CA2853068A1 - Multifunctional monomers, methods for making multifunctional monomers, polymerizable compositions and products formed therefrom - Google Patents
Multifunctional monomers, methods for making multifunctional monomers, polymerizable compositions and products formed therefrom Download PDFInfo
- Publication number
- CA2853068A1 CA2853068A1 CA2853068A CA2853068A CA2853068A1 CA 2853068 A1 CA2853068 A1 CA 2853068A1 CA 2853068 A CA2853068 A CA 2853068A CA 2853068 A CA2853068 A CA 2853068A CA 2853068 A1 CA2853068 A1 CA 2853068A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- heterocyclyl
- cycloalkyl
- aryl
- heteroaryl
- 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.)
- Abandoned
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 193
- 238000000034 method Methods 0.000 title claims abstract description 92
- 239000000203 mixture Substances 0.000 title claims abstract description 70
- -1 coatings Substances 0.000 claims abstract description 114
- XJDDLMJULQGRLU-UHFFFAOYSA-N 1,3-dioxane-4,6-dione Chemical compound O=C1CC(=O)OCO1 XJDDLMJULQGRLU-UHFFFAOYSA-N 0.000 claims abstract description 67
- 229920000642 polymer Polymers 0.000 claims abstract description 42
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 41
- 239000000853 adhesive Substances 0.000 claims abstract description 17
- 230000001070 adhesive effect Effects 0.000 claims abstract description 17
- 238000000576 coating method Methods 0.000 claims abstract description 10
- 239000000835 fiber Substances 0.000 claims abstract description 9
- 239000000565 sealant Substances 0.000 claims abstract description 9
- 238000000465 moulding Methods 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 99
- 125000005647 linker group Chemical group 0.000 claims description 96
- 238000006243 chemical reaction Methods 0.000 claims description 87
- 125000003118 aryl group Chemical group 0.000 claims description 69
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 65
- 125000003545 alkoxy group Chemical group 0.000 claims description 56
- 125000001072 heteroaryl group Chemical group 0.000 claims description 56
- 125000000623 heterocyclic group Chemical group 0.000 claims description 56
- 239000003054 catalyst Substances 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 36
- 125000003342 alkenyl group Chemical group 0.000 claims description 36
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 34
- 150000002148 esters Chemical class 0.000 claims description 34
- 230000002378 acidificating effect Effects 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 125000001188 haloalkyl group Chemical group 0.000 claims description 30
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 29
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 27
- 125000004423 acyloxy group Chemical group 0.000 claims description 27
- 125000004414 alkyl thio group Chemical group 0.000 claims description 27
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 239000003381 stabilizer Substances 0.000 claims description 24
- 150000002009 diols Chemical class 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 229920001223 polyethylene glycol Polymers 0.000 claims description 17
- 239000002202 Polyethylene glycol Substances 0.000 claims description 16
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 239000004593 Epoxy Substances 0.000 claims description 14
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 14
- 239000002952 polymeric resin Substances 0.000 claims description 14
- 229920005862 polyol Polymers 0.000 claims description 14
- 150000003077 polyols Chemical class 0.000 claims description 14
- 229920003002 synthetic resin Polymers 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000004417 polycarbonate Substances 0.000 claims description 12
- 229920000515 polycarbonate Polymers 0.000 claims description 12
- 229920002635 polyurethane Polymers 0.000 claims description 12
- 239000004814 polyurethane Substances 0.000 claims description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 11
- 229920000570 polyether Polymers 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 239000003352 sequestering agent Substances 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 239000006254 rheological additive Substances 0.000 claims description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 claims description 6
- 239000013008 thixotropic agent Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- 229920003052 natural elastomer Polymers 0.000 claims description 5
- 229920001194 natural rubber Polymers 0.000 claims description 5
- 239000003973 paint Substances 0.000 claims description 5
- 229920003051 synthetic elastomer Polymers 0.000 claims description 5
- 239000005061 synthetic rubber Substances 0.000 claims description 5
- 239000004753 textile Substances 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 4
- 230000002255 enzymatic effect Effects 0.000 claims description 4
- 235000011056 potassium acetate Nutrition 0.000 claims description 4
- 239000012744 reinforcing agent Substances 0.000 claims description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 4
- 239000002562 thickening agent Substances 0.000 claims description 4
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004255 Butylated hydroxyanisole Substances 0.000 claims description 3
- 239000004322 Butylated hydroxytoluene Substances 0.000 claims description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 3
- 235000019282 butylated hydroxyanisole Nutrition 0.000 claims description 3
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims description 3
- 229940043253 butylated hydroxyanisole Drugs 0.000 claims description 3
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 3
- 229940095259 butylated hydroxytoluene Drugs 0.000 claims description 3
- 239000008199 coating composition Substances 0.000 claims description 3
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 claims description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 3
- 229920006280 packaging film Polymers 0.000 claims description 3
- 239000012785 packaging film Substances 0.000 claims description 3
- 229920005594 polymer fiber Polymers 0.000 claims description 3
- 229920006254 polymer film Polymers 0.000 claims description 3
- 239000002516 radical scavenger Substances 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 3
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical class C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 claims description 2
- 229920000896 Ethulose Polymers 0.000 claims description 2
- 239000001859 Ethyl hydroxyethyl cellulose Substances 0.000 claims description 2
- 244000043261 Hevea brasiliensis Species 0.000 claims description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical compound COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 claims description 2
- 150000003983 crown ethers Chemical class 0.000 claims description 2
- 229960005215 dichloroacetic acid Drugs 0.000 claims description 2
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 claims description 2
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 claims description 2
- 229910021485 fumed silica Inorganic materials 0.000 claims description 2
- 235000019447 hydroxyethyl cellulose Nutrition 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
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- 239000001923 methylcellulose Substances 0.000 claims description 2
- 235000010981 methylcellulose Nutrition 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 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
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 1
- 229920006037 cross link polymer Polymers 0.000 claims 1
- 238000005809 transesterification reaction Methods 0.000 abstract description 33
- 230000015572 biosynthetic process Effects 0.000 abstract description 22
- 238000003786 synthesis reaction Methods 0.000 abstract description 12
- 239000002131 composite material Substances 0.000 abstract description 8
- 239000000976 ink Substances 0.000 abstract description 8
- 239000004094 surface-active agent Substances 0.000 abstract description 5
- 239000000047 product Substances 0.000 description 48
- BQHDXNZNSPVVKB-UHFFFAOYSA-N diethyl 2-methylidenepropanedioate Chemical compound CCOC(=O)C(=C)C(=O)OCC BQHDXNZNSPVVKB-UHFFFAOYSA-N 0.000 description 39
- 239000000463 material Substances 0.000 description 36
- 230000008569 process Effects 0.000 description 24
- 150000002500 ions Chemical class 0.000 description 18
- 239000007795 chemical reaction product Substances 0.000 description 15
- 239000007858 starting material Substances 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 238000001228 spectrum Methods 0.000 description 12
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 9
- 229920001971 elastomer Polymers 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- 239000005060 rubber Substances 0.000 description 9
