JPS6116901A - カルボキシメチルセルロ−スの第四アンモニウム塩及びその製造法 - Google Patents
カルボキシメチルセルロ−スの第四アンモニウム塩及びその製造法Info
- Publication number
- JPS6116901A JPS6116901A JP59138697A JP13869784A JPS6116901A JP S6116901 A JPS6116901 A JP S6116901A JP 59138697 A JP59138697 A JP 59138697A JP 13869784 A JP13869784 A JP 13869784A JP S6116901 A JPS6116901 A JP S6116901A
- Authority
- JP
- Japan
- Prior art keywords
- quaternary ammonium
- ammonium salt
- cmc
- group
- salt
- 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
- 229920002134 Carboxymethyl cellulose Polymers 0.000 title claims abstract description 46
- 235000010948 carboxy methyl cellulose Nutrition 0.000 title claims abstract description 45
- 150000003242 quaternary ammonium salts Chemical class 0.000 title claims abstract description 32
- 239000001768 carboxy methyl cellulose Substances 0.000 title claims abstract description 17
- 239000008112 carboxymethyl-cellulose Substances 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims abstract description 12
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 238000006467 substitution reaction Methods 0.000 claims abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 12
- 239000003960 organic solvent Substances 0.000 abstract description 5
- 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 description 3
- 239000008103 glucose Substances 0.000 abstract description 3
- 239000000084 colloidal system Substances 0.000 abstract description 2
- 239000002270 dispersing agent Substances 0.000 abstract description 2
- 239000002562 thickening agent Substances 0.000 abstract description 2
- 239000005518 polymer electrolyte Substances 0.000 abstract 1
- 229920003169 water-soluble polymer Polymers 0.000 abstract 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 17
- -1 cyclic quaternary ammonium salt Chemical class 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920002678 cellulose Polymers 0.000 description 9
- 239000001913 cellulose Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 3
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical class CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 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 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- QSRFYFHZPSGRQX-UHFFFAOYSA-N benzyl(tributyl)azanium Chemical compound CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 QSRFYFHZPSGRQX-UHFFFAOYSA-N 0.000 description 2
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 2
- WNBGYVXHFTYOBY-UHFFFAOYSA-N benzyl-dimethyl-tetradecylazanium Chemical compound CCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 WNBGYVXHFTYOBY-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- LNIYNESXCOYFPW-UHFFFAOYSA-N dibenzyl(dimethyl)azanium Chemical compound C=1C=CC=CC=1C[N+](C)(C)CC1=CC=CC=C1 LNIYNESXCOYFPW-UHFFFAOYSA-N 0.000 description 2
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 2
- GJSGYPDDPQRWPK-UHFFFAOYSA-N tetrapentylammonium Chemical compound CCCCC[N+](CCCCC)(CCCCC)CCCCC GJSGYPDDPQRWPK-UHFFFAOYSA-N 0.000 description 2
- FFYRIXSGFSWFAQ-UHFFFAOYSA-N 1-dodecylpyridin-1-ium Chemical compound CCCCCCCCCCCC[N+]1=CC=CC=C1 FFYRIXSGFSWFAQ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- SKGURMFKEAFAGD-CSYZDTNESA-N C([C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O)C1=CC=C(O)C=C1 Chemical class C([C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O)C1=CC=C(O)C=C1 SKGURMFKEAFAGD-CSYZDTNESA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910002226 La2O2 Inorganic materials 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- YFESUULOIHBYSW-UHFFFAOYSA-N azane 1-dodecylpyridin-1-ium Chemical compound N.CCCCCCCCCCCC[N+]1=CC=CC=C1 YFESUULOIHBYSW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical class CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- DXIVDWCVGRNPIW-UHFFFAOYSA-N dodecyl-hexadecyl-dimethylazanium Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC DXIVDWCVGRNPIW-UHFFFAOYSA-N 0.000 description 1
- VICYBMUVWHJEFT-UHFFFAOYSA-N dodecyltrimethylammonium ion Chemical compound CCCCCCCCCCCC[N+](C)(C)C VICYBMUVWHJEFT-UHFFFAOYSA-N 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- FZFZFCIODKYFEV-UHFFFAOYSA-N pentan-1-amine;hydrochloride Chemical compound Cl.CCCCCN FZFZFCIODKYFEV-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940113046 sorine Drugs 0.000 description 1
- ZBMZVLHSJCTVON-UHFFFAOYSA-N sotalol Chemical compound CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1 ZBMZVLHSJCTVON-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- RQPWVAXZWDTDPH-UHFFFAOYSA-N tridodecyl(methyl)azanium Chemical compound CCCCCCCCCCCC[N+](C)(CCCCCCCCCCCC)CCCCCCCCCCCC RQPWVAXZWDTDPH-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B11/00—Preparation of cellulose ethers
- C08B11/02—Alkyl or cycloalkyl ethers
- C08B11/04—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals
- C08B11/10—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals
