DE1301566B - Process for the production of hydrolysis-resistant polyurethane elastomers - Google Patents
Process for the production of hydrolysis-resistant polyurethane elastomersInfo
- Publication number
- DE1301566B DE1301566B DE1966C0040839 DEC0040839A DE1301566B DE 1301566 B DE1301566 B DE 1301566B DE 1966C0040839 DE1966C0040839 DE 1966C0040839 DE C0040839 A DEC0040839 A DE C0040839A DE 1301566 B DE1301566 B DE 1301566B
- Authority
- DE
- Germany
- Prior art keywords
- hydroxyl
- polyester
- hydrolysis
- polyethers
- polyesters
- 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
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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
- C08G18/4247—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids
- C08G18/4252—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids derived from polyols containing polyether groups and polycarboxylic acids
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
haftet jedoch als Nachteil die leichte Verseifbarkeit io lisch reagierende Substanzen bereits in kurzer Zeit dieser Ester und damit die Unbeständigkeit in tro- zerstörend auf Polyurethane herkömmlichen Aufbaus pischem Klima an. Polyätherurethane besitzen eine wesentlich bessereHydrolysenbeständigkeit, dochkann man ausreichende physikalische Daten nur mit Äthern vom Typus des Polytetramethylenglykols erhal- 15 tenjWährenddieauadenleichterzugänglichenPoIypropylenglykolen hergestellten Elastomeren in ihrem physikalischen Niveau nicht in jeder Hinsicht befriedigen. Die Hydrolysenbeständigkeit von Polyesterurethanen kann teils durch die Beimischung von Poly- 20 carbodiimiden, teils auch durch Verwendung von Hexandioladipinsäurepolyestern verbessert werden, doch lassen sich auf diesem Wege keine Verbesserungen erzielen, die den Polyätherpolyurethanen hinsichtlich dieser Eigenschaft vergleichbare Resultate 25 anwendbar. Die genannten Polypropylenglykole liefern würden. Eine Ausnahme hiervon bilden Poly- können auch ganz oder teilweise durch andere Polyurethane, die auf der Basis von Phthalsäurehexandiol- bzw. Terephthalsäurehexandiolpolyester aufgebaut sind. Diese besitzen auch nach längerer Lagerung inhowever, the disadvantage is the easy saponifiability of substances that react io cally in a short time this ester and with it the instability in the dry-destructive structure conventionally based on polyurethanes pical climate. Polyether urethanes have much better resistance to hydrolysis, but can Sufficient physical data can only be obtained with ethers of the polytetramethylene glycol type tenjduring the loading, more easily accessible polypropylene glycols produced elastomers are not satisfactory in all respects in their physical level. The hydrolysis resistance of polyester urethanes can partly be achieved by adding poly-20 carbodiimides, partly also by using hexanedioladipic acid polyesters, but no improvements can be achieved in this way, which the polyether polyurethanes with respect to results comparable to this property can be applied. The polypropylene glycols mentioned would deliver. An exception to this are poly- can also be completely or partially replaced by other polyurethanes, which are based on phthalic acid hexanediol or terephthalic acid hexanediol polyester are. Even after prolonged storage in
