IL44766A - Preparation of brominated mono-and polyhydroxyneopentanes and esters thereof with aliphatic dicarboxylic acids - Google Patents
Preparation of brominated mono-and polyhydroxyneopentanes and esters thereof with aliphatic dicarboxylic acidsInfo
- Publication number
- IL44766A IL44766A IL44766A IL4476674A IL44766A IL 44766 A IL44766 A IL 44766A IL 44766 A IL44766 A IL 44766A IL 4476674 A IL4476674 A IL 4476674A IL 44766 A IL44766 A IL 44766A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- esters
- product
- aliphatic dicarboxylic
- dicarboxylic acids
- Prior art date
Links
- -1 aliphatic dicarboxylic acids Chemical class 0.000 title claims description 20
- 150000002148 esters Chemical class 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 26
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 15
- CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 claims description 14
- 239000003063 flame retardant Substances 0.000 claims description 14
- 239000001361 adipic acid Substances 0.000 claims description 12
- 235000011037 adipic acid Nutrition 0.000 claims description 12
- 150000008064 anhydrides Chemical class 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- QEJPOEGPNIVDMK-UHFFFAOYSA-N 3-bromo-2,2-bis(bromomethyl)propan-1-ol Chemical compound OCC(CBr)(CBr)CBr QEJPOEGPNIVDMK-UHFFFAOYSA-N 0.000 claims description 10
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000011496 polyurethane foam Substances 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical class CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 49
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 20
- 239000006260 foam Substances 0.000 description 17
- 229940059574 pentaerithrityl Drugs 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 230000032683 aging Effects 0.000 description 10
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- OYSVBCSOQFXYHK-UHFFFAOYSA-N 1,3-dibromo-2,2-bis(bromomethyl)propane Chemical compound BrCC(CBr)(CBr)CBr OYSVBCSOQFXYHK-UHFFFAOYSA-N 0.000 description 4
- OKESOAYXLGYXLN-UHFFFAOYSA-N BrCC(C(Br)(Br)OC(CCCCC(=O)OC(C(CBr)(C)C)(Br)Br)=O)(C)C Chemical compound BrCC(C(Br)(Br)OC(CCCCC(=O)OC(C(CBr)(C)C)(Br)Br)=O)(C)C OKESOAYXLGYXLN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- UQMRXXBMQJLTLE-UHFFFAOYSA-N (1,1,3-tribromo-2,2-dimethylpropyl) acetate Chemical compound CC(=O)OC(Br)(Br)C(C)(C)CBr UQMRXXBMQJLTLE-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 2
- KVIPHDKUOLVVQN-UHFFFAOYSA-N ethene;hydrate Chemical compound O.C=C KVIPHDKUOLVVQN-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- GRJISTUCPUHFOJ-UHFFFAOYSA-N 1,3-dibromo-2,2-dimethylpropane-1,3-diol Chemical class BrC(O)C(C)(C(O)Br)C GRJISTUCPUHFOJ-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- YEIFONWNCFYMKW-UHFFFAOYSA-N 2,2-bis(bromomethyl)oxetane Chemical compound BrCC1(CBr)CCO1 YEIFONWNCFYMKW-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-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
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101100381997 Danio rerio tbc1d32 gene Proteins 0.000 description 1
- 241000360590 Erythrites Species 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 101100381999 Mus musculus Tbc1d32 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000006227 byproduct Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical class OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
- C08G63/6824—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3802—Low-molecular-weight compounds having heteroatoms other than oxygen having halogens
- C08G18/3804—Polyhydroxy compounds
- C08G18/3806—Polyhydroxy compounds having chlorine and/or bromine atoms
- C08G18/381—Polyhydroxy compounds having chlorine and/or bromine atoms having bromine atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0014—Use of organic additives
- C08J9/0023—Use of organic additives containing oxygen
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/05—Alcohols; Metal alcoholates
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL7546847A IL46847A (en) | 1974-05-02 | 1975-03-17 | Rekmoval of hbr from brominated pentaerythritols (mono- or polyhydroxyneopentanes) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US363203A US3883581A (en) | 1973-05-23 | 1973-05-23 | Preparation of brominated pentaerythritols and esters utilizing certain dibasic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44766A0 IL44766A0 (en) | 1974-07-31 |
