DE2434966A1 - O, O, O ', O'-TETRAALKYL-SUBSTITUTED BISCYCLOHEXANOLS - Google Patents
O, O, O ', O'-TETRAALKYL-SUBSTITUTED BISCYCLOHEXANOLSInfo
- Publication number
- DE2434966A1 DE2434966A1 DE19742434966 DE2434966A DE2434966A1 DE 2434966 A1 DE2434966 A1 DE 2434966A1 DE 19742434966 DE19742434966 DE 19742434966 DE 2434966 A DE2434966 A DE 2434966A DE 2434966 A1 DE2434966 A1 DE 2434966A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- dimethyl
- hydroxycyclohexyl
- carbon atoms
- biscyclohexanols
- 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
-
- 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
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
- C08G63/553—Acids or hydroxy compounds containing cycloaliphatic rings, e.g. Diels-Alder adducts
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
Zentralbereich Patente. Marken und LizenzenCentral Patents Department. Trademarks and licenses
1 8. Juli 19741 July 8, 1974
o.o.o1,o'-1etraalkylsubstituierte Biscyclohexanole ooo 1 , o'-1etraalkyl substituted biscyclohexanols
Gegenstand der Erfindung sind neue Biscyclohexanole der Formel (1)The invention relates to new biscyclohexanols of the formula (1)
(D(D
in derin the
R1 bis R1, gleiche oder ungleiche Alkyl subs tituent en mit 1 bis 3 C-Atomen undR 1 to R 1 , identical or different alkyl subs tituent s with 1 to 3 carbon atoms and
X eine Einfachbindung, einen divalenten aliphatischen verzweigten oder unverzweigten Rest mit 1 bis 10 C-Atomen, einen divalenten cycloaliphatischen Rest mit 5 bis 15 C-Atomen, einen divalenten aliphatischen verzweigten oder unverzweigten Rest mit aromatischen oder cycloaliphatischen Substituenten, der insgesamt 6 bis 15 C-Atome enthält, oderX is a single bond, a divalent aliphatic bond branched or unbranched radical with 1 to 10 carbon atoms, a divalent cycloaliphatic Remainder with 5 to 15 carbon atoms, a divalent aliphatic branched one or unbranched radical with aromatic or cycloaliphatic substituents, the total Contains 6 to 15 carbon atoms, or
bedeuten.mean.
Gegenstand der Erfindung ist weiterhin ein Verfahren zur Herstellung von Biscyclohexanolen der Formel (1) durchThe invention furthermore relates to a process for the preparation of biscyclohexanols of the formula (1)
Le A 15 873Le A15 873
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•β• β
Hydrierung von Bisphenolen der Formel (2)Hydrogenation of bisphenols of formula (2)
(2)(2)
in der R1 bis R2, und X dieselbe Bedeutung haben wie in Formel (1).in which R 1 to R 2 and X have the same meaning as in formula (1).
Biscyclohexanole der allgemeinen Formel (1) sind beispielsweise: Biscyclohexanols of the general formula (1) are for example:
Bis-(3i5-dimethyl-4-hydroxycyclohexyl),
Bis-(5* 5-dimethyl-4-hydroxycyclohexyl)-methan,
1,1-Bis-(3* 5-dimethyl-4-hydroxycyclohexyl)-äthan,
1,1-Bis-(3,5-dimethyl-4-hydroxycyclohexyl)-propan,
