DE1152537B - Process for the production of homogeneous plastics containing urethane groups - Google Patents
Process for the production of homogeneous plastics containing urethane groupsInfo
- Publication number
- DE1152537B DE1152537B DEF36971A DEF0036971A DE1152537B DE 1152537 B DE1152537 B DE 1152537B DE F36971 A DEF36971 A DE F36971A DE F0036971 A DEF0036971 A DE F0036971A DE 1152537 B DE1152537 B DE 1152537B
- Authority
- DE
- Germany
- Prior art keywords
- diisocyanate
- compounds
- plastics
- polyhydroxyl
- elongation
- 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.)
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Classifications
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- 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
- C08G18/63—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
- C08G18/632—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers onto polyethers
Description
INTERNAT. KL. C 08 gINTERNAT. KL. C 08 g
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
F 36971 IVc/39 bF 36971 IVc / 39 b
BEKANNTMACHUNG DER ANMELDUNG UND AUSGABE DER AUSLEGESCHRIFTs 8. AUGUST 1963NOTICE THE REGISTRATION AND ISSUE OF THE EDITORIAL AUGUST 8, 1963
Die Herstellung von Kunststoffen aus höhermolekularen linearen oder verzweigten Polyhydroxylverbindungen, Polyisocyanaten und gegebenenfalls Kettenverlängerungsmitteln bzw. Vernetzungsmitteln ist bekannt. Je nach Art der Komponenten, den angewandten Mengenverhältnissen und der Reihenfolge der Umsetzung können elastische Kunststoffe mit verschiedenen Härten und verschiedenem Eigenschaftsbild erhalten werden. Verwendet man als höhermolekulare Polyhydroxyverbindungen Polyester, so werden Kunststoffe mit hervorragenden mechanischen Eigenschaften erhalten, die jedoch infolge der Verseifbarkeit der Estergruppen keine sehr hohe Hydrolysebeständigkeit aufweisen. Ersetzt man die Polyester durch Polyäther, wie beispielsweise Polypropylen- oder Polyäthylenglykoläther, so erhöht sich dadurch zwar die Hydrolysebeständigkeit der entstehenden Kunststoffe, die mechanischen Eigenschaften, insbesondere die Einreißfestigkeit und die Zerreißfestigkeit fallen dagegen stark ab.The production of plastics from high molecular weight linear or branched polyhydroxyl compounds, Polyisocyanates and, if appropriate, chain extenders or crosslinking agents is known. Depending on the type of components, the proportions used and the sequence The implementation can be elastic plastics with different hardnesses and different properties can be obtained. If polyester is used as a higher molecular weight polyhydroxy compound, so plastics with excellent mechanical properties are obtained, but as a result the saponifiability of the ester groups do not have a very high resistance to hydrolysis. Replace one the polyesters are increased by polyethers such as polypropylene or polyethylene glycol ethers This increases the hydrolysis resistance of the resulting plastics, the mechanical Properties, in particular the tear strength and the tear strength, on the other hand, drop sharply.
Es wurde nun die überraschende Beobachtung gemacht, daß man homogene Urethangruppen aufweisende Kunststoffe auf der Grundlage von Polyhydroxylverbindungen mit einem Molekulargewicht von mindestens 800, Polyisocyanaten und gegebenenfalls Kettenverlängerungs- bzw. Vernetzungsmitteln sowie Polymerisaten unter Formgebung mit vorzüglichen mechanischen Eigenschaften erhält, wenn man als Polyhydroxylverbindungen solche modifizierte verwendet, in denen vorher Polymerisate oder Mischpolymerisate aus polymerisierbaren ungesättigten Verbindungen in situ unter Pfropfpolymerisatbildung mit der Polyhydroxylverbindung hergestellt worden sind.The surprising observation has now been made that homogeneous urethane groups are obtained Plastics based on polyhydroxyl compounds with a molecular weight of at least 800, polyisocyanates and optionally chain extenders or crosslinking agents as well as polymers obtained by shaping with excellent mechanical properties if one those modified as polyhydroxyl compounds used in which previously polymers or Copolymers of polymerizable unsaturated compounds in situ with graft polymer formation with the polyhydroxyl compound.
