DE863403C - Process for the production of rubber or leather-like products - Google Patents
Process for the production of rubber or leather-like productsInfo
- Publication number
- DE863403C DE863403C DEF2942D DEF0002942D DE863403C DE 863403 C DE863403 C DE 863403C DE F2942 D DEF2942 D DE F2942D DE F0002942 D DEF0002942 D DE F0002942D DE 863403 C DE863403 C DE 863403C
- Authority
- DE
- Germany
- Prior art keywords
- rubber
- sulfur
- products
- leather
- acid
- 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.)
- Expired
Links
- 229920001971 elastomer Polymers 0.000 title claims description 5
- 239000005060 rubber Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 238000004073 vulcanization Methods 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 229920000728 polyester Polymers 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 230000001588 bifunctional effect Effects 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YHGNXQAFNHCBTK-OWOJBTEDSA-N trans-3-hexenedioic acid Chemical compound OC(=O)C\C=C\CC(O)=O YHGNXQAFNHCBTK-OWOJBTEDSA-N 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 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 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- ZFCNOKDRWHSHNR-UHFFFAOYSA-N 3-[2-(2-carboxyethenyl)phenyl]prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC=C1C=CC(O)=O ZFCNOKDRWHSHNR-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 229920001875 Ebonite Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- HYJODZUSLXOFNC-UHFFFAOYSA-N [S].[Cl] Chemical compound [S].[Cl] HYJODZUSLXOFNC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229940045860 white wax Drugs 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
- C08F299/0442—Catalysts
- C08F299/0471—Other 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/83—Chemically modified polymers
- C08G18/87—Chemically modified polymers by sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
Description
Verfahren zur Herstellung von gummi- oder lederartigen Produkten Es wurde gefunden; daß gummi- bzw. lederartige Produkte dadurch erhalten werden können, daß man lineare Polyester, welche mit Hilfe von kettenverknüpfenden Mitteln auf eine Molekülgröße von oberhalb 3ooo gebracht sind und ungesättigte C-C-Bindungen enthalten, mit Schwefel oder Schwefel abgebenden Mitteln behandelt. Diese Polyester können in an sich bekannter Weise durch Veresterung von Dicarbonsäuren mit Dioxyverbindungen hergestellt werden, wobei in mehr oder minder großem Ausmaß ungesättigte Komponenten herangezogen werden. Hierfür kommen sowohl ungesättigte Säuren als auch ungesättigte Glykole in Frage. Als ungesättigte Säuren seien z. B. genannt: Maleinsäure, Itaconsäure, Citraconsäure, Dihydromuconsäure und Phenylendiacrylsäure, die auch in Form ihrer Ester verwandt werden können. An ungesättigten Glykolen seien x, q.-Butendiol, Butindiol, Butendioxäthylglykol und Dioxyäthylallylamin erwähnt.Process for the production of rubber or leather-like products Es was found; that rubber or leather-like products can thereby be obtained, that one linear polyester, which with the help of chain-linking agents have a molecular size of over 3,000 and unsaturated C-C bonds contain, treated with sulfur or sulfur-releasing agents. This polyester can in a manner known per se by esterifying dicarboxylic acids with dioxy compounds are produced, with unsaturated components to a greater or lesser extent can be used. Both unsaturated and unsaturated acids are used for this Glycols in question. As unsaturated acids are z. B. named: maleic acid, itaconic acid, Citraconic acid, dihydromuconic acid and phenylenediacrylic acid, which are also available in their form Esters can be used. Unsaturated glycols are x, q.-butenediol, butynediol, Butendioxäthylglykol and Dioxyäthylallylamine mentioned.
