JP5305918B2 - グリセロールレブリネートケタール類とその使用 - Google Patents
グリセロールレブリネートケタール類とその使用 Download PDFInfo
- Publication number
- JP5305918B2 JP5305918B2 JP2008542439A JP2008542439A JP5305918B2 JP 5305918 B2 JP5305918 B2 JP 5305918B2 JP 2008542439 A JP2008542439 A JP 2008542439A JP 2008542439 A JP2008542439 A JP 2008542439A JP 5305918 B2 JP5305918 B2 JP 5305918B2
- Authority
- JP
- Japan
- Prior art keywords
- linear
- branched
- polymer
- formula
- compound
- 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 - Fee Related
Links
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 262
- 229940058352 levulinate Drugs 0.000 title description 36
- JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical compound CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 title description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 263
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims abstract description 58
- 239000004814 polyurethane Substances 0.000 claims abstract description 39
- 229920002635 polyurethane Polymers 0.000 claims abstract description 39
- 229940040102 levulinic acid Drugs 0.000 claims abstract description 30
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims description 203
- 239000000203 mixture Substances 0.000 claims description 133
- -1 amine salt Chemical class 0.000 claims description 85
- 238000006243 chemical reaction Methods 0.000 claims description 69
- 239000001257 hydrogen Substances 0.000 claims description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 239000003054 catalyst Substances 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 49
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
- 239000011541 reaction mixture Substances 0.000 claims description 32
- 238000005809 transesterification reaction Methods 0.000 claims description 32
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 25
- 229920001577 copolymer Polymers 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 239000004014 plasticizer Substances 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 22
- 150000005846 sugar alcohols Polymers 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 16
- 239000004800 polyvinyl chloride Substances 0.000 claims description 16
- 239000004094 surface-active agent Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000009472 formulation Methods 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 13
- 150000004676 glycans Chemical class 0.000 claims description 13
- 229920001282 polysaccharide Polymers 0.000 claims description 13
- 239000005017 polysaccharide Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000003377 acid catalyst Substances 0.000 claims description 10
- 150000005690 diesters Chemical class 0.000 claims description 10
- 239000012634 fragment Substances 0.000 claims description 10
- 239000003513 alkali Substances 0.000 claims description 9
- 229920001519 homopolymer Polymers 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 7
- 150000004730 levulinic acid derivatives Chemical class 0.000 claims description 7
- 238000006068 polycondensation reaction Methods 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 229920005601 base polymer Polymers 0.000 claims description 6
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical group OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003973 paint Substances 0.000 claims description 6
- 229920000739 poly(3-hydroxycarboxylic acid) polymer Polymers 0.000 claims description 6
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 5
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 4
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 claims description 4
- 229920000070 poly-3-hydroxybutyrate Polymers 0.000 claims description 4
- 150000005691 triesters Chemical class 0.000 claims description 4
- 239000004711 α-olefin Substances 0.000 claims description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- BGLUXFNVVSVEET-UHFFFAOYSA-N beta-angelica lactone Chemical compound CC1OC(=O)C=C1 BGLUXFNVVSVEET-UHFFFAOYSA-N 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 238000004851 dishwashing Methods 0.000 claims description 3
- 239000004519 grease Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000004816 latex Substances 0.000 claims description 2
- 229920000126 latex Polymers 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 238000004140 cleaning Methods 0.000 claims 2
- 150000002118 epoxides Chemical class 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 239000013527 degreasing agent Substances 0.000 claims 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 30
- 238000002360 preparation method Methods 0.000 abstract description 12
- 235000011187 glycerol Nutrition 0.000 description 80
- 239000000047 product Substances 0.000 description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- 238000004821 distillation Methods 0.000 description 55
- 230000015572 biosynthetic process Effects 0.000 description 47
- 150000002924 oxiranes Chemical group 0.000 description 31
- 230000002829 reductive effect Effects 0.000 description 31
- 238000003786 synthesis reaction Methods 0.000 description 30
- 239000007788 liquid Substances 0.000 description 29
- 238000003756 stirring Methods 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 20
- 235000014113 dietary fatty acids Nutrition 0.000 description 20
- 239000000194 fatty acid Substances 0.000 description 20
