CA2078876A1 - Preparation d'esters cellulosiques de faible masse moleculaire - Google Patents

Preparation d'esters cellulosiques de faible masse moleculaire

Info

Publication number: CA2078876A1
Authority: CA; Canada
Prior art keywords: cellulose; anhydride; cellulose ester; mixture; group
Prior art date: 1990-04-16
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.): Abandoned

Application number

CA 2078876

Other languages

English (en)

Inventor

Charles M. Buchanan

Stephen W. Parker

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.)

Eastman Kodak Co

Original Assignee

Individual

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.)

1990-04-16

Filing date

1991-04-12

Publication date

1991-10-17

1991-04-12 Application filed by Individual filed Critical Individual

1991-10-17 Publication of CA2078876A1 publication Critical patent/CA2078876A1/fr

Status Abandoned legal-status Critical Current

Links

229920002678 cellulose Polymers 0.000 title claims abstract description 127
238000002360 preparation method Methods 0.000 title abstract description 10
238000000034 method Methods 0.000 claims abstract description 75
230000008569 process Effects 0.000 claims abstract description 70
239000001913 cellulose Substances 0.000 claims abstract description 66
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 58
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 43
230000007062 hydrolysis Effects 0.000 claims abstract description 42
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 42
-1 aryl anhydride Chemical class 0.000 claims abstract description 33
238000006243 chemical reaction Methods 0.000 claims abstract description 25
239000002904 solvent Substances 0.000 claims abstract description 21
229920000642 polymer Polymers 0.000 claims abstract description 20
239000002253 acid Substances 0.000 claims abstract description 16
229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 14
239000011707 mineral Substances 0.000 claims abstract description 14
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 59
239000000203 mixture Substances 0.000 claims description 32
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 20
238000006467 substitution reaction Methods 0.000 claims description 18
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 13
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 9
229920002301 cellulose acetate Polymers 0.000 claims description 8
229920006217 cellulose acetate butyrate Polymers 0.000 claims description 7
229920008347 Cellulose acetate propionate Polymers 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
229920002284 Cellulose triacetate Polymers 0.000 claims description 5
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical group O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 5
229920001727 cellulose butyrate Polymers 0.000 claims description 5
238000004821 distillation Methods 0.000 claims description 5
238000001694 spray drying Methods 0.000 claims description 5
125000003107 substituted aryl group Chemical group 0.000 claims description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
229920006218 cellulose propionate Polymers 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
230000001376 precipitating effect Effects 0.000 claims description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 claims description 3
PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 3
PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 claims description 3
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 claims description 3
PBBAFLCORNAZCD-UHFFFAOYSA-N nonanoyl nonanoate Chemical compound CCCCCCCCC(=O)OC(=O)CCCCCCCC PBBAFLCORNAZCD-UHFFFAOYSA-N 0.000 claims description 3
230000003381 solubilizing effect Effects 0.000 claims description 3
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
239000000047 product Substances 0.000 claims 10
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 claims 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
150000008065 acid anhydrides Chemical class 0.000 claims 1
239000012467 final product Substances 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
150000005691 triesters Chemical class 0.000 abstract description 22
150000002148 esters Chemical class 0.000 abstract description 16
239000011541 reaction mixture Substances 0.000 abstract description 9
238000002955 isolation Methods 0.000 abstract description 5
230000035484 reaction time Effects 0.000 abstract description 5
125000002252 acyl group Chemical group 0.000 abstract description 4
230000015572 biosynthetic process Effects 0.000 abstract description 4
238000000576 coating method Methods 0.000 abstract description 3
230000004580 weight loss Effects 0.000 abstract description 3
239000011248 coating agent Substances 0.000 abstract description 2
238000011065 in-situ storage Methods 0.000 abstract 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 26
238000005481 NMR spectroscopy Methods 0.000 description 15
239000003153 chemical reaction reagent Substances 0.000 description 14
238000010561 standard procedure Methods 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
235000011149 sulphuric acid Nutrition 0.000 description 8
230000032050 esterification Effects 0.000 description 7
238000005886 esterification reaction Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
238000005227 gel permeation chromatography Methods 0.000 description 6
229940081735 acetylcellulose Drugs 0.000 description 5
230000015556 catabolic process Effects 0.000 description 5
238000006731 degradation reaction Methods 0.000 description 5
235000019260 propionic acid Nutrition 0.000 description 5
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
239000004793 Polystyrene Substances 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
229920002223 polystyrene Polymers 0.000 description 4
238000001556 precipitation Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
125000001589 carboacyl group Chemical group 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 1
ZAMLGGRVTAXBHI-UHFFFAOYSA-N 3-(4-bromophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(CC(O)=O)C1=CC=C(Br)C=C1 ZAMLGGRVTAXBHI-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
229920000856 Amylose Polymers 0.000 description 1
229920003043 Cellulose fiber Polymers 0.000 description 1
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 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229920001131 Pulp (paper) Polymers 0.000 description 1
UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
235000019504 cigarettes Nutrition 0.000 description 1
239000008199 coating composition Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
238000012667 polymer degradation Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000004753 textile Substances 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
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/06—Cellulose acetate, e.g. mono-acetate, di-acetate or tri-acetate
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/02—Catalysts used for the esterification
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/22—Post-esterification treatments, including purification
- C08B3/24—Hydrolysis or ripening

