EP0681053A1 - Carboxygruppenmodifizierte Cellulose- oder Acrylfasern und Verfahren zur Herstellung derselben - Google Patents
Carboxygruppenmodifizierte Cellulose- oder Acrylfasern und Verfahren zur Herstellung derselben Download PDFInfo
- Publication number
- EP0681053A1 EP0681053A1 EP94303133A EP94303133A EP0681053A1 EP 0681053 A1 EP0681053 A1 EP 0681053A1 EP 94303133 A EP94303133 A EP 94303133A EP 94303133 A EP94303133 A EP 94303133A EP 0681053 A1 EP0681053 A1 EP 0681053A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fiber
- graft
- weight
- comonomer
- acrylonitrile
- 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.)
- Granted
Links
- 229920003043 Cellulose fiber Polymers 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 15
- 239000001913 cellulose Substances 0.000 title abstract description 4
- 229920002972 Acrylic fiber Polymers 0.000 title description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title description 7
- 239000000835 fiber Substances 0.000 claims abstract description 82
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 26
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 17
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims abstract description 15
- -1 hydroxyalkyl methacrylate Chemical compound 0.000 claims abstract description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000012736 aqueous medium Substances 0.000 claims abstract description 11
- 239000000758 substrate Substances 0.000 claims description 36
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 12
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 11
- 238000007334 copolymerization reaction Methods 0.000 claims description 8
- 229910001448 ferrous ion Inorganic materials 0.000 claims description 8
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 235000003891 ferrous sulphate Nutrition 0.000 claims description 7
- 239000011790 ferrous sulphate Substances 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920000742 Cotton Polymers 0.000 claims description 5
- 244000025254 Cannabis sativa Species 0.000 claims description 4
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims description 4
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical group CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 229920000297 Rayon Polymers 0.000 claims description 4
- 235000009120 camo Nutrition 0.000 claims description 4
- 235000005607 chanvre indien Nutrition 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- IMBKASBLAKCLEM-UHFFFAOYSA-L ferrous ammonium sulfate (anhydrous) Chemical compound [NH4+].[NH4+].[Fe+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O IMBKASBLAKCLEM-UHFFFAOYSA-L 0.000 claims description 4
- 239000011487 hemp Substances 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 229940010514 ammonium ferrous sulfate Drugs 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 2
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 claims description 2
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 claims description 2
- SMTDFMMXJHYDDE-UHFFFAOYSA-N 2-prop-1-enylpyridine Chemical compound CC=CC1=CC=CC=N1 SMTDFMMXJHYDDE-UHFFFAOYSA-N 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- 229960002089 ferrous chloride Drugs 0.000 claims description 2
- 229960001781 ferrous sulfate Drugs 0.000 claims description 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 2
- 239000002964 rayon Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000003352 sequestering agent Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- RHPXYIKALIRNFA-UHFFFAOYSA-L disodium;2-[carboxylatomethyl(carboxymethyl)amino]acetate Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CC([O-])=O RHPXYIKALIRNFA-UHFFFAOYSA-L 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000006957 Michael reaction Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 240000008564 Boehmeria nivea Species 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
- 229920002821 Modacrylic Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical compound [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 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
- 239000011976 maleic acid Substances 0.000 description 1
- 229910001437 manganese ion Inorganic materials 0.000 description 1
- 229910052603 melanterite Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007787 solid Substances 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
- 238000005303 weighing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 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
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
- D06M14/08—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of synthetic origin
- D06M14/10—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of synthetic origin of macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
- D06M14/02—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin
- D06M14/04—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin of vegetal origin, e.g. cellulose or derivatives thereof
Definitions
- This invention relates generally to a fiber modified with carboxyl groups and, more specifically, to a cellulose or acrylonitrile fiber to which methacrylic acid or a hydroxyalkyl methacrylate is graft-copolymerized.
- the present invention is also directed to a process for producing such a modified fiber.
