NO117596B - - Google Patents
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- NO117596B NO117596B NO15226964A NO15226964A NO117596B NO 117596 B NO117596 B NO 117596B NO 15226964 A NO15226964 A NO 15226964A NO 15226964 A NO15226964 A NO 15226964A NO 117596 B NO117596 B NO 117596B
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- 239000000047 product Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 15
- 150000005846 sugar alcohols Polymers 0.000 claims description 13
- 229920000180 alkyd Polymers 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 239000002966 varnish Substances 0.000 claims description 6
- 125000005442 diisocyanate group Chemical group 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 5
- 238000007334 copolymerization reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 238000005809 transesterification reaction Methods 0.000 description 7
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 235000021388 linseed oil Nutrition 0.000 description 5
- 239000000944 linseed oil Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 241000779819 Syncarpia glomulifera Species 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- ZDCHZHDOCCIZIY-UHFFFAOYSA-N phthalic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OC(=O)C1=CC=CC=C1C(O)=O ZDCHZHDOCCIZIY-UHFFFAOYSA-N 0.000 description 2
- 239000001739 pinus spp. Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KQTIIICEAUMSDG-UHFFFAOYSA-N tricarballylic acid Chemical compound OC(=O)CC(C(O)=O)CC(O)=O KQTIIICEAUMSDG-UHFFFAOYSA-N 0.000 description 2
- 229940036248 turpentine Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FYWJWWMKCARWQG-UHFFFAOYSA-N 1,2-dichloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1Cl FYWJWWMKCARWQG-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- BFRLRGJQKQUFHK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;phthalic acid Chemical compound OCC(CO)(CO)CO.OC(=O)C1=CC=CC=C1C(O)=O BFRLRGJQKQUFHK-UHFFFAOYSA-N 0.000 description 1
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
- 241000273930 Brevoortia tyrannus Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920001175 Glycerine phthalate Polymers 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 244000124853 Perilla frutescens Species 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 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
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 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
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MHIBEGOZTWERHF-UHFFFAOYSA-N heptane-1,1-diol Chemical compound CCCCCCC(O)O MHIBEGOZTWERHF-UHFFFAOYSA-N 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Description
Fremgangsmåte for fremstilling av råstoffer for lakker. Procedure for the production of raw materials for varnishes.
Det er kjent å føre inn uretanoljer i blandede estere av flerverdige alkoholer og polykarbonsyrer og å sampolymerisere de blandede estere med umettede kullvannstoffer som inneholder minst 1 gruppe -CH=CHR, som f. eks. vinylforbindelser som styrol. Man kom-mer til lignende produkter også når man fo-retar innføringen av uretangruppen og poly-meriseringen av de blandede estere med de umettede kullvannstoffer i en annen rekke-følge enn den angitte eller samtidig. It is known to introduce virgin ethanol into mixed esters of polyhydric alcohols and polycarboxylic acids and to copolymerize the mixed esters with unsaturated hydrocarbons containing at least 1 group -CH=CHR, such as e.g. vinyl compounds such as styrene. Similar products are also obtained when the introduction of the urethane group and the polymerization of the mixed esters with the unsaturated hydrocarbons are carried out in a different order than that specified or at the same time.
De produkter som kan fåes ved hjelp av disse kjente fremgangsmåter er verdifulle råstoffer for lakker og har vist seg fordelaktige for mange anvendelsesformål. The products that can be obtained by means of these known methods are valuable raw materials for varnishes and have proven to be advantageous for many applications.