Es ist bekannt, Vinylpolymere getrennt den Ausgangsmaterialien für die Herstellung von Kunststoffen zuzusetzen. Erfindungsgemäß werden aber die Polymerisate in dem Polyalkylenglykoläther in situ hergestellt. Es ist ferner bekannt, Mischpolymerisate aus Allylalkohol und Styrol mit freien Hydroxylgruppen als Ausgangsmaterialien zur Herstellung von Urethangruppen enthaltenden Kunststoffen einzusetzen. Diese sind jedoch zwangläufig bezüglich der Hydroxylgruppen verzweigt und lassen sich zur Herstellung elastischer Produkte nicht einsetzen. Überhaupt haben derartige Mischpolymerisate den Nachteil, daß sich Verzweigungsgrad sowie Zahl und Anordnung der Hydroxylgruppen, die mit dem PoIyisocyanat in Reaktion treten, nicht unabhängig voneinander variieren lassen.It is known that vinyl polymers separate the starting materials for the manufacture of plastics to add. According to the invention, however, the polymers are in situ in the polyalkylene glycol ether manufactured. It is also known that copolymers of allyl alcohol and styrene with free hydroxyl groups to be used as starting materials for the production of plastics containing urethane groups. However, these are inevitably branched with respect to the hydroxyl groups and can be used for production Do not use elastic products. In general, such copolymers have the disadvantage that the degree of branching and the number and arrangement of the hydroxyl groups with the polyisocyanate react, do not allow them to vary independently of one another.
Die Verfahrensprodukte besitzen vor allem eine verbesserte Einreißfestigkeit und Festigkeit. Bei Ver-Verfahren zur HerstellungAbove all, the products of the process have improved tear resistance and strength. In Ver proceedings for the production
von homogenen, Urethangruppenof homogeneous, urethane groups
aufweisenden Kunststoffencontaining plastics
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft,
LeverkusenPaint factories Bayer Aktiengesellschaft,
Leverkusen
Dr. Wulf von Bonin, Dr. Erwin Müller, Leverkusen, und Dr. Dr. h. c, Dr. e. h., Dr. h. c, Dr. h. c, Dr. e. h.Dr. Wulf von Bonin, Dr. Erwin Müller, Leverkusen, and Dr. Dr. H. c, Dr. e. i.e., Dr. H. c, Dr. H. c, Dr. e. H.
Otto Bayer, Leverkusen-Bayerwerk,Otto Bayer, Leverkusen-Bayerwerk,
sind als Erfinder genannt wordenhave been named as inventors
wendung von modifizierten Polypropylenglykoläthern wird beispielsweise die Einreißfestigkeit der daraus erhaltenen Kunststoffe um das Zwei- bis Dreifache erhöht. Weiterhin erfolgt eine Zunahme der Festigkeit und der Härte.The use of modified polypropylene glycol ethers, for example, increases the tear resistance of the resulting obtained plastics increased by two to three times. There is also an increase in strength and the hardness.
Die Härte der Polyurethankunststoffe wird bekanntlich durch das Mengenverhältnis zwischen der höhermolekularen Polyhydroxylverbindung, dem niedermolekularen Kettenverlängerungsmittel und dem Diisocyanat bestimmt. Sie nimmt mit steigenden Mengen an Diisocyanat und Kettenverlängerungsmittel zu. Bei der erfindungsgemäßen Verwendung der modifizierten Polyhydroxylverbindungen werden schon durch Anwendung der üblichen Mengen an Diisocyanat und Kettenverlängerungsmittel Produkte mit hoher Härte erhalten. Weiterhin besitzen die Verfahrensprodukte eine erhöhte Quellbeständigkeit gegenüber Lösungsmitteln, und schließlich sei noch auf die Alterungsschutzwirkung hingewiesen, die derartige modifizierte Polyhydroxylverbindungen den entstehenden Kunststoffen verleihen.The hardness of polyurethane plastics is known by the ratio between the higher molecular weight polyhydroxyl compound, the low molecular weight chain extender and determined by the diisocyanate. It decreases with increasing amounts of diisocyanate and chain extenders to. When using the modified polyhydroxyl compounds according to the invention by using the usual amounts of diisocyanate and chain extender products obtained with high hardness. The process products also have increased resistance to swelling to solvents, and finally the anti-aging effect should be pointed out, the such give modified polyhydroxyl compounds to the resulting plastics.
Zur Herstellung des erfindungsgemäß zu verwendenden Ausgangsmaterials kommen neben den PoIyestern als höhermolekulare Polyhydroxylverbindungen besonders Polyäther wie Polyäthylenglykoläther, Poly-l,4-butylenglykoläther oder insbesondere PoIy-In addition to polyesters, the starting material to be used according to the invention is produced as higher molecular weight polyhydroxyl compounds especially polyethers such as polyethylene glycol ether, Poly-1,4-butylene glycol ether or especially poly-
309 650/289309 650/289
propylenglykoläther, sowie Polymischäther in Frage. Bei Verwendung der hydrophilen, jedoch modifizierten Polyäthylenglykoläther wird durch die Modifizierung eine zusätzliche Hydrophobierung erreicht.propylene glycol ether, as well as poly mixed ethers in question. When using the hydrophilic, but modified The modification provides polyethylene glycol ether with additional hydrophobicity.
