JP2020504214A - ホスホネートオリゴマーによるエポキシ樹脂の硬化 - Google Patents
ホスホネートオリゴマーによるエポキシ樹脂の硬化 Download PDFInfo
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- JP2020504214A JP2020504214A JP2019536309A JP2019536309A JP2020504214A JP 2020504214 A JP2020504214 A JP 2020504214A JP 2019536309 A JP2019536309 A JP 2019536309A JP 2019536309 A JP2019536309 A JP 2019536309A JP 2020504214 A JP2020504214 A JP 2020504214A
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- Prior art keywords
- phosphonate
- composition
- end groups
- oligomeric
- bis
- 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.)
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- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 title claims description 123
- 229920000647 polyepoxide Polymers 0.000 title description 35
- 239000003822 epoxy resin Substances 0.000 title description 33
- 239000000203 mixture Substances 0.000 claims abstract description 82
- 238000000034 method Methods 0.000 claims abstract description 49
- -1 diaryl phosphonates Chemical class 0.000 claims description 73
- 239000000178 monomer Substances 0.000 claims description 60
- 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 59
- 239000003054 catalyst Substances 0.000 claims description 58
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 38
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 36
- JRCBAJFWUZDKAP-UHFFFAOYSA-N OC(O)=O.OP(O)=O Chemical compound OC(O)=O.OP(O)=O JRCBAJFWUZDKAP-UHFFFAOYSA-N 0.000 claims description 30
- 238000006384 oligomerization reaction Methods 0.000 claims description 29
- 238000010438 heat treatment Methods 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 239000011541 reaction mixture Substances 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 239000004593 Epoxy Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 14
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 10
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 10
- 229930185605 Bisphenol Natural products 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000000835 fiber Substances 0.000 claims description 9
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 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 7
- 150000001336 alkenes Chemical class 0.000 claims description 6
- 239000000919 ceramic Substances 0.000 claims description 6
- 150000001345 alkine derivatives Chemical class 0.000 claims description 5
- 239000003733 fiber-reinforced composite Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 4