Det er nu funnet at man kan fremstille It has now been found that one can produce
lakkråstoffer med særlig mangesidig anven-delse og på basis av sampolymerisasjonspro-dukter av a) blandede estere av flerverdige alkoholer og polykarbonsyrer, hvilke estere inneholder radikaler av umettede fettsyrer og uretangrupper, og b) umettede kullvannstoffer som inneholder minst en gruppe -CH= CHR i molekylet derved at man først sampo-lymiserer blandede estere av flerverdige alkoholer og polykarbonsyrer, som inneholder radikaler av umettede fettsyrer, på i og for seg kjent måte med umettede kullvannstoffer av nevnte art, derpå omestrer polymerisasjons-produktet med en polyalkohol, fortrinsvis et omestringsprodukt av en polyalkohol med en tørrende olje eller med en oljemodifisert alkydharpiks med frie hydroksylgrupper varnish raw materials with particularly versatile use and based on copolymerization products of a) mixed esters of polyhydric alcohols and polycarboxylic acids, which esters contain radicals of unsaturated fatty acids and urethane groups, and b) unsaturated hydrocarbons containing at least one group -CH= CHR in the molecule by first copolymerizing mixed esters of polyhydric alcohols and polycarboxylic acids, which contain radicals of unsaturated fatty acids, in a manner known per se with unsaturated hydrocarbons of the aforementioned kind, then transesterifying the polymerization product with a polyalcohol, preferably a transesterification product of a polyalcohol with a drying oil or with an oil-modified alkyd resin with free hydroxyl groups
og sluttelig som i og for seg kjent omsetter det herved erholdte produkt i nærvær eller fravær av oppløsningsmidler med et isocyanat and finally, as is known in and of itself, reacts the product thus obtained in the presence or absence of solvents with an isocyanate
eller diisocyanat, fortrinnsvis under gradvis tilsetning av sistnevnte forbindelse og ved temperaturer mellom 130 og 200° C. or diisocyanate, preferably during the gradual addition of the latter compound and at temperatures between 130 and 200°C.
De nye lakkråstoffer utmerker seg ved en rekke verdifulle egenskaper, nemlig ved et lavt syretall og derav følgende god foren-lighet av lakkene med basiske pigmenter, ved en raskt begynnende tørring og gjennomtør-ring av overtrekk som er fremstillet av samme og hermed forbundet god strykbarhet uten at lakkene trekkes opp fra underlaget, samt sluttelig ved god vedheftning, høy elastisitet, fremtredende glans og høy bestandighet mot vann og klimaets innvirkning av de resulter-ende overtrekk. The new lacquer raw materials are distinguished by a number of valuable properties, namely by a low acid number and the resulting good compatibility of the lacquers with basic pigments, by a quick drying and thorough drying of the top coat made from the same and associated good ironability without the varnishes being pulled up from the substrate, and finally by good adhesion, high elasticity, prominent gloss and high resistance to water and the impact of the climate of the resulting coatings.
Som nevnt anvendes fortrinsvis omestringsprodukter av flerverdige alkoholer med tørrende oljer til omforestring av de sampo-lymeriserte blandede estere og denne anvendel-se har den fordel at nye aktive dobbeltbindin-ger som er nødvendig for den oksydative tør-ring innføres i harpiksen, hvorved en særlig rask gjennomtørring av hinner fremstillet av disse harpikser oppnås. De umettede grupper som opprinnelig er tilstede i de med olje mo-difiserte alkydharpikser blir nemlig for den største del forbrukt ved sampolymeriserin-gen. As mentioned, transesterification products of polyhydric alcohols with drying oils are preferably used for transesterification of the copolymerized mixed esters, and this use has the advantage that new active double bonds which are necessary for the oxidative drying are introduced into the resin, whereby a particular rapid drying of films made from these resins is achieved. The unsaturated groups which are originally present in the oil-modified alkyd resins are for the most part consumed during the copolymerisation.
Mens man hittil i regelen har foretatt re-aksjonen mellom hydroksylgruppeholdige estere eller blandede estere og isocyanater eller diisocyanater ved temperaturer under omkring 130° C foretas i fremgangsmåten iføl-ge oppfinnelsen den avsluttende reaksjon av harpiksene med disse stoffer som nevnt fortrinnsvis ved temperaturer mellom omkring 130° C og omkring 200° C. Herved oppnås at den økning av viskositeten som i alminnelig-het finner sted i estere behandlet med isocyanater unngås selv ved lengere tids lagring. While up to now the reaction between hydroxyl group-containing esters or mixed esters and isocyanates or diisocyanates has usually been carried out at temperatures below about 130° C, in the method according to the invention the final reaction of the resins with these substances as mentioned is preferably carried out at temperatures between about 130 ° C and around 200 ° C. This achieves that the increase in viscosity which generally takes place in esters treated with isocyanates is avoided even during longer storage.