- 229930195729 fatty acid Natural products 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 238000006116 polymerization reaction Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 239000007795 chemical reaction product Substances 0.000 description 14
- 239000000178 monomer Substances 0.000 description 14
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 150000003626 triacylglycerols Chemical class 0.000 description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 229920001169 thermoplastic Polymers 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 9
- 229920000747 poly(lactic acid) Polymers 0.000 description 9
- 229920000331 Polyhydroxybutyrate Polymers 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 239000006260 foam Substances 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 0 *OC(CCC1(OC(*O)CO1)I)=O Chemical compound *OC(CCC1(OC(*O)CO1)I)=O 0.000 description 7
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- 239000006184 cosolvent Substances 0.000 description 7
- 239000012975 dibutyltin dilaurate Substances 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UAGJVSRUFNSIHR-UHFFFAOYSA-N Methyl levulinate Chemical compound COC(=O)CCC(C)=O UAGJVSRUFNSIHR-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 6
- 235000019796 monopotassium phosphate Nutrition 0.000 description 6
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 150000002314 glycerols Chemical class 0.000 description 5
- 150000001261 hydroxy acids Chemical class 0.000 description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- 229920000903 polyhydroxyalkanoate Polymers 0.000 description 5
- 238000007142 ring opening reaction Methods 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- 239000003549 soybean oil Substances 0.000 description 5
- 235000012424 soybean oil Nutrition 0.000 description 5
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 5
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 4
- 150000007522 mineralic acids Chemical class 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 4
- QAPDVRQDEPWTMJ-UHFFFAOYSA-N 2,3-dihydroxypropyl 4-oxopentanoate Chemical compound CC(=O)CCC(=O)OCC(O)CO QAPDVRQDEPWTMJ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 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 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 3
- 229920005830 Polyurethane Foam Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910001424 calcium ion Inorganic materials 0.000 description 3
- 239000000828 canola oil Substances 0.000 description 3
- 235000019519 canola oil Nutrition 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
- 230000005494 condensation Effects 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 239000012973 diazabicyclooctane Substances 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 3
- 239000011552 falling film Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 3
- 150000002402 hexoses Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- 238000010550 living polymerization reaction Methods 0.000 description 3
- 229910001425 magnesium ion Inorganic materials 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 235000019645 odor Nutrition 0.000 description 3
- 239000012766 organic filler Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920002959 polymer blend Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 239000011496 polyurethane foam Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000004634 thermosetting polymer Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 239000000811 xylitol Substances 0.000 description 3
- 235000010447 xylitol Nutrition 0.000 description 3
- 229960002675 xylitol Drugs 0.000 description 3
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- VPVXHAANQNHFSF-UHFFFAOYSA-N 1,4-dioxan-2-one Chemical class O=C1COCCO1 VPVXHAANQNHFSF-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
- BOZRCGLDOHDZBP-UHFFFAOYSA-N 2-ethylhexanoic acid;tin Chemical compound [Sn].CCCCC(CC)C(O)=O BOZRCGLDOHDZBP-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- ISBWNEKJSSLXOD-UHFFFAOYSA-N Butyl levulinate Chemical compound CCCCOC(=O)CCC(C)=O ISBWNEKJSSLXOD-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004386 Erythritol Substances 0.000 description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000003225 biodiesel Substances 0.000 description 2
- 238000006664 bond formation reaction Methods 0.000 description 2
- 229920005605 branched copolymer Polymers 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 229940005460 butyl levulinate Drugs 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 235000019414 erythritol Nutrition 0.000 description 2
- 229940009714 erythritol Drugs 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229960002479 isosorbide Drugs 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 229920005684 linear copolymer Polymers 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000012783 reinforcing fiber Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 229940058349 sodium levulinate Drugs 0.000 description 2
- JYCDILBEUUCCQD-UHFFFAOYSA-N sodium;2-methylpropan-1-olate Chemical compound [Na+].CC(C)C[O-] JYCDILBEUUCCQD-UHFFFAOYSA-N 0.000 description 2
- ZJVAANZDGCUXLB-UHFFFAOYSA-N sodium;3-methylbutan-1-olate Chemical compound [Na+].CC(C)CC[O-] ZJVAANZDGCUXLB-UHFFFAOYSA-N 0.000 description 2
- RDKYCKDVIYTSAJ-UHFFFAOYSA-M sodium;4-oxopentanoate Chemical compound [Na+].CC(=O)CCC([O-])=O RDKYCKDVIYTSAJ-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 150000000185 1,3-diols Chemical class 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 description 1