Die erfindungsgemäß als Ausgangsmaterial zu verwendenden modifizierten Polyhydroxylverbindungen werden dadurch erhalten, daß man in der PoIyhydroxylverbindung polymerisierbare ungesättigte Verbindungen löst und anschließend unter Zusatz radikalbildender Initiatoren polymerisiert.The modified polyhydroxyl compounds to be used as starting material according to the invention are obtained by adding polymerizable unsaturated compounds in the polyhydroxyl compound Dissolves compounds and then polymerizes with the addition of radical-forming initiators.
Die in situ hergestellten Polymerisate sind in den Polyhydroxylverbindungen zum Teil als Homopolymerisate gelöst oder suspendiert enthalten. Es liegen jedoch auch Pfropfpolymerisate vor.Some of the polymers produced in situ are homopolymers in the polyhydroxyl compounds contained dissolved or suspended. However, there are also graft polymers.
Als polymerisierbare ungesättigte Verbindungen kommen hierbei solche Verbindungen in Betracht, die eine oder mehrere polymerisierbare Doppelbindungen enthalten. Beispielhaft seien genannt: Vinylaromaten, wie Styrol, Olefinkohlenwasserstoffe, Vinylester, wie Vinylacetat oder Vinylpropionat, Vinylhalogenide, wie Vinylchlorid oder Vinylidenchlorid. Auch (Meth-)Acrylsäure oder deren Derivate, wie Methylmethacrylat, Äthylacrylat oder Acrylnitril, sind hierfür geeignet. Die Verwendung von Polyvinylverbindungen, wie Triallylcyanurat oder Glykoldimethacrylat, ist ebenfalls möglich. Weiterhin sind auch solche Verbindungen geeignet, die noch reaktive, mit Isocyanaten oder anderen Verbindungen reagierende Gruppen enthalten, wie beispielsweise Methacrylamid, Methacrylamid-N-methylolallyläthe^Methacrylamid-N-methylolallyläther,Acrylsäure-/?-hydroxyäthylester oder Acrylsäureallylester. Die ungesättigten Verbindungen können rein oder im Gemisch miteinander eingesetzt werden. Vinylacetat, Vinylchlorid, Methylmethacrylat, Methacrylamid oder Styrol sowie besonders Acrylnitril seien hervorgehoben.Suitable polymerizable unsaturated compounds here are those compounds which contain one or more polymerizable double bonds. Examples include: vinyl aromatics, such as styrene, olefin hydrocarbons, vinyl esters, such as vinyl acetate or vinyl propionate, Vinyl halides such as vinyl chloride or vinylidene chloride. Also (meth) acrylic acid or its derivatives, such as methyl methacrylate, ethyl acrylate or acrylonitrile, are suitable for this. The usage of polyvinyl compounds, such as triallyl cyanurate or glycol dimethacrylate, is also possible. Furthermore, compounds that are still reactive with isocyanates or other compounds are also suitable Containing reactive groups, such as methacrylamide, methacrylamide-N-methylolallylether ^ methacrylamide-N-methylolallylether, acrylic acid - /? - hydroxyethyl ester or allyl acrylic acid. The unsaturated compounds can be used pure or in a mixture with one another will. Vinyl acetate, vinyl chloride, methyl methacrylate, methacrylamide or styrene and especially acrylonitrile are highlighted.
Zur Modifizierung der Polyhydroxylverbindungen werden in diesen 1 bis 60 Gewichtsprozent, bevorzugt 5 bis 30 Gewichtsprozent an Vinylverbindungen gelöst und nach Zusatz des Polymerisationsinitiators, gegebenenfalls unter Ausschluß von Luftsauerstoff, unter Rühren zur Polymerisation gebracht.In order to modify the polyhydroxyl compounds, 1 to 60 percent by weight are preferred 5 to 30 percent by weight of vinyl compounds dissolved and after addition of the polymerization initiator, if appropriate with exclusion of atmospheric oxygen, brought to polymerization with stirring.
