DE60007108T2 - Kondensationspolymer, enthaltend Esteralkylamidsäureendgruppen - Google Patents
Kondensationspolymer, enthaltend Esteralkylamidsäureendgruppen Download PDFInfo
- Publication number
- DE60007108T2 DE60007108T2 DE60007108T DE60007108T DE60007108T2 DE 60007108 T2 DE60007108 T2 DE 60007108T2 DE 60007108 T DE60007108 T DE 60007108T DE 60007108 T DE60007108 T DE 60007108T DE 60007108 T2 DE60007108 T2 DE 60007108T2
- Authority
- DE
- Germany
- Prior art keywords
- polymer
- cyclo
- aryl
- alkyl radical
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 89
- 238000009833 condensation Methods 0.000 title claims abstract description 9
- 230000005494 condensation Effects 0.000 title claims abstract description 9
- 239000002253 acid Substances 0.000 title description 13
- 125000005907 alkyl ester group Chemical group 0.000 title description 3
- -1 cyclic anhydride Chemical class 0.000 claims abstract description 35
- 239000000843 powder Substances 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 239000003973 paint Substances 0.000 claims abstract description 14
- 150000002148 esters Chemical class 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 7
- 238000000576 coating method Methods 0.000 claims description 36
- 239000011248 coating agent Substances 0.000 claims description 18
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000011230 binding agent Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 5
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 claims description 4
- 229940043276 diisopropanolamine Drugs 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 3
- 239000008199 coating composition Substances 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 abstract description 5
- 150000008064 anhydrides Chemical class 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 229920001187 thermosetting polymer Polymers 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000004048 modification Effects 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 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 5
- 239000004971 Cross linker Substances 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 229940102253 isopropanolamine Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-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
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 2
- 150000002918 oxazolines Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 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 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 0 *N*1C2(CC2)C1 Chemical compound *N*1C2(CC2)C1 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- QNYBOILAKBSWFG-UHFFFAOYSA-N 2-(phenylmethoxymethyl)oxirane Chemical compound C1OC1COCC1=CC=CC=C1 QNYBOILAKBSWFG-UHFFFAOYSA-N 0.000 description 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
- MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 1
- JBBMLBIXFDCCGQ-UHFFFAOYSA-N 2-ethenyl-1,3-oxazolidine Chemical compound C=CC1NCCO1 JBBMLBIXFDCCGQ-UHFFFAOYSA-N 0.000 description 1
- AVJIQBUUPACBPG-UHFFFAOYSA-N 2-ethyl-1,3-oxazolidine Chemical class CCC1NCCO1 AVJIQBUUPACBPG-UHFFFAOYSA-N 0.000 description 1
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 1
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 1
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 1
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 description 1
- QWJWPDHACGGABF-UHFFFAOYSA-N 5,5-dimethylcyclopenta-1,3-diene Chemical compound CC1(C)C=CC=C1 QWJWPDHACGGABF-UHFFFAOYSA-N 0.000 description 1
