SE181098C1 - - Google Patents
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- Publication number
- SE181098C1 SE181098C1 SE181098DA SE181098C1 SE 181098 C1 SE181098 C1 SE 181098C1 SE 181098D A SE181098D A SE 181098DA SE 181098 C1 SE181098 C1 SE 181098C1
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- Sweden
- Prior art keywords
- dioxolane
- vinyl
- composition according
- isopropenyl
- cobalt
- Prior art date
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/12—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
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- 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
- C08F24/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D137/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen; Coating compositions based on derivatives of such polymers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
Description
Uppfinnare: H F Reinhardt Prioritet begard tem den 13 november 1959 (USA) Foreliggande uppfinning hanfor sig till lufttorkande, filmbildande kompositioner och i synnerhet till sadana kompositioner, vilka som huvudbestandsdelar innehalla en etylenomattad 1,3- dioxolan och ett koboltsickativ. Inventor: H F Reinhardt Priority set forth November 13, 1959 (USA). The present invention relates to air-drying, film-forming compositions and in particular to such compositions which contain as major constituents an ethylene-saturated 1,3-dioxolane and a cobalt siccative.
Det har belt mot formodan visat sig aft kompositioner, som innehalla en speciell grupp av av etylenomattade 1,3-dioxolaner och en liten effektiv mangd av ett koboltsalt av den typ, som vanligen anvandes som sickativ i lufttorkande larger, fernissor och emaljlacker, torka i luft, dvs. nar de exponeras mot luft eller syre vid normal mAlningstemperatur, underga relativt tunna utfallningar eller bela.ggningar av sadana kompositioner en forandring, som omvandlar utgangsmaterialet till en torr, sammanhangande film eller belaggning med det vanliga utseendet hos en film eller belaggning av en konventionell, lufttorkande och filmbildande komposition, som exempelvis ãr baserad pa en torkande glyceridolja, torkande oljelack eller en torkande oljemodifierad alkyd. De omattade dioxolaner, som erfordras enligt foreliggande uppfinning ha foljande strukturformel H R—C—C—R, 0 / \ H R, dar R betecknar en radikal bestaende av vinyl och isopropenyl, dar R, betecknar en radikal bestaende av vale, vinyl, propenyl, isopropenyl, beta-fenylvinyl, beta-(2-fury1)-vinyl, fenyl, 2-furyl och bieykloheptadienyl, och R, betecknar en radikal innehallande mattad C1—C9 alkyl, vinyl, propenyl, isopropenyl, betafenylvinyl, beta-(2-fury1)-vinyl, fenyl, tetrahydrofenyl, bieykloheptadienyl, 2-furyl, dihydro-pyranyl och dikloretyl, varvid minst en av R, och R, utgores av en radikal bestaende av vinyl och isopropenyl. Compositions containing a special group of ethylene-reacted 1,3-dioxolanes and a small effective amount of a cobalt salt of the type commonly used as a desiccant in air-drying larger, varnishes and enamels have been found to dry in air, i.e. when exposed to air or oxygen at normal painting temperatures, relatively thin precipitates or coatings of such compositions undergo a change which transforms the starting material into a dry, cohesive film or coating with the usual appearance of a film or coating of a conventional, air-drying and film-forming composition, which is based, for example, on a drying glyceride oil, drying oil varnish or a drying oil-modified alkyd. The unsaturated dioxolanes required by the present invention have the following structural formula HR-C-C-R, O / \ HR, where R represents a radical consisting of vinyl and isopropenyl, where R represents a radical consisting of vale, vinyl, propenyl, isopropenyl, beta-phenylvinyl, beta- (2-furyl) -vinyl, phenyl, 2-furyl and bicycloheptadienyl, and R 1 represents a radical containing matte C 1 -C 9 alkyl, vinyl, propenyl, isopropenyl, betafenylvinyl, beta- (2- fury1) -vinyl, phenyl, tetrahydrophenyl, bicycloheptadienyl, 2-furyl, dihydropyranyl and dichloroethyl, at least one of R 1 and R 2 being a radical consisting of vinyl and isopropenyl.
