GB776468A - Acetal condensation products and process for dimensional control of textile and paper materials - Google Patents
Acetal condensation products and process for dimensional control of textile and paper materialsInfo
- Publication number
- GB776468A GB776468A GB36455/54A GB3645554A GB776468A GB 776468 A GB776468 A GB 776468A GB 36455/54 A GB36455/54 A GB 36455/54A GB 3645554 A GB3645554 A GB 3645554A GB 776468 A GB776468 A GB 776468A
- Authority
- GB
- United Kingdom
- Prior art keywords
- glycol
- acid
- paraformaldehyde
- toluene
- diethylene
- 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
Links
- 239000007859 condensation product Substances 0.000 title abstract 4
- 239000000463 material Substances 0.000 title abstract 3
- 239000004753 textile Substances 0.000 title abstract 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 title 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 8
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N alpha-ketodiacetal Natural products O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 abstract 4
- 239000003054 catalyst Substances 0.000 abstract 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 4
- 229920002866 paraformaldehyde Polymers 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000001299 aldehydes Chemical class 0.000 abstract 3
- -1 alkyl radicals Chemical class 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 239000000047 product Substances 0.000 abstract 3
- 239000001117 sulphuric acid Substances 0.000 abstract 3
- 235000011149 sulphuric acid Nutrition 0.000 abstract 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 abstract 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- 229920000297 Rayon Polymers 0.000 abstract 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 2
- 230000002378 acidificating effect Effects 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 229920002301 cellulose acetate Polymers 0.000 abstract 2
- 239000004744 fabric Substances 0.000 abstract 2
- 239000012530 fluid Substances 0.000 abstract 2
- 229940015043 glyoxal Drugs 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 229920001515 polyalkylene glycol Polymers 0.000 abstract 2
- 238000010992 reflux Methods 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 239000000600 sorbitol Substances 0.000 abstract 2
- 239000011701 zinc Substances 0.000 abstract 2
- 229910052725 zinc Inorganic materials 0.000 abstract 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 abstract 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical class CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 abstract 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004677 Nylon Substances 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- DUFKCOQISQKSAV-UHFFFAOYSA-N Polypropylene glycol (m w 1,200-3,000) Chemical class CC(O)COC(C)CO DUFKCOQISQKSAV-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 abstract 1
- 238000013019 agitation Methods 0.000 abstract 1
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 235000011126 aluminium potassium sulphate Nutrition 0.000 abstract 1
- 239000001164 aluminium sulphate Substances 0.000 abstract 1
- 235000011128 aluminium sulphate Nutrition 0.000 abstract 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical class Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 1
- 235000019270 ammonium chloride Nutrition 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 239000003599 detergent Substances 0.000 abstract 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 abstract 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 230000002070 germicidal effect Effects 0.000 abstract 1
- 235000011187 glycerol Nutrition 0.000 abstract 1
- 230000005484 gravity Effects 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229920001778 nylon Polymers 0.000 abstract 1
- 235000006408 oxalic acid Nutrition 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 150000003016 phosphoric acids Chemical class 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
- 239000002964 rayon Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 102220289727 rs1253463092 Human genes 0.000 abstract 1
- 235000015424 sodium Nutrition 0.000 abstract 1
- 235000011127 sodium aluminium sulphate Nutrition 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 abstract 1
- 238000009988 textile finishing Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 229920003169 water-soluble polymer Polymers 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/53—Polyethers; Polyesters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
- C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G4/00—Condensation polymers of aldehydes or ketones with polyalcohols; Addition polymers of heterocyclic oxygen compounds containing in the ring at least once the grouping —O—C—O—
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C11/00—Surface finishing of leather
- C14C11/003—Surface finishing of leather using macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
-
- 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
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/51—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof
- D06M11/55—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof with sulfur trioxide; with sulfuric acid or thiosulfuric acid or their salts
-
- 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
- D06M13/137—Acetals, e.g. formals, or ketals
-
- 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
- D06M15/53—Polyethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
Water-soluble polymers are made by condensing at least one polyalkylene glycol containing from 2 to 4 alkylene groups with at least one aldehyde in the presence of an acidic catalyst and preferably in the presence of an azeotroping liquid, e.g. toluene, benzene, xylene and ethylbenzene. Reactants specified are: glycols-diethylene, dipropylene, dibutylene, triethylene, tetraethylene and tripropylene glycols; aldehydes-formalin, paraformaldehyde, trioxane, methylal, acetaldehyde, butanal, benzaldehyde, glyoxal and terephthalaldehyde. Polyols such as glycerine, pentaerythritol and sorbitol may be added to the glycol(s) in amounts up to 50 mol. per cent of the glycol(s) used. The polymers may be terminated, wholly or in part, by alkyl radicals containing not more than 8 carbon atoms, e.g. by co-reacting the aldehyde and glycol with a minor amount of a half ether of a glycol. Catalysts specified are sulphuric acid, alkane sulphonic acid, phosphoric acids, acid halides, e.g. zinc, stannic, and aluminium chlorides, and acid clays. In examples, viscous liquids are obtained by reacting in the presence of toluene and sulphuric acid (2) diethylene and dipropylene glycols, (3) diethylene glycol and sorbitol and (5) diethylene glycol and b -methoxyethanol with paraformaldehyde, and (4) diethylene glycol with paraformaldehyde and glyoxal. The products may be used in textile finishing (see Group IV (c)), leather and paper treating, and as hydraulic fluids, lubricants, embalming fluids, germicides and fungicides.ALSO:A water-soluble condensation product of the formula <FORM:0776468/IV(b)/1> where X and Y may be either H or -CH2OH, is obtained by heating diethylene glycol, paraformaldehyde, sulphuric acid and toluene under reflux with a moisture trap inserted between the flask and reflux condenser. After a certain amount of water of reaction had been withdrawn from the reaction mixture, toluene was removed by heating in vacuo with agitation, and the resulting product was neutralized with dilute NaOH. The product had a molecular weight of 480 (Rast.), a hydroxy equivalent of 220, a specific gravity of 1.155 at 34.5 DEG C., and a refractive index N30D=1.462.ALSO:Textile materials, for example filaments, staple fabrics and garments, of cotton viscose rayon, cuprammonium rayon or hydrolysed cellulose acetate, or mixtures thereof with cellulose acetate, nylon or wool, are rendered dimensionally stable by treatment with an aqueous bath containing a water-soluble polymeric condensation product of at least one polyalkylene glycol and at least one aldehyde (see Group IV(a)), and an acidic catalyst in an amount of 5 to 200 per cent by weight of the condensation product and heating the treated materials at a curing temperature of at least 121 DEG C. Catalysts specified are aluminium, zinc and stannic chlorides, aluminium sulphate, oxalic acid, sodium acid sulphate, sodium and potassium alums, dimethyl oxalate and ammonium chloride. The cured fabric may then be washed lightly with a detergent and a mild akali, rinsed and dried. Examples are given.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US403057A US2785949A (en) | 1954-01-08 | 1954-01-08 | Process for the dimensional control of cellulose textile materials by applying polymeric acetals and products resulting therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB776468A true GB776468A (en) | 1957-06-05 |
Family
ID=23594318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB36455/54A Expired GB776468A (en) | 1954-01-08 | 1954-12-16 | Acetal condensation products and process for dimensional control of textile and paper materials |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2785949A (en) |
| BE (1) | BE534687A (en) |
| ES (1) | ES222108A1 (en) |
| FR (1) | FR1131435A (en) |
| GB (1) | GB776468A (en) |
| NL (1) | NL193521A (en) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2903328A (en) * | 1956-12-19 | 1959-09-08 | Quaker Chemical Products Corp | Process for the dimensional control of cellulosic materials |
| US2945738A (en) * | 1958-01-29 | 1960-07-19 | Chicopee Mfg Corp | Low cover factor woven cellulose textile material resistant to corrugation in washing and tumble drying |
| US2988417A (en) * | 1958-12-29 | 1961-06-13 | Rohm & Haas | Process for crease-proofing cellulosic fabrics |
| NL247423A (en) * | 1959-01-17 | |||
| US3015584A (en) * | 1959-03-23 | 1962-01-02 | Robert M Reinhardt | Wrinkle resistance treatment for cellulosic textile fabrics |
| BE593301A (en) * | 1959-07-24 | |||
| NL279087A (en) * | 1961-06-28 | |||
| US3227511A (en) * | 1961-08-02 | 1966-01-04 | Kendall & Co | Methods of forming woven stretchable fabrics |
| US3145132A (en) * | 1961-08-02 | 1964-08-18 | Kendall & Co | Woven stretchable fabrics |
| BE630342A (en) * | 1962-03-30 | |||
