DE540374T1 - Verfahren zur Herstellung von wasserlöslichen und/oder wasserdispergierbaren Polyestern und die Verwendung dieser Polyester zum Schlichten von Textilgarnen. - Google Patents
Verfahren zur Herstellung von wasserlöslichen und/oder wasserdispergierbaren Polyestern und die Verwendung dieser Polyester zum Schlichten von Textilgarnen.Info
- Publication number
- DE540374T1 DE540374T1 DE0540374T DE92402292T DE540374T1 DE 540374 T1 DE540374 T1 DE 540374T1 DE 0540374 T DE0540374 T DE 0540374T DE 92402292 T DE92402292 T DE 92402292T DE 540374 T1 DE540374 T1 DE 540374T1
- Authority
- DE
- Germany
- Prior art keywords
- process according
- ethylene glycol
- water
- reaction
- dimethyl ester
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract 17
- 238000004513 sizing Methods 0.000 title claims abstract 3
- 239000004753 textile Substances 0.000 title claims abstract 3
- 229920000728 polyester Polymers 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract 40
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract 10
- 238000005886 esterification reaction Methods 0.000 claims abstract 7
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims abstract 6
- 238000006068 polycondensation reaction Methods 0.000 claims abstract 6
- -1 polyoxyethylene Polymers 0.000 claims abstract 6
- 238000005809 transesterification reaction Methods 0.000 claims abstract 6
- 229920001634 Copolyester Polymers 0.000 claims abstract 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims abstract 3
- 238000006243 chemical reaction Methods 0.000 claims abstract 3
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 claims abstract 3
- 238000002360 preparation method Methods 0.000 claims abstract 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims abstract 3
- 239000003054 catalyst Substances 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 229910052751 metal Inorganic materials 0.000 claims 4
- 239000002184 metal Substances 0.000 claims 4
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims 2
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 claims 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims 2
- 229960005147 calcium acetate Drugs 0.000 claims 2
- 235000011092 calcium acetate Nutrition 0.000 claims 2
- 239000001639 calcium acetate Substances 0.000 claims 2
- AOWKSNWVBZGMTJ-UHFFFAOYSA-N calcium titanate Chemical compound [Ca+2].[O-][Ti]([O-])=O AOWKSNWVBZGMTJ-UHFFFAOYSA-N 0.000 claims 2
- 150000007942 carboxylates Chemical class 0.000 claims 2
- 229940011182 cobalt acetate Drugs 0.000 claims 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims 2
- 230000032050 esterification Effects 0.000 claims 2
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical compound O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 claims 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- 229940071125 manganese acetate Drugs 0.000 claims 2
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- 239000010936 titanium Substances 0.000 claims 2
- 229910052719 titanium Inorganic materials 0.000 claims 2
- 239000004246 zinc acetate Substances 0.000 claims 2
- 229960000314 zinc acetate Drugs 0.000 claims 2
- 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 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 241000158147 Sator Species 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000005690 diesters Chemical class 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- 229940119177 germanium dioxide Drugs 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 125000001174 sulfone group Chemical group 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000003827 glycol group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/507—Polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6886—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- 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
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Treatment Of Fibers During Manufacturing Processes (AREA)
Claims (15)
1. Verfahren zur Herstellung eines wasserlöslichen und/oder wasserdispergierbaren
Copolyesters, umfassend Struktureinheiten Terephthalat, Isophthalat, SuIfoaryldicarboxylat, Ethylenglycol
und Polyoxyethylenglycol, dadurch gekennzeichnet, daß es die nachstehenden, aufeinanderfolgenden Stufen umfaßt:
- eine Reaktion zur Umesterung (interechange) zwischen einerseits Terephthalsäure-dimethylester und Sulfoaryldicarbonsäure-dimethylester
und andererseits Ethylenglycol;
- eine Reaktion zur direkten Veresterung zwischen Isophthalsäure und einer neuen Menge von Ethylenglycol;
eine Reaktion zur Polykondensation.