2,2-Bis-(3*5-dimethyl-4-hydroxycyclohexyl)-propan,
2,2-Bis-(3»5-dimethyl-4-hydroxycyclohexyl)-butan, 2,4-Bis-(3j S-dimethyl-^-hydroxycyclohexyl)-2-methylbutan,
2,4-Bis-Ο* S-dimethyl-^-hydroxycyclohexyl)-butan,
3,3-Bis-(3i5-dimethyl-4-hydroxycyclohexyl)-pentan,
3* 3-Bis-(3* 5-dimethyl-4-hydroxycyclohexyl)-hexan,
4,4-Bis-(3i 5-dimethyl-4-hydroxycyclohexyl)-heptan,
2,2-Bis-(3* 5-dimethyl-4-hydroxycyclohexyl)-octan,
2,2-Bis-(3,5-dimethyl-4-hydroxycyclohexyl)-nonan,
2,2-Bis-(3j 5-dimethyl-4-hydroxycyclohexyl)-decan,
1,1-Bis-(3*5-dimethyl-4-hydroxycyclohexyl)-cyclohexan,
Bis-(3*5-dimethyl-4-hydroxycyclohexyl)-cyclohexylmethan,
Bis- (3* 5-diäthyl-4-hydroxycyclohexyl) -cyclohexylmethan,
1,4-Bis-(3,5-dimethyl-4-hydroxycyclohexyr) -cyclohexan,
2,2-Bis-(3* 5-diäthyl-4-hydroxycyclohexyl)-propan,
Bis-(3i 5-diisopropyl-4-hydroxycyclohexyl)-methan,
2,2-Bis- O-methyl^-isopropyl^-hydroxycyclohexyl) -propan,
α, α1 -Bis-(3*5-dimethyl-4-hydroxycyclohexyl)-p-diisopropylbenzol,
oC,ot!-Bis-(3i5-dimethyl-4-hydroxycyclohexyl)-m-diisopropylbenzol,
1,1 -Bis- (3,5-dimethyl-4-hydroxycyclohexyl) cyclododecan
Bis- (3j 5-dimethyl-4-hydroxycyclohexyl) -phenylmethan.Bis (3i5-dimethyl-4-hydroxycyclohexyl),
Bis (5 * 5-dimethyl-4-hydroxycyclohexyl) methane,
1,1-bis- (3 * 5-dimethyl-4-hydroxycyclohexyl) -ethane, 1,1-bis- (3,5-dimethyl-4-hydroxycyclohexyl) -propane, 2,2-bis- (3 * 5 -dimethyl-4-hydroxycyclohexyl) propane, 2,2-bis- (3 »5-dimethyl-4-hydroxycyclohexyl) -butane, 2,4-bis- (3j S-dimethyl- ^ - hydroxycyclohexyl) -2-methylbutane , 2,4-bis- Ο * S-dimethyl- ^ - hydroxycyclohexyl) -butane, 3,3-bis- (3i5-dimethyl-4-hydroxycyclohexyl) -pentane, 3 * 3-bis- (3 * 5-dimethyl -4-hydroxycyclohexyl) -hexane, 4,4-bis- (3i 5-dimethyl-4-hydroxycyclohexyl) -heptane, 2,2-bis- (3 * 5-dimethyl-4-hydroxycyclohexyl) -octane, 2.2 -Bis- (3,5-dimethyl-4-hydroxycyclohexyl) -nonane, 2,2-bis- (3j 5-dimethyl-4-hydroxycyclohexyl) -decane, 1,1-bis- (3 * 5-dimethyl-4 -hydroxycyclohexyl) -cyclohexane, bis- (3 * 5-dimethyl-4-hydroxycyclohexyl) -cyclohexylmethane, bis- (3 * 5-diethyl-4-hydroxycyclohexyl) -cyclohexylmethane, 1,4-bis- (3,5-dimethyl -4-hydroxycyclohexyr) -cyclohexane, 2,2-bis- (3 * 5-diethyl-4-hydroxycyclohexyl) -propane, bis- (3i 5-diisopropyl-4-hydroxycyclohexyl) -methane, 2,2-bis-O -methyl ^ -isopropyl ^ -hydroxycyclohexyl) -pr opane, α, α 1 -bis- (3 * 5-dimethyl-4-hydroxycyclohexyl) -p-diisopropylbenzene, oC, ot ! -Bis- (3i5-dimethyl-4-hydroxycyclohexyl) -m-diisopropylbenzene, 1,1 -Bis- (3,5-dimethyl-4-hydroxycyclohexyl) cyclododecane, bis- (3j 5-dimethyl-4-hydroxycyclohexyl) -phenylmethane.
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B09886/1110B09886 / 1110
Bevorzugt sind Biscyclohexanole der allgemeinen Formel (1), in denen die Substituenten R1, R2, R-, und R^ M ethyl gruppen sind.Biscyclohexanols of the general formula (1) in which the substituents R 1 , R 2 , R-, and R ^ M are ethyl groups are preferred.