- ZOXBWJMCXHTKNU-UHFFFAOYSA-N 5-methyl-2-benzofuran-1,3-dione Chemical compound CC1=CC=C2C(=O)OC(=O)C2=C1 ZOXBWJMCXHTKNU-UHFFFAOYSA-N 0.000 description 1
- FKBMTBAXDISZGN-UHFFFAOYSA-N 5-methyl-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1C(C)CCC2C(=O)OC(=O)C12 FKBMTBAXDISZGN-UHFFFAOYSA-N 0.000 description 1
- JDBDDNFATWXGQZ-UHFFFAOYSA-N 5-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1=CC(C)CC2C(=O)OC(=O)C12 JDBDDNFATWXGQZ-UHFFFAOYSA-N 0.000 description 1
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 1
- 241001214176 Capros Species 0.000 description 1
- ONKUXPIBXRRIDU-UHFFFAOYSA-N Diethyl decanedioate Chemical compound CCOC(=O)CCCCCCCCC(=O)OCC ONKUXPIBXRRIDU-UHFFFAOYSA-N 0.000 description 1
- FANBESOFXBDQSH-UHFFFAOYSA-N Ethyladipic acid Chemical compound CCC(C(O)=O)CCCC(O)=O FANBESOFXBDQSH-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PVNIQBQSYATKKL-UHFFFAOYSA-N Glycerol trihexadecanoate Natural products CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 125000002521 alkyl halide group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- HBPTUDIZKSGJNN-UHFFFAOYSA-N benzoic acid;cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1.OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 HBPTUDIZKSGJNN-UHFFFAOYSA-N 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229940072282 cardura Drugs 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000007590 electrostatic spraying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000006115 industrial coating Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- HPZHFGBKCGWNGN-UHFFFAOYSA-N n-benzyl-2-methyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=12C=CNC2=NC(C)=NC=1NCC1=CC=CC=C1 HPZHFGBKCGWNGN-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- VDZVLUMVRXPKNF-UHFFFAOYSA-N octa-1,5,7-trien-3-ol Chemical compound C=CC(O)CC=CC=C VDZVLUMVRXPKNF-UHFFFAOYSA-N 0.000 description 1
- GUKFHMABRUKJNE-UHFFFAOYSA-N octa-2,5,7-trien-1-ol Chemical compound OCC=CCC=CC=C GUKFHMABRUKJNE-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000010915 one-step procedure Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99200919 | 1999-03-24 | ||
| EP99200919 | 1999-03-24 | ||
| PCT/NL2000/000179 WO2000056804A1 (en) | 1999-03-24 | 2000-03-17 | Condensation polymer containing esteralkylamide-acid groups |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60007108D1 DE60007108D1 (de) | 2004-01-22 |
| DE60007108T2 true DE60007108T2 (de) | 2004-09-16 |
Family
ID=8240023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60007108T Expired - Lifetime DE60007108T2 (de) | 1999-03-24 | 2000-03-17 | Kondensationspolymer, enthaltend Esteralkylamidsäureendgruppen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6645636B2 (enExample) |
| EP (1) | EP1171509B1 (enExample) |
| JP (1) | JP2002540238A (enExample) |
| CN (1) | CN1247662C (enExample) |
| AT (1) | ATE256160T1 (enExample) |
| AU (1) | AU3464800A (enExample) |
| DE (1) | DE60007108T2 (enExample) |
| MY (1) | MY122600A (enExample) |
| TW (1) | TW499449B (enExample) |
| WO (1) | WO2000056804A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6905605B2 (en) | 2000-04-07 | 2005-06-14 | Shell Oil Company | Method for inhibiting the plugging of conduits by gas hydrates |
| EP1149854A1 (en) * | 2000-04-25 | 2001-10-31 | Dsm N.V. | Toner composition |
| NL1016845C2 (nl) * | 2000-12-11 | 2002-06-28 | Topchim N V | Papierbekledingssamenstelling. |
| CA2450162A1 (en) | 2001-06-14 | 2002-12-27 | Shell Internationale Research Maatschappij B.V. | Method for solubilising asphaltenes in a hydrocarbon mixture |
| EP1306401A1 (en) * | 2001-10-29 | 2003-05-02 | Dsm N.V. | Oil soluble hyperbranched polyesteramides and method for making the same |