Als Polymerisationsinitiatoren eignen sich die üblicherweise verwendeten Radikalbildner, wie beispielsweise Peroxyde vom Typ Lauroylperoxyd, Benzoylperoxyd oder Dicumylperoxyd, oder stickstoffhaltige Substanzen, Azodiisobutyronitril. Auch Redoxsysteme, wie Benzoylperoxyd-Dimethyltoluidin, können verwendet werden. Desgleichen kommt die Initiierung mit Hilfe energiereicher Strahlen in Betracht. Die Radikalbildner werden in Mengen von 0,01 bis 15 Gewichtsprozent, vorzugsweise 0,1 bis 5 Gewichtsprozent, bezogen auf die polymerisierbare Vinylverbindung, eingesetzt.The free radical formers usually used, such as, for example, are suitable as polymerization initiators Peroxides of the lauroyl peroxide, benzoyl peroxide or dicumyl peroxide type, or those containing nitrogen Substances, azodiisobutyronitrile. Redox systems, such as benzoyl peroxide dimethyl toluidine, can be used. Initiation with the help of high-energy rays can also be considered. The radical formers are used in amounts of 0.01 to 15 percent by weight, preferably 0.1 to 5 percent by weight, based on the polymerizable vinyl compound, is used.
Am zweckmäßigsten wird der Polymerisationsinitiator in der Vinylverbindung gelöst und diese Lösung mit der Polyhydroxylverbindung vereinigt, homogenisiert und durch Erwärmen unter Luftausschluß polymerisiert. Es ist jedoch ohne weiteres möglich, die Arbeitsweise zu variieren und den Erfordernissen des einzelnen Falles anzugleichen.Most advantageously, the polymerization initiator is dissolved in the vinyl compound and this Solution combined with the polyhydroxyl compound, homogenized and heated with exclusion of air polymerized. However, it is easily possible to vary the mode of operation and the To match the requirements of the individual case.
Als Polyisocyanate sind bevorzugt Diisocyanate zu nennen, wie z. B. n-Butylendiisocyanat, Hexamethylendiisocyanat, m-Xylylendiisocyanat, p-Xylylendiisocyanat, 4,4'-Dimethyl-l,3-xylylendiisocyanat, Cyclohexylen-^'-diisocyanat, m-Phenylendiisocyanat, p-Phenylendiisocyanat, 1-Alkylphenylen-2,4-diisocyanate, 3-(a-Isocyanatoäthyl)-phenylisocyanat, l-Alkylphenylen-Zjö-diisocyanate, 2,6-Diäthylphenylen-l,4-diisocyanat, DiphenyImethan-4,4'-diisocyanat, Diphenyl-dimethylmethan-4,4'-diisocyanat oder Naphthylen-l^-diisocyanat, auch trioder mehrfunktionelle Isocyanate können mitverwendet werden, z. B. 2,4,6-Triisocyanatotoluol.Preferred polyisocyanates are diisocyanates, such as. B. n-butylene diisocyanate, hexamethylene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, 4,4'-dimethyl-1,3-xylylene diisocyanate, Cyclohexylene - ^ '- diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, 1-alkylphenylene-2,4-diisocyanate, 3- (a-Isocyanatoethyl) phenyl isocyanate, 1-alkylphenylene-Zjö-diisocyanate, 2,6-diethylphenylene-1,4-diisocyanate, Diphenyl imethane-4,4'-diisocyanate, diphenyl-dimethylmethane-4,4'-diisocyanate or naphthylene-l ^ -diisocyanate, also trioder multifunctional isocyanates can also be used, e.g. B. 2,4,6-triisocyanatotoluene.
Die erfindungsgemäß zu verwendenden modifizierten Polyhydroxylverbindungen können nach verschiedenen bekannten Verfahren mit Polyisocyanaten und Kettenverlängerungs- bzw. Vernetzungsmitteln in hochwertige Kunststoffe übergeführt werden. Man kann beispielsweise die höhermolekularen Polyhydroxylverbindungen mit einem Überschuß an Diisocyanaten umsetzen und dann niedermolekulare Verbindungen, wie beispielsweise Glykole, Diamine, oder Wasser in einem solchen Mengenverhältnis zusetzen, daß nach der Umsetzung noch NCO-Gruppen vorhanden sind, die für die Vernetzung zur Verfügung stehen. Auf diese Weise können Formkörper gegossen werden, die beim Nachheizen verfestigen und ihre endgültigen Eigenschaften annehmen. Verzichtet man auf eine längere Nachheizzeit nach dem Gießprozeß, so entstehen Produkte, die unter Feuchtigkeitsausschluß gelagert zu einem beliebigen späteren Zeitpunkt thermoplastisch verformt werden können. Auf diese Weise können ebenfalls Produkte mit verschiedenen Härtegraden und hochelastischen Eigenschaften erhalten werden.The modified polyhydroxyl compounds to be used according to the invention can be converted into high-quality plastics by various known processes with polyisocyanates and chain extenders or crosslinking agents. For example, the higher molecular weight polyhydroxyl compounds can be reacted with an excess of diisocyanates and then low molecular weight compounds such as glycols, diamines or water can be added in such a proportion that after the reaction there are still NCO groups that are available for crosslinking. In this way, moldings can be cast which solidify on post-heating and take on their final properties. If a longer post-heating time after the casting process is dispensed with, products are produced which, stored in the absence of moisture, can be thermoplastically deformed at any later point in time. In this way, products with different degrees of hardness and highly elastic properties can also be obtained.
