JP2014503018A - ポリマー組成物および方法 - Google Patents
ポリマー組成物および方法 Download PDFInfo
- Publication number
- JP2014503018A JP2014503018A JP2013548583A JP2013548583A JP2014503018A JP 2014503018 A JP2014503018 A JP 2014503018A JP 2013548583 A JP2013548583 A JP 2013548583A JP 2013548583 A JP2013548583 A JP 2013548583A JP 2014503018 A JP2014503018 A JP 2014503018A
- Authority
- JP
- Japan
- Prior art keywords
- polymer composition
- group
- acid
- certain embodiments
- optionally substituted
- 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.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 145
- 239000000203 mixture Substances 0.000 title claims abstract description 144
- 238000000034 method Methods 0.000 title abstract description 18
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 179
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 156
- 239000004417 polycarbonate Substances 0.000 claims abstract description 156
- 150000002118 epoxides Chemical group 0.000 claims abstract description 48
- 125000000524 functional group Chemical group 0.000 claims abstract description 19
- 239000004593 Epoxy Substances 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 37
- -1 pentaerythritol diester Chemical class 0.000 claims description 35
- 150000001261 hydroxy acids Chemical class 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 239000011593 sulfur Substances 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 12
- 150000002009 diols Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 150000005846 sugar alcohols Polymers 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 9
- 229920000570 polyether Polymers 0.000 claims description 9
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 8
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 229920000379 polypropylene carbonate Polymers 0.000 claims description 7
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 6
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229920001634 Copolyester Polymers 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 5
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 4
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 claims description 4
- 229940035437 1,3-propanediol Drugs 0.000 claims description 4
- UNVGBIALRHLALK-UHFFFAOYSA-N 1,5-Hexanediol Chemical compound CC(O)CCCCO UNVGBIALRHLALK-UHFFFAOYSA-N 0.000 claims description 4
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 4
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 4
- 235000013772 propylene glycol Nutrition 0.000 claims description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- WHBMMWSBFZVSSR-GSVOUGTGSA-N (R)-3-hydroxybutyric acid Chemical compound C[C@@H](O)CC(O)=O WHBMMWSBFZVSSR-GSVOUGTGSA-N 0.000 claims description 2
- WHBMMWSBFZVSSR-VKHMYHEASA-N (S)-3-hydroxybutyric acid Chemical compound C[C@H](O)CC(O)=O WHBMMWSBFZVSSR-VKHMYHEASA-N 0.000 claims description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- FQXGHZNSUOHCLO-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3-cyclobutanediol Chemical compound CC1(C)C(O)C(C)(C)C1O FQXGHZNSUOHCLO-UHFFFAOYSA-N 0.000 claims description 2
- KXZLHMICGMACLR-UHFFFAOYSA-N 2-(hydroxymethyl)-2-pentylpropane-1,3-diol Chemical compound CCCCCC(CO)(CO)CO KXZLHMICGMACLR-UHFFFAOYSA-N 0.000 claims description 2
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 claims description 2
- JVGDVPVEKJSWIO-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)cyclohexyl]ethanol Chemical compound OCCC1CCC(CCO)CC1 JVGDVPVEKJSWIO-UHFFFAOYSA-N 0.000 claims description 2
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 claims description 2
- 229930182843 D-Lactic acid Natural products 0.000 claims description 2
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 claims 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 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 2
- XDODWINGEHBYRT-UHFFFAOYSA-N [2-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCCC1CO XDODWINGEHBYRT-UHFFFAOYSA-N 0.000 claims description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 claims description 2