wirken. Auch für chemisch hoch beanspruchte Laufrollen in galvanischen Anlagen lassen sich nunmehr wirtschaftlich Polyurethane erfindungsgemäßen Aufbaus einsetzen. Durch die Erfindung wird aber nicht nur die Hydrolysenfestigkeit heraufgesetzt, auch andere physikalische Eigenschaften werden im Vergleich zu herkömmlichen Polyurethanen verbessert, insbesondere der Abrieb und die Weiterreißfestigkeit. An Stelle der genannten Gemische aus Polyestern und Polyäthern oder mit diesen Gemischen zusammen sind auch mit Polypropylenglykol verätherte Mischester der Phthal- bzw. Terephthalsäure mit den eingangs genannten Diolen mit ähnlichem Erfolgworks. Also for chemically highly stressed rollers in electroplating systems can now economically use polyurethanes according to the invention. The invention does not only the resistance to hydrolysis is increased; other physical properties are also compared Improved compared to conventional polyurethanes, in particular the abrasion and tear resistance. Instead of the aforementioned mixtures of polyesters and polyethers or together with these mixtures are also mixed esters of phthalic or terephthalic acid etherified with polypropylene glycol with the initially mentioned diols with similar success
äther, wie z. B. das Tetramethylenglykol oder entsprechende Derivate des polymerisierten Oxacyclobutans, ersetzt werden. Zweckmäßig werden Propy-ether, such as B. tetramethylene glycol or corresponding derivatives of polymerized oxacyclobutane, be replaced. Propy-
Wasser von 100° C noch gute physikalische Werte, 30 Ienglykole mit einem Molekulargewicht zwischen 250Water at 100 ° C still has good physical values, 30 Iene glycols with a molecular weight between 250
jedoch liegt ihre Einfriertemperatur bei Raumtemperaturen bzw. darüber, so daß ihre Anwendung nur für weniger Sonderfälle, namentlich bei höheren Temperaturen, möglich ist.however, their freezing temperature is at room temperatures or above, so that their use only is possible for fewer special cases, in particular at higher temperatures.
Überraschenderweise wurde nun gefunden, daß Polyurethanelastomere mit ausgezeichneter Hydrolysenfestigkeit und sonst guten physikalischen Eigenschaften hergestellt werden können, wenn als hydroxylgruppenhaltige Komponente des Reaktionsund 5000 und einer OH-Zahl zwischen 25 und 250 verwendet.Surprisingly, it has now been found that polyurethane elastomers have excellent resistance to hydrolysis and otherwise good physical properties can be produced when called hydroxyl-containing Component of the reaction and 5000 and an OH number between 25 and 250 used.
Zusammen mit oder an Stelle der Phthal- oder Terephthalsäure können auch Dicarbonsäuren verwendet werden, die am a-C-Atom mindestens einen Substituenten R enthalten — hierbei kann R ein Methyl-, Äthyl-, Butyl- oder Phenylrest sein. Als Polyester können weiterhin solche Verwendung finden, die z. B. durch Polymerisation von Capro-Dicarboxylic acids can also be used together with or instead of phthalic or terephthalic acid which contain at least one substituent R on the a-C atom - here R can be Be methyl, ethyl, butyl or phenyl radical. Such uses can continue to be used as polyester find the z. B. by polymerizing Capro-
gemisches ein Gemisch von hydroxylgruppenhaltigen 40 lactonen und/oder Laurinlactonen hergestellt worden Polyestern und Polyäthern zur Anwendung gelangt sind, vorzugsweise ebenfalls am ct-C-Atom substituiert, in der vorstehend genannten Weise. Wie die Ausführungsbeispiele zeigen,mixture a mixture of hydroxyl-containing lactones and / or laurolactones has been produced Polyesters and polyethers have been used, preferably also substituted on the ct-C atom, in the aforementioned manner. As the examples show,
und das in dieser Weise abgeänderte Reaktionsgemisch, das weiter Diisocyanate und Diole als wesentliche Komponenten enthält, in gewohnter Weise zur Reaktion gebracht wird.and the reaction mixture modified in this way, which furthermore contains diisocyanates and diols as contains essential components, is made to react in the usual way.