- SJDLIJNQXLJBBE-UHFFFAOYSA-N 1,4-dioxepan-2-one Chemical class O=C1COCCCO1 SJDLIJNQXLJBBE-UHFFFAOYSA-N 0.000 description 1
- DFPJRUKWEPYFJT-UHFFFAOYSA-N 1,5-diisocyanatopentane Chemical compound O=C=NCCCCCN=C=O DFPJRUKWEPYFJT-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
- SQRDEVDPDGSBGC-UHFFFAOYSA-N 4,7,7-trimethyl-3-oxabicyclo[2.2.1]heptan-2-one Chemical compound C1CC2(C)OC(=O)C1C2(C)C SQRDEVDPDGSBGC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-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
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- JVWLUVNSQYXYBE-UHFFFAOYSA-N Ribitol Natural products OCC(C)C(O)C(O)CO JVWLUVNSQYXYBE-UHFFFAOYSA-N 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- ILWVFNNXAHVFCW-UHFFFAOYSA-N [3-hydroxy-2-(4-oxopentanoyloxy)propyl] 4-oxopentanoate Chemical compound CC(=O)CCC(=O)OCC(CO)OC(=O)CCC(C)=O ILWVFNNXAHVFCW-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- QOTQFLOTGBBMEX-UHFFFAOYSA-N alpha-angelica lactone Chemical compound CC1=CCC(=O)O1 QOTQFLOTGBBMEX-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- PEHLCCGXTLWMRW-UHFFFAOYSA-N bis-lactone Chemical compound C1CC2OC(=O)C3C1OC(=O)C32 PEHLCCGXTLWMRW-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- GZSQUYTXLHVHCI-UHFFFAOYSA-N decanoic acid heptane Chemical compound CCCCCCC.CCCCCCCCCC(O)=O GZSQUYTXLHVHCI-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000005237 degreasing agent Methods 0.000 description 1
- 238000012691 depolymerization reaction Methods 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- UAMZXLIURMNTHD-UHFFFAOYSA-N dialuminum;magnesium;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Mg+2].[Al+3].[Al+3] UAMZXLIURMNTHD-UHFFFAOYSA-N 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 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
- 238000002474 experimental method Methods 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 1
- 235000001785 ferulic acid Nutrition 0.000 description 1
- 229940114124 ferulic acid Drugs 0.000 description 1
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical class CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 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 1
- 125000005908 glyceryl ester group Chemical group 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 125000005524 levulinyl group Chemical group 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 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
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- NQKYFDXCRYGCEQ-UHFFFAOYSA-N methyl 8-(3-octyloxiren-2-yl)octanoate Chemical compound CCCCCCCCC1=C(CCCCCCCC(=O)OC)O1 NQKYFDXCRYGCEQ-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 125000001805 pentosyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229940065514 poly(lactide) Drugs 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 125000005471 saturated fatty acid group Chemical group 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium 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
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000005314 unsaturated fatty acid group Chemical group 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4283—Hydroxycarboxylic acid or ester
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/18—Bridged systems
-
- 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
- Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
- Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
- Y10T428/139—Open-ended, self-supporting conduit, cylinder, or tube-type article
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73898805P | 2005-11-22 | 2005-11-22 | |
| US60/738,988 | 2005-11-22 | ||
| PCT/US2006/045200 WO2007062118A2 (en) | 2005-11-22 | 2006-11-22 | Glycerol levulinate ketals and their use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009519901A JP2009519901A (ja) | 2009-05-21 |
| JP2009519901A5 JP2009519901A5 (US20080242721A1-20081002-C00060.png) | 2012-11-22 |
| JP5305918B2 true JP5305918B2 (ja) | 2013-10-02 |
Family
ID=38067898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008542439A Expired - Fee Related JP5305918B2 (ja) | 2005-11-22 | 2006-11-22 | グリセロールレブリネートケタール類とその使用 |
Country Status (18)
Families Citing this family (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1954140B1 (en) | 2005-11-22 | 2013-05-29 | Segetis, Inc. | Glycerol levulinate ketals and their use |
| KR101337124B1 (ko) * | 2005-11-22 | 2013-12-05 | 세게티스, 인코포레이티드. | 에폭시화 지방산 에스테르를 갖는 레불린산 유도체의부가물 및 그의 용도 |
| BRPI0816422A2 (pt) | 2007-09-04 | 2017-05-16 | Segetis Inc | compostos de cetal a partir de polióis e oxocarboxilatos. |
| BRPI0818370A2 (pt) * | 2007-10-09 | 2017-05-16 | Segetis Inc | métodos de fabricar cetais e acetais |
| CN101883773B (zh) * | 2007-10-09 | 2014-05-21 | 希凯迪斯股份有限公司 | 聚缩酮，合成和应用 |
| US8653223B2 (en) * | 2008-04-16 | 2014-02-18 | Segetis, Inc. | Transketalized compositions, synthesis, and applications |
| US8575367B2 (en) | 2008-09-25 | 2013-11-05 | Segetis, Inc. | Ketal ester derivatives |
| JP5667986B2 (ja) * | 2008-12-22 | 2015-02-12 | シーマ・アジャイ・ランカ | アスファルトと鉱物の組成物 |
| BRPI0922127A2 (pt) * | 2008-12-23 | 2016-09-06 | Segetis Inc | composto, formulação, artigo, polímero e método para fabricar poliamida. |
| MX2011012523A (es) * | 2009-05-29 | 2012-02-28 | Xlterra Inc | Esteres cetalicos de anhidropentitoles y usos de los mismos. |