Aus dieser Gruppe besonders bevorzugt sind:Particularly preferred from this group are:
1,1-Bis-(3>5-dimethyl-4-hydroxycyclohexyl)-äthan, Bis-(3,5-dimethyl-4-hydroxycyclohexyl)-methan, 2,4-Bis-(3,5-dimethyl-4-hydroxycyclohexyl)-2-methylbutan, 2,2-Bis-(3* 5-dimethyl-4-hydroxycyclohexyl)-propan, 1,1-Bis-(3i5-dimethyl-4-hydroxycyclohexyl)-cyclohexan, cf, oc1 -Bis- (3,5-dimethyl-4-hydroxycyclohexyl) -p-diisopropylbenzol,1,1-bis- (3> 5-dimethyl-4-hydroxycyclohexyl) -ethane, bis- (3,5-dimethyl-4-hydroxycyclohexyl) -methane, 2,4-bis- (3,5-dimethyl-4 -hydroxycyclohexyl) -2-methylbutane, 2,2-bis- (3 * 5-dimethyl-4-hydroxycyclohexyl) -propane, 1,1-bis- (3i5-dimethyl-4-hydroxycyclohexyl) -cyclohexane, cf, oc 1 -Bis- (3,5-dimethyl-4-hydroxycyclohexyl) -p-diisopropylbenzene,
Die Biscyclohexanole der Formel (1) sind für die Herstellung von härtbaren Polyestermassen von großer Bedeutung. Aus Polyestern auf Basis dieser Biscyclohexanole" und ungesättigten Säuren, wie Maleinsäure oder Fumarsäure, und daran anpolymerisierbaren Monomeren, wie z. B. Styrol, lassen sich nämlich zu Überzügen und Formteilen mit außerordentlich hoher chemischer Beständigkeit aushärtbare Massen herstellen, wie sie bislang nicht bekannt waren.The biscyclohexanols of the formula (1) are of great importance for the production of curable polyester compositions. Made of polyester based on these biscyclohexanols "and unsaturated acids, such as maleic acid or fumaric acid, and which can be polymerized onto them Monomers, such as. B. styrene, namely can be coatings and moldings with extremely high chemical Produce permanent curable masses, as they were not previously known.
Die Herstellung der ο,ο,ο1,o'-Tetraalkyldicyclohexanole der Formel (1) erfolgt erfindungsgemäß durch katalytische Hydrierung der entsprechenden ο,ο,ο',o'-Tetraalkylbisphenole der Formel (2) nach an sich bekannten Methoden in Gegenwart von Hydrierkatalysatoren bei höherer Temperatur und höherem Wasserstoff druck.The ο, ο, ο 1 , o'-tetraalkyldicyclohexanols of the formula (1) are prepared according to the invention by catalytic hydrogenation of the corresponding ο, ο, ο ', o'-tetraalkylbisphenols of the formula (2) by methods known per se in the presence of Hydrogenation catalysts at higher temperature and higher hydrogen pressure.
Als Katalysatoren sind die bekannten Hydrierkatalysatoren geeignet, die üblicherweise für die Kernhydrierung von aromatischen Verbindungen infrage kommen, vor allem solche, die als wirksamen Bestandteil Edelmetalle oder andere Metalle der 8. Gruppe des Periodensystems, insbesondere Platin, Ruthenium, Nickel und Kobalt, enthalten. Besonders geeignet sind Nickelkatalysatoren in Form von Skelett-, Träger- oder Mischkatalysatoren, z.B. Raney-Nickel, Nickel-Kieselgur, Nickel-Chromit-Katalysatoren, die als Promotoren noch andere Bestandteile,The known hydrogenation catalysts are suitable as catalysts, which are usually suitable for the nuclear hydrogenation of aromatic compounds, especially those that are active ingredient precious metals or other metals of the 8th group of the periodic table, especially platinum, ruthenium, Nickel and cobalt. Nickel catalysts in the form of skeletal, supported or mixed catalysts are particularly suitable, e.g. Raney nickel, nickel diatomaceous earth, nickel chromite catalysts, which, as promoters, have other components,
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wie Al, Mg, Th, Zn, Ba, Cu, enthalten können.such as Al, Mg, Th, Zn, Ba, Cu, may contain.
