CN105367775B - 基于双酚的高分子量无规共聚(膦酸酯碳酸酯) - Google Patents
基于双酚的高分子量无规共聚(膦酸酯碳酸酯) Download PDFInfo
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- CN105367775B CN105367775B CN201510854525.6A CN201510854525A CN105367775B CN 105367775 B CN105367775 B CN 105367775B CN 201510854525 A CN201510854525 A CN 201510854525A CN 105367775 B CN105367775 B CN 105367775B
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- phosphonate
- carbonate
- phosphonate carbonate
- polymer
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- -1 Phosphonate ester Chemical class 0.000 title claims abstract description 64
- 238000007334 copolymerization reaction Methods 0.000 title claims abstract description 18
- 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 title claims description 45
- 150000002148 esters Chemical class 0.000 title abstract description 5
- 229930185605 Bisphenol Natural products 0.000 title description 8
- JRCBAJFWUZDKAP-UHFFFAOYSA-N OC(O)=O.OP(O)=O Chemical compound OC(O)=O.OP(O)=O JRCBAJFWUZDKAP-UHFFFAOYSA-N 0.000 claims description 75
- 229920000642 polymer Polymers 0.000 claims description 57
- 230000002378 acidificating effect Effects 0.000 claims description 47
- 239000003054 catalyst Substances 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 43
- 229920001577 copolymer Chemical compound 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 239000000178 monomer Substances 0.000 claims description 31
- 238000005809 transesterification reaction Methods 0.000 claims description 28
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims description 27
- ZLLNYWQSSYUXJM-UHFFFAOYSA-M tetraphenylphosphanium;phenoxide Chemical compound [O-]C1=CC=CC=C1.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZLLNYWQSSYUXJM-UHFFFAOYSA-M 0.000 claims description 25
- 230000008569 process Effects 0.000 claims description 22
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 17
- 229920000515 polycarbonate Polymers 0.000 claims description 13
- 239000004417 polycarbonate Substances 0.000 claims description 13
- 239000000155 melt Substances 0.000 claims description 12
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 11
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- 239000000835 fiber Substances 0.000 claims description 10
- 239000000945 filler Substances 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- 239000002216 antistatic agent Substances 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 229920001707 polybutylene terephthalate 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
- 229920000106 Liquid crystal polymer Polymers 0.000 claims description 3
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims description 3
- 229920002732 Polyanhydride Polymers 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
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- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 3
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- 239000004793 Polystyrene Substances 0.000 claims description 3
- 229920002396 Polyurea Polymers 0.000 claims description 3
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 3
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- JDRCQIRZJMJGMW-UHFFFAOYSA-N benzhydrylphosphonic acid Chemical compound C=1C=CC=CC=1C(P(O)(=O)O)C1=CC=CC=C1 JDRCQIRZJMJGMW-UHFFFAOYSA-N 0.000 claims 2
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000009826 distribution Methods 0.000 abstract description 10
- HPUPGAFDTWIMBR-UHFFFAOYSA-N [methyl(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(C)OC1=CC=CC=C1 HPUPGAFDTWIMBR-UHFFFAOYSA-N 0.000 description 75
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 29
- 230000003301 hydrolyzing effect Effects 0.000 description 15
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 239000011541 reaction mixture Substances 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
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- 238000009835 boiling Methods 0.000 description 7
- 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 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000012512 characterization method Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000011552 falling film Substances 0.000 description 6
- 239000003063 flame retardant Substances 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- KLFXGMZYFVBYAR-UHFFFAOYSA-N methyl(phenoxy)phosphinic acid Chemical compound CP(O)(=O)OC1=CC=CC=C1 KLFXGMZYFVBYAR-UHFFFAOYSA-N 0.000 description 5
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 5
- 238000006068 polycondensation reaction Methods 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 5
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- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002463 lignoceryl 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])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001421 myristyl 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])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000005677 organic carbonates Chemical class 0.000 description 1