- One known method of introducing carboxyl groups into a cellulose fiber includes reacting monochloroacetic acid with the cellulose fiber. Because of the introduction of carboxylic groups, the cellulose fiber thus obtained has improved hydrophilicity and is capable of absorbing basic, bad odor substances such as amines and ammonia. The known method has, however, a problem that it is difficult to homogeneously react the monochloroacetic acid with a solid, bulky mass of cellulose fibers because the reaction is exothermic.
- An acrylonitrile fiber has properties similar to wool but has a defect that the moisture or damp absorbing power is poor. No effective method is however known to impart hydrophilicity to the acrylonitrile fiber.
- a method is known in which a vinyl monomer having an acidic group is graft-copolymerized to a polyester or polyamide fiber using an organic peroxide such as benzoyl peroxide.
- a modified fiber comprising a substrate fiber selected from the group consisting of cellulose fibers and acrylonitrile-series fibers, and a graft comonomer graft-copolymerized to said substrate fiber in an amount of 3-60 % by weight based on the weight of said substrate fiber, said graft comonomer being at least one member selected from the group consisting of methacrylic acid and hydroxyalkyl methacrylates.
- the present invention provides a process for the production of a modified fiber comprising graft-copolymerizing a graft comonomer to a substrate fiber in an aqueous medium containing hydrogen peroxide and a source of ferrous ion, said substrate fiber being selected from the group consisting of cellulose fibers and acrylonitrile-series fibers, and said graft comonomer being at least one member selected from the group consisting of methacrylic acid and hydroxyalkyl methacrylates.
- the substrate fiber used in the present invention which is selected from cellulose fibers and acrylonitrile-series fibers, may be any desired form such as a yarn, a cotton, a woven or non-woven fabric, a filament or a tow. If desired, the substrate fiber may be used in combination with another fiber.
- the cellulose fiber may be, for example, cotton or hemp.
- acrylonitrile-series fiber used in the present specification and claims is intended to refer to a fiber formed of a homopolymer acrylonitrile or a copolymer of acrylonitrile with a vinyl comonomer.
- Examples of the vinyl comonomers include methyl acrylate, vinyl acetate, acrylic acid, methacrylic acid, vinyl chloride, vinylidene chloride, methylvinylpyridine, styrenesulfonic acid and mixtures thereof.
- the copolymer of acrylonitrile with the vinyl comonomer generally has a content of the acrylonitrile of at least 20 % by weight, preferably 35-90 % by weight.
- the substrate fiber is graft-copolymerized and linked a graft comonomer in an amount of 3-60 % by weight based on the weight of the substrate fiber.
- the graft comonomer is selected from acrylic acid and hydroxyalkyl methacrylates such as 2-hydroxyethyl methacrylate and 2-hydroxypropyl methacrylate.
- the graft comonomer is preferably methacrylic acid and is graft-copolymerized thereto in an amount of preferably 5-30 % by weight, more preferably 7-15 % by weight.
- the graft comonomer is preferably copolymerized in an amount of 5-40 % by weight.
- the modified fiber according to the present invention may be prepared by graft-copolymerizing the graft comonomer to the substrate fiber in an aqueous medium containing hydrogen peroxide and a source of ferrous ion.
- the ferrous ions source is preferably a ferrous salt such as ferrous sulfate, ferrous chloride, ammonium ferrous sulfate or ferrous nitrate.
- the ferrous in salt is preferably present in the aqueous medium in an amount providing a ferrous ion concentration of 0.5-5 mmol/liter, more preferably 1.0-2.5 mmol/liter when the substrate fiber is a cellulose fiber and 0.7-1.6 mmol/liter when the substrate fiber is an acrylonitrile-series fiber.
- the concentration of the hydrogen peroxide in the aqueous medium is preferably 0.01-0.1 mol/liter, more preferably 0.02-0.05 mol/liter when the substrate fiber is a cellulose fiber and 0.03-0.06 mol/liter when the substrate fiber is an acrylonitrile-series fiber.
- the hydrogen peroxide and the ferrous ion source together serve to accelerate the graft copolymerization.
- the aqueous medium may contain an acid in an amount of 2-4 mmol/liter, preferably 2.5-3.5 mmol/liter, if desired.