Zweckmäßigerweise arbeitet man bei Temperaturen oberhalb etwa 1200C und Drucken oberhalb etwa 50 bar, insbesondere bei Temperaturen zwischen etwa 1^O0C und etwa 2200C und Drucken zwischen etwa 100 und 500 bar.It is expedient to work at temperatures above approximately 120 ° C. and pressures above approximately 50 bar, in particular at temperatures between approximately 1 ^ O ° C. and approximately 220 ° C. and pressures between approximately 100 and 500 bar.
Die Tetraalkylbiscyclohexanole entstehen dabei in ausgezeichneten Ausbeuten und meist solcher Reinheit, daß ihre unmittelbare Verwendung, z.B. für die Herstellung härtbarer Formmassen, ohne weitere Reinigung möglich ist, was ein von phenolischen OH-Gruppen weitgehend freies Produkt voraussetzt. Eine solch glatte Hydrierung tetrasubstituierter Bisphenole war nicht zu erwarten, da die Hydrierung von Aromaten erfahrungsgemäß durch mehrfache Substitution erheblich erschwert wird.The tetraalkyl biscyclohexanols are formed in excellent Yields and mostly of such purity that their immediate use, e.g. for the production of curable molding compounds, is possible without further purification, which requires a product largely free of phenolic OH groups. One Such a smooth hydrogenation of tetra-substituted bisphenols was not to be expected, since experience has shown that aromatics are hydrogenated is made considerably more difficult by multiple substitutions.
2000 g 2,2-Bis-(3,5-dimethyl-4-hydroxyphenyl)-propan werden in einem Rührautoklaven zusammen mit 28 g eines reduzierten Ni-Cr-Al-Cu-Katalysators bei 2000C unter einem Wasserstoffdruck von 18O bis 280 bar so lange gerührt, bis die Wasserstoffaufnähme abgeklungen ist, was etwa I80 Minuten in Anspruch nimmt. Nach dem Abkühlen und Entspannen wird das Reaktionsprodukt in Dioxan aufgenommen und durch Filtration vom Katalysator getrennt.2000 g of 2,2-bis- (3,5-dimethyl-4-hydroxyphenyl) -propane are in a stirred autoclave together with 28 g of a reduced Ni-Cr-Al-Cu catalyst at 200 0 C under a hydrogen pressure of 180 to Stirred at 280 bar until the hydrogen uptake has subsided, which takes about 180 minutes. After cooling and letting down the pressure, the reaction product is taken up in dioxane and separated from the catalyst by filtration.
Nach dem Einengen der Lösung bleiben 2050 g farbloses 2,2-Bis-(3j 5-dimethyl-4-hydroxycyclohexyl)-propan zurück.After concentrating the solution, 2050 g of colorless 2,2-bis- (3j 5-dimethyl-4-hydroxycyclohexyl) propane back.
Ausbeute: 98,5 % der Theorie phenolisches OH: 0,01 % Yield: 98.5 % of theory phenolic OH: 0.01 %
Sauerstoff: 10,8 # (berechnet: 10,8 %) Oxygen: 10.8 # (calculated: 10.8 %)
Kp1 0: 185 bis 188°CKp 1 0: 185 to 188 ° C
Erweichungspunkt: 145 bis 184°CSoftening point: 145 to 184 ° C
Führt man die Hydrierung in Gegenwart von 40 g Raney-Nickel bei 190 bis 2000C unter Drucken zwischen I70 und 270 bar durch, soCarrying out the hydrogenation in the presence of 40 g Raney nickel at 190 to 200 0 C under pressures between 270 bar and I70 through, so
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erhält man 2025 g 2i2~Bis=(3i5=dimethyl~4-hydroxycyclohexyl)-propan. 2025 g of 2 i 2 bis = (3 i 5 = dimethyl 4-hydroxycyclohexyl) propane are obtained.
Ausbeute: 97*2 % der TheorieYield: 97 * 2 % of theory
phenolisches OH; 0,05 % phenolic OH; 0.05 %
Sauerstoff: 11,0 % (berechnet; 10,8 Ji) .Oxygen: 11.0 % (calculated; 10.8 Ji).