| BRPI1012056A2 (pt) * | 2009-05-29 | 2016-05-17 | Segetis Inc | solução solvente, composição de limpeza e métodos |
| KR101808867B1 (ko) | 2009-06-22 | 2018-01-18 | 세게티스, 인코포레이티드. | 케탈 화합물 및 이의 용도 |
| US8598109B2 (en) * | 2009-09-11 | 2013-12-03 | Method Products, Inc. | Fabric softener |
| CA2796883A1 (en) * | 2010-05-10 | 2011-11-17 | Segetis, Inc. | Personal care formulations containing alkyl ketal esters and methods of manufacture |
| MX336783B (es) | 2010-08-03 | 2016-02-02 | Segetis Inc | Metodos para la fabricacion de acetales y cetales, y los acetales y cetales producidos mediante dicho metodo. |
| BR112013002991A2 (pt) | 2010-08-12 | 2016-08-16 | Segetis Inc | composições de revestimento de látex incluindo carboxiéster cetal coalescentes, métodos de fabricação e usos dos mesmos |
| KR20130102532A (ko) * | 2010-08-12 | 2013-09-17 | 세게티스, 인코포레이티드. | 카르복시 에스테르 케탈 제거 조성물, 이의 제조 방법 및 용도 |
| JP2013538060A (ja) | 2010-08-30 | 2013-10-10 | アルゼダ コーポレーション | レブリン酸、レブリン酸エステル、バレロラクトン、およびこれらの誘導体の産生のための発酵経路 |
| IL207945A0 (en) | 2010-09-02 | 2010-12-30 | Robert Jansen | Method for the production of carbohydrates |
| EP2613760A2 (en) | 2010-09-07 | 2013-07-17 | Segetis, Inc. | Compositions for dyeing keratin fibers |
| CN103097604A (zh) * | 2010-09-13 | 2013-05-08 | 赛格提斯有限公司 | 织物软化剂组合物及其制造方法 |
| FR2965814B1 (fr) | 2010-10-08 | 2012-11-16 | Roquette Freres | Plastification de polyesters aliphatiques par des esters alkyliques de dianhydrohexitols |
| US8728625B2 (en) * | 2010-10-18 | 2014-05-20 | Segetis, Inc. | Water reducible coating compositions including carboxy ester ketals, methods of manufacture, and uses thereof |
| US8383710B2 (en) | 2010-10-21 | 2013-02-26 | Eastman Chemical Company | Waterborne coating compositions containing low-VOC coalescents |
| US9034964B2 (en) | 2010-10-21 | 2015-05-19 | Eastman Chemical Company | Waterborne coating compositions containing low-VOC coalescents that are hydroxypivalyl hydroxypivalate esters |
| CN103209951B (zh) | 2010-11-11 | 2016-04-20 | 赛格提斯公司 | 酮基羧酸、酮基羧酸酯、其制造和使用方法 |
| US9187598B2 (en) * | 2010-11-11 | 2015-11-17 | Segetis, Inc. | Polyhydroxy ketal ester adducts, methods of manufacture and uses thereof |
| BR112013011149A2 (pt) * | 2010-11-11 | 2016-08-02 | Segetis Inc | adutos poliacetal, métodos de fabricação e seus usos. |
| US9126890B2 (en) * | 2011-10-20 | 2015-09-08 | International Flavors & Fragrances Inc. | Low volatile reactive malodor counteractives and methods of use thereof |
| US9617608B2 (en) | 2011-10-10 | 2017-04-11 | Virdia, Inc. | Sugar compositions |
| US20130087073A1 (en) | 2011-10-11 | 2013-04-11 | Segetis, Inc. | Stabilized levulinic ester ketals |
| US9458414B2 (en) | 2012-09-21 | 2016-10-04 | Gfbiochemicals Limited | Cleaning, surfactant, and personal care compositions |
| KR20150084897A (ko) * | 2012-11-12 | 2015-07-22 | 세게티스, 인코포레이티드. | 가교성 폴리케탈 에스터, 그의 제조 방법 및 용도 |
| US9156809B2 (en) | 2012-11-29 | 2015-10-13 | Segetis, Inc. | Carboxy ester ketals, methods of manufacture, and uses thereof |
| WO2014150782A1 (en) * | 2013-03-15 | 2014-09-25 | Segetis, Inc. | Ketal adducts, methods of manufacture, and uses thereof |
| US20160044914A1 (en) * | 2013-03-15 | 2016-02-18 | Segetis, Inc. | Biocide compositions, methods of manufacture, and methods of use |
| US10249721B2 (en) | 2013-04-04 | 2019-04-02 | Infineon Technologies Austria Ag | Semiconductor device including a gate trench and a source trench |
| BR102013010477A2 (pt) | 2013-04-29 | 2015-11-17 | Brasil Bio Fuels S A | ésteres de acetais produzidos a partir de glicerina purificada para o uso e aplicações como emolientes, lubrificantes, plastificantes, solventes, coalescentes, umectantes, monomeros de polimerização, aditivos para biocombustíveis |
| US9666663B2 (en) | 2013-08-09 | 2017-05-30 | Infineon Technologies Ag | Semiconductor device with cell trench structures and contacts and method of manufacturing a semiconductor device |
| US9076838B2 (en) | 2013-09-13 | 2015-07-07 | Infineon Technologies Ag | Insulated gate bipolar transistor with mesa sections between cell trench structures and method of manufacturing |
| ITPN20130066A1 (it) * | 2013-11-11 | 2015-05-12 | Fluos S A S Di Giuseppe Chiaradia & C | Plastificanti per polimeri |
| US9105679B2 (en) | 2013-11-27 | 2015-08-11 | Infineon Technologies Ag | Semiconductor device and insulated gate bipolar transistor with barrier regions |
| US9385228B2 (en) | 2013-11-27 | 2016-07-05 | Infineon Technologies Ag | Semiconductor device with cell trench structures and contacts and method of manufacturing a semiconductor device |
| EP3476889B1 (en) | 2014-01-30 | 2021-03-03 | GFBiochemicals IP Assets B.V. | Plasticizer blends of ketal compounds |
| US9553179B2 (en) | 2014-01-31 | 2017-01-24 | Infineon Technologies Ag | Semiconductor device and insulated gate bipolar transistor with barrier structure |
| US9951171B2 (en) | 2014-08-20 | 2018-04-24 | Resinate Materials Group, Inc. | Polyester polyols from recycled polymers and waste streams |
| US9850400B2 (en) | 2014-08-20 | 2017-12-26 | Resinate Materials Group, Inc. | Digestion of keratin |
| JP2017535662A (ja) | 2014-08-20 | 2017-11-30 | レジネート マテリアルズ グループ、インコーポレイテッド | 再生ポリマー及び廃棄物からのポリエステルポリオール |
| US9580546B2 (en) | 2014-10-29 | 2017-02-28 | Resinate Materials Group, Inc. | Polymeric plasticizer compositions |
| CN107075094A (zh) | 2014-10-29 | 2017-08-18 | 树脂酸盐材料集团有限公司 | 来自羟基官能的缩酮酸、酯或酰胺的高再循环含量的聚酯型多元醇 |
| US9890243B2 (en) | 2014-10-29 | 2018-02-13 | Resinate Materials Group, Inc. | Polymeric plasticizer compositions |
