DE2421820A1 - THERMAL DIMERIZATION OF ACYCLIC CONJUGATE PENTADIENES AND PROCESSING OF THE DIMERS TO TERPE RESINS - Google Patents
THERMAL DIMERIZATION OF ACYCLIC CONJUGATE PENTADIENES AND PROCESSING OF THE DIMERS TO TERPE RESINSInfo
- Publication number
- DE2421820A1 DE2421820A1 DE2421820A DE2421820A DE2421820A1 DE 2421820 A1 DE2421820 A1 DE 2421820A1 DE 2421820 A DE2421820 A DE 2421820A DE 2421820 A DE2421820 A DE 2421820A DE 2421820 A1 DE2421820 A1 DE 2421820A1
- Authority
- DE
- Germany
- Prior art keywords
- sodium
- isoprene
- sodium salt
- dimers
- acylic
- 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
- 229920005989 resin Polymers 0.000 title claims description 15
- 239000011347 resin Substances 0.000 title claims description 15
- 239000000539 dimer Substances 0.000 title claims description 13
- 238000006471 dimerization reaction Methods 0.000 title description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 32
- 229920000642 polymer Polymers 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 10
- 150000003505 terpenes Chemical class 0.000 claims description 10
- 235000007586 terpenes Nutrition 0.000 claims description 10
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 8
- 159000000000 sodium salts Chemical class 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 235000010344 sodium nitrate Nutrition 0.000 claims description 4
- 239000004317 sodium nitrate Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- XEYBHCRIKKKOSS-UHFFFAOYSA-N disodium;azanylidyneoxidanium;iron(2+);pentacyanide Chemical compound [Na+].[Na+].[Fe+2].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].[O+]#N XEYBHCRIKKKOSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940083618 sodium nitroprusside Drugs 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- LZRLOBZXVDQFSC-UHFFFAOYSA-J sodium cobalt(3+) tetranitrite Chemical compound N(=O)[O-].[Co+3].[Na+].N(=O)[O-].N(=O)[O-].N(=O)[O-] LZRLOBZXVDQFSC-UHFFFAOYSA-J 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000008366 buffered solution Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000002002 slurry Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 241000779819 Syncarpia glomulifera Species 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000001739 pinus spp. Substances 0.000 description 2
- 229940036248 turpentine Drugs 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229920003345 Elvax® Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- UATJOMSPNYCXIX-UHFFFAOYSA-N Trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UATJOMSPNYCXIX-UHFFFAOYSA-N 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 241000482268 Zea mays subsp. mays Species 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- CGOSIVYNVKVZBK-UHFFFAOYSA-K sodium cobalt(2+) trinitrite Chemical compound [Na+].[Co++].[O-]N=O.[O-]N=O.[O-]N=O CGOSIVYNVKVZBK-UHFFFAOYSA-K 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/38—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of dienes or alkynes
- C07C2/40—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of dienes or alkynes of conjugated dienes
-
- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
DR.-ING. VON KREISLEK DR.-ING. SCHDN WALD DR.-ING. TH. MEYER DR. FUES DIPL-CHEM. ALEK VON KREISLER DIPL.-CHEM. CAROLA KELLER DR.-ING. KLCPSCH DIPL-ING. SELTINGDR.-ING. FROM KREISLEK DR.-ING. SCHDN FOREST DR.-ING. TH. MEYER DR. FUES DIPL-CHEM. ALEK VON KREISLER DIPL.-CHEM. CAROLA KELLER DR.-ING. KLCPSCH DIPL-ING. SELTING
5 KÖLN 1, DEICHMANNHAU35 COLOGNE 1, DEICHMANNHAU 3
Köln, den 6. Mai 1974 AvK/AxCologne, May 6th 1974 AvK / Ax
910 Market Street, Wilmington, Delaware 19899 (U.5.A910 Market Street, Wilmington, Delaware 19899 (U.5.A
c
Thermische Dimerisierung von acy'lischen konjugiertenc
Thermal dimerization of acylic conjugates
Pentadienen und Weiterverarbeitung der Dinieren zu TerpenharzenPentadienes and processing of dining too Terpene resins
Die Erfindung betrifft thermische Dimerisierungsreaktionen von acyclischen konjugierten Pentadienen, wobei Reaktionen, die zur Bildung löslicher Polymerisate führen, verzögert werden. Die Erfindung umfaßt ferner katalytische Umsetzungen der in dieser Weise hergestellten Dimeren mit verschiedenen Monomeren in Lösung unter Bildung von synthetischen Terpenharzen.The invention relates to thermal dimerization reactions of acyclic conjugated pentadienes, with reactions leading to the formation of soluble polymers lead, be delayed. The invention also encompasses catalytic reactions of those produced in this manner Dimers with various monomers in solution to form synthetic terpene resins.
