SE458119B - Saett att framstaella ett hydrolyserbart polyesterharts - Google Patents
Saett att framstaella ett hydrolyserbart polyesterhartsInfo
- Publication number
- SE458119B SE458119B SE8205838A SE8205838A SE458119B SE 458119 B SE458119 B SE 458119B SE 8205838 A SE8205838 A SE 8205838A SE 8205838 A SE8205838 A SE 8205838A SE 458119 B SE458119 B SE 458119B
- Authority
- SE
- Sweden
- Prior art keywords
- acid
- glycol
- carbon atoms
- group
- integer
- Prior art date
Links
- 239000004645 polyester resin Substances 0.000 title description 15
- 229920001225 polyester resin Polymers 0.000 title description 14
- 238000004519 manufacturing process Methods 0.000 title description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 55
- 229910052751 metal Inorganic materials 0.000 claims description 39
- 239000002184 metal Substances 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 21
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 20
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 16
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 14
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 12
- 125000002009 alkene group Chemical group 0.000 claims description 11
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 9
- 238000006068 polycondensation reaction Methods 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 229940014800 succinic anhydride Drugs 0.000 claims description 9
- 150000005846 sugar alcohols Polymers 0.000 claims description 9
- 229910052725 zinc Inorganic materials 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims description 7
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052749 magnesium Inorganic materials 0.000 claims description 7
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052745 lead Inorganic materials 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 229910052742 iron Inorganic materials 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052748 manganese Inorganic materials 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 229910052718 tin Inorganic materials 0.000 claims description 4
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 3
- 229940114072 12-hydroxystearic acid Drugs 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052788 barium Inorganic materials 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 2
- 229960003656 ricinoleic acid Drugs 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims 2
- CKSWVWXSISYEJF-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol ethene Chemical compound C=C.C=C.CC(C)(CO)CO CKSWVWXSISYEJF-UHFFFAOYSA-N 0.000 claims 1
- 241000982822 Ficus obtusifolia Species 0.000 claims 1
- 239000004471 Glycine Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000003973 paint Substances 0.000 description 46
- 239000007787 solid Substances 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000000576 coating method Methods 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 22
- 230000007062 hydrolysis Effects 0.000 description 21
- 238000006460 hydrolysis reaction Methods 0.000 description 21
- 229920005989 resin Polymers 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- 239000011248 coating agent Substances 0.000 description 19
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 18
- -1 aliphatic dicarboxylic acids Chemical class 0.000 description 18
- 239000008096 xylene Substances 0.000 description 18
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 16
- 239000004922 lacquer Substances 0.000 description 15
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 15
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 14
- 229940117969 neopentyl glycol Drugs 0.000 description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 11
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 11
- 239000001361 adipic acid Substances 0.000 description 11