Das beanspruchte Verfahren zur Herstellung von hydrolysenbeständigen Polyurethanelastomeren durch Umsetzen von hydroxylgruppenhaltigen Polyestern oder Polyäthern als hydroxylgruppenhaltigen Komsind zurThe claimed process for the production of hydrolysis-resistant polyurethane elastomers by Reaction of hydroxyl-containing polyesters or polyethers as hydroxyl-containing grains are to the
Herstellung wertvoller Polyurethanelastomerer PoIyäther und Polyester in weiten Grenzen mischbar. Die günstigsten Eigenschaften werden erhalten, wenn das Mischungsverhältnis Polyäther zu Polyester im Bereich zwischen 2 : 8 und 8 : 2 liegt. Die Beispiele 1 und 4 zeigen die Herstellung jeManufacture of valuable polyurethane elastomer polyethers and polyester can be mixed within wide limits. The most favorable properties are obtained when that Mixing ratio of polyether to polyester is in the range between 2: 8 and 8: 2. Examples 1 and 4 each show the preparation
ponenten mit Dusocyanaten und Diolen ist dadurch 50 eines Polyester- bzw. Polyätherurethans im Vergleich gekennzeichnet, daß als hydroxylgruppenhaltige zu Mischpolyurethanen gemäß Erfindung nach Beispielen 2 und 3. Die Eigenschaften der erhaltenen Polyurethane sind in der Tabelle zusammengefaßt.components with diisocyanates and diols is therefore 50 in comparison to a polyester or polyether urethane characterized in that as hydroxyl-containing to mixed polyurethanes according to the invention according to examples 2 and 3. The properties of the polyurethanes obtained are summarized in the table.
Komponenten des Reaktionsgemisches Gemische von Polyäthern mit hydroxylgruppenhaltigen Polyestern oder Äthergruppierungen enthaltende hydroxylgruppenhaltige Polyester eingesetzt werden.Components of the reaction mixture Mixtures of polyethers with hydroxyl-containing polyesters or hydroxyl-containing polyesters containing ether groups are used.
Als besonders vorteilhaft zur Herstellung von Polyurethanelastomeren mit hervorstechenden Eigenschaften haben sich die Ester der Phthal- bzw. Terephthalsäure oder α-substituierten DicarbonsäurenAs particularly advantageous for the production of polyurethane elastomers The esters of phthalic and terephthalic acid have outstanding properties or α-substituted dicarboxylic acids
1000 g eines Polyesters aus Terephthalsäure und Hexandiol vom Molekulargewicht 2000 und der Hydroxylzahl 56 werden aufgeschmolzen und bei 140° C mit 850 g Diphenylmethandiisocyanat zur1000 g of a polyester made from terephthalic acid and hexanediol with a molecular weight of 2000 and a hydroxyl number of 56 are melted and at 140 ° C. with 850 g of diphenylmethane diisocyanate
mit Hexandiol, Neopentylglykol oder Dimethylol- 60 Reaktion gebracht. Die erhaltene klare Schmelze wirdbrought with hexanediol, neopentyl glycol or dimethylol 60 reaction. The clear melt obtained is
cyklohexan bzw. «-substituierten Polyketenen erwiesen. Werden diese Polyester mit Polypropylenglykolen im Gemisch verwendet, so wird es möglich, Elastomere mit Eigenschaften herzustellen, die bei Polyurethanelastomeren nicht zu erreichen waren.Cyclohexane or -substituted polycetenes proved. If these polyesters are used in a mixture with polypropylene glycols, it is possible to To produce elastomers with properties that could not be achieved with polyurethane elastomers.
Aus solchen Polyester-Polyäther-Gemischen hergestellte Polyurethanelastomere zeigen eine Hydrolysenfestigkeit, wie sie bisher nicht erreichbar war.Manufactured from such polyester-polyether mixtures Polyurethane elastomers show a resistance to hydrolysis that was previously unattainable.
nach 5 Minuten mit 240 g 1,4-Butandiol umgesetzt und in Form von flachen Platten ausgegossen. Nach dem Erstarren des Materials erwärmt man noch etwa 20 Minuten auf einer Heizplatte mit 125° C, läßt anschließend erkalten und granuliert am nächsten Tag in einer Schneidmühle. Das Granulat ist lagerfähig und läßt sich in bekannter Weise auf Schnecken-Spritzgußautomaten verarbeiten.reacted after 5 minutes with 240 g of 1,4-butanediol and poured out in the form of flat plates. After the material has solidified, it is still heated for about 20 minutes on a hot plate at 125 ° C, then allowed to cool and granulate the next Day in a granulator. The granulate can be stored and can be processed in a known manner on automatic screw injection molding machines.