Als gesättigte neben ungesättigten Alkoholen bzw. neben ungesättigten Säuren anzuwendende Komponenten kommen z. B. Äthylenglykol, Butylenglykol, Adipinsäure, Bernsteinsäure, Pimelinsäure u. dgl. in Frage. Da man durch normale Veresterung von Dicarbonsäuren mit Glykolen in der Rcgel nicht über ein Molekulargewicht von etwa iooo bis 3ooo hinwegkommt und andererseits das Optimum in der Molekülgröße für die Ausgangsprodukte des vorliegenden Verfahrens erheblich darüber liegt, werden diese Polyester zunächst mit Mitteln behandelt, welche eine Verknüpfung der einzelnen Ketten untereinander bewirken. Hierfür kommen in erster Linie Düsocyanate in Frage, welche mit den Endgruppen der Polyester, seien es Carboxylgruppen, seien es Hydroxylgruppen, unter Kettenverknüpfung reagieren. Geeignete Diisocyanate sind z. B. Hexamethylendiisocyanat, Tetramethylendüsocyanat, Toluylendüsocyanat, ChlbrphenylendüsocyaAat, Hexahydrodiphenyhnethandüsocyanat u. a. Die erforderlichen ungesättigten Gruppen können natürlich alternativ oder zusätzlich auch durch die kettenverknüpfenden Mittel, also z. B. die Diisocyanate, in die Ausgangsmaterialien eingebracht werden. Als Beispiel für ungesättigte Düsocyanate seien die Umsetzungsprodukte von = Mol Butendiol oder Butindiol mit 2 Mol eines Diisocyanates genannt.As saturated in addition to unsaturated alcohols or in addition to unsaturated Acids to be used components come z. B. ethylene glycol, butylene glycol, adipic acid, Succinic acid, pimelic acid and the like. Because one through normal esterification of dicarboxylic acids with glycols generally does not have a molecular weight of about iooo to 3ooo gets over it and on the other hand the optimum in the molecular size for the starting products of the present process considerable is above, these polyesters are first treated with agents, which one Link the individual chains to one another. For this come first Line diisocyanates in question, which with the end groups of the polyester, be it carboxyl groups, be it hydroxyl groups, react with chain linkage. Suitable diisocyanates are z. B. hexamethylene diisocyanate, tetramethylene diisocyanate, toluene diisocyanate, ChlbrphenylendüsocyaAat, Hexahydrodiphenyhnethandüsocyanat and others. The necessary Unsaturated groups can of course alternatively or additionally also by the chain-linking agents, so z. B. the diisocyanates, in the starting materials be introduced. The reaction products are an example of unsaturated diisocyanates of = moles of butenediol or butynediol with 2 moles of a diisocyanate.
Die vorstehend geschilderten linearen ungesättigten Polyester stellen wachsartige bis zähfeste Massen dar. Auf jeden Fall sind sie als im wesentlichen linear aufgebaute Produkte zumindest noch leicht schmelzbar. Sie sind daher besonders geeignet zur Aufnahme von Füllstoffen sowie von Vulkanisationsmitteln, z. B. Schwefel oder schwefelabgebenden Stoffen. Als schwefelabgebender Stoff sei vor allen Dingen Chlorschwefel erwähnt. Auch die üblichen Vulkanisationsbeschleuniger können angewendet werden. Unter der Einwirkung von Schwefel bzw. schwefelabgebenden Stoffen, evtl. unter Beimischung von Vulkanisationsbeschleunigern, erleiden diese Produkte Zustandsänderungen, welche den bei der Vulkanisation von natürlichem oder synthetischem Kautschuk auftretenden Änderungen ähneln. Die erhaltenen Vulkanisate zeigen einen faktis- bzw. Leder- oder gummiartigen Charakter. Sie können für die Herstellung der verschiedenartigsten Formartikel benutzt werden. Es empfiehlt sich hierbei, die Vulkanisation unter gleichzeitiger Formgebung durchzuführen. Je nach der Zahl der ungesättigten Bindungen der angewandten Menge an Vulkanisationsmitteln und der Vulkanisationsbedingungen kann der Charakter der Vulkanisate in allen Abstufungen von Weichkautschuk bis Hartkautschuk beeinflußt werden. Beispiel i .The above-described linear unsaturated polyesters provide waxy to tough masses. In any case, they are as essentially products with a linear structure are at least easy to melt. They are therefore special suitable for absorbing fillers and vulcanizing agents, e.g. B. sulfur or sulfur-releasing substances. As a sulfur-releasing substance, above all else Mentioned sulfur chlorine. The usual vulcanization accelerators can also be used will. Under the influence of sulfur or sulfur-releasing substances, possibly when admixed with vulcanization accelerators, these products undergo changes of state, which occur during the vulcanization of natural or synthetic rubber Changes are similar. The vulcanizates obtained show a factual or leather or rubbery character. You can use for making the most diverse Molded articles can be used. It is recommended that the vulcanization under simultaneous Perform shaping. Depending on the number of unsaturated bonds applied Amount of vulcanizing agents and the vulcanization conditions can affect the character of the vulcanizates in all grades from soft rubber to hard rubber will. Example i.
