NO133326B - - Google Patents
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- NO133326B NO133326B NO433969A NO433969A NO133326B NO 133326 B NO133326 B NO 133326B NO 433969 A NO433969 A NO 433969A NO 433969 A NO433969 A NO 433969A NO 133326 B NO133326 B NO 133326B
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- monomers
- mixture
- reaction step
- binder
- reagents
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- 239000000203 mixture Substances 0.000 claims description 25
- 239000000178 monomer Substances 0.000 claims description 24
- 239000011230 binding agent Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229920000058 polyacrylate Polymers 0.000 claims description 6
- 239000004922 lacquer Substances 0.000 claims description 4
- 239000002966 varnish Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000000034 method Methods 0.000 description 18
- 239000003153 chemical reaction reagent Substances 0.000 description 15
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 12
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 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 2
- QGFSQVPRCWJZQK-UHFFFAOYSA-N 9-Decen-1-ol Chemical compound OCCCCCCCCC=C QGFSQVPRCWJZQK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- -1 vinyl halides Chemical class 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- PBNDUFBHPISRDY-UHFFFAOYSA-N 2-(3-phenylprop-2-enoxymethyl)oxirane Chemical compound C=1C=CC=CC=1C=CCOCC1CO1 PBNDUFBHPISRDY-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 1
- BSZGXCFUKRLAAN-UHFFFAOYSA-N 2-phenylprop-2-en-1-ol Chemical compound OCC(=C)C1=CC=CC=C1 BSZGXCFUKRLAAN-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000004808 allyl alcohols Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- HRKWOOHVRHBXHJ-UHFFFAOYSA-N hexan-2-yl prop-2-enoate Chemical compound CCCCC(C)OC(=O)C=C HRKWOOHVRHBXHJ-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000005267 main chain polymer Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- ACZNIBVNGPLHAC-UHFFFAOYSA-N penta-2,4-dien-1-ol Chemical compound OCC=CC=C ACZNIBVNGPLHAC-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002023 wood Substances 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
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
- C08F291/18—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00 on to irradiated or oxidised macromolecules
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
Description
Det er kjent å fremstille lakk som kan herdes ved elektronbestråling. Slik lakk egner seg for beskyttelse av forskjellige gjenstander, som gjenstander av tre eller metall. For dette formål er det vanlig å anvende blandinger av umettede monomerer med umettede polyestere, se f.eks. norsk patentskrift nr. 131.511. It is known to produce varnish that can be cured by electron irradiation. Such varnish is suitable for the protection of various objects, such as objects made of wood or metal. For this purpose, it is common to use mixtures of unsaturated monomers with unsaturated polyesters, see e.g. Norwegian patent document no. 131,511.
Det tas ved oppfinnelsen sikte på å tilveiebringe overtrekk som er spesielt motstandsdyktige mot hydrolyse og som har stor vær-bestandighet. The invention aims to provide covers which are particularly resistant to hydrolysis and which have great weather resistance.
Dette oppnås ved foreliggende lakkbindemiddel som er sær-preget ved det som er anført i kravets karakteriserende del. Den i blandingen inneholdte acrylpolymer har umettede sidegrupper som er skilt fra hovedcarbonkjeden med to etherbindinger, dvs. med formelen: This is achieved by the present lacquer binder, which is characterized by what is stated in the characterizing part of the claim. The acrylic polymer contained in the mixture has unsaturated side groups that are separated from the main carbon chain by two ether bonds, i.e. with the formula:
Denne struktur er meget motstandsdyktig mot påvirkninger, hvorved overtrekket får de ovenfor angitte fordelaktige egenskaper. Det er for samme formål blitt anvendt polymerer hvori de umettede sidegrupper er skilt fra hovedcarbonkjeden med én eller flere esterbindinger.(Se den ålment tilgjengelige svenske søknad som har ført til patent nr. 345.624.) En esterbinding er imidlertid mer tilbøyelig til å hydrolyseres, hvorved overtrekket kan nedbrytes. This structure is very resistant to influences, whereby the cover gets the advantageous properties mentioned above. Polymers have been used for the same purpose in which the unsaturated side groups are separated from the main carbon chain by one or more ester bonds. the cover can break down.