600 g Terephthalsäure-Hexandiolester, dem Beispiel 1 entsprechend, werden mit 400 g Polypropylenglykol vom Molekulargewicht 2000 und der Hydroxylzahl 56 bei 140° C vermischt und mit 850 g Diphenylmethandiisocyanat zur Reaktion gebracht. Nach 2 Stunden, während derer das Material auf 1100C gehalten wird, werden 240 g 1,4-Butandiol hinzugesetzt und die gesamte Masse nach dem Homogenisieren in Form von flachen Platten ausgegossen, worauf das Abkühlen und Granulieren wie im Beispiel 1 erfolgt.600 g of hexanediol terephthalate, corresponding to Example 1, are mixed with 400 g of polypropylene glycol with a molecular weight of 2000 and a hydroxyl number of 56 at 140 ° C. and reacted with 850 g of diphenylmethane diisocyanate. After 2 hours, during which the material is kept at 110 ° C., 240 g of 1,4-butanediol are added and, after homogenization, the entire mass is poured out in the form of flat plates, followed by cooling and granulation as in Example 1.
300 g Terephthalsäure-Hexandiolester, dem Beispiel 1 entsprechend, und 700 g Polypropylenglykol vom Molekulargewicht 2000, dem Beispiel 2 entsprechend, werden bei 140° C gemischt und mit 850 g Diphenylmethandiisocyanat zur Reaktion gebracht. Die resultierende Schmelze wird 2 Stunden lang auf 110° C gehalten und dann mit 240 g 1,4-Butandiol verrührt und anschließend in Form von flachen Platten ausgegossen. Nach dem Erstarren des Materials wird noch etwa 20 Minuten bei 1100C nachgeheizt und anschließend das Material nach dem Erkalten granuliert. Die Weiterverarbeitung kann auf Spritzgußmaschinen in gewohnter Weise erfolgen.300 g of hexanediol terephthalate, corresponding to Example 1, and 700 g of polypropylene glycol with a molecular weight of 2000, corresponding to Example 2, are mixed at 140 ° C. and reacted with 850 g of diphenylmethane diisocyanate. The resulting melt is kept at 110 ° C. for 2 hours and then stirred with 240 g of 1,4-butanediol and then poured out in the form of flat plates. After the material has solidified, heating is continued for about 20 minutes at 110 ° C. and then the material is granulated after cooling. Further processing can take place in the usual way on injection molding machines.
1000 g eines Polypropylenglykols vom Molekulargewicht 2000 und der Hydroxylzahl 56 werden bei 140° C mit 850 g Diphenylmethandiisocyanat zur Reaktion gebracht. Die resultierende Schmelze wird1000 g of a polypropylene glycol with a molecular weight of 2000 and a hydroxyl number of 56 are at 140 ° C brought to reaction with 850 g of diphenylmethane diisocyanate. The resulting melt will
ίο 2 Stunden lang bei 110° C gehalten und danach mit 240 g 1,4-Butandiol verrührt. Man gießt das Reaktionsgemisch zu flachen Platten aus, läßt erstarren, heizt 20 Minuten bei 110° C nach und granuliert das Material nach etwa 24stündigem Abkühlen. Das erhaltene Granulat kann anschließend in gewohnter Weise auf Spritzgußmaschinen weiterverarbeitet werden.ίο Maintained at 110 ° C for 2 hours and then with 240 g of 1,4-butanediol were stirred. The reaction mixture is poured into flat plates, allowed to solidify, reheat for 20 minutes at 110 ° C and granulate the material after cooling for about 24 hours. That The granulate obtained can then be further processed in the usual way on injection molding machines will.