| IL44766A true IL44766A (en) | 1977-03-31 |
Family
ID=23429257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44766A IL44766A (en) | 1973-05-23 | 1974-05-02 | Preparation of brominated mono-and polyhydroxyneopentanes and esters thereof with aliphatic dicarboxylic acids |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3883581A (it) |
| JP (1) | JPS5756451B2 (it) |
| BE (1) | BE815438A (it) |
| CA (1) | CA1029742A (it) |
| DE (1) | DE2424474C2 (it) |
| FR (1) | FR2230604B1 (it) |
| GB (1) | GB1459623A (it) |
| IL (1) | IL44766A (it) |
| IT (1) | IT1013196B (it) |
| NL (1) | NL182560C (it) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1058223A (en) * | 1973-04-05 | 1979-07-10 | Ronald G. Tigner | Removal of hbr from brominated pentaerythritols |
| JPS5830285B2 (ja) * | 1975-03-11 | 1983-06-28 | ザ ダウ ケミカル カンパニ− | シユウソカペンタエリトリツトカラノ シユウカスイソノジヨキヨホウ |
| US4154966A (en) * | 1977-11-23 | 1979-05-15 | Dead Sea Bromine Co. Ltd. | Process for the preparation of dibromoneopentylglycol (DBNG) |
| LU78663A1 (fr) * | 1977-12-09 | 1979-06-13 | Labofina Sa | Compositions de resines styreniques ignifuges et leurs procedes de preparation |
| DE3125338A1 (de) * | 1981-06-27 | 1983-01-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von bromhydrinen aus polyolen |
| IL76434A0 (en) * | 1985-09-20 | 1986-01-31 | Bromine Compounds Ltd | Flame retardant polymer compositions |
| IL77701A (en) * | 1986-01-24 | 1988-11-30 | Bromine Compounds Ltd | Liquid flame retardants for hydraulic fluids |
| GB2191208A (en) * | 1986-06-05 | 1987-12-09 | Basf Corp | High resiliency molded polyurethane foams |
| US4873377A (en) * | 1988-10-03 | 1989-10-10 | Ethyl Corporation | Preparation of dibromoneopentyl glycol |
| US4913848A (en) * | 1988-10-12 | 1990-04-03 | Ethyl Corporation | Process for producing a high purity dibromoneopentyl glycol product |
| US4929775A (en) * | 1989-05-30 | 1990-05-29 | Ethyl Corporation | Process for preparing brominated pentaerythritols |
| US5135961A (en) * | 1990-07-27 | 1992-08-04 | Ethyl Corporation | Stabilized flame retardant polyol composition |
| DE19528537A1 (de) | 1995-08-03 | 1997-02-06 | Basf Ag | Flammgeschützte Hartschaumstoffe auf Isocyanatbasis |
| CN101016227B (zh) * | 2007-02-08 | 2010-09-08 | 宜兴市中正化工有限公司 | 三溴新戊醇的合成方法及精制 |
| EP2632967A1 (en) | 2010-10-29 | 2013-09-04 | Lubrizol Advanced Materials, Inc. | Flame-retarding oligomeric brominated urethane compositions |
| CN106589189A (zh) * | 2016-11-18 | 2017-04-26 | 寿光市泰源化工有限公司 | 适用于工业化生产的聚丙烯酸五溴苄酯与三溴新戊醇配合制备的方法 |
| CN110452347A (zh) * | 2019-07-10 | 2019-11-15 | 广东德美精细化工集团股份有限公司 | 一种具有防水性能的聚氨酯中间体及其制备方法 |
| CN110903188B (zh) * | 2019-09-17 | 2023-01-03 | 丛强 | 一种制备三溴新戊醇乙酸酯的方法 |
| CN110903163B (zh) * | 2019-09-17 | 2023-01-03 | 丛强 | 一种三溴新戊醇的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3118003A (en) * | 1964-01-14 | Production of pentaerythritol |
-
1973
- 1973-05-23 US US363203A patent/US3883581A/en not_active Expired - Lifetime
-
1974
- 1974-04-29 CA CA198,331A patent/CA1029742A/en not_active Expired
- 1974-05-02 IL IL44766A patent/IL44766A/en unknown
- 1974-05-13 GB GB2112174A patent/GB1459623A/en not_active Expired
- 1974-05-13 NL NLAANVRAGE7406390,A patent/NL182560C/xx not_active IP Right Cessation
- 1974-05-16 JP JP49053966A patent/JPS5756451B2/ja not_active Expired
- 1974-05-20 DE DE2424474A patent/DE2424474C2/de not_active Expired
- 1974-05-21 IT IT51140/74A patent/IT1013196B/it active
- 1974-05-21 FR FR7417662A patent/FR2230604B1/fr not_active Expired
- 1974-05-22 BE BE144665A patent/BE815438A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7406390A (it) | 1974-11-26 |
| NL182560B (nl) | 1987-11-02 |
| JPS5756451B2 (it) | 1982-11-30 |
| AU6890674A (en) | 1975-11-20 |
| JPS5019707A (it) | 1975-03-01 |
| BE815438A (fr) | 1974-11-22 |
| IT1013196B (it) | 1977-03-30 |
| FR2230604B1 (it) | 1976-12-24 |
| CA1029742A (en) | 1978-04-18 |
| NL182560C (nl) | 1988-04-05 |
| DE2424474A1 (de) | 1974-12-12 |
| US3883581A (en) | 1975-05-13 |
| IL44766A0 (en) | 1974-07-31 |
| FR2230604A1 (it) | 1974-12-20 |
| GB1459623A (en) | 1976-12-22 |
| DE2424474C2 (de) | 1982-12-30 |
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