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims description 4
- 239000006260 foam Substances 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 4
- 229920001187 thermosetting polymer Polymers 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 3
- 239000010408 film Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 239000002023 wood Substances 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 2
- 125000005496 phosphonium group Chemical group 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract description 61
- 229920000642 polymer Polymers 0.000 abstract description 57
- 238000010586 diagram Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 52
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 239000006085 branching agent Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- 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 14
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 239000000155 melt Substances 0.000 description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 229910052698 phosphorus Inorganic materials 0.000 description 11
- 239000011574 phosphorus Substances 0.000 description 11
- 239000000654 additive Substances 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 8
- 238000002485 combustion reaction Methods 0.000 description 8
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 238000001723 curing Methods 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- 239000003063 flame retardant Substances 0.000 description 7
- 238000005809 transesterification reaction 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
- 239000004793 Polystyrene Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 239000003365 glass fiber Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003426 co-catalyst Substances 0.000 description 4
- 229920006351 engineering plastic Polymers 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920001230 polyarylate Polymers 0.000 description 4
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- 239000004417 polycarbonate Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229920001567 vinyl ester resin Polymers 0.000 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 description 3
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920000049 Carbon (fiber) Polymers 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229920000106 Liquid crystal polymer Polymers 0.000 description 3
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229920002732 Polyanhydride Polymers 0.000 description 3
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- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
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- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000002993 cycloalkylene group Chemical group 0.000 description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
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- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
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- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
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- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/14—Macromolecular materials
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Abstract
Description
この出願は、「フェノール−OH末端基を持たないホスホネートオリゴマーによるエポキシ樹脂の硬化」と題する2017年1月5日に出願された米国仮特許出願第62/442774の優先権と利益を主張し、その全体が参照により本明細書に組み込まれる。
共同研究契約の締約国:該当なし
コンパクトディスクで提出された資料の参照による組み込み:該当なし
式中、Arは芳香族基であり、−O−Ar−O−は、芳香族ジヒドロキシ化合物または芳香族ジオールに由来するものであり、Rは、C1−20アルキル、C2−20アルケン、C2−20アルキン、C5−20シクロアルキル、またはC6−20アリールであり、nは2から約20、2から約10、または2から約5の整数、またはこれらの範囲の間の任意の整数である。
式中、n2、p2、およびqはそれぞれ独立して0、1、2、3、または4であり、Raは、それぞれの場合独立して、非置換または置換C1−10ヒドロカルビルであり;Xaは単結合、−O−、−S−、−S(O)−、−S(O)2−、−C(O)−、または環状または非環状、芳香族または非芳香族のC1−18ヒドロカルビレンであり、酸素、窒素、硫黄、ケイ素、またはリンから選択される1つ以上のヘテロ原子をさらに含むことができる。本明細書で使用される用語「ヒドロカルビル」は、単独で使用される場合も、別の用語の接頭辞、接尾辞、または断片として使用される場合も、「置換ヒドロカルビル」として特に識別されない限り、炭素および水素のみを含む残基を指す。ヒドロカルビル残基は、脂肪族または芳香族、直鎖、環式、二環式、分岐、飽和、または不飽和であり得る。また、脂肪族、芳香族、直鎖、環状、二環式、分岐、飽和、および不飽和の炭化水素部分の組み合わせを含むことができる。用語「置換」は、ヒドロキシル、アミノ、チオール、カルボキシル、カルボキシレート、アミド、ニトリル、スルフィド、ジスルフィド、ニトロ、C1−18アルキル、C1−18アルコキシル、C6−18アリール、C6−18アリールオキシル、C7−18アルキルアリール、またはC7−18アルキルアリールオキシルなどの少なくとも1つの置換基を含むことを意味する。用語「置換された」は、ハロゲン(すなわち、F、Cl、Br、I)の包含をさらに可能にする。
式中、Ar1およびAr2は、それぞれ独立して、芳香族基であり、−O−Ar1−O−および−O−Ar2−O−は、構造(II)に記載のジヒドロキシ化合物から誘導され得る。
Rは、C1−20アルキル、C2−20アルケン、C2−20アルキン、C5−20シクロアルキル、またはC6−20アリールである。R1は、メチレン、エチレン、プロピレン、ブチレン、ペンチレンなどのC1−20アルキレンまたはシクロアルキレンであることができ、特定の実施形態では、R1は、これらに限定されないが、1,4−シクロヘキシルジメタノール、1,4−ブタンジオール、1,3−プロパンジオール、エチレンジオール、エチレングリコールなど、およびそれらの組み合わせなどの脂肪族ジオールに由来することができる。R2は、独立して、C1−20アルキレン、C2−20アルケニレン、C2−20アルキリニレン、C5−20シクロアルキレン、またはC6−20アリーレンであり、各Z1は、独立して、C1−20アルキレン、C2−20アルケニレン、C2−20アルキリニレン、C5−20シクロアルキレン、またはC6−20アリーレンである。特定の実施形態では、R2は、アジピン酸、ジメチルテレフタル酸、テレフタル酸、イソフタル酸、ナフタレンジカルボン酸などまたはそれらの誘導体またはそれらの組み合わせから誘導することができる。特定の実施形態では、R2は、ナフタレン、フェニレン、ビフェニレン、プロパン−2,2−ジイルジベンジレンなどの芳香族基であってもよく、いくつかの実施形態では、R2は、例えば、ジメチルテレフタレート、ジメチルイソフタレート、ジメチルナフタレートなど、およびそれらの組み合わせから誘導することができる。したがって、R2は、例えば、ナフタレン、フェニルであり得、これらの両方は、環上の任意の位置で置換され得る。そのようなコオリゴ(ホスホン酸カーボネート)、またはコオリゴ(ホスホン酸エステル)は、ブロックコオリゴ(ホスホン酸カーボネート)またはブロックコオリゴ(ホスホン酸エステル)であり得る。ここにおいて、各m1、n1、およびp1は同じでも異なっていてもよく、独立して、1から約20、1から約10、または2から約5の整数、またはこれらの範囲の任意の整数であり、コオリゴマーは、ホスホネートおよびカーボネートブロック、または、ホスホネートおよびエステルブロックの明確な繰り返しを含む。