a) Herstellung des Ausgangskondensates: In einem Rührgefäß mit absteigendem Kühler und Überleitungsrohr wird ein Gemisch von 365 g Adipinsäure, 72 g Dihydromuconsäure und 204,6 g Glykol im Kohlensäurestrom unter Rühren erwärmt. Bei 130 bis 14o° geht das Wasser über. Man steigert die Temperatur allmählich bis 22o° und erwärmt, nachdem die berechnete Menge Wasser übergegangen ist, noch 7 Stunden im Vakuum. Die Kondensationsdauer beträgt etwa 28 bis 3o Stunden. Es bildeten sich 118 g Wasser. Das Kondensationsprodukt ist ein weißes Wachs. Die Analyse ergibt: OH-Zahl 26,6, S-Zahl 5,5, 0/0 H20 o,2, Ausbeute 523 g. 300, g des Produktes wurden bei 12o°.unter Rühren mit 17,4 g Hexamethylendüsocyanat behandelt. Die Temperatur wird dann allmählich auf 17o° gesteigert. Das Kondensationsprodukt wird dabei sehr zähflüssig und erstarrt beim Erkalten zu einem festen Produkt. b) Vulkanisation: Eine Mischung aus ioo g des gemäß a) erhaltenen Kondensates: 3 g Schwefel, 3 g Merkaptobenzothiazol, = g Tetramethylthiuramdisulfid wurde 6o Minuten und 12o Minuten bei 4 atü vulkanisiert.a) Production of the starting condensate: In a stirred vessel with a descending A mixture of 365 g of adipic acid and 72 g of dihydromuconic acid is used for the condenser and transfer tube and 204.6 g of glycol heated in a stream of carbonic acid with stirring. Goes at 130 to 14o ° the water over. The temperature is gradually increased to 22o ° and warmed up afterwards the calculated amount of water has passed over, another 7 hours in a vacuum. The duration of condensation is about 28 to 30 hours. 118 g of water were formed. The condensation product is a white wax. The analysis shows: OH number 26.6, S number 5.5, 0/0 H20 o, 2, Yield 523g. 300 g of the product were mixed with 17.4 g of hexamethylene diisocyanate at 120 ° while stirring treated. The temperature is then gradually increased to 170 °. The condensation product becomes very viscous and solidifies to a solid product when it cools. b) Vulcanization: A mixture of 100 g of the condensate obtained according to a): 3 g Sulfur, 3 g mercaptobenzothiazole, = g tetramethylthiuram disulfide was 60 minutes and vulcanized at 4 atmospheres for 12o minutes.
Es wurden folgende Werte erhalten: Festigkeit 167 kg/cm2, Dehnung 626 0/0, Elastizität bei 2o° 38°/0, Elastizität bei 70° 53 0/0.The following values were obtained: strength 167 kg / cm2, elongation 626 0/0, elasticity at 20 ° 38 ° / 0, elasticity at 70 ° 53 0/0.