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Materials Engineering (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

CA 2078876 1990-04-16 1991-04-12 Preparation d'esters cellulosiques de faible masse moleculaire Abandoned CA2078876A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US509,535		1983-06-30
US50953590A	1990-04-16	1990-04-16

Publications (1)

Publication Number	Publication Date
CA2078876A1 true CA2078876A1 (fr)	1991-10-17

Family

ID=24027033

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2078876 Abandoned CA2078876A1 (fr)	1990-04-16	1991-04-12	Preparation d'esters cellulosiques de faible masse moleculaire

Country Status (4)

Country	Link
EP (1)	EP0525082A1 (fr)
JP (1)	JPH05507302A (fr)
CA (1)	CA2078876A1 (fr)
WO (1)	WO1991016356A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6667397B2 (en) *	2000-08-25	2003-12-23	Eastman Chemical Company	Methods of preparing disaccharide and trisaccharide C6-C12 fatty acid esters with high alpha content and materials therefrom
US7893138B2 (en)	2003-03-14	2011-02-22	Eastman Chemical Company	Low molecular weight carboxyalkylcellulose esters and their use as low viscosity binders and modifiers in coating compositions
GB0516154D0 (en) *	2005-08-05	2005-09-14	Ntnu Technology Transfer As	Carbon membranes
CN104277122B (zh) *	2013-07-11	2016-08-10	南通醋酸纤维有限公司	溶于丙酮的纤维素酯的直接合成方法及其产品
KR101540155B1 (ko) *	2013-10-14	2015-07-28	주식회사 씨티씨	투명성이 향상된 트리아세틸 셀룰로오스 필름 및 이의 제조방법
US11198102B2 (en)	2017-12-04	2021-12-14	Lg Chem, Ltd.	Method for producing composition for forming gas separation membrane active layer, composition for forming gas separation membrane active layer produced by same, method for manufacturing gas separation membrane, and gas separation membrane
CN110642954B (zh) *	2019-09-20	2021-06-29	万华化学集团股份有限公司	一种制备高羟基含量醋酸丁酸纤维素的方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1645915A (en) *	1926-09-23	1927-10-18	Eastman Kodak Co	Process of making cellulose esters of organic acids
US2629716A (en) *	1948-07-07	1953-02-24	Du Pont	Preparation and hydrolysis of esters
JPS6017441B2 (ja) *	1981-07-10	1985-05-02	ダイセル化学工業株式会社	新規なセルロ−スアセテ−トの製造方法

