BE373692A

BE373692A -

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Publication number: BE373692A
Authority: BE; Belgium
Prior art keywords: esters; resins; ester; acid; keto
Prior art date

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English (en)

French (fr)

Publication of BE373692A publication Critical patent/BE373692A/fr

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150000002148 esters Chemical class 0.000 claims description 39
239000000203 mixture Substances 0.000 claims description 31
239000011347 resin Substances 0.000 claims description 27
229920005989 resin Polymers 0.000 claims description 27
239000004014 plasticizer Substances 0.000 claims description 26
239000004033 plastic Substances 0.000 claims description 21
-1 phenol aldehyde Chemical class 0.000 claims description 20
150000004715 keto acids Chemical class 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 7
150000001298 alcohols Chemical class 0.000 claims description 6
238000009833 condensation Methods 0.000 claims description 5
230000005494 condensation Effects 0.000 claims description 5
239000000025 natural resin Substances 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 4
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
238000005727 Friedel-Crafts reaction Methods 0.000 claims description 3
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
150000002170 ethers Chemical class 0.000 claims description 3
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
150000007519 polyprotic acids Polymers 0.000 claims description 3
229920001807 Urea-formaldehyde Polymers 0.000 claims description 2
ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 claims description 2
239000008199 coating composition Substances 0.000 claims 1
229920001169 thermoplastic Polymers 0.000 claims 1
239000004416 thermosoftening plastic Substances 0.000 claims 1
239000000047 product Substances 0.000 description 19
239000004922 lacquer Substances 0.000 description 13
238000009835 boiling Methods 0.000 description 12
150000007513 acids Chemical class 0.000 description 9
230000008018 melting Effects 0.000 description 8
238000002844 melting Methods 0.000 description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
NQSMEZJWJJVYOI-UHFFFAOYSA-N Methyl 2-benzoylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 NQSMEZJWJJVYOI-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000007787 solid Substances 0.000 description 6
VMHKPGQWBDCKSM-UHFFFAOYSA-N butyl 2-benzoylbenzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 VMHKPGQWBDCKSM-UHFFFAOYSA-N 0.000 description 5
239000007859 condensation product Substances 0.000 description 5
239000000945 filler Substances 0.000 description 5
239000007788 liquid Substances 0.000 description 5
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
239000000020 Nitrocellulose Substances 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 3
QICBFAHTUHBDFV-UHFFFAOYSA-N benzoyl naphthalene-1-carboxylate Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)OC(=O)C1=CC=CC=C1 QICBFAHTUHBDFV-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
239000011976 maleic acid Substances 0.000 description 3
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
229920001220 nitrocellulos Polymers 0.000 description 3
229920003002 synthetic resin Polymers 0.000 description 3
239000000057 synthetic resin Substances 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000004859 Copal Substances 0.000 description 2
229920002871 Dammar gum Polymers 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000782205 Guibourtia conjugata Species 0.000 description 2
101150100348 Icmt gene Proteins 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
229920001800 Shellac Polymers 0.000 description 2
239000004902 Softening Agent Substances 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000003513 alkali Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 2
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
QEUKMSHPJKCCPM-UHFFFAOYSA-N butyl 2-(naphthalene-1-carbonyl)benzoate Chemical compound C1(=CC=CC2=CC=CC=C12)C(=O)C1=C(C(=O)OCCCC)C=CC=C1 QEUKMSHPJKCCPM-UHFFFAOYSA-N 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
229920003086 cellulose ether Polymers 0.000 description 2
238000004040 coloring Methods 0.000 description 2
210000003298 dental enamel Anatomy 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
239000012530 fluid Substances 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
YFIROWGKGBPJJJ-UHFFFAOYSA-N methyl 2-(naphthalene-1-carbonyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1C(=O)C1=CC=CC2=CC=CC=C12 YFIROWGKGBPJJJ-UHFFFAOYSA-N 0.000 description 2
229940107390 pentasol Drugs 0.000 description 2
125000005498 phthalate group Chemical class 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 2
239000004208 shellac Substances 0.000 description 2
229940113147 shellac Drugs 0.000 description 2
235000013874 shellac Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 description 1
UPBNKJAWOLRKED-UHFFFAOYSA-N 2-(1,2-dihydroacenaphthylene-1-carbonyl)benzoic acid Chemical compound C1(CC2=CC=CC3=CC=CC1=C23)C(=O)C2=C(C(=O)O)C=CC=C2 UPBNKJAWOLRKED-UHFFFAOYSA-N 0.000 description 1
OXCYAVHGYGKEJY-UHFFFAOYSA-N 2-(naphthalene-1-carbonyl)benzoic acid Chemical class OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC2=CC=CC=C12 OXCYAVHGYGKEJY-UHFFFAOYSA-N 0.000 description 1
FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 1
WWROZRYLEDOUCU-UHFFFAOYSA-N 3-methoxy-3-phenyl-2-benzofuran-1-one Chemical group O1C(=O)C2=CC=CC=C2C1(OC)C1=CC=CC=C1 WWROZRYLEDOUCU-UHFFFAOYSA-N 0.000 description 1
CDUACMUYDHRMBX-UHFFFAOYSA-N 6-(oxomethylidene)cyclohexa-2,4-diene-1-carboxylic acid Chemical compound OC(=O)C1C=CC=CC1=C=O CDUACMUYDHRMBX-UHFFFAOYSA-N 0.000 description 1
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
102000011632 Caseins Human genes 0.000 description 1
108010076119 Caseins Proteins 0.000 description 1
239000004860 Dammar gum Substances 0.000 description 1
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
BZEAVYMPEGEFBF-UHFFFAOYSA-N benzyl 2-benzoylbenzoate Chemical class C=1C=CC=C(C(=O)C=2C=CC=CC=2)C=1C(=O)OCC1=CC=CC=C1 BZEAVYMPEGEFBF-UHFFFAOYSA-N 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
229940021722 caseins Drugs 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000002131 composite material Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
230000007423 decrease Effects 0.000 description 1
229960002380 dibutyl phthalate Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
230000004927 fusion Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
238000004898 kneading Methods 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002184 metal Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
BPGWKEYVGLYUCQ-UHFFFAOYSA-N methyl 2-benzoyl-3-chlorobenzoate Chemical compound ClC=1C(=C(C(=O)OC)C=CC=1)C(C1=CC=CC=C1)=O BPGWKEYVGLYUCQ-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
238000000465 moulding Methods 0.000 description 1
239000003345 natural gas Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
YKDSLQJDCADCTM-UHFFFAOYSA-N pentyl 2-benzoylbenzoate Chemical class C(C1=CC=CC=C1)(=O)C1=C(C(=O)OCCCCC)C=CC=C1 YKDSLQJDCADCTM-UHFFFAOYSA-N 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
ZDCHZHDOCCIZIY-UHFFFAOYSA-N phthalic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OC(=O)C1=CC=CC=C1C(O)=O ZDCHZHDOCCIZIY-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1