- 238000004252 FT/ICR mass spectrometry Methods 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- 150000002690 malonic acid derivatives Chemical class 0.000 description 8
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 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 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 239000004014 plasticizer Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 6
- 238000005040 ion trap Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 229920001651 Cyanoacrylate Polymers 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 150000001793 charged compounds Chemical class 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 238000000132 electrospray ionisation Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229920000800 acrylic rubber Polymers 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000000855 fermentation Methods 0.000 description 4
- 230000004151 fermentation Effects 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 210000001724 microfibril Anatomy 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 229920000058 polyacrylate Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000012808 vapor phase Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229940121375 antifungal agent Drugs 0.000 description 3
- 239000003429 antifungal agent Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 3
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 3
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 239000012745 toughening agent Substances 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- CFEMBVVZPUEPPP-UHFFFAOYSA-N 2-methylbuta-1,3-diene;prop-2-enenitrile Chemical compound C=CC#N.CC(=C)C=C CFEMBVVZPUEPPP-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 2
- 238000006845 Michael addition reaction Methods 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- 108010084311 Novozyme 435 Proteins 0.000 description 2
- 229920000954 Polyglycolide Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 2
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- YWMLORGQOFONNT-UHFFFAOYSA-N [3-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC(CO)=C1 YWMLORGQOFONNT-UHFFFAOYSA-N 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229940009827 aluminum acetate Drugs 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 229960003280 cupric chloride Drugs 0.000 description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 229920002681 hypalon Polymers 0.000 description 2
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 2
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 2
- 239000011654 magnesium acetate Substances 0.000 description 2
- 235000011285 magnesium acetate Nutrition 0.000 description 2
- 229940069446 magnesium acetate Drugs 0.000 description 2
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical class NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 2
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- CMOAHYOGLLEOGO-UHFFFAOYSA-N oxozirconium;dihydrochloride Chemical compound Cl.Cl.[Zr]=O CMOAHYOGLLEOGO-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000002787 reinforcement Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000012720 thermal barrier coating Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical compound [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- YAXKTBLXMTYWDQ-UHFFFAOYSA-N 1,2,3-butanetriol Chemical compound CC(O)C(O)CO YAXKTBLXMTYWDQ-UHFFFAOYSA-N 0.000 description 1
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 1
- 229940083957 1,2-butanediol Drugs 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- YXRKNIZYMIXSAD-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O YXRKNIZYMIXSAD-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical class OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
- NOJXRHBIVBIMQY-UHFFFAOYSA-N 3-anilino-3-oxopropanoic acid Chemical class OC(=O)CC(=O)NC1=CC=CC=C1 NOJXRHBIVBIMQY-UHFFFAOYSA-N 0.000 description 1
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 1
- UJAWGGOCYUPCPS-UHFFFAOYSA-N 4-(2-phenylpropan-2-yl)-n-[4-(2-phenylpropan-2-yl)phenyl]aniline Chemical compound C=1C=C(NC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 UJAWGGOCYUPCPS-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229920001710 Polyorthoester Polymers 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000004830 Super Glue Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- GTVWRXDRKAHEAD-UHFFFAOYSA-N Tris(2-ethylhexyl) phosphate Chemical compound CCCCC(CC)COP(=O)(OCC(CC)CCCC)OCC(CC)CCCC GTVWRXDRKAHEAD-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- AXWSRHKJAQPNCQ-UHFFFAOYSA-N [Cu].[Li].[K] Chemical class [Cu].[Li].[K] AXWSRHKJAQPNCQ-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 229940024548 aluminum oxide Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- JINBYESILADKFW-UHFFFAOYSA-N aminomalonic acid Chemical class OC(=O)C(N)C(O)=O JINBYESILADKFW-UHFFFAOYSA-N 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000181 anti-adherent effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- KTKVKPXZWFQQAB-UHFFFAOYSA-N butane-1,4-diol 2-pentan-3-ylidenepropanedioic acid Chemical compound C(C)C(CC)=C(C(=O)O)C(=O)O.C(CCCO)O KTKVKPXZWFQQAB-UHFFFAOYSA-N 0.000 description 1
- KGKRHEYNGLETOQ-UHFFFAOYSA-N butane-1,4-diol dichloromethane Chemical compound ClCCl.OCCCCO KGKRHEYNGLETOQ-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- OIQPTROHQCGFEF-UHFFFAOYSA-L chembl1371409 Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-UHFFFAOYSA-L 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- MJSNUBOCVAKFIJ-LNTINUHCSA-N chromium;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Cr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MJSNUBOCVAKFIJ-LNTINUHCSA-N 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000001360 collision-induced dissociation Methods 0.000 description 1
- 239000012468 concentrated sample Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940014772 dimethyl sebacate Drugs 0.000 description 1
- RXJJVYBGRFLCOX-UHFFFAOYSA-N dioctyl pentanedioate Chemical compound CCCCCCCCOC(=O)CCCC(=O)OCCCCCCCC RXJJVYBGRFLCOX-UHFFFAOYSA-N 0.000 description 1
- 229940035422 diphenylamine Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000000119 electrospray ionisation mass spectrum Methods 0.000 description 1
- 239000002320 enamel (paints) Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000012732 erythrosine Nutrition 0.000 description 1
- 239000004174 erythrosine Substances 0.000 description 1
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000012738 indigotine Nutrition 0.000 description 1
- 239000004179 indigotine Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 238000011068 loading method Methods 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
- 229960000869 magnesium oxide Drugs 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002691 malonic acids Chemical class 0.000 description 1
- KKHUSADXXDNRPW-UHFFFAOYSA-N malonic anhydride Chemical compound O=C1CC(=O)O1 KKHUSADXXDNRPW-UHFFFAOYSA-N 0.000 description 1
- 231100000647 material safety data sheet Toxicity 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 1
- 238000000238 one-dimensional nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920002721 polycyanoacrylate Polymers 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000004060 quinone imines Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- OZWUZVBLUVAWMT-UHFFFAOYSA-N sodium;2-(3-hydroxy-2,4,5,7-tetraiodo-6-oxoxanthen-9-yl)benzoic acid Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C(O)=C(I)C=C21 OZWUZVBLUVAWMT-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- JNXDCMUUZNIWPQ-UHFFFAOYSA-N trioctyl benzene-1,2,4-tricarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C(C(=O)OCCCCCCCC)=C1 JNXDCMUUZNIWPQ-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical group 0.000 description 1
- BOSMZFBHAYFUBJ-UHFFFAOYSA-N tris(4-methylphenyl) phosphate Chemical compound C1=CC(C)=CC=C1OP(=O)(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 BOSMZFBHAYFUBJ-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229960000314 zinc acetate Drugs 0.000 description 1
- 235000013904 zinc acetate Nutrition 0.000 description 1
- 229960001296 zinc oxide Drugs 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/14—Esters having no free carboxylic acid groups, e.g. dialkyl maleates or fumarates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
- C07C49/796—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/794—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring
- C07C49/798—Ketones containing a keto group bound to a six-membered aromatic ring having unsaturation outside an aromatic ring containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/604—Polycarboxylic acid esters, the acid moiety containing more than two carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F116/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F116/36—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by a ketonic radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F128/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur
- C08F128/06—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur by a heterocyclic ring containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/14—Methyl esters, e.g. methyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/38—Esters containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
- C08F20/68—Esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/10—Esters
- C08F22/12—Esters of phenols or saturated alcohols
- C08F22/20—Esters containing oxygen in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F24/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F28/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur
- C08F28/06—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur by a heterocyclic ring containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- C08L33/16—Homopolymers or copolymers of esters containing halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L35/02—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D129/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Coating compositions based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Coating compositions based on derivatives of such polymers
- C09D129/12—Homopolymers or copolymers of unsaturated ketones
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09D133/16—Homopolymers or copolymers of esters containing halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D135/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D135/02—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D141/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09J133/16—Homopolymers or copolymers of esters containing halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J135/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J135/02—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Polyesters Or Polycarbonates (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Sealing Material Composition (AREA)
- Wrappers (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161549092P | 2011-10-19 | 2011-10-19 | |
| US201161549104P | 2011-10-19 | 2011-10-19 | |
| US201161549152P | 2011-10-19 | 2011-10-19 | |
| US61/549,092 | 2011-10-19 | ||
| US61/549,104 | 2011-10-19 | ||
| US61/549,152 | 2011-10-19 | ||
| PCT/US2012/060830 WO2013059473A2 (en) | 2011-10-19 | 2012-10-18 | Multifunctional monomers, methods for making multifunctional monomers, polymerizable compositions and products formed therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2853068A1 true CA2853068A1 (en) | 2013-04-25 |
Family
ID=48141622
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2853068A Abandoned CA2853068A1 (en) | 2011-10-19 | 2012-10-18 | Multifunctional monomers, methods for making multifunctional monomers, polymerizable compositions and products formed therefrom |
| CA2853073A Abandoned CA2853073A1 (en) | 2011-10-19 | 2012-10-18 | Methylene beta-diketone monomers, methods for making methylene beta-diketone monomers, polymerizable compositions and products formed therefrom |
| CA2853079A Abandoned CA2853079A1 (en) | 2011-10-19 | 2012-10-18 | Methylene beta-ketoester monomers, methods for making methylene beta-ketoester monomers, polymerizable compositions and products formed therefrom |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2853073A Abandoned CA2853073A1 (en) | 2011-10-19 | 2012-10-18 | Methylene beta-diketone monomers, methods for making methylene beta-diketone monomers, polymerizable compositions and products formed therefrom |
| CA2853079A Abandoned CA2853079A1 (en) | 2011-10-19 | 2012-10-18 | Methylene beta-ketoester monomers, methods for making methylene beta-ketoester monomers, polymerizable compositions and products formed therefrom |
Country Status (6)
| Country | Link |
|---|---|
| US (7) | US9221739B2 (https=) |
| EP (6) | EP3517523A1 (https=) |
| JP (3) | JP2014534969A (https=) |
| CA (3) | CA2853068A1 (https=) |
| MX (3) | MX360462B (https=) |
| WO (3) | WO2013059473A2 (https=) |
Families Citing this family (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9144796B1 (en) | 2009-04-01 | 2015-09-29 | Johnson Matthey Public Limited Company | Method of applying washcoat to monolithic substrate |
| US9279022B1 (en) | 2014-09-08 | 2016-03-08 | Sirrus, Inc. | Solution polymers including one or more 1,1-disubstituted alkene compounds, solution polymerization methods, and polymer compositions |
| US9249265B1 (en) | 2014-09-08 | 2016-02-02 | Sirrus, Inc. | Emulsion polymers including one or more 1,1-disubstituted alkene compounds, emulsion methods, and polymer compositions |
| US9828324B2 (en) | 2010-10-20 | 2017-11-28 | Sirrus, Inc. | Methylene beta-diketone monomers, methods for making methylene beta-diketone monomers, polymerizable compositions and products formed therefrom |
| US10414839B2 (en) | 2010-10-20 | 2019-09-17 | Sirrus, Inc. | Polymers including a methylene beta-ketoester and products formed therefrom |
| EP3517523A1 (en) | 2011-10-19 | 2019-07-31 | Sirrus, Inc. | Multifunctional monomers and methods for making them |
| CA2869115A1 (en) | 2012-03-30 | 2013-10-03 | Bioformix Inc. | Ink and coating formulations and polymerizable systems for producing the same |
| EP2831124B1 (en) | 2012-03-30 | 2016-10-05 | Sirrus, Inc. | Composite and laminate articles and polymerizable systems for producing the same |
| US10047192B2 (en) | 2012-06-01 | 2018-08-14 | Sirrus, Inc. | Optical material and articles formed therefrom |
| WO2014078689A1 (en) | 2012-11-16 | 2014-05-22 | Bioformix Inc. | Plastics bonding systems and methods |
| EP2926368B1 (en) | 2012-11-30 | 2020-04-08 | Sirrus, Inc. | Electronic assembly |
| CN105008321A (zh) | 2013-01-11 | 2015-10-28 | 瑟拉斯公司 | 经过双(羟甲基)丙二酸酯的途径获得亚甲基丙二酸酯的方法 |
| US9315597B2 (en) | 2014-09-08 | 2016-04-19 | Sirrus, Inc. | Compositions containing 1,1-disubstituted alkene compounds for preparing polymers having enhanced glass transition temperatures |
| US9416091B1 (en) * | 2015-02-04 | 2016-08-16 | Sirrus, Inc. | Catalytic transesterification of ester compounds with groups reactive under transesterification conditions |
| US10501400B2 (en) | 2015-02-04 | 2019-12-10 | Sirrus, Inc. | Heterogeneous catalytic transesterification of ester compounds with groups reactive under transesterification conditions |
| US9334430B1 (en) | 2015-05-29 | 2016-05-10 | Sirrus, Inc. | Encapsulated polymerization initiators, polymerization systems and methods using the same |
| US9217098B1 (en) | 2015-06-01 | 2015-12-22 | Sirrus, Inc. | Electroinitiated polymerization of compositions having a 1,1-disubstituted alkene compound |
| DE102017204525A1 (de) | 2016-03-23 | 2017-09-28 | Basf Se | Verbundfolienlaminate für flexible Verpackungen |
| US11015034B2 (en) | 2016-04-21 | 2021-05-25 | Zephyros, Inc. | Malonates and derivatives for in-situ films |
| US9518001B1 (en) | 2016-05-13 | 2016-12-13 | Sirrus, Inc. | High purity 1,1-dicarbonyl substituted-1-alkenes and methods for their preparation |
| JP2019517599A (ja) * | 2016-06-03 | 2019-06-24 | シラス・インコーポレイテッド | 末端1,1−二置換アルケンモノマーによって官能化されたポリマー及びその他の化合物ならびにその方法 |
| US10428177B2 (en) | 2016-06-03 | 2019-10-01 | Sirrus, Inc. | Water absorbing or water soluble polymers, intermediate compounds, and methods thereof |
| US9617377B1 (en) * | 2016-06-03 | 2017-04-11 | Sirrus, Inc. | Polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
| US9567475B1 (en) | 2016-06-03 | 2017-02-14 | Sirrus, Inc. | Coatings containing polyester macromers containing 1,1-dicarbonyl-substituted 1 alkenes |
| EP3464484B1 (en) * | 2016-06-03 | 2020-07-29 | Sirrus, Inc. | Water absorbing or water soluble polymers, intermediate compounds, and methods thereof |
| WO2017210084A1 (en) | 2016-06-03 | 2017-12-07 | Sirrus, Inc. | Water absorbing or water soluble polymers, intermediate compounds, and methods thereof |
| US10196481B2 (en) | 2016-06-03 | 2019-02-05 | Sirrus, Inc. | Polymer and other compounds functionalized with terminal 1,1-disubstituted alkene monomer(s) and methods thereof |
| WO2018022794A1 (en) | 2016-07-26 | 2018-02-01 | Ppg Industries Ohio, Inc. | Particles having surfaces functionalized with 1,1-di-activated vinyl compounds |
| CN109475903B (zh) | 2016-07-26 | 2021-11-26 | Ppg工业俄亥俄公司 | 含有1,1-二活化的乙烯基化合物产物的多层可固化组合物及相关工艺 |
| US11136469B2 (en) | 2016-07-26 | 2021-10-05 | Ppg Industries Ohio, Inc. | Acid-catalyzed curable coating compositions containing 1,1-di-activated vinyl compounds and related coatings and processes |
| ES2957658T3 (es) | 2016-07-26 | 2024-01-23 | Ppg Ind Ohio Inc | Composiciones de recubrimiento de poliuretano que contienen compuestos vinílicos 1,1-diactivados y recubrimientos y procesos relacionados |