Natürliche Terpenharze werden aus Terpentin hergestellt. Die technischen Anwendungen der Terpene sind nicht im.vollen möglichen Maß ausgeschöpft worden, weil die Liefermöglichkeiten von Terpentin begrenzt und ungewiß sind. Es wurde bereits-vorgeschlagen, synthetische Terpene herzustellen, Jedoch sind viele der vorgeschlagenen Verfahren großtechnisch unbefriedigend. Sin bekanntes Verfahren zur Herstellung von synthetischen Terpenen besteht aus einer thermischen Dimerisierungsreaktion für Isopren und anschließender Polyaierisationsreaktion zwischen den bei der thermischen Heaktion gebildeten Dimeren und monoaierem Isopren. Die Polymeri-Natural terpene resins are made from turpentine. The technical uses of the terpenes are has not been used to the fullest extent possible because the availability of turpentine is limited and uncertain are. It has been suggested to make synthetic terpenes, however many have been suggested Technically unsatisfactory process. Sin well-known process for the production of synthetic Terpenes consists of a thermal dimerization reaction for isoprene and subsequent polymerization reaction between the dimers formed in the thermal heat and monoated isoprene. The polymer
40 9848/107940 9848/1079
sation kann in Lösung unter Verwendung eines Friedel-Crafts-Katalysators durchgeführt werden. Bei der thermischen Dimerisierungsreaktion fallen erhebliche Mengen eines löslichen Polymerisats neben den gewünschten Dimeren an, wodurch die Ausbeute an Dimeren verringert wird. Wenn das lösliche Polymerisat nicht von den Dimeren vor der Polymerisationsreaktion abgetrennt wixd, ist das gebildete Harz ein weniger als befriedigender Klebrigmacher für Kautschuk. Außer diesem löslichen Polymerisat werden sogenannte "popcorn"-Polymerisate in geringen Mengen während der Dimerisierung gebildet. Dieser Polymertyp kann normale Operationen stören, indem er Rohre verstopft und richtiges -Arbeiten von Ventilen verhindert. Verschiedene Inhibitoren werden zur Unterdrückung von Polymerisationsreaktionen verwendet, bei denen lösliche Polymerisate gebildet werden, jedoch erwiesen sie sich nur in begrenztem !.laße als brauchbar. Die Ergebnisse mehrerer Versuche, bei denen tert.-Butylcatechin (TBO) und der Monomethyläther von Hydrochinon (MEHQ) als Inhibitoren der thermischen Dimerisierung von 99%igeci Isopren verwendet wurden, sind in Tabelle 1 genannt. Die Versuche wurden mit Ansätzen von 500 g in einem 1-1-Reaktionsgefäß bei 150°C für eine Zeit von 6 Stunden und bei Drücken von 7-,7 bis 17^6 atü durchgeführt.Sation can be carried out in solution using a Friedel-Crafts catalyst. In the thermal dimerization reaction, considerable amounts of a soluble polymer are obtained in addition to the desired dimers, as a result of which the yield of dimers is reduced. If the soluble polymer is not separated from the dimers prior to the polymerization reaction, the resin formed is a less than satisfactory tackifier for rubber. In addition to this soluble polymer, so-called "popcorn" polymers are formed in small amounts during the dimerization. This type of polymer can interfere with normal operations by clogging pipes and preventing valves from working properly. Various inhibitors are used to suppress polymerization reactions in which soluble polymers are formed, but they have only been found to be of limited use. The results of several tests in which tert-butylcatechol (TBO) and the monomethyl ether of hydroquinone (MEHQ) were used as inhibitors of the thermal dimerization of 99% igeci isoprene are given in Table 1. The experiments were carried out with batches of 500 g in a 1-1 reaction vessel at 150 ° C. for a period of 6 hours and at pressures of 7, 7 to 17 ^ 6 atmospheres.