- 229960004106 citric acid Drugs 0.000 claims description 2
- NUUPJBRGQCEZSI-UHFFFAOYSA-N cyclopentane-1,3-diol Chemical compound OC1CCC(O)C1 NUUPJBRGQCEZSI-UHFFFAOYSA-N 0.000 claims description 2
- 229940022769 d- lactic acid Drugs 0.000 claims description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims description 2
- 229960004275 glycolic acid Drugs 0.000 claims description 2
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- 229940051250 hexylene glycol Drugs 0.000 claims description 2
- 229960002479 isosorbide Drugs 0.000 claims description 2
- 229960000448 lactic acid Drugs 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000011976 maleic acid Substances 0.000 claims description 2
- 229960002510 mandelic acid Drugs 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical group CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims 3
- 229940043375 1,5-pentanediol Drugs 0.000 claims 1
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 claims 1
- JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical compound CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 claims 1
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- ZWVAVPQCOZURMT-UHFFFAOYSA-N cyclohexane-1,2-diol cyclohexane-1,3-diol Chemical compound C1(O)CC(O)CCC1.C1(O)C(O)CCCC1 ZWVAVPQCOZURMT-UHFFFAOYSA-N 0.000 claims 1
- SYEPGZUBYZSFTQ-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.OC.C1CCCCC1 SYEPGZUBYZSFTQ-UHFFFAOYSA-N 0.000 claims 1
- 150000002390 heteroarenes Chemical group 0.000 claims 1
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims 1
- 239000002131 composite material Substances 0.000 abstract description 31
- 239000012038 nucleophile Substances 0.000 abstract description 14
- 238000007142 ring opening reaction Methods 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 229920006334 epoxy coating Polymers 0.000 abstract description 8
- 239000011248 coating agent Substances 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 abstract description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 36
- 125000004432 carbon atom Chemical group C* 0.000 description 31
- 229910052727 yttrium Inorganic materials 0.000 description 22
- 239000000654 additive Substances 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 18
- 239000001569 carbon dioxide Substances 0.000 description 18
- 229910002092 carbon dioxide Inorganic materials 0.000 description 18
- 229920001897 terpolymer Polymers 0.000 description 17
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 16
- 125000003700 epoxy group Chemical group 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000012986 chain transfer agent Substances 0.000 description 8
- 238000007334 copolymerization reaction Methods 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
- 150000001336 alkenes Chemical group 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 229940100198 alkylating agent Drugs 0.000 description 5
- 239000002168 alkylating agent Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 4
- FDWQGNULGGFFDP-UHFFFAOYSA-N 5-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C=CC1CCCC2OC12 FDWQGNULGGFFDP-UHFFFAOYSA-N 0.000 description 4
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 4
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000000269 nucleophilic effect Effects 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 3
- 229920000049 Carbon (fiber) Polymers 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 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
- 150000001412 amines Chemical class 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 239000004917 carbon fiber Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 150000002081 enamines Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- OMKZWUPRGQMQJC-UHFFFAOYSA-N n'-[3-(dimethylamino)propyl]propane-1,3-diamine Chemical compound CN(C)CCCNCCCN OMKZWUPRGQMQJC-UHFFFAOYSA-N 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 239000000779 smoke Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003419 tautomerization reaction Methods 0.000 description 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 2