2. Verfahren zur Herstellung eines wasserlöslichen und/oder wasserdispergierbaren
Copolyesters, umfassend Struktureinheiten Terephthalat, Isophthalat, SuIfoaryldicarboxylat, Ethylenglycol
und Polyoxyethylenglycol, dadurch gekennzeichnet, daß es die nachstehenden, aufeinanderfolgenden Stufen umfaßt:
eine Reaktion zur Umesterung (interechange) zwischen einerseits Terephthalsäure-dimethylester und Sulfoaryldicarbonsäure-dimethylester
und andererseits Ethylenglycol, wobei das molare Verhältnis Ethylenglycol/Diester zwischen
1,8 und 3,5 und vorzugsweise zwischen 2,0 und 3,0 beträgt; eine Reaktion zur direkten Veresterung zwischen Isophthalsäure
und einer neuen Menge von Ethylenglycol, wobei das molare Verhältnis Ethylenglycol/Isophthalsäure zwischen
1,8 und 3,0 und vorzugsweise zwischen 2,0 und 2,8 beträgt;
- eine Reaktion zur Polykondensation.
3. Verfahren nach einem der Ansprüche 1 oder 2, dadurch gekennzeichnet,
daß der Sulfoaryldicarbonsäure-dimethylester ausgewählt
wird unter den Verbindungen der Formel (I)
^COOCH3
M-O3S-Qn
COOCH3
in der
- M ein Wasserstoffatom oder vorzugsweise ein Atom von Natrium,
Kalium oder Lithium darstellt,
- Q einen Rest Phenyl oder eine Kombination von mehreren ortho- oder perikondensierten Resten Phenyl oder mehreren
Resten Phenyl bedeutet, die untereinander durch inerte Gruppen verbunden sind wie eine einfache Valenzbindung,
ein Rest Alkylen, eine Gruppe Ether, Gruppe Keton oder Gruppe SuIfön.
4. Verfahren nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet,
daß der Sulfoaryldicarbonsäure-dimethylester Natrium-5-oxysulfonyl-isophthalsäure-dimethylester
ist.
5. Verfahren nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet,
daß die Temperatur, bei der die Reaktion der Umesterung durchgeführt wird, gleich oder höher 130 0C beträgt und vorzugsweise
zwischen 140 0C und 250 0C liegt.
6. Verfahren nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet,
daß die Reaktion der Umesterung in Anwesenheit eines Umesterungskatalysators durchgeführt wird, im allgemeinen ausgewählt
unter den Metallderivaten wie den Metallcarboxylaten, beispielsweise Manganacetat, Zinkacetat, Cobaltacetat oder Calciumacetat;
den organischen Titanaten wie Butyltitanat oder 2,2',2"-Nitrilo-triethyltitanat
(oder Titan-aminotriethanolat) und den mineralischen Titanaten wie Calciumtitanat.
7. Verfahren nach Anspruch 6, dadurch gekennzeichnet, daß die
Menge des Katalysators mindestens 0,005 Gew.-% pro Gesamtgewicht der Reaktanden und vorzugsweise 0,01 Gew.-% bis 2 Gew.-% pro Gewicht
darstellt.
8. Verfahren nach einem der Ansprüche 1 oder 2, dadurch gekennzeichnet,
daß die beschriebene Reaktion der Veresterung bei einer Temperatur zwischen 210 0C und 280 0C und vorzugsweise zwischen
220 0C und 260 0C realisiert wird.
9. Verfahren nach Anspruch 8, dadurch gekennzeichnet, daß die direkte Reaktion der Veresterung in Anwesenheit eines Kataly-
sators realisiert wird, ausgewählt unter den Metallderivaten wie
den Metallcarboxylaten, beispielsweise Manganacetat, Zinkacetat, Cobaltacetat oder Calciumacetat; den organischen Titanaten wie
Butyltitanat oder 2,2',2"-Nitrilo-triethyltitanat (oder Titanaminotriethanolat)
und den mineralischen Titanaten wie Calciumtitanat.