Wählt man die Mengenverhältnisse zwischen der höhermolekularen Polyhydroxylverbindung, den niedermolekularen bifunktionellen Kettenverlängerungsmitteln und dem Diisocyanat derart, daß nach der Umsetzung noch Hydroxylgruppen vorhanden sind, so entstehen lagerfähige thermoplastische Produkte, die sich auf der Walze verarbeiten lassen, und beispielsweise nach Zugabe von weiterem Diisocyanat, insbesondere dimerem Toluylendiisocyanat, wobei sie in den vernetzten, elastischen Zustand übergehen. If you choose the proportions between the higher molecular weight polyhydroxyl compound, the low molecular weight bifunctional chain extenders and the diisocyanate such that after There are still hydroxyl groups left after the reaction, this results in storable thermoplastic products, which can be processed on the roller, and for example after adding more diisocyanate, in particular dimeric toluene diisocyanate, where they pass into the crosslinked, elastic state.
Die lagerfähigen, Hydroxylgruppen enthaltenden Produkte können nicht nur mit Diisocyanaten, sondern auch beispielsweise mit Schwefel, Peroxyden oder Formaldehyd vernetzt werden. Zweckmäßig ist dabei, daß die Hydroxylgruppen enthaltenden Ketten Komponenten eingebaut enthalten, die mit den genannten Verbindungen unter Vernetzung reagieren können. Diese Komponenten werden zweckmäßigerweise mittels einer niedermolekularen, bifunktionellen Hydroxylverbindung eingebaut.The storable, hydroxyl-containing products can not only with diisocyanates, but can also be crosslinked, for example, with sulfur, peroxides or formaldehyde. Is expedient while that the chains containing hydroxyl groups contain components incorporated with the compounds mentioned can react with crosslinking. These components are expedient incorporated by means of a low molecular weight, bifunctional hydroxyl compound.
So erhält man beispielsweise durch Umsetzung der höhermolekularen Polyhydroxylverbindungen mit Glycerinmonoallyläther und Diisocyanaten Produkte, die mit Schwefel vernetzbar sind. Beim Ersatz des Glycerinmonoallyläthers durch m-Dioxäthyltoluidin oder durch Ν,Ν'-Bismethyl-bis-^-hydroxyäthyl-4,4'-diaminodiphenylmethan werden Produkte erhalten, die mit Formaldehyd vernetzbar sind. Verwendet man als Diisocyanat das 4,4'-Diphenylmethandiisocyanat, so entstehen Produkte, die mit Peroxyden vernetzbar sind.For example, by reacting the higher molecular weight polyhydroxyl compounds with Glycerine monoallyl ether and diisocyanate products that can be crosslinked with sulfur. When replacing the Glycerin monoallyl ethers by m-dioxäthyltoluidin or by Ν, Ν'-bismethyl-bis - ^ - hydroxyethyl-4,4'-diaminodiphenylmethane products are obtained that can be crosslinked with formaldehyde. If the diisocyanate used is 4,4'-diphenylmethane diisocyanate, this creates products that can be crosslinked with peroxides.