Det ovenfor angitte bindemiddel kan blandes med de vanlige pigmenter eller finfordelte fyllstoffer. Bindemidlet kan også anvendes uten pigmenter og kan eventuelt inneholde gjennomsiktige farvestoffer. Overtrekket kan altså ha karakter av fargeløse eller gjennomskinnelige lakker eller emaljer. The above-mentioned binder can be mixed with the usual pigments or finely divided fillers. The binder can also be used without pigments and may optionally contain transparent dyes. The coating can therefore have the character of colorless or translucent lacquers or enamels.
Uttrykket "elektronbestråling" anvendes her om sådan strål-ing som har tilstrekkelig energi til å bevirke en polymerisering i overtrekket, dvs. 5000 elektronvolt eller derover. Det anvendes fortrinnsvis minst 25000 elektronvolt pr. 25 mm avstand mellom strålingskilden og gjenstanden dersom mellomrommet er luft. Det kan foretas justeringer dersom det anvendes en gass med en annen motstand, som en oxygenfri inert gass, f.eks. nitrogen eller helium. Fortrinnsvis anvendes en elektronstråle med en gjennomsnittlig energi av 150000 - 450000 elektronvolt. The term "electron irradiation" is used here for such radiation that has sufficient energy to cause polymerization in the coating, i.e. 5000 electron volts or more. Preferably at least 25,000 electron volts per 25 mm distance between the radiation source and the object if the space is air. Adjustments can be made if a gas with a different resistance is used, such as an oxygen-free inert gas, e.g. nitrogen or helium. An electron beam with an average energy of 150,000 - 450,000 electron volts is preferably used.
Det er gunstig å herde de ovenfor angitte overtrekk eller malinger ved en forholdsvis lav temperatur, f.eks. mellom værelsetemperatur og den temperatur hvor den mest flyktige bestanddel i blandingen begynner å fordampe, som regel ved 20-70°C. Strålings-energien tilføres i doser mellom 0,1 og 100 Mrad pr. sekund under bevegelse av gjenstanden. Overtrekket skal fortrinnsvis motta en samlet dose av 5-15, Mrad, dvs. omtrent den samme dose som ifølge norsk patentskrift nr. 131.511. It is advantageous to cure the above-mentioned coatings or paints at a relatively low temperature, e.g. between room temperature and the temperature at which the most volatile component in the mixture begins to evaporate, usually at 20-70°C. The radiation energy is supplied in doses between 0.1 and 100 Mrad per second during movement of the object. The cover should preferably receive a total dose of 5-15, Mrad, i.e. approximately the same dose as according to Norwegian patent document no. 131,511.
Den acrylpolymer som inngår i bindemidlet, har en gjennomsnittlig molekylvekt av over 500, fortrinnsvis 4000-20000. Den inneholder altså 0,5-3,5 alkeniske dobbelbindinger (a-p-ole-finisk umettede grupper) pr. 1000 enheter molekylvekt. Det er jo her like mange dobbeltbindinger som det er sidekjeder med dobbelt-binding mellom de to endestilte carbonatomer. The acrylic polymer included in the binder has an average molecular weight of over 500, preferably 4000-20000. It therefore contains 0.5-3.5 alkenic double bonds (a-p-olenic unsaturated groups) per 1000 molecular weight units. There are as many double bonds here as there are side chains with a double bond between the two terminal carbon atoms.
Ifølge en fremgangsmåte kan man først fremstille en hoved-kjedepolymer med utstikkende OH-grupper ved kopolymerisering av en allylalkohol med 2 eller flere andre alkenisk umettede monomerer. According to one method, a main chain polymer with protruding OH groups can first be prepared by copolymerizing an allyl alcohol with 2 or more other alkenically unsaturated monomers.
