NO771067L - Halogenholdige umettede bisestere samt polymerisater og kopolymerisater p} basis av disse estere. - Google Patents
Halogenholdige umettede bisestere samt polymerisater og kopolymerisater p} basis av disse estere.Info
- Publication number
- NO771067L NO771067L NO771067A NO771067A NO771067L NO 771067 L NO771067 L NO 771067L NO 771067 A NO771067 A NO 771067A NO 771067 A NO771067 A NO 771067A NO 771067 L NO771067 L NO 771067L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- esters
- bisacrylate
- bromine
- ether
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
- 229920000642 polymer Polymers 0.000 claims description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 238000006116 polymerization reaction Methods 0.000 claims description 20
- 239000003063 flame retardant Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000001246 bromo group Chemical group Br* 0.000 claims description 15
- 239000004033 plastic Substances 0.000 claims description 14
- 229920003023 plastic Polymers 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 6
- 150000001447 alkali salts Chemical class 0.000 claims description 5
- 239000002798 polar solvent Substances 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000007493 shaping process Methods 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 150000001298 alcohols Chemical group 0.000 claims description 3
- -1 ether alcohols Chemical class 0.000 claims description 3
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000002334 glycols Chemical class 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical group CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 11
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 239000003513 alkali Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229920006337 unsaturated polyester resin Polymers 0.000 description 4
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 241000428199 Mustelinae Species 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 229920001519 homopolymer Polymers 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
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- UJTHMGMWSSOKMD-UHFFFAOYSA-N [4-(prop-2-enoyloxymethyl)phenyl]methyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=C(COC(=O)C=C)C=C1 UJTHMGMWSSOKMD-UHFFFAOYSA-N 0.000 description 2
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical group [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000006253 efflorescence Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 206010037844 rash Diseases 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CAUZPKXGWLCQJX-UHFFFAOYSA-N C(C(=C)C)(=O)OC(C1=CC(=CC=C1)C(Cl)(Cl)OC(C(=C)C)=O)(Cl)Cl Chemical compound C(C(=C)C)(=O)OC(C1=CC(=CC=C1)C(Cl)(Cl)OC(C(=C)C)=O)(Cl)Cl CAUZPKXGWLCQJX-UHFFFAOYSA-N 0.000 description 1
- GSJJGQZEFCJFPH-UHFFFAOYSA-N C(C=C)(=O)OC(C1=CC(=CC=C1)C(Cl)(Cl)OC(C=C)=O)(Cl)Cl Chemical compound C(C=C)(=O)OC(C1=CC(=CC=C1)C(Cl)(Cl)OC(C=C)=O)(Cl)Cl GSJJGQZEFCJFPH-UHFFFAOYSA-N 0.000 description 1
- PMVSDNDAUGGCCE-TYYBGVCCSA-L Ferrous fumarate Chemical compound [Fe+2].[O-]C(=O)\C=C\C([O-])=O PMVSDNDAUGGCCE-TYYBGVCCSA-L 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-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
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- GEPKEOMRSGYOIR-UHFFFAOYSA-N [2,3,5,6-tetrachloro-4-(prop-2-enoyloxymethyl)phenyl]methyl prop-2-enoate Chemical compound ClC1=C(Cl)C(COC(=O)C=C)=C(Cl)C(Cl)=C1COC(=O)C=C GEPKEOMRSGYOIR-UHFFFAOYSA-N 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical class C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000010616 electrical installation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000001297 nitrogen containing inorganic group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003703 phosphorus containing inorganic group Chemical group 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004901 spalling Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000003685 thermal hair damage Effects 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000006839 xylylene group Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/14—Macromolecular materials
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/08—Organic materials containing halogen
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/24—Flameproof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2612843A DE2612843B2 (de) | 1976-03-26 | 1976-03-26 | Bis-acrylester und Bis-methacrylester, Verfahren zur Herstellung dieser Verbindungen und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO771067L true NO771067L (no) | 1977-09-27 |
Family
ID=5973465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO771067A NO771067L (no) | 1976-03-26 | 1977-03-25 | Halogenholdige umettede bisestere samt polymerisater og kopolymerisater p} basis av disse estere. |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US4149008A (de) |
| JP (1) | JPS52116430A (de) |
| AT (1) | AT350536B (de) |
| BE (1) | BE852844A (de) |
| CA (1) | CA1107293A (de) |
| DE (1) | DE2612843B2 (de) |
| DK (1) | DK134177A (de) |
| ES (1) | ES457190A1 (de) |
| FR (1) | FR2345421A1 (de) |
| GB (1) | GB1566614A (de) |
| IT (1) | IT1115914B (de) |
| NL (1) | NL7703266A (de) |
| NO (1) | NO771067L (de) |
| SE (1) | SE7703390L (de) |
| SU (1) | SU619109A3 (de) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4268433A (en) * | 1978-08-29 | 1981-05-19 | Fujitsu Limited | 1,2-Polybutadiene compositions and cured flame retarded 1,2-polybutadiene resin materials |
| US4369298A (en) * | 1980-05-27 | 1983-01-18 | Tokuyama Soda Kabushiki Kaisha | Novel cured resin, process for production thereof, and lens composed of said resin from bis(alkyleneoxyphenyl)-diacrylate, bis(alkyleneoxyphenyl)diallyl ether, bis(alkyleneoxyphenyl)diallyl carbonate monomers |
| DE3572829D1 (en) * | 1984-04-04 | 1989-10-12 | Hoechst Ag | Reaction product of olefinically unsaturated compounds with active hydrogen compounds, process for their preparation and 2-component coating systems based thereon |
| CA1248531A (en) * | 1984-04-17 | 1989-01-10 | Jeffrey C. Watkins | 4-substituted piperazine-2-carboxylic acids |
| DE3632215A1 (de) * | 1986-09-23 | 1988-03-24 | Dentaire Ivoclar Ets | Reaktiver organischer fuellstoff sowie dessen verwendung |
| FR2608614B1 (fr) * | 1986-12-19 | 1989-03-10 | Poudres & Explosifs Ste Nale | Composition solide thermoplastique radioreticulable et produits durcissables obtenus avec cette composition |
| IL86604A (en) * | 1988-06-02 | 1994-01-25 | Bromine Compounds Ltd | Flame-retardant preparations containing pentbromobenzyl acrylate or the reaction products in place of the acrylate |
| US4906713A (en) * | 1989-01-31 | 1990-03-06 | E. I. Du Pont De Nemours And Company | "Acrylic" ladder polymers |
| US5998499A (en) | 1994-03-25 | 1999-12-07 | Dentsply G.M.B.H. | Liquid crystalline (meth)acrylate compounds, composition and method |
| US6369164B1 (en) | 1993-05-26 | 2002-04-09 | Dentsply G.M.B.H. | Polymerizable compounds and compositions |
| US6353061B1 (en) | 1993-05-26 | 2002-03-05 | Dentsply Gmbh | α, ω-methacrylate terminated macromonomer compounds |
| CA2146816A1 (en) | 1994-04-22 | 1995-10-23 | Joachim E. Klee | Process and composition for preparing a dental polymer product |
| GB9714632D0 (en) * | 1997-07-12 | 1997-09-17 | Ici Plc | Process for the production of methyl methacrylate |
| CN113372928B (zh) * | 2020-03-09 | 2022-12-13 | 江苏和成显示科技有限公司 | 包含可聚合化合物的液晶组合物和液晶显示器件 |
| CN113372927B (zh) * | 2020-03-09 | 2022-12-13 | 江苏和成显示科技有限公司 | 包含可聚合化合物的液晶组合物和液晶显示器件 |
| CN113372925B (zh) * | 2020-03-09 | 2022-12-09 | 江苏和成显示科技有限公司 | 液晶组合物及其液晶显示器件 |
| CN113372926B (zh) * | 2020-03-09 | 2022-12-16 | 江苏和成显示科技有限公司 | 包含可聚合化合物的液晶组合物和液晶显示器件 |
| CN113372924B (zh) * | 2020-03-09 | 2023-05-23 | 江苏和成显示科技有限公司 | 可聚合化合物及其液晶组合物和液晶显示器件 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3225002A (en) | 1961-02-17 | 1965-12-21 | Pittsburgh Plate Glass Co | Diesters of terminally unsaturated monocarboxylic acids and halophenoxymethyl, alkane diols |
| US3277053A (en) | 1965-06-07 | 1966-10-04 | Eastman Kodak Co | Flame and heat resistant polymeric materials containing 2-(bromophenoxy or chlorophenoxy)ethyl and/or propyl acrylates and/or methacrylates |
| US3369058A (en) * | 1965-12-17 | 1968-02-13 | Robertson Co H H | Polymerizable ethylenically unsaturated carboxylic acid esters of diphenyl oxides and polymers containing the same |
| CH557674A (de) * | 1968-05-15 | 1975-01-15 | Espe Pharm Praep | Material zur herstellung von zahnfuellungen und zahnersatzteilen. |
| US3664992A (en) | 1968-12-19 | 1972-05-23 | Gaetano F D Alelio | Acrylic esters of halogenated acetylenic diols |
| US3650885A (en) | 1969-04-04 | 1972-03-21 | Sun Chemical Corp | Radiation-curable compositions |
| JPS523991B2 (de) * | 1972-10-30 | 1977-01-31 | ||
| US3770811A (en) * | 1973-03-23 | 1973-11-06 | H Lee | Diacrylate esters of hydrogenated bis-phenol and tolylene |
| US3932321A (en) * | 1973-06-18 | 1976-01-13 | Japan Synthetic Rubber Company Limited | Flame-retardant polymer composition |
| GB1464287A (en) * | 1974-02-22 | 1977-02-09 | Ciba Geigy Ag | Polymerisable esters |
| DE2430629A1 (de) * | 1974-06-26 | 1976-01-15 | Dynamit Nobel Ag | Tetrachlorxylyl- und tetrachlorxylylenacrylate, substituierte acrylate und ein verfahren zu deren herstellung |
| GB1516212A (en) * | 1974-06-26 | 1978-06-28 | Dynamit Nobel Ag | Halogenated aromatic esters |
-
1976
- 1976-03-26 DE DE2612843A patent/DE2612843B2/de not_active Ceased
-
1977
- 1977-03-22 GB GB12118/77A patent/GB1566614A/en not_active Expired
- 1977-03-23 SU SU772462811A patent/SU619109A3/ru active
- 1977-03-23 US US05/780,577 patent/US4149008A/en not_active Expired - Lifetime
- 1977-03-24 BE BE176088A patent/BE852844A/xx unknown
- 1977-03-24 IT IT48639/77A patent/IT1115914B/it active
- 1977-03-24 JP JP3275777A patent/JPS52116430A/ja active Pending
- 1977-03-24 SE SE7703390A patent/SE7703390L/xx unknown
- 1977-03-24 FR FR7708882A patent/FR2345421A1/fr not_active Withdrawn
- 1977-03-25 DK DK134177A patent/DK134177A/da unknown
- 1977-03-25 NL NL7703266A patent/NL7703266A/xx not_active Application Discontinuation
- 1977-03-25 ES ES457190A patent/ES457190A1/es not_active Expired
- 1977-03-25 CA CA274,816A patent/CA1107293A/en not_active Expired
- 1977-03-25 NO NO771067A patent/NO771067L/no unknown
- 1977-03-25 AT AT210877A patent/AT350536B/de not_active IP Right Cessation
-
1979
- 1979-07-19 US US06/059,091 patent/US4284732A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2612843A1 (de) | 1977-09-29 |
| IT1115914B (it) | 1986-02-10 |
| CA1107293A (en) | 1981-08-18 |
| US4149008A (en) | 1979-04-10 |
| ATA210877A (de) | 1978-11-15 |
| US4284732A (en) | 1981-08-18 |
| JPS52116430A (de) | 1977-09-29 |
| DE2612843B2 (de) | 1979-10-31 |
| FR2345421A1 (fr) | 1977-10-21 |
| SU619109A3 (ru) | 1978-08-05 |
| SE7703390L (sv) | 1977-09-27 |
| GB1566614A (en) | 1980-05-08 |
| BE852844A (fr) | 1977-07-18 |
| DK134177A (da) | 1977-09-27 |
| AT350536B (de) | 1979-06-11 |
| NL7703266A (nl) | 1977-09-28 |
| ES457190A1 (es) | 1978-08-16 |
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