| US3660009A (en) * | 1969-02-02 | 1972-05-02 | Millmaster Onyx Corp | Method of manufacturing ready-to-wear crease-resistive garments |
| US4093666A (en) * | 1974-02-06 | 1978-06-06 | Hoechst Aktiengesellschaft | Process for the manufacture of glycol ether formals |
| US4189609A (en) * | 1974-08-19 | 1980-02-19 | Basf Wyandotte Corporation | Multi-block coupled polyoxyalkylene copolymer surfactants |
| US4200564A (en) * | 1976-05-20 | 1980-04-29 | Sandoz Ltd. | Aqueous preparations for treating textile substrates comprising regenerated cellulose |
| CH629926B (en) * | 1976-05-20 | Sandoz Ag | DRY CROSS-LINKING PROCESS FOR THE PERMANENT FINISHING OF TEXTILES MADE FROM REGENERATED CELLULOSE. | |
| US4172173A (en) * | 1976-06-30 | 1979-10-23 | Celanese Corporation | Ethylene-vinyl acetate polymer binders for non-woven fabrics |
| US4221562A (en) * | 1978-05-04 | 1980-09-09 | Scott Paper Company | Bleed-fast cationic dyestuffs |
| US4851291A (en) * | 1986-06-19 | 1989-07-25 | The United States Of America As Represented By The Secretary Of Agriculture | Temperature adaptable textile fibers and method of preparing same |
| US4900324A (en) * | 1987-05-18 | 1990-02-13 | The United States Of America, As Represented By The Secretary Of Agriculture | Agents for non-formaldehyde durable press finishing and textile products therefrom |
| EP1264030A2 (en) * | 2000-02-07 | 2002-12-11 | The Procter & Gamble Company | Enhanced fabric comprising substrates and process to provide same |
| BR0108052A (en) * | 2000-02-07 | 2003-01-28 | Procter & Gamble | Improved fabric comprising substrates and process for providing the same |
| CN113372519A (en) * | 2020-02-25 | 2021-09-10 | 中国石油大学(华东) | Polyformaldehyde alcohol ether polymer, preparation method and application thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2207740A (en) * | 1935-04-18 | 1940-07-16 | Heberlein Patent Corp | Process for producing water-repellent cellulose-containing materials and products therefrom |
| BE438375A (en) * | 1939-04-22 | |||
| US2360477A (en) * | 1941-04-11 | 1944-10-17 | Gustavus J Esselen Inc | Polymeric acetals and process of forming same |
| US2350350A (en) * | 1941-05-06 | 1944-06-06 | Du Pont | Glycol formals |
-
0
- NL NL193521D patent/NL193521A/xx unknown
- BE BE534687D patent/BE534687A/xx unknown
-
1954
- 1954-01-08 US US403057A patent/US2785949A/en not_active Expired - Lifetime
- 1954-12-16 GB GB36455/54A patent/GB776468A/en not_active Expired
-
1955
- 1955-01-06 FR FR1131435D patent/FR1131435A/en not_active Expired
- 1955-05-30 ES ES0222108A patent/ES222108A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES222108A1 (en) | 1956-01-01 |
| NL193521A (en) | |
| US2785949A (en) | 1957-03-19 |
| FR1131435A (en) | 1957-02-21 |
| BE534687A (en) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB776468A (en) | Acetal condensation products and process for dimensional control of textile and paper materials | |
| US2786081A (en) | Acetal condensation products | |
| US2785947A (en) | Process for producing durable mechanical effects on cellulose fabrics by applying acetals and products resulting therefrom | |
| US2878294A (en) | Polymeric acetals | |
| US2643236A (en) | Method of preparing condensation products of pentaerythritol and glyoxal | |
| US2902470A (en) | Phenol modified polyacetals | |
| US2785995A (en) | Process of improving the wet strength and dimensional stability of cellulose paper fibers and regenerated cellulose films by reacting them with acetals and products produced thereby | |
| US2774691A (en) | Treatment of textile materials and product | |
| US3824232A (en) | Process for manufacturing water soluble alkoxylated methylol melamines | |
| GB1049463A (en) | New hydroxyaryl-1,3,5-triazines, process for their preparation and their use | |
| US2711971A (en) | Methylol acetone resin precondensate and method of impregnating fabrics therewith | |
| US3652583A (en) | Condensates of imidazolidone derivatives and polyalkylene glycol useful for improving textile materials | |
| US3953505A (en) | Carbamide-formaldehyde condensation products, their manufacture and use | |
| GB763268A (en) | Process for the fixation of effects mechanically produced on textile materials | |
| GB587572A (en) | Improvements relating to the finishing of textiles | |
| US2889192A (en) | Method of treating cellulose-containing textile materials, materials so treated and diester composition therefor | |
| GB897757A (en) | 1, 3-di-methylol-4, 5-bis(alkoxy)-2-imidazolidinones and use of the same | |
| GB1581116A (en) | Preparation of aqueous melamine-formaldehyde resin solutions | |
| US3518043A (en) | Hexahydropyrimidone derivatives and a method of finishing textile material | |
| US2903328A (en) | Process for the dimensional control of cellulosic materials | |
| US3215489A (en) | Process of treating cellulose textile material | |
| US3784641A (en) | N,n-bis alkoxymethyl and n,n-dimethylol sulfonamides | |
| US3150190A (en) | Acetal condensation products and their preparation | |
| GB1105250A (en) | Improvements in the treatment of cellulosic fabrics | |
| GB877582A (en) | Improvements in or relating to a method of finishing textile materials |