De foretrukne monomerer er estere av énverdige alkoholer med 1-8 carbonatomer og acrylsyre eller methacrylsyre, f.eks. methyl-jnethacrylat, ethylacrylat, butylacrylat, butylmethacrylat, octyl-acrylat eller 2-ethylhexylacrylat. Alkoholer med flere carbonatomer, f.eks. 9-15, kan imidlertid også anvendes for fremstilling av slike estere. For enkelhets skyld vil slike estere av acrylsyre og methacrylsyre herefter bli betegnet som acrylater. Hydrocarbonmonomerer', f.eks. styren og alkylerte styrener, som vinyltoluen, a-methylstyren og lignende forbindelser, kan anvendes i kombinasjon med de ovenfor angitte acrylater. I forbindelse med de ovenfor angitte acrylatmonomerer og hydrocarbonmonomerer kan det anvendes små mengder av andre monomerer, som nitriler, f.eks. acrylonitril, acrylamid eller N-methylolacrylnitril, vinyl-halogenider, f.eks. vinylklorid, eller vinylcarboxylater, f.eks. vinylacetat. Ingen av de andre monomerer skal inngå i en større andel enn acrylatmonomeren. Kopolymeren er derfor i det følgende, også i kravet, betegnet "acrylpolymer(en)". The preferred monomers are esters of monohydric alcohols with 1-8 carbon atoms and acrylic acid or methacrylic acid, e.g. methyl methacrylate, ethyl acrylate, butyl acrylate, butyl methacrylate, octyl acrylate or 2-ethylhexyl acrylate. Alcohols with several carbon atoms, e.g. 9-15, however, can also be used for the production of such esters. For the sake of simplicity, such esters of acrylic acid and methacrylic acid will hereafter be referred to as acrylates. Hydrocarbon monomers', e.g. styrene and alkylated styrenes, such as vinyltoluene, α-methylstyrene and similar compounds, can be used in combination with the above-mentioned acrylates. In connection with the above-mentioned acrylate monomers and hydrocarbon monomers, small amounts of other monomers, such as nitriles, e.g. acrylonitrile, acrylamide or N-methylolacrylonitrile, vinyl halides, e.g. vinyl chloride, or vinyl carboxylates, e.g. vinyl acetate. None of the other monomers should be included in a greater proportion than the acrylate monomer. The copolymer is therefore referred to in the following, also in the claim, as "acrylic polymer(s)".
Allylalkoholen som anvendes for dannelse av kopolymeren, er som regel en allylalkohol med 3-10 carbonatomer, f.eks. allylalkohol, 2-methyl-2-propen-l-ol, cinnamylalkohol (3-vinyl-2-propen-l-ol), 2-fenyl-2-propen-l-ol og 9-decen~l-ol.De ovenfor angitte alkoholer kan inneholde alkylsubstituenter, hvorved antallet carbonatomer pr., molekyl kan stige til 14. The allyl alcohol used to form the copolymer is usually an allyl alcohol with 3-10 carbon atoms, e.g. allyl alcohol, 2-methyl-2-propen-l-ol, cinnamyl alcohol (3-vinyl-2-propen-l-ol), 2-phenyl-2-propen-l-ol and 9-decen~l-ol.The the above-mentioned alcohols may contain alkyl substituents, whereby the number of carbon atoms per molecule may rise to 14.
Kopolymeren omsettes derpå med en allylglycidylether for innføring av sidekjedene med alkenisk umettede grupper. Denne allylglycidylether inneholder vanligvis 6-13 carbonatomer, men den kan inneholde inntil 17 carbonatomer dersom etheren er dannet av en alkohol med inntil 14 carbonatomer og epiklorhydrin. Eksempler på slike forbindelser er allylglycidylether, 1-buten-glycidylether og glycidylethere dannet av de ovenfor angitte allylalkoholer. The copolymer is then reacted with an allyl glycidyl ether to introduce the side chains with alkenically unsaturated groups. This allyl glycidyl ether usually contains 6-13 carbon atoms, but it can contain up to 17 carbon atoms if the ether is formed from an alcohol with up to 14 carbon atoms and epichlorohydrin. Examples of such compounds are allyl glycidyl ether, 1-butene glycidyl ether and glycidyl ethers formed from the above-mentioned allyl alcohols.
Ifølge en annen fremgangsmåte kan acrylpolymeren fremstilles, idet de to trinn utføres i omvendt rekkefølge. Første trinn blir da kopolymerisering av en allylglycidylether og 2 eller flere andre alkenisk umettede monomerer. Disse monomerer er av samme type som beskrevet i forbindelse med den ovenfor første fremgangsmåte, dvs. at acrylatmonomeren skal være hovedkomponenten. According to another method, the acrylic polymer can be produced, the two steps being carried out in reverse order. The first step is then copolymerization of an allyl glycidyl ether and 2 or more other alkenically unsaturated monomers. These monomers are of the same type as described in connection with the above first method, i.e. that the acrylate monomer must be the main component.
I annet trinn blir kopolymerens glycidylgrupper omsatt med allylalkohol . In the second step, the copolymer's glycidyl groups are reacted with allyl alcohol.