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical group [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical class OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 2
- 229920004552 POLYLITE® Polymers 0.000 description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229920002214 alkoxylated polymer Polymers 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- KEIQPMUPONZJJH-UHFFFAOYSA-N dicyclohexylmethanediamine Chemical compound C1CCCCC1C(N)(N)C1CCCCC1 KEIQPMUPONZJJH-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 125000004475 heteroaralkyl group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 2
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- JCUZDQXWVYNXHD-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diamine Chemical compound NCCC(C)CC(C)(C)CN JCUZDQXWVYNXHD-UHFFFAOYSA-N 0.000 description 1
- CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 1
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 description 1
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
- JWTVQZQPKHXGFM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diamine Chemical compound CC(C)(N)CCC(C)(C)N JWTVQZQPKHXGFM-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- POTQBGGWSWSMCX-UHFFFAOYSA-N 3-[2-(3-aminopropoxy)ethoxy]propan-1-amine Chemical compound NCCCOCCOCCCN POTQBGGWSWSMCX-UHFFFAOYSA-N 0.000 description 1
- NVOQLEBSTHAENC-UHFFFAOYSA-N 3-[6-(3-aminopropoxy)hexoxy]propan-1-amine Chemical compound NCCCOCCCCCCOCCCN NVOQLEBSTHAENC-UHFFFAOYSA-N 0.000 description 1
- WRDNCFQZLUCIRH-UHFFFAOYSA-N 4-(7-azabicyclo[2.2.1]hepta-1,3,5-triene-7-carbonyl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(=O)N1C2=CC=C1C=C2 WRDNCFQZLUCIRH-UHFFFAOYSA-N 0.000 description 1
- HMJBXEZHJUYJQY-UHFFFAOYSA-N 4-(aminomethyl)octane-1,8-diamine Chemical compound NCCCCC(CN)CCCN HMJBXEZHJUYJQY-UHFFFAOYSA-N 0.000 description 1
- JHCBFGGESJQAIQ-UHFFFAOYSA-N 4-[(4-amino-3,5-dimethylcyclohexyl)methyl]-2,6-dimethylcyclohexan-1-amine Chemical compound C1C(C)C(N)C(C)CC1CC1CC(C)C(N)C(C)C1 JHCBFGGESJQAIQ-UHFFFAOYSA-N 0.000 description 1
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- BDBZTOMUANOKRT-UHFFFAOYSA-N 4-[2-(4-aminocyclohexyl)propan-2-yl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1C(C)(C)C1CCC(N)CC1 BDBZTOMUANOKRT-UHFFFAOYSA-N 0.000 description 1
- HEHBHCRLIYBRAN-UHFFFAOYSA-N 5-ethyl-7-oxabicyclo[4.1.0]heptane Chemical compound CCC1CCCC2OC12 HEHBHCRLIYBRAN-UHFFFAOYSA-N 0.000 description 1
- GJEZBVHHZQAEDB-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexane Chemical compound C1CCC2OC21 GJEZBVHHZQAEDB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000009261 D 400 Substances 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 229920000271 Kevlar® Polymers 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- DUFKCOQISQKSAV-UHFFFAOYSA-N Polypropylene glycol (m w 1,200-3,000) Chemical group CC(O)COC(C)CO DUFKCOQISQKSAV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 229920002522 Wood fibre Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 description 1
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229940061720 alpha hydroxy acid Drugs 0.000 description 1
- 150000001280 alpha hydroxy acids Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229920006231 aramid fiber Polymers 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 150000001277 beta hydroxy acids Chemical class 0.000 description 1