In 200 g einer aus einem linearen Polypropylenglykoläther und Acrylnitril erhaltenen Polyhydroxylverbindung (2Ofl/o Acrylnitril; OH-ZaM 45) werden nach dem Entwässern· bei 130° C/12 mm 60 g 1,5-Naphthylendiisocyanat eingerührt. Die Tempera-After dehydration, 60 g of 1,5-naphthylene diisocyanate are stirred into 200 g of a polyhydroxyl compound (2O fl / o acrylonitrile; OH-ZaM 45) obtained from a linear polypropylene glycol ether and acrylonitrile. The tempera-
5 65 6
tür steigt auf 137- C an. Nach etwa 15 Minuten formbare wachsartige Masse, deren mechanische werden 16,5 g Butandiol-1,4 in die Schmelze einge- Eigenschaften nicht gemessen werden konnten, rührt, dann gießt man die homogene Masse in For-door rises to 137- C. After about 15 minutes moldable waxy mass, its mechanical 16.5 g of 1,4-butanediol are incorporated into the melt properties could not be measured, stirs, then the homogeneous mass is poured into the
men. Nach 24stündigem Nachheizen bei 100° C Beispiel 4men. After 24 hours of post-heating at 100 ° C, Example 4
wird ein Material mit folgenden Eigenschaften er- 5 Nach den im Beispiel 1 angegebenen Versuchshalten: bedingungen werden 200 g einer aus einem linearen a material with the following properties is obtained. According to the test results given in Example 1: conditions, 200 g of one from a linear
Polypropylenglykoläther und Acrylnitril (20% Acryl-Polypropylene glycol ether and acrylonitrile (20% acrylic
Zugfestigkeit, DIN 53 504 192 kg/cm* nitril) hergestellten Polyhydroxylverbindung mit 50 gTensile strength, DIN 53 504 192 kg / cm * nitrile) polyhydroxyl compound produced with 50 g
Bruchdehnung, DIN53504 .... 305% p-Phenylendiisocyanat und 20g 2,3-Butandiol um-Elongation at break, DIN53504 .... 305% p-phenylene diisocyanate and 20g 2,3-butanediol um-
Bleibende Dehnung, DIN 53 504 52% 10 gesetzt. Das erhaltene Material hat folgende mecha-Permanent elongation, DIN 53 504 52% 10 set. The material obtained has the following mechanical
Einreißfestigkeit, DIN 53 515 ... 69 kg/cm nische Eigenschaften:Tear resistance, to DIN 53 515 ... 69 kg / cm i n h e sc properties:
Shore-HärteA, DIN53505 .... 96 „ . . , . .... , a Shore hardness A, DIN53505 .... 96 ". . ,. ...., a
Stoßelastizität, DIN 53 512 54% l^lft™ Ifn^™~ Resilience to impact, DIN 53 512 54% l ^ lft ™ If n ^ ™ ~
Bruchdehnung 360%Elongation at break 360%
, . , _, , .,. , Bleibende Dehnung 37%,. , _,,.,. , Permanent elongation 37%
Em unter den gleichen Versuchsbedmgungen und 15 Einreißfestigkeit 49 kg/cmEm under the same test conditions and 15 tear strength 49 kg / cm
Mengenverhältnissen erhaltenes Produkt, das aus Shore-Härte A 91Product obtained in quantitative proportions, which is made from Shore hardness A 91
einem linearen Polypropylenglykoläther (OH-Zahl Stoßelastizität 42%a linear polypropylene glycol ether (OH number impact elasticity 42%
45; ohne Acrylnitril) erhalten wurde, zeigt folgende45; without acrylonitrile) shows the following
Werte: Ein unter den gleichen Versuchsbedingungen undValues: One under the same test conditions and
20 Mengenverhältnissen erhaltenes Produkt, das ausProduct obtained from 20 proportions
Zugfestigkeit 111 kg/cm2 einem linearen Polypropylenglykoläther (OH-ZahlTensile strength 111 kg / cm 2 of a linear polypropylene glycol ether (OH number
Bruchdehnung 255% 44; ohne Acrylnitril) erhalten wurde, zeigt folgendeElongation at break 255% 44; without acrylonitrile) shows the following
Bleibende Dehnung 17% Werte:Permanent elongation 17% values:
Einreißfestigkeit 23 kg/cm Zugfestigkeit 94 kg/cm*Tear strength 23 kg / cm Tensile strength 94 kg / cm *
Shore-HarteA 92 25 Brachdehnung 360 %Shore hardness A 92 25 elongation at break 360%
Stoßelastizitat 46% Bleibende Dehnung 23%Impact elasticity 46% Permanent elongation 23%
Einreißfestigkeit 23 kg/cmTear strength 23 kg / cm
Beispiel 2 Shore-Härte A 91Example 2 Shore hardness A 91
Stoßelastizitat 54 %Impact elasticity 54%
Nach den im Beispiel 1 angegebenen Versuchs- 30After the test 30 specified in Example 1