Den ferdige lakk kan påføres på i og for seg kjent måte ved påsprøyting, påvalsing, dypping eller påhelling. Overtrekket påføres som regel i en slik mengde at det oppnås en film med en gjennomsnittlig tykkelse av 2,5-100 /t-m. The finished varnish can be applied in a manner known per se by spraying, rolling, dipping or pouring. The coating is usually applied in such an amount that a film with an average thickness of 2.5-100 /t-m is obtained.
Eksempel 1 Example 1
Det ble fremstilt en kopolymer fra følgende reagenser: A copolymer was prepared from the following reagents:
Samme mengde xylen som vekten av reagenser som skulle til-settes under det første reaksjonstrinn, ble innført i en reaktor forsynt med kondensator, termometer, omrører og skilletrakt. Xylenet ble oppvarmet til 100-120°C. De fire reagenser ble godt blandet og langsomt satt til det oppvarmede xylen gjennom en skilletrakt i løpet av 4 timer. Reaksjonsblandingen ble holdt ved denne temperatur i 1 - 2 timer efter avsluttet tilsetning, hvorefter blandingen ble avkjølt til værelsetemperatur. The same amount of xylene as the weight of reagents to be added during the first reaction step was introduced into a reactor equipped with a condenser, thermometer, stirrer and separatory funnel. The xylene was heated to 100-120°C. The four reagents were well mixed and slowly added to the heated xylene through a separatory funnel over 4 hours. The reaction mixture was kept at this temperature for 1 - 2 hours after the addition was finished, after which the mixture was cooled to room temperature.
I denne kopolymer ble så de umettede sidekjeder innført ved anvendelse av følgende utgangsmaterialer: In this copolymer, the unsaturated side chains were then introduced using the following starting materials:
En oppløsning av allylglycidyletheren og kaliumhydroxyd ble satt til kopolymeren ved værelsetemperatur. Blandingen ble derefter oppvarmet til en temperatur av 100-120°C. Denne temperatur ble opprettholdt i 7 timer, hvorefter blandingen ble avkjølt. Reaksjonsblandingen ble oppvarmet til ca. 60°C og xylenet og overskudd av reagenser fjernet ved vakuumdestillasjon. A solution of the allyl glycidyl ether and potassium hydroxide was added to the copolymer at room temperature. The mixture was then heated to a temperature of 100-120°C. This temperature was maintained for 7 hours, after which the mixture was cooled. The reaction mixture was heated to approx. 60°C and the xylene and excess reagents removed by vacuum distillation.
Styren og hydrokinon ble satt til polymeren ved en temperatur av ca. 60°C for dannelse av et bindemiddel med følgende sammensetning: Styrene and hydroquinone were added to the polymer at a temperature of approx. 60°C to form a binder with the following composition:
Denne oppløsning (bindemidlet) ble påført en metallplate i et lag med en gjennomsnittstykkelse av ca. 8 og derefter herdet ved anvendelse av en elektronstråle. Strålingsbetingelsene var: This solution (the binder) was applied to a metal plate in a layer with an average thickness of approx. 8 and then cured using an electron beam. The radiation conditions were:
Det ble oppnådd et utmerket lakkovertrekk. An excellent lacquer coating was achieved.
Eksempel 2 Example 2
Fremgangsmåten ifølge eksempel 1 ble gjentatt, men med den forandring at en ekvivalent mengde methylmethacrylat ble anvendt istedenfor styrenmonomeren i den ovenfor angitte filmdannende oppløsning. The procedure according to example 1 was repeated, but with the change that an equivalent amount of methyl methacrylate was used instead of the styrene monomer in the above-mentioned film-forming solution.
Eksempel 3 Example 3
Fremgangsmåten ifølge eksempel 1 ble gjentatt, men med den forandring at en ekvivalent mengde av en blanding av styren, ethylacrylat og 2-hexylacrylat ble anvendt istedenfor styrenet i den filmdannende oppløsning. The procedure according to example 1 was repeated, but with the change that an equivalent amount of a mixture of styrene, ethyl acrylate and 2-hexyl acrylate was used instead of the styrene in the film-forming solution.
Eksempel 4 Example 4
Fremgangsmåten ifølge eksempel 1 ble gjentatt, men med den forandring at en ekvimolekylær blanding av methylmethacrylat og vinyltoluen ble anvendt istedenfor styrenmonomeren i den filmdannende oppløsning og at blandingen ble påført en treplate som en film med en tykkelse av 25^ jt, m. Også her ble det oppnådd et utmerket resultat. The procedure according to example 1 was repeated, but with the change that an equimolecular mixture of methyl methacrylate and vinyltoluene was used instead of the styrene monomer in the film-forming solution and that the mixture was applied to a wooden board as a film with a thickness of 25 µm. It achieved an excellent result.