£09843/1079£ 09843/1079
DimeresEducated
Dimers
VerunreiniPolymers
Contaminants
von 500 g)supply
from 500 g)
MEHQTBG
MEHQ
5,00.025
5.0
KNOp
K2CO3 TBG
KNOp
K 2 CO 3
/1,0
0,250.025
/ 1.0
0.25
N-lTit.ro so
ar ylhydroxy-
lin 0,025TBC 0.025
N-lTit.ro so
ar ylhydroxy
lin 0.025
Die Verwendung von Trinitrobenzol, das als Polymerisationsinhibitor bekannt ist, ist aufgrund seiner explosiven Eigenschaften im großtechnischen Maßstab unerwünscht. Die Ergebnisse der in Tabelle 1 zusammengestellten Versuche zeigen, daß ein unerwünscht hoher Anteil an polymerer Verunreinigung gebildet wird.The use of trinitrobenzene as a polymerization inhibitor is known, is undesirable on an industrial scale because of its explosive properties. The results of the tests compiled in Table 1 show that an undesirably high Part of polymeric contamination is formed.
Gemäß der Erfindung werden acyclische konjugierte Diene in Gegenwart eines Natriumsalzes dimerisiert, das die Bildung von löslichem Polymerisat hemmt und vermindert. Vorzugsweise wird eine Lösung von Natriumnitrat, Natriumkob-altnitrit oder Natriumnitroprussid einem acyclischen konjugierten Pentadien zugesetzt, bevor die Dimerisierung stattfindet, worauf das Monomere dimerisiert Wird. Es wurde gefunden, daß durch Zusatz geringer Mengen Natriumnitrat zu einem Pentadienmonomeren, z.B. Isopren, die Bildung von löslichem Polymerisat auf ein unbedeutendes Maß vermindert wird. Gemäß der Erfindung wird das Natriumnitrat in einerAccording to the invention, acyclic conjugated dienes are dimerized in the presence of a sodium salt, which inhibits and reduces the formation of soluble polymer. Preferably a solution of sodium nitrate, Sodium cobalt nitrite or sodium nitroprusside added to an acyclic conjugated pentadiene before dimerization takes place, whereupon the monomer Is dimerized. It has been found that by adding small amounts of sodium nitrate to a pentadiene monomer, e.g. isoprene, the formation of soluble polymer is reduced to an insignificant level. According to the invention, the sodium nitrate is in a
U 0 U 0
1 Ü 7 91 night 7 9
Menge von 0,0036 bis 0,4 % als Inhibitor verwendet. Das Natriumsalz kann in wässriger oder alkoholischer Lösung zugesetzt werden. Vorteilhaft wird eine gepufferte wässrige Lösung des Natriumsalzes verwendet.Amount of 0.0036-0.4 % used as an inhibitor. The sodium salt can be added in an aqueous or alcoholic solution. A buffered aqueous solution of the sodium salt is advantageously used.
Die Ergebnisse von Versuchen zur Dimerisierung von Isopren unter den gleichen allgemeinen Bedingungen wie die in Tabelle 1 zusammengestellten Versuche, jedoch unter Hemmung der Reaktionen, die zur Bildung von löslichem-Polymerisat führen, sind in Tabelle 2 genannt.The results of attempts to dimerize isoprene under the same general conditions as the experiments compiled in Table 1, but with the inhibition of the reactions that lead to the formation of Soluble polymer lead are listed in Table 2.
Tabelle Versuch Inhibitor, Gramm Table attempt inhibitor, grams
Gebildetes Polymere Dimeres Verunreini gung (in fo von 500 g)Formed polymer dimer impurity (in fo of 500 g)
TBC H2O NapCO, NaRO2 TBC H 2 O NapCO, NaRO 2
TBC H2O ITa2COx TBC H 2 O ITa 2 CO x
NaNO2-"NaNO 2 - "
TBC H2O Na2COz NaIiO2 TBC H 2 O Na 2 COz NaIiO 2
TBC HpO Na2C0z NaEOo5 TBC HpO Na 2 C0 z NaEOo 5
TBC H2O Na2CO KCOTBC H 2 O Na 2 CO KCO
TBCTBC
2 ) 2 )
0,025 10.025 1
0,5 20.5 2
0,025 10.025 1
0,010.01
0,050.05
0,025 0,7 0,004 0,0180.025 0.7 0.004 0.018
0,05 0,050.05 0.05
0,025 20.025 2
0,5 2,00.5 2.0
0,0250.025
20 2,0 2 0 2.0
4098i 3/10794098i 3/1079
5959
6060
5252
6060
6363
0,10.1
0,20.2
0,40.4
0,30.3
0,30.3
0,50.5
Es wurde gefunden, daß Piperylen und Lösungen von Isopren und Piperylen in deaf gleichen Weise dimerisiert werden können. Die Ergebnisse von Versuchen, die unter den gleichen Bedingungen wie die in Tabelle 1 und 2 zusammengestellten Versuche durchgeführt wurden, sind in Tabelle 3 genannt. : It has been found that piperylene and solutions of isoprene and piperylene can be dimerized in the same manner. The results of tests which were carried out under the same conditions as the tests compiled in Tables 1 and 2 are given in Table 3. :
■ Tabelle 3 ■ Table 3
Versuch Inhibitor, Gramm Gebildetes Polymere Ver-Experiment inhibitor, grams of polymer formed
Dimeres unreinigung (in % von 500 g) Dimer impurity (in % of 500 g)
22 0,1 1422 0.1 14
d 3Na 0 CO 2
d 3
(42 % Isopren)
(58 Yo Pipery
len)Monomer
(42 % isoprene)
(58 Yo Pipery
len)
38 0,238 0.2
Es wurde gefunden, daß durch Polymerisation der in den Tabellen 2 und 3 genannten Dimeren mit Monomeren wie Isopren, Vinyltoluol, Styrol und α-Methylstyrol in wirtschaftlicher Weise synthetische Terpenharze gebildet werden. Polymerisationsversuche wurden in einem 1000-ml-Kolben mit Ansätzen von 600 g durchgeführt, die etwa 300 g des durch thermische Dimerisierung hergestellten Dimeren von Isopren, Monomeres, einen Priedel-Crafts-Katalysator und ein Lösungsmittel enthielten. Nach der Vermischung der Bestandteile des Ansatzes wurden die Polymerisationen etwa 2 Stunden durchgeführt. Beispiele sind in Tabelle 4 genannt.It has been found that by polymerizing the dimers mentioned in Tables 2 and 3 with monomers such as Isoprene, vinyltoluene, styrene and α-methylstyrene in synthetic terpene resins can be formed economically. Polymerization attempts were in one 1000 ml flask carried out with batches of 600 g, the approximately 300 g of the dimer of isoprene, monomer, produced by thermal dimerization Contained Priedel-Crafts catalyst and a solvent. After mixing the components of the The polymerizations were carried out for about 2 hours. Examples are given in Table 4.
4 0-9 848/107940-9 848/1079
Ausbeute
KDimeres
+ Μοηο-
pier es), % I.
yield
KDimeres
+ Μοηο-
pier it), %
Katalysa
tor, bezo
gen auf
Harz f *, - AICI3 as
Catal
gate, related
gen on
Resin
Dimeres/
Monomeresrelationship
Dimers /
Monomer
suchs-
harzVer
search-
resin
Temp.
0GBeakt,
Temp.
0 G
styrolstyrene
7Ο/3Ο7Ο / 3Ο
8686
2525th
2,52.5
Ausgewählte physikalische Eigenschaften der synthetischen Terpenharze, die durch die in Tabelle 4 zusammengestellten Reaktionen hergestellt wurden, sind nachstehend in Tabelle 5·. genannt.Selected physical properties of the synthetic terpene resins determined by those listed in Table 4 Reactions prepared are shown in Table 5 below. called.
409848/1 079409848/1 079
Testharz " 15 16 17 18 19 20 21 22 23Test resin "15 16 17 18 19 20 21 22 23
ErweichungsOunkt (Ring und Kugel),Softening point (ring and ball),
σ0 . " 109 115 115 117 115 127 135 124 107 σ 0. "109 115 115 117 115 127 135 124 107
Gardner-Farbzahl 2- 2+ 2 2 2+2 3 1+ 2Gardner color number 2- 2+ 2 2 2 + 2 3 1+ 2
Methylcyclohexan-Misch-Anilin- .Methylcyclohexane-mixed-aniline-.
