GB919390A - Polyvinyl alcohol fibres having excellent dyeability and whiteness - Google Patents
Polyvinyl alcohol fibres having excellent dyeability and whitenessInfo
- Publication number
- GB919390A GB919390A GB11944/61A GB1194461A GB919390A GB 919390 A GB919390 A GB 919390A GB 11944/61 A GB11944/61 A GB 11944/61A GB 1194461 A GB1194461 A GB 1194461A GB 919390 A GB919390 A GB 919390A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polyvinyl alcohol
- starch
- aqueous solutions
- sulphuric acid
- urea
- 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
- 239000004372 Polyvinyl alcohol Substances 0.000 title abstract 8
- 229920002451 polyvinyl alcohol Polymers 0.000 title abstract 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 7
- 239000007864 aqueous solution Substances 0.000 abstract 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- 229920002472 Starch Polymers 0.000 abstract 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 6
- 239000008107 starch Substances 0.000 abstract 6
- 235000019698 starch Nutrition 0.000 abstract 6
- 239000001117 sulphuric acid Substances 0.000 abstract 6
- 235000011149 sulphuric acid Nutrition 0.000 abstract 6
- 239000004202 carbamide Substances 0.000 abstract 5
- 239000007795 chemical reaction product Substances 0.000 abstract 5
- 229920002554 vinyl polymer Polymers 0.000 abstract 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 4
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 4
- 235000011152 sodium sulphate Nutrition 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000001768 carboxy methyl cellulose Substances 0.000 abstract 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 abstract 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- 229920000084 Gum arabic Polymers 0.000 abstract 2
- 241000978776 Senegalia senegal Species 0.000 abstract 2
- 229930006000 Sucrose Natural products 0.000 abstract 2
- 239000000205 acacia gum Substances 0.000 abstract 2
- 235000010489 acacia gum Nutrition 0.000 abstract 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 abstract 2
- MWAZVPWTTWPXJF-UHFFFAOYSA-N acetic acid;urea Chemical compound CC(O)=O.NC(N)=O MWAZVPWTTWPXJF-UHFFFAOYSA-N 0.000 abstract 2
- 150000001720 carbohydrates Chemical class 0.000 abstract 2
- 239000008103 glucose Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 abstract 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 abstract 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 abstract 2
- 238000009987 spinning Methods 0.000 abstract 2
- 239000005720 sucrose Substances 0.000 abstract 2
- 238000011282 treatment Methods 0.000 abstract 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 abstract 1
- RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical compound O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 abstract 1
- 241000416162 Astragalus gummifer Species 0.000 abstract 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 abstract 1
- 239000004375 Dextrin Substances 0.000 abstract 1
- 229920001353 Dextrin Polymers 0.000 abstract 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 abstract 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 abstract 1
- 229920001612 Hydroxyethyl starch Polymers 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 abstract 1
- 229920001615 Tragacanth Polymers 0.000 abstract 1
- 238000006359 acetalization reaction Methods 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 abstract 1
- 239000001166 ammonium sulphate Substances 0.000 abstract 1
- 235000011130 ammonium sulphate Nutrition 0.000 abstract 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 abstract 1
- 229920003064 carboxyethyl cellulose Polymers 0.000 abstract 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 abstract 1
- 238000010622 cold drawing Methods 0.000 abstract 1
- 235000019425 dextrin Nutrition 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000005038 ethylene vinyl acetate Substances 0.000 abstract 1
- 239000004715 ethylene vinyl alcohol Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 abstract 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 abstract 1
