CN104861171B - 不溶且支化的聚膦酸酯及其相关方法 - Google Patents
不溶且支化的聚膦酸酯及其相关方法 Download PDFInfo
- Publication number
- CN104861171B CN104861171B CN201510176885.5A CN201510176885A CN104861171B CN 104861171 B CN104861171 B CN 104861171B CN 201510176885 A CN201510176885 A CN 201510176885A CN 104861171 B CN104861171 B CN 104861171B
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- Prior art keywords
- polyphosphonates
- reaction mixture
- insoluble
- phenol
- time
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 48
- 229920000642 polymer Polymers 0.000 claims abstract description 64
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims description 50
- 239000011541 reaction mixture Substances 0.000 claims description 50
- -1 phosphonic acids diaryl ester Chemical class 0.000 claims description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- 239000003054 catalyst Substances 0.000 claims description 34
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 31
- 229930185605 Bisphenol Natural products 0.000 claims description 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 19
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical group [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims description 19
- 239000006085 branching agent Substances 0.000 claims description 16
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 239000000835 fiber Substances 0.000 claims description 10
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 9
- 239000000155 melt Substances 0.000 claims description 9
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 8
- FVKYHUBHBRJSDA-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]phenol propane Chemical compound OC1=CC=C(C=C1)C(C)(C)C1=CC=C(C=C1)O.CCC FVKYHUBHBRJSDA-UHFFFAOYSA-N 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000004743 Polypropylene Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000004642 Polyimide Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 239000006260 foam Substances 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 4
- 229920000515 polycarbonate Polymers 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920001721 polyimide Polymers 0.000 claims description 4
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 3
- 229920002732 Polyanhydride Polymers 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 229920002396 Polyurea Polymers 0.000 claims description 3
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920001230 polyarylate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 239000004800 polyvinyl chloride Substances 0.000 claims description 3
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 3
- 229920001567 vinyl ester resin Polymers 0.000 claims description 3
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 claims description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 2
- 229920013636 polyphenyl ether polymer Polymers 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 150000001336 alkenes Chemical class 0.000 claims 1
- WGWACCCAJWZIML-UHFFFAOYSA-N benzene;buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N.C1=CC=CC=C1 WGWACCCAJWZIML-UHFFFAOYSA-N 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- 238000005809 transesterification reaction Methods 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 description 10
- 229920001707 polybutylene terephthalate Polymers 0.000 description 9
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 7
- 229940106691 bisphenol a Drugs 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 6
- 230000003301 hydrolyzing effect Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 229940031826 phenolate Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- NHIAEZJOVSXCRX-UHFFFAOYSA-N C(CCC)S(=O)(=O)O.[F] Chemical compound C(CCC)S(=O)(=O)O.[F] NHIAEZJOVSXCRX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical class C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 229920006351 engineering plastic Polymers 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000010517 secondary reaction Methods 0.000 description 2