Exempel pa sadana omattade dioxolaner aro 2,4,5-triviny1-1,3-dioxolan; 2,4,5-triisopropenyl1,3-dioxolan; 4,5-diviny1-2-fenyl-1,3-dioxolan och 4-isopropenyl-2-vinyl-1,3-dioxolan. Examples of such unsaturated dioxolanes are 2,4,5-trivinyl-1,3,3-dioxolane; 2,4,5-triisopropenyl1,3-dioxolane; 4,5-divinyl-2-phenyl-1,3-dioxolane and 4-isopropenyl-2-vinyl-1,3-dioxolane.
Ytterligare andra typer ft-am& av heskrivningens arb ets exemp el. Still other types ft-am & of heskrivningens arb ets exemp el.
Nomenklaturen for dessa foreningar är baserad pa ringens tva syreatomer i 1- och 3-lagena med ringens kolatomer i 2-, 4- och 5-lagena. The nomenclature of these compounds is based on the two oxygen atoms of the ring in the 1- and 3-layers with the carbon atoms of the ring in the 2-, 4- and 5-layers.
Ett satt att framstalla sadana foreningar inbegriper kondensering av en lamplig aldehyd med en lamplig diol, foretradesvis under inverkan av varme i narvaro av en syrakatalysator, foljt av neutralisering och/eller ett avlagsnande av katalysatorn och slutlig rening, t. ex. genom fraktionering. Exempelvis kan 2,4,5-triviny1-1,3-dioxolan framstallas, genom att man later eft overskott av t. ex. 2-4 mol akrolein reagera med 1 mol divinylglykol (dvs. 1,5-hexadien-3,4-diol) vid 20-35° C under 1-3 h i nArvaro av cirka 0,03 ekvivalent klorvatesyrakatalysator, fiiljt av neutralisering av katalysatorn med exempelvis natriumacetat och avslutad genom fraktionerad destillation under vakuum. Som ett annat exempel kan 4-isopropeny1-5-viny1-2-buty1-1,3-dioxolan framstallas pa ett analogt salt fran 1-viny1-2- isopropenyletylenglykol, som diolen, och valeraldehyd som aldehyden. One way of preparing such compounds involves condensing a lamp aldehyde with a lamp diol, preferably under the influence of heat in the presence of an acid catalyst, followed by neutralization and / or a removal of the catalyst and final purification, e.g. by fractionation. For example, 2,4,5-trivinyl-1,3,3-dioxolane can be prepared by leaving excess e.g. 2-4 moles of acrolein react with 1 mole of divinyl glycol (ie 1,5-hexadiene-3,4-diol) at 20-35 ° C for 1-3 h in the presence of about 0.03 equivalent of hydrochloric acid catalyst, followed by neutralization of the catalyst with, for example, sodium acetate and terminated by fractional distillation under vacuum. As another example, 4-isopropenyl-5-vinyl-2-butyl-1,3-dioxolane can be prepared on an analogous salt of 1-vinyl-2-isopropenylethylene glycol, such as the diol, and valeraldehyde as the aldehyde.
Koboltsickativen, som erfordras enligt uppfinningen, aro de som vanligen anvandas Mom farg-, fernissa- och lackfargstekniken, dvs. tvalar, salter och liknande, som Aro losliga i tillrAcklig mangd for att effektivt framj a snabb lufttorkning, antingen direkt i den omattade dioxolanen eller i minst ett av de organiska losningsmedel, som aro vanliga inom belaggningstekniken och for ett onskat a.ndamal kunna anvandas i vissa kompo- sitioner enligt uppfinningen. Exempel pa sadana kobolttvalar, -salter och liknande oktoat aro oleat, linoleat, naftenat, resinat och koboltsalter av partiella estrar av dikarbonsyror (exempelvis Ci—Cis alkylsyraftalat, malonat, succinat, adipat 2— — eller sebacat). Blandningar av sadana koboltforeningar med liknande fOreningar av andra sicicativmetaller, som bly, mangan, zink, koppar, jam och nickel. The cobalt siccatives required according to the invention are those commonly used in the paint, varnish and lacquer paint techniques, i.e. whey, salts and the like, which are soluble in sufficient quantity to effectively promote rapid air drying, either directly in the unsaturated dioxolane or in at least one of the organic solvents which are common in the coating technique and for a desired purpose can be used in certain compositions according to the invention. Examples of such cobalt whales, salts and similar octoates are oleate, linoleate, naphthenate, resinate and cobalt salts of partial esters of dicarboxylic acids (for example C 1 -C 18 alkyl acid phthalate, malonate, succinate, adipate 2 - or sebacate). Mixtures of such cobalt compounds with similar compounds of other sicicative metals, such as lead, manganese, zinc, copper, jam and nickel.