- 235000011037 adipic acid Nutrition 0.000 description 11
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 11
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 11
- 229920000728 polyester Polymers 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 239000002966 varnish Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000010949 copper Substances 0.000 description 9
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 8
- 239000011717 all-trans-retinol Substances 0.000 description 8
- 235000019169 all-trans-retinol Nutrition 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- BFWMWWXRWVJXSE-UHFFFAOYSA-M fentin hydroxide Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(O)C1=CC=CC=C1 BFWMWWXRWVJXSE-UHFFFAOYSA-M 0.000 description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 8
- 239000011701 zinc Substances 0.000 description 8
- 235000014692 zinc oxide Nutrition 0.000 description 8
- 239000011787 zinc oxide Substances 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 7
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 7
- 229940112669 cuprous oxide Drugs 0.000 description 7
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 7
- 229920000940 maneb Polymers 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 6
- 239000013535 sea water Substances 0.000 description 6
- OEHWSASCXNQLJM-UHFFFAOYSA-N C(CCC)[Sn](CCCC)=O.C(C1=CC=CC=C1)(=O)O Chemical compound C(CCC)[Sn](CCCC)=O.C(C1=CC=CC=C1)(=O)O OEHWSASCXNQLJM-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- DFNPRTKVCGZMMC-UHFFFAOYSA-M tributyl(fluoro)stannane Chemical compound CCCC[Sn](F)(CCCC)CCCC DFNPRTKVCGZMMC-UHFFFAOYSA-M 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- FOEZMJUMFMJRKV-FPLPWBNLSA-N (Z)-2-(6-hydroxyhexyl)but-2-enedioic acid Chemical compound C(CCCO)CC/C(=C/C(=O)O)/C(=O)O FOEZMJUMFMJRKV-FPLPWBNLSA-N 0.000 description 4
- UJIHVZPVGXBWJZ-WAYWQWQTSA-N (Z)-4-(6-hydroxyhexoxy)-4-oxobut-2-enoic acid Chemical compound C(CCCOC(=O)/C=C\C(=O)O)CCO UJIHVZPVGXBWJZ-WAYWQWQTSA-N 0.000 description 4
- DCSUDZUKLZFYHY-UHFFFAOYSA-N 2-benzofuran-1,3-dione;octadecanoic acid Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1.CCCCCCCCCCCCCCCCCC(O)=O DCSUDZUKLZFYHY-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- TYBKOVLWQWMOCI-UHFFFAOYSA-N but-1-ene-1,3-diol Chemical compound CC(O)C=CO TYBKOVLWQWMOCI-UHFFFAOYSA-N 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 239000011133 lead Substances 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229940059574 pentaerithrityl Drugs 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229940066675 ricinoleate Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- GAXWCZDVGSRIQK-UHFFFAOYSA-L C(CCC)[Sn](CCCC)(CCCC)F.C1(=CC=CC=C1)[Sn](C1=CC=CC=C1)(C1=CC=CC=C1)Cl Chemical compound C(CCC)[Sn](CCCC)(CCCC)F.C1(=CC=CC=C1)[Sn](C1=CC=CC=C1)(C1=CC=CC=C1)Cl GAXWCZDVGSRIQK-UHFFFAOYSA-L 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000007875 V-40 Substances 0.000 description 3
- 230000003373 anti-fouling effect Effects 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229940052303 ethers for general anesthesia Drugs 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000012260 resinous material Substances 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- 239000003440 toxic substance Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QNSFQIRYXVVLGT-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;2-ethyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(C)(C)CO.CCC(CO)(CO)CO QNSFQIRYXVVLGT-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- FFJFEOOXVXIRMN-UHFFFAOYSA-N 2-(6-hydroxyhexoxycarbonyl)benzoic acid Chemical compound OCCCCCCOC(=O)C1=CC=CC=C1C(O)=O FFJFEOOXVXIRMN-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- GVSWEQCOFNEDNN-UHFFFAOYSA-N C1(C2C(C(=O)O1)CCCC2)=O.C2(\C=C/C(=O)O2)=O Chemical compound C1(C2C(C(=O)O1)CCCC2)=O.C2(\C=C/C(=O)O2)=O GVSWEQCOFNEDNN-UHFFFAOYSA-N 0.000 description 2
