics with resinous condensation products |
| US2739908A (en) * | 1950-10-24 | 1956-03-27 | Tootal Broadhurst Lee Co Ltd | Method of impregnating textile fabric with resin |
| DE1048864B (de) * | 1951-06-27 | 1959-01-22 | Tootal Broadhurst Lee Co Ltd | Verfahren zum Impraegnieren von ganz oder teilweise aus regenerierter Cellulose bestehenden Textilien |
| US2687397A (en) * | 1951-09-21 | 1954-08-24 | Shell Dev | Resin-forming compositions containing amine salts of sulfonic acids |
| US2774687A (en) * | 1952-09-03 | 1956-12-18 | Nottebohm Carl Ludwig | Process for the manufacture of porous flexible sheet material |
| US2729577A (en) * | 1953-02-27 | 1956-01-03 | Du Pont | Method of imparting antistatic properties to textile materials |
| US2842120A (en) * | 1953-04-15 | 1958-07-08 | Johnson & Johnson | Material for an orthopedic cast and process of making the same |
| US2737504A (en) * | 1953-11-05 | 1956-03-06 | Jacques Wolf & Co | Reaction product of dicyandiamide, formaldehyde and alkali metal salt of a sulfonic acid |
| US2930716A (en) * | 1956-10-12 | 1960-03-29 | Dow Chemical Co | Crease resistant resin composition for textiles |
| US2871209A (en) * | 1956-10-24 | 1959-01-27 | Rohm & Haas | Aminoplast resin coating compositions |
| US3027365A (en) * | 1958-10-13 | 1962-03-27 | Marblette Corp | Production of reaction products of methylol urea with ammonium containing compounds |
| US3177093A (en) * | 1962-06-06 | 1965-04-06 | American Cyanamid Co | Method of treating cellulose textile material and the treated material |
| US3853604A (en) * | 1966-07-09 | 1974-12-10 | Vepa Ag | Method for the continuous high-grade finishing of textile materials |
| US4391770A (en) * | 1980-12-01 | 1983-07-05 | Imperial Chemical Industries Plc | Process for spinning amino-formaldehyde fibers |
Also Published As
| Publication number | Publication date |
|---|---|
| GB449243A (en) | 1936-06-19 |
| NL43314C (en)) | 1900-01-01 |
| FR810347A (fr) | 1937-03-19 |
| BE411328A (en)) | 1900-01-01 |
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