DE1212719B - Process for the production of polyurethane foams - Google Patents
Process for the production of polyurethane foamsInfo
- Publication number
- DE1212719B DE1212719B DEB76646A DEB0076646A DE1212719B DE 1212719 B DE1212719 B DE 1212719B DE B76646 A DEB76646 A DE B76646A DE B0076646 A DEB0076646 A DE B0076646A DE 1212719 B DE1212719 B DE 1212719B
- Authority
- DE
- Germany
- Prior art keywords
- tin
- production
- compounds
- catalyst
- halides
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 229920005830 Polyurethane Foam Polymers 0.000 title claims description 5
- 239000011496 polyurethane foam Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 19
- 150000001408 amides Chemical class 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
- 229920001228 polyisocyanate Polymers 0.000 claims description 4
- 239000005056 polyisocyanate Substances 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 17
- -1 2-ethyl Chemical group 0.000 description 15
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 235000011150 stannous chloride Nutrition 0.000 description 13
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000004132 cross linking Methods 0.000 description 5
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 5
- 239000006260 foam Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 125000005474 octanoate group Chemical group 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- ZSUXOVNWDZTCFN-UHFFFAOYSA-L tin(ii) bromide Chemical compound Br[Sn]Br ZSUXOVNWDZTCFN-UHFFFAOYSA-L 0.000 description 2
- JTDNNCYXCFHBGG-UHFFFAOYSA-L tin(ii) iodide Chemical compound I[Sn]I JTDNNCYXCFHBGG-UHFFFAOYSA-L 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- PXRFIHSUMBQIOK-CVBJKYQLSA-L (z)-octadec-9-enoate;tin(2+) Chemical compound [Sn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O PXRFIHSUMBQIOK-CVBJKYQLSA-L 0.000 description 1
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010097 foam moulding Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- OBBXFSIWZVFYJR-UHFFFAOYSA-L tin(2+);sulfate Chemical compound [Sn+2].[O-]S([O-])(=O)=O OBBXFSIWZVFYJR-UHFFFAOYSA-L 0.000 description 1
- 229910000375 tin(II) sulfate Inorganic materials 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/248—Catalysts containing metal compounds of tin inorganic compounds of tin
-
- 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
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
Verfahren zur Herstellung von Polyurethanschaumstoffen Die Verwendung von Organozinnverbindungen oder von Sn(II)-salzen als Katalysatoren bei der Herstellung von Schaumstoffen aus Polyhydroxyl-und/oder Polycarboxylverbindungen, Polyisocyanaten und gegebenenfalls Wasser ist bekannt. Eine Zu sammenfassung dieser als Katalysatoren geeigneten Zinnverbindungen findet sich bei A. F a r k a s und G. A. M i lis in »Catalytic Effects in Isocyanate Reactions«, Advances in Catalysis, Vol. 13, S. 393ff., New York: Academic Press, 1962. Geeignete Verbindungen sindZinn(II)-octoat, Zinn(II)-oleat, Zinn(II) chlorid, Dibutylzinndilaurat, Dibutylzinn di- (2-äthyl)-hexoat usw.Process for the production of polyurethane foams The use of organotin compounds or of Sn (II) salts as catalysts in the production of foams made from polyhydroxyl and / or polycarboxyl compounds, polyisocyanates and possibly water is known. A summary of these as catalysts suitable tin compounds can be found in A. F a r k a s and G. A. M i lis in "Catalytic Effects in Isocyanate Reactions", Advances in Catalysis, Vol. 13, pp. 393ff., New York: Academic Press, 1962. Suitable compounds are tin (II) octoate, Tin (II) oleate, tin (II) chloride, dibutyltin dilaurate, dibutyltin di- (2-ethyl) -hexoate etc.
Der zur Zeit meistverwendete Katalysator für Isocyanat-Hydroxyl-Vernetzungsreaktionen ist Zinn(II)-octoat. Das Produkt ist aber sehr empfindlich gegenüber hydrolytischen und oxydativen Einflüssen und schwankt in seiner Aktivität als Katalysator häufig. Currently the most widely used catalyst for isocyanate-hydroxyl crosslinking reactions is tin (II) octoate. But the product is very sensitive to hydrolytic and oxidative influences and often fluctuates in its activity as a catalyst.
Ein weiterer Katalysator zur Herstellung von Urethangruppen enthaltenden Schaumstoffen ist auch Zinn(II)-chlorid. Zinn(II)-chlorid ist allerdings noch empfindlicher gegenüber Luftsauerstoff und Wasserdampf als Zinn(II)-octoat.Another catalyst for the production of urethane groups containing Foam is also tin (II) chloride. Tin (II) chloride is, however, even more sensitive to atmospheric oxygen and water vapor as tin (II) octoate.