| US10214505B2 (en) * | 2014-11-20 | 2019-02-26 | Gfbiochemicals Limited | Ketal ester compounds and uses thereof |
| EP3242871B1 (en) | 2015-01-07 | 2019-11-06 | Virdia, Inc. | Methods for extracting and converting hemicellulose sugars |
| US10226544B2 (en) | 2015-06-05 | 2019-03-12 | International Flavors & Fragrances Inc. | Malodor counteracting compositions |
| CA2994540A1 (en) | 2015-08-03 | 2017-02-09 | Ecolab Usa Inc. | Compositions and methods for delayed crosslinking in hydraulic fracturing fluids |
| CN105218511B (zh) * | 2015-10-12 | 2017-07-14 | 太原理工大学 | 一种脂肪醛缩甘油磺基琥珀酸单酯盐及其制备工艺 |
| US10040894B2 (en) | 2016-03-28 | 2018-08-07 | International Business Machines Corporation | Polymeric materials formed from polyhydroxyalkanoate materials |
| CA3030763A1 (en) | 2016-07-15 | 2018-01-18 | Ecolab Usa Inc. | Compositions and methods for delayed crosslinking in hydraulic fracturing fluids |
| WO2018011741A1 (en) * | 2016-07-15 | 2018-01-18 | Sabic Global Technologies B.V. | Synthesis of ketals and levulinates |
| US10072120B2 (en) | 2016-12-02 | 2018-09-11 | International Business Machines Corporation | Functionalized polyhydroxyalkanoate materials formed from an unsaturated polyhydroxyalkanoate material |
| US10081706B2 (en) | 2017-01-03 | 2018-09-25 | International Business Machines Corporation | Side-chain-functionalized polyhydroxyalkanoate materials |
| WO2019100058A1 (en) | 2017-11-20 | 2019-05-23 | Resinate Materials Group, Inc. | Polyol compositions from thermoplastic polyesters and their use in hot-melt adhesives and binders |
| DE102018217537A1 (de) * | 2018-10-12 | 2020-04-16 | BSH Hausgeräte GmbH | Haushaltsgerät, Verfahren zum Herstellen eines Haushaltsgeräts und Verfahren zum Demontieren eines Haushaltsgeräts |
| US11566145B2 (en) | 2019-03-14 | 2023-01-31 | Covestro Llc | Polyurethane coating compositions and their use as gel coats |
| US10544158B1 (en) | 2019-03-14 | 2020-01-28 | Covestro Llc | Process for producing polycyclic polyether polyols |
| CN110078701A (zh) * | 2019-03-29 | 2019-08-02 | 郑州大学 | 一种农林废弃物制备生物质基缩酮酯的方法 |
| CN114072675A (zh) | 2019-04-30 | 2022-02-18 | 康奈尔大学 | 具有包括两性离子部分的带正电组分的主链的聚合物纤维 |
| CN113929654B (zh) * | 2021-10-26 | 2022-09-02 | 郑州大学 | 一种乙酰丙酸甘油缩酮甲酯的连续合成方法及应用 |
| WO2023084103A1 (en) * | 2021-11-15 | 2023-05-19 | Arxada Ag | Preservative composition |
Family Cites Families (130)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1934309A (en) * | 1933-11-07 | Cyclic acetals and process of | ||
| US2556135A (en) * | 1951-06-05 | Preparation of ketal esters | ||
| US2260261A (en) * | 1941-10-21 | Cyclic ketals and process for | ||
| US2008720A (en) * | 1932-05-03 | 1935-07-23 | Du Pont | Levulinic acid ester |
| US2004115A (en) * | 1932-05-07 | 1935-06-11 | Du Pont | Levulinic acid esters and their preparation |
| US2654723A (en) * | 1950-11-01 | 1953-10-06 | Gen Tire & Rubber Co | Polyvinyl composition and method of making same |
| FR1166940A (fr) * | 1956-03-27 | 1958-11-17 | Dehydag | Plastifiants et gélifiants pour hauts polymères |
| NL295816A (US20080242721A1-20081002-C00060.png) * | 1962-07-27 | |||
| US3330840A (en) | 1964-06-08 | 1967-07-11 | Everett H Pryde | Derivatives of methyl 9, 9-dimethoxynonanoate |
| FR1445013A (fr) | 1964-07-09 | 1966-07-08 | Thomae Gmbh Dr K | Procédé pour fabriquer des nouveaux acides dioxolano-2-carboxyliques |
| US3714202A (en) | 1969-07-15 | 1973-01-30 | Atlantic Richfield Co | Vinyl glycerol acetals |
| US3658789A (en) * | 1970-01-19 | 1972-04-25 | Syntex Corp | Drug glycerol ketals |
| US3855248A (en) | 1972-05-08 | 1974-12-17 | Monsanto Co | Dioxolane polycarboxylates |
| GB1427918A (en) | 1972-05-26 | 1976-03-10 | Shell Int Research | Herbicidal glycerol acetals |
| US4133800A (en) * | 1974-01-28 | 1979-01-09 | Imperial Chemical Industries Limited | Polyester production |
| US4105595A (en) * | 1974-09-17 | 1978-08-08 | Bayer Aktiengesellschaft | Process for the production of highly elastic polyurethane foams |
| US4005210A (en) | 1975-07-03 | 1977-01-25 | Estee Lauder, Inc. | Protein containing emollient composition for a skin moisturizer |
| US4153064A (en) * | 1975-07-11 | 1979-05-08 | Daicel Ltd. | Cigarette filters |
| SU722912A1 (ru) | 1978-03-06 | 1980-03-25 | Уфимский Нефтяной Институт | Способ получени 5-метил/-4оксо3,6,8-триоксабицикло/ (3,2,1)-октана |
| DE2811982A1 (de) * | 1978-03-18 | 1979-09-27 | Huels Chemische Werke Ag | Verfahren zur herstellung von hochmolekularem poly(ethylenterephthalat) |
| EP0012543B1 (en) | 1978-11-30 | 1983-05-11 | Imperial Chemical Industries Plc | Compositions containing 1,3-dioxolanes as emollients |
| US4205157A (en) * | 1979-04-02 | 1980-05-27 | The Goodyear Tire & Rubber Company | Method for production of high molecular weight polyester with low catalyst level and low carboxyl content |
| US4724240A (en) | 1981-03-23 | 1988-02-09 | Wickhen Products, Inc. | Lattice-entrapped emollient-moisturizer composition |
| JPS57197235A (en) | 1981-05-28 | 1982-12-03 | Kao Corp | Preparation of 2-hydroxy-3-alkoxypropyl glyceryl ether |
| KR840001591A (ko) * | 1981-09-29 | 1984-05-07 | 구라바야시 이꾸시로 | 당케탈류의 제조방법 |
| US4737426A (en) | 1985-05-15 | 1988-04-12 | Ciba-Geigy Corporation | Cyclic acetals or ketals of beta-keto esters or amides |
| US5013543A (en) | 1986-06-12 | 1991-05-07 | Revlon, Inc. | Cosmetic eyeliner formulation |
| US4792411A (en) * | 1986-12-29 | 1988-12-20 | The Lubrizol Corporation | Dioxolanes and thio analogs, derivatives thereof and lubricants and fuels containing same |
