DE1247660B - Process for the homo- and copolymerization of vinyl compounds - Google Patents
Process for the homo- and copolymerization of vinyl compoundsInfo
- Publication number
- DE1247660B DE1247660B DE1965D0046251 DED0046251A DE1247660B DE 1247660 B DE1247660 B DE 1247660B DE 1965D0046251 DE1965D0046251 DE 1965D0046251 DE D0046251 A DED0046251 A DE D0046251A DE 1247660 B DE1247660 B DE 1247660B
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- radical
- polymerization
- copolymerization
- homo
- 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
- 238000000034 method Methods 0.000 title claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 7
- 238000007334 copolymerization reaction Methods 0.000 title claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- -1 diketone compound Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 7
- 229920006305 unsaturated polyester Polymers 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005594 diketone group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000003505 polymerization initiator Substances 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VKGXRCOYMCCVTN-UHFFFAOYSA-N acetaldehyde;thiophene Chemical compound CC=O.C=1C=CSC=1 VKGXRCOYMCCVTN-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229940100595 phenylacetaldehyde Drugs 0.000 description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- LNKQTTQZURKWDO-UHFFFAOYSA-N 2-(furan-2-yl)acetaldehyde Chemical compound O=CCC1=CC=CO1 LNKQTTQZURKWDO-UHFFFAOYSA-N 0.000 description 1
- HNUKTDKISXPDPA-UHFFFAOYSA-N 2-oxopropyl Chemical compound [CH2]C(C)=O HNUKTDKISXPDPA-UHFFFAOYSA-N 0.000 description 1
- WYJIHKGNYDLFGB-UHFFFAOYSA-N 3-(furan-2-yl)-2-oxopropanoic acid Chemical class OC(=O)C(=O)CC1=CC=CO1 WYJIHKGNYDLFGB-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- VJRAYHSMXAAUOU-UHFFFAOYSA-N acetaldehyde;furan Chemical compound CC=O.C=1C=COC=1 VJRAYHSMXAAUOU-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XESLIEMIJSFBOC-UHFFFAOYSA-N ethene;thiophene Chemical compound C=C.C=1C=CSC=1 XESLIEMIJSFBOC-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polymerization Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Description
Verfahren zur Homo- und Copolymerisation von Vinylverbindungen Es ist bekannt, ungesättigte Polyester, gegebenenfalls zusammen mit anpolymerisierbaren Monomeren, sowie monomere Vinylverbindungen oder deren Substitutionsprodukte mit Hilfe von peroxydischen Katalysatoren zu polymerisieren. Die entstehenden Polymerisate auf der Grundlage von ungesättigten Polyestern haben vielfache technische Anwendung gefunden. Sie zeigen im allgemeinen gute mechanische Eigenschaften, erfüllen aber in bezug auf die Schlagbiegefestigkeit nicht alle Anforderungen. Bei der Polymerisation von Vinylmonomeren oder deren Substitutionsprodukten fällt bei diesem Verfahren oft der unkontrollierte Ablauf der Polymerisation nachteilig ins Gewicht.Process for homo- and copolymerization of vinyl compounds Es is known, unsaturated polyesters, optionally together with polymerizable Monomers, as well as monomeric vinyl compounds or their substitution products with Polymerize with the help of peroxide catalysts. The resulting polymers based on unsaturated polyesters have multiple technical applications found. They generally show good mechanical properties, but do not all of the requirements related to impact resistance. During the polymerization of vinyl monomers or their substitution products fall in this process the uncontrolled course of the polymerization is often a disadvantage.
Es ist außerdem bekannt, bei der Auspolymerisation von ungesättigten Polyestern oder Polyesterharzmischungen zur Erzielung einer gleichmäßigen Polymerisation und besseren mechanischen Eigenschaften Phenylacetaldehyd und/oder dessen im Benzolkern substituierte Derivate oder a-monosubstituierte Phenylacetaldehyde, gegebenenfalls in Kombination mit Peroxyden, zu verwenden. It is also known in the polymerization of unsaturated Polyesters or polyester resin mixtures to achieve uniform polymerization and better mechanical properties of phenylacetaldehyde and / or its in the benzene nucleus substituted derivatives or α-monosubstituted phenylacetaldehydes, optionally to be used in combination with peroxides.