- XMSVKICKONKVNM-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-diamine Chemical compound C1CC2(N)C(N)CC1C2 XMSVKICKONKVNM-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- CMCJNODIWQEOAI-UHFFFAOYSA-N bis(2-butoxyethyl)phthalate Chemical compound CCCCOCCOC(=O)C1=CC=CC=C1C(=O)OCCOCCCC CMCJNODIWQEOAI-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000002639 bone cement Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- ULEAQRIQMIQDPJ-UHFFFAOYSA-N butane-1,2-diamine Chemical compound CCC(N)CN ULEAQRIQMIQDPJ-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 230000021235 carbamoylation Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- GMAYNBHUHYFCPZ-UHFFFAOYSA-N cyclohexyl-(4,4-dimethylcyclohexyl)methanediamine Chemical compound C1CC(C)(C)CCC1C(N)(N)C1CCCCC1 GMAYNBHUHYFCPZ-UHFFFAOYSA-N 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- FLBJFXNAEMSXGL-UHFFFAOYSA-N het anhydride Chemical compound O=C1OC(=O)C2C1C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl FLBJFXNAEMSXGL-UHFFFAOYSA-N 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 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
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 210000003041 ligament Anatomy 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
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002557 mineral fiber Substances 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- HWMMYAWUTCKNKH-UHFFFAOYSA-N n,n'-dicyclohexylhexane-1,6-diamine Chemical compound C1CCCCC1NCCCCCCNC1CCCCC1 HWMMYAWUTCKNKH-UHFFFAOYSA-N 0.000 description 1
- BEPGHZIEOVULBU-UHFFFAOYSA-N n,n'-diethylpropane-1,3-diamine Chemical compound CCNCCCNCC BEPGHZIEOVULBU-UHFFFAOYSA-N 0.000 description 1
- UQUPIHHYKUEXQD-UHFFFAOYSA-N n,n′-dimethyl-1,3-propanediamine Chemical compound CNCCCNC UQUPIHHYKUEXQD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000005545 phthalimidyl group Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003366 poly(p-phenylene terephthalamide) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- HAMAGKWXRRTWCJ-UHFFFAOYSA-N pyrido[2,3-b][1,4]oxazin-3-one Chemical compound C1=CN=C2OC(=O)C=NC2=C1 HAMAGKWXRRTWCJ-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
- C08G64/0216—Aliphatic polycarbonates saturated containing a chain-terminating or -crosslinking agent
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/42—Chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
【選択図】なし
Description
本出願は、2011年1月6日に出願された米国特許仮出願第61/430,312号に基づく優先権を主張するものであり、その出願の内容全体が、参照により本明細書に援用される。
(技術分野)
定義
I)エポキシ末端基を有する脂肪族ポリカーボネート鎖
RaおよびRbは独立して、各発生時に、−H、ハロゲン、随意に置換されたC1−20脂肪族基、随意に置換されたC1−20ヘテロ脂肪族基、随意に置換されたアシルオキシ基、随意に置換されたアシル基、随意に置換されたアルコキシ基、随意に置換された炭素環式基、および随意に置換された複素環式基からなる群から選択され、いずれか2つ以上のRaおよびRb基は随意に、介在する原子と一緒になって、1つ以上のヘテロ原子を随意に含有する1つ以上の随意に置換された環を形成してよく、
Rcは独立して、各発生時に、−H、随意に置換されたC1−20脂肪族基、随意に置換されたC1−20ヘテロ脂肪族基、随意に置換された炭素環式基、および随意に置換された複素環式基からなる群から選択され、いずれか2つ以上のRc基は随意に、介在する原子と一緒になって、1つ以上のヘテロ原子を随意に含有する1つ以上の随意に置換された環を形成してよく、
qは、1以上10以下である。
pは、1以上12以下であり、
Ra′は独立して、1つ以上の随意に存在する置換基を表し、存在する場合には、ハロゲン、随意に置換されたC1−20脂肪族基、随意に置換されたC1−20ヘテロ脂肪族基、随意に置換された炭素環式基、および随意に置換された複素環式基からなる群からそれぞれ選択され、複数のRa′が存在する場合には、それらの2つ以上が随意に、介在する原子と一緒になって、1つ以上のヘテロ原子を随意に含有する1つ以上の随意に置換された環を形成し得る。
nは独立して、各発生時に、2〜1000であり、
xおよびyは、それぞれ独立して0〜6であり、xおよびyの合計は、2以上6以下である。
特定の実施形態において、上記構造中の部分
複合物
製造物品
実施例
他の実施形態
Claims (64)
- エポキシ官能基を有する脂肪族ポリカーボネート鎖を含む、ポリマー組成物であって、
a)前記脂肪族ポリカーボネートが、構造:
式中、R1、R2、R3、およびR4が独立して、前記ポリマー鎖内での各発生時に、−H、フッ素、および随意に置換されたC1−20脂肪族基からなる群から選択され、R1、R2、R3、およびR4のうちのいずれか2つ以上が随意に、介在する原子と一緒になって、1つ以上のヘテロ原子を随意に含有する1つ以上の随意に置換された環を形成してよく、
c)前記脂肪族ポリカーボネート鎖の分子量が、平均で約500g/mol〜約500,000g/molの範囲である、
ポリマー組成物。 - 前記エポキシ官能基が、前記脂肪族カーボネート鎖の1つ以上の末端に配置される、請求項1に記載のポリマー組成物。
- 前記脂肪族カーボネート鎖の前記末端に配置された前記エポキシ官能基が独立して、
- 式:
Yが、各発生時に、エポキシド含有部分であり、各Yが、同じであっても、または異なってもよく、
xおよびyがそれぞれ独立して、0〜6であり、xおよびyの合計が、2以上6以下であり、
nが独立して、各発生時に、2〜1000である、
請求項2に記載のポリマー組成物。 - Yが独立して、各発生時に、
式中、RaおよびRbが独立して、各発生時に、−H、ハロゲン、随意に置換されたC1−20脂肪族基、随意に置換されたC1−20ヘテロ脂肪族基、随意に置換されたアシルオキシ基、随意に置換されたアシル基、随意に置換されたアルコキシ基、随意に置換された炭素環式基、および随意に置換された複素環式基からなる群から選択され、任意の2つ以上のRaおよびRb基が随意に、介在する原子と一緒になって、1つ以上のヘテロ原子を随意に含有する1つ以上の随意に置換された環を形成してよく、
Rcが独立して、各発生時に、−H、随意に置換されたC1−20脂肪族基、随意に置換されたC1−20ヘテロ脂肪族基、随意に置換された炭素環式基、および随意に置換された複素環式基からなる群から選択され、任意の2つ以上のRc基が随意に、介在する原子および任意のRaまたはRb基と一緒になって、1つ以上のヘテロ原子を随意に含有する1つ以上の随意に置換された環を形成してよく、