Normalt ãr mangden koboltsickativ ekvivalent med 0,0005 %-3 % kobolt raknat pa vikten av den omattade dioxolanen. Normally, the amount of cobalt siccative equivalent to 0.0005% -3% cobalt is based on the weight of the unsaturated dioxolane.
Ndr torkning skall upptrada vid normal rums- eller atmosfarstemperatur, utgor den anvanda mangden kobolt foretradesvis cirka 0,011,0 %. Nar snabbtorkning eller hardning anvandes for att avkorta torkningsperioden, ãr den anvanda mangden fOretra.desvis 0,0005 %-0,01 %. When drying should occur at normal room or atmospheric temperature, the amount of cobalt used is preferably about 0.011.0%. When rapid drying or curing is used to shorten the drying period, the amount used is preferably 0.0005% -0.01%.
De nya kompositionerna enligt fOreliggande uppfinning inbegripa flytande dioxolaner, enar dessa forlana dem sjalva en enkel beredning av losningsmedelsfria och flytande slutprodukter, en typ som ãr speciellt onskvard pa grand av att kostnaden och eldrisken for flyktiga organiska losningsmedel elimineras. Emellertid ken dioxolaner, som Oro mera viskosa an Onskvart fOr ett speciellt slutandamal, anvandas i form av en. losning i ett vanligt lbsningsmedel. Lampliga flyktiga organiska losningsmedel inbegripa alifatiska och aromatiska flytande kolvaten, estrar, etrar, ketoner, alkoholer och blandningar darav. The novel compositions of the present invention include liquid dioxolanes, which provide them themselves with a simple preparation of solvent-free and liquid end products, a type which is particularly desirable in eliminating the cost and fire hazard of volatile organic solvents. However, ken dioxolanes, which are more viscous than Onskvart for a particular final purpose, are used in the form of a. solution in a common solvent. Suitable volatile organic solvents include aliphatic and aromatic liquid hydrocarbons, esters, ethers, ketones, alcohols and mixtures thereof.
De nya kompositionerna kunna anvandas som klara, opigmenterade belaggningskompositioner, med losningsmedel om sa erfordras for ett bekvamt paforande, eller kunna de pigmenteras, varvid anvdndes mangder som aro val kanda inom tekniken, med pigment som vanligen anvandes i belaggningstekniken. t. ex. metalloxider, sulfider, sulfater, silikater, kromater, jamblatt, organiska larger och metallpigment i flagform. Som i fallet med andra lufttorkande material fOrdroja pigmenten. torkning. Vanligtvis bora dessa undvikas i belaggningskompositioner, som dro sammansatta for att torka vid normala temperaturer, men den fOrdrojande effekten kan minskas genom snabbtorkning eller infOrlivning ay lampliga tillsatser. The new compositions can be used as clear, unpigmented coating compositions, with solvents if required for a convenient application, or they can be pigmented, using amounts of choice in the art, with pigments commonly used in the coating technique. e.g. metal oxides, sulphides, sulphates, silicates, chromates, jamblatt, organic larger and metal pigments in flag form. As in the case of other air-drying materials, the pigments are dehydrated. drying. Usually these drills are avoided in coating compositions which are compounded to dry at normal temperatures, but the retarding effect can be reduced by rapid drying or incorporation of suitable additives.