Es wurde gefunden, daß Additionsverbindungen von Zinn(II)-halogeniden mit Säureamiden die oben angeführten Mängel der starken Empfindlichkeit gegenüber oxydativen Einflüssen nicht zeigen. Zinn(II)-chlorid ist zwar als Katalysator für Isocyanat-Hydroxyl-Vernetzungen bekannt, wird aber in der Praxis kaum eingesetzt, da wasserfreies Zinn(II)-chlorid in organischen Lösungsmitteln nicht oder kaum löslich ist. Zudem ist Zinn(II)-chlorid gegenüber hydrolytischen Einflüssen, z. B. Luftfeuchtigkeit sehr empfindlich und verliert deshalb rasch seine katalytische Wirksamkeit bei Isocyanat - Hydroxyl - Vernetzungen. It has been found that addition compounds of tin (II) halides with acid amides the above-mentioned deficiencies of the strong sensitivity to Do not show oxidative influences. Tin (II) chloride is used as a catalyst for Isocyanate-hydroxyl crosslinking is known, but is rarely used in practice, since anhydrous tin (II) chloride is insoluble or hardly soluble in organic solvents is. In addition, tin (II) chloride is resistant to hydrolytic influences, e.g. B. Humidity very sensitive and therefore quickly loses its catalytic effectiveness with isocyanate - hydroxyl crosslinks.
Gegenüber dem als Katalysator für Polyurethanschaumstoffe in der Praxis meist verwendeten Sn(II)-octoat haben die Additionsverbindungen aus Zinn(II)-halogeniden und Säureamiden folgende Vorteile: 1. Unempfindlichkeit gegen Feuchtigkeit und gegenüber Luftsauerstoff [SnCl2, Sn(II)-octoat hydrolysieren rasch und oxydieren verhältnismäßig schnell zu, als Katalysatoren unwirksamen, entsprechenden Sn(IV)-salzen]. Compared to the catalyst for polyurethane foams in the In practice most commonly used Sn (II) octoate are the addition compounds of tin (II) halides and acid amides have the following advantages: 1. Insensitivity to moisture and to Atmospheric oxygen [SnCl2, Sn (II) octoate hydrolyze rapidly and oxidize proportionally quickly to corresponding Sn (IV) salts, which are ineffective as catalysts].
2. Die neuen Additionsverbindungen aus Zinn(II)-halogeniden und Säureamiden sind als einziger bekannter Zinnkatalysator mit wenig Wasser vollkommen mischbar; dies erschließt neue Anwendungsmöglichkeiten. 2. The new addition compounds made from tin (II) halides and acid amides are the only known tin catalyst that are completely miscible with a little water; this opens up new application possibilities.
3. Die Reaktion zwischen Polyhydroxylverbindung und Polyisocyanat ist bei Verwendung von Sn(II)-octoat als Katalysator sehr empfindlich bei huber dosierung des Katalysators, d. h., man erhält dann einen unbrauchbaren Schaum. Wenn dagegen die beansprucht verwendeten Additionsverbindungen als Katalysator zur Reaktion verwendet werden, so verläuft die Reaktion selbst bei Anwendung der 1,5- bis Sfachen Katalysatormenge normal. 3. The reaction between polyhydroxyl compound and polyisocyanate is very sensitive at huber when using Sn (II) octoate as a catalyst dosing of the catalyst, d. i.e., an unusable foam is then obtained. if on the other hand, the claimed addition compounds used as a catalyst for the reaction are used, the reaction proceeds even if 1.5 to 5 times are used Normal amount of catalyst.
4. Die Additionsverbindungen sind sehr einfach in der Herstellung. 4. The addition compounds are very easy to manufacture.
5. Die gegenüber Sn(II)-octoat erhöhte Steigzeit macht die Additionsverbindungen der Zinnhalogenide/Säureamide zur sogenannten »Formverschäumung« sehr geeignet, für die Katalysatoren mit längerer Steigzeit gesucht werden. 5. The rise time, which is increased compared to Sn (II) octoate, makes the addition compounds the tin halides / acid amides are very suitable for so-called »foam molding«, for the catalysts with longer rise times are sought.
6. Werden Polycarboxylverbindungen bei der Isocyanatvernetzungsreaktion verwendet, so verläuft die Reaktion bei Verwendung von SnCl2/Dimethylformamid als Katalysator wesentlich rascher, wenn auf das sonst übliche, sehr teure Triäthylendiamin (1 ,4-Diaza-bicyclo [2,2,2joctan) ganz verzichtet wird. 6. Become polycarboxyl compounds in the isocyanate crosslinking reaction used, the reaction proceeds when using SnCl2 / dimethylformamide as Catalyst much faster if on the otherwise common, very expensive triethylenediamine (1,4-Diaza-bicyclo [2,2,2joctane) is completely dispensed with.
Gegenstand der Erfindung ist also ein Verfahren zur Herstellung von Polyurethanschaumstoffen aus Polyhydroxyl- und/oder Polycarboxylverbindungen, Polyisocyanaten und gegebenenfalls Wasser, in Gegenwart yon Zinnkomplexen, die aus Additionsverbindungen von Zinn(II)-halogeniden mit Säureamiden bestehen. The invention is therefore a process for the production of Polyurethane foams made from polyhydroxyl and / or polycarboxyl compounds, polyisocyanates and optionally water, in the presence of tin complexes derived from addition compounds consist of tin (II) halides with acid amides.
