GB883754A - Polyesters containing phosphorus and process for their manufacture - Google Patents
Polyesters containing phosphorus and process for their manufactureInfo
- Publication number
- GB883754A GB883754A GB3755157A GB3755157A GB883754A GB 883754 A GB883754 A GB 883754A GB 3755157 A GB3755157 A GB 3755157A GB 3755157 A GB3755157 A GB 3755157A GB 883754 A GB883754 A GB 883754A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacted
- acid
- phosphonic acid
- product
- ethylene glycol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920000728 polyester Polymers 0.000 title abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 23
- 229920000642 polymer Polymers 0.000 abstract 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 12
- -1 aliphatic diester Chemical class 0.000 abstract 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 8
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 8
- 150000002148 esters Chemical class 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 6
- 235000011187 glycerol Nutrition 0.000 abstract 6
- IBDMRHDXAQZJAP-UHFFFAOYSA-N dichlorophosphorylbenzene Chemical compound ClP(Cl)(=O)C1=CC=CC=C1 IBDMRHDXAQZJAP-UHFFFAOYSA-N 0.000 abstract 5
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 5
- 239000000194 fatty acid Substances 0.000 abstract 5
- 229930195729 fatty acid Natural products 0.000 abstract 5
- 150000004665 fatty acids Chemical class 0.000 abstract 5
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 abstract 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 4
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 4
- 240000006240 Linum usitatissimum Species 0.000 abstract 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 235000004426 flaxseed Nutrition 0.000 abstract 4
- 239000001530 fumaric acid Substances 0.000 abstract 4
- 150000005846 sugar alcohols Polymers 0.000 abstract 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 3
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 3
- 150000002978 peroxides Chemical class 0.000 abstract 3
- KDRBAEZRIDZKRP-UHFFFAOYSA-N 2,2-bis[3-(aziridin-1-yl)propanoyloxymethyl]butyl 3-(aziridin-1-yl)propanoate Chemical compound C1CN1CCC(=O)OCC(COC(=O)CCN1CC1)(CC)COC(=O)CCN1CC1 KDRBAEZRIDZKRP-UHFFFAOYSA-N 0.000 abstract 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical class CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 abstract 2
- FBSFTJQYCLLGKH-UHFFFAOYSA-N cyclohexylphosphonic acid Chemical compound OP(O)(=O)C1CCCCC1 FBSFTJQYCLLGKH-UHFFFAOYSA-N 0.000 abstract 2
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 abstract 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 239000004922 lacquer Substances 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- 239000000376 reactant Substances 0.000 abstract 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 2
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 abstract 1
- MLSZIADXWDYFKM-UHFFFAOYSA-N 1-dichlorophosphorylethene Chemical compound ClP(Cl)(=O)C=C MLSZIADXWDYFKM-UHFFFAOYSA-N 0.000 abstract 1
- YWDFOLFVOVCBIU-UHFFFAOYSA-N 1-dimethoxyphosphorylpropane Chemical compound CCCP(=O)(OC)OC YWDFOLFVOVCBIU-UHFFFAOYSA-N 0.000 abstract 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical class C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 abstract 1
- IVVJWFHNROTJDG-UHFFFAOYSA-N 2,3-bis(hydroxymethyl)butane-1,2,3,4-tetrol Chemical compound OCC(O)(CO)C(O)(CO)CO IVVJWFHNROTJDG-UHFFFAOYSA-N 0.000 abstract 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 abstract 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical class COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 abstract 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 abstract 1
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 abstract 1
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- ZDNFTNPFYCKVTB-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,4-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C=C1 ZDNFTNPFYCKVTB-UHFFFAOYSA-N 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- ZKXWKVVCCTZOLD-UHFFFAOYSA-N copper;4-hydroxypent-3-en-2-one Chemical compound [Cu].CC(O)=CC(C)=O.CC(O)=CC(C)=O ZKXWKVVCCTZOLD-UHFFFAOYSA-N 0.000 abstract 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 abstract 1
- 150000004292 cyclic ethers Chemical class 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- OZOVYDFZXJIQPR-UHFFFAOYSA-N dimethoxyphosphorylcyclohexane Chemical compound COP(=O)(OC)C1CCCCC1 OZOVYDFZXJIQPR-UHFFFAOYSA-N 0.000 abstract 1
- BNKAXGCRDYRABM-UHFFFAOYSA-N ethenyl dihydrogen phosphate Chemical class OP(O)(=O)OC=C BNKAXGCRDYRABM-UHFFFAOYSA-N 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 abstract 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 235000021388 linseed oil Nutrition 0.000 abstract 1
- 239000000944 linseed oil Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 125000005394 methallyl group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 abstract 1