- C08B11/12—Alkyl or cycloalkyl ethers with substituted hydrocarbon radicals substituted with acid radicals substituted with carboxylic radicals, e.g. carboxymethylcellulose [CMC]
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Cosmetics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pyridine Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59138697A JPS6116901A (ja) | 1984-07-03 | 1984-07-03 | カルボキシメチルセルロ−スの第四アンモニウム塩及びその製造法 |
| US06/748,775 US4617385A (en) | 1984-07-03 | 1985-06-25 | Quaternary ammonium salts of carboxymethylcellulose |
| EP85107919A EP0170053B1 (en) | 1984-07-03 | 1985-06-26 | Quaternary ammonium salts of carboxymethylcellulose |
| DE8585107919T DE3584483D1 (de) | 1984-07-03 | 1985-06-26 | Quaternaere ammoniumsalze von carboxymethylcellulose. |
| FI852617A FI78306C (fi) | 1984-07-03 | 1985-07-02 | Kvaternaera ammoniumsalter av karboximetylcellulosa. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59138697A JPS6116901A (ja) | 1984-07-03 | 1984-07-03 | カルボキシメチルセルロ−スの第四アンモニウム塩及びその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6116901A true JPS6116901A (ja) | 1986-01-24 |
| JPS6355522B2 JPS6355522B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-11-02 |
Family
ID=15228004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59138697A Granted JPS6116901A (ja) | 1984-07-03 | 1984-07-03 | カルボキシメチルセルロ−スの第四アンモニウム塩及びその製造法 |
Country Status (5)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5240774A (en) * | 1990-10-25 | 1993-08-31 | Matsushita Electric Industrial Co., Ltd. | Fluorocarbon-based coating film and method of manufacturing the same |
| JPWO2017138574A1 (ja) * | 2016-02-08 | 2019-02-21 | 日本製紙株式会社 | 変性カルボキシメチル化セルロースナノファイバー分散液およびその製造方法 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4877617A (en) * | 1985-12-11 | 1989-10-31 | Daicel Chemical Industries Ltd. | Fungicidal and bactericidal method |
| US4696677A (en) * | 1986-04-11 | 1987-09-29 | Merck & Co., Inc. | Quaternary ammonium salts of anionic gums |
| DE3820029A1 (de) * | 1988-06-13 | 1989-12-14 | Goldschmidt Ag Th | Betaingruppen enthaltende derivate der carboxymethylcellulose, deren herstellung und deren verwendung in kosmetischen zubereitungen |
| WO1998019534A1 (de) * | 1996-11-06 | 1998-05-14 | Bayer Aktiengesellschaft | Thermoplastische polysaccharidsalze |
| US6811885B1 (en) * | 1999-06-06 | 2004-11-02 | Agfa-Gevaert | Acid stable aqueous dispersion of metal particles and applications |
| AU2011240856B2 (en) * | 2010-04-12 | 2014-02-13 | Basf Se | Antimicrobial treatment of synthetic nonwoven textiles |
| IN2014DN07422A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2012-03-09 | 2015-04-24 | Friedrich Schiller Universität Jena | |
| US9334335B2 (en) * | 2012-11-30 | 2016-05-10 | Xerox Corporation | Surface layer |
| WO2015156759A1 (en) | 2014-04-07 | 2015-10-15 | Halliburton Energy Services, Inc. | Method of breaking metal-crosslinked polymers |
| US20230167601A1 (en) * | 2020-04-30 | 2023-06-01 | Basf Corporation | Antimicrobial textiles |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2853414A (en) * | 1953-12-02 | 1958-09-23 | American Sugar Refining Co | Water-insoluble complex of quaternary ammonium salt, a heavy-metal oxide, and an organic colloid and method of preparing same |
| US2881074A (en) * | 1955-07-29 | 1959-04-07 | Armour & Co | Growth promotant substances |
| US2972606A (en) * | 1956-05-31 | 1961-02-21 | Wyandotte Chemicals Corp | Catalytic aminoethylation of cellulose, cellulose derivatives or polyvinyl alcohol |
| FR1389419A (fr) * | 1962-04-13 | 1965-02-19 | Boots Pure Drug Co Ltd | Procédé de préparation de complexes de sels de phénanthridinium ou de quinoléinium |
| JPS58225101A (ja) * | 1982-06-22 | 1983-12-27 | Daicel Chem Ind Ltd | セルロ−スエステル誘導体及びその製造方法 |
| US4520192A (en) * | 1984-07-03 | 1985-05-28 | Daicel Chemical Industries Ltd. | Carboxyalkyl acetyl celluloses, their salts and a process for the preparation of them |
-
1984
- 1984-07-03 JP JP59138697A patent/JPS6116901A/ja active Granted
-
1985
- 1985-06-25 US US06/748,775 patent/US4617385A/en not_active Expired - Lifetime
- 1985-06-26 DE DE8585107919T patent/DE3584483D1/de not_active Expired - Lifetime
- 1985-06-26 EP EP85107919A patent/EP0170053B1/en not_active Expired - Lifetime
- 1985-07-02 FI FI852617A patent/FI78306C/fi not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5240774A (en) * | 1990-10-25 | 1993-08-31 | Matsushita Electric Industrial Co., Ltd. | Fluorocarbon-based coating film and method of manufacturing the same |
| JPWO2017138574A1 (ja) * | 2016-02-08 | 2019-02-21 | 日本製紙株式会社 | 変性カルボキシメチル化セルロースナノファイバー分散液およびその製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FI78306B (fi) | 1989-03-31 |
| EP0170053A2 (en) | 1986-02-05 |
| US4617385A (en) | 1986-10-14 |
| FI852617L (fi) | 1986-01-04 |
| DE3584483D1 (de) | 1991-11-28 |
| EP0170053B1 (en) | 1991-10-23 |
| EP0170053A3 (en) | 1987-05-13 |
| FI852617A0 (fi) | 1985-07-02 |
| FI78306C (fi) | 1989-07-10 |
| JPS6355522B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-11-02 |
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