| US4923891A (en) | 1987-09-24 | 1990-05-08 | G. D. Searle & Co. | Leukotriene LTD4 and LTB4 antagonists |
| US4897497A (en) * | 1988-04-26 | 1990-01-30 | Biofine Incorporated | Lignocellulose degradation to furfural and levulinic acid |
| JPH0284327A (ja) | 1988-09-21 | 1990-03-26 | Toppan Printing Co Ltd | 艶変化模様を有する金属化粧板の製造方法 |
| US5028667A (en) * | 1989-09-29 | 1991-07-02 | E.I. Du Pont De Nemours And Company | Yttrium and rare earth compounds catalyzed lactone polymerization |
| US5095098A (en) * | 1989-09-29 | 1992-03-10 | E. I. Du Pont De Nemours And Company | Yttrium and rare earth compounds catalyzed lactone polymerization |
| FR2662079B1 (fr) | 1990-05-18 | 1993-11-05 | Oreal | Emulsion cosmetique filtrante comprenant un filtre uv-a et un filtre uv-b et son utilisation pour la protection de la peau contre les radiations ultraviolettes. |
| JPH04217972A (ja) * | 1990-07-30 | 1992-08-07 | Mitsuo Okahara | 新規なカルボン酸塩誘導体及びそれよりなる分解性界面活性剤 |
| JP2800437B2 (ja) | 1991-02-06 | 1998-09-21 | 日本電気株式会社 | デバイスシミュレーション方法 |
| US5093111A (en) | 1991-03-11 | 1992-03-03 | Kolmar Laboratories Inc. | Lipstick composition comprising cetearyl isononanoate, a sesquistearate and isopropyl hydroxystearate |
| DE4110973A1 (de) | 1991-04-05 | 1992-10-08 | Haarmann & Reimer Gmbh | Mittel mit physiologischem kuehleffekt und fuer diese mittel geeignete wirksame verbindungen |
| US5292859A (en) * | 1992-12-22 | 1994-03-08 | E. I. Du Pont De Nemours And Company | Rare earth metal coordination compounds as lactone polymerization catalysts |
| US5208297A (en) * | 1991-12-30 | 1993-05-04 | E. I. Du Pont De Nemours And Company | Rare earth metal coordination compounds as lactone polymerization catalysts |
| US5455025A (en) | 1992-04-02 | 1995-10-03 | Croda, Inc. | Non-aqueous emollient compositions for topical application |
| US5210108A (en) * | 1992-07-29 | 1993-05-11 | E. I. Du Pont De Nemours And Company | Degradable foam materials |
| ES2100664T3 (es) | 1992-11-25 | 1997-06-16 | Unilever Nv | Tensoactivos de alquiliden glicerol y composiciones detergentes que los contienen. |
| EP0683662B1 (de) | 1993-02-11 | 1998-06-17 | Beiersdorf Aktiengesellschaft | Wasserfeste kosmetische oder dermatologische lichtschutzzubereitungen |
| US5202413A (en) * | 1993-02-16 | 1993-04-13 | E. I. Du Pont De Nemours And Company | Alternating (ABA)N polylactide block copolymers |
| US5342969A (en) * | 1993-03-03 | 1994-08-30 | E. I. Du Pont De Nemours And Company | Recovery of hydroxycarboxylic acid values from poly(hydroxycarboxylic acids) |
| CA2119535C (en) | 1993-05-26 | 1998-04-21 | Michael L. Jackson | Water reducible polyester and resin composition for a flexible plastic primer |
| US5419848A (en) | 1993-07-02 | 1995-05-30 | Buckeye International, Inc. | Aqueous degreaser emulsion compositions |
| US5434239A (en) * | 1993-10-18 | 1995-07-18 | E. I. Du Pont De Nemours And Company | Continuous polyester process |
| JPH07163382A (ja) * | 1993-12-13 | 1995-06-27 | Kao Corp | ジグリセリン−１−エステルの製造方法 |
| US5516459A (en) | 1994-08-12 | 1996-05-14 | Buckeye International, Inc. | Aircraft cleaning/degreasing compositions |
| DE4432839A1 (de) * | 1994-09-15 | 1996-03-21 | Zimmer Ag | Verfahren zur Einstellung des Trübungsgrades von Ethylenterephthalat-Polymeren |
| EP0703260A1 (en) * | 1994-09-21 | 1996-03-27 | Tonen Corporation | Aliphatic polyester and a process for the preparation thereof |
| US6034118A (en) * | 1994-11-04 | 2000-03-07 | Gilead Sciences, Inc. | Thiepane compounds |
| US5585341A (en) | 1995-02-27 | 1996-12-17 | Buckeye International, Inc. | Cleaner/degreaser concentrate compositions |
| NZ311281A (en) * | 1995-06-07 | 1999-11-29 | Tetra Plastics | Inflated and sealed membrane of polyurethane including a polyester polyol |
| US5608105A (en) | 1995-06-07 | 1997-03-04 | Biofine Incorporated | Production of levulinic acid from carbohydrate-containing materials |
| US5886136A (en) | 1995-09-12 | 1999-03-23 | Nippon Zeon Co., Ltd. | Pattern forming process |
| US6083490A (en) | 1995-11-06 | 2000-07-04 | M&J Consultants Pty Ltd | UV absorbing compositions |
| US6010995A (en) | 1995-12-28 | 2000-01-04 | Buckeye International, Inc. | No/low volatile organic compound cleaner/degreaser composition |
| US6239087B1 (en) | 1996-03-22 | 2001-05-29 | The Procter & Gamble Company | Detergent compositions containing fragrance precursors and the fragrance precursors themselves |
| US5859263A (en) * | 1996-05-22 | 1999-01-12 | Board Of Regents University Of Nebraska Lincoln | Method and apparatus for production of levulinic acid via reactive extrusion |
| US5705087A (en) * | 1996-05-31 | 1998-01-06 | The United States Of America As Represented By The Secretary Of The Navy | Fuel system icing inhibitor and deicing composition |
| CZ47999A3 (cs) | 1996-08-12 | 1999-12-15 | The Procter & Gamble Company | Prostředky zjemňující textilie dodávané během máchání a způsob úpravy textilií |
| DE19647395A1 (de) * | 1996-11-15 | 1998-05-20 | Basf Ag | Verfahren zur Herstellung von cyclischen Acetalen oder Ketalen |
| US6130195A (en) | 1997-11-03 | 2000-10-10 | Kyzen Corporation | Cleaning compositions and methods for cleaning using cyclic ethers and alkoxy methyl butanols |
| US6036925A (en) | 1997-12-17 | 2000-03-14 | S. C. Johnson & Son, Inc. | Air freshener taper candle product |
| CA2322810A1 (en) * | 1998-03-04 | 1999-09-10 | Ato B.V. | Bicyclooctane derivatives as plasticisers |