Bei einem Vergleich zwischen Zinn(II)-chlorid, Zinn(II)-octoat und den beanspruchten Zinn(II)-halogenid -Säureamiden als Katalysatoren für Isocyanatvernetzungen -wurde von folgendem Ansatz ausgegangen: 2000 g Polyhydroxylverbindung (Molekulargewicht 3500), 4 g N-Methylmorpholin, 3 g Tetramethylen- butandiamin, 22 g Polysiloxanpolyalkylenglykolblockmischpolymerisat, 70 g Wasser. When comparing tin (II) chloride, tin (II) octoate and the claimed tin (II) halide Acid amides as catalysts for isocyanate crosslinking the following approach was used: 2000 g of polyhydroxyl compound (Molecular weight 3500), 4 g N-methylmorpholine, 3 g tetramethylene butanediamine, 22 g polysiloxane polyalkylene glycol block copolymer, 70 g water.
200 g obiger Mischung kommen zu: 80 g Toluylendiisocyanat und 1 bis
2 g Katalysator, jeweils auf 1 g Zinn Zinn berechnet, um vergleichbare Werte zu
haben.
Als Säureamide kommen in Frage: Dimethylformamid, Monomethylformamid oder Formamid, aber auch Acetamid, Propionamid, Chloracetamid, Oxybutyramid, Steaorylamid oder Benzamid eignen sich zur Umsetzung mit Zinn(II)-halogeniden. Alle diese Zinn(Il)-halogenid-Säureamid-Verbindungen zeigenbei der Isocyanat-Hydroxyl-Vernetzung mehr oder minder ausgeprägte Katalysatoreigenschaften. Possible acid amides are: dimethylformamide, monomethylformamide or formamide, but also acetamide, propionamide, chloracetamide, oxybutyramide, steaorylamide or benzamide are suitable for reaction with tin (II) halides. All of these tin (II) halide acid amide compounds show more or less pronounced catalyst properties in the isocyanate-hydroxyl crosslinking.
Bei der bekannten Umsetzung von Säureamiden mit Zinn(II)-halogeniden kann sowohl von wasserhaltigen wie auch von wasserfreien Zinn(II)-salzen ausgegangen werden. In allen Fällen ergibt sich bei der Reaktion zwischen Säureamiden und Zinn(II)-halogeniden eine mehr oder weniger starke Wärmeentwicklung. Die Verbindungen, deren Herstellung an dieser Stelle nicht beansprucht wird, aus Säureamiden-Zinn(II)-halogeniden können kristalliner Natur sein. So kristallisiert z. B. bei der Reaktion von wasserfreiem Zinn(II)-bromid oder -chlorid in einem geringen Überschuß an Dimethylformamid die entsprechende Additionsverbindung in der Kälte aus. In the known reaction of acid amides with tin (II) halides Both water-containing and water-free tin (II) salts can be assumed will. In all cases, the reaction between acid amides and tin (II) halides results a more or less strong heat development. The connections, their production Not claimed at this point, from acid amide tin (II) halides can crystalline nature be. So crystallizes z. B. in the reaction of anhydrous Tin (II) bromide or chloride in a slight excess of dimethylformamide corresponding addition compound in the cold.
Meist erübrigt sich ein Isolieren der kristallinen Additionsverbindung. Als Katalysator für Schaumstoffe aus Isocyanatbasis kann die Additionsverbindung auch in einem- Überschuß an Säureamid oder in einem Lösungsmittel gelöst sein.In most cases, there is no need to isolate the crystalline addition compound. The addition compound also be dissolved in an excess of acid amide or in a solvent.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB76646A DE1212719B (en) | 1964-05-05 | 1964-05-05 | Process for the production of polyurethane foams |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB76646A DE1212719B (en) | 1964-05-05 | 1964-05-05 | Process for the production of polyurethane foams |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1212719B true DE1212719B (en) | 1966-03-17 |
Family
ID=6979167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB76646A Pending DE1212719B (en) | 1964-05-05 | 1964-05-05 | Process for the production of polyurethane foams |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1212719B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4606829A1 (en) * | 2024-02-23 | 2025-08-27 | Covestro Deutschland AG | Process for the preparation of alkoxysilane-functional polyurethanes and polyurethane ureas |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1212252A (en) * | 1957-09-25 | 1960-03-23 | Union Carbide Corp | Polyurethane foams and their manufacturing process |
-
1964
- 1964-05-05 DE DEB76646A patent/DE1212719B/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1212252A (en) * | 1957-09-25 | 1960-03-23 | Union Carbide Corp | Polyurethane foams and their manufacturing process |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4606829A1 (en) * | 2024-02-23 | 2025-08-27 | Covestro Deutschland AG | Process for the preparation of alkoxysilane-functional polyurethanes and polyurethane ureas |
| WO2025176593A1 (en) * | 2024-02-23 | 2025-08-28 | Covestro Deutschland Ag | Process for producing alkoxysilane-functional polyurethanes and polyurethane ureas |
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