99 g Bis-(3,5-dimethyl-4-hydroxyphenyl)-methan werden in einem Schüttelautoklaven in Gegenwart von 2,5 g eines reduzierten Ni-Cr-Al-Cu-Katalysators bei 16O bis 1700C unter einem Wasserstoffdruck von 200 bis 280 bar bis zur Beendigung der Wasserstoffaufnahme geschüttelt (Dauer: 145 Minuten). Das Reaktionsprodukt wird in Methanol aufgenommen, filtriert und eingeengt. Man erhält 99 g Bis-(3,5-dimethyl-4-hydroxycyclohexyl)-methan. Ausbeute: 95*6 % der Theorie99 g of bis (3,5-dimethyl-4-hydroxyphenyl) methane are in a shaking autoclave in the presence of 2.5 g of a reduced Ni-Cr-Al-Cu catalyst at 160 to 170 0 C under a hydrogen pressure of 200 Shaken up to 280 bar until the hydrogen uptake ceases (duration: 145 minutes). The reaction product is taken up in methanol, filtered and concentrated. 99 g of bis (3,5-dimethyl-4-hydroxycyclohexyl) methane are obtained. Yield: 95 * 6 % of theory
phenolisches OH: 0,04 % phenolic OH: 0.04 %
OH-Zahl: 412 (berechnet: 419)OH number: 412 (calculated: 419)
Kp: 140 bis 142°C / 0,1 TorrBp: 140 to 142 ° C / 0.1 Torr
Erweichungspunkt: 129 bis 157°C.Softening point: 129 to 157 ° C.
100 g of,oc'-BiS-(J,5-dimethyl-4-hydroxyphenyl)-p-diisopropylbenzol werden, wie in Beispiel 2 beschrieben, hydriert. Man erhält 97,5 g of,oc!-Bis-(3>5-dimethyl-4-hydroxycyclohexyl)-pdiisopropylbenzol. 100 g of, oc'-BiS- (J, 5-dimethyl-4-hydroxyphenyl) -p-diisopropylbenzene are, as described in Example 2, hydrogenated. One receives 97.5 g of, oc ! -Bis- (3> 5-dimethyl-4-hydroxycyclohexyl) -pdiisopropylbenzene.
Ausbeute: 94,6 % der TheorieYield: 94.6 % of theory
phenolisches OH: 0,1 % phenolic OH: 0.1 %
Sauerstoff: 7,8 % (berechnet: 7,7 %) Oxygen: 7.8 % (calculated: 7.7 %)
Kp: 215°C / 0,2 TorrBp: 215 ° C / 0.2 Torr
Erweichungspunkt: 70 bis 74°C.Softening point: 70 to 74 ° C.
100 g 1,1-Bis-(3,5-dimethyl-4-hydroxyphenyl)-cyclohexan werden in Gegenwart von 7 g eines reduzierten Ni-Cr-Al-Cu-Katalysators100 g of 1,1-bis (3,5-dimethyl-4-hydroxyphenyl) -cyclohexane become in the presence of 7 g of a reduced Ni-Cr-Al-Cu catalyst
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bei 200°C und 18O bis 280°C entsprechend Beispiel 1 hydriert. Man erhält das 1,1-Bis-(3i5-dimethyl-4-hydroxycyclohexyl)-cyclohexan. hydrogenated at 200 ° C and 180 to 280 ° C according to Example 1. The 1,1-bis- (35-dimethyl-4-hydroxycyclohexyl) -cyclohexane is obtained.
Ausbeute: 96,8 % der Theorie
phenolisches OH: 0,04 %
OH-Zahl: 325 (berechnet: 333)
Kp: 170°C / 0,01 TorrYield: 96.8 % of theory phenolic OH: 0.04 %
OH number: 325 (calculated: 333) Kp: 170 ° C / 0.01 Torr
Erweichungspunkt: 126 bis 131°C.Softening point: 126 to 131 ° C.