bedingungen wurden 200 g einer aus einem linearen . . Polypropylenglykoläther und Acrylnitril hergestellten Beispiel i Polyhydroxylverbindung (OH-Zahl 44; 25% Acryl- Unter den im Beispiel 1 angegebenen Bedingungen nitril) mit 36 g 1,5-Naphthylendiisocyanat und 6,2 g werden 200 g einer aus einem linearen Polyäthylen-Butandiol-1,4 umgesetzt. Das erhaltene Material hat 35 glykoläther und 20% Acrylnitril hergestellten Polyfolgende mechanische Eigenschaften: hydroxylverbindung (OH-Zahl 55) mit 60 g 1,5-Naphthylendiisocyanat und 14 g 1,4-Butandiol umZugfestigkeit 145 kg/cms gesetzt. Das erhaltene Material hat folgende Eigen-conditions were 200 g one from a linear. . Polypropylene glycol ether and acrylonitrile prepared Example i polyhydroxyl compound (OH number 44; 25% acrylic under the conditions specified in Example 1 nitrile) with 36 g of 1,5-naphthylene diisocyanate and 6.2 g, 200 g of a linear polyethylene butanediol 1.4 implemented. The material obtained has 35 glycol ether and 20% acrylonitrile, the following mechanical properties: hydroxyl compound (OH number 55) with 60 g of 1,5-naphthylene diisocyanate and 14 g of 1,4-butanediol to give a tensile strength of 145 kg / cm s . The material received has the following properties
Bruchdehnung 390 % schäften:Elongation at break 390% shafts:
Bleibende Dehnung 44 % 40 Zugfestigkeit 119 kg/cm2 Permanent elongation 44% 40 tensile strength 119 kg / cm 2
Einreißfestigkeit ^7 kg/cm Bruchdehnung 170%Tear strength ^ 7 kg / cm elongation at break 170%
^Ti f vi ?1o< Bleibende Dehnung 19%^ Ti f vi ? 1o <permanent elongation 19%
Stoßelastmtat 54% Einreißfestigkeit „ 49 kg/cmImpact load: 54% tear strength "49 kg / cm
Shore-Härte A 97Shore hardness A 97
Beispiel 3 45 Stoßelastizitat 53%Example 3 45 Resilience 53%
In 200 g einer aus einem linearen Polypropylen-In 200 g of a linear polypropylene
glykoläther und Acrylnitril erhaltenen Polyhydroxyl- Beispiel 6glycol ether and acrylonitrile obtained polyhydroxyl Example 6
verbindung (20% Acrylnitril; OH-Zahl 39) werden Unter den im Beispiel 1 angegebenen BedingungenCompound (20% acrylonitrile; OH number 39) under the conditions given in Example 1
nach dem Entwässern bei 130° C/12 mm 80 g 50 werden 200 g einer aus Äthylenglykol, 1,4-Butandiolafter dehydration at 130 ° C / 12 mm 80 g 50 are 200 g of ethylene glycol, 1,4-butanediol
4,4'-Diphenylmethandiisocyanat eingerührt. Man hält und Adipinsäure hergestellten Polyesters und 20%4,4'-Diphenylmethane diisocyanate is stirred in. One holds and adipic acid made polyester and 20%
die Temperatur etwa 20 Minuten auf 130 bis 140° C Acrylnitril erhaltenen Polyhydroxylverbindung (OH-the temperature for about 20 minutes to 130 to 140 ° C acrylonitrile obtained polyhydroxyl compound (OH-
und gibt dann 20,8 g Butandiol-1,4 hinzu. Nun wird Zahl 51) mit 60 g 1,5-Naphthylendiisocyanat undand then add 20.8 g of 1,4-butanediol. Now number 51) with 60 g of 1,5-naphthylene diisocyanate and
die homogene Schmelze in Formen gegossen. Nach 14 g Butandiol-1,4 umgesetzt. Das erhaltene Materialthe homogeneous melt poured into molds. After 14 g of 1,4-butanediol reacted. The material obtained
24stündigem Nachheizen bei 100° C wird ein Ma- 55 hat folgende Eigenschaften: terial mit den folgenden Eigenschaften erhalten: Zugfestigkeit 220 kg/cm2 After heating for 24 hours at 100 ° C., a material is obtained with the following properties: material with the following properties: tensile strength 220 kg / cm 2
„ . .. , . 1O-, , , Bruchdehnung 280%". ..,. 1O -,,, elongation at break 280%
Zugfestigkeit ^2 kg/a* Bleibende Dehnung 21 %Tensile strength ^ 2 kg / a * Permanent elongation 21%
?Γ??η^ 34? ° « Struktur 69kgabs.(4mm)? Γ ?? η ^ 34 ? ° «structure 69kg. (4mm)
Bleibende Dehnung 2% 60 shore_HärteA 98Residual elongation of 2% 60 shore _ H ärteA 98
Cm Stoßelastizität 42% Cm impact elasticity 42%
frreiweSÄ Skg/Cm Stoßelastizitat 41%fr rei w eS Ä S kg / cm impact elasticity 41%
Shore-Harte A 92Shore hardness A 92
Ein unter den gleichen Versuchsbedingungen und 65 Unter den im Beispiel 1 angegebenen BedingungenOne under the same test conditions and 65 under the conditions given in Example 1
Mengenverhältnissen erhaltenes Produkt, das aus werden 200 g einer aus einem linearen Polypropylen-Product obtained in proportions, which are made from 200 g of a linear polypropylene
