CH426256A - Procédé d'obtention rapide de plaques translucides ou transparentes - Google Patents
Procédé d'obtention rapide de plaques translucides ou transparentesInfo
- Publication number
- CH426256A CH426256A CH1238563A CH1238563A CH426256A CH 426256 A CH426256 A CH 426256A CH 1238563 A CH1238563 A CH 1238563A CH 1238563 A CH1238563 A CH 1238563A CH 426256 A CH426256 A CH 426256A
- Authority
- CH
- Switzerland
- Prior art keywords
- phosphate
- halogenated
- phthalate
- weight
- polycondensate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 halogenated aryl phosphate Chemical compound 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 22
- 229920001225 polyester resin Polymers 0.000 claims description 18
- 239000004645 polyester resin Substances 0.000 claims description 18
- 229910019142 PO4 Inorganic materials 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 10
- 239000010452 phosphate Substances 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 9
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 9
- 238000007334 copolymerization reaction Methods 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 125000005609 naphthenate group Chemical group 0.000 claims description 6
- 125000005474 octanoate group Chemical group 0.000 claims description 6
- 239000000049 pigment Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000001879 gelation Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 150000001451 organic peroxides Chemical class 0.000 claims description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 235000021317 phosphate Nutrition 0.000 description 8
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 3
- 229960001826 dimethylphthalate Drugs 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- MKYQVWPVVHMCOU-UHFFFAOYSA-N 1-dibromophosphoryloxyethane Chemical compound CCOP(Br)(Br)=O MKYQVWPVVHMCOU-UHFFFAOYSA-N 0.000 description 2
- IXDLCMAMECXPRB-UHFFFAOYSA-N 2-(2,2-dichloroethoxycarbonyl)benzoic acid Chemical compound ClC(COC(C=1C(C(=O)O)=CC=CC1)=O)Cl IXDLCMAMECXPRB-UHFFFAOYSA-N 0.000 description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical group COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- 229910000669 Chrome steel Inorganic materials 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- VNZQQAVATKSIBR-UHFFFAOYSA-L copper;octanoate Chemical compound [Cu+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O VNZQQAVATKSIBR-UHFFFAOYSA-L 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- TXFOLHZMICYNRM-UHFFFAOYSA-N dichlorophosphoryloxybenzene Chemical compound ClP(Cl)(=O)OC1=CC=CC=C1 TXFOLHZMICYNRM-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
- IPKKHRVROFYTEK-UHFFFAOYSA-N dipentyl phthalate Chemical compound CCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCC IPKKHRVROFYTEK-UHFFFAOYSA-N 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical group CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- RDWGLYCGVYTLAK-UHFFFAOYSA-N (2,3,4-tribromophenyl) dihydrogen phosphate Chemical compound OP(O)(=O)OC1=CC=C(Br)C(Br)=C1Br RDWGLYCGVYTLAK-UHFFFAOYSA-N 0.000 description 1
- XKMCVHMWMWTINX-UHFFFAOYSA-N (2,3,4-trichlorophenyl) dihydrogen phosphate Chemical compound OP(O)(=O)OC1=CC=C(Cl)C(Cl)=C1Cl XKMCVHMWMWTINX-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- SBPUMPCKAMRWQN-UHFFFAOYSA-N 1-[bromo(ethoxy)phosphoryl]oxyethane Chemical compound CCOP(Br)(=O)OCC SBPUMPCKAMRWQN-UHFFFAOYSA-N 0.000 description 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical group CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- NIHRETFAEJQJKQ-UHFFFAOYSA-N 2,2,2-tribromoethyl dihydrogen phosphate Chemical compound OP(O)(=O)OCC(Br)(Br)Br NIHRETFAEJQJKQ-UHFFFAOYSA-N 0.000 description 1
- JPSKCQCQZUGWNM-UHFFFAOYSA-N 2,7-Oxepanedione Chemical compound O=C1CCCCC(=O)O1 JPSKCQCQZUGWNM-UHFFFAOYSA-N 0.000 description 1