| US5998092A (en) * | 1998-05-27 | 1999-12-07 | Clariant International, Ltd. | Water soluble negative-working photoresist composition |
| US7220469B2 (en) * | 1998-11-13 | 2007-05-22 | Daicel Chemical Industries, Ltd. | Aliphatic copolyester resin, a preparation method, an aliphatic polyester resin composition, uses thereof, a coating composition, a particle-state composition for agriculture and gardening coated by degradable layer |
| JP4287546B2 (ja) | 1999-07-27 | 2009-07-01 | 花王株式会社 | グリセリルエーテルの製法 |
| CA2395051A1 (en) * | 1999-12-10 | 2001-06-14 | Jens-Peter Wiegner | Catalyst systems for polycondensation reactions |
| JP4132821B2 (ja) * | 2000-04-27 | 2008-08-13 | 帝人株式会社 | ポリエステルの連続製造方法 |
| GB0015381D0 (en) | 2000-06-26 | 2000-08-16 | Acma Ltd | Particulate metal oxide |
| US6528025B1 (en) * | 2000-06-26 | 2003-03-04 | Roche Vitamins Inc. | Process of manufacturing equipment for preparing acetals and ketals |
| US6926309B1 (en) | 2000-06-28 | 2005-08-09 | Eastman Kodak Company | Modification of receiver surface to reject stamp cancellation information |
| US6271279B1 (en) * | 2000-07-10 | 2001-08-07 | Bayer Corporation | High resilient flexible urethane foam and flexible molded foams based on allophanate modified isocyanates |
| JP3956089B2 (ja) | 2000-08-08 | 2007-08-08 | 信越化学工業株式会社 | アセタール化合物及びその製造方法 |
| US6627181B1 (en) | 2000-10-23 | 2003-09-30 | Pro Strong Inc | Single and multi layered nail lacquers |
| US7078076B2 (en) | 2001-02-14 | 2006-07-18 | Metal Coatings International Inc. | Particulate metal alloy coating for providing corrosion protection |
| WO2002090479A1 (en) | 2001-05-04 | 2002-11-14 | The Procter & Gamble Company | Perfumed particles and articles containing the same |
| DE60323936D1 (de) * | 2002-01-14 | 2008-11-20 | Gen Hospital Corp | Bioabbaubare polyketale, verfahren zu ihrer herstellung sowie ihre verwendung |
| ES2201894B2 (es) * | 2002-01-18 | 2005-03-01 | Industrial Management, S.A | Procedimiento para producir combustibles biodiesel con propiedades mejoradas a baja temperatura. |
| EP1472463B1 (en) | 2002-01-31 | 2005-06-08 | Cean Company S.P.A. | Connecting device for tubular elements |
| US6825364B2 (en) | 2002-03-05 | 2004-11-30 | Curators Of The University Of Missouri | Dioxiranyl tetraoxaspiro [5.5] undecanes |
| CN1643116A (zh) * | 2002-04-01 | 2005-07-20 | 纳幕尔杜邦公司 | 由生物质和烯烃制备乙酰丙酸酯和甲酸酯 |
| US7094395B1 (en) | 2002-04-25 | 2006-08-22 | Access Business Group International Llc | Pigment dispersion and related method of manufacture |
| DE10218916A1 (de) * | 2002-04-27 | 2003-11-06 | Degussa | Verfahren zur Herstellung von Acetalen und Ketalen mit Hilfe mehrstufiger Pervaporation oder Dampfpermeation |
| DE10219028A1 (de) | 2002-04-29 | 2003-11-06 | Bayer Ag | Herstellung und Verwendung von hochmolekularen aliphatischen Polycarbonaten |
| JP3850762B2 (ja) | 2002-07-10 | 2006-11-29 | ポリプラスチックス株式会社 | ポリアセタール系樹脂組成物及びその製造方法 |
| JP4677550B2 (ja) * | 2002-08-14 | 2011-04-27 | 独立行政法人産業技術総合研究所 | 環状エステル化合物 |
| CA2440530A1 (en) | 2002-09-11 | 2004-03-11 | Henkel Kommanditgesellschaft Auf Aktien | Coating removal compositions |
| JP3947149B2 (ja) | 2002-10-28 | 2007-07-18 | 高砂香料工業株式会社 | 消臭剤組成物 |
| US6669929B1 (en) | 2002-12-30 | 2003-12-30 | Colgate Palmolive Company | Dentifrice containing functional film flakes |
| AU2003303519C1 (en) | 2002-12-31 | 2010-08-12 | Nektar Therapeutics | Polymeric reagents comprising a ketone or a related functional group |
| US20040157759A1 (en) | 2003-02-07 | 2004-08-12 | Buckeye International, Inc. | Stripper formulations and process |
| WO2004099173A1 (en) | 2003-05-12 | 2004-11-18 | Theracarb Inc. | Multivalent inhibitors of serum amyloid p component |
| EP1639040A1 (en) * | 2003-06-13 | 2006-03-29 | Agri-Polymerix, LLC | Biopolymer structures and components |
| DE10335061B4 (de) * | 2003-07-31 | 2005-11-17 | Wacker-Chemie Gmbh | Verfahren zur Herstellung von OH-geschützten [4-(2,6-damino-9H-purin-9-yl)-1,3-dioxolan-2-yl]methanol-Derivaten |
| WO2005040288A2 (en) | 2003-10-21 | 2005-05-06 | The Sepron Company, L.C. | Chemiluminescent paint projectiles and method of preparation |
| CN101940536B (zh) | 2003-12-16 | 2013-12-04 | 高露洁-棕榄公司 | 口腔和个人护理组合物及方法 |
| US7378549B2 (en) | 2004-01-26 | 2008-05-27 | Shell Oil Company | Process for the reactive extractive extraction of levulinic acid |
| WO2005097723A2 (en) | 2004-03-24 | 2005-10-20 | E.I. Dupont De Nemours And Company | PREPARATION OF LEVULINIC ACID ESTERS FROM α-ANGELICA LACTONE AND ALCOHOLS |
| AU2005228873A1 (en) | 2004-03-24 | 2005-10-13 | Archer-Daniels-Midland Company | Vegetable based dioxanone derivatives, synthesis and uses thereof |
| WO2005097724A1 (en) | 2004-03-24 | 2005-10-20 | E.I. Dupont De Nemours And Company | Preparation of levulinic acid esters from alpha-angelica lactone and alcohols |
| DE102004017097A1 (de) | 2004-04-07 | 2005-11-10 | Clariant Gmbh | Copolymerisierbare Polyalkylenglykol-Makromonomere, deren Herstellung und Verwendung |
| US20060041155A1 (en) * | 2004-08-23 | 2006-02-23 | Biobased Chemical | Method of preparing a hydroxy functional vegetable oil |
| JP4776303B2 (ja) | 2004-11-22 | 2011-09-21 | 独立行政法人科学技術振興機構 | 含フッ素化合物の製造方法、含フッ素化合物、含フッ素ポリマー、及び含フッ素ポリマーを用いた光学材料若しくは電気材料 |
| US7585833B2 (en) | 2005-02-17 | 2009-09-08 | Givaudan Fragrances Corporation | Malodor covering perfumery |
| US7501062B2 (en) | 2005-02-22 | 2009-03-10 | Shell Oil Company | Process for permeation enhanced reactive extraction of levulinic acid |