式中、m、n、p、m1、n1、p1、およびR1とR2は上記で定義されたとおりである。
式中、各R6および各R7は独立して水素、C1−4アルキル、各yおよびyyは独立して1〜5の整数であり、RはC1−20アルキル、C2−20アルケン、C2−20アルキンであり、C5−20シクロアルキル、またはC6−20アリールであり得る。いくつかの実施形態では、ホスホン酸ジアリールエステルは、メチルホスホン酸ジフェニル(DPP)またはメチルジフェノキシホスフィンオキシドであり得る。
式中、各R3、R4、およびR5は、独立して水素、C1−4アルキル、およびp、q、およびrのそれぞれが独立して1〜5の整数であり得る。種々の実施形態では、分岐剤は、1,1,1−トリス(4−ヒドロキシフェニル)エタン、リン酸トリアリールエステル、トリおよびテトラ官能性カーボネートまたはエステルなど、およびそれらの組み合わせであり得、特定の例示的な実施形態では、分岐薬剤はリン酸トリフェニルであってもよい。特定の実施形態では、実施形態のオリゴマーホスホネートを調製するために使用されるトリヒドロキシおよびテトラヒドロキシ化合物には、これに限定されないが、フロログルシノール、4,6−ジメチル−2,4,6−トリ−(4−ヒドロキシフェニル)−2−ヘプテン、4,6−ジメチル−2,4,6−トリ−(4−ヒドロキシフェニル)−ヘプタン、1,3,5−トリ−(4−ヒドロキシフェニル)−ベンゼン、1,1,1−トリ−(4−ヒドロキシフェニル)−エタン、トリ−(4−ヒドロキシフェニル)−フェニルメタン、2,2−ビス−[4,4−ビス−(4−ヒドロキシフェニル)−シクロヘキシル]−プロパン、2,4−ビス−(4−ヒドロキシフェニル)イソプロピルフェノール、2,6−ビス−(2’−ヒドロキシ−5’−メチルベンジル)−4−メチルフェノール2−(4−ヒドロキシフェニル)−2−(2,4−ジヒドロキシフェノール)−プロパン、テトラ−(4−ヒドロキシフェニル)メタン、テトラ−[4−(4−ヒドロキシフェニルイソプロピル)フェノキシ]−メタン、1,4−ビス−(4,4’’−ジヒドロキシトリフェニルメチル)−ベンゼンなど、およびそれらの組み合わせおよびそれらの混合物が含まれ得る。
式中、Yは窒素、リン、またはヒ素であり、+cはYに関連付けられた電荷を表し、Ra、Rb、Rc、およびRdは、フェニル、tert−ブチル、メチル、エチル、プロピル、ブチル、または触媒がオリゴマー化触媒として機能するよう提供された他の基であり、Aはこれに限定されないが、フェノラート、アセテート、ボロハイドライド、ハロゲン、水酸化物、プロピオネート、ギ酸塩、ブチレートなどの対アニオンであり、−cはAに関連付けられた電荷である。いくつかの実施形態では、Yはリンであり、Ra、Rb、Rc、およびRdはフェニルであり、アニオンはフェノラートまたはアセテートである。特定の実施形態では、触媒は、例えば、テトラフェニルホスホニウム触媒またはその誘導体などのホスホニウム触媒、およびテトラアリールボロヒドリドなどの関連アニオン、ハロゲン化物、および置換または非置換フェノラート基であってもよい。特定の実施形態では、触媒はテトラフェニルホスホニウムフェノラートであってもよい。
本発明は、その特定の好ましい実施形態を参照してかなり詳細に説明されたが、他のバージョンも可能である。したがって、添付の特許請求の範囲の精神および範囲は、本明細書に含まれる説明および好ましいバージョンに限定されるべきではない。本発明の様々な態様は、以下の非限定的な例を参照して説明される。以下の実施例は、例示のみを目的とするものであり、いかなる方法でも本発明を限定するものと解釈されるべきではない。
分子量分布は、UV検出(254nm)を使用したゲル浸透クロマトグラフィー(GPC)により、テトラヒドロフラン(THF)におけるオリゴマーの0.2%溶液を測定することにより決定した。機器のキャリブレーションは、既知の分子量の線形ポリスチレン(PS)標準で実施した。WinGPCソフトウェアを使用して、クロマトグラムから重量平均(Mw)および数平均(Mn)を評価した。
両鎖末端のフェニルホスホン酸エステル末端オリゴマー「ビス−フェニル」は、ホスホン酸フェニル終端オリゴマー「ビスフェニル」は、機械式撹拌機と蒸留塔を備えた6Lステンレス鋼反応器で、1反応器プロセスで合成された。この反応器に、2,2−ビス−(4−ヒドロキシフェニル)プロパン(ビスフェノールA、1100g、4.82mol)、メチルホスホン酸ジフェニル(DPP)(1800g、7.26mol)、および触媒、テトラフェニルホスホニウムフェノラート(6.5g、15mmol)を窒素下で添加した。混合物を窒素下で190℃まで加熱した後、圧力を15kPaに維持しながら、450分かけて200℃から270℃まで上げた。反応器の温度をさらに360分間270℃に保ちながら、圧力を徐々に0.03kPa(完全真空)に下げた。生成物は、反応器の底部の染料を通して液体窒素浴に押し出され、粗い白色粒状生成物として分離された。