De omattade dioxolanerna kunna utgOra hela den organiska filmbildande komponenten hos de nya kompositionerna, eller de kunna blandas med andra valkanda filmbildare t. ex. vegetabiliska oljor, oljemodifierade alkyder, oljelacker, alkylerade karbarnidaldehydplaster, alkylerade melaminaldehyd- plaster, p olyepoxip olyhydroxi- plaster, acetylerade fenolaldehydplaster, cellulosanitrat, cellulosaacetat, cellulosaacetatbutyrat, polymerer och sampolymerer av vinyl- och vinylidenfbreningar t. ex. vinylklorid, vinylidenklorid, vinylacetat, akryl- och metakrylsyra och estrarna darav, styren, butadien och liknande; elastomerer som neopren, styrenbutadiengummin, akrylnitrilbutadiengummin och och isobutylenisoprengummin; polyuretaner och silikoner. The unsaturated dioxolanes may constitute the entire organic film-forming component of the new compositions, or they may be mixed with other electron-forming film formers, e.g. vegetable oils, oil-modified alkyds, oil paints, alkylated carbarnidaldehyde plastics, alkylated melaminaldehyde plastics, polyoxypoly polyhydroxy plastics, acetylated phenol aldehyde plastics, cellulose nitrate, cellulose acetate, cellulose acetate butyrates, polymers and copolymers of vinyl bene. vinyl chloride, vinylidene chloride, vinyl acetate, acrylic and methacrylic acid and their esters, styrene, butadiene and the like; elastomers such as neoprene, styrene butadiene rubbers, acrylonitrile butadiene rubbers and and isobutylene isoprene rubbers; polyurethanes and silicones.
Andra vanliga ingredienser hos organiska filmbildande kompositioner kunna anvandas pa det satt och i de proportioner, som ãr val kanda inom tekniken. Dessa inbegripa mjukningsmedel, katalysatorer, hdrdare, skinnhindrande medel och ytaktiva medel. Other common ingredients of organic film-forming compositions can be used in the manner and in the proportions known in the art. These include plasticizers, catalysts, hardeners, skin conditioners and surfactants.
De klara opigmenterade kompositionerna enLigt uppfinningen kunna framstallas genom enkel blandning ay ingredienserna. Ndr pigmentering inbegripes, erfordras en konventionell pigmentrivning eller en dispergering. The clear unpigmented compositions according to the invention can be prepared by simple mixing of the ingredients. If pigmentation is included, a conventional pigment shredding or dispersion is required.
De nya kompositionerna enligt uppfinningen Ore vd.rdefulla for att skydda och/eller att dekorera foremal, framstallda av sadana material som tra, keramik, lader och tyg. De nya kompositionerna kunna anbringas medelst varje tjanlig metod t. ex. penselstrykning, sprutning, doppning, flytning och rullbelaggning, foljt av normal lufttorkning via enkel exponering mot luft vid van-hg rums- eller atmosfdrstemperatur eller genom snabbtorkning vid en passande temperatur Over omgivningens temperatur men under en temperatur vid vilken sonderdelning eller andra icke godtagbara resultat bliva folj den. The new compositions according to the invention are valuable for protecting and / or decorating objects, made of such materials as wood, ceramics, ladders and fabrics. The new compositions can be applied by any useful method, e.g. brush ironing, spraying, dipping, floating and roller coating, followed by normal air drying via simple exposure to air at a low room or atmosphere temperature or by quick drying at a suitable temperature Above ambient temperature but below a temperature at which probe division or other unacceptable results occur follow it.
Foljande exempel visa principerna och tillampningen av uppfinningen, men desamma Oro ej avsedda att begransa uppfinningens omfattning. For savitt icke annat angives, arc delar och procenttal baserade ph vikt. The following examples illustrate the principles and application of the invention, but the same concerns are not intended to limit the scope of the invention. For savit unless otherwise stated, arc parts and percentages are based ph weight.
Exempel 1Viktdelar 2,4,5-triviny1-1,3-dioxolan 100,00 koboltbutylftalat 0,46 (10,9 % kobolt) En lufttorkande, filmbildande komposition enligt uppfinningen framstalldes genom blandning ay de tva oven specificerade komponenterna I de angivna mangdema till dess att koboltsaltet fullstandigt blev upplost i dioxolanen. Kobolt, kalkylerad som metal', forekona i en mangd ay 0,05 viktprocent rdknat ph dioxolanen. En tunn belaggning framstalIdes genom att draga ut ett litet prom ay denna belaggning under en schaberklinga (0,016 mm spelrum) pa en ren glasyta, varefter den vata beldggningen exponerades mot luft yid rumstemperatur. 130 cirka 3 h blev belaggningen torr och hardnade tillrd.ckligt fOr att kunna handhavas utan att skadas. Den var klar och haftade bra vid underlaget. Lllinande belaggningar framstalldes pa tra och metall med samma teknik. De erhallna belaggningarna visade sig varaktiga nar de exponerades utomhus. I avseende p0 tra och metallforemal skyddade belaggningarna underlaget frail en forstOrande inverkan ay vaderleken. Example 1 Weight parts 2,4,5-trivinyl-1,3,3-dioxolane 100.00 cobalt butyl phthalate 0.46 (10.9% cobalt) An air-drying, film-forming composition according to the invention was prepared by mixing the two components specified above in the amounts indicated to until the cobalt salt was completely dissolved in the dioxolane. Cobalt, calculated as metal, is present in an amount of 0.05% by weight of the dioxolane. A thin coating was prepared by pulling out a small prom ay of this coating under a doctor blade (0.016 mm clearance) on a clean glass surface, after which the wet coating was exposed to air at room temperature. 130 about 3 hours the coating became dry and hardened sufficiently to be able to be handled without being damaged. It was ready and adhered well to the surface. Lining linings were made of wood and metal using the same technology. The coatings obtained proved to be durable when exposed outdoors. With regard to wood and metal formulations, the coatings protected the substrate from an increasing effect on the weather.