Beispiel e Ein Polyester, der nach den Angaben des Beispiels i aus 365g Adipinsäure, 43,2 g Dihydromuconsäure und igi g Glykol erhalten wurde und eine OH-Zahl von 46,1 und Säurezahl von 2,1 besitzt, wurde mit 7,7 0/0 Hexamethylendüsocyanat bei 15o bis 17o° behandelt und in dem im Beispiel i angegebenen Mischungsverhältnis vulkanisiert. Das Produkt lieferte folgende Werte: Festigkeit 143 kg/cm', Dehnung 53o 0/0, Elastizität 37 0/0.Example e A polyester made according to the information in Example i 365 g of adipic acid, 43.2 g of dihydromuconic acid and igi g of glycol was obtained and one Has an OH number of 46.1 and an acid number of 2.1, with 7.7 0/0 hexamethylene diisocyanate Treated at 15o to 17o ° and in the mixing ratio given in example i vulcanized. The product gave the following values: strength 143 kg / cm ', elongation 53o 0/0, elasticity 37 0/0.
Beispiel 3 a) Herstellung des Ausgangsmaterials: In gleicher Weise, wie in Beispiel i angegeben, wurde ein Gemisch von 409 g Glykol, 98 g Maleinsäureanhydrid und 73o g Adipinsäure verestert. Als Katalysator wurden 3 ccm konzentrierter Salzsäure und ferner eine geringe Hydrochinonmenge hinzugefügt. Die Kondensationsdauer beträgt etwa 37 Stunden. Es entstanden 216 g Wasser. Das Kondensationsprodukt ist ein gelbes 01, das beim Erkalten nach einiger Zeit erstarrt. Die Analyse ergab: 0 H-Zahl 34,3, S-Zahl 2,o, 0/0 Hz 0 0,o4, Ausbeute 1010 g. 300 g des Polyesters wurden bei 12o° mit 18,8 g Hexamethylendiisocyanat versetzt. Die Temperatur wurde dann allmählich auf 15o bis 17o° gesteigert. Die Umsetzung des Diisocyariates wurde auf der heißen Walze zu Ende geführt.Example 3 a) Preparation of the starting material: In the same way as indicated in Example i, a mixture of 409 g of glycol, 98 g of maleic anhydride and 730 g of adipic acid was esterified. 3 cc of concentrated hydrochloric acid and also a small amount of hydroquinone were added as a catalyst. The condensation time is about 37 hours. 216 g of water were formed. The condensation product is a yellow 01 which solidifies after a while when it cools down. The analysis showed: 0 H number 34.3, S number 2, 0.010 / 0 Hz 0.04, yield 1010 g. 300 g of the polyester were mixed with 18.8 g of hexamethylene diisocyanate at 120 °. The temperature was then gradually increased to 150 to 17o °. The implementation of the Diisocyariates was carried out on the hot roller to the end.
b) Vulkanisation: Das Vulkanisationsprodukt ergibt unter den im Beispiel i angegebenen Vulkanisationsbedingungen folgende Werte: Festigkeit =5 kg/cm2, Dehnung 140 0/0, Elastizität bei 20° 48 0/0, Elastizität bei 7o° 72 0/0, Härte 50° skore.b) Vulcanization: The vulcanization product results under those in the example The following values are given under the vulcanization conditions: Strength = 5 kg / cm2, elongation 140 0/0, elasticity at 20 ° 48 0/0, elasticity at 70 ° 72 0/0, hardness 50 ° score.