Eksempel 5 Example 5
Fremgangsmåten ifølge eksempel 1 ble gjentatt, men med den forandring at den filmdannende oppløsning inneholdt 3 0 vekt% av acrylpolymeren og 70 vekt% av en blanding av styren og butylmethacrylat. The procedure according to example 1 was repeated, but with the change that the film-forming solution contained 30% by weight of the acrylic polymer and 70% by weight of a mixture of styrene and butyl methacrylate.
Eksempel 6 Example 6
Fremgangsmåten ifølge eksempel 1 ble gjentatt, men med den forandring av den filmdannende oppløsning inneholdt 70 vekt% polymer og 30 vekt% av en blanding av a-methylstyren, ethylacrylat og butylacrylat. The procedure according to example 1 was repeated, but with the change that the film-forming solution contained 70% by weight of polymer and 30% by weight of a mixture of α-methylstyrene, ethyl acrylate and butyl acrylate.
Eksempel 7 Example 7
Fremgangsmåten ifølge eksempel 1 ble gjentatt med følgende forandringer: The procedure according to example 1 was repeated with the following changes:
(a) Reagensene i første reaksjonstrinn var: (b) Reagensene i annet reaksjonstrinn var: (c) Sammensetningen av den filmdannende oppløsning (bindemidlet) var: (a) The reagents in the first reaction step were: (b) The reagents in the second reaction step were: (c) The composition of the film-forming solution (binder) was:
Eksempel 8 Example 8
Fremgangsmåten ifølge eksempel 7 ble gjentatt, men med den forandring at en ekvivalent mengde 3-fenyl-2-propen-l-ol ble anvendt istedenfor l-penten-5-ol i det første reaksjonstrinn og 1-buten-glycidylether istedenfor allylglycidylether i det annet reaksjonstrinn, idet monomerene i oppløsningen var en ekvimolekylær blanding av styren og methylmethacrylat. The procedure according to example 7 was repeated, but with the change that an equivalent amount of 3-phenyl-2-propen-l-ol was used instead of l-penten-5-ol in the first reaction step and 1-butene glycidyl ether instead of allyl glycidyl ether in the second reaction step, the monomers in the solution being an equimolecular mixture of styrene and methyl methacrylate.
Eksempel 9 Example 9
Fremgangsmåten ifølge eksempel 7 ble gjentatt, men med den forandring at en ekvivalent mengde cinnamylglycidylether ble anvendt istedenfor allylglycidylether i det annet reaksjonstrinn og 9-de.cen -l-ol istedenfor l-penten-5-ol i det første reaksjonstrinn, idet monomerene i oppløsningen var en ekvimolekylær blanding av styren og methacrylat. The procedure according to example 7 was repeated, but with the change that an equivalent amount of cinnamyl glycidyl ether was used instead of allyl glycidyl ether in the second reaction step and 9-decen-1-ol instead of l-penten-5-ol in the first reaction step, as the monomers in the solution was an equimolecular mixture of styrene and methacrylate.
Eksempel 10 Example 10
Fremgangsmåten ifølge eksempel 7 ble gjentatt, men med den forandring at monomerene i første reaksjonstrinn og mengden av allylglycidylether i det annet reaksjonstrinn ble innstilt slik at det ble oppnådd en polymer med ca. 0,7 alkenisk umettede enheter pr. 1000 enheter molekylvekt og at monomerene i oppløsningen var en ekvimolekylær blanding av styren og methylmethacrylat. The procedure according to example 7 was repeated, but with the change that the monomers in the first reaction step and the amount of allyl glycidyl ether in the second reaction step were adjusted so that a polymer with approx. 0.7 alkenically unsaturated units per 1000 molecular weight units and that the monomers in the solution were an equimolecular mixture of styrene and methyl methacrylate.
Eksempel 11 Example 11
Fremgangsmåten ifølge eksempel 7 ble gjentatt, men med den forandring at monomerene i det første reaksjonstrinn og mengden av allylglycidylether i det annet reaksjonstrinn ble innstilt slik at det ble oppnådd en polymer med ca. 4,5 alkenisk umettede enheter pr. 1000 enheter molekylvekt og at monomerene i opp-løsningen var en ekvimolekylær blanding av styren og methylmethacrylat . The procedure according to example 7 was repeated, but with the change that the monomers in the first reaction step and the amount of allyl glycidyl ether in the second reaction step were adjusted so that a polymer with approx. 4.5 alkenically unsaturated units per 1000 molecular weight units and that the monomers in the solution were an equimolecular mixture of styrene and methyl methacrylate.