Es wurde nun gefunden, daß man die Homo- oder Copolymerisation von gegebenenfalls substituierten Vinylverbindungen, vorzugsweise in Gegenwart ihrer Polymerisate, oder von ungesättigten Polyestern, vorzugsweise in Gegenwart von anpolymerisierbaren Monomeren und in Gegenwart von enolisierbaren Aldehyden, Ketonen oder Diketonen als Katalysatoren, durchführen kann, wenn man als Katalysator mindestens eine enolisierbare Aldehyd-, Keton- oder Diketonverbindung der allgemeinen Formeln oder oder mindestens eine diese Verbindungen unter den Polymerisationsbedingungen bildende Substanz, ge- gebenenfalls zusammen mit an sich bekannten Polymerisationsinitiatoren, verwendet. In den Formeln bedeutet R1 einen Thienyl-, Furyl- oder Pyridylrest, der auch am Stickstoffatom durch eine Alkylgruppe substituiert sein kann, R2 vorzugsweise ein Wasserstoffatom oder einen Alkyl- oder Aralkylrest und R3 einen Alkyl- oder einen gegebenenfalls durch Alkyl-, Alkoxygruppen oder Halogenatome substituierten Arylrest oder einen heterocyclischen Rest.It has now been found that the homopolymerization or copolymerization of optionally substituted vinyl compounds, preferably in the presence of their polymers, or of unsaturated polyesters, preferably in the presence of monomers which can be polymerized and in the presence of enolizable aldehydes, ketones or diketones as catalysts, can be carried out, if the catalyst used is at least one enolizable aldehyde, ketone or diketone compound of the general formulas or or at least one substance which forms these compounds under the polymerization conditions, optionally together with polymerization initiators known per se, is used. In the formulas, R1 is a thienyl, furyl or pyridyl radical, which can also be substituted on the nitrogen atom by an alkyl group, R2 is preferably a hydrogen atom or an alkyl or aralkyl radical and R3 is an alkyl or an optionally by alkyl, alkoxy or halogen atom substituted aryl radical or a heterocyclic radical.
Die erfindungsgemäß zu verwendenden Katalysatoren übertreffen die bisher bekannten, weil sie eine tiefere Spitzentemperatur bei der Auspolymerisation ergeben und dadurch Formkörper liefern, die spannungs- und rißfrei- sind. Hieraus ergeben sich weitere Verbesserungen hinsichtlich der mechanischen Eigenschaften, wie höhere Schlagbiegefestigkeiten. Dabei sind die Gelzeiten nicht wesentlich verlängert. The catalysts to be used according to the invention exceed this previously known because they have a lower peak temperature during the final polymerization and thereby deliver moldings that are free of stress and cracks. From this there are further improvements in terms of mechanical properties, like higher impact strengths. The gel times are not significantly extended.
Enolisierbare Aldehyde, die im Rahmen der vorliegenden Erfindung verwendet werden können, sind beispielsweise Thiophenacetaldehyd, Furanacetaldehyd, Pyridylacetaldehyd, N-Methylpyridylacetaldehyd usw. Unter den enolisierbaren Ketonen sind fl-Furylmethylketon, a-Thionylmethylketon,. a-Pyridylmethylketon sowie Furanbrenztraubensäureest.er, z. B. Methyl- und Ethylester der Formel und die entsprechenden Amide, z. B. zu nennen. Zu den Verbindungen, die unter den Polymerisationsbedingungen enolisierbare Aldehyde bzw. Ketone bilden, gehören beispielsweise a-Thienylmalonsäurediurethan, Thiophenacetaldehyddiacetat, Thienyläthylidendiacetat, Thiophenacetaldehyd-Butylamin- Kondensat, Thiophenacetaldehyd - oxim, Thiophenvinylacetat, Thiophenacetaldehyd - anil, Thiophenäthylenoxyd, a - äthylen - thiophen - methyläther, a-;.thylen-thiophen- äthyläther. Ferner gehören hierzu die Acetale der entsprechenden Aldehyde.Enolizable aldehydes which can be used in the context of the present invention are, for example, thiophene acetaldehyde, furan acetaldehyde, pyridyl acetaldehyde, N-methylpyridyl acetaldehyde, etc. Among the enolizable ketones are fl-furyl methyl ketone, α-thionyl methyl ketone. α-pyridyl methyl ketone and furanpyruvic acid esters, e.g. B. methyl and ethyl esters of the formula and the corresponding amides, e.g. B. to call. Among the compounds that form under the polymerization enolizable aldehydes and ketones include, for example a-Thienylmalonsäurediurethan, Thiophenacetaldehyddiacetat, Thienyläthylidendiacetat, Thiophenacetaldehyd-butylamine condensate Thiophenacetaldehyd - oxime, Thiophenvinylacetat, Thiophenacetaldehyd - anil, Thiophenäthylenoxyd, a - ethylene - thiophen - methyl ether , a - ;. ethylene thiophene ethyl ether. This also includes the acetals of the corresponding aldehydes.
Die erfindungsgemäßen Katalysatoren können in den bei analogen Polymerisationen unter Verwendung anderer Katalysatoren üblichen Mengen zugesetzt werden. Es empfiehlt sich jedoch ein Einsatz von etwa 0,1 bis etwa 5 Gewichtsprozent, vorzugsweise von etwa 0,5 bis etwa 2 Gewichtsprozent, bezogen auf die polymerisationsfähige Gesamtmasse. The catalysts of the invention can be used in analogous polymerizations customary amounts can be added using other catalysts. It recommends however, a use of about 0.1 to about 5 percent by weight, preferably of about 0.5 to about 2 percent by weight, based on the total polymerizable mass.
