JPH0376322B2 - - Google Patents

Info

Publication number: JPH0376322B2
Authority: JP; Japan
Prior art keywords: cellulose; polymerization; polymer; methanol; graft copolymer
Prior art date: 1983-09-22
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

Application number

JP17569883A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6067501A (ja

Inventor

Takeo Saegusa

Shiro Kobayashi

Murao Kaku

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Daicel Corp

Original Assignee

Daicel Chemical Industries Ltd

Priority date (The priority date 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 date listed.)

1983-09-22

Filing date

1983-09-22

Publication date

1991-12-05

1983-09-22 Application filed by Daicel Chemical Industries Ltd filed Critical Daicel Chemical Industries Ltd

1983-09-22 Priority to JP17569883A priority Critical patent/JPS6067501A/ja

1985-04-17 Publication of JPS6067501A publication Critical patent/JPS6067501A/ja

1991-12-05 Publication of JPH0376322B2 publication Critical patent/JPH0376322B2/ja

Status Granted legal-status Critical Current

Links

229920002678 cellulose Polymers 0.000 claims description 46
239000001913 cellulose Substances 0.000 claims description 46
229920000578 graft copolymer Polymers 0.000 claims description 20
150000000376 2-oxazolines Chemical class 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 7
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
150000003459 sulfonic acid esters Chemical class 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
235000010980 cellulose Nutrition 0.000 description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
229920000642 polymer Polymers 0.000 description 24
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 14
238000006116 polymerization reaction Methods 0.000 description 12
229920002301 cellulose acetate Polymers 0.000 description 10
GUXJXWKCUUWCLX-UHFFFAOYSA-N 2-methyl-2-oxazoline Chemical compound CC1=NCCO1 GUXJXWKCUUWCLX-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
238000010559 graft polymerization reaction Methods 0.000 description 6
229920001519 homopolymer Polymers 0.000 description 6
238000002329 infrared spectrum Methods 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
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 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000003505 polymerization initiator Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
229920001747 Cellulose diacetate Polymers 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
239000003999 initiator Substances 0.000 description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
230000000379 polymerizing effect Effects 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
238000010538 cationic polymerization reaction Methods 0.000 description 2
YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
238000003328 mesylation reaction Methods 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
239000003607 modifier Substances 0.000 description 2
239000000178 monomer Substances 0.000 description 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
-1 poly(N-acetylethyleneimine) Polymers 0.000 description 2
239000002685 polymerization catalyst Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000007070 tosylation reaction Methods 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
NYEZZYQZRQDLEH-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1=NCCO1 NYEZZYQZRQDLEH-UHFFFAOYSA-N 0.000 description 1
ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 1
PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000002216 antistatic agent Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
229920006218 cellulose propionate Polymers 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
ZEDPQIJYJCPIRM-UHFFFAOYSA-N dimethyl benzonitrile Natural products CC1=CC=CC(C#N)=C1C ZEDPQIJYJCPIRM-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
238000005517 mercerization Methods 0.000 description 1
238000000034 method Methods 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
239000002954 polymerization reaction product Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000004513 sizing Methods 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Polysaccharides And Polysaccharide Derivatives (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

JP17569883A 1983-09-22 1983-09-22 セルロ−スグラフト共重合体及びその製造法 Granted JPS6067501A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP17569883A JPS6067501A (ja)	1983-09-22	1983-09-22	セルロ−スグラフト共重合体及びその製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP17569883A JPS6067501A (ja)	1983-09-22	1983-09-22	セルロ−スグラフト共重合体及びその製造法

Publications (2)

Publication Number	Publication Date
JPS6067501A JPS6067501A (ja)	1985-04-17
JPH0376322B2 true JPH0376322B2 (fr)	1991-12-05

Family

ID=16000680

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP17569883A Granted JPS6067501A (ja)	1983-09-22	1983-09-22	セルロ−スグラフト共重合体及びその製造法

Country Status (1)

Country	Link
JP (1)	JPS6067501A (fr)

1983
- 1983-09-22 JP JP17569883A patent/JPS6067501A/ja active Granted

Also Published As

Publication number	Publication date
JPS6067501A (ja)	1985-04-17

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