1991
- 1991-04-12 WO PCT/US1991/002557 patent/WO1991016356A1/fr not_active Ceased
- 1991-04-12 CA CA 2078876 patent/CA2078876A1/fr not_active Abandoned
- 1991-04-12 JP JP91508370A patent/JPH05507302A/ja active Pending
- 1991-04-12 EP EP91908621A patent/EP0525082A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
WO1991016356A1 (fr)	1991-10-31
JPH05507302A (ja)	1993-10-21
EP0525082A1 (fr)	1993-02-03

Legal Events

Date	Code	Title	Description
1992-09-22	EEER	Examination request
1994-10-12	FZDE	Dead

Publication	Publication Date	Title
Heinze et al.	2004	4.2 Chemical characteristics of cellulose acetate
Cao et al.	2007	Acetone-soluble cellulose acetates prepared by one-step homogeneous acetylation of cornhusk cellulose in an ionic liquid 1-allyl-3-methylimidazolium chloride (AmimCl)
CA2058967C (fr)	1995-10-03	Composition d'esters de cellulose et procede de fabrication
EP3317304A1 (fr)	2018-05-09	Préparation de polyalpha-1,3-glucane-esters à l'aide d'anhydrides organiques cycliques
KR100394410B1 (ko)	2003-11-14	전분에스테르의제조방법,전분에스테르,및전분에스테르조성물
BR9907637A (pt)	2000-11-14	Processo para produzir um éster de celulose carboxilada a partir de celulose oxidada, butirato de acetato de celulose carboxilada, propionato de acetato de celulose carboxilada, acetato de celulose carboxilada, composição de revestimento, processo para dispersar um pigmento, e, dispersão de pigmento produzida pelo mesmo
EP0074631B2 (fr)	1996-10-16	Procédé pour la préparation d'un sel alcalin de carboxyméthylcellulose
Zhang et al.	2013	Enhanced hydrophobicity and thermal stability of hemicelluloses by butyrylation in [BMIM] Cl ionic liquid
US4480091A (en)	1984-10-30	Process for preparing cellulose sulfate esters
EP0800538B1 (fr)	2001-05-09	Procede de preparation d'esters cellulosiques a l'aide d'un catalyseur de resine d'acide sulfonique
Fox et al.	2011	Synthesis of regioselectively brominated cellulose esters and 6-cyano-6-deoxycellulose esters
CA2059130C (fr)	1999-05-11	Procede d'obtention d'esters de cellulose par utilisation d'acides carboxyliques
Gericke et al.	2020	α-1, 3-Glucan benzoate–A novel polysaccharide derivative
WO1991016356A1 (fr)	1991-10-31	Preparation d'esters de cellulose de faible poids moleculaire
JPH0632801A (ja)	1994-02-08	セルロースエステルの製造方法
CN104140468B (zh)	2017-08-25	一种纤维素混合酯、制备方法及其应用
Shaikh et al.	1998	Thermotropic behavior of cholesterol‐linked polysaccharides
CA2070390C (fr)	1999-03-30	Procede pour la preparation d'esters cellulosiques
US2629716A (en)	1953-02-24	Preparation and hydrolysis of esters
EP0486092A1 (fr)	1992-05-20	Esters gras d'amidon, procédé de préparation et application
US4480090A (en)	1984-10-30	Process for esterification of cellulose using as the catalyst the combination of sulfuric acid, phosphoric acid and a hindered aliphatic alcohol
JP2004035814A (ja)	2004-02-05	セルロースエステル組成物の製造方法
TWI404844B (zh)	2013-08-11	製造醋酸纖維素的方法
JP2004091702A (ja)	2004-03-25	セルロースエステル組成物の製造方法
JPH0931103A (ja)	1997-02-04	高置換度澱粉脂肪酸エステル及びその製造方法