- 0 *P(Oc1ccccc1)(Oc1ccccc1)=O Chemical compound *P(Oc1ccccc1)(Oc1ccccc1)=O 0.000 description 1
- CRXRDDSCLVHGAF-UHFFFAOYSA-N 1-phenylfluorene-9,9-diol Chemical class C=12C(O)(O)C3=CC=CC=C3C2=CC=CC=1C1=CC=CC=C1 CRXRDDSCLVHGAF-UHFFFAOYSA-N 0.000 description 1
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004425 Makrolon Substances 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009954 braiding Methods 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- IMHDGJOMLMDPJN-UHFFFAOYSA-N dihydroxybiphenyl Natural products OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 1
- WGMBWDBRVAKMOO-UHFFFAOYSA-L disodium;4-[2-(4-oxidophenyl)propan-2-yl]phenolate Chemical compound [Na+].[Na+].C=1C=C([O-])C=CC=1C(C)(C)C1=CC=C([O-])C=C1 WGMBWDBRVAKMOO-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- SAWKFRBJGLMMES-UHFFFAOYSA-N methylphosphine Chemical class PC SAWKFRBJGLMMES-UHFFFAOYSA-N 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 230000000007 visual effect Effects 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L85/00—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers
- C08L85/02—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
- C08L67/03—Polyesters derived from dicarboxylic acids and dihydroxy compounds the dicarboxylic acids and dihydroxy compounds having the carboxyl- and the hydroxy groups directly linked to aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Artificial Filaments (AREA)
- Fireproofing Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95260807P | 2007-07-30 | 2007-07-30 | |
| US60/952,608 | 2007-07-30 | ||
| CN200880106263A CN101802054A (zh) | 2007-07-30 | 2008-07-30 | 不溶且支化的聚膦酸酯及其相关方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200880106263A Division CN101802054A (zh) | 2007-07-30 | 2008-07-30 | 不溶且支化的聚膦酸酯及其相关方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104861171A CN104861171A (zh) | 2015-08-26 |
| CN104861171B true CN104861171B (zh) | 2018-04-24 |
Family
ID=40120224
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510176885.5A Expired - Fee Related CN104861171B (zh) | 2007-07-30 | 2008-07-30 | 不溶且支化的聚膦酸酯及其相关方法 |
| CN200880106263A Pending CN101802054A (zh) | 2007-07-30 | 2008-07-30 | 不溶且支化的聚膦酸酯及其相关方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200880106263A Pending CN101802054A (zh) | 2007-07-30 | 2008-07-30 | 不溶且支化的聚膦酸酯及其相关方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9745424B2 (enExample) |
| EP (1) | EP2181141B1 (enExample) |
| JP (2) | JP5603238B2 (enExample) |
| KR (1) | KR101510085B1 (enExample) |
| CN (2) | CN104861171B (enExample) |
| ES (1) | ES2549732T3 (enExample) |
| WO (1) | WO2009018336A2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009018336A2 (en) | 2007-07-30 | 2009-02-05 | Frx Polymers, Inc. | Insoluble and branched polyphosphonates and methods related thereto |
| US20110237695A1 (en) * | 2010-03-23 | 2011-09-29 | Clariant International Ltd. | Flame Retardant Combinations For Polyester Elastomers And Flame Retarded Extrusion Or Molding Compositions Therefrom |
| JP2014503698A (ja) | 2010-11-17 | 2014-02-13 | エフアールエックス ポリマーズ、インク． | ポリエステル繊維の難燃剤としてのホスホン酸ポリマー、コポリマー、およびそれぞれのオリゴマー |
| KR101424525B1 (ko) | 2010-12-22 | 2014-08-01 | 에프알엑스 폴리머스, 인코포레이티드 | 올리고머성 포스포네이트 및 이를 포함하는 조성물 |
| KR101362871B1 (ko) * | 2010-12-29 | 2014-02-14 | 제일모직주식회사 | 가교형 폴리포스포네이트, 그의 제조 방법 및 이를 포함하는 난연성 열가소성 수지 조성물 |
| CN109971144A (zh) * | 2011-04-14 | 2019-07-05 | Frx 聚合物股份有限公司 | 聚膦酸酯和共聚膦酸酯添加剂混合物 |
| TWI638005B (zh) * | 2011-08-19 | 2018-10-11 | 法克斯聚合物股份有限公司 | 具優越耐火性之熱塑性聚胺基甲酸酯 |
| TWI460212B (zh) * | 2011-12-22 | 2014-11-11 | Frx Polymers Inc | 高度分枝寡聚膦酸酯及包含該高度分枝寡聚膦酸酯之組成物 |
| CN104603176B (zh) | 2012-06-29 | 2018-12-28 | Frx聚合物股份有限公司 | 聚酯共-膦酸酯 |
| WO2014116669A1 (en) | 2013-01-22 | 2014-07-31 | Frx Polymers, Inc. | Phosphorus containing epoxy compounds and compositions therefrom |
| US20150105484A1 (en) | 2013-10-14 | 2015-04-16 | Frx Polymers, Inc. | Flame retardant thermoplastic elastomers for extrusion or injection molding |
| EP3114170A4 (en) | 2014-03-04 | 2017-11-01 | FRX Polymers, Inc. | Epoxy compositions |