Exempel 2. Example 2.
En pigmenterad analog till kompositionen hos exempel 1, vilken analog belyser de forutnamnda pigmenterade produkterna hos uppfinningen, framstalldes genom ruining av 60 viktdelar titandioxidpigment i 100 delar ay dioxolanen och 100 delar toluen till dess att en slat, likformig dispersion erholls. Koboltsaltet (0,46 delar) upplostes i denna komposition genom blandning. Den erhallna vita produkten kunde sprayas f Or att giva belaggningar, som lufttorkade pa cirka 3 h och som voro harda, sega och vaderbestandiga. — —3 Andra pigment, sasom forut namnts, kunna ersatta hela mdngden eller en del av mangden titandioxid i denna produkt. Manga fargade pigment kunna anvandas i avsevart mindre mangder, men fortfarande giva adekvat tackformaga vid normal b eldggningstjo cklek. A pigmented analog of the composition of Example 1, which illustrates the aforementioned pigmented products of the invention, was prepared by grinding 60 parts by weight of titanium dioxide pigments in 100 parts of the dioxolane and 100 parts of toluene until a smooth, uniform dispersion was obtained. The cobalt salt (0.46 parts) was dissolved in this composition by mixing. The resulting white product could be sprayed to give coatings which were air dried in about 3 hours and which were hard, tough and weather resistant. - —3 Other pigments, as previously mentioned, may replace all or part of the amount of titanium dioxide in this product. Many colored pigments can be used in considerably smaller amounts, but still give adequate thanksgiving shape at normal building thickness.
Ytterligare exempel pa kompositioner enligt uppfinningen framga av foliande tabell, i vilken viktandelarna for huvudkomponenterna dro angivna. Avensa angives tiden (i h), som erfordras fOr en opigmenterad komposition att lufttorka till klibbfritI stadium och tiden (i min.) under vilken vissa av beldggningarna snabbtorkades, som en ersattning for forlangd exponering mot luft vid rumstemperatur. Hardnings- och snabbtorkningstemperaturen 150° C var uteslutande en bekvam sadan. Lagre temperaturer kunna anvandas med motsvarande ldngre tider och vice versa. Pigmentering kan aven genomforas sasom i exempel 2, em man sd Onskar. Ldmpliga kompositioner anbringades medelst en konventionell metod, t. ex. penselstrykning, flytning, rullbelaggning, sprutfling eller doppning och samtliga erhallna torkade belaggningar hade egenskaper, som i allmanhet voro liknande de hos produkterna enligt foregaende exempel. Further examples of compositions according to the invention are shown in the following table, in which the parts by weight of the main components are indicated. Avensa indicates the time (in h) required for an unpigmented composition to air dry to a tack-free stage and the time (in min.) During which some of the coatings were rapidly dried, as a replacement for required exposure to air at room temperature. The curing and quick-drying temperature of 150 ° C was exclusively a convenient one. Lower temperatures can be used with correspondingly longer times and vice versa. Pigmentation can also be carried out as in Example 2, if desired. Suitable compositions were applied by a conventional method, e.g. brush ironing, floating, roller coating, spray flaking or dipping, and all of the resulting dried coatings had properties which were generally similar to those of the products of the preceding examples.
Tabell 1. Table 1.