- 125000000913 palmityl 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])([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 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GEPYJHDOGKHEMZ-UHFFFAOYSA-M tetraphenylphosphanium;fluoride Chemical compound [F-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GEPYJHDOGKHEMZ-UHFFFAOYSA-M 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
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- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/02—Aliphatic polycarbonates
- C08G64/0208—Aliphatic polycarbonates saturated
- C08G64/0225—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
- C08G64/0258—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing phosphorus
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
- C08G64/083—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing phosphorus
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- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/30—General preparatory processes using carbonates
- C08G64/307—General preparatory processes using carbonates and phenols
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
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- Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
实施例 | 18 | 19 | 20 |
单体 | |||
BPA[g] | 79.67 | 79.67 | 79.67 |
DPC[g] | 74.69 | 62.895 | 43.24 |
DPP[g] | 4.55 | 18.23 | 40.99 |
TPPP[g] | 0.04715 | 0.0943 | 0.1886 |
DPP中的酸性组分*[%] | 0.007 | 0.007 | 0.007 |
DPP/(DPP+DPC)[质量-%] | 5.7 | 22.5 | 48.7 |
DPP/(DPP+DPC)[mol-%] | 5.0 | 20.0 | 45.0 |
(DPP+DPC)/BPA[mol/mol] | 1.052 | 1.052 | 1.051 |
1mbar阶段在305℃的时间[h] | 2 | 2 | 2 |
ηrel | 1.23 | 1.246 | 1.231 |
Mw[g/mole] | 21674 | 26403 | 42820 |
PD | 2.21 | 2.43 | 3.89 |
水解稳定性 | |||
Δηrel.至初始值 | |||
24小时之后 | -0.001 | -0.004 | -0.015 |
48小时之后 | -0.003 | -0.009 | -0.043 |
72小时之后 | -0.004 | -0.013 | -0.077 |
168小时之后 | -0.007 | -0.030 | -0.154 |
实施例 | 21 | 22 | 23 |
单体 | |||
BPA[g] | 1411 | 1411 | 1411 |
DPC[g] | 929 | 929 | 929 |
DPP[g] | 500 | 500 | 500 |
TPPP[g] | 1.67 | 1.67 | |
苯酚钠[g] | 0.05 | ||
DPP中的酸性组分*[%] | 0.03 | 0.03 | 0.92 |
DPP/(DPP+DPC)[质量-%] | 35 | 35 | 35 |
DPP/(DPP+DPC)[mol-%] | 31.7 | 31.7 | 31.7 |
(DPP+DPC)/BPA[mol/mol] | 1.027 | 1.027 | 1.027 |
总反应时间[min] | 615 | 615 | 355 |
在反应终点的转矩[Nm] | 8.4 | 10.7 | 8.9 |
ηrel | 1.237 | 1.25 | 1.247 |
Mw[g/摩尔] | 26715 | 28900 | 31900 |
Mn[g/摩尔] | 11400 | 12600 | 7600 |
PD | 2.34 | 2.29 | 4.18 |
水解稳定性 | |||
Δηrel.至初始值 | |||
24小时之后 | -0.009 | 0 | -0.032 |
48小时之后 | -0.015 | -0.007 | -0.051 |
72小时之后 | -0.015 | -0.022 | -0.044 |
Claims (28)
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US38369710P | 2010-09-16 | 2010-09-16 | |
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US61/383,686 | 2010-09-16 | ||
CN201180044917.6A CN103282405B (zh) | 2010-09-16 | 2011-09-16 | 基于双酚的高分子量无规共聚(膦酸酯碳酸酯) |
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EP (1) | EP2616496A4 (zh) |
JP (1) | JP5964307B2 (zh) |
KR (1) | KR101991704B1 (zh) |
CN (2) | CN105367775B (zh) |
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TWI473857B (zh) * | 2010-09-16 | 2015-02-21 | Frx Polymers Inc | 高分子量、無規、以雙酚為主之共聚(磷酸酯碳酸酯) |
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 |
WO2012165665A1 (ja) * | 2011-06-03 | 2012-12-06 | Arisawa Mfg. Co., Ltd. | 難燃性樹脂組成物、並びに該樹脂組成物を用いたフレキシブルプリント配線板用金属張積層板、カバーレイ、フレキシブルプリント配線板用接着シート及びフレキシブルプリント配線板 |
KR20150036294A (ko) | 2012-06-29 | 2015-04-07 | 에프알엑스 폴리머스, 인코포레이티드 | 폴리에스테르 코-포스포네이트 |
EP2948464A4 (en) | 2013-01-22 | 2016-12-07 | Frx Polymers Inc | PHOSPHORUS-BASED EPOXY BINDINGS AND COMPOSITIONS THEREOF |
EP3565822A4 (en) | 2017-01-05 | 2020-08-05 | FRX Polymers, Inc. | CURING EPOXY RESINS WITH PHOSPHONATE OLIGOMERS |
CN111615529A (zh) | 2018-01-16 | 2020-09-01 | 赢创运营有限公司 | 含纳米颗粒的组合物 |
CN108912404A (zh) * | 2018-08-22 | 2018-11-30 | 齐鲁工业大学 | 一种抗水抗油纳米纤维素复合膜的制备方法 |
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DE2925207A1 (de) | 1979-06-22 | 1981-01-29 | Bayer Ag | Thermoplastische, verzweigte, aromatische polyphosphonate, ihre verwendung und ein verfahren zu ihrer herstellung |
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 |
DE3001863A1 (de) * | 1980-01-19 | 1981-07-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von thermoplastischen aromatischen polyphosphonatocarbonaten verbesserter thermischer alterungsbestaendigkeit und deren verwendung |
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DE3517271A1 (de) | 1985-05-14 | 1986-11-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von copolyphosphonaten mit hoher kerbschlagzaehigkeit |
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TWI473857B (zh) * | 2010-09-16 | 2015-02-21 | Frx Polymers Inc | 高分子量、無規、以雙酚為主之共聚(磷酸酯碳酸酯) |
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TWI473857B (zh) | 2015-02-21 |
JP2013540168A (ja) | 2013-10-31 |
TW201221580A (en) | 2012-06-01 |
KR20140024238A (ko) | 2014-02-28 |
EP2616496A4 (en) | 2016-05-18 |
JP5964307B2 (ja) | 2016-08-03 |
CN103282405A (zh) | 2013-09-04 |
US20130158147A1 (en) | 2013-06-20 |
US8389664B2 (en) | 2013-03-05 |
RU2013117102A (ru) | 2014-10-27 |
EP2616496A2 (en) | 2013-07-24 |
CN105367775A (zh) | 2016-03-02 |
CN103282405B (zh) | 2016-01-20 |
US8648163B2 (en) | 2014-02-11 |
KR101991704B1 (ko) | 2019-06-21 |
WO2012037500A3 (en) | 2012-08-16 |
US20120068115A1 (en) | 2012-03-22 |
WO2012037500A2 (en) | 2012-03-22 |
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