| EP1954140B1 (en) | 2005-11-22 | 2013-05-29 | Segetis, Inc. | Glycerol levulinate ketals and their use |
| KR101337124B1 (ko) | 2005-11-22 | 2013-12-05 | 세게티스, 인코포레이티드. | 에폭시화 지방산 에스테르를 갖는 레불린산 유도체의부가물 및 그의 용도 |
| US8026378B2 (en) * | 2005-11-22 | 2011-09-27 | Segetis, Inc. | Glyceryl ether compounds and their use |
| JP2009523896A (ja) | 2006-01-20 | 2009-06-25 | アーチャー・ダニエルズ・ミッドランド カンパニー | 反応性可塑剤および合体溶剤としてのレブリン酸エステル誘導体 |
| US7662758B2 (en) * | 2006-06-13 | 2010-02-16 | The Lubrizol Corporation | Polymeric polyol esters used in metalworking fluids |
| KR101455409B1 (ko) | 2006-07-18 | 2014-10-27 | 가부시키가이샤 아데카 | 수계 도료 조성물 |
| DE102006046249B4 (de) | 2006-09-28 | 2019-07-11 | Symrise Ag | Mischungen umfassend alpha-Ambrinolalkylether und 2-Alkoxy-9-methylen-2,6,6-trimethylbicyclo[3.3.1]nonane als Riech- und Aromastoffe |
| EP1923041A1 (de) | 2006-10-20 | 2008-05-21 | Symrise GmbH & Co. KG | Verwendung von C10-C14-Alkandiolen zur Herstellung eines Mittels zur Prophylaxe und/oder Behandlung von Malassezia-induzierter Schuppenbildung, sowie Zubereitungen enthaltend C10-C14-Alkandiole |
| DE102006055470A1 (de) | 2006-11-24 | 2008-05-29 | Evonik Degussa Gmbh | Ketomethioninketale und deren Derivate |
| US8486994B2 (en) | 2007-01-18 | 2013-07-16 | Evolva Sa | Prodrugs of substituted 1,3-dioxanes and their uses |
| MX2009008576A (es) | 2007-02-09 | 2009-08-18 | Procter & Gamble | Sistemas de perfume. |
| ES2561482T3 (es) | 2007-02-15 | 2016-02-26 | Centre De Recherche Sur Les Biotechnologies Marine | Monoglicéridos de ácido graso poliinsaturado, derivados, y sus usos |
| BRPI0816422A2 (pt) | 2007-09-04 | 2017-05-16 | Segetis Inc | compostos de cetal a partir de polióis e oxocarboxilatos. |
| BRPI0818370A2 (pt) | 2007-10-09 | 2017-05-16 | Segetis Inc | métodos de fabricar cetais e acetais |
| GB0722824D0 (en) | 2007-11-22 | 2008-01-02 | Givaudan Sa | Organic compounds |
| US8222194B2 (en) | 2008-05-09 | 2012-07-17 | Rhodia Operations | Cleaning compositions incorporating green solvents and methods for use |
| KR20100029978A (ko) | 2008-09-09 | 2010-03-18 | 에스케이에너지 주식회사 | 가소제 및 이를 포함한 폴리염화비닐 수지 조성물 |
| US8575367B2 (en) | 2008-09-25 | 2013-11-05 | Segetis, Inc. | Ketal ester derivatives |
| BRPI0922127A2 (pt) | 2008-12-23 | 2016-09-06 | Segetis Inc | composto, formulação, artigo, polímero e método para fabricar poliamida. |
| CA2796883A1 (en) | 2010-05-10 | 2011-11-17 | Segetis, Inc. | Personal care formulations containing alkyl ketal esters and methods of manufacture |
-
2006
- 2006-11-22 EP EP06838270.4A patent/EP1954140B1/en active Active
- 2006-11-22 CA CA2630744A patent/CA2630744C/en active Active
- 2006-11-22 PL PL06838270T patent/PL1954140T3/pl unknown
- 2006-11-22 ES ES06838270T patent/ES2416337T3/es active Active
- 2006-11-22 BR BRPI0618901-6A patent/BRPI0618901A2/pt not_active Application Discontinuation
- 2006-11-22 RU RU2008124895A patent/RU2472790C2/ru not_active IP Right Cessation
- 2006-11-22 DK DK06838270.4T patent/DK1954140T3/da active
- 2006-11-22 KR KR1020087014887A patent/KR101390488B1/ko active IP Right Grant
- 2006-11-22 IN IN2471KO2008 patent/IN263389B/en unknown
- 2006-11-22 AU AU2006318475A patent/AU2006318475B2/en not_active Ceased
- 2006-11-22 CN CN201310070713.0A patent/CN103396393B/zh active Active
- 2006-11-22 JP JP2008542439A patent/JP5305918B2/ja not_active Expired - Fee Related
- 2006-11-22 WO PCT/US2006/045200 patent/WO2007062118A2/en active Application Filing
- 2006-11-22 SG SG2008038986A patent/SG142841A1/en unknown
- 2006-11-22 CN CN2006800490485A patent/CN101346067B/zh active Active
- 2006-11-22 US US11/915,549 patent/US8053468B2/en active Active
- 2006-11-22 MY MYPI20081718A patent/MY166613A/en unknown
-
2008
- 2008-05-21 MX MX2008006562A patent/MX301032B/es active IP Right Grant
-
2009
- 2009-07-14 HK HK09106356.6A patent/HK1126934A1/xx not_active IP Right Cessation
-
2011
- 2011-07-15 US US13/184,064 patent/US8178701B2/en active Active
-
2012
- 2012-04-12 US US13/445,297 patent/US8492433B2/en active Active
-
2013
- 2013-07-15 US US13/941,687 patent/US8906961B2/en active Active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5305918B2 (ja) | グリセロールレブリネートケタール類とその使用 | |
| MX2008006562A (es) | Acetales de levuminato de glicerol y su uso | |
| US8436042B2 (en) | Adducts of levulinic derivatives with epoxidized fatty acid esters and uses thereof | |
| US8546519B2 (en) | Polyketal compounds, synthesis, and applications | |
| JP2009519901A5 (US20080242721A1-20081002-C00060.png) | ||
| AU2012202244B2 (en) | Adducts of Levulinic Derivatives With Epoxidized Fatty Acid Esters and Uses Thereof | |
| Sinisi | Design of biobased additives for tuning the properties of biopolymers | |
| PL236221B1 (pl) | Sposób otrzymywania nieftalanowego plastyfikatora poliestrowego | |
| MX2008006565A (es) | Aductos de derivados levulinicos con esteres de acido graso epoxidados y sus usos |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20091110 |
|
| A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20100115 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100120 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20100115 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120703 |
|
| A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20121003 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130528 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130625 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 5305918 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |