DK2831055T3 - POLYMERIZABLE ALKYLIDE-1,3-DIOXOLAN-2-ONES AND THEIR USE - Google Patents

Info

Publication number

DK2831055T3

DK2831055T3 DK13713176.9T DK13713176T DK2831055T3 DK 2831055 T3 DK2831055 T3 DK 2831055T3 DK 13713176 T DK13713176 T DK 13713176T DK 2831055 T3 DK2831055 T3 DK 2831055T3

Authority

DK

Denmark

Prior art keywords

alkyl

groups

compounds

formula

monoethylenically unsaturated

Prior art date

2012-03-29

Links

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• 239000000203 mixture Substances 0.000 claims description 97
• 229920000642 polymer Polymers 0.000 claims description 75
• 150000001875 compounds Chemical class 0.000 claims description 68
• 239000000178 monomer Substances 0.000 claims description 61
• -1 ethanediyl Chemical group 0.000 claims description 59
• 238000006243 chemical reaction Methods 0.000 claims description 36
• 125000001931 aliphatic group Chemical group 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 29
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
• 150000002148 esters Chemical class 0.000 claims description 25
• 238000000034 method Methods 0.000 claims description 25
• 239000011230 binding agent Substances 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• 238000002360 preparation method Methods 0.000 claims description 19
• 238000005809 transesterification reaction Methods 0.000 claims description 17
• 239000000126 substance Substances 0.000 claims description 16
• 230000032050 esterification Effects 0.000 claims description 15
• 238000005886 esterification reaction Methods 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000000524 functional group Chemical group 0.000 claims description 13
• 230000008569 process Effects 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 9
• XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
• 229920001519 homopolymer Polymers 0.000 claims description 7
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 5
• 150000001336 alkenes Chemical class 0.000 claims description 5
• 150000001991 dicarboxylic acids Chemical class 0.000 claims description 5
• 150000003839 salts Chemical class 0.000 claims description 5
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 4
• 239000000470 constituent Substances 0.000 claims description 4
• 150000002763 monocarboxylic acids Chemical class 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 125000005907 alkyl ester group Chemical group 0.000 claims description 3
• 125000005587 carbonate group Chemical group 0.000 claims description 3
• 230000000269 nucleophilic effect Effects 0.000 claims description 3
• 229920002554 vinyl polymer Polymers 0.000 claims description 3
• UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims description 2
• 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims description 2
• 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
• 125000003700 epoxy group Chemical group 0.000 claims description 2
• 150000002825 nitriles Chemical class 0.000 claims description 2
• 150000003460 sulfonic acids Chemical class 0.000 claims description 2
• 229920001567 vinyl ester resin Polymers 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 125000002947 alkylene group Chemical group 0.000 claims 1
• 239000004848 polyfunctional curative Substances 0.000 description 46
• DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 44
• 238000006116 polymerization reaction Methods 0.000 description 37
• 239000002904 solvent Substances 0.000 description 36
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
• GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 32
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 31
• 239000003054 catalyst Substances 0.000 description 30
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 28
• 239000007787 solid Substances 0.000 description 23
• 150000001412 amines Chemical class 0.000 description 22
• 229920005862 polyol Polymers 0.000 description 20
• 150000003077 polyols Chemical class 0.000 description 20
• 239000011541 reaction mixture Substances 0.000 description 20
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
• 229920001577 copolymer Polymers 0.000 description 17
• 238000005227 gel permeation chromatography Methods 0.000 description 17
• 238000007334 copolymerization reaction Methods 0.000 description 16
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 14
• KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical group O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 14
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 14
• BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 14
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
• 238000004458 analytical method Methods 0.000 description 14
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• 239000011572 manganese Substances 0.000 description 12
• 229920000768 polyamine Polymers 0.000 description 12
• FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 11
• 125000000217 alkyl group Chemical group 0.000 description 11
• 229920001451 polypropylene glycol Polymers 0.000 description 11
• 230000001476 alcoholic effect Effects 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 10
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
• DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 9
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
• 150000001298 alcohols Chemical group 0.000 description 9
• CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 9
• 239000003085 diluting agent Substances 0.000 description 9
• IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 9
• 229930195733 hydrocarbon Natural products 0.000 description 9
• 150000002430 hydrocarbons Chemical class 0.000 description 9
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
• 229910052757 nitrogen Inorganic materials 0.000 description 9
• 239000003960 organic solvent Substances 0.000 description 9
• 229920005906 polyester polyol Polymers 0.000 description 9
• ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 8
• 108090000790 Enzymes Proteins 0.000 description 8
• 102000004190 Enzymes Human genes 0.000 description 8
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
• 239000000853 adhesive Substances 0.000 description 8
• 230000001070 adhesive effect Effects 0.000 description 8
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
• 238000004132 cross linking Methods 0.000 description 8
• NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 8
• 238000004519 manufacturing process Methods 0.000 description 8
• QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 150000002596 lactones Chemical class 0.000 description 7
• 239000003505 polymerization initiator Substances 0.000 description 7
• 239000000376 reactant Substances 0.000 description 7
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• 239000002202 Polyethylene glycol Substances 0.000 description 6
• 238000005576 amination reaction Methods 0.000 description 6
• WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
• 238000000576 coating method Methods 0.000 description 6
• 150000004985 diamines Chemical class 0.000 description 6
• 238000004817 gas chromatography Methods 0.000 description 6
• 239000012948 isocyanate Substances 0.000 description 6
• 239000000463 material Substances 0.000 description 6
• NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
• 229920000570 polyether Polymers 0.000 description 6
• 229920001223 polyethylene glycol Polymers 0.000 description 6
• 125000006239 protecting group Chemical group 0.000 description 6
• 239000007921 spray Substances 0.000 description 6
• HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 5
• YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 5
• RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 5
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
• 108090001060 Lipase Proteins 0.000 description 5
• 239000004367 Lipase Substances 0.000 description 5
• 102000004882 Lipase Human genes 0.000 description 5
• VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
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• GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
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• 230000015572 biosynthetic process Effects 0.000 description 5
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• 150000005690 diesters Chemical class 0.000 description 5
• 150000002009 diols Chemical class 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 238000010528 free radical solution polymerization reaction Methods 0.000 description 5
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• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
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• SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 3
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