- the acid serves to enhance the grafting rate of the graft comonomer.
- suitable acids include sulfuric acid, hydrochloric acid, phosphoric acid and formic acid.
- the aqueous medium may further contain a sequestering agent such as EDTA, NTA or a phosphoric acid-type or sulfonic acid-type agent.
- the graft comonomer is generally used in an amount of 5-100 parts by weight, preferably 10-60 parts by weight, per 100 parts by weight of the substrate fiber and wherein the weight ratio of said aqueous medium to said substrate fiber is generally 5:1 to 50:1, preferably 5:1 to 20:1 when the substrate fiber is a cellulose fiber and 5:1 to 15:1 when the substrate fiber is an acrylonitrile-series fiber.
- the graft copolymerization is generally performed at a temperature and for a period of time so that the graft monomer is grafted to the substrate fiber in an amount of 3-60 % by weight based on the weight of the substrate fiber.
- the graft degree (weight percentage of the grafted comonomer based on the weight of the substrate fiber) is 5-30 % by weight, more preferably 7-15 % by weight, when a cellulose fiber is used as the substrate fiber.
- the graft degree is preferably 3-60 % by weight, more preferably 5-40 % by weight, when a methacrylonitrile-series fiber is used as the substrate fiber.
- the graft copolymerization is generally performed at a temperature of 40°-110°C for 30-240 minutes.
- the graft copolymerization is preferably performed at 40°-100°C for 60-240 minutes, more preferably 40°-80°C for 90-180 minutes.
- the graft copolymerization is preferably performed at 70°-110°C for 30-180 minutes, more preferably 90°-100°C for 60-90 minutes.
- the carboxyl groups (-COOH) introduced into the substrate fiber by graft copolymerization of the graft comonomer may be converted into -COOM (M represents a cation) by reaction with a salt-forming cation.
- the cation may be, for example, sodium ion, calcium ion, ferrous ion, cupric ion, zinc ion, manganese ion, silver ion, quaternary ammonium ion or quaternary organic amine ion.
- the process according to the present invention uses a ferrous salt in a very small amount. Therefore, the modified fibers is not discolored and no specific step for the removal of the ferrous salt is required. Further, the reaction conditions for the modification treatment may be easily controlled so that the graft copolymerization can be homogeneously performed.
- the modified fibers of the present invention have improved hydrophilicity and serve to function as a good adsorbent not only for basic, bad odor substances such as ammonia and amines, but also for metal ions.
- Example 2 was repeated in the same manner as described except that hemp (ramie fiber) was used in lieu of the rayon staple.
- the modified hemp had a graft degree of 8.7 %.
- Example 6 was repeated in the same manner as described except that modacrylic fibers (Kanebo Acryl VE1 manufactured by Kanebo Co., Ltd.) was substituted for Toraylon.
- the modified acrylic fibers thus obtained had a graft degree of 8.1 %.
- Example 4 was repeated in the same manner as described except that 2-hydroxyethyl methacrylate was substituted for methacrylic acid.