Beispiel 4 300 g des in Beispiel 2 beschriebenen Polyesters werden bei 12o° mit 18 g Toluylendüsocyanat behandelt. Dann wird die Temperatur allmählich auf 15o° gesteigert. Das Kondensationsprodukt wurde wie oben angegeben vulkanisiert und ergab folgende Werte: Festigkeit 22 kg/cm2, Dehnung 375 %, Elastizität bei 20° 40 0/0, Elastizität bei 70° 63 0/0, Härte 44° skore.Example 4 300 g of the polyester described in Example 2 are treated at 120 ° with 18 g of toluene diisocyanate. Then the temperature is gradually increased to 150 °. The condensation product was vulcanized as indicated above and gave the following values: strength 22 kg / cm2, elongation 375%, elasticity at 20 ° 40 ° / 0, elasticity at 70 ° 63 ° / 0, hardness 44 ° skore.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF2942D DE863403C (en) | 1944-02-15 | 1944-02-15 | Process for the production of rubber or leather-like products |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF2942D DE863403C (en) | 1944-02-15 | 1944-02-15 | Process for the production of rubber or leather-like products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE863403C true DE863403C (en) | 1953-01-19 |
Family
ID=7083590
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF2942D Expired DE863403C (en) | 1944-02-15 | 1944-02-15 | Process for the production of rubber or leather-like products |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE863403C (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1031509B (en) * | 1953-12-04 | 1958-06-04 | Ici Ltd | Improvement of the storage stability of terminal isocyanate groups containing isocyanate-modified saturated polyesters, polyester amides or polyethers |
| DE1054707B (en) * | 1954-05-07 | 1959-04-09 | Ici Ltd | Process for the production of storable and controllable crosslinkable isocyanate-modified saturated polyesters, polyesteramides and polyaethers |
| US3015636A (en) * | 1957-10-24 | 1962-01-02 | Gen Tire & Rubber Co | Sulfur curing of polyether-urethane rubbers |
| US3036042A (en) * | 1957-04-09 | 1962-05-22 | Bayer Ag | Preparation of polyurethanes |
| US3043807A (en) * | 1958-01-27 | 1962-07-10 | Goodyear Tire & Rubber | Polyurethane elastomers |
| DE1220384B (en) * | 1962-03-03 | 1966-07-07 | Bayer Ag | Use of polyurethane crosslinked with sulfur as a leather substitute |
| DE1226071B (en) * | 1963-04-05 | 1966-10-06 | Bayer Ag | Use of polyurethanes crosslinked with polyisocyanates as leather substitutes |
| EP1188780A1 (en) * | 2000-09-13 | 2002-03-20 | Rhein Chemie Rheinau GmbH | Silica gel containing rubber compounds with organic siliciumcompounds as compounding agent |
-
1944
- 1944-02-15 DE DEF2942D patent/DE863403C/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1031509B (en) * | 1953-12-04 | 1958-06-04 | Ici Ltd | Improvement of the storage stability of terminal isocyanate groups containing isocyanate-modified saturated polyesters, polyester amides or polyethers |
| DE1054707B (en) * | 1954-05-07 | 1959-04-09 | Ici Ltd | Process for the production of storable and controllable crosslinkable isocyanate-modified saturated polyesters, polyesteramides and polyaethers |
| US3036042A (en) * | 1957-04-09 | 1962-05-22 | Bayer Ag | Preparation of polyurethanes |
| US3015636A (en) * | 1957-10-24 | 1962-01-02 | Gen Tire & Rubber Co | Sulfur curing of polyether-urethane rubbers |
| US3043807A (en) * | 1958-01-27 | 1962-07-10 | Goodyear Tire & Rubber | Polyurethane elastomers |
| DE1220384B (en) * | 1962-03-03 | 1966-07-07 | Bayer Ag | Use of polyurethane crosslinked with sulfur as a leather substitute |
| DE1226071B (en) * | 1963-04-05 | 1966-10-06 | Bayer Ag | Use of polyurethanes crosslinked with polyisocyanates as leather substitutes |
| EP1188780A1 (en) * | 2000-09-13 | 2002-03-20 | Rhein Chemie Rheinau GmbH | Silica gel containing rubber compounds with organic siliciumcompounds as compounding agent |
| US6593418B2 (en) | 2000-09-13 | 2003-07-15 | Rhein Chemie Rheinau Gmbh | Silica gel-containing rubber compounds with organosilicon compounds as compounding agent |
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