einem linearen Polypropylenglykoläther (OH-Zahl glykoläther und 10% Vinylacetat erhaltenen PoIy-a linear polypropylene glycol ether (OH number glycol ether and 10% vinyl acetate obtained poly
44; ohne Acrylnitril) erhalten wurde, ist eine ver- hydroxylverbindung (OH-Zahl 56) mit 60 g 1,5-44; without acrylonitrile) is a hydroxyl compound (OH number 56) with 60 g 1.5-
Claims (1)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF36971A DE1152537B (en) | 1962-06-02 | 1962-06-02 | Process for the production of homogeneous plastics containing urethane groups |
GB1513063A GB987618A (en) | 1962-06-02 | 1963-04-17 | A process for the production of homogenous or non-porous polyurethane plastics |
FR936668A FR1364829A (en) | 1962-06-02 | 1963-05-31 | New homogeneous polyurethane plastics |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF36971A DE1152537B (en) | 1962-06-02 | 1962-06-02 | Process for the production of homogeneous plastics containing urethane groups |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1152537B true DE1152537B (en) | 1963-08-08 |
Family
ID=7096688
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF36971A Pending DE1152537B (en) | 1962-06-02 | 1962-06-02 | Process for the production of homogeneous plastics containing urethane groups |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE1152537B (en) |
GB (1) | GB987618A (en) |
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DE1253450B (en) * | 1964-06-17 | 1967-11-02 | Union Carbide Corp | Process for the production of optionally foamed polyurethanes |
US3422165A (en) * | 1964-12-08 | 1969-01-14 | Union Carbide Corp | Isocyanate and isothiocyanate compositions and polyurethanes thereof |
DE1955891A1 (en) * | 1969-11-06 | 1971-05-19 | Bayer Ag | Process for the production of foam moldings |
US4208314A (en) | 1971-08-30 | 1980-06-17 | Union Carbide Corporation | Polymer/polyols and process for production thereof |
US4282331A (en) | 1973-11-20 | 1981-08-04 | Union Carbide Corporation | Polyurethane foam prepared from a copolymer/polyol composition |
US4594366A (en) * | 1983-06-29 | 1986-06-10 | Union Carbide Corporation | Connected branched polyols and polyurethanes based thereon |
US5554662A (en) * | 1995-03-10 | 1996-09-10 | Bayer Adtiengesellschaft | Low viscosity polymer polyols a process for their production as well as the manufacture of polyurethane from materials |
EP0755968A2 (en) | 1995-07-25 | 1997-01-29 | Basf Aktiengesellschaft | Process for producing hard foam on basis of isocyanate |
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DE2915610A1 (en) | 1979-04-18 | 1980-10-30 | Bayer Ag | METHOD FOR PRODUCING MODIFIED POLYETHER POLYOLS AND THE USE THEREOF IN METHOD FOR PRODUCING POLYURETHANE PLASTICS |
DE3126436A1 (en) * | 1981-07-04 | 1983-01-20 | Basf Ag, 6700 Ludwigshafen | METHOD FOR THE PRODUCTION OF POLYURETHANE OR POLYURETHANE POLYURETE MOLDED BODIES WHICH MAY CONTAIN CELLS |
DE3436098A1 (en) * | 1984-10-02 | 1986-04-17 | Basf Ag, 6700 Ludwigshafen | METHOD FOR PRODUCING OPTIONALLY CELLED POLYURETHANE-POLYURANE MOLDED BODIES USING URETHANE AND ISOCYANURATE GROUPS CONTAINING 2,4- AND / OR 2,6-TOLUYLENE DIISOCYANATES |
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DE1253450B (en) * | 1964-06-17 | 1967-11-02 | Union Carbide Corp | Process for the production of optionally foamed polyurethanes |
US3422165A (en) * | 1964-12-08 | 1969-01-14 | Union Carbide Corp | Isocyanate and isothiocyanate compositions and polyurethanes thereof |
DE1955891A1 (en) * | 1969-11-06 | 1971-05-19 | Bayer Ag | Process for the production of foam moldings |
US4208314A (en) | 1971-08-30 | 1980-06-17 | Union Carbide Corporation | Polymer/polyols and process for production thereof |
US4282331A (en) | 1973-11-20 | 1981-08-04 | Union Carbide Corporation | Polyurethane foam prepared from a copolymer/polyol composition |
US4594366A (en) * | 1983-06-29 | 1986-06-10 | Union Carbide Corporation | Connected branched polyols and polyurethanes based thereon |
US5554662A (en) * | 1995-03-10 | 1996-09-10 | Bayer Adtiengesellschaft | Low viscosity polymer polyols a process for their production as well as the manufacture of polyurethane from materials |
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