| JP3986291B2 (ja) * | 2001-10-29 | 2007-10-03 | 株式会社リコー | 粉粒体の造粒成形用バインダ及び造粒成形物 |
| US20060229400A1 (en) * | 2002-05-31 | 2006-10-12 | Tim Fletcher | Powder coating matting agent comprising ester amide condensation product |
| EP1382643A1 (en) * | 2002-06-07 | 2004-01-21 | DSM IP Assets B.V. | Polyesteramide barrier film layer and its use |
| US7696393B2 (en) | 2002-09-03 | 2010-04-13 | Shell Oil Company | Method and compositions for inhibiting formation of hydrocarbon hydrates |
| EP1424362A1 (en) * | 2002-11-27 | 2004-06-02 | DSM IP Assets B.V. | Process for preparing a composition |
| DE60309285T2 (de) * | 2003-04-25 | 2007-05-24 | Ricoh Co., Ltd. | Bindemittel zum granulierenden Umformen von pulverförmigen Teilchen und granulierte Formteile |
| US20050288450A1 (en) * | 2003-05-23 | 2005-12-29 | Tim Fletcher | Coating matting agent comprising amide condensation product |
| DE102004039102A1 (de) * | 2004-08-11 | 2006-02-23 | Basf Ag | Verfahren zur Herstellung von hochverzweigten Polyesteramiden |
| WO2006056578A1 (en) | 2004-11-24 | 2006-06-01 | Shell Internationale Research Maatschappij B.V. | Method for improving the flowability of a mixture that contains wax and other hydrocarbons |
| EP1669396A1 (en) * | 2004-12-10 | 2006-06-14 | Rockwool International A/S | Aqueous binder for mineral fibers |
| CN101163463A (zh) | 2005-02-21 | 2008-04-16 | 巴斯福股份公司 | 包含至少一种含氮原子的超支化聚合物的活性物质组合物 |
| WO2007144189A2 (en) * | 2006-06-16 | 2007-12-21 | Dsm Ip Assets B.V. | Compositions based on hyperbranched condensation polymers and novel hyperbranched condensation polymers |
| US20100130695A1 (en) * | 2006-07-11 | 2010-05-27 | Dsm Ip Assets B.V. | Composition with a polymer and an oxidation-catalyst |
| EP1878762A1 (en) * | 2006-07-11 | 2008-01-16 | DSMIP Assets B.V. | Oxidisable polymer |
| WO2010108985A1 (en) | 2009-03-25 | 2010-09-30 | Dsm Ip Assets B.V. | Improved anti-biofouling coating |
| SG10201605780QA (en) | 2009-03-19 | 2016-09-29 | Emd Millipore Corp | Removal of microorganisms from fluid samples using nanofiber filtration media |
| WO2011007003A1 (en) | 2009-07-16 | 2011-01-20 | Dsm Ip Assets B.V. | Resins and coating compositions |
| EP2504408A2 (en) | 2009-11-25 | 2012-10-03 | DSM IP Assets B.V. | Polyester amide foamers |
| EP2516513A1 (en) | 2009-12-21 | 2012-10-31 | DSM IP Assets B.V. | Polymer, process and composition |
| WO2011141266A1 (de) | 2010-04-15 | 2011-11-17 | Basf Se | Verfahren zur herstellung von flammgeschützten polyurethan-schaumstoffen |
| PH12012502392A1 (en) | 2010-06-03 | 2013-02-11 | Dsm Ip Assets Bv | Membrane suitable for blood filtration |
| JP5549555B2 (ja) * | 2010-11-16 | 2014-07-16 | Ｊｎｃ株式会社 | 硬化性組成物 |
| SG10201605328WA (en) | 2011-04-01 | 2016-08-30 | Emd Millipore Corp | Nanofiber containing composite structures |
| CN103857719B (zh) | 2011-08-05 | 2016-08-17 | 巴斯夫欧洲公司 | 基于超支化聚合物的缔合性增稠剂 |
| NO346017B1 (no) | 2011-12-20 | 2021-12-27 | Shell Int Research | Fremgangmåte for å inhibere plugging av rør av gasshydrater |
| US9528063B2 (en) | 2011-12-20 | 2016-12-27 | Shell Oil Company | Method for inhibiting the plugging of conduits by gas hydrates |
| CN104011111B (zh) | 2011-12-20 | 2016-06-01 | 帝斯曼知识产权资产管理有限公司 | 超支化聚合物 |
| WO2013092797A1 (en) | 2011-12-20 | 2013-06-27 | Dsm Ip Assets B.V. | Hyperbranched polymers |
| CN104011112A (zh) | 2011-12-20 | 2014-08-27 | 帝斯曼知识产权资产管理有限公司 | 超支化聚合物 |
| WO2013092794A1 (en) | 2011-12-20 | 2013-06-27 | Dsm Ip Assets B.V. | Hyperbranched polymers |
| CN104011187B (zh) | 2011-12-20 | 2016-12-14 | 国际壳牌研究有限公司 | 抑制气体水合物堵塞管道的方法 |