Rdが独立して、各発生時に、ハロゲン、−NO2、−CN、−SRy、−S(O)Ry、−S(O)2Ry、−NRyC(O)Ry、−OC(O)Ry、−CO2Ry、−NCO、−N3、−ORy、−OC(O)N(Ry)2、−N(Ry)2、−NRyC(O)Ry、−NRyC(O)ORy;またはC1−20脂肪族からなる群から選択される、随意に置換されたラジカル;C1−20ヘテロ脂肪族;フェニル;3〜8員の飽和もしくは部分的に不飽和の単環式炭素環、7〜14炭素の飽和、部分的に不飽和、もしくは芳香族の多環式炭素環;窒素、酸素、もしくは硫黄から独立して選択される1〜4個のヘテロ原子を有する5〜6員の単環式ヘテロアリール環;窒素、酸素、もしくは硫黄から独立して選択される1〜3個のヘテロ原子を有する3〜8員の飽和もしくは部分的に不飽和の複素環式環;窒素、酸素、もしくは硫黄から独立して選択される1〜5個のヘテロ原子を有する6〜12員の多環式飽和もしくは部分的に不飽和の複素環;あるいは窒素、酸素、もしくは硫黄から独立して選択される1〜5個のヘテロ原子を有する8〜10員の二環式ヘテロアリール環からなる群から選択され、
Ryの各発生が独立して、−H、またはC1−6脂肪族、3〜7員の複素環式、フェニル、および8〜10員のアリールからなる群から選択される、随意に置換されたラジカルであり、2つ以上の隣接したRd基が一緒になって、0〜4個のヘテロ原子を含有する、随意に置換された飽和、部分的に不飽和、もしくは芳香族の5〜12員の環を形成することができ、
pが、1以上6以下であり、
qが、1以上10以下である、
請求項4に記載のポリマー組成物。 - Yが独立して、
- Yが、式:
- 式:
Yが、各発生時に、エポキシド含有部分であり、各Yが、同じであっても、または異なってもよく、
nが独立して、各発生時に、2〜1000であり、
x′が、1以上5以下である、
請求項1に記載のポリマー組成物。 -
- 前記二価アルコールが、C2−40ジオールを含む、請求項9に記載のポリマー組成物。
- 前記二価アルコールが、1,2−エタンジオール、1,2−プロパンジオール、1,3−プロパンジオール、1,2−ブタンジオール、1,3−ブタンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、2,2−ジメチルプロパン−1,3−ジオール、2−ブチル−2−エチルプロパン−1,3−ジオール、1,5−ヘキサンジオール、1,6−ヘキサンジオール、1,8−オクタンジオール、1,10−デカンジオール、1,12−ドデカンジオール、2,2,4,4−テトラメチルシクロブタン−1,3−ジオール、1,3−シクロペンタンジオール、1,2−シクロヘキサンジオール、1,3−シクロヘキサンジオール、1,4−シクロヘキサンジオール、1,2−シクロヘキサンジメタノール、1,3−シクロヘキサンジメタノール、1,4−シクロヘキサンジメタノール、1,4−シクロヘキサンジエタノール、イソソルビド、グリセロールモノエステル、グリセロールモノエーテル、トリメチロールプロパンモノエステル、トリメチロールプロパンモノエーテル、ペンタエリスリトールジエステル、ペンタエリスリトールジエーテル、およびこれらのいずれかのアルコキシ化誘導体からなる群から選択される、請求項10に記載のポリマー組成物。
- 前記二価アルコールが、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、ヘキシレングリコール、高級ポリ(エチレングリコール)、例えば、220〜約2000g/molの数平均分子量を有するもの、ジプロピレングリコール、トリプロピレングリコール、および高級ポリ(プロピレングリコール)、例えば、234〜約2000g/molの数平均分子量を有するものからなる群から選択される、請求項10に記載のポリマー組成物。
- 前記二価アルコールが、二酸、ジオール、またはヒドロキシ酸からなる群から選択される化合物のアルコキシ化誘導体を含む、請求項10に記載のポリマー組成物。
- 前記アルコキシ化誘導体が、エトキシ化またはプロポキシ化された化合物を含む、請求項13に記載のポリマー組成物。
- 前記二価アルコールが、ポリマージオールを含む、請求項9に記載のポリマー組成物。
- 前記ポリマージオールが、ポリエーテル、ポリエステル、ヒドロキシ末端ポリオレフィン、およびポリエーテル−コポリエステル、ポリエーテルポリカーボネート、ポリカーボネート−コポリエステル、ならびにそれらのいずれかのアルコキシ化類似体からなる群から選択される、請求項15に記載のポリマー組成物。
- 前記ポリマージオールが、約2000g/mol未満の平均分子量を有する、請求項15に記載のポリマー組成物。
-
- 前記多価アルコールが、C2−40トリオールを含む、請求項18に記載のポリマー組成物。
- 式:
- 前記多価アルコールが、グリセロール、1,2,4−ブタントリオール、2−(ヒドロキシメチル)−1,3−プロパンジオール;ヘキサントリオール、トリメチロールプロパン、トリメチロールエタン、トリメチロールヘキサン、1,4−シクロヘキサントリメタノール、ペンタエリスリトールモノエステル、ペンタエリスリトールモノエーテル、およびこれらのいずれかのアルコキシ化類似体からなる群から選択される、請求項20に記載のポリマー組成物。
- 前記多価アルコールが、3個を超えるヒドロキシル基を有するC2−40ポリオールを含む、請求項18に記載のポリマー組成物。
-
- 式:
-
- 式:
- 前記ジカルボン酸が、フタル酸、イソフタル酸、テレフタル酸、マレイン酸、コハク酸、マロン酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、およびアゼライン酸からなる群から選択される、請求項25に記載のポリマー組成物。
- 前記ポリカルボン酸が、
-
- 式:
- 前記ヒドロキシ酸が、α−ヒドロキシ酸である、請求項30に記載のポリマー組成物。
- 前記ヒドロキシ酸が、グリコール酸、DL−乳酸、D−乳酸、L−乳酸、クエン酸、およびマンデル酸からなる群から選択される、請求項30に記載のポリマー組成物。
- 前記ヒドロキシ酸が、β−ヒドロキシ酸である、請求項30に記載のポリマー組成物。
- 前記ヒドロキシ酸が、3−ヒドロキシプロピオン酸、DL3−ヒドロキシブチル酸、D−3ヒドロキシブチル酸、L3−ヒドロキシブチル酸、DL−3−ヒドロキシ吉草酸、D−3−ヒドロキシ吉草酸、L−3−ヒドロキシ吉草酸、サリチル酸、およびサリチル酸の誘導体からなる群から選択される、請求項30に記載のポリマー組成物。
- 前記ヒドロキシ酸が、α−ωヒドロキシ酸である、請求項30に記載のポリマー組成物。
- 前記ヒドロキシ酸が、随意に置換されたC3−20脂肪族α−ωヒドロキシ酸およびオリゴマーエステルからなる群から選択される、請求項30に記載のポリマー組成物。
- 前記ヒドロキシ酸が、
- 前記脂肪族ポリカーボネート鎖中の前記部分
- 前記脂肪族ポリカーボネート鎖中の前記部分
- 前記脂肪族ポリカーボネート鎖中の前記
- 前記脂肪族ポリカーボネート鎖中の前記
- 前記脂肪族ポリカーボネート鎖が、
約500g/mol〜約20,000g/molのMnと、
平均で90%を超えるカーボネート結合と、を有し、
前記末端基の少なくとも90%が、エポキシド含有部分を含む、
請求項38に記載のポリマー組成物。 - 92%を超えるカーボネート結合を含む、請求項42に記載のポリマー組成物。
- 95%を超えるカーボネート結合を含む、請求項42に記載のポリマー組成物。
- 97%を超えるカーボネート結合を含む、請求項42に記載のポリマー組成物。
- 99%を超えるカーボネート結合を含む、請求項42に記載のポリマー組成物。
- 約500〜約100,000g/molのMnを有する、請求項42に記載のポリマー組成物。
- 約800〜約5,000g/molのMnを有する、請求項42に記載のポリマー組成物。
- 約1,000〜約4,000g/molのMnを有する、請求項42に記載のポリマー組成物。
- 約1,000g/molのMnを有する、請求項42に記載のポリマー組成物。
- 約2,000g/molのMnを有する、請求項42に記載のポリマー組成物。
- 約3,000g/molのMnを有する、請求項42に記載のポリマー組成物。
- 約4,000g/molのMnを有する、請求項42に記載のポリマー組成物。
- 約5,000g/molのMnを有する、請求項42に記載のポリマー組成物。
- 約8,000g/molのMnを有する、請求項42に記載のポリマー組成物。
- 前記脂肪族ポリカーボネートが、1.5未満の多分散性指数を有する、請求項38に記載のポリマー組成物。
- 前記脂肪族ポリカーボネートが、1.4未満の多分散性指数を有する、請求項56に記載のポリマー組成物。
- 前記脂肪族ポリカーボネートが、1.3未満の多分散性指数を有する、請求項56に記載のポリマー組成物。
- 前記脂肪族ポリカーボネートが、1.2未満の多分散性指数を有する、請求項56に記載のポリマー組成物。
- 前記脂肪族ポリカーボネートが、1.1未満の多分散性指数を有する、請求項56に記載のポリマー組成物。
- 式:
Yが独立して、各発生時に、
前記ポリマー中のnが、平均で約5〜約400の整数である、請求項1に記載のポリマー組成物。 -
- 前記ポリ(プロピレンカーボネート)鎖中の隣接するモノマー基の85%超が、頭尾配向される、請求項61に記載のポリマー組成物。