- 229920005646 polycarboxylate Polymers 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 239000002685 polymerization catalyst Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 229920001451 polypropylene glycol Polymers 0.000 abstract 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- 150000003440 styrenes Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000001384 succinic acid Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 abstract 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 abstract 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
- C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
- C08G63/6924—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Polymers containing both carboxylate and phosphate groups are made by reacting (a) a dihalide or a lower aliphatic diester of a phosphonic acid having directly attached to phosphorous, a monovalent alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl or alkaryl group, or such a group substituted by a halogen, hydroxyl or alkoxy radical or, in the case of an aromatic group, in addition to the aforesaid substituents a nitro and/or amino radical, with (b) a polyhydric alcohol containing up to 14 carbon atoms and (c) a polycarboxylic aliphatic, cycloaliphatic or aromatic polycarboxylic acid or an anhydride, ester or acid halide of such an acid. All three components (a), (b) and (c) may be reacted simultaneously or alternaitvely a polymeric phosphonate or polycarboxylate may first be prepared from components (a) and (b) or (b) and (c) respectively and these polymers further reacted with the other acid and possibly additional alcohol. When using a halide as reactant, reaction may be effected in the presence of a tertiary amine or a metal; when using an ester as reactant, an ester-intercharge catalyst (many specified) may be used. Specified polycarboxylic acids are malonic, succinic, chlorosuccinic, adipic, sebacic, phthalic, isophthalic, terephthalic, tetrachlorophthalic, chlorendic, maleic, fumaric, itaconic, metaconic, citraconic, malic, tartaric, trimseric, tricarballylic, aconitic, citric, hemimeltitic and pyromellitic acids. Specified polyhydric alcohols are ethylene glycol, polyethylene glycols, propylene glycol, polypropylene glycols, butylene glycol, hexanediol, butenediol, pinacone, 1:2-diphenyl ethylene glycol, phthalyl alcohol, tricyclodecane di- or tri-methylol, glycerine, hexanetriol, trimethylol propane, pentaerythritol, dipentaerythritol and sorbitol, halogenated derivatives of those polyhydric alcohols, and partial ethers or esters of higher polyhydric alcohols. The polymers may be modified with monohydric alcohols (e.g. methyl, ethyl, propyl, butyl, ethylhexyl, allyl, oleyl or chloroethyl alcohols) or with monocarboxylic acids (e.g. acetic, butyric, crotonic, sorbic, benzoic, chlorobenzoic, furanecarboxylic, furfuracrylic, cinnamic, nicotinic, lactic, hydroxybutyric chloroacetic, chlorbutyric, brombenzoic or linseed fatty acids). The polymers are soluble in hydrocarbons, cyclic ethers, the mono-ethyl ether of ethylene glycol, esters of glycolic acid and phenols and may be used as flame-proofing impregnating materials, adhesives and lacquers. When the polymers are unsaturated e.g. when maleic acid, fumaric acid, crotonic acid, allyl alcohol or vinyl phosphates are used, they may be homopolymerized or copolymerized with monomer such as styrene, alkylated styrenes, vinyl naphthalene, vinyl acetate, acrylic and methacrylic acid and the esters and nitriles thereof, alkyl and methalkyl esters of saturated or unsaturated mono- or poly-carboxylic acids, allyl and methallyl carbonates, allyl and methallyl phosphates or phosphonates, esters of vinyl phosphonic acid, triallyl cyanurate, polyesters containing allyl or methallyl groups and halogen substituted derivatives thereof; polymerization is effected by irradiation and/or heating and/or a polymerization catalyst (many specified). The addition polymers may be admixed with highly chlorinated hydrocarbons and strengthened with organic or inorganic fibres. In Examples (1) and (15) Diethylene glycol and phenyl phosphonic acid dichloride are reacted and the product reacted with maleic anhydride to provide a polymer polymerizable by benzoyl peroxide; (2) Diethylene glycol is reacted with vinyl phosphonic acid dichloride and the product reacted with maleic anhydride to provide a polymer polymerizable by a peroxide; (3) Hexanetriol and phenyl phosphonic acid dichloride are reacted and the product reacted with ethylene glycol and maleic anhydride to provide a polymer polymerizable by peroxides; (4) Ethylene glycol and phenyl phosphonic acid dichloride are reacted and the product reacted with hexanetriol, butanol and maleic anhydride; (5) Dimethyl maleate and ethylene glycol are reacted and the product reacted with phenyl phosphonic acid dichloride to provide a polymer polymerizable by peroxides; (6) Glycerine and cyclohexane phosphonic acid dichloride are reacted and the product reacted with terephthalic acid and linseed fatty acids; (7) Glycerine and cyclohexyl phosphonic acid dimethyl ester are reacted and the product reacted with fumaric acid to provide a polymer polymerizable by