| CN109476081B (zh) | 2016-07-26 | 2021-11-23 | Ppg工业俄亥俄公司 | 使用1,1-二活化的乙烯基化合物的三维印刷方法 |
| CN109642098B (zh) | 2016-07-26 | 2022-02-11 | Ppg工业俄亥俄公司 | 包含1,1-二活化的乙烯基化合物的可电沉积的涂料组合物 |
| US11634524B2 (en) | 2016-07-26 | 2023-04-25 | Ppg Industries Ohio, Inc. | Acid-catalyzed curable coating compositions containing 1,1 di-activated vinyl compounds and related coatings and processes |
| JP7498561B2 (ja) * | 2016-07-26 | 2024-06-12 | ピーピージー・インダストリーズ・オハイオ・インコーポレイテッド | 1,1-二活性化ビニル化合物を含有する硬化性組成物ならびに関連のコーティングおよび方法 |
| EP3515973B1 (en) | 2016-09-19 | 2025-10-29 | Zephyros Inc. | Malonate and cyanoacrylate adhesives for joining dissimilar materials |
| CN109844036A (zh) | 2016-09-19 | 2019-06-04 | 泽菲罗斯有限公司 | 聚丙二酸酯和氰基丙烯酸酯基混凝土表面密封剂 |
| US10934411B2 (en) | 2016-09-30 | 2021-03-02 | Ppg Industries Ohio, Inc. | Curable compositions containing 1,1-di-activated vinyl compounds that cure by pericyclic reaction mechanisms |
| CN109952330B (zh) * | 2016-11-09 | 2021-07-02 | 巴斯夫欧洲公司 | 聚氨酯-乙烯基混杂聚合物、其制法和它们的用途 |
| MY176736A (en) * | 2017-05-18 | 2020-08-20 | Namics Corp | Resin composition |
| KR102571880B1 (ko) | 2017-06-02 | 2023-08-28 | 아르끄마 프랑스 | 경화성 조성물 및 이의 용도 |
| CN107225048B (zh) * | 2017-07-01 | 2019-07-12 | 山东金城柯瑞化学有限公司 | 煤炭浮选剂 |
| US20200368997A1 (en) | 2017-09-13 | 2020-11-26 | Zephyros, Inc. | Composite structures for localized stiffening |
| JP6427848B1 (ja) * | 2017-10-17 | 2018-11-28 | ナミックス株式会社 | 樹脂組成物 |
| CN111278869B (zh) | 2017-10-31 | 2022-02-11 | 纳美仕有限公司 | 树脂组合物 |
| US11697738B2 (en) | 2017-12-27 | 2023-07-11 | Basf Se | Composition, its preparation method, and the use of the composition in construction application |
| WO2019137853A1 (en) | 2018-01-09 | 2019-07-18 | Basf Se | Compositions comprising polymerizable vinyl compounds, inorganic or organic fillers and their use |
| JP2021510755A (ja) * | 2018-01-12 | 2021-04-30 | シラス・インコーポレイテッド | 2つ以上のジカルボニル置換1アルケン単位を含有する化合物で架橋されたエマルジョンポリマー |
| KR102540734B1 (ko) | 2018-02-01 | 2023-06-08 | 삼성디스플레이 주식회사 | 유기발광표시장치 및 그의 제조방법 |
| WO2019195366A1 (en) | 2018-04-03 | 2019-10-10 | Sirrus, Inc. | Heterogeneous catalytic transesterification of ester compounds with groups reactive under transesterification conditions |
| US11028294B2 (en) | 2018-08-10 | 2021-06-08 | International Business Machines Corporation Armonk, New York | Acrylate-cyanoacrylate monomers |
| WO2020068916A1 (en) | 2018-09-26 | 2020-04-02 | Swimc Llc | Curable coating compositions |
| KR102816836B1 (ko) | 2018-10-05 | 2025-06-09 | 나믹스 가부시끼가이샤 | 수지 조성물 |
| JP7333638B2 (ja) * | 2018-10-09 | 2023-08-25 | ナミックス株式会社 | 2-メチレン-1,3-ジカルボニル化合物を硬化させるための硬化剤組成物 |
| JP7191979B2 (ja) | 2018-11-15 | 2022-12-19 | 株式会社日本触媒 | アクリル系樹脂組成物、架橋体および架橋体の製造方法 |
| JP7219594B2 (ja) * | 2018-11-15 | 2023-02-08 | 株式会社日本触媒 | 粘着剤組成物、及びそれを含む物品並びに粘着製品の製造方法 |
| WO2020123579A1 (en) | 2018-12-11 | 2020-06-18 | Sirrus, Inc. | Polymerization of 1,1-dicarbonyl 1-alkenes |
| WO2020123581A1 (en) | 2018-12-11 | 2020-06-18 | Sirrus, Inc. | Emulsion polymers of 1,1-dicarbonyl 1-alkenes of controlled particle size |
| DE102019219214A1 (de) | 2018-12-17 | 2020-06-18 | Basf Se | Zusammensetzungen, die multifunktionelle Vinylverbindungen in Miniemulsion umfassen, und ihre Verwendung als Vernetzer für Polymere |
| CN113348157A (zh) * | 2019-01-29 | 2021-09-03 | 株式会社日本触媒 | 养护剂、具有覆膜的水泥类结构体的制造方法、水泥类成形体的收缩减少方法和干燥抑制方法以及抑制劣化因子侵入水泥类结构体的方法 |
| WO2020167621A1 (en) | 2019-02-14 | 2020-08-20 | Sirrus, Inc. | Particles encapsulated with dicarbonyl-substituted-1- alkenes |
| EP3999607A2 (en) | 2019-07-19 | 2022-05-25 | Arkema France | Curable compositions useful for obtaining non-sensitizing cured products |
| US20230147645A1 (en) | 2019-10-18 | 2023-05-11 | Namics Corporation | Polymerizable composition and curable resin composition using same |
| CN110903194B (zh) * | 2019-12-11 | 2022-02-25 | 南京恒道医药科技有限公司 | 连续制备伏立康唑中间体2-氟-3-氧戊酸乙酯的方法 |
| CN111044647A (zh) * | 2019-12-20 | 2020-04-21 | 广电计量检测(合肥)有限公司 | 一种检测水体中直链烷基苯的样品前处理和定量分析方法 |
| WO2021150844A1 (en) | 2020-01-24 | 2021-07-29 | Sirrus, Inc. | Compositions containing 1,1-disubstituted activated alkenes useful in additive manufacturing and articles formed therefrom |
| WO2021162938A1 (en) | 2020-02-10 | 2021-08-19 | Sirrus, Inc. | Copolymers of dicarbonyl substituted-1-alkene and olefins and methods to make them |
| JP7656941B2 (ja) * | 2020-03-18 | 2025-04-04 | ナミックス株式会社 | 光硬化性樹脂組成物 |
| WO2021231288A1 (en) | 2020-05-15 | 2021-11-18 | Nippon Shokubai Co., Ltd. | Improved dicarbonyl substituted-1-alkene compositions |
| JP7462794B2 (ja) | 2020-06-11 | 2024-04-05 | 株式会社日本触媒 | 強酸および安定剤を含有する、1,1-ジエステル-1-アルケンから調製されたポリエステル |
| US20240140903A1 (en) * | 2020-12-17 | 2024-05-02 | The Royal Institution For The Advancement Of Learning / Mcgill University | Chemical additives and their use thereof for modifying mechanical properties of pvc and preventing the formation of surface defects during pvc calendering |
| TW202344592A (zh) * | 2022-02-07 | 2023-11-16 | 日商納美仕有限公司 | 液狀聚合性組成物及使用該聚合性組成物的硬化性樹脂組成物 |
| KR20240141242A (ko) | 2022-02-07 | 2024-09-26 | 나믹스 가부시끼가이샤 | 수지 조성물 및 이것을 사용한 경화성 수지 조성물 |
| EP4286677A1 (en) | 2022-06-02 | 2023-12-06 | Linde GmbH | Method of operating an internal combustion engine and corresponding arrangement |
Family Cites Families (275)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB432628A (en) | 1933-12-23 | 1935-07-23 | John David Kendall | Improvements in or relating to the production of compounds containing an ethylenic linkage, or a polymethine chain |
| US2277479A (en) | 1938-08-13 | 1942-03-24 | Gen Electric | Acetoacetic ester-formaldehyde resins |
| US2230033A (en) | 1939-01-04 | 1941-01-28 | James W Hackett | Foot exerciser |
| US2245567A (en) | 1939-06-23 | 1941-06-17 | Eastman Kodak Co | Manufacture of unsaturated ketones |
| US2313501A (en) | 1939-08-15 | 1943-03-09 | Eastman Kodak Co | Process for preparing methylene dialkyl malonates |
| US2212506A (en) | 1939-08-15 | 1940-08-27 | Eastman Kodak Co | Preparation of methylene dialkyl malonates |
| US2403791A (en) | 1939-11-16 | 1946-07-09 | Gen Electric | Interpolymers of a methylene malonic ester and an unsaturated alkyd resin |
| US2330033A (en) | 1939-11-16 | 1943-09-21 | Gen Electric | Method of preparing methylene malonic esters |
| US2569767A (en) * | 1946-05-27 | 1951-10-02 | L D Caulk Company | Dental material and method |
| US2730457A (en) | 1953-06-30 | 1956-01-10 | Ncr Co | Pressure responsive record materials |
| US3042710A (en) | 1960-10-03 | 1962-07-03 | Borden Co | Ethenoid carbonyl compounds |
| DE1569968B1 (de) | 1960-10-19 | 1969-11-06 | Eastman Kodak Co | Verwendung von hochgereinigten monomeren Estern der Methylenmalonsaeure als autopolymerisierbare Klebstoffe |
| US3197318A (en) | 1960-11-07 | 1965-07-27 | Borden Co | 2-methylenemalonic acid ester contact adhesive compositions |
| GB965767A (en) * | 1960-11-17 | 1964-08-06 | Hoyt Harrison Todd | Method of fusing materials to metal surfaces |
| FR1290837A (fr) | 1960-12-23 | 1962-04-20 | Air Liquide | Nouveaux polymères anthraquinoniques réducto-oxydables, leurs procédés de préparation et leur application à la fabrication de l'eau oxygénée |
| GB975733A (en) | 1961-12-18 | 1964-11-18 | Ici Ltd | Process for preventing haze formation in fermented beverages |
| US3203915A (en) | 1962-07-02 | 1965-08-31 | Dal Mon Research Co | Oxygen convertible polymeric compositions |
| US3221745A (en) | 1962-09-12 | 1965-12-07 | Eastman Kodak Co | Method of bonding body tissue together using methylenemalonic acid esters |
| US3427250A (en) | 1963-03-25 | 1969-02-11 | Polaroid Corp | Microscopic capsules and process for their preparation |
| US3489663A (en) | 1965-10-19 | 1970-01-13 | Owens Illinois Inc | Electrolytic polymerization |
| US3557185A (en) | 1967-03-06 | 1971-01-19 | Toa Gosei Chem Ind | Stabilized alpha-cyanoacrylate adhesive compositions |
| US4105688A (en) | 1968-05-09 | 1978-08-08 | Lonza, Ltd. | Process for the production of malonic acid dinitrile and purification thereof |
| US3595869A (en) | 1968-05-15 | 1971-07-27 | Merck & Co Inc | Process for preparing a diastereomer of an optically active ester or amide of (cis-1,2-epoxypropyl)-phosphonic acid |
| US3591676A (en) | 1968-11-01 | 1971-07-06 | Eastman Kodak Co | Surgical adhesive compositions |
| DE2027502C3 (de) | 1970-05-29 | 1980-06-19 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur Herstellung von Cyanacrylsäureestern |
| US3677989A (en) | 1970-06-16 | 1972-07-18 | Union Carbide Corp | Ethylene/acrylic acid copolymer emulsions |
| DE2042610C3 (de) | 1970-08-27 | 1979-03-15 | Wacker-Chemie Gmbh, 8000 Muenchen | Verfahren zur Herstellung von Methylenmalonester |
| US3940362A (en) | 1972-05-25 | 1976-02-24 | Johnson & Johnson | Cross-linked cyanoacrylate adhesive compositions |
| US3975422A (en) | 1972-11-21 | 1976-08-17 | Johnson & Johnson | Preparation of bis (2-cyanoacrylate)monomers |
| US3923836A (en) * | 1973-07-18 | 1975-12-02 | Smithkline Corp | Chroman and chromene compounds |
| US3973438A (en) | 1973-08-21 | 1976-08-10 | Westinghouse Electric Corporation | Composition for forming thermo-particulating coating which protects electrical apparatus |
| US4079058A (en) | 1973-08-29 | 1978-03-14 | Dynamit Nobel Ag | Process of performing cyclization reactions using benzyl or pyridylamino malonic acid derivatives |
| CH582655A5 (https=) | 1973-10-18 | 1976-12-15 | Lonza Ag | |
| US3945891A (en) | 1974-06-20 | 1976-03-23 | Fmc Corporation | Distillation process for purification of triaryl phosphate esters |
| US3966562A (en) | 1974-07-31 | 1976-06-29 | Agency Of Industrial Science & Technology | Multi-stage flash distillation plant |
| US4018656A (en) | 1974-09-03 | 1977-04-19 | Bechtel International Corporation | Thermal softening and distillation by regenerative method |
| US4004984A (en) | 1975-02-07 | 1977-01-25 | Aktiebolaget Atomenergi | Distillation plant |
| US4148693A (en) | 1975-02-26 | 1979-04-10 | Williamson William R | Horizontal cylindrical distillation apparatus |
| US3978422A (en) | 1975-02-28 | 1976-08-31 | Alpha Engineering Corporation | Broadband automatic gain control amplifier |
| US3995489A (en) | 1975-04-15 | 1976-12-07 | Westinghouse Electric Corporation | Malonic acid derivative composition for forming thermoparticulating coating |
| US4046943A (en) | 1975-04-15 | 1977-09-06 | Westinghouse Electric Corporation | Malonic acid derivative composition for forming thermoparticulating coating |
| SU614742A3 (ru) | 1975-06-02 | 1978-07-05 | Динамит Нобель Аг (Фирма) | Способ получени с - с диалкиловых эфиров малоновой кислоты |
| US4001345A (en) | 1975-06-02 | 1977-01-04 | Ppg Industries, Inc. | Distillation of methylchloroform |
| US4036985A (en) | 1975-07-16 | 1977-07-19 | Jose Amato | Mono substituted malonic acid diamides and process of preparing them |
| US4083751A (en) | 1975-08-11 | 1978-04-11 | Occidental Petroleum Corporation | Continuous feed pyrolysis chamber for decomposing solid waste |
| DE2661090C2 (https=) | 1975-11-07 | 1990-02-08 | Ciba-Geigy Ag, Basel, Ch | |
| US4319964A (en) | 1976-04-28 | 1982-03-16 | Jerome Katz | Apparatus for high volume distillation of liquids |
| US4035243A (en) | 1976-04-28 | 1977-07-12 | Jerome Katz | Method and apparatus for high volume distillation of liquids |
| US4282067A (en) | 1976-04-28 | 1981-08-04 | Jerome Katz | Apparatus for high volume distillation of liquids |
| US4186060A (en) | 1976-04-28 | 1980-01-29 | Fogel S J | Method and apparatus for high volume distillation of liquids |
| US4186058A (en) | 1976-04-28 | 1980-01-29 | Fogel S J | Method and apparatus for high volume distillation of liquids |
| US4154914A (en) | 1976-05-01 | 1979-05-15 | Toyo Seal Kogyo Kabushiki Kaisha (Toyo Seal Industries Co., Ltd.) | Process for producing acrylic rubber by copolymerizing acrylic ester and malonic acid derivative having active methylene group |
| US4229263A (en) | 1976-06-11 | 1980-10-21 | Phillips Petroleum Company | Recovery of methyl heptafluorobutyrate from methanol by distillation |
| US4236975A (en) | 1976-06-11 | 1980-12-02 | Phillips Petroleum Company | Recovery of methyl heptafluorobutyrate from water by distillation |
| US4224112A (en) | 1976-06-11 | 1980-09-23 | Phillips Petroleum Company | Recovery of 1,1-dihydroheptafluorobutanol from water by distillation |
| US4080238A (en) | 1976-07-14 | 1978-03-21 | Pratt & Lambert, Inc. | One-liquid cold setting adhesive with encapsulated catalyst initiator |
| US4049698A (en) | 1976-08-05 | 1977-09-20 | Eastman Kodak Company | Process for producing methylene malonic esters |
| US4118422A (en) | 1976-08-23 | 1978-10-03 | Texaco Development Corp. | Polyols from 2,3-morpholinediones |
| US4056543A (en) | 1976-09-07 | 1977-11-01 | Eastman Kodak Company | Process of preparing substituted acrylates |
| US4160864A (en) | 1976-09-07 | 1979-07-10 | Eastman Kodak Company | Adhesive compositions comprising methyl allyl methylenemalonate |
| US4282071A (en) | 1977-04-25 | 1981-08-04 | The Dow Chemical Company | Anhydrous separation of volatile aluminum chloride complex from an ethylbenzene production stream by distillation |
| EP0002260B1 (de) | 1977-12-02 | 1982-07-14 | Ciba-Geigy Ag | Malonsäurederivate von sterisch gehinderten Piperidinen, Verfahren zu ihrer Herstellung und mit ihnen stabilisiertes organisches Material |
| US4176012A (en) | 1978-01-10 | 1979-11-27 | Bryant Jeffrey J | Adjacent loop distillation |
| US4243493A (en) | 1978-02-03 | 1981-01-06 | Mannesmannrohren-Werke A.G. | Process for transportation and distillation of petroleum with methanol |
| US4256908A (en) | 1978-07-03 | 1981-03-17 | Ube Industries, Ltd. | Process for preparing diesters of malonic acid |
| JPS5647471A (en) | 1979-09-28 | 1981-04-30 | Japan Synthetic Rubber Co Ltd | Instantaneous adhesive composition |
| JPS5667383A (en) | 1979-11-08 | 1981-06-06 | Mitsui Petrochem Ind Ltd | Thixotropic agent |
| US4440601A (en) | 1980-01-28 | 1984-04-03 | Jerome Katz | Method and apparatus for high volume fractional distillation of liquids |
| US4291171A (en) | 1980-08-20 | 1981-09-22 | The United States Of America As Represented By The Secretary Of The Navy | Esters of 2-fluoro-2,2-dinitroethylmalonate and 2,2-dinitropropylmalonate |
| DE3105718A1 (de) | 1981-02-17 | 1982-09-02 | Hoechst Ag, 6000 Frankfurt | Fuer lebensmittel, insbesondere wurstwaren, geeignete rauchdurchlaessige schlauchhuelle mit einer klebenaht und verfahren zu ihrer herstellung |
| US4329479A (en) | 1981-04-07 | 1982-05-11 | Nihon Nohyaku Co., Ltd. | Process for producing 1,3-dithiol-2-ylidene malonic acid dialkyl esters |
| US4450067A (en) | 1981-04-30 | 1984-05-22 | Mobil Oil Corporation | Distillation-induced extraction process |
| US4897473A (en) | 1981-05-01 | 1990-01-30 | Union Carbide Chemicals And Plastics Company Inc. | Homologation of carbonyloxy containing compounds |
| US4444928A (en) | 1981-08-14 | 1984-04-24 | Ciba-Geigy Corporation | Polymeric malonic acid derivatives |
| JPS5867647A (ja) | 1981-10-15 | 1983-04-22 | Ube Ind Ltd | マロン酸ジエステルの製造法 |
| US4440910A (en) | 1982-01-18 | 1984-04-03 | Loctite Corporation | Toughened cyanoacrylates containing elastomeric rubbers |
| GB2115031B (en) | 1982-01-29 | 1985-09-18 | Andres Galvez Figari | Cast floors |
| JPS597193A (ja) | 1982-07-02 | 1984-01-14 | Shionogi & Co Ltd | マロニルメチル基の異性化方法 |
| EP0103233B1 (en) | 1982-08-31 | 1987-11-25 | Daikin Kogyo Co., Ltd. | A method to trap the enolate ion of the malonic acid or its derivatives |
| US4411740A (en) | 1982-09-20 | 1983-10-25 | Dow Corning Corporation | Separation of chlorosilanes by extractive distillation |
| DE3241512A1 (de) | 1982-11-10 | 1984-05-10 | Bayer Ag, 5090 Leverkusen | Substituierte malonsaeurediamide, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| FR2540739A1 (fr) | 1983-02-11 | 1984-08-17 | Elf France | Dispositif et installations pour la distillation par evaporation en couches minces, en particulier pour hydrocarbures, et procede de mise en oeuvre de ce dispositif |
| US4517105A (en) | 1983-03-07 | 1985-05-14 | Aluminum Company Of America | Metalworking lubricant composition containing a novel substituted malonic acid diester |
| AT379602B (de) * | 1983-07-11 | 1986-02-10 | Vianova Kunstharz Ag | Verfahren zur herstellung von vernetzungskomponenten fuer lackbindemittel |
| US4503074A (en) | 1983-08-08 | 1985-03-05 | Merck & Co., Inc. | Halogenated geminal diesters |
| US4767503A (en) | 1983-08-29 | 1988-08-30 | Allied Corporation | Removal of light impurities from caprolactam by distillation with water |
| US4728701A (en) * | 1983-09-19 | 1988-03-01 | Jarvis Marvin A | Process for the polymerization of acrylates |
| US4560723A (en) | 1983-11-14 | 1985-12-24 | Minnesota Mining And Manufacturing Company | Cyanoacrylate adhesive composition having sustained toughness |
| AT380008B (de) | 1983-12-23 | 1986-03-25 | Chemie Linz Ag | Verfahren zur herstellung von mono- oder biscarbonylverbindungen |
| DE3400401A1 (de) | 1984-01-07 | 1985-08-22 | Bayer Ag, 5090 Leverkusen | Substituierte malonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| US4720543A (en) | 1985-06-06 | 1988-01-19 | Georgetown University | 1a-7-substituted derivatives of mitomycin and uses thereof |
| US4613658A (en) | 1985-10-15 | 1986-09-23 | University Of Southern Mississippi | Vinyl monomers capable of forming side-chain liquid crystalline polymers and the resulting polymers |
| US4724053A (en) | 1985-12-20 | 1988-02-09 | Polaroid Corporation, Patent Dept. | Method for the electropolymerization of conductive polymers |
| CA1222845A (en) * | 1986-02-06 | 1987-06-09 | Progressive Chemical Research Ltd. | Silicone-sulfone and silicone-fluorocarbon-sulfone gas permeable contact lenses and compositions thereof |
| US5292937A (en) | 1986-03-31 | 1994-03-08 | Rhone-Poulenc Inc. | Use of malonic acid derivative compounds for retarding plant growth |