Til fremstilling av de blandede estere kan man f. eks. bruke: Polykarbonsyrer som ravsyre, glutarsyre, adipinsyre, ftalsyre, maleinsyre, trikarballyl-syre, sitronsyre samt anhydrider og blandinger av disse syrer; For the production of the mixed esters, one can e.g. use: Polycarbonic acids such as succinic acid, glutaric acid, adipic acid, phthalic acid, maleic acid, tricarballylic acid, citric acid as well as anhydrides and mixtures of these acids;
Polyalkoholer som glykol, dietylenglykol, propandiol, butandiol, heptandiol, heksandiol, glycerin, trimetylolpropan, trimetyloletan, heksantriol, pentaerytrit, sorbit og mannit samt blandinger av disse stoffer; Polyalcohols such as glycol, diethylene glycol, propanediol, butanediol, heptanediol, hexanediol, glycerin, trimethylolpropane, trimethylolethane, hexanetriol, pentaerythritol, sorbitol and mannitol as well as mixtures of these substances;
umettede fettsyrer eller glycerider av så-danne, som linolje, perillaolje, dehydratisert risinusolje, soyaolje, jordnøttolje, valmueolje, levertran, olje av Sardinia coérulea, menha-denolje og andre fiskeoljer, treolje og oiticica-olje, såvel som blandinger av disse oljer. unsaturated fatty acids or glycerides thereof, such as linseed oil, perilla oil, dehydrated castor oil, soybean oil, peanut oil, poppy seed oil, cod liver oil, oil of Sardinia coérulea, menhaden oil and other fish oils, tree oil and oiticica oil, as well as mixtures of these oils.
De blandede estere kan innenfor oppfin-nelsens ramme sampolymeriseres f. eks. med følgende umettede kullvannstoffer: Vinylklorid, vinylacetat, akrylsyreestere, metalkrylsyreestere, styrol og dets substitu-sjonsprodukter, som «-metylstyrol eller di-klorstyrol, divinylbenzol, butadien, isopren, inden, kumaron, cykloheksadien, cyklopentadien og dets lavere polymer, som dicyklopentadien. Within the framework of the invention, the mixed esters can be copolymerized, e.g. with the following unsaturated hydrocarbons: Vinyl chloride, vinyl acetate, acrylic acid esters, metal acrylic acid esters, styrene and its substitution products, such as "-methylstyrene or dichlorostyrene, divinylbenzene, butadiene, isoprene, indene, coumarone, cyclohexadiene, cyclopentadiene and its lower polymer, such as dicyclopentadiene.
Til omestringen av sampolymerisasjons-produktene kan det brukes de allerede nevnte polyalkoholer, men fortrinnsvis disse polyal-koholers omestringsprodukter med de likele-des ovenfor nevnte tørrende oljer, sistnevnte også i form av deres stamoljer eller etter be-handling med luft, surstoff, svovel, svoveldi-oksyd, antrakinon eller maleinsyreanhydrid. For the transesterification of the copolymerization products, the already mentioned polyalcohols can be used, but preferably the transesterification products of these polyalcohols with the likewise above-mentioned drying oils, the latter also in the form of their base oils or after treatment with air, oxygen, sulphur, sulfur dioxide, anthraquinone or maleic anhydride.
Som de isocyanater eller diisocyanater som kan brukes nevnes eksempelvis: Fenylisocyanat, diklorfenylisocyanat, cy-kloheksylicocyanat, klorfenyl-2-4-diisocyanat, totuylendiisocyanat og 1, 6-lieksametylendiiso-cyanat. As the isocyanates or diisocyanates which can be used, examples are mentioned: Phenyl isocyanate, dichlorophenyl isocyanate, cyclohexyl isocyanate, chlorophenyl-2-4-diisocyanate, totuylendiisocyanate and 1,6-liexamethylene diisocyanate.
I det følgende beskrives som eksempler noen utførelsesformer for oppfinnelsen: In the following, some embodiments of the invention are described as examples:
Eksempel 1. Example 1.
Man lar en blanding av 6645 vektsdeler av en pentaerytritftalatharpiks modifisert med linolje og med et oljeinnhold på 73,7 % syretall 6,27 og viskositet 43,2 sek. målt i 70 %'s oppløsning i lakkbensin i Ford-beger nr. A mixture of 6645 parts by weight of a pentaerythritol phthalate resin modified with linseed oil and with an oil content of 73.7%, acid number 6.27 and viscosity 43.2 sec. measured in 70% solution in white spirit in Ford beaker no.