10. Verfahren nach Anspruch 9, dadurch gekennzeichnet, daß die
Menge des Katalysators für die direkte Veresterung mindestens 0,005 Gew.-%, bezogen auf das Gewicht von Isophthalsäure und
Ethylenglycol, die bei der genannten Reaktion der direkten Veresterung
eingesetzt werden, und vorzugsweise 0,01 Gew.-% bis 2 Gew.-% pro Gewicht darstellt.
11. Verfahren nach einem der Ansprüche 1 oder 2, dadurch gekennzeichnet,
daß die Reaktion der Polykondensation bei einer Temperatur zwischen 230 0C und 280 0C und vorzugsweise zwischen 240 °.C
und 260 0C realisiert wird.
12. Verfahren nach Anspruch 11, dadurch gekennzeichnet, daß die
Reaktion der Polykondensation in Anwesenheit eines Katalysators realisiert wird, ausgewählt unter Antimontrioxid und Germaniumdioxid.
13. Verfahren nach einem der Ansprüche 11 oder 12, dadurch gekennzeichnet,
daß die Reaktion der Polykondensation unter einem niedrigeren Druck als dem atmosphärischen Druck durchgeführt
wird.
14. Verfahren zum Schlichten von Ketten aus Textilgarnen, dadurch gekennzeichnet, daß es darin besteht, die gemäß einem der Ansprüche
1 bis 13 hergestellten wasserlöslichen und/oder wasserdispergierbaren Copolyester im wäßrigen Medium anzuwenden.
15. Verfahren nach Anspruch 14, dadurch gekennzeichnet, daß es
darin besteht, die Garne in ein wäßriges Bad einzutauchen, das den Copolyester in der gewünschten Konzentration und der gewünschten
Temperatur enthält, anschließend die genannten Garne
mittels Passage zwischen Walzen abzuquetschen und schließlich die geschlichteten Garne in einer wannen Kammer zu trocknen.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9113595A FR2682956B1 (fr) | 1991-10-29 | 1991-10-29 | Procede de preparation de polyesters hydrosolubles et/ou hydrodispersables et utilisation de ces polyesters pour l'encollage de fils textiles. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE540374T1 true DE540374T1 (de) | 1998-11-19 |
Family
ID=9418600
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69230460T Expired - Lifetime DE69230460T2 (de) | 1991-10-29 | 1992-08-17 | Verfahren zur Herstellung von wasserlöslichen und/oder wasserdispergierbaren Polyestern und die Verwendung dieser Polyester zum Schlichten von Textilgarnen |
| DE0540374T Pending DE540374T1 (de) | 1991-10-29 | 1992-08-17 | Verfahren zur Herstellung von wasserlöslichen und/oder wasserdispergierbaren Polyestern und die Verwendung dieser Polyester zum Schlichten von Textilgarnen. |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69230460T Expired - Lifetime DE69230460T2 (de) | 1991-10-29 | 1992-08-17 | Verfahren zur Herstellung von wasserlöslichen und/oder wasserdispergierbaren Polyestern und die Verwendung dieser Polyester zum Schlichten von Textilgarnen |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5290631A (de) |
| EP (1) | EP0540374B1 (de) |
| JP (1) | JP2573543B2 (de) |
| KR (1) | KR970002080B1 (de) |
| CN (1) | CN1033392C (de) |
| AT (1) | ATE187975T1 (de) |
| AU (1) | AU655078B2 (de) |
| CA (1) | CA2080883C (de) |
| DE (2) | DE69230460T2 (de) |
| ES (1) | ES2118671T3 (de) |
| FR (1) | FR2682956B1 (de) |
| RU (1) | RU2102405C1 (de) |
| TW (1) | TW227025B (de) |