991 g 2,4-Bis-(3,5-dimethyl-4-hydroxyphenyl)-2-methylbutan
werden in Gegenwart eines vorher mit Wasserstoff reduzierten Ni-Cr-Zn-Ba-Katalysators bei 2000C unter einem Wasserstoffdruck
von 200 bis 30° Da^ so lange gerührt, bis die Wasserstoffaufnahme
beendet ist. Das Reaktionsprodukt wird in Äthanol aufgenommen, filtriert und destilliert. Man erhält 9^3 g 2,4-Bis-(3*
S-dimethyl-^-hydroxycyclohexyl)-2-methylbutan.
Ausbeute: 92 % der Theorie phenolisches OH: 0,04 %
Kp: 169 bis 175°C / 0,2 Torr.991 g of 2,4-bis (3,5-dimethyl-4-hydroxyphenyl) -2-methylbutane are in the presence of a Ni-Cr-Zn-Ba catalyst previously reduced with hydrogen at 200 ° C. under a hydrogen pressure of 200 to 30 ° Da ^ stirred until the hydrogen uptake has ended. The reaction product is taken up in ethanol, filtered and distilled. 9 ^ 3 g of 2,4-bis- (3 * S-dimethyl - ^ - hydroxycyclohexyl) -2-methylbutane are obtained. Yield: 92 % of theory phenolic OH: 0.04 %
Bp: 169 to 175 ° C / 0.2 Torr.
Die in dem nachfolgenden Beispiel angeführten Teile bedeuten - falls nichts anderes angegeben - Gewichtsteile. Die für die Durchführung des Beispiels verwendete Polyestermasse besitzt folgende Zusammensetzung:The parts listed in the example below are parts by weight, unless otherwise stated. The for the The polyester mass used to carry out the example has the following composition:
50 Teile ungesättigter Polyester, hergestellt nach üblichen Verfahren durch Polykondensation unter Stickstoffatmosphäre bei etwa 2000C aus 171*6 Teilen Maleinsäureanhydrid und 54-3,9 Teilen 2,2-Bis-(3,5-dimethyl-4-hydroxycyclo-50 parts of unsaturated polyester prepared by conventional methods by polycondensation under nitrogen atmosphere at about 200 0 C of 171 * 6 parts of maleic anhydride and 54 to 3.9 parts of 2,2-bis (3,5-dimethyl-4-hydroxycyclo-
hexyl)-propan Säurezahl (DIN 53 042): <20hexyl) propane acid number (DIN 53 042): <20
50 Teile Styrol
0,005 Teile Hydrochinon.50 parts of styrene
0.005 part hydroquinone.
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100 g der vorgenannten ungesättigten Polyestermasse werden mit100 g of the aforementioned unsaturated polyester mass are with
2 g Benzoylperoxid versetzt. Die Masse wird zwischen zwei mit Trennmitteln versehenen Glasplatten, die durch Dichtungsstreifen in einer Distanz von 2 cm gehalten werden, gegossen und2 g of benzoyl peroxide are added. The crowd is between two with Glass plates provided with separating means, which are held at a distance of 2 cm by sealing strips, are poured and
3 Stunden bei 75°C gehärtet. Anschließend wird 15 Stunden bei 1000C getempert. Nach dem Entformen werden aus der so hergestellten Platte Prüfkörper mit den Abmessungen 25 χ 40 χ 2 mm hergestellt.Cured for 3 hours at 75 ° C. Subsequently annealed 15 hours at 100 0 C. After removal from the mold, test specimens with dimensions of 25 × 40 × 2 mm are produced from the plate produced in this way.
Die Prüfkörper werden in einem Druckautoklaven längere Zeit der Einwirkung von 1100C und 120°C heißem, luftfreiem wassei dampf ausgesetzt. Nach 63 Tagen in 1100C heißem Wasserdampf ist das Harz noch einwandfrei. Bei Beanspruchung durch 120 C heißem Wasserdampf zeigen die Platten selbst nach 21 Tagen noch keinerlei Angriff.The test specimens are in a pressure autoclave longer time of exposure of 110 0 C and 120 ° C hot, air-free wassei exposed to steam. After 63 days in hot steam at 110 ° C., the resin is still flawless. When exposed to steam at 120 C, the panels still show no attack, even after 21 days.
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Claims (4)
CH,I.