Die Polymerisation wird vorzugsweise bei erhöhten Temperaturen durchgeführt. Beispielsweise kann man den Temperaturbereich von etwa 70 bis etwa 100"C einhalten. The polymerization is preferably carried out at elevated temperatures. For example, the temperature range from about 70 to about 100.degree. C. can be maintained.
Es ist besonders zweckmäßig, schon die Mischung der Reaktionspartner, also der zu polymerisierenden Verbindungen mit dem Polymerisationsregler bei erhöhter Temperatur vorzunehmen, beispielsweise zwischen 30 und 70"C, vorzugsweise bei etwa 50"C. It is particularly useful to already mix the reactants, so the compounds to be polymerized with the polymerization regulator at increased Make temperature, for example between 30 and 70 "C, preferably at about 50 "C.
Es ist nicht notwendig, das erfindungsgemäße Verfahren unter Luftausschluß durchzuführen. It is not necessary to carry out the process according to the invention with the exclusion of air perform.
Bei der Polymerisation können außerdem Füll-und/oder Farbstoffe und/oder Pigmente und/oder Verstärkungsfasern anwesend sein. In addition, fillers and / or dyes and / or Pigments and / or reinforcing fibers may be present.
Das Verfahren läßt sich außerdem bei der Herstellung von -Uberzügen und Lacken anwenden. The process can also be used in the production of coatings and apply varnishes.
Die Polymerisation kann unter Verwendung von handelsüblichen ungesättigten Polyestern oder ungesättigten Polyesterharzmassen durchgeführt werden. The polymerization can be carried out using commercially available unsaturated Polyesters or unsaturated polyester resin compositions are carried out.
Sie ist jedoch auch auf die Polymerisation von Vinylverbindungen oder deren Substitutionsprodukten für sich allein anwendbar. Beispiele für die Verbindungen sind Ester der Acryl- oder Methacrylsäure, Acrylnitril, Vinylcarbazol, Vinylpyrrolidon, Vinylchlorid, Vinylidenchlorid und Styrol. Bevorzugt wird jedoch Methacrylsäuremethylester verwendet. Diese Stoffe können einzeln oder im Gemisch eingesetzt werden.However, it is also based on the polymerization of vinyl compounds or their substitution products can be used on their own. Examples of the connections are esters of acrylic or methacrylic acid, acrylonitrile, vinyl carbazole, vinyl pyrrolidone, Vinyl chloride, vinylidene chloride and styrene. However, methyl methacrylate is preferred used. These substances can be used individually or in a mixture.
Es ist außerdem möglich, neben den neuen Katalysatoren auch an sich bekannte Polymerisationskatalysatoren wie peroxydische Verbindungen mitzuverwenden. Ferner können auch Phenylacetaldehyd sowie die obengenannten Derivate dieser Verbindung mitverwendet werden. It is also possible per se, in addition to the new catalysts known polymerization catalysts such as peroxide compounds to be used. Phenylacetaldehyde and the abovementioned derivatives of this compound can also be used can also be used.
Beispiel 500 Teile eines handelsüblichen ungesättigten Polyesters
auf der Basis von Maleinsäure- und Phthålsäureanhydrid und Athylenglykol und Diäthylenglykol,
der mit 250 Teilen Styrol abgemischt ist, wird unter Verwendung verschiedener Katalysatoren
auspolymerisiert. Die Polymerisationsbedingungen sowie die erhaltenen Ergebnisse
sind in der nachfolgenden Tabelle angeführt.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965D0046251 DE1247660B (en) | 1965-01-15 | 1965-01-15 | Process for the homo- and copolymerization of vinyl compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1965D0046251 DE1247660B (en) | 1965-01-15 | 1965-01-15 | Process for the homo- and copolymerization of vinyl compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1247660B true DE1247660B (en) | 1967-08-17 |
Family
ID=7049596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1965D0046251 Pending DE1247660B (en) | 1965-01-15 | 1965-01-15 | Process for the homo- and copolymerization of vinyl compounds |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1247660B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1705214A1 (en) * | 2005-03-23 | 2006-09-27 | DSM IP Assets B.V. | Gel time drift-free resin compositions |
| EP1705218A1 (en) * | 2005-03-23 | 2006-09-27 | DSM IP Assets B.V. | Gel time drift-free resin compositions |
-
1965
- 1965-01-15 DE DE1965D0046251 patent/DE1247660B/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1705214A1 (en) * | 2005-03-23 | 2006-09-27 | DSM IP Assets B.V. | Gel time drift-free resin compositions |
| EP1705218A1 (en) * | 2005-03-23 | 2006-09-27 | DSM IP Assets B.V. | Gel time drift-free resin compositions |
| WO2006100121A1 (en) * | 2005-03-23 | 2006-09-28 | Dsm Ip Assets B.V. | Gel time drift-free resin compositions |
| WO2006100120A1 (en) * | 2005-03-23 | 2006-09-28 | Dsm Ip Assets B.V. | Gel time drift-free resin compositions |
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