4 ved 20° C og 4440 vektsdeler av en glycerin-ftalatharpiks modifisert med dehydratisert risinusolje og med et oljeinhold på 64 %, syretall 8,4 og viskositet 172 sek. målt i 50 %'s oppløsning i lakkbensin reagere med 5215 vektsdeler monomert styrol i løpet av 28 timer ved 200° C, f. eks. etter fremgangsmåten 4 at 20° C and 4440 parts by weight of a glycerin phthalate resin modified with dehydrated castor oil and with an oil content of 64%, acid number 8.4 and viscosity 172 sec. measured in a 50% solution in white spirit react with 5215 parts by weight of monomeric styrene during 28 hours at 200° C, e.g. according to the procedure
ifølge tysk patent 897 016. Man får et produkt med følgende karakteristiske verdier: Total oljeinnhold 47,5 %, styrolinnhold 32,0% innhold av faste stoffer 95,0%,syretall according to German patent 897 016. You get a product with the following characteristic values: Total oil content 47.5%, styrene content 32.0% solids content 95.0%, acid number
5,98, viskositet i 50 %'s oppløsning i bensin 5.98, viscosity in 50% solution in petrol
55,3 sek. målt i Ford-beger nr. 4 ved 20° C. 55.3 sec. measured in Ford beaker No. 4 at 20°C.
En klar lakk fremstillet av dette produkt etter tilsetning av sikkativer til samme tørrer A clear varnish produced from this product after the addition of siccatives to the same drier
i løpet av 7 timer til hård og ikke klebende tilstand. within 7 hours to a hard and non-sticky state.
915 vektsdeler av denne med styrol be-handlede oljemodifiserte blandede alkydharpiks lar man nu i overensstemmelse med oppfinnelsen reagere med 17 vektsdeler trimetylolpropan i omkring 1 time ved 240° C. Etter avkjøling til 130° C tilsettes 20,5 vektsdeler toluylendiisocyanat og blandingen oppvarmes 915 parts by weight of this styrene-treated oil-modified mixed alkyd resin is now, in accordance with the invention, allowed to react with 17 parts by weight of trimethylolpropane for about 1 hour at 240° C. After cooling to 130° C, 20.5 parts by weight of toluylene diisocyanate are added and the mixture is heated
derpå 3 timer til 180 ° C. Etter av-kjøling påny til 130° C tilsettes ytterligere 10.1 vektsdeler toluylendiisocyanat og massen opphetes derpå 6 timer til 130° C. Man får et produkt med syretall 1,7 og viskositet 360 sekunder målt i 50 %'s oppløsning i lakkbensin i Ford-beger nr. 4 ved 20° C. then 3 hours to 180° C. After cooling again to 130° C, a further 10.1 parts by weight of toluylene diisocyanate are added and the mass is then heated for 6 hours to 130° C. A product with an acid value of 1.7 and a viscosity of 360 seconds measured in 50% is obtained 's solution in white spirit in Ford beaker No. 4 at 20° C.
En klar lakk fremstillet av dette produkt etter tilsetning av sikkativer tørrer i løpet av 3 timer til en overordentlig bestandig, godt vedheftende, hård, elastisk skinnende og ikke klebende hinne, d.v.s. 4 timer raskere enn den styrolbehandlede alkydharpiksblanding før denne ble viderebehandlet ifølge oppfinnelsen. A clear lacquer produced from this product after the addition of siccatives dries within 3 hours to an extremely durable, well-adherent, hard, elastic shiny and non-sticky film, i.e. 4 hours faster than the styrene-treated alkyd resin mixture before it was further processed according to the invention.
Eksempel 2. Example 2.