Eksempel 12 Example 12
Fremgangsmåten ifølge eksempel 7 ble gjentatt, men med den forandring av monomerene i det første reaksjonstrinn og mengden av allylglycidylether i det annet reaksjonstrinn ble innstilt slik at det ble oppnådd en polymer inneholdende ca. 1 alkenisk umettet enhet pr. 1000 enheter molekylvekt og at monomerene i opplesningen var en ekvimolekylær blanding av styren og methylmethacrylat. The procedure according to example 7 was repeated, but with the change of the monomers in the first reaction step and the amount of allyl glycidyl ether in the second reaction step was adjusted so that a polymer containing approx. 1 alkenic unsaturated unit per 1000 molecular weight units and that the monomers in the reading were an equimolecular mixture of styrene and methyl methacrylate.
Eksempel 13 Example 13
Fremgangsmåten ifølge eksempel 7 ble gjentatt, men med den forandring at monomerene i det første reaksjonstrinn og mengden av allylglycidylether i det annet reaksjonstrinn ble innstilt slik at det ble oppnådd en polymer inneholdende ca. 3 alkenisk umettede enheter pr. 1000 enheter molekylvekt og at monomerene The procedure according to example 7 was repeated, but with the change that the monomers in the first reaction step and the amount of allyl glycidyl ether in the second reaction step were adjusted so that a polymer containing approx. 3 alkenically unsaturated units per 1000 molecular weight units and that the monomers
i oppløsningen var en ekvimolekylær blanding av styren og methylmethacrylat . in the solution was an equimolecular mixture of styrene and methyl methacrylate.
Eksempel 14 Example 14
Fremgangsmåten ifølge eksempel 1 ble gjentatt med følgende forandringer: The procedure according to example 1 was repeated with the following changes:
(a) Reagensene i første reaksjonstrinn var: (a) The reagents in the first reaction step were:
(b) Reagensene i annet reaksjonstrinn var: (c) Sammensetning av den filmdannende oppløsning (bindemidlet) var: (b) The reagents in the second reaction step were: (c) Composition of the film-forming solution (binder) was:
Oppløsningens viskositet innstilles slik at den hurtig kan påføres en overflate i et passende jevnt lag, slik at det på en overflate kan opprettholdes et avsatt filmlag med en tykkelse av 0,08 mm uten avdrivning. Bindemidlets viskositet kan reguleres ved å variere de relative konsentrasjoner av de forskjellige monomerer. Bindemidlet anvendes fortrinnsvis uten innhold av organiske oppløsningsmidler eller andre bestanddeler som ikke kan polymerisere. The viscosity of the solution is set so that it can be quickly applied to a surface in a suitable even layer, so that a deposited film layer with a thickness of 0.08 mm can be maintained on a surface without drifting. The binder's viscosity can be regulated by varying the relative concentrations of the different monomers. The binder is preferably used without organic solvents or other components that cannot polymerize.
Eksempel 15 Example 15
Det ble fremstilt en kopolymer fra følgende reagenser: A copolymer was prepared from the following reagents:
I en reaktor forsynt med kondensator, termometer, omrører og skilletrakt ble det innført en xylenmengde som svarte til den mengde av reagenser som skulle innføres i det første reaksjonstrinn. Xylenet ble oppvarmet til 100-120°C. De fire reagenser ble godt blandet og langsomt satt til det oppvarmede xylen i løpet av 4 timer gjennom en skilletrakt. Reaksjonsblandingen ble holdt ved denne temperatur i 1-2 timer efter avsluttet tilsetning og derefter avkjølt til værelsetemperatur. In a reactor equipped with a condenser, thermometer, stirrer and separating funnel, a quantity of xylene corresponding to the quantity of reagents to be introduced in the first reaction step was introduced. The xylene was heated to 100-120°C. The four reagents were well mixed and slowly added to the heated xylene over 4 hours through a separatory funnel. The reaction mixture was kept at this temperature for 1-2 hours after the addition was finished and then cooled to room temperature.