Ex-Dioxolan em-(Nedtecknade som prefix till termen pel1,3-dioxolan) Koboltsalt % kobolt baserad pa dioxolan h vid rumstemperatur till torrt tillstand Minuter vid 150° C 3. 4-isopropenyl-5-vinyl-2-butyl oktoat 0,07 4. 4-vinyl-2-isopropenyl butyl-ftalat 0,7 3 5. 4,5-dllsopropeny1-2-beta fenylvinyl naftenat 1,0 14 6. 4-vinyl-5-isopropenyl-2-(alfa, beta dikloretyl) 1,0 14 7. 4-isopropenyl-5-fenyl-2-vinyl oktoat 0,8 8. 4-vinyl-5-propeny1-2-isopropenyl butyl-ftalat 0,07 4 9. 4-isopropenyl-5-beta (2'-furyl)viny1-2-vinyl »» 0,9 10. 4,5-diviny1-2-propenyl naftenat 0,09 4 11. 4-isopropenyl-5-vinyl-2-beta (2'-furyl)vinyl butyl-ftalat 0,012 12. 4-vinyl-5-beta fenylviny1-2-isopropenyl oktoat 0,1 14 13. 4-isopropenyl-5-vinyl-2-tetrahydrofenyl S 0,1 12 14. 4,5-diviny1-2-fenyl butyl-ftalat 0,3 15. 4-isopropeny1-5-(2'-fury1)-2-vinyl »» 0,3 9 16. 4-vinyl-5-bicykloheptadieny1-2-isopropenyl linoleat 0,1 17. 4-4sopropeny1-5-viny1-2-tetrahydrofenyl oktoat 0,2 18. 4,5-diisopropeny1-2-dihydropyranyl butyl-ftalat 0,2 19. 4-isopropenyl-5-vinyl-2-(2'-furyl) 0,09 20. 4,5-diviny1-2-metyl 0,3 9 21. 4,5-diviny1-2-bicyklopentadienyl 0,3 14 22. 4,5-diviny1-2-nonyl S 0,3 23. 2,4,5 triisopropenyl 0,7 6 Pet ãr uppenbart att manga vitt skilda utforingsformer av uppfinningen kunna forekomma, utan att desamma avvika frail tanken och omfattningen av uppfinningen. Ex-Dioxolane em- (Recorded as prefix to the term pel1,3-dioxolane) Cobalt salt% cobalt based on dioxolane h at room temperature to dry state Minutes at 150 ° C 3. 4-Isopropenyl-5-vinyl-2-butyl octoate 0, 07 4. 4-vinyl-2-isopropenyl butyl phthalate 0.7 3 5. 4,5-disopropenyl-2-beta phenylvinyl naphthenate 1.0 14 6. 4-vinyl-5-isopropenyl-2- (alpha, beta dichloroethyl) 1.0 14 7. 4-Isopropenyl-5-phenyl-2-vinyl octoate 0.8 8. 4-vinyl-5-propenyl-2-isopropenyl butyl phthalate 0.07 4 9. 4-isopropenyl-5 -beta (2'-furyl) vinyl-2-vinyl »» 0.9 10. 4,5-divinyl-2-propenyl naphthenate 0.09 4 11. 4-isopropenyl-5-vinyl-2-beta (2 ' -furyl) vinyl butyl phthalate 0.012 12. 4-vinyl-5-beta phenylvinyl-2-isopropenyl octoate 0.1 14 13. 4-isopropenyl-5-vinyl-2-tetrahydrophenyl S 0.1 12 14. 4.5 -divinyl-2-phenyl butyl-phthalate 0.3 15. 4-Isopropenyl-5- (2'-furyl) -2-vinyl »» 0.3 9 16. 4-vinyl-5-bicycloheptadienyl-2-isopropenyl linoleate 0.1 17. 4-4sopropenyl-5-vinyl-2-tetrahydrophenyl octoate 0.2 18. 4,5-diisopropenyl-2-dihydropyranyl butyl-fta lat 0.2 19. 4-Isopropenyl-5-vinyl-2- (2'-furyl) 0.09 20. 4,5-divinyl-2-methyl 0.3 9 21. 4,5-divinyl-2- Bicyclopentadienyl 0.3 14 22. 4,5-divinyl-2-nonyl S 0.3 23. 2,4,5 Triisopropenyl 0,7 6 It is obvious that many widely differing embodiments of the invention may occur, without departing from the foregoing. the idea and scope of the invention.
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