| JPWO2017002780A1 (ja) * | 2015-07-02 | 2018-04-12 | 三菱ケミカル株式会社 | ポリエステルフィルム及び調光フィルム |
| KR102668113B1 (ko) * | 2017-01-05 | 2024-05-23 | 에프알엑스 폴리머스, 인코포레이티드 | 포스포네이트 올리고머를 갖는 에폭시 수지의 경화 |
| TW201938774A (zh) | 2018-01-16 | 2019-10-01 | 德商贏創德固賽有限責任公司 | 含有奈米粒子之組成物 |
| WO2020079565A1 (en) | 2018-10-16 | 2020-04-23 | Sabic Global Technologies B.V. | Continuous fiber reinforced composite prepreg formed of flame retardant polyester |
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| CN1777632A (zh) * | 2003-02-24 | 2006-05-24 | 特拉通系统股份有限公司 | 支化聚膦酸酯 |
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| US2716101A (en) * | 1952-09-10 | 1955-08-23 | Eastman Kodak Co | Polymeric organo-phosphonates containing phosphato groups |
| US3326852A (en) * | 1964-08-10 | 1967-06-20 | Owens Illinois Inc | Resinous polymeric phosphonates |
| DE2925206A1 (de) * | 1979-06-22 | 1981-01-29 | Bayer Ag | Aromatische polyesterphosphonate, verfahren zu ihrer herstellung und ihre verwendung zur herstellung thermoplastischer formkoerper |
| DE2925208A1 (de) * | 1979-06-22 | 1981-01-29 | Bayer Ag | Verfahren zur herstellung von aromatischen thermoplastischen polyphosphonatocarbonaten |
| DE2925207A1 (de) * | 1979-06-22 | 1981-01-29 | Bayer Ag | Thermoplastische, verzweigte, aromatische polyphosphonate, ihre verwendung und ein verfahren zu ihrer herstellung |
| DE2944093A1 (de) * | 1979-10-31 | 1981-05-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von thermoplastischen aromatischen polyphosphonaten verbesserter thermischer alterungsbestaendigkeit und deren verwendung |
| DE3002792A1 (de) * | 1980-01-26 | 1981-07-30 | Bayer Ag, 5090 Leverkusen | Flammhemmende zusammensetzung aus polyphenylenether, polystyrolharz und polyphosphonat |
| DE3520296A1 (de) * | 1985-06-07 | 1986-12-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von copolyphosphonaten mit hoher zaehigkeit |
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| IT1251154B (it) * | 1991-08-07 | 1995-05-04 | Enichem Sintesi | Pentaeritril fosfonati e loro utilizzo in composizioni polimeriche termoplastiche autoestinguenti |
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| ATE478882T1 (de) * | 2004-08-31 | 2010-09-15 | Icl Ip America | Verfahren zur herstellung von diarylalkylphosphonat und oligomere/polymere derivate davon |
| WO2009018336A2 (en) | 2007-07-30 | 2009-02-05 | Frx Polymers, Inc. | Insoluble and branched polyphosphonates and methods related thereto |
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2008
- 2008-07-30 WO PCT/US2008/071585 patent/WO2009018336A2/en not_active Ceased
- 2008-07-30 JP JP2010520151A patent/JP5603238B2/ja not_active Expired - Fee Related
- 2008-07-30 CN CN201510176885.5A patent/CN104861171B/zh not_active Expired - Fee Related
- 2008-07-30 KR KR1020107004481A patent/KR101510085B1/ko not_active Expired - Fee Related
- 2008-07-30 US US12/182,590 patent/US9745424B2/en not_active Expired - Fee Related
- 2008-07-30 CN CN200880106263A patent/CN101802054A/zh active Pending
- 2008-07-30 EP EP08782528.7A patent/EP2181141B1/en not_active Not-in-force
- 2008-07-30 ES ES08782528.7T patent/ES2549732T3/es active Active
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2014
- 2014-02-25 JP JP2014034420A patent/JP2014139317A/ja active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1633469A (zh) * | 2001-10-26 | 2005-06-29 | 拜尔公司 | 抗冲改性的阻燃性聚碳酸酯模塑组合物 |
| CN1777632A (zh) * | 2003-02-24 | 2006-05-24 | 特拉通系统股份有限公司 | 支化聚膦酸酯 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010535281A (ja) | 2010-11-18 |
| EP2181141A2 (en) | 2010-05-05 |
| KR101510085B1 (ko) | 2015-04-10 |
| KR20100053589A (ko) | 2010-05-20 |
| JP5603238B2 (ja) | 2014-10-08 |
| US20090032770A1 (en) | 2009-02-05 |
| CN104861171A (zh) | 2015-08-26 |
| ES2549732T3 (es) | 2015-11-02 |
| WO2009018336A2 (en) | 2009-02-05 |
| EP2181141B1 (en) | 2015-09-02 |
| CN101802054A (zh) | 2010-08-11 |
| US9745424B2 (en) | 2017-08-29 |
| WO2009018336A3 (en) | 2009-03-19 |
| JP2014139317A (ja) | 2014-07-31 |
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