benzoyl peroxide; (8) Butylene glycol and phenyl phosphonic acid dimethyl ester are reacted and the product reacted with maleic anhydride to provide a polymerizable polymer; (9) Ethylene glycol, glycerine and propyl phosphonic acid dimethyl ester are reacted and the product reacted with succinic acid; (10) Glycerine, cyclohexane phosphonic acid dimethyl ester and linseed oil fatty acid are reacted and the product reacted with fumaric acid; (11) Hexanetriol, benzyl phosphonic acid and linseed fatty acids are reacted and the product reacted with maleic anhydride; (12) Hexane triol and cyclohexane phosphonic acid diallyl ester are reacted and the product reacted with maleic anhydride and butanol to provide a polymer polymerizable by heat (and possibly in the presence of an initiator); (13) Glycerine and phthalic anhydride are reacted and the product reacted with phenyl phosphonic acid dimethyl ester; (14) Glycerine, cyclohexane phosphonic acid dimethyl ester and linseed fatty acids are reacted and the product reacted with dimethyl terephthalate and fumaric acid; the resin may be made into a lacquer by dissolving it in a solvent and adding phosphoric and/or perchloric acid; (16)-(18) A polymer from ethylene glycol, dimethyl maleate and phenyl phosphonic acid dichloride is copolymerized with styrene, vinyl toluene, or diallyl terephthalate in the presence of benzoyl peroxide; (19) A polymer from butylene glycol, cyclohexyl phosphonic acid, dimethyl ester and maleic anhydride is copolymerized with vinyl acetate in the presence of p-toluene sulphonic acid and copper acetyl acetonate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF21800A DE1164093B (en) | 1956-11-30 | 1956-11-30 | Process for the production of polyesters containing phosphonic acid |
| DEF22045A DE1128652B (en) | 1956-12-31 | 1956-12-31 | Process for the production of self-extinguishing plastics by polymerizing unsaturated, phosphorus-containing polyesters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB883754A true GB883754A (en) | 1961-12-06 |
Family
ID=25974000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3755157A Expired GB883754A (en) | 1956-11-30 | 1957-12-02 | Polyesters containing phosphorus and process for their manufacture |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH380953A (en) |
| FR (1) | FR1196971A (en) |
| GB (1) | GB883754A (en) |
| SE (1) | SE303600B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3406153A (en) * | 1962-05-16 | 1968-10-15 | Du Pont | Process of producing polyethylene terephthalate |
| US3412070A (en) * | 1961-06-24 | 1968-11-19 | Hoechst Ag | Fibers of a terephthalate/ethylene glycol polyester containing less than 0.5 percent by weight of phosphorus incorporated therein by phosphonic acid ester linkages |
| US4419299A (en) | 1981-12-14 | 1983-12-06 | The Dow Chemical Co. | Phosphonopolyester oligomers |
| CN115403759A (en) * | 2022-11-02 | 2022-11-29 | 山东一诺威聚氨酯股份有限公司 | Halogen-free flame-retardant polyether ester polyol and preparation method and application thereof |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3298967A (en) * | 1963-04-04 | 1967-01-17 | Union Carbide Corp | Process for preparing high molecular weight phosphonate polymers |
| DE2346787C3 (en) | 1973-09-17 | 1980-05-08 | Hoechst Ag, 6000 Frankfurt | Flame retardant linear polyesters, processes for their manufacture and their use |
| DE2900686A1 (en) * | 1979-01-10 | 1980-07-24 | Cassella Ag | POLYESTER SOLUBLE OR DISPERSIBLE IN WATER, METHOD FOR THE PRODUCTION THEREOF AND THE USE THEREOF AS A LEVELING AGENT, LEVELING AGENT AND METHOD FOR EVENLY COLORING |
| DE2948183A1 (en) * | 1979-11-30 | 1981-06-04 | Cassella Ag, 6000 Frankfurt | PREPARATION FOR BRIGHTENING SYNTHESIS FIBERS, THEIR PRODUCTION AND USE |
| CH649215A5 (en) * | 1981-04-29 | 1985-05-15 | Hoffmann La Roche | PHARMACEUTICAL PREPARATIONS. |
| IT1252236B (en) * | 1991-12-18 | 1995-06-05 | Enichem Sintesi | LINEAR COPOLYESTER CONTAINING PHOSPHORUS, PREPARATION PROCEDURE AND USE AS AN ANTI-FLAME ADDITIVE |
-
1957
- 1957-11-28 CH CH5318357A patent/CH380953A/en unknown
- 1957-11-29 FR FR1196971D patent/FR1196971A/en not_active Expired
- 1957-12-02 GB GB3755157A patent/GB883754A/en not_active Expired
-
1962
- 1962-03-15 SE SE289862A patent/SE303600B/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3412070A (en) * | 1961-06-24 | 1968-11-19 | Hoechst Ag | Fibers of a terephthalate/ethylene glycol polyester containing less than 0.5 percent by weight of phosphorus incorporated therein by phosphonic acid ester linkages |
| US3406153A (en) * | 1962-05-16 | 1968-10-15 | Du Pont | Process of producing polyethylene terephthalate |
| US4419299A (en) | 1981-12-14 | 1983-12-06 | The Dow Chemical Co. | Phosphonopolyester oligomers |
| CN115403759A (en) * | 2022-11-02 | 2022-11-29 | 山东一诺威聚氨酯股份有限公司 | Halogen-free flame-retardant polyether ester polyol and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| SE303600B (en) | 1968-09-02 |
| FR1196971A (en) | 1959-11-27 |
| CH380953A (en) | 1964-08-15 |
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