- DBQUKJMNGUJRFI-UHFFFAOYSA-N 2-(diethylamino)ethanol;hydron;chloride Chemical compound Cl.CCN(CC)CCO DBQUKJMNGUJRFI-UHFFFAOYSA-N 0.000 description 1
- LNYYKKTXWBNIOO-UHFFFAOYSA-N 3-oxabicyclo[3.3.1]nona-1(9),5,7-triene-2,4-dione Chemical compound C1=CC(C(=O)OC2=O)=CC2=C1 LNYYKKTXWBNIOO-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- ZKWMTSWKAJNMMA-UHFFFAOYSA-N CC(C)OP(=O)(O)Br Chemical compound CC(C)OP(=O)(O)Br ZKWMTSWKAJNMMA-UHFFFAOYSA-N 0.000 description 1
- VIFRENCIZQYCGB-UHFFFAOYSA-N CC1=CC=CC=C1OP(=O)(O)Br Chemical compound CC1=CC=CC=C1OP(=O)(O)Br VIFRENCIZQYCGB-UHFFFAOYSA-N 0.000 description 1
- NSJXHUXWHFXZTA-UHFFFAOYSA-N CCCC(C)OP(=O)(O)Cl Chemical compound CCCC(C)OP(=O)(O)Cl NSJXHUXWHFXZTA-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- YYQRGCZGSFRBAM-UHFFFAOYSA-N Triclofos Chemical compound OP(O)(=O)OCC(Cl)(Cl)Cl YYQRGCZGSFRBAM-UHFFFAOYSA-N 0.000 description 1
- UBDQVSSPNXWQNH-UHFFFAOYSA-N [bromo(methoxy)phosphoryl]oxymethane Chemical compound COP(Br)(=O)OC UBDQVSSPNXWQNH-UHFFFAOYSA-N 0.000 description 1
- ONVDWPOQKDMJBN-UHFFFAOYSA-N [bromo(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Br)OC1=CC=CC=C1 ONVDWPOQKDMJBN-UHFFFAOYSA-N 0.000 description 1
- NGFFLHMFSINFGB-UHFFFAOYSA-N [chloro(methoxy)phosphoryl]oxymethane Chemical compound COP(Cl)(=O)OC NGFFLHMFSINFGB-UHFFFAOYSA-N 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- DWPHWVJZBHLVPI-UHFFFAOYSA-N bromophosphonic acid Chemical compound OP(O)(Br)=O DWPHWVJZBHLVPI-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- RAHFIYVNPZBEBZ-UHFFFAOYSA-N chloro-(2-ethylphenoxy)phosphinic acid Chemical compound CCC1=CC=CC=C1OP(O)(Cl)=O RAHFIYVNPZBEBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ONYHPQJRXORCDD-UHFFFAOYSA-N dibromophosphoryloxybenzene Chemical compound BrP(Br)(=O)OC1=CC=CC=C1 ONYHPQJRXORCDD-UHFFFAOYSA-N 0.000 description 1
- VZUNXXUSMINMCM-UHFFFAOYSA-N dibromophosphoryloxymethane Chemical compound COP(Br)(Br)=O VZUNXXUSMINMCM-UHFFFAOYSA-N 0.000 description 1
- SNVCRNWSNUUGEA-UHFFFAOYSA-N dichlorophosphoryloxymethane Chemical compound COP(Cl)(Cl)=O SNVCRNWSNUUGEA-UHFFFAOYSA-N 0.000 description 1
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 1
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- DSSXKBBEJCDMBT-UHFFFAOYSA-M lead(2+);octanoate Chemical compound [Pb+2].CCCCCCCC([O-])=O DSSXKBBEJCDMBT-UHFFFAOYSA-M 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- ORSUTASIQKBEFU-UHFFFAOYSA-N n,n-diethylbutan-1-amine Chemical compound CCCCN(CC)CC ORSUTASIQKBEFU-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- YORMZGQXMARHOP-UHFFFAOYSA-N trichloromethyl dihydrogen phosphate Chemical compound OP(O)(=O)OC(Cl)(Cl)Cl YORMZGQXMARHOP-UHFFFAOYSA-N 0.000 description 1
- 229960001147 triclofos Drugs 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR911965A FR1349942A (fr) | 1962-10-11 | 1962-10-11 | Procédé d'obtention rapide de plaques incolores et transparentes à base de résines polyesters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH426256A true CH426256A (fr) | 1966-12-15 |
Family
ID=8788513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1238563A CH426256A (fr) | 1962-10-11 | 1963-10-09 | Procédé d'obtention rapide de plaques translucides ou transparentes |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE638370A (en:Method) |
| CH (1) | CH426256A (en:Method) |
| ES (1) | ES292405A1 (en:Method) |
| FR (1) | FR1349942A (en:Method) |
| NL (1) | NL298942A (en:Method) |
-
0
- BE BE638370D patent/BE638370A/xx unknown
- NL NL298942D patent/NL298942A/xx unknown
-
1962
- 1962-10-11 FR FR911965A patent/FR1349942A/fr not_active Expired
-
1963
- 1963-10-09 CH CH1238563A patent/CH426256A/fr unknown
- 1963-10-11 ES ES0292405A patent/ES292405A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES292405A1 (es) | 1964-03-16 |
| NL298942A (en:Method) | |
| BE638370A (en:Method) | |
| FR1349942A (fr) | 1964-01-24 |
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