- 前記ポリ(プロピレンカーボネート)鎖中の隣接するモノマー基の90%超が、頭尾配向される、請求項61に記載のポリマー組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161430312P | 2011-01-06 | 2011-01-06 | |
US61/430,312 | 2011-01-06 | ||
PCT/US2012/020523 WO2012094619A1 (en) | 2011-01-06 | 2012-01-06 | Polymer compositions and methods |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2014503018A true JP2014503018A (ja) | 2014-02-06 |
JP6105486B2 JP6105486B2 (ja) | 2017-03-29 |
Family
ID=46457730
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013548583A Active JP6105486B2 (ja) | 2011-01-06 | 2012-01-06 | ポリマー組成物および方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US8952104B2 (ja) |
EP (1) | EP2661453A4 (ja) |
JP (1) | JP6105486B2 (ja) |
KR (2) | KR101942034B1 (ja) |
CN (1) | CN103403058B (ja) |
WO (1) | WO2012094619A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016139831A1 (ja) * | 2015-03-02 | 2016-09-09 | 国立大学法人東京農工大学 | 熱分解性バインダー |
US10640643B2 (en) | 2016-04-01 | 2020-05-05 | National University Corporation Tokyo University Of Agriculture And Technology | Pyrolytic binder |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101913673B1 (ko) | 2008-09-08 | 2018-11-01 | 사우디 아람코 테크놀로지스 컴퍼니 | 폴리카보네이트 폴리올 조성물 |
CN103153278B (zh) | 2010-08-27 | 2016-01-20 | 诺沃梅尔公司 | 聚合物组合物和方法 |
JP6105486B2 (ja) | 2011-01-06 | 2017-03-29 | ノボマー, インコーポレイテッド | ポリマー組成物および方法 |
PL2707224T3 (pl) | 2011-05-09 | 2018-08-31 | Saudi Aramco Technologies Company | Kompozycje polimerowe i sposoby |
CN104428370A (zh) | 2012-04-16 | 2015-03-18 | 诺沃梅尔公司 | 粘合剂组合物和方法 |
US9388277B2 (en) | 2012-05-24 | 2016-07-12 | Novomer, Inc. | Polycarbonate polyol compositions and methods |
WO2014031811A1 (en) | 2012-08-24 | 2014-02-27 | Novomer, Inc. | Metal complexes |
WO2015154001A1 (en) | 2014-04-03 | 2015-10-08 | Novomer, Inc. | Aliphatic polycarbonate polyol compositions |
WO2018160726A1 (en) * | 2017-02-28 | 2018-09-07 | Georgia Tech Research Corporation | Low dielectric constant porous epoxy-based dielectric |
FR3072382B1 (fr) * | 2017-10-16 | 2019-11-01 | Roquette Freres | Oligocarbonates diepoxydes, leur procede de fabrication et leurs utilisations |
FR3072385B1 (fr) * | 2017-10-16 | 2019-11-01 | Roquette Freres | Oligocarbonates vinyl ester, leur procede de fabrication et leurs utilisations |
KR102241367B1 (ko) * | 2018-01-05 | 2021-04-15 | 주식회사 엘지화학 | 블록 공중합체 |
KR102286545B1 (ko) * | 2018-01-05 | 2021-08-04 | 주식회사 엘지화학 | 블록 공중합체 |
EP3781609A1 (en) | 2018-04-18 | 2021-02-24 | Saudi Aramco Technologies Company | End-group isomerization of poly(alkylene carbonate) polymers |
US11180609B2 (en) | 2018-08-02 | 2021-11-23 | Saudi Aramco Technologies Company | Sustainable polymer compositions and methods |
EP3856820A1 (en) | 2018-09-24 | 2021-08-04 | Saudi Aramco Technologies Company | Polycarbonate block copolymers and methods thereof |
KR20200115166A (ko) | 2019-03-26 | 2020-10-07 | 주식회사 엘지화학 | 트리블록 공중합체 및 이의 제조 방법 |
KR102315714B1 (ko) | 2020-07-20 | 2021-10-20 | 부산대학교 산학협력단 | 그래핀-탄소나노튜브 복합 섬유의 제조방법 및 상기 제조 방법에 의해 제조되는 그래핀-탄소나노튜브 복합 섬유의 제조 장치 |
KR102334643B1 (ko) * | 2021-04-09 | 2021-12-02 | 주식회사 엘지화학 | 블록 공중합체 |
WO2023213745A1 (en) * | 2022-05-04 | 2023-11-09 | Covestro Deutschland Ag | Process for preparing a polycarbonate by metal catalyzed cross coupling |
CN115594835B (zh) * | 2022-10-18 | 2023-08-22 | 佛山科学技术学院 | 一种脂肪族聚碳酸酯双子表面活性剂及其制备方法 |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01163213A (ja) * | 1987-10-19 | 1989-06-27 | General Electric Co <Ge> | カルボキシ官能化ポリカーボネート及びその製造法 |
JPH03220233A (ja) * | 1989-10-11 | 1991-09-27 | Daicel Chem Ind Ltd | ポリカーボネートポリオール |
JPH0570584A (ja) * | 1991-09-11 | 1993-03-23 | Kuraray Co Ltd | 脂環式ポリカーボネートおよびその製造方法 |
JPH0762216A (ja) * | 1993-08-27 | 1995-03-07 | Daicel Chem Ind Ltd | 熱可塑性樹脂組成物 |
JPH09319102A (ja) * | 1996-05-28 | 1997-12-12 | Idemitsu Kosan Co Ltd | 電子写真感光体 |
JPH10282668A (ja) * | 1997-04-10 | 1998-10-23 | Mitsubishi Chem Corp | 感放射線性樹脂材料及び感放射線性塗布組成物 |
JP2008101191A (ja) * | 2006-09-22 | 2008-05-01 | Idemitsu Kosan Co Ltd | 末端に反応基を有するポリカーボネート樹脂を用いた複合材料 |