- 229940050526 hydroxyethylstarch Drugs 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- -1 methyl sucrose Chemical compound 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 abstract 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 abstract 1
- 229920002689 polyvinyl acetate Polymers 0.000 abstract 1
- 239000011118 polyvinyl acetate Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
- C08L29/02—Homopolymers or copolymers of unsaturated alcohols
- C08L29/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/28—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F6/34—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds comprising unsaturated alcohols, acetals or ketals as the major constituent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
-
- 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
- Y10S8/10—Polyvinyl halide esters or alcohol fiber modification
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
Abstract
Polyvinyl alcohol fibres are spun from aqueous solutions comprising (A) polyvinyl alcohol containing more than 98 mole per cent of vinyl alcohol units, (B) a water-soluble polyvinyl alcohol-urea derivative containing at least 80 mole per cent, and preferably 80 to 99 mole per cent vinyl alcohol units, the urea-derived nitrogen content based on B being 0,1 to 6,0% by weight, and based on A and B being 0,05 to 4,5% by weight, and optionally (C) a water-soluble saccharide or water-soluble derivative thereof. B may be prepared by reacting urea with polyvinyl alcohol, completely or partially saponified polyvinyl acetate or ethylene-vinyl acetate copolymer, or partially acetalized polyvinyl alcohol, either in the fused state or in the presence of a solvent such as dimethyl formamide. Specified saccharides and derivatives are glucose, sucrose, starch, dextrin, gum arabic, gum tragacanth, methyl glucose, acetyl glycose, methyl sucrose, methyl starch, ethyl starch, carboxymethyl starch, hydroxyethyl starch, cyanoethyl starch, carboxymethyl cellulose, carboxyethyl cellulose and hydroxyethyl cellulose. Fibres may be dry spun or wet spun into aqueous solutions of salts, such as sodium sulphate and ammonium sulphate. The fibres may be subjected to physical and chemical treatments such as cold-drawing, hot-drawing, heat treatment at constant length, heat-shrinkage, chromination or titanation, and may be acetalized by reacting with an aldehyde containing 1 to 12 carbon atoms, e.g. formaldehyde, acetaldehyde and benzaldehyde, in the presence of mineral acids such as sulphuric, hydrochloric, phosphoric and periodic acid, salt thereof, organic solvents and surface active agents. Examples describe the spinning of fibres from spinning solutions comprising polyvinyl alcohol and (I, III and IV) saponified polyvinyl acetate-urea reaction products, (V) polyvinyl alcohol-urea reaction product and (VI) ethylene-vinyl alcohol copolymer-urea reaction product; polyvinyl alcohol and saponified polyvinyl acetate-urea reaction products together with (VII and XII) starch, (IX) sodium carboxymethyl cellulose and (XI) glucose; and polyvinyl alcohol and polyvinyl alcohol-urea reaction products together with (X) gum arabic and (XIII) sodium carboxymethyl cellulose; and the formalization or benzalization of I, VI and XI with aqueous solutions containing formaldehyde or benzaldehyde, sulphuric acid and methanol; the treatment of V and XI with aqueous solutions comprising sodium periodate, sulphuric acid and sodium sulphate; the formalization of VII with aqueous solutions comprising formaldehyde, sulphuric acid and sodium sulphate; the benzalization of VII with aqueous compositions comprising benzaldehyde, sulphuric acid and methanol; the formalization of IX with aqueous solutions comprising formaldehyde and sulphuric acid and the mixed acetalization of XIII with aqueous solutions comprising formaldehyde, b -cyclohexylamino butyraldehyde, sulphuric acid and sodium sulphate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4857560 | 1960-12-14 | ||
| JP18361 | 1961-01-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB919390A true GB919390A (en) | 1963-02-27 |
Family