- LERIXMUHBWVOSJ-UHFFFAOYSA-N CC(CO)(CO)CO.C(CCCC(=O)O)CCCC(=O)O Chemical compound CC(CO)(CO)CO.C(CCCC(=O)O)CCCC(=O)O LERIXMUHBWVOSJ-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- HOMUVWAPTHAACL-UHFFFAOYSA-L copper;12-hydroxyoctadecanoate Chemical compound [Cu+2].CCCCCCC(O)CCCCCCCCCCC([O-])=O.CCCCCCC(O)CCCCCCCCCCC([O-])=O HOMUVWAPTHAACL-UHFFFAOYSA-L 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000000593 degrading effect Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/08—Metals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/28—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/39—Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
- C08K5/57—Organo-tin compounds
-
- 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
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1637—Macromolecular compounds
- C09D5/165—Macromolecular compounds containing hydrolysable groups
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/43—Promoting degradability of polymers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/938—Polymer degradation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
- Moulds, Cores, Or Mandrels (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16592281A JPS5867722A (ja) | 1981-10-17 | 1981-10-17 | 加水分解型ポリエステル樹脂の製造法 |
| JP16592381A JPS5867767A (ja) | 1981-10-17 | 1981-10-17 | 防汚塗料 |
| JP16592181A JPS5867761A (ja) | 1981-10-17 | 1981-10-17 | 加水分解型樹脂被膜形成用組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8205838D0 SE8205838D0 (sv) | 1982-10-14 |
| SE8205838L SE8205838L (sv) | 1983-04-18 |
| SE458119B true SE458119B (sv) | 1989-02-27 |
Family
ID=27322592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8205838A SE458119B (sv) | 1981-10-17 | 1982-10-14 | Saett att framstaella ett hydrolyserbart polyesterharts |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4482701A (da) |
| AU (1) | AU559137B2 (da) |
| BR (1) | BR8206063A (da) |
| DE (1) | DE3238357A1 (da) |
| DK (1) | DK163130C (da) |
| FR (1) | FR2514771B1 (da) |
| GB (1) | GB2110707B (da) |
| NL (1) | NL190614C (da) |
| NO (1) | NO823448L (da) |
| PT (1) | PT75688B (da) |
| SE (1) | SE458119B (da) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4585687A (en) * | 1983-05-16 | 1986-04-29 | American Hoechst Corporation | Copolyester primed polyester film |
| US4525419A (en) * | 1983-05-16 | 1985-06-25 | American Hoechst Corporation | Copolyester primed plastic film |
| US4745019A (en) * | 1983-05-16 | 1988-05-17 | American Hoechst Corporation | Graphic film having a copolyester primed polyester film as its substrate |
| ES8800975A1 (es) * | 1985-04-18 | 1987-12-01 | Nippon Paint Co Ltd | Un procedimiento para la preparacion de una composicion recubridora antiincrustante de propiedades pulidoras mejoradas. |
| ES8801936A1 (es) * | 1985-05-17 | 1988-03-01 | Nippon Paint Co Ltd | Un procedimiento para preparar una resina hidrolizable. |
| US4686275A (en) * | 1986-02-25 | 1987-08-11 | Valvoline Oil & Chemicals Ltd. | Saturated linear polyester resin composition suitable for coating a metal for anti-corrosion and/or decorative purposes |
| JPH0625317B2 (ja) * | 1986-08-26 | 1994-04-06 | 日本ペイント株式会社 | 防汚塗料用球形崩壊型ビニル樹脂粒子 |
| JPS6372768A (ja) * | 1986-09-16 | 1988-04-02 | Nippon Paint Co Ltd | 防汚塗料 |
| EP0286243B1 (en) * | 1987-03-12 | 1993-11-03 | Nippon Paint Co., Ltd. | Disintegration type resin particles, its preparation and coating composition containing the same |
| JP2739488B2 (ja) * | 1988-12-29 | 1998-04-15 | 日本ペイント株式会社 | 加水分解型シリコーン樹脂被膜を有する塗装物 |
| DE69408186T2 (de) * | 1993-03-25 | 1998-05-14 | Dainippon Toryo Kk | Antifäulnisfarbe |
| DE4440858A1 (de) | 1994-11-15 | 1996-05-23 | Basf Ag | Biologisch abbaubare Polymere, Verfahren zu deren Herstellung sowie deren Verwendung zur Herstellung bioabbaubarer Formkörper |