CH,
R2 HO - // VXK 7 N > -OH
R 2
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742434966 DE2434966A1 (en) | 1974-07-19 | 1974-07-19 | O, O, O ', O'-TETRAALKYL-SUBSTITUTED BISCYCLOHEXANOLS |
| NL7508519A NL7508519A (en) | 1974-07-19 | 1975-07-16 | PROCESS FOR PREPARING SUBSTITUTED BISCYCLOHEXANOLS. |
| ES439537A ES439537A1 (en) | 1974-07-19 | 1975-07-17 | Substituted biscyclohexanols |
| BE158376A BE831458A (en) | 1974-07-19 | 1975-07-17 | BIS-CYCLOHEXANOLS 0,0,0 ', 0'-TETRALCOYL-SUBSTITUTES |
| AT554075A ATA554075A (en) | 1974-07-19 | 1975-07-17 | PROCESS FOR MANUFACTURING BISCYCLOHEXANOLS |
| JP8674475A JPS5134133A (en) | 1974-07-19 | 1975-07-17 | CHIKANBISUSHIKUROHEKISANOORUNO SEIZOHOHOHO |
| GB3023775A GB1458657A (en) | 1974-07-19 | 1975-07-18 | Substituted biscyclohexanols |
| FR7522570A FR2278665A1 (en) | 1974-07-19 | 1975-07-18 | BIS-CYCLOHEXANOLS O, O, O ', O'-TETRALCOYL-SUBSTITUTES AND THEIR USE IN PARTICULAR FOR THE MANUFACTURE OF HARDENABLE POLYESTER MASSES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742434966 DE2434966A1 (en) | 1974-07-19 | 1974-07-19 | O, O, O ', O'-TETRAALKYL-SUBSTITUTED BISCYCLOHEXANOLS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2434966A1 true DE2434966A1 (en) | 1976-02-05 |
Family
ID=5921072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742434966 Pending DE2434966A1 (en) | 1974-07-19 | 1974-07-19 | O, O, O ', O'-TETRAALKYL-SUBSTITUTED BISCYCLOHEXANOLS |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5134133A (en) |
| AT (1) | ATA554075A (en) |
| BE (1) | BE831458A (en) |
| DE (1) | DE2434966A1 (en) |
| ES (1) | ES439537A1 (en) |
| FR (1) | FR2278665A1 (en) |
| GB (1) | GB1458657A (en) |
| NL (1) | NL7508519A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0368604A2 (en) * | 1988-11-09 | 1990-05-16 | Chisso Corporation | New diamino and dinitro compounds and a process for preparing the diamino compounds |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH072660B2 (en) * | 1986-05-29 | 1995-01-18 | 三井石油化学工業株式会社 | Novel biscyclohexanols |
| JPH072659B2 (en) * | 1986-05-29 | 1995-01-18 | 三井石油化学工業株式会社 | Novel biscyclohexanols |
-
1974
- 1974-07-19 DE DE19742434966 patent/DE2434966A1/en active Pending
-
1975
- 1975-07-16 NL NL7508519A patent/NL7508519A/en unknown
- 1975-07-17 ES ES439537A patent/ES439537A1/en not_active Expired
- 1975-07-17 AT AT554075A patent/ATA554075A/en not_active Application Discontinuation
- 1975-07-17 JP JP8674475A patent/JPS5134133A/en active Pending
- 1975-07-17 BE BE158376A patent/BE831458A/en unknown
- 1975-07-18 GB GB3023775A patent/GB1458657A/en not_active Expired
- 1975-07-18 FR FR7522570A patent/FR2278665A1/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0368604A2 (en) * | 1988-11-09 | 1990-05-16 | Chisso Corporation | New diamino and dinitro compounds and a process for preparing the diamino compounds |
| EP0368604A3 (en) * | 1988-11-09 | 1991-04-17 | Chisso Corporation | New diamino and dinitro compounds and a process for preparing the diamino compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2278665B1 (en) | 1979-05-11 |
| ATA554075A (en) | 1977-02-15 |
| ES439537A1 (en) | 1977-02-16 |
| BE831458A (en) | 1976-01-19 |
| NL7508519A (en) | 1976-01-21 |
| GB1458657A (en) | 1976-12-15 |
| FR2278665A1 (en) | 1976-02-13 |
| JPS5134133A (en) | 1976-03-23 |
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