Families Citing this family (104)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2720400B1 (fr) | 1994-05-30 | 1996-06-28 | Rhone Poulenc Chimie | Nouveaux polyesters sulfones et leur utilisation comme agent anti-salissure dans les compositions détergentes, de rinçage, d'adoucissage et de traitement des textiles. |
| FR2722804B1 (fr) * | 1994-07-22 | 1996-09-13 | Rhone Poulenc Chimie | Composition latex pour l'encollage de fils ou de fibres textiles et procede d'encollage |
| US6162890A (en) * | 1994-10-24 | 2000-12-19 | Eastman Chemical Company | Water-dispersible block copolyesters useful as low-odor adhesive raw materials |
| DE69532875T2 (de) * | 1994-10-24 | 2004-08-19 | Eastman Chemical Co., Kingsport | Wasserdispergierbare Blockcopolyester |
| US5646237A (en) * | 1995-08-15 | 1997-07-08 | Eastman Chemical Company | Water-dispersible copolyester-ether compositions |
| KR100369847B1 (ko) * | 1995-12-29 | 2003-03-26 | 에스케이케미칼주식회사 | 수분산성 코폴리에스테르 수지조성물 |
| KR970062170A (ko) * | 1995-12-29 | 1997-09-12 | 김준웅 | 폴리에스테르 호제조성물 |
| US5820982A (en) * | 1996-12-03 | 1998-10-13 | Seydel Companies, Inc. | Sulfoaryl modified water-soluble or water-dispersible resins from polyethylene terephthalate or terephthalates |
| FR2766200B1 (fr) | 1997-07-17 | 1999-09-24 | Toray Plastics Europ Sa | Films polyester composites metallises a proprietes barriere |
| US6020420A (en) * | 1999-03-10 | 2000-02-01 | Eastman Chemical Company | Water-dispersible polyesters |
| US6171685B1 (en) | 1999-11-26 | 2001-01-09 | Eastman Chemical Company | Water-dispersible films and fibers based on sulfopolyesters |
| US7030181B2 (en) * | 2001-04-11 | 2006-04-18 | Eastman Chemical Company | Films prepared from plasticized polyesters |
| US6984675B2 (en) * | 2001-11-28 | 2006-01-10 | Resolution Specialty Materials Llc | Formaldehyde-free binder compositions for simultaneous warp sizing and coloration of filament yarns |
| US20030124367A1 (en) * | 2001-12-06 | 2003-07-03 | George Scott Ellery | Antistatic polyester-polyethylene glycol compositions |
| US7625994B2 (en) | 2002-07-30 | 2009-12-01 | E.I. Du Pont De Nemours And Company | Sulfonated aliphatic-aromatic copolyetheresters |
| US20040024102A1 (en) * | 2002-07-30 | 2004-02-05 | Hayes Richard Allen | Sulfonated aliphatic-aromatic polyetherester films, coatings, and laminates |
| US6896966B2 (en) * | 2002-11-22 | 2005-05-24 | Eastman Chemical Company | Articles of manufacture incorporating polyester/polycarbonate blends |
| US7118799B2 (en) * | 2002-11-22 | 2006-10-10 | Eastman Chemical Company | Thermoplastic article having a decorative material embedded therein |
| US7285587B2 (en) * | 2002-12-20 | 2007-10-23 | Eastman Chemical Company | Flame retardant polyester compositions for calendering |
| US7144600B2 (en) * | 2003-02-18 | 2006-12-05 | Milliken & Company | Wax-free lubricant for use in sizing yarns, methods using same and fabrics produced therefrom |
| US7579047B2 (en) * | 2003-05-20 | 2009-08-25 | Milliken & Company | Lubricant and soil release finish for textured yarns, methods using same and fabrics produced therefrom |
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| GB1238850A (de) * | 1967-12-05 | 1971-07-14 | ||
| US3546008A (en) * | 1968-01-03 | 1970-12-08 | Eastman Kodak Co | Sizing compositions and fibrous articles sized therewith |