WO2010028362A1 (en) * | 2008-09-08 | 2010-03-11 | Novomer, Inc. | Polycarbonate polyol compositions and methods |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4959411A (en) * | 1987-10-19 | 1990-09-25 | General Electric Company | Preparation of copolymer from carboxy-functionalized polycarbonate and nucleophilic polymer |
US4851507A (en) | 1988-03-21 | 1989-07-25 | Arco Chemical Technology, Inc. | Melt processable aliphatic polycarbonate terpolymers |
US5342554A (en) | 1993-01-07 | 1994-08-30 | Gencorp Inc. | Vinyl-terminated polyesters and polycarbonates for flexibilizing and improving the toughness of compositions from unsaturated polyesters and fiber reinforced plastics made from them |
IT1266775B1 (it) | 1993-11-05 | 1997-01-21 | Mediolanum Farmaceutici Srl | Poliesterepolicarbonati ad alto peso molecolare e loro uso per la preparazione di matrici bioerodibili |
US9052438B2 (en) | 2005-04-08 | 2015-06-09 | Johnson & Johnson Vision Care, Inc. | Ophthalmic devices comprising photochromic materials with reactive substituents |
US7718755B2 (en) | 2007-10-18 | 2010-05-18 | Sabic Innovative Plastics Ip B.V. | Aliphatic diol-based polycarbonates, method of making, and articles formed therefrom |
US7671164B2 (en) | 2007-10-18 | 2010-03-02 | Sabic Innovative Plastics Ip B.V. | Aliphatic polycarbonates, methods of making, and articles formed therefrom |
KR101449521B1 (ko) * | 2007-12-13 | 2014-10-13 | 가부시끼가이샤 도꾸야마 | 포토크로믹 경화성 조성물 및 경화체 |
CN102164987B (zh) * | 2008-08-22 | 2015-07-08 | 诺沃梅尔公司 | 用于合成聚合物的催化剂和方法 |
KR102028314B1 (ko) | 2008-09-17 | 2019-10-07 | 사우디 아람코 테크놀로지스 컴퍼니 | 폴리카보네이트의 정제 |
CA2742119C (en) * | 2008-11-01 | 2018-05-29 | Novomer, Inc. | Polycarbonate block copolymers |
US8575245B2 (en) * | 2008-12-23 | 2013-11-05 | Novomer, Inc. | Tunable polymer compositions |
CN101805507B (zh) * | 2010-04-13 | 2012-03-14 | 深圳市金缙业科技有限公司 | 灯罩用聚碳酸酯树脂组合物及其制备方法 |
CN103153278B (zh) | 2010-08-27 | 2016-01-20 | 诺沃梅尔公司 | 聚合物组合物和方法 |
JP6105486B2 (ja) | 2011-01-06 | 2017-03-29 | ノボマー, インコーポレイテッド | ポリマー組成物および方法 |
-
2012
- 2012-01-06 JP JP2013548583A patent/JP6105486B2/ja active Active
- 2012-01-06 KR KR1020137020621A patent/KR101942034B1/ko active IP Right Grant
- 2012-01-06 WO PCT/US2012/020523 patent/WO2012094619A1/en active Application Filing
- 2012-01-06 US US13/977,059 patent/US8952104B2/en active Active
- 2012-01-06 EP EP12732379.8A patent/EP2661453A4/en active Pending
- 2012-01-06 KR KR1020197001819A patent/KR102067954B1/ko active IP Right Grant
- 2012-01-06 CN CN201280011235.XA patent/CN103403058B/zh active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH01163213A (ja) * | 1987-10-19 | 1989-06-27 | General Electric Co <Ge> | カルボキシ官能化ポリカーボネート及びその製造法 |
JPH03220233A (ja) * | 1989-10-11 | 1991-09-27 | Daicel Chem Ind Ltd | ポリカーボネートポリオール |
JPH0570584A (ja) * | 1991-09-11 | 1993-03-23 | Kuraray Co Ltd | 脂環式ポリカーボネートおよびその製造方法 |
JPH0762216A (ja) * | 1993-08-27 | 1995-03-07 | Daicel Chem Ind Ltd | 熱可塑性樹脂組成物 |
JPH09319102A (ja) * | 1996-05-28 | 1997-12-12 | Idemitsu Kosan Co Ltd | 電子写真感光体 |
JPH10282668A (ja) * | 1997-04-10 | 1998-10-23 | Mitsubishi Chem Corp | 感放射線性樹脂材料及び感放射線性塗布組成物 |
JP2008101191A (ja) * | 2006-09-22 | 2008-05-01 | Idemitsu Kosan Co Ltd | 末端に反応基を有するポリカーボネート樹脂を用いた複合材料 |
WO2010028362A1 (en) * | 2008-09-08 | 2010-03-11 | Novomer, Inc. | Polycarbonate polyol compositions and methods |
JP2012502143A (ja) * | 2008-09-08 | 2012-01-26 | ノボマー, インコーポレイテッド | ポリカーボネートポリオール組成物および方法 |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016139831A1 (ja) * | 2015-03-02 | 2016-09-09 | 国立大学法人東京農工大学 | 熱分解性バインダー |
KR20170125871A (ko) * | 2015-03-02 | 2017-11-15 | 고꾸리쯔 다이가꾸호우징 도쿄노우코우다이가쿠 | 열분해성 바인더 |
JPWO2016139831A1 (ja) * | 2015-03-02 | 2017-12-14 | 国立大学法人東京農工大学 | 熱分解性バインダー |
US10759901B2 (en) | 2015-03-02 | 2020-09-01 | National University Corporation Tokyo University Of Agriculture And Technology | Thermally decomposable binder |
KR102270299B1 (ko) | 2015-03-02 | 2021-06-28 | 고꾸리쯔 다이가꾸호우징 도쿄노우코우다이가쿠 | 열분해성 바인더 |