Aus den nach den Beispielen 1 bis 4 hergestellten Elastomeren wurden in Spritzguß Prüfplatten in und 6 mm Dicke hergestellt. Aus den 3-mm-Prüfplatten wurden Stäbe gestanzt und daran die Zerreißfestigkeit, die Bruchdehnung und die Weiterreißfestigkeit bestimmt, während an den 6 mm dicken Prüfkörpern Abrieb, Stoßelastizität, Shorehärte usw.From the elastomers produced according to Examples 1 to 4, test plates in and 6 mm thick. Rods were punched out of the 3 mm test plates and the tensile strength, the elongation at break and the tear strength determined, while at the 6 mm thick Test specimens abrasion, impact elasticity, Shore hardness, etc.
ermittelt wurden.were determined.
Elastomeren nach BeispielElastomers according to the example
1 2 I 1 2 I.
Terephthalsäure-Hexandiolpolyester Terephthalic acid hexanediol polyester
Polypropylenglykol Polypropylene glycol
Festigkeit (DIN 53504) Strength (DIN 53504)
Dehnung (DIN 53504) Elongation (DIN 53504)
Abrieb (DIN 53516) Abrasion (DIN 53516)
Elastizität (DIN 53512) Elasticity (DIN 53512)
Shore-Härte A (DIN 53505) Shore hardness A (DIN 53505)
Shore-Härte D (DIN 53505) Shore hardness D (DIN 53505)
Weiterreißfestigkeit (DIN 53507) Tear strength (DIN 53507)
Festigkeit nach Wasserlagerung in Tagen bei 80° C (DIN 53521):Strength after water storage in days at 80 ° C (DIN 53521):
7 Tage 7 days
14 Tage 14 days
21 Tage 21 days
bei 100° C:at 100 ° C:
7 Tage 7 days
14 Tage 14 days
21 Tage 21 days
Lagerung im Fett-Wasser-Gemisch bei 80° C:Storage in a fat-water mixture at 80 ° C:
100 Stunden100 hours
200 Stunden200 hours
300 Stunden300 hours
100100
zu spröde für Zerreißversuchtoo brittle to be torn
185185
zu spröde für Zerreißversuchtoo brittle to be torn
zu spröde für Zerreißversuchtoo brittle to be torn
zu spröde für Zerreißversuchtoo brittle to be torn
zu spröde für Zerreißversuchtoo brittle to be torn
zu spröde für Zerreißversuchtoo brittle to be torn
zu spröde für Zerreißversuchtoo brittle to be torn
zu spröde für Zerreißversuchtoo brittle to be torn
zu spröde für Zerreißversuchtoo brittle to be torn
zu spröde für Zerreißversuchtoo brittle to be torn
zu spröde für Zerreißversuchtoo brittle to be torn
6060
4040
315315
120120
55 41 99 75 9055 41 99 75 90
253 290 271253 290 271
245 260 258245 260 258
258 253 264258 253 264
3030th
7070
203203
285285
90 35 98 6090 35 98 60
5555
190 170 177190 170 177
153 149 148153 149 148
177 178 182177 178 182
100 150 345100 150 345
185 34 95 43 40185 34 95 43 40
148148
110110
7272
98 88 5298 88 52
7777
Der Grundgedanke der vorliegenden Erfindung läßt sich sowohl bei der Herstellung thermoplastisch verarbeitbarer Polyurethane, die z. B. im Spritzguß oder auf der Walze verarbeitet werden können, als auch für die Herstellung gießbarer Polyurethanelastomerer anwenden.The basic idea of the present invention can be thermoplastic both in the production processable polyurethanes z. B. can be processed by injection molding or on the roller than can also be used for the production of castable polyurethane elastomers.
Claims (7)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1966C0040839 DE1301566B (en) | 1966-11-30 | 1966-11-30 | Process for the production of hydrolysis-resistant polyurethane elastomers |
| GB4528367A GB1147852A (en) | 1966-11-30 | 1967-10-04 | Improvements in or relating to polyurethane elastomers |
| FR130276A FR1546122A (en) | 1966-11-30 | 1967-11-29 | Process for the production of hydrolytically stable polyurethane elastomers with improved properties and products thus obtained |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1966C0040839 DE1301566B (en) | 1966-11-30 | 1966-11-30 | Process for the production of hydrolysis-resistant polyurethane elastomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1301566B true DE1301566B (en) | 1969-08-21 |
Family
ID=7024322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1966C0040839 Pending DE1301566B (en) | 1966-11-30 | 1966-11-30 | Process for the production of hydrolysis-resistant polyurethane elastomers |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1301566B (en) |
| GB (1) | GB1147852A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0785224A2 (en) | 1996-01-19 | 1997-07-23 | Hoechst Aktiengesellschaft | Process for preparing hydrophilic hydrogels with high swelling capacity |
| US5945495A (en) * | 1996-01-19 | 1999-08-31 | Basf Corporation | Use of surfactants in the drying of hydrophilic highly swellable hydrogels |
| US6313076B1 (en) | 1999-07-06 | 2001-11-06 | Clariant Gmbh | Use of polymers as antimisting additives in water-based cooling lubricants |
| US6380137B1 (en) | 1999-03-03 | 2002-04-30 | Clariant Gmbh | Copolymers and their use as drilling aids |
| US6414075B1 (en) | 1999-07-06 | 2002-07-02 | Clariant Gmbh | Use of polymers as antimisting additives in water-based cooling lubricants |
| US6462000B1 (en) | 1999-07-06 | 2002-10-08 | Clariant Gmbh | Use of polymers as antimisting additives in water-based cooling lubricants |
| US6657015B1 (en) | 1998-11-26 | 2003-12-02 | Basf Aktiengesellschaft | Method for the secondary cross-linking of hydrogels with 2-oxotetrahydro-1,3-oxazines |
| WO2005042039A2 (en) | 2003-10-31 | 2005-05-12 | Basf Aktiengesellschaft | Blood- and/or body fluid-absorbing hydrogel |
| EP1630181A1 (en) | 2004-07-22 | 2006-03-01 | Clariant GmbH | Thermostable, watersoluble at high temperatures curable Polymer |
| US7150319B2 (en) | 2001-10-12 | 2006-12-19 | Clariant Uk Ltd. | Method for reducing or completely eliminating water influx in an underground formation, and crosslinkable copolymers for implementing said method |
| EP1736508A1 (en) | 2005-06-22 | 2006-12-27 | Basf Aktiengesellschaft | Hydrogel-forming polymers with increased permeability and high absorption capacity |
| EP2345432A2 (en) | 2002-06-11 | 2011-07-20 | Basf Se | Method for producing esters from polyalcohols |
| EP3549820A1 (en) | 2018-04-04 | 2019-10-09 | Eric Aronoff | Surface protection articles and methods |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE754571A (en) * | 1969-08-07 | 1971-01-18 | Bayer Ag | SEGMENTED POLYURETHANE ELASTOMERS |
| CN101663343A (en) * | 2007-03-29 | 2010-03-03 | 路博润高级材料公司 | Use the thermoplastic polyurethane of the mixture preparation of polyester glycol and poly-(propylene oxide) glycol |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1238718A (en) * | 1957-05-07 | 1960-08-19 | Goodrich Co B F | Urethanes of hard thermoplastic polyesters |
| GB856731A (en) * | 1958-02-19 | 1960-12-21 | Ici Ltd | Improvements in or relating to the manufacture of coating compositions for electrical conductors |