- the modified acrylic fibers thus obtained had a graft degree of 9.3 %.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19940303133 EP0681053B1 (de) | 1994-04-29 | 1994-04-29 | Carboxygruppenmodifizierte Cellulose- oder Acrylfasern und Verfahren zur Herstellung derselben |
| DE69428980T DE69428980D1 (de) | 1994-04-29 | 1994-04-29 | Carboxygruppenmodifizierte Cellulose- oder Acrylfasern und Verfahren zur Herstellung derselben |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19940303133 EP0681053B1 (de) | 1994-04-29 | 1994-04-29 | Carboxygruppenmodifizierte Cellulose- oder Acrylfasern und Verfahren zur Herstellung derselben |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0681053A1 true EP0681053A1 (de) | 1995-11-08 |
| EP0681053B1 EP0681053B1 (de) | 2001-11-07 |
Family
ID=8217680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19940303133 Expired - Lifetime EP0681053B1 (de) | 1994-04-29 | 1994-04-29 | Carboxygruppenmodifizierte Cellulose- oder Acrylfasern und Verfahren zur Herstellung derselben |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0681053B1 (de) |
| DE (1) | DE69428980D1 (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2366568A (en) * | 2000-09-01 | 2002-03-13 | Unilever Plc | Method of treating fabric |
| WO2023190608A1 (ja) * | 2022-03-31 | 2023-10-05 | 株式会社カネカ | 熱可塑性モダクリル樹脂及びそれを含む熱可塑性モダクリル樹脂組成物 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2384867A1 (fr) * | 1977-03-21 | 1978-10-20 | Chemiefaser Lenzing Ag | Fibre a base de cellulose, reticulee en milieu humide, et son procede de fabrication |
| FR2387250A1 (fr) * | 1977-04-14 | 1978-11-10 | Chemiefaser Lenzing Ag | Fibres d'un polymere contenant des groupes hydroxyles avec polymerisation de greffage, procede pour leur production et leur application |
| EP0189163A2 (de) * | 1985-01-19 | 1986-07-30 | Taiyo Fishery Co., Ltd. | Verfahren zur Herstellung eines Wasser absorbierenden vernetzten Polymers |
| EP0262405A2 (de) * | 1986-08-29 | 1988-04-06 | Mitsubishi Petrochemical Company Limited | Verfahren zur Herstellung von wasserabsorbierendem, faserigem Material |
| US4743267A (en) * | 1982-06-21 | 1988-05-10 | International Yarn Corporation Of Tennessee | Process for improving polymer fiber properties and fibers produced thereby |
| JPH06184941A (ja) * | 1992-11-10 | 1994-07-05 | Nippon Sanmou Senshoku Kk | 改質セルロース繊維及びその製造方法 |
-
1994
- 1994-04-29 DE DE69428980T patent/DE69428980D1/de not_active Expired - Lifetime
- 1994-04-29 EP EP19940303133 patent/EP0681053B1/de not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2384867A1 (fr) * | 1977-03-21 | 1978-10-20 | Chemiefaser Lenzing Ag | Fibre a base de cellulose, reticulee en milieu humide, et son procede de fabrication |
| FR2387250A1 (fr) * | 1977-04-14 | 1978-11-10 | Chemiefaser Lenzing Ag | Fibres d'un polymere contenant des groupes hydroxyles avec polymerisation de greffage, procede pour leur production et leur application |
| US4743267A (en) * | 1982-06-21 | 1988-05-10 | International Yarn Corporation Of Tennessee | Process for improving polymer fiber properties and fibers produced thereby |
| EP0189163A2 (de) * | 1985-01-19 | 1986-07-30 | Taiyo Fishery Co., Ltd. | Verfahren zur Herstellung eines Wasser absorbierenden vernetzten Polymers |
| EP0262405A2 (de) * | 1986-08-29 | 1988-04-06 | Mitsubishi Petrochemical Company Limited | Verfahren zur Herstellung von wasserabsorbierendem, faserigem Material |
| JPH06184941A (ja) * | 1992-11-10 | 1994-07-05 | Nippon Sanmou Senshoku Kk | 改質セルロース繊維及びその製造方法 |
Non-Patent Citations (2)
| Title |
|---|
| DATABASE WPI Week 9431, Derwent World Patents Index; AN 94-253428 * |
| J.DAS, A.K. MOHANTY AND B.C. SINGH: "Fenton's Reagent Initiated Graft Copolymerization of Methyl Methacrylate onto Jute Fibers", TEXTILE RESEARCH JOURNAL., vol. 59, no. 9, September 1989 (1989-09-01), US, pages 525 - 529, XP000051475 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2366568A (en) * | 2000-09-01 | 2002-03-13 | Unilever Plc | Method of treating fabric |
| WO2023190608A1 (ja) * | 2022-03-31 | 2023-10-05 | 株式会社カネカ | 熱可塑性モダクリル樹脂及びそれを含む熱可塑性モダクリル樹脂組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0681053B1 (de) | 2001-11-07 |
| DE69428980D1 (de) | 2001-12-13 |
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