Det ble dannet en bindemiddelpolymer i et annet reaksjonstrinn fra følgende utgangsmaterialer: A binder polymer was formed in a second reaction step from the following starting materials:
En oppløsning av allylalkohol og kaliumhydroxyd ble satt A solution of allyl alcohol and potassium hydroxide was added
til kopolymeren ved værelsetemperatur. Blandingen ble oppvarmet til 100-120°C. Denne temperatur ble opprettholdt i 7 timer, hvor- to the copolymer at room temperature. The mixture was heated to 100-120°C. This temperature was maintained for 7 hours, during which
efter blandingen ble avkjølt. Reaksjonsblandingen ble derefter opp-oppvarmet til ca. 6 0°C og xylenet og overskudd av reagenser fjernet ved vakuumdestillasjon. after the mixture was cooled. The reaction mixture was then heated to approx. 6 0°C and the xylene and excess reagents removed by vacuum distillation.
Styren og hydrokinon ble ved en temperatur av ca. 60°C satt til polymeren for dannelse av en filmdannende oppløsning med føl-gende sammensetning: Styrene and hydroquinone were at a temperature of approx. 60°C added to the polymer to form a film-forming solution with the following composition:
Den filmdannende oppløsning ble påført en metalloverflate som et lag med en tykkelse av ca 8 |im og derefter herdet ved be-stråling med en elektronstråle. Strålingsbetingelsene var: The film-forming solution was applied to a metal surface as a layer with a thickness of about 8 µm and then cured by irradiation with an electron beam. The radiation conditions were:
Eksempel 16 Example 16
Fremgangsmåte ifølge eksempel 15 ble gjentatt med følgende forandringer: The procedure according to example 15 was repeated with the following changes:
(a) Reagensene i første reaksjonstrinn var: (a) The reagents in the first reaction step were:
(b) Reagensene i annet reaksjonstrinn var: (c) Sammensetning av den filmdannende oppløsning var: (b) The reagents in the second reaction step were: (c) Composition of the film-forming solution was:
Eksempel 17 Example 17
Fremgangsmåten ifølge eksempel 15 ble gjentatt med følgende forandringer: The procedure according to example 15 was repeated with the following changes:
(a) Reagensene i første reaksjonstrinn var: (a) The reagents in the first reaction step were:
Også ved samtlige eksempler 5 til 17 ble utmerkede resul-tater oppnådd. Excellent results were also obtained in all examples 5 to 17.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US77334568A | 1968-11-04 | 1968-11-04 | |
US77334668A | 1968-11-04 | 1968-11-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
NO133326B true NO133326B (en) | 1976-01-05 |
NO133326C NO133326C (en) | 1976-04-12 |
Family
ID=27118744
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO433969A NO133326C (en) | 1968-11-04 | 1969-11-03 |
Country Status (6)
Country | Link |
---|---|
DE (1) | DE1955377C3 (en) |
FI (1) | FI49057C (en) |
FR (1) | FR2022492B1 (en) |
GB (1) | GB1221889A (en) |
NL (1) | NL6916535A (en) |
NO (1) | NO133326C (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4274992A (en) * | 1979-12-11 | 1981-06-23 | Ppg Industries, Inc. | Low temperature curing polyester resins and coating compositions |
CA1306321C (en) * | 1986-03-05 | 1992-08-11 | Rhom And Haas Company | Modified solution polymers for coatings, films, mastics, caulks andadhesives |
-
1969
- 1969-08-22 GB GB4191969A patent/GB1221889A/en not_active Expired
- 1969-09-18 FR FR6931767A patent/FR2022492B1/fr not_active Expired
- 1969-11-03 NO NO433969A patent/NO133326C/no unknown
- 1969-11-03 NL NL6916535A patent/NL6916535A/xx unknown
- 1969-11-03 FI FI315469A patent/FI49057C/en active
- 1969-11-04 DE DE19691955377 patent/DE1955377C3/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
FR2022492A1 (en) | 1970-07-31 |
NO133326C (en) | 1976-04-12 |
NL6916535A (en) | 1970-05-08 |
FR2022492B1 (en) | 1974-05-31 |
FI49057C (en) | 1975-03-10 |
DE1955377B2 (en) | 1973-12-20 |
DE1955377A1 (en) | 1970-07-30 |
DE1955377C3 (en) | 1978-08-31 |
FI49057B (en) | 1974-12-02 |
GB1221889A (en) | 1971-02-10 |
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