| MY171400A (en) | 2011-12-20 | 2019-10-11 | Shell Int Research | Method for inhibiting the plugging of conduits by gas hydrates |
| US9921205B2 (en) | 2012-11-13 | 2018-03-20 | Chevron U.S.A. Inc. | Method for determining the effectiveness of asphaltene dispersant additives for inhibiting or preventing asphaltene precipitation in a hydrocarbon-containing material subjected to elevated temperature and presssure conditions |
| CN105308097B (zh) | 2013-06-20 | 2019-02-12 | 帝斯曼知识产权资产管理有限公司 | 超支化聚合物 |
| CN103641737B (zh) * | 2013-11-29 | 2016-04-20 | 六安市捷通达化工有限责任公司 | 一种羧酸改性的羟烷基酰胺固化剂的制备方法 |
| KR20210115050A (ko) | 2014-06-26 | 2021-09-24 | 이엠디 밀리포어 코포레이션 | 개선된 먼지 포집 능력을 갖는 필터 구조 |
| KR102206963B1 (ko) | 2015-04-17 | 2021-01-25 | 이엠디 밀리포어 코포레이션 | 접선방향 유동 여과 모드에서 작동되는 나노섬유 한외여과막을 사용하여 샘플에서 목적하는 생물학적 물질을 정제하는 방법 |
| US12186713B2 (en) | 2017-07-21 | 2025-01-07 | Merck Millipore Ltd. | Non-woven fiber membranes |
| US10907473B2 (en) | 2017-11-14 | 2021-02-02 | Chevron U.S.A., Inc. | Low volume in-line filtration methods for analyzing hydrocarbon-containing fluid to evaluate asphaltene content and behavior during production operations |
| EP3743459B1 (en) * | 2018-01-26 | 2024-06-12 | Battelle Memorial Institute | Powder coating resins from c12-c23 diesters |
| JP2021511433A (ja) * | 2018-01-26 | 2021-05-06 | バテル・メモリアル・インスティテュートＢａｔｔｅｌｌｅ Ｍｅｍｏｒｉａｌ Ｉｎｓｔｉｔｕｔｅ | Ｃ１２〜ｃ２３二酸からの粉体コーティング樹脂 |
| EP4090714B1 (en) | 2020-01-13 | 2023-10-04 | Covestro (Netherlands) B.V. | Non-porous microparticles |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3709858A (en) * | 1971-06-10 | 1973-01-09 | Eastman Kodak Co | Polyesteramide coating compositions |
| CA1002232A (en) * | 1972-03-24 | 1976-12-21 | Eastman Kodak Company | Water-soluble alkyd resins and a process for their preparation |
| DE3621039A1 (de) * | 1986-06-24 | 1988-01-07 | Bayer Ag | Verfahren zur herstellung von hydroxylgruppen aufweisenden oligoestern und deren verwendung |
| JP2617600B2 (ja) * | 1990-03-02 | 1997-06-04 | ポリプラスチックス株式会社 | 芳香族ポリエステルアミド共重合体およびその製造法 |
| JP2575918B2 (ja) * | 1990-03-20 | 1997-01-29 | ポリプラスチックス株式会社 | ハロゲン含有芳香族ポリエステルアミドおよびその製造法 |
| JP2670380B2 (ja) * | 1990-05-15 | 1997-10-29 | ポリプラスチックス株式会社 | 芳香族ポリエステルアミドの製造法 |
| NL1007186C2 (nl) * | 1997-10-01 | 1999-04-07 | Dsm Nv | ß-hydroxyalkylamide groepen bevattend condensatiepolymeer. |
-
2000
- 2000-03-07 TW TW089104101A patent/TW499449B/zh active
- 2000-03-17 EP EP00913166A patent/EP1171509B1/en not_active Revoked
- 2000-03-17 JP JP2000606664A patent/JP2002540238A/ja active Pending
- 2000-03-17 CN CNB00807836XA patent/CN1247662C/zh not_active Expired - Fee Related
- 2000-03-17 AT AT00913166T patent/ATE256160T1/de not_active IP Right Cessation
- 2000-03-17 AU AU34648/00A patent/AU3464800A/en not_active Abandoned
- 2000-03-17 WO PCT/NL2000/000179 patent/WO2000056804A1/en not_active Ceased
- 2000-03-17 DE DE60007108T patent/DE60007108T2/de not_active Expired - Lifetime
- 2000-03-21 MY MYPI20001115A patent/MY122600A/en unknown
-
2001
- 2001-09-24 US US09/961,182 patent/US6645636B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6645636B2 (en) | 2003-11-11 |
| ATE256160T1 (de) | 2003-12-15 |
| EP1171509B1 (en) | 2003-12-10 |
| MY122600A (en) | 2006-04-29 |
| CN1247662C (zh) | 2006-03-29 |
| DE60007108D1 (de) | 2004-01-22 |
| US20020035236A1 (en) | 2002-03-21 |
| AU3464800A (en) | 2000-10-09 |
| EP1171509A1 (en) | 2002-01-16 |
| JP2002540238A (ja) | 2002-11-26 |
| TW499449B (en) | 2002-08-21 |
| WO2000056804A1 (en) | 2000-09-28 |
| CN1351624A (zh) | 2002-05-29 |
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| 8363 | Opposition against the patent |