| JPS48103883A (de) * | 1972-04-13 | 1973-12-26 | ||
| EP0029620A1 (de) * | 1979-11-19 | 1981-06-03 | Agfa-Gevaert N.V. | Wässrige Copolyester-Dispersionen, die für die Substrierung eines Polyesterfilms geeignet sind, der substrierte Polyesterfilm und photographische Materialien, die einen substrierten Polyesterträger enthalten |
| JPS5763325A (en) * | 1980-10-02 | 1982-04-16 | Toyobo Co Ltd | Copolyester |
| JPS592285A (ja) * | 1982-06-28 | 1984-01-07 | Fujitsu Ltd | 磁気バブルメモリの駆動方式 |
| JPS59144611A (ja) * | 1983-02-01 | 1984-08-18 | Teijin Ltd | ポリエステル繊維 |
| JPS6157618A (ja) * | 1984-08-29 | 1986-03-24 | Teijin Ltd | 改質ポリエステルの製造方法 |
| JPS6289725A (ja) * | 1985-10-15 | 1987-04-24 | Teijin Ltd | 改質ポリエステルの製造方法 |
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| FR2608506B1 (fr) * | 1986-12-23 | 1989-03-31 | Rhone Poulenc Films | Procede d'obtention de films polyester composites epais a adherence amelioree et nouveaux films composites |
| FR2609665B1 (fr) * | 1987-01-21 | 1989-04-14 | Rhone Poulenc Films | Procede d'obtention de films polyester a revetement de polychlorure de vinylidene et nouveaux films composites ainsi obtenus |
| JP2530649B2 (ja) * | 1987-04-15 | 1996-09-04 | 東レ株式会社 | 改質ポリエステルの製造法 |
| FR2640983B1 (de) * | 1988-12-28 | 1992-09-25 | Rhone Poulenc Films |
-
1991
- 1991-10-29 FR FR9113595A patent/FR2682956B1/fr not_active Expired - Lifetime
-
1992
- 1992-08-17 ES ES92402292T patent/ES2118671T3/es not_active Expired - Lifetime
- 1992-08-17 DE DE69230460T patent/DE69230460T2/de not_active Expired - Lifetime
- 1992-08-17 DE DE0540374T patent/DE540374T1/de active Pending
- 1992-08-17 AT AT92402292T patent/ATE187975T1/de not_active IP Right Cessation
- 1992-08-17 EP EP92402292A patent/EP0540374B1/de not_active Expired - Lifetime
- 1992-09-30 AU AU26131/92A patent/AU655078B2/en not_active Ceased
- 1992-10-15 CN CN92111622A patent/CN1033392C/zh not_active Expired - Fee Related
- 1992-10-19 CA CA002080883A patent/CA2080883C/fr not_active Expired - Lifetime
- 1992-10-19 TW TW081108293A patent/TW227025B/zh active
- 1992-10-22 JP JP4308066A patent/JP2573543B2/ja not_active Expired - Lifetime
- 1992-10-28 KR KR1019920019958A patent/KR970002080B1/ko not_active IP Right Cessation
- 1992-10-28 RU RU92004361A patent/RU2102405C1/ru active
- 1992-10-29 US US07/968,306 patent/US5290631A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2080883C (fr) | 1999-01-05 |
| ATE187975T1 (de) | 2000-01-15 |
| EP0540374B1 (de) | 1999-12-22 |
| US5290631A (en) | 1994-03-01 |
| DE69230460D1 (de) | 2000-01-27 |
| JP2573543B2 (ja) | 1997-01-22 |
| TW227025B (de) | 1994-07-21 |
| CN1033392C (zh) | 1996-11-27 |
| RU2102405C1 (ru) | 1998-01-20 |
| FR2682956A1 (fr) | 1993-04-30 |
| FR2682956B1 (fr) | 1994-01-07 |
| AU2613192A (en) | 1993-05-06 |
| KR970002080B1 (ko) | 1997-02-22 |
| ES2118671T1 (es) | 1998-10-01 |
| EP0540374A1 (de) | 1993-05-05 |
| ES2118671T3 (es) | 2000-04-01 |
| CN1072691A (zh) | 1993-06-02 |
| AU655078B2 (en) | 1994-12-01 |
| DE69230460T2 (de) | 2000-08-03 |
| JPH05295097A (ja) | 1993-11-09 |
| KR930008015A (ko) | 1993-05-20 |
| CA2080883A1 (fr) | 1993-04-30 |
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