| US5637745A (en) * | 1995-01-30 | 1997-06-10 | Elf Atochem North America, Inc. | Organometallic compounds and polymers made therefrom |
| NO327258B1 (no) * | 1999-07-27 | 2009-05-25 | Ishikawajima Harima Heavy Ind | Polyesterharpiks for anvendelse i en grohemmende maling samt grohemmende maling omfattende polyesterharpiksen |
| US7279545B2 (en) * | 2003-12-04 | 2007-10-09 | Kabushiki Kaisha J-Corporation | Production method of biodegradable plastic and apparatus for use in production thereof |
| JP7590404B2 (ja) * | 2019-07-12 | 2024-11-26 | ダウ グローバル テクノロジーズ エルエルシー | ポリウレタンポリマーに使用するための金属ポリオール |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2985624A (en) * | 1956-10-09 | 1961-05-23 | Anaconda Wire & Cable Co | Preparation of zinc polyesters |
| US3053783A (en) * | 1958-09-19 | 1962-09-11 | Standard Oil Co | Water soluble polyesters of benzene polycarboxylic acids |
| US3057826A (en) * | 1959-12-21 | 1962-10-09 | Du Pont | Copolyesters having carboxylate salt groups |
| US3075936A (en) * | 1960-03-30 | 1963-01-29 | Standard Oil Co | Surface coating composition of a resinpolyester mixture |
| US3318763A (en) * | 1961-08-24 | 1967-05-09 | Vanderbilt Co R T | Bacterial and fungal methods |
| BE756074A (fr) * | 1969-09-11 | 1971-03-11 | Hoechst Ag | Matieres a mouler thermoplastiques a base de polyesters |
| US3725327A (en) * | 1970-11-16 | 1973-04-03 | Vanderbilt Co R T | Zinc di(lower alkyl) dithiocarbamates as mold inhibitors for latex paints |
| FR2307013A1 (fr) * | 1975-04-10 | 1976-11-05 | Rhone Poulenc Ind | Preparation de vernis a base de resine polyester |
| DE2656749A1 (de) * | 1975-12-23 | 1977-07-14 | Ciba Geigy Ag | Neue biocide |
| US4128429A (en) * | 1977-01-06 | 1978-12-05 | Sankyo Organic Chemicals Company Limited | Antifouling quaternary halide salts containing a triorganotin ether moiety |
| FR2384010A1 (fr) * | 1977-03-15 | 1978-10-13 | Nal Pour Expl Oceans Centre | Peinture antisalissure |
| US4277392A (en) * | 1979-06-01 | 1981-07-07 | Tenneco Chemicals, Inc. | Thickening agents for unsaturated polyester resin compositions |
| US4282126A (en) * | 1979-08-24 | 1981-08-04 | The United States Of America As Represented By The Secretary Of The Navy | Polyisobutylene rubber antifouling paint |
-
1982
- 1982-09-28 US US06/426,155 patent/US4482701A/en not_active Expired - Lifetime
- 1982-10-13 AU AU89337/82A patent/AU559137B2/en not_active Ceased
- 1982-10-14 SE SE8205838A patent/SE458119B/sv not_active IP Right Cessation
- 1982-10-15 FR FR8217306A patent/FR2514771B1/fr not_active Expired
- 1982-10-15 PT PT75688A patent/PT75688B/pt not_active IP Right Cessation
- 1982-10-15 DE DE19823238357 patent/DE3238357A1/de not_active Ceased
- 1982-10-15 NL NL8203999A patent/NL190614C/xx not_active IP Right Cessation
- 1982-10-15 GB GB08229516A patent/GB2110707B/en not_active Expired
- 1982-10-15 DK DK459082A patent/DK163130C/da not_active IP Right Cessation
- 1982-10-15 NO NO823448A patent/NO823448L/no unknown
- 1982-10-18 BR BR8206063A patent/BR8206063A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4482701A (en) | 1984-11-13 |
| DK163130B (da) | 1992-01-20 |
| DE3238357A1 (de) | 1983-06-23 |
| DK459082A (da) | 1983-04-18 |
| GB2110707B (en) | 1985-08-21 |
| BR8206063A (pt) | 1983-09-13 |
| GB2110707A (en) | 1983-06-22 |
| AU8933782A (en) | 1983-04-28 |
| NL190614B (nl) | 1993-12-16 |
| SE8205838D0 (sv) | 1982-10-14 |
| NO823448L (no) | 1983-04-18 |
| DK163130C (da) | 1992-06-15 |
| FR2514771B1 (fr) | 1986-09-19 |
| NL190614C (nl) | 1994-05-16 |
| FR2514771A1 (fr) | 1983-04-22 |
| PT75688A (en) | 1982-11-01 |
| PT75688B (en) | 1985-01-10 |
| SE8205838L (sv) | 1983-04-18 |
| AU559137B2 (en) | 1987-02-26 |
| NL8203999A (nl) | 1983-05-16 |
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