776 vektsdeler av en styrol-alkydharpiks av ftalsyreanhydrid og glycerin erholdt etter fremgangsmåten ifølge tysk patent 897.016 og med et linoljeinnhold på omkring 34 %, et styrolinnhold på omkring 45 %, syretall 6,7 og viskositet 113 sek. målt i 50 %'s opp-løsning i lakkbensin i Ford-beger nr. 4 ved 20° C oppvarmes med 142 vektsdeler av en omestringsblanding erholdt av 2180 vektsdeler linolje og 670 vektsdeler trimetylolpropan ved 260° C, oppvarmningen foretas 1 time ved 200° C under gjennomledning av nitro-gen som beskyttende gass. Derpå fortynnes med 350 vektsdeler lakkbensin. Under omrør-ing og koking under tilbakeløpskjøling ved temperaturer på 155-165° C tildryppes nu en blanding av 52 vektsdeler 1,6-heksametylendiisocyanat og 152 vektsdeler lakkbensin kon-tinuerlig i løpet av 5 timer. For å oppnå full-stendig reaksjon oppvarmes det ytterligere en time til koketemperatur. Man får en omkring 67 %'s oppløsning av en med isocyanat modifisert styrol-alkydharpiks med syretall 1,26, viskositet 290 sekunder målt i 50 %'s oppløsning i lakkbensin i Ford-beger nr. 4 og et oljeinnhold på omkring 39 %. 776 parts by weight of a styrene-alkyd resin of phthalic anhydride and glycerin obtained according to the method according to German patent 897,016 and with a linseed oil content of about 34%, a styrene content of about 45%, acid number 6.7 and viscosity 113 sec. measured in a 50% solution in white spirit in Ford beaker No. 4 at 20° C. is heated with 142 parts by weight of a transesterification mixture obtained from 2180 parts by weight of linseed oil and 670 parts by weight of trimethylolpropane at 260° C, the heating is carried out for 1 hour at 200° C under the passage of nitrogen as protective gas. Then dilute with 350 parts by weight of white spirit. During stirring and boiling under reflux cooling at temperatures of 155-165° C, a mixture of 52 parts by weight of 1,6-hexamethylene diisocyanate and 152 parts by weight of white spirit is now added drop by drop over the course of 5 hours. In order to achieve a complete reaction, it is heated for a further hour to boiling temperature. An approximately 67% solution of an isocyanate-modified styrene-alkyd resin with an acid number of 1.26, viscosity 290 seconds measured in a 50% solution in white spirit in Ford beaker No. 4 and an oil content of approximately 39% is obtained.
En klarlakk fremstillet av dette produkt etter tilsetning av sikkativer gir meget hårde skinnende, mot vann og alkalier bestandige elastiske og godt vedheftende hinner som på 1 time, d.v.s. 2 timer raskere enn den har-piks man gikk ut fra, tørrer til klebefri tilstand med høy glans. A clear coat made from this product after the addition of siccatives gives very hard shiny, water and alkali resistant, elastic and well-adherent films which in 1 hour, i.e. 2 hours faster than the starting har-pix, dries to a non-sticky state with a high gloss.
Eksempel 3 Example 3
En oppløsning i 109 vektsdeler terpentin av 3240 vektsdeler av en glyserinftalatharpiks modifisert med linolje og med oljeinnhold omkring 55 %, syretall 8,4 og viskositet 70 sek. målt i 40 %'s oppløsning i lakkbensin i Ford-beger nr. 4 ved 20° C oppvarmes under omrø-ring og tilbakeløpskjøling til 200° C. Derpå innsprøytes jevnt med en innspøytningspumpe 207 vektsdeler dicyklopentadien i løpet av 7 timer. Etter 1 time tilsettes 231 vektsdeler av den i eksempel 2 angitte omestringsblanding. Etter tilsetning av 72 vektsdeler terpentin oppvarmes det 1 time under tilbakeløpskjøling hvorpå det avkjøles til 180° C. I løpet av 9 timer tilsettes derpå jevnt 133,3 vektsdeler 1,6 heksametylendiisocyanat i 9 like store por-sjoner ved 180° C. Det erholdte produkt har syretall 3.42, viskositet 135 sek. målt i 40 %'s oppløsning i lakkbensin i Ford-beger nr. 4 ved 20° C samt et innhold av faste stoffer på 94,4 %. A solution in 109 parts by weight of turpentine of 3240 parts by weight of a glycerine phthalate resin modified with linseed oil and with an oil content of about 55%, acid number 8.4 and viscosity 70 sec. measured in a 40% solution in white spirit in Ford beaker No. 4 at 20° C. is heated with stirring and refluxed to 200° C. Then 207 parts by weight of dicyclopentadiene are injected evenly with an injection pump over the course of 7 hours. After 1 hour, 231 parts by weight of the transesterification mixture specified in example 2 are added. After adding 72 parts by weight of turpentine, it is heated for 1 hour under reflux, after which it is cooled to 180° C. During 9 hours, 133.3 parts by weight of 1,6 hexamethylene diisocyanate are then added evenly in 9 equal portions at 180° C. The obtained product has acid number 3.42, viscosity 135 sec. measured in a 40% solution in white spirit in Ford beaker No. 4 at 20° C and a solids content of 94.4%.