US10640643B2 (en) | 2016-04-01 | 2020-05-05 | National University Corporation Tokyo University Of Agriculture And Technology | Pyrolytic binder |
Also Published As
Publication number | Publication date |
---|---|
JP6105486B2 (ja) | 2017-03-29 |
KR101942034B1 (ko) | 2019-01-25 |
EP2661453A1 (en) | 2013-11-13 |
KR20190014099A (ko) | 2019-02-11 |
CN103403058A (zh) | 2013-11-20 |
US20130281633A1 (en) | 2013-10-24 |
US8952104B2 (en) | 2015-02-10 |
KR20140035882A (ko) | 2014-03-24 |
KR102067954B1 (ko) | 2020-01-21 |
EP2661453A4 (en) | 2018-01-10 |
WO2012094619A1 (en) | 2012-07-12 |
CN103403058B (zh) | 2016-12-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6105486B2 (ja) | ポリマー組成物および方法 | |
Kadam et al. | Biodegradable biobased epoxy resin from karanja oil | |
Lavilla et al. | High Tg bio-based aliphatic polyesters from bicyclic D-mannitol | |
Wu et al. | Fully isohexide-based polyesters: Synthesis, characterization, and structure–properties relations | |
Maisonneuve et al. | Structure–properties relationship of fatty acid-based thermoplastics as synthetic polymer mimics | |
DK2707224T3 (en) | POLYMER COMPOSITIONS AND PROCEDURES | |
JP6097245B2 (ja) | エチレンオキシドと二酸化炭素とのポリマー | |
US9399701B2 (en) | Polymer compositions and methods | |
Karami et al. | Non-isocyanate polyurethane thermoset based on a bio-resourced star-shaped epoxy macromonomer in comparison with a cyclocarbonate fossil-based epoxy resin: A preliminary study on thermo-mechanical and antibacterial properties | |
Yum et al. | Synthesis and characterization of isosorbide based polycarbonates | |
Wu et al. | An investigation of polyamides based on isoidide-2, 5-dimethyleneamine as a green rigid building block with enhanced reactivity | |
CA2736636A1 (en) | Ketal ester derivatives | |
Pang et al. | Copolymerization of natural camphor-derived rigid diol with various dicarboxylic acids: Access to biobased polyesters with various properties | |
Kamps et al. | Microphase separation: enabling isosorbide-based polycarbonates with improved property profile | |
Neumann et al. | Unlocking the Processability and Recyclability of Biobased Poly (limonene carbonate) | |
Petrović et al. | Epoxy resins and composites from epoxidized linseed oil copolymers with cyclohexene oxide | |
Yin et al. | Biobased Linear and Crystallizable Polyhydroxy (amide-urethane) s from Diglycerol Bis (cyclic carbonate) and the Polyamides of Dimer Fatty Acids | |
JP4672688B2 (ja) | ポリ乳酸樹脂用改質剤 | |
KR20170121156A (ko) | 지방족 폴리카보네이트 및 시클릭 카보네이트로부터 지방족 폴리카보네이트를 제조하는 방법 | |
Gao et al. | Thermally stable poly (propylene carbonate) synthesized by copolymerizing with bulky naphthalene containing monomer | |
Takase et al. | Semi‐interpenetrating polymer networks composed of diisocyanate‐bridged 4‐arm star‐shaped l‐lactide oligomers and poly (ε‐caprolactone) | |
TWI703171B (zh) | 聯苯二甲酸共聚酯及其製法 | |
JP2011521080A (ja) | アルカノールアミドに由来するエポキシ樹脂の付加物及びその製造方法 | |
KR101697391B1 (ko) | 코폴리카보네이트 수지 및 이를 포함하는 성형품 | |
Zhao et al. | Design and synthesis of biodegradable copolyester poly (ε‐caprolactone‐co‐d, l‐lactide) with four pendent functional groups |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20141226 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20141226 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20150918 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150929 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20151203 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160323 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20160624 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20160822 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20161220 |
|
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: 20170206 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20170302 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6105486 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 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
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 |