£ punkt, 0C . '84 77 82 80 86 93 60 51 59£ point, 0 C. '84 77 82 80 86 93 60 51 59
% Polyken-Klebfestigkeit (50 # Harz/ % Polyken Adhesive Strength (50 # resin /
50 '/ο Naturkautschuk), g ,. 900 1500 1350 1540 1380 950 1660 1750 154050 '/ ο natural rubber), g,. 900 1500 1350 1540 1380 950 1660 1750 1540
"~- Diacetonalkohol-Trübungspunkt, 0C 60 43' 56 54 61 72 27 16 26 "^"~ - Diacetone Alcohol Cloud Point, 0 C 60 43 '56 54 61 72 27 16 26" ^
I^ Trübungspunkt, 0CI ^ cloud point, 0 C
Heißschmelztest: 60 % Ρ.εHot melt test: 60 % Ρ.ε
wachs/20 % Äthylenvinylacetat^Vwax / 20 % ethylene vinyl acetate ^ V
20 io Harz · 200 69 69 69 69 12320 io resin 200 69 69 69 69 123
50 % Wachs/25 % Äthylenvinyl-50% wax / 25 % ethylene vinyl
acetat/25 % Harz 70 71 69acetate / 25 % resin 70 71 69
Viskosität einer 70#igen Lösung . ·Viscosity of a 70 # solution. ·
in Toluol, Stokes 12,8 8,1 9,1 10,8 11,5 20,4in toluene, Stokes 12.8 8.1 9.1 10.8 11.5 20.4
x^"E x ^ "E
Elvax", Hersteller E.I. du Pont de Nemours & Co. 1^Elvax ", manufacturer EI du Pont de Nemours & Co. 1 ^
.NJ CD.NJ CD
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35865273A | 1973-05-09 | 1973-05-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2421820A1 true DE2421820A1 (en) | 1974-11-28 |
Family
ID=23410515
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2421820A Pending DE2421820A1 (en) | 1973-05-09 | 1974-05-06 | THERMAL DIMERIZATION OF ACYCLIC CONJUGATE PENTADIENES AND PROCESSING OF THE DIMERS TO TERPE RESINS |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5018405A (en) |
| AU (1) | AU6872074A (en) |
| BE (1) | BE814253A (en) |
| BR (1) | BR7403737D0 (en) |
| DE (1) | DE2421820A1 (en) |
| ES (1) | ES426075A1 (en) |
| FR (1) | FR2237865A1 (en) |
| IT (1) | IT1012186B (en) |
| NL (1) | NL7406086A (en) |
| ZA (1) | ZA742964B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4973787A (en) * | 1989-09-05 | 1990-11-27 | The Goodyear Tire & Rubber Company | Process for the thermal dimerization of isoprene |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3045229C2 (en) * | 1980-12-01 | 1982-12-02 | Deutsche Texaco Ag, 2000 Hamburg | Process for the production of vinylcyclohexene |
| EP0969074B1 (en) * | 1997-03-11 | 2006-05-10 | Nippon Zeon Co., Ltd. | Process for preparing purified conjugated diene |
-
1974
- 1974-04-25 FR FR7414498A patent/FR2237865A1/en not_active Withdrawn
- 1974-04-26 BE BE143673A patent/BE814253A/en unknown
- 1974-05-06 DE DE2421820A patent/DE2421820A1/en active Pending
- 1974-05-07 NL NL7406086A patent/NL7406086A/xx unknown
- 1974-05-08 AU AU68720/74A patent/AU6872074A/en not_active Expired
- 1974-05-08 ES ES426075A patent/ES426075A1/en not_active Expired
- 1974-05-08 IT IT22469/74A patent/IT1012186B/en active
- 1974-05-08 BR BR3737/74A patent/BR7403737D0/en unknown
- 1974-05-09 JP JP49050779A patent/JPS5018405A/ja active Pending
- 1974-05-09 ZA ZA00742964A patent/ZA742964B/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4973787A (en) * | 1989-09-05 | 1990-11-27 | The Goodyear Tire & Rubber Company | Process for the thermal dimerization of isoprene |
Also Published As
| Publication number | Publication date |
|---|---|
| AU6872074A (en) | 1975-11-13 |
| ZA742964B (en) | 1975-05-28 |
| IT1012186B (en) | 1977-03-10 |
| NL7406086A (en) | 1974-11-12 |
| FR2237865A1 (en) | 1975-02-14 |
| BE814253A (en) | 1974-08-16 |
| ES426075A1 (en) | 1976-07-01 |
| BR7403737D0 (en) | 1974-12-03 |
| JPS5018405A (en) | 1975-02-26 |
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