Klarlakker fremstillet av dette produkt etter tilsetning av sikkativer tørrer i løpet av 3 timer til hårde skinnende, godt vedheftende og ikke klebende hinner og dermed omkring 5 timer raskere enn hinner av den alkydharpiks man gikk ut fra, samt omkring 3 timer raskere enn hinner av reaksjonsproduktet av utgangsmaterialet og cyklopentadien. Clearcoats made from this product after the addition of siccatives dry within 3 hours to hard, shiny, well-adherent and non-sticky films and thus about 5 hours faster than films from the alkyd resin used as a starting point, and about 3 hours faster than films from the reaction product of the starting material and cyclopentadiene.
Claims (1)
Priority Applications (23)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE626083D BE626083A (en) | 1964-03-04 | ||
FR91357D FR91357E (en) | 1964-03-04 | ||
FR927151A FR1349796A (en) | 1962-03-09 | 1963-03-07 | Electronic telegraph relay |
CH1507663A CH419235A (en) | 1962-12-14 | 1963-12-10 | Electronic switch circuit |
DEJ24920A DE1200356B (en) | 1964-03-04 | 1963-12-12 | Circuit arrangement for the electronic simulation of a telegraph relay for double current operation |
FR957157A FR84981E (en) | 1963-05-07 | 1963-12-13 | Electronic telegraph relay |
NO15226964A NO117596B (en) | 1964-03-04 | 1964-03-04 | |
DEST22574A DE1219070B (en) | 1964-03-04 | 1964-08-22 | Circuit arrangement for the electronic simulation of a telegraph relay |
DE19651562286 DE1562286B1 (en) | 1964-03-04 | 1965-02-27 | Electronic telegraph relays |
SE2583/65A SE301177B (en) | 1964-03-04 | 1965-02-27 | |
US436537A US3359433A (en) | 1964-03-04 | 1965-03-02 | Electronic telegraph relay |
FR7888A FR89952E (en) | 1962-12-14 | 1965-03-04 | Electronic telegraph relay |
NL6502782A NL6502782A (en) | 1964-03-04 | 1965-03-04 | |
DE1965ST024200 DE1233006C2 (en) | 1964-03-04 | 1965-07-30 | Electronic telegraph relay for either single or double current operation |
US480314A US3445783A (en) | 1964-03-04 | 1965-08-17 | Circuit arrangement for the electronic simulation of a telegraph relay |
SE10770/65A SE333750B (en) | 1964-03-04 | 1965-08-18 | |
NL6510854A NL6510854A (en) | 1964-03-04 | 1965-08-19 | |
FR28964A FR90507E (en) | 1964-03-04 | 1965-08-20 | Electronic telegraph relay |
BE668542D BE668542A (en) | 1964-03-04 | 1965-08-20 | |
GB35917/65A GB1100620A (en) | 1964-03-04 | 1965-08-20 | Electronic relay |
NL6610539A NL6610539A (en) | 1964-03-04 | 1966-07-27 | |
BE684765D BE684765A (en) | 1964-03-04 | 1966-07-29 | |
SE10354/66A SE341758B (en) | 1964-03-04 | 1966-07-29 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO15226964A NO117596B (en) | 1964-03-04 | 1964-03-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO117596B true NO117596B (en) | 1969-09-01 |
Family
ID=19908928
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO15226964A NO117596B (en) | 1962-03-09 | 1964-03-04 |
Country Status (1)
Country | Link |
---|---|
NO (1) | NO117596B (en) |
-
1964
- 1964-03-04 NO NO15226964A patent/NO117596B/no unknown
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