| DE1147035B (en) * | 1959-01-30 | 1963-04-11 | Du Pont | Process for the production of elastomeric polyurethanes |
| FR1346808A (en) * | 1962-02-19 | 1963-12-20 | Bayer Ag | New polyurethane polymers |
| GB947973A (en) * | 1961-03-28 | 1964-01-29 | Beck & Company G M B H Dr | Improvements in or relating to polyurethane lacquers |
| US3125617A (en) * | 1964-03-17 | Hoppe |
-
1966
- 1966-11-30 DE DE1966C0040839 patent/DE1301566B/en active Pending
-
1967
- 1967-10-04 GB GB4528367A patent/GB1147852A/en not_active Expired
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3125617A (en) * | 1964-03-17 | Hoppe | ||
| FR1238718A (en) * | 1957-05-07 | 1960-08-19 | Goodrich Co B F | Urethanes of hard thermoplastic polyesters |
| DE1106958B (en) * | 1957-05-07 | 1961-05-18 | Goodrich Co B F | Process for the production of thermoplastic, linear, practically non-crosslinked polyester urethanes |
| GB856731A (en) * | 1958-02-19 | 1960-12-21 | Ici Ltd | Improvements in or relating to the manufacture of coating compositions for electrical conductors |
| DE1147035B (en) * | 1959-01-30 | 1963-04-11 | Du Pont | Process for the production of elastomeric polyurethanes |
| GB947973A (en) * | 1961-03-28 | 1964-01-29 | Beck & Company G M B H Dr | Improvements in or relating to polyurethane lacquers |
| FR1346808A (en) * | 1962-02-19 | 1963-12-20 | Bayer Ag | New polyurethane polymers |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0785224A2 (en) | 1996-01-19 | 1997-07-23 | Hoechst Aktiengesellschaft | Process for preparing hydrophilic hydrogels with high swelling capacity |
| US5945495A (en) * | 1996-01-19 | 1999-08-31 | Basf Corporation | Use of surfactants in the drying of hydrophilic highly swellable hydrogels |
| US6657015B1 (en) | 1998-11-26 | 2003-12-02 | Basf Aktiengesellschaft | Method for the secondary cross-linking of hydrogels with 2-oxotetrahydro-1,3-oxazines |
| US6380137B1 (en) | 1999-03-03 | 2002-04-30 | Clariant Gmbh | Copolymers and their use as drilling aids |
| US6414075B1 (en) | 1999-07-06 | 2002-07-02 | Clariant Gmbh | Use of polymers as antimisting additives in water-based cooling lubricants |
| US6462000B1 (en) | 1999-07-06 | 2002-10-08 | Clariant Gmbh | Use of polymers as antimisting additives in water-based cooling lubricants |
| US6313076B1 (en) | 1999-07-06 | 2001-11-06 | Clariant Gmbh | Use of polymers as antimisting additives in water-based cooling lubricants |
| US7150319B2 (en) | 2001-10-12 | 2006-12-19 | Clariant Uk Ltd. | Method for reducing or completely eliminating water influx in an underground formation, and crosslinkable copolymers for implementing said method |
| EP2345432A2 (en) | 2002-06-11 | 2011-07-20 | Basf Se | Method for producing esters from polyalcohols |
| EP2345431A2 (en) | 2002-06-11 | 2011-07-20 | Basf Se | Method for producing esters from polyalcohols |
| WO2005042039A2 (en) | 2003-10-31 | 2005-05-12 | Basf Aktiengesellschaft | Blood- and/or body fluid-absorbing hydrogel |
| EP1630181A1 (en) | 2004-07-22 | 2006-03-01 | Clariant GmbH | Thermostable, watersoluble at high temperatures curable Polymer |
| EP1736508A1 (en) | 2005-06-22 | 2006-12-27 | Basf Aktiengesellschaft | Hydrogel-forming polymers with increased permeability and high absorption capacity |
| EP3549820A1 (en) | 2018-04-04 | 2019-10-09 | Eric Aronoff | Surface protection articles and methods |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1147852A (en) | 1969-04-10 |
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