CA1326663C - Fibres tres resistantes de derives de la chitine - Google Patents

Fibres tres resistantes de derives de la chitine

Info

Publication number: CA1326663C
Authority: CA; Canada
Prior art keywords: chitin; degree; fiber; polymer; acetate
Prior art date: 1986-12-16
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.): Expired - Fee Related

Application number

CA000616225A

Other languages

English (en)

Inventor

George Vincent De Lucca

Hollis Smith Kezar, Iii

John Philip O'brien

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.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

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.)

1986-12-16

Filing date

1991-11-06

Publication date

1994-02-01

1986-12-16 Priority claimed from US06/942,442 external-priority patent/US4857403A/en

1991-11-06 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1991-11-06 Priority to CA000616225A priority Critical patent/CA1326663C/fr

1993-06-04 Priority to CA000616643A priority patent/CA1335200C/fr

1994-02-01 Application granted granted Critical

1994-02-01 Publication of CA1326663C publication Critical patent/CA1326663C/fr

2007-12-10 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000835 fiber Substances 0.000 title claims abstract description 41
229920002101 Chitin Polymers 0.000 title abstract description 76
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 36
229920001661 Chitosan Polymers 0.000 claims abstract description 27
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims abstract description 25
238000000034 method Methods 0.000 claims abstract description 19
230000008569 process Effects 0.000 claims abstract description 6
229920000642 polymer Polymers 0.000 claims description 34
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
238000006640 acetylation reaction Methods 0.000 claims description 14
238000006170 formylation reaction Methods 0.000 claims description 13
238000009987 spinning Methods 0.000 claims description 10
230000022244 formylation Effects 0.000 claims description 9
230000021736 acetylation Effects 0.000 claims description 8
238000006467 substitution reaction Methods 0.000 claims description 7
125000003047 N-acetyl group Chemical group 0.000 claims description 4
239000000178 monomer Substances 0.000 claims description 4
ORWKVZNEPHTCQE-UHFFFAOYSA-N acetic formic anhydride Chemical compound CC(=O)OC=O ORWKVZNEPHTCQE-UHFFFAOYSA-N 0.000 claims 1
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
239000007787 solid Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
235000019253 formic acid Nutrition 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
238000002156 mixing Methods 0.000 description 5
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 4
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
230000015271 coagulation Effects 0.000 description 4
238000005345 coagulation Methods 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
238000010586 diagram Methods 0.000 description 3
239000012530 fluid Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000000843 powder Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
241000143060 Americamysis bahia Species 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
238000010306 acid treatment Methods 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
150000002301 glucosamine derivatives Chemical class 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
239000002904 solvent Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
241001290594 Caustis Species 0.000 description 1
229920002284 Cellulose triacetate Polymers 0.000 description 1
241000725101 Clea Species 0.000 description 1
241000543381 Cliftonia monophylla Species 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
241001508687 Mustela erminea Species 0.000 description 1
OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
101150118507 WASL gene Proteins 0.000 description 1
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 compound 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 description 1
150000001243 acetic acids Chemical class 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
238000007605 air drying Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000003518 caustics Substances 0.000 description 1
210000002421 cell wall Anatomy 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000001112 coagulating effect Effects 0.000 description 1
238000007257 deesterification reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
150000004674 formic acids Chemical class 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000001699 lower leg Anatomy 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
229950006780 n-acetylglucosamine Drugs 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000006379 syphilis Diseases 0.000 description 1
229940081330 tena Drugs 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1

Landscapes

Artificial Filaments (AREA)
Materials For Medical Uses (AREA)

CA000616225A 1986-12-16 1991-11-06 Fibres tres resistantes de derives de la chitine Expired - Fee Related CA1326663C (fr)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CA000616225A CA1326663C (fr)	1986-12-16	1991-11-06	Fibres tres resistantes de derives de la chitine
CA000616643A CA1335200C (fr)	1986-12-16	1993-06-04	Fibres hautement resistantes faites de derives de la chitine

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US942,442		1986-12-16
US06/942,442 US4857403A (en)	1986-12-16	1986-12-16	High strength fibers from chitin derivatives
CA000554034A CA1294958C (fr)	1986-12-16	1987-12-10	Fibres haute resistance derivees de la chitine
CA000616225A CA1326663C (fr)	1986-12-16	1991-11-06	Fibres tres resistantes de derives de la chitine

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000554034A Division CA1294958C (fr)	1986-12-16	1987-12-10	Fibres haute resistance derivees de la chitine

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000616643A Division CA1335200C (fr)	1986-12-16	1993-06-04	Fibres hautement resistantes faites de derives de la chitine

Publications (1)

Publication Number	Publication Date
CA1326663C true CA1326663C (fr)	1994-02-01

Family

ID=25671627

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000616225A Expired - Fee Related CA1326663C (fr)	1986-12-16	1991-11-06	Fibres tres resistantes de derives de la chitine

Country Status (1)

Country	Link
CA (1)	CA1326663C (fr)

1991
- 1991-11-06 CA CA000616225A patent/CA1326663C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1998-02-02	MKLA	Lapsed

Publication	Publication Date	Title
US4857403A (en)	1989-08-15	High strength fibers from chitin derivatives
US4861527A (en)	1989-08-29	High strength chitosan fibers and fabrics thereof
US5021207A (en)	1991-06-04	High strength fibers from chitin derivatives
US9175423B2 (en)	2015-11-03	Composition for preparing polysaccharide fibers
US9540747B2 (en)	2017-01-10	Composition for preparing polysaccharide fibers
EP2764145B1 (fr)	2018-05-23	Nouvelle composition pour la préparation de fibres de polysaccharide
KR20160079798A (ko)	2016-07-06	다당류 섬유를 제조하기 위한 조성물
US4833238A (en)	1989-05-23	High strength fibers from chitin derivatives
CA1335200C (fr)	1995-04-11	Fibres hautement resistantes faites de derives de la chitine
EP1167391B1 (fr)	2007-07-04	Triacetate de cellulose et procede de production associe
NZ235730A (en)	1991-03-26	Chitin acetate fibre and its production
JPWO2001070820A1 (ja)	2003-07-08	セルロースエステルの製造方法
CN87108135A (zh)	1988-06-29	用几丁质衍生物制造的高强度纤维
Zhuang et al.	2008	Preparation and properties of 2-(2-aminoethoxy) ethyl chitosan/cellulose fiber using N-methylmorpholine-N-oxide process
JPH0525289A (ja)	1993-02-02	キチン成形体の製造法
Agboh	1986	The production of fibres from chitin
PL187224B1 (pl)	2004-06-30	Sposób wytwarzania włókien z estrów chityny
Duarte et al.	1991	Homogeneous guluronic and mannuronic acid blocks in the alginate of the brown seaweed Laminaria brasiliensis