ID=26333104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11944/61A Expired GB919390A (en) | 1960-12-14 | 1961-04-04 | Polyvinyl alcohol fibres having excellent dyeability and whiteness |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3200178A (en) |
| DE (2) | DE1494654A1 (en) |
| GB (1) | GB919390A (en) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH394503A (en) * | 1962-08-03 | 1965-06-30 | Sulzer Ag | Process for producing lost models for the precision casting process |
| US5110678A (en) * | 1989-04-27 | 1992-05-05 | Kuraray Company Limited | Synthetic polyvinyl alcohol fiber and process for its production |
| US7235592B2 (en) * | 2004-10-12 | 2007-06-26 | Zimmer Gmbh | PVA hydrogel |
| WO2006091706A1 (en) | 2005-02-23 | 2006-08-31 | Zimmer Technology, Inc. | Blend hydrogels and methods of making |
| US7571295B2 (en) * | 2005-08-04 | 2009-08-04 | Intel Corporation | Memory manager for heterogeneous memory control |
| US20070098799A1 (en) * | 2005-10-28 | 2007-05-03 | Zimmer, Inc. | Mineralized Hydrogels and Methods of Making and Using Hydrogels |
| US8262730B2 (en) * | 2005-12-07 | 2012-09-11 | Zimmer, Inc. | Methods of bonding or modifying hydrogels using irradiation |
| US20070141108A1 (en) * | 2005-12-20 | 2007-06-21 | Zimmer, Inc. | Fiber-reinforced water-swellable articles |
| DE602006017160D1 (en) * | 2005-12-22 | 2010-11-11 | Zimmer Inc | Perfluorocyclobutane crosslinked hydrogels |
| US8110242B2 (en) * | 2006-03-24 | 2012-02-07 | Zimmer, Inc. | Methods of preparing hydrogel coatings |
| US7731988B2 (en) | 2007-08-03 | 2010-06-08 | Zimmer, Inc. | Multi-polymer hydrogels |
| US20090043398A1 (en) * | 2007-08-09 | 2009-02-12 | Zimmer, Inc. | Method of producing gradient articles by centrifugation molding or casting |
| US8062739B2 (en) * | 2007-08-31 | 2011-11-22 | Zimmer, Inc. | Hydrogels with gradient |
| US7947784B2 (en) * | 2007-11-16 | 2011-05-24 | Zimmer, Inc. | Reactive compounding of hydrogels |
| US8034362B2 (en) | 2008-01-04 | 2011-10-11 | Zimmer, Inc. | Chemical composition of hydrogels for use as articulating surfaces |
| TWI548655B (en) * | 2012-10-22 | 2016-09-11 | 積水特殊化學美國有限責任公司 | Pvp copolymer for harsh chemical packaging |
| JP6003794B2 (en) | 2013-05-02 | 2016-10-05 | 日立金属株式会社 | Rubber hose manufacturing method |
| EP3941951A1 (en) * | 2019-03-18 | 2022-01-26 | UPM-Kymmene Corporation | A method for manufacturing thermoplastic poly(vinyl alcohol) derivative in a melt state reaction and products thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2236061A (en) * | 1937-05-27 | 1941-03-25 | Du Pont | Method of making films, threads, and the like |
| US2277782A (en) * | 1939-05-03 | 1942-03-31 | Carbide & Carbon Chem Corp | Crimping materials containing synthetic textile fibers |
| US2636803A (en) * | 1950-02-04 | 1953-04-28 | Du Pont | Polyvinyl alcohol fibers and process of treating |
| US2977183A (en) * | 1951-12-19 | 1961-03-28 | Air Reduction | Process of improving the dyeing properties of polyvinyl alcohol fibers |
| US2906594A (en) * | 1955-12-21 | 1959-09-29 | Air Reduction | Polyvinyl alcohol filaments of improved dye affinity and method of preparation |
| BE564771A (en) * | 1957-02-13 | |||
| US3023182A (en) * | 1958-01-18 | 1962-02-27 | Kurashiki Rayon Co | Polyvinyl alcohol fibers of improved dyeability |
| US2890927A (en) * | 1958-01-24 | 1959-06-16 | Mitsubishi Rayon Co | Production of fibers made of or containing polyvinyl alcohol |
| GB888276A (en) * | 1958-05-26 | 1962-01-31 | Kurashiki Rayon Kk | Polyvinyl alcohol fibre production |
| GB934087A (en) * | 1960-12-08 | 1963-08-14 | Kurashiki Rayon Kk | Method of manufacturing water soluble polyvinyl alcohol derivatives |
-
1961
- 1961-04-04 GB GB11944/61A patent/GB919390A/en not_active Expired
- 1961-04-27 DE DE19611494654 patent/DE1494654A1/en active Pending
- 1961-04-27 DE DE19611469098 patent/DE1469098A1/en active Pending
- 1961-12-07 US US157850A patent/US3200178A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3200178A (en) | 1965-08-10 |
| DE1469098A1 (en) | 1969-03-20 |
| DE1494654A1 (en) | 1970-10-15 |
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