| JPS62260879A (ja) | 1986-05-07 | 1987-11-13 | Matsumoto Seiyaku Kogyo Kk | 接着剤組成物 |
| US4783242A (en) | 1986-05-22 | 1988-11-08 | The Dow Chemical Company | Distillation system and process |
| IT1196500B (it) | 1986-07-16 | 1988-11-16 | Eniricerche Spa | Derivati dell'acido malonico e metodi per la loro sintesi |
| JPS6342135A (ja) | 1986-08-08 | 1988-02-23 | Shinkawa Ltd | ワイヤボンデイング方法 |
| JPS63159385A (ja) | 1986-08-29 | 1988-07-02 | Nippon Nohyaku Co Ltd | マロン酸誘導体及びその製法並びにその用途 |
| US5446195A (en) | 1986-09-02 | 1995-08-29 | West Point Pepperell | Water-soluble active methylenes as formaldehyde scavengers |
| HU197574B (en) | 1986-10-09 | 1989-04-28 | Chinoin Gyogyszer Es Vegyeszet | Process for production of derivatives of 3,7-dihydro-3-methil-7-//1,2,4-oxadiasole/-3-il/alkylenil/-1h-purin-2,6-dion and medical compositions containing these substances |
| US4736056A (en) | 1986-12-15 | 1988-04-05 | Smith Oliver W | Process for the production of malonic acid derivative compounds |
| JPH087443B2 (ja) * | 1986-12-29 | 1996-01-29 | 凸版印刷株式会社 | 高解像度ポジ型放射線感応性レジスト |
| FR2611705B1 (fr) | 1987-03-05 | 1989-07-13 | Union Pharma Scient Appl | Procede de preparation de monesters ou diesters de l'acide endoethano-9, 10 dihydro-9, 10 anthracene bicarboxylique-11, 11, nouveaux monesters ou diesters ainsi prepares et utilisation de ceux-ci pour la preparation de methylenemalonates symetriques ou asymetriques |
| US4828882A (en) | 1987-03-16 | 1989-05-09 | Canadian Patents & Developments Limited | Particle encapsulation technique |
| DE3733552A1 (de) | 1987-10-03 | 1989-04-13 | Herberts Gmbh | Kathodisch abscheidbares waessriges elektrotauchlack-ueberzugsmittel und dessen verwendung |
| US5021486A (en) | 1989-03-21 | 1991-06-04 | Ciba-Geigy Corporation | Hindered amine-substituted malonic acid derivatives of s-triazine |
| JPH02281013A (ja) * | 1989-04-24 | 1990-11-16 | Cemedine Co Ltd | ジケトン化合物系共重合体 |
| DE3934190A1 (de) | 1989-10-13 | 1991-04-18 | Basf Ag | Malonsaeurefarbstoffe und deren polykondensationsprodukte |
| DE4009621A1 (de) | 1990-03-26 | 1991-10-02 | Henkel Kgaa | (alpha) -cyanacrylatklebstoffzusammensetzungen |
| US5284987A (en) | 1990-06-15 | 1994-02-08 | Amoco Corporation | Preparation of a dimethyltetralin in a distillation reactor |
| US5227027A (en) | 1990-08-23 | 1993-07-13 | Topper Robert T | High efficiency water distillation apparatus using a heat pump system and process for use thereof |
| US5064507A (en) | 1990-09-27 | 1991-11-12 | Allied-Signal Inc. | Distillation process for recovery of high purity phenol |
| MX9200216A (es) | 1991-01-21 | 1992-08-01 | Lonza Ag | Procedimiento para la preparacion de anhidrido de acido malonico. |
| DE4114733A1 (de) | 1991-05-06 | 1992-11-12 | Huels Chemische Werke Ag | Verfahren zur herstellung von substituierten malonesteraniliden und malonsaeure-monoaniliden |
| JPH0517723A (ja) | 1991-07-10 | 1993-01-26 | Three Bond Co Ltd | 接着剤組成物 |
| US5259835A (en) | 1991-08-29 | 1993-11-09 | Tri-Point Medical L.P. | Wound closure means and method using flowable adhesive |
| US5391624A (en) | 1992-02-10 | 1995-02-21 | S. C. Johnson & Son, Inc. | Thermosettable compositions |
| US5328687A (en) | 1993-03-31 | 1994-07-12 | Tri-Point Medical L.P. | Biocompatible monomer and polymer compositions |
| US5624669A (en) | 1993-03-31 | 1997-04-29 | Tri-Point Medical Corporation | Method of hemostatic sealing of blood vessels and internal organs |
| US5567761A (en) | 1993-05-10 | 1996-10-22 | Guertin Bros. Coatings And Sealants Ltd. | Aqueous two-part isocyanate-free curable, polyurethane resin systems |
| KR970010594B1 (ko) | 1993-10-16 | 1997-06-28 | 한국과학기술연구원 | 말론산 유도체의 백금착화합물 및 그 제조방법 |
| AU672337B2 (en) | 1993-10-27 | 1996-09-26 | Nippon Paint Co., Ltd. | Curable resin composition for coating uses |
| DE4408248A1 (de) | 1994-03-11 | 1995-09-14 | Hoechst Ag | Physiologisch verträgliche und physiologisch abbaubare Kohlenhydrat-Mimetika, ein Verfahren zur Herstellung und ihre Verwendung |
| EP0671409A3 (de) | 1994-03-11 | 1996-06-12 | Hoechst Ag | Malonsäurederivate mit antiadhäsiven Eigenschaften. |
| AU690303B2 (en) | 1994-06-28 | 1998-04-23 | Closure Medical Corporation | Ph-modified biocompatible monomer and polymer compositions |
| US5550172A (en) | 1995-02-07 | 1996-08-27 | Ethicon, Inc. | Utilization of biocompatible adhesive/sealant materials for securing surgical devices |
| DE19508049C2 (de) | 1995-02-23 | 1997-02-06 | Schering Ag | Verwendung von Methylenmalondiesterderivaten zur Herstellung von gasenthaltenden Mikropartikeln |
| JPH08231564A (ja) | 1995-02-28 | 1996-09-10 | Nippon Shokubai Co Ltd | リン酸エステルおよびその製造方法並びにリン酸エステル重合体 |
| US5614650A (en) | 1995-03-07 | 1997-03-25 | Sandler; Stanley R. | Zirconium compounds of sulfonic acids |
| US5928611A (en) | 1995-06-07 | 1999-07-27 | Closure Medical Corporation | Impregnated applicator tip |
| DE19541213A1 (de) | 1995-11-04 | 1997-05-07 | Rwe Dea Ag | Verfahren zur chemischen Umsetzung von Stoffen in einer Reaktionskolonne |
| JPH09258448A (ja) * | 1996-03-19 | 1997-10-03 | Fujitsu Ltd | レジスト組成物及びそれを用いた半導体装置製造方法 |
| EP0808822B1 (en) | 1996-05-22 | 2001-10-04 | Nippon Paint Co., Ltd. | Method for preparing malonate group-containing acrylate monomers |
| DE19623142A1 (de) | 1996-06-10 | 1997-12-11 | Huels Chemische Werke Ag | Enantiomerenangereicherte, durch einen tertiären Kohlenwasserstoffrest substituierte Malonsäuremonoester sowie deren Herstellung |
| DE19629372A1 (de) | 1996-07-20 | 1998-01-22 | Degussa | Verfahren zur Herstellung von Malonsäure oder einem Salz derselben |
| FR2755136B1 (fr) | 1996-10-25 | 1999-01-22 | Virsol | Procede de preparation de nanoparticules de methylidene malonate, nanoparticules contenant eventuellement une ou plusieurs molecules biologiquement actives et compositions pharmaceutiques les contenant |
| DE19704449A1 (de) | 1997-02-06 | 1998-08-13 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Malonsäure und Alkylmalonsäuren |
| WO1998037219A1 (en) | 1997-02-20 | 1998-08-27 | Mitsubishi Rayon Co., Ltd. | Process for producing malonic acid derivatives |
| DE19711762A1 (de) | 1997-03-21 | 1998-09-24 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Bishydroxymethylverbindungen |
| DE19724074C2 (de) | 1997-06-07 | 2000-01-13 | Metallgesellschaft Ag | Verfahren zur Hochtemperatur-Kurzzeit-Destillation von Rückstandsölen |
| WO1999001420A1 (en) | 1997-07-03 | 1999-01-14 | Taito Co., Ltd. | Process for the preparation of 2-aminomalonic acid derivatives and intermediates used in the process |
| EP1025587A4 (en) | 1997-07-21 | 2000-10-04 | Aguila Technologies Inc | SEMICONDUCTOR FLIPCHIP PACK AND PRODUCTION METHOD THEREFOR |
| BR9704357A (pt) | 1997-08-13 | 1999-05-11 | Trikem Sa | Processo para produção de acido malônico e de ésteres de acido malônico |
| US6353268B1 (en) | 1997-08-22 | 2002-03-05 | Micron Technology, Inc. | Semiconductor die attachment method and apparatus |
| FR2774096B1 (fr) | 1998-01-29 | 2000-04-07 | Virsol | Nouveaux copolymeres tensioactifs a base de methylidene malonate |
| US6291703B1 (en) | 1998-02-09 | 2001-09-18 | Ciba Specialty Chemicals Corporation | Preparation of substituted hydroxyhydrocinnamate esters by continuous transesterification using reactive distillation |
| FR2775284B1 (fr) * | 1998-02-20 | 2000-04-21 | Rhodia Chimie Sa | Procede de preparation de composes cetoniques aromatiques |
| WO1999046619A1 (en) | 1998-03-09 | 1999-09-16 | Corning Incorporated | Optical waveguide having non absorbing cladding region |
| FR2778100B1 (fr) | 1998-04-29 | 2001-05-04 | Virsol | Nouvelles microspheres a base de poly(methylidene malonate), leur procede de preparation et compositions pharmaceutiques les contenant |
| BR9910064A (pt) * | 1998-04-30 | 2000-12-26 | Closure Medical Corp | Processo para aplicar pelo menos um agente selecionado a partir do grupo que consiste de materiais bioativos, iniciadores de polimerização e modificadores de velocidade de polimerização em uma ponta de aplicador para adesivos, ponta de aplicador, e, aplicador para um adesivo polimerizável |
| US6512023B1 (en) | 1998-06-18 | 2003-01-28 | Closure Medical Corporation | Stabilized monomer adhesive compositions |
| JP2000019936A (ja) | 1998-07-06 | 2000-01-21 | Central Glass Co Ltd | ホログラムの作製方法およびその装置 |
| US6632518B1 (en) | 1998-10-14 | 2003-10-14 | E. I. Du Pont De Nemours And Company | Fluoropolymer film structures and laminates produced therefrom |
| KR20010093802A (ko) | 1998-12-07 | 2001-10-29 | 빌프리더 하이더 | 말론산 에스테르/트리아졸 혼합물로 차단된hdi삼량체/포름알데히드 안정화 |
| TR200101903T2 (tr) | 1999-01-02 | 2001-11-21 | Aventis Pharma Deutschland Gmbh | Yeni malonik asit türevleri, bunların preparasyon işlemleri. |
| JP2000199936A (ja) * | 1999-01-06 | 2000-07-18 | Konica Corp | 熱現像感光材料 |
| FR2788516B1 (fr) | 1999-01-14 | 2001-04-06 | Virsol | Procede de preparation de polymere de methylidene malonate |
| FR2789314B1 (fr) | 1999-02-09 | 2001-04-27 | Virsol | Materiau de suture de plaies a base de methylidene malonate |
| US6197482B1 (en) | 1999-05-14 | 2001-03-06 | Eastman Kodak Company | Polymer overcoat for imaging elements |
| EP1185356B1 (en) | 1999-05-27 | 2003-02-12 | Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno | Method for the purification of a liquid by membrane distillation, in particular for the production of desalinated water from seawater or brackish water or process water |
| US6210474B1 (en) | 1999-06-04 | 2001-04-03 | Eastman Kodak Company | Process for preparing an ink jet ink |
| US6225038B1 (en) | 1999-11-04 | 2001-05-01 | Eastman Kodak Company | Thermally processable imaging element |
| US6245933B1 (en) | 1999-11-19 | 2001-06-12 | Closure Medical Corporation | Transesterification method for making cyanoacrylates |
| DE19959587B4 (de) | 1999-12-10 | 2006-08-24 | Lurgi Lentjes Ag | Verfahren zur schonenden Kurzzeit-Destillation von Rückstandsölen |
| US6183593B1 (en) | 1999-12-23 | 2001-02-06 | Closure Medical Corporation | 1,1-disubstituted ethylene adhesive compositions containing polydimethylsiloxane |
| AUPQ540200A0 (en) | 2000-02-02 | 2000-02-24 | Aquadyne Incorporated | Water distillation systems |
| DE60104457T2 (de) | 2000-02-10 | 2005-08-04 | Nippon Shokubai Co., Ltd. | Verfahren zur Herstellung alpha, beta-ungesättigter Carbonsäureester sowie Katalysator zur Verwendung in diesem Verfahren |
| JP2003522753A (ja) | 2000-02-10 | 2003-07-29 | ロンザ ア−ゲ− | アルコキシマロン酸ジニトリルの製造方法 |
| EP1127884A1 (en) | 2000-02-26 | 2001-08-29 | Aventis Pharma Deutschland GmbH | Novel malonic acid derivatives, processes for their preparation, their use as inhibitor of factor XA activity and pharmaceutical compositions containing them |
| JP2004501270A (ja) | 2000-06-22 | 2004-01-15 | ザ ルブリゾル コーポレイション | 潤滑油および燃料のためのアシル化剤および分散剤 |
| US6753384B2 (en) | 2000-07-14 | 2004-06-22 | Metabolix, Inc. | Polyurethanes obtained from hydroxyalkanoates and isocyanates |
| US20040005314A1 (en) | 2001-07-27 | 2004-01-08 | Enrique Escandon | Apo-2l receptor agonist and cpt-11 synergism |
| FR2812551B1 (fr) | 2000-08-07 | 2003-03-28 | Virsol | Forme pharmaceutique comprenant un materiau support a base de methylidene malonate et un facteur de regulation cellulaire |
| ATE282650T1 (de) | 2000-10-17 | 2004-12-15 | Michelin Soc Tech | Verfahren zur herstellung eines dienelastomers durch anionische polymerisation |
| US6545097B2 (en) | 2000-12-12 | 2003-04-08 | Scimed Life Systems, Inc. | Drug delivery compositions and medical devices containing block copolymer |
| US20020151629A1 (en) | 2001-02-08 | 2002-10-17 | Buffkin Halbert C. | Protective coating |
| US7450290B2 (en) | 2001-06-25 | 2008-11-11 | University Of Washington | Electropolymerization of enhanced electrochromic (EC) polymer film |
| JP3976663B2 (ja) | 2001-11-01 | 2007-09-19 | 横浜ゴム株式会社 | 1液湿気硬化型ウレタン樹脂組成物 |
| US6896838B2 (en) | 2001-11-21 | 2005-05-24 | Closure Medical Corporation | Halogenated polymeric containers for 1, 1-disubstituted monomer compositions |
| US6767980B2 (en) | 2002-04-19 | 2004-07-27 | Nippon Shokubai Co., Ltd. | Reactive diluent and curable resin composition |
| US7002036B2 (en) | 2002-05-15 | 2006-02-21 | Genzyme Corporation | Synthesis of 2-alkyl amino acids |
| US7629416B2 (en) | 2002-08-12 | 2009-12-08 | Exxonmobil Chemical Patents Inc. | Plasticized polyolefin compositions |
| JP4694370B2 (ja) | 2002-10-18 | 2011-06-08 | 明治製菓株式会社 | マロン酸モノエステルおよびその製造方法 |
| US7056540B2 (en) | 2002-10-29 | 2006-06-06 | Council Of Scientific And Industrial Research | Enzymatic process for the preparation of optically active alcohols from ketones using tuberous root Daucus carota |
| US6826341B2 (en) | 2002-11-04 | 2004-11-30 | Fitel Usa Corp. | Systems and methods for reducing splice loss in optical fibers |
| KR101096993B1 (ko) | 2002-12-26 | 2011-12-20 | 이데미쓰 고산 가부시키가이샤 | 금속 가공용 수용성 윤활제, 그 사용에 적합한 금속 가공방법 및 금속 가공 장치 |
| DE10308504A1 (de) * | 2003-02-26 | 2004-09-09 | Basf Ag | Enzymatische Herstellung von (Meth)acrylsäureestern |
| EP1475367B1 (de) | 2003-05-08 | 2010-07-07 | Bayer MaterialScience AG | Verfahren zur Destillation eines Gemisches isomerer Diisocyanatodiphenylmethane |
| US6767857B1 (en) | 2003-05-29 | 2004-07-27 | Fina Technology, Inc. | Process for forming a Ziegler-Natta catalyst system having a controlled morphology |
| GB0317268D0 (en) | 2003-07-23 | 2003-08-27 | Viral Asa A | Compounds |
| WO2005012427A1 (ja) | 2003-08-04 | 2005-02-10 | Zeon Corporation | 重合性組成物及びそれを用いてなる成形体 |
| US7226957B1 (en) | 2003-11-03 | 2007-06-05 | University Of Iowa Research Foundation | Method for producing polymers with controlled molecular weight and end group functionality using photopolymerization in microemulsions |
| JP2005170803A (ja) | 2003-12-08 | 2005-06-30 | Daicel Chem Ind Ltd | 新規なマロン酸モノメチル誘導体とその製造法 |
| US20050228074A1 (en) | 2004-04-05 | 2005-10-13 | Bridgestone Corporation | Amphiphilic polymer micelles and use thereof |
| US7170188B2 (en) | 2004-06-30 | 2007-01-30 | Intel Corporation | Package stress management |
| CA2574113C (en) | 2004-07-23 | 2014-02-18 | Anna Lee Tonkovich | Distillation process using microchannel technology |
| US7305850B2 (en) | 2004-07-23 | 2007-12-11 | Velocys, Inc. | Distillation process using microchannel technology |
| EP1784302B1 (en) | 2004-09-01 | 2016-07-06 | Encapsys, Llc | Encapsulated cure systems |
| US9598527B2 (en) | 2004-09-01 | 2017-03-21 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
| US7371804B2 (en) | 2004-09-07 | 2008-05-13 | Ophthonix, Inc. | Monomers and polymers for optical elements |
| US8075906B2 (en) | 2005-02-01 | 2011-12-13 | Boston Scientific Scimed, Inc. | Medical devices having polymeric regions with copolymers containing hydrocarbon and heteroatom-containing monomeric species |
| WO2006107900A2 (en) | 2005-04-01 | 2006-10-12 | Visyx Technologies, Inc. | Monitoring by means of an on-line sensor and fluidic operations involving unit separation and reaction operations |
| WO2007018736A2 (en) | 2005-07-22 | 2007-02-15 | Appleton Papers Inc. | Encapsulated structural adhesive |
| US7919543B2 (en) | 2005-08-16 | 2011-04-05 | Electronics For Imaging, Inc. | Inkjet inks, methods for applying inkjet ink, and articles printed with inkjet inks |
| DE602006012593D1 (de) | 2005-08-24 | 2010-04-15 | Nippon Catalytic Chem Ind | Durch Radiation vernetzbare Zusammensetzungen und daraus hergestelte vernetzte Produkte |
| US7771567B2 (en) | 2005-09-02 | 2010-08-10 | Rives Michael L | Salt water distillation system |
| US20070092483A1 (en) | 2005-10-21 | 2007-04-26 | Pollock Polymer Group | Surgical adhesive compostion and process for enhanced tissue closure and healing |
| US7626477B2 (en) | 2005-11-28 | 2009-12-01 | General Electric Company | Cold mass cryogenic cooling circuit inlet path avoidance of direct conductive thermal engagement with substantially conductive coupler for superconducting magnet |
| WO2007069746A1 (ja) | 2005-12-16 | 2007-06-21 | Yoshihiro Watanabe | サーフボード等物品及びその製造方法 |
| EP2348027B1 (en) | 2006-04-07 | 2013-10-23 | E. I. du Pont de Nemours and Company | Lipochitooligosaccharides |
| WO2007120630A2 (en) | 2006-04-10 | 2007-10-25 | Abm Associates Llc | Activated anaerobic adhesive and use thereof |
| US7659423B1 (en) * | 2006-04-18 | 2010-02-09 | Loctite (R&D) Limited | Method of preparing electron deficient olefins in polar solvents |
| JP5435942B2 (ja) | 2006-05-29 | 2014-03-05 | 電気化学工業株式会社 | クロス共重合体の製造方法、得られるクロス共重合体、及びその用途 |
| ES2401803T3 (es) | 2006-08-16 | 2013-04-24 | Asahi Kasei Chemicals Corporation | Procedimiento para producir copolímero de bloques, y copolímero de bloques o producto hidrogenado del mismo |
| US8332435B2 (en) | 2006-10-03 | 2012-12-11 | Salesforce.Com, Inc. | Method and system for customizing a user interface to an on-demand database service |
| FR2907131B1 (fr) | 2006-10-12 | 2008-11-21 | Commissariat Energie Atomique | Procede de formation de films organiques sur des surfaces conductrices ou semi-conductrices de l'electricite a partir de solutions aqueuses en deux etapes |
| ATE425876T1 (de) | 2006-11-30 | 2009-04-15 | Fujifilm Corp | Tintenzusammensetzung zur tintenstrahlaufzeichnung und verfahren zur tintenstrahlaufzeichnung |
| JP2008174494A (ja) | 2007-01-19 | 2008-07-31 | Nippon Shokubai Co Ltd | メチレンマロン酸組成物およびその安定化方法 |
| JP2008189776A (ja) | 2007-02-02 | 2008-08-21 | Fujifilm Corp | 活性放射線硬化型重合性組成物、インク組成物、インクジェット記録方法、印刷物、平版印刷版の作製方法、及び平版印刷版 |
| WO2008098011A1 (en) | 2007-02-06 | 2008-08-14 | Glumetrics, Inc. | Method for polymerizing a monomer solution within a cavity to generate a smooth polymer surface |
| JP5243072B2 (ja) | 2007-03-30 | 2013-07-24 | 富士フイルム株式会社 | インク組成物、並びに、それを用いた画像記録方法及び画像記録物 |
| US8168213B2 (en) | 2007-05-15 | 2012-05-01 | Boston Scientific Scimed, Inc. | Medical devices having coating with improved adhesion |
| US7742670B2 (en) | 2007-10-01 | 2010-06-22 | Corning Cable Systems Llc | Index-matching gel for nanostructure optical fibers and mechanical splice assembly and connector using same |
| KR20090064862A (ko) | 2007-12-17 | 2009-06-22 | 광주과학기술원 | 피리딘을 기능성 그룹으로 함유한 스티렌 유도체의 음이온중합 방법 |
| US8138610B2 (en) | 2008-02-08 | 2012-03-20 | Qimonda Ag | Multi-chip package with interconnected stacked chips |
| JP2009192309A (ja) | 2008-02-13 | 2009-08-27 | Shinko Electric Ind Co Ltd | 半導体検査装置 |
| BRPI0908991A2 (pt) | 2008-03-18 | 2015-10-13 | Mitsui Chemicals Agro Inc | método para produzir derivado de ácido acilacético contendo flúor, método para produzir derivado de éster de ácido pirazolcarboxílico contendo flúor e método para produzir derivado de ácido pirazolcarboxílixo contendo flúor |
| KR101215459B1 (ko) | 2008-03-27 | 2012-12-26 | 도쿄 프린팅 잉크 엠에프지. 캄파니 리미티드 | 에칭 레지스트용 잉크젯 잉크 조성물 |
| US8318060B2 (en) | 2008-07-22 | 2012-11-27 | University Of New Hampshire | Microencapsulation of amines |
| GB2463065B (en) * | 2008-09-01 | 2012-11-07 | Loctite R & D Ltd | Transferable curable non-liquid film on a release substrate |
| EP2344207B1 (en) | 2008-09-22 | 2013-12-25 | Boston Scientific Neuromodulation Corporation | Implantable or insertable medical devices |
| DE102009000861A1 (de) | 2009-02-13 | 2010-08-19 | Henkel Ag & Co. Kgaa | Verfahren zur Herstellung von Cyanacrylsäureestern |
| US8975435B2 (en) * | 2009-05-07 | 2015-03-10 | Optmed, Inc. | Methylidene malonate process |
| US8106234B2 (en) | 2009-05-07 | 2012-01-31 | OptMed, Inc | Methylidene malonate process |
| US7829738B1 (en) | 2009-05-19 | 2010-11-09 | Nalco Company | Production of N,N-dialklylaminoethyl (meth)acrylates |
| EP2436702B1 (en) | 2009-05-29 | 2014-12-17 | JX Nippon Oil & Energy Corporation | Isobutylene-based polymer and method for producing same |
| DE102009027545A1 (de) | 2009-07-08 | 2011-02-03 | Henkel Ag & Co. Kgaa | Verfahren zur Herstellung von Cyanacrylsäureestern in Gegenwart von Übergangsmetall-Katalysatoren |
| JP5671302B2 (ja) * | 2009-11-10 | 2015-02-18 | 富士フイルム株式会社 | インプリント用硬化性組成物、パターン形成方法およびパターン |
| JPWO2011070739A1 (ja) | 2009-12-07 | 2013-04-22 | 住友ベークライト株式会社 | 半導体封止用エポキシ樹脂組成物、その硬化体及び半導体装置 |
| JP2011122005A (ja) * | 2009-12-08 | 2011-06-23 | Sony Corp | 反射防止フィルム及びその製造方法、並びに紫外線硬化性樹脂材料組成物塗液 |
| AU2011233663B2 (en) | 2010-04-03 | 2016-04-14 | Praful Doshi | Medical devices including medicaments and methods of making and using same |
| MY155680A (en) | 2010-06-23 | 2015-11-13 | Total Res & Technology | Dehydration of alcohols on poisoned acidic catalysts |
| US8554938B2 (en) | 2010-08-31 | 2013-10-08 | Millind Mittal | Web browser proxy-client video system and method |
| US9249265B1 (en) | 2014-09-08 | 2016-02-02 | Sirrus, Inc. | Emulsion polymers including one or more 1,1-disubstituted alkene compounds, emulsion methods, and polymer compositions |
| SG189933A1 (en) | 2010-10-20 | 2013-06-28 | Bioformix Llc | Synthesis of methylene malonates substantially free of impurities |
| EP2655509B1 (en) | 2010-12-20 | 2014-11-19 | DSM IP Assets B.V. | Aqueous bio-renewable vinyl polymer composition |
| US20130019520A1 (en) | 2011-02-02 | 2013-01-24 | Brown University | Methods of Making Fatty Acids and Fatty Acid Alkyl Esters |
| CN102901754A (zh) | 2011-07-27 | 2013-01-30 | 中国科学院电子学研究所 | 基于电聚合分子印迹技术的双参数复合微传感器及制备法 |
| EP3517523A1 (en) * | 2011-10-19 | 2019-07-31 | Sirrus, Inc. | Multifunctional monomers and methods for making them |
| EP2831124B1 (en) | 2012-03-30 | 2016-10-05 | Sirrus, Inc. | Composite and laminate articles and polymerizable systems for producing the same |
| JP6188252B2 (ja) | 2012-03-30 | 2017-08-30 | シラス・インコーポレイテッド | 重合性組成物の活性化方法、重合系およびこれにより形成される製品 |
| CA2869115A1 (en) | 2012-03-30 | 2013-10-03 | Bioformix Inc. | Ink and coating formulations and polymerizable systems for producing the same |
| US10047192B2 (en) | 2012-06-01 | 2018-08-14 | Sirrus, Inc. | Optical material and articles formed therefrom |
| US9139792B2 (en) | 2012-06-04 | 2015-09-22 | Biosynthetic Technologies, Llc | Processes of preparing estolide base oils and lubricants that include transesterification |
| JP6475627B2 (ja) | 2012-10-19 | 2019-02-27 | コロラド ステート ユニバーシティー リサーチ ファウンデーション | 電極材料上へのコーティングの電解重合 |
| WO2014078689A1 (en) | 2012-11-16 | 2014-05-22 | Bioformix Inc. | Plastics bonding systems and methods |
| EP2926368B1 (en) | 2012-11-30 | 2020-04-08 | Sirrus, Inc. | Electronic assembly |
| CN105008321A (zh) | 2013-01-11 | 2015-10-28 | 瑟拉斯公司 | 经过双(羟甲基)丙二酸酯的途径获得亚甲基丙二酸酯的方法 |
| US9334430B1 (en) | 2015-05-29 | 2016-05-10 | Sirrus, Inc. | Encapsulated polymerization initiators, polymerization systems and methods using the same |
| US9217098B1 (en) | 2015-06-01 | 2015-12-22 | Sirrus, Inc. | Electroinitiated polymerization of compositions having a 1,1-disubstituted alkene compound |
| DE102017204525A1 (de) | 2016-03-23 | 2017-09-28 | Basf Se | Verbundfolienlaminate für flexible Verpackungen |
| US11015034B2 (en) | 2016-04-21 | 2021-05-25 | Zephyros, Inc. | Malonates and derivatives for in-situ films |
| US20180010014A1 (en) | 2016-07-11 | 2018-01-11 | Zephyros, Inc. | Compositions for adhesive applications |
| CN109475903B (zh) | 2016-07-26 | 2021-11-26 | Ppg工业俄亥俄公司 | 含有1,1-二活化的乙烯基化合物产物的多层可固化组合物及相关工艺 |
| ES2957658T3 (es) | 2016-07-26 | 2024-01-23 | Ppg Ind Ohio Inc | Composiciones de recubrimiento de poliuretano que contienen compuestos vinílicos 1,1-diactivados y recubrimientos y procesos relacionados |
| JP7498561B2 (ja) | 2016-07-26 | 2024-06-12 | ピーピージー・インダストリーズ・オハイオ・インコーポレイテッド | 1,1-二活性化ビニル化合物を含有する硬化性組成物ならびに関連のコーティングおよび方法 |
| US11136469B2 (en) | 2016-07-26 | 2021-10-05 | Ppg Industries Ohio, Inc. | Acid-catalyzed curable coating compositions containing 1,1-di-activated vinyl compounds and related coatings and processes |
| CN109642098B (zh) | 2016-07-26 | 2022-02-11 | Ppg工业俄亥俄公司 | 包含1,1-二活化的乙烯基化合物的可电沉积的涂料组合物 |
| WO2018022794A1 (en) | 2016-07-26 | 2018-02-01 | Ppg Industries Ohio, Inc. | Particles having surfaces functionalized with 1,1-di-activated vinyl compounds |
| CN109476081B (zh) | 2016-07-26 | 2021-11-23 | Ppg工业俄亥俄公司 | 使用1,1-二活化的乙烯基化合物的三维印刷方法 |
| CN109844036A (zh) | 2016-09-19 | 2019-06-04 | 泽菲罗斯有限公司 | 聚丙二酸酯和氰基丙烯酸酯基混凝土表面密封剂 |
| EP3515973B1 (en) | 2016-09-19 | 2025-10-29 | Zephyros Inc. | Malonate and cyanoacrylate adhesives for joining dissimilar materials |
| CN109952330B (zh) | 2016-11-09 | 2021-07-02 | 巴斯夫欧洲公司 | 聚氨酯-乙烯基混杂聚合物、其制法和它们的用途 |
-
2012
- 2012-10-18 EP EP18203773.9A patent/EP3517523A1/en not_active Withdrawn
- 2012-10-18 US US14/352,369 patent/US9221739B2/en not_active Expired - Fee Related
- 2012-10-18 EP EP18152189.9A patent/EP3339301A3/en not_active Withdrawn
- 2012-10-18 MX MX2014004782A patent/MX360462B/es active IP Right Grant
- 2012-10-18 MX MX2014004781A patent/MX360463B/es active IP Right Grant
- 2012-10-18 WO PCT/US2012/060830 patent/WO2013059473A2/en not_active Ceased
- 2012-10-18 EP EP12842316.7A patent/EP2768917B1/en not_active Not-in-force
- 2012-10-18 US US14/352,406 patent/US9527795B2/en not_active Expired - Fee Related
- 2012-10-18 JP JP2014537249A patent/JP2014534969A/ja active Pending
- 2012-10-18 EP EP12846728.9A patent/EP2768872B1/en not_active Not-in-force
- 2012-10-18 WO PCT/US2012/060840 patent/WO2013059479A2/en not_active Ceased
- 2012-10-18 CA CA2853068A patent/CA2853068A1/en not_active Abandoned
- 2012-10-18 CA CA2853073A patent/CA2853073A1/en not_active Abandoned
- 2012-10-18 US US14/352,356 patent/US9512058B2/en not_active Expired - Fee Related
- 2012-10-18 EP EP17190852.8A patent/EP3293216A1/en not_active Withdrawn
- 2012-10-18 JP JP2014537250A patent/JP2014532625A/ja active Pending
- 2012-10-18 CA CA2853079A patent/CA2853079A1/en not_active Abandoned
- 2012-10-18 JP JP2014537248A patent/JP6267643B2/ja active Active
- 2012-10-18 WO PCT/US2012/060837 patent/WO2013066629A1/en not_active Ceased
- 2012-10-18 MX MX2014004780A patent/MX370256B/es active IP Right Grant
- 2012-10-18 EP EP12842121.1A patent/EP2768897B1/en not_active Not-in-force
-
2016
- 2016-10-10 US US15/289,300 patent/US9969822B2/en not_active Expired - Fee Related
- 2016-11-29 US US15/363,169 patent/US20170073438A1/en not_active Abandoned
-
2018
- 2018-05-14 US US15/978,974 patent/US10604601B2/en not_active Expired - Fee Related
- 2018-05-14 US US15/978,923 patent/US10611861B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10604601B2 (en) | Multifunctional monomers, methods for making multifunctional monomers, polymerizable compositions and products formed therefrom | |
| EP2630116B1 (en) | Synthesis of methylene malonates using rapid recovery in the presence of a heat transfer agent | |
| US9828324B2 (en) | Methylene beta-diketone monomers, methods for making methylene beta-diketone monomers, polymerizable compositions and products formed therefrom | |
| US10414839B2 (en) | Polymers including a methylene beta-ketoester and products formed therefrom | |
| US20090076201A1 (en) | (meth) acryloyloxytetrahydrofurans and process for production thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20161019 |