両鎖末端のフェニルホスホン酸エステル末端オリゴマー「ビスフェニル」は、単一の反応器で溶融縮合プロセスにより合成された。1.7xモル過剰のメチルホスホン酸ジフェニル(DPP)を、窒素下で2,2−ビス−(4−ヒドロキシフェニル)プロパン(ビスフェノールA)に加えた。触媒テトラフェニルホスホニウムフェノラートを、溶融物中のモノマーに0.62mmol/molビスフェノールAの濃度で添加した。モノマー/触媒混合物を190℃に加熱して反応を開始し、圧力を30kPaに下げ、次に、温度を190℃から290℃に徐々に上げながら、580分かけて圧力を30から0.06kPaに下げた。過剰のジフェニルメチルホスホネートモノマーは、反応をさらに800分間真空下(0.06kPa)で290℃に保持することにより除去した。生成物を水中ペレット化により抽出し、乾燥させ、透明白色ペレットとして単離した。
末端基が混合したホスホネートオリゴマーは、2段階の溶融縮合プロセスにより合成された。等モル量の2,2−ビス−(4−ヒドロキシフェニル)プロパン(ビスフェノールA)を窒素下でメチルホスホン酸ジフェニルに加えた。触媒テトラフェニルホスホニウムフェノラートを0.2mmol/molビスフェノールAの濃度でモノマーに添加した。モノマー/触媒混合物を260℃に60分間加熱した後、260℃から280℃に徐々に上げながら、360分かけて圧力を30から1.5kPaに下げた。生成物は、反応器の底部の染料を通して液体窒素浴に押し出され、粗い白色粒状生成物として分離された。
両鎖末端に約50%のヒドロキシル末端基をもつホスホネートオリゴマー「ビス−OH」は、2段階溶融縮合プロセスにより合成された。1.2xモル過剰の2,2−ビス−(4−ヒドロキシフェニル)プロパン(ビスフェノールA)を窒素下でメチルホスホン酸ジフェニルに加えた。触媒テトラフェニルホスホニウムフェノラート(30%フェノール)を0.3mmol/molビスフェノールAの濃度でモノマーに添加した。モノマー/触媒混合物を260℃に加熱して反応を開始し、その後徐々に275℃に加熱し、合計420分かけて圧力を30kPaから0.05kPaに下げた。生成物を水中ペレット化により抽出し、乾燥させ、透明なオフホワイトのペレットとして単離した。
両鎖末端に95%を超えるフェノール性ヒドロキシル末端基を有するホスホネートオリゴマー「ビス−OH」は、2段階の溶融縮合プロセスによって合成された。1.2xモル過剰の2,2−ビス−(4−ヒドロキシフェニル)プロパン(ビスフェノールA)を窒素下でメチルホスホン酸ジフェニルに加えた。触媒テトラフェニルホスホニウムフェノラート(30%フェノール)を0.3mmol/molビスフェノールAの濃度でモノマーに添加した。190℃から段階的に温度を上げて反応を開始し、次に、190℃から290℃に徐々に加熱し、580分かけて圧力を30kPaから0.06kPaに下げた。生成物を水中ペレット化により抽出し、乾燥させ、透明白色ペレットとして単離した。
実施例1〜3および比較例1に記載のオリゴマーを含む配合物のテストバー(125mm×13mm×4mm厚)を調製し、190℃のオーブンで2時間硬化させた。全てのサンプルは、エポキシ樹脂(39重量%)中のホスホネートオリゴマーの負荷レベルが同等であった。UL 94垂直燃焼チャンバを使用して、試験サンプルのFR性能をスクリーニングした。バーは垂直軸に沿って吊り下げられ、3/4インチの炎がサンプルに10秒間適用される。1回目(t1)および2回目(t2)の露出後の自己消火時間を記録した。V0評価の場合、点火炎を除去した後の最大燃焼時間(tmax)は10秒を超えてはならず、5つの試験片の合計燃焼時間(t1+t2)は50秒を超えてはならない。
Claims (29)
- オリゴマーホスホネートを有する組成物であって、全オリゴマーホスホネートの少なくとも約50%が1つ以上の非反応性末端基を有する組成物。
- 請求項1記載の組成物において、前記オリゴマーホスホネートは、オリゴホスホネート、ランダムまたはブロックコオリゴ(ホスホン酸エステル)およびコオリゴ(ホスホン酸カーボネート)を有するものである、組成物。
- 請求項1記載の組成物において、前記オリゴマーホスホネートは、線状オリゴマーホスホネート、分岐オリゴマーホスホネート、またはそれらの組み合わせを有するものである、組成物。
- 請求項1記載の組成物において、前記オリゴマーホスホネートは、約500g/モル〜約5000g/モルの数平均分子量を有するものである、組成物。
- 請求項1記載の組成物において、前記オリゴマーホスホネートは、ビスフェノールに由来する単位を有するものである、組成物。
- 請求項6記載の組成物において、前記−O−Ar−O−は、レゾルシノール、ヒドロキノン、ビスフェノールA、ビスフェノールF、4,4’−ビフェノール、フェノールフタレイン(誘導体)、4,4’−チオジフェノール、4,4’−スルホニルジフェノール、3,3,5−トリメチルシクロヘキシルジフェノール、またはその組み合わせに由来する、組成物。
- 請求項1記載の組成物において、前記オリゴホスホネートは末端を有し、前記非反応性末端基は前記末端の約50%〜約99%を構成するものである、組成物。
- 請求項8記載の組成物において、前記非反応性末端基は前記末端の約90%〜約98%を構成するものである、組成物。
- 請求項8記載の組成物において、前記非反応性末端基は、前記オリゴマーホスホネートの全末端の90%以上を構成するものである、組成物。
- 請求項8記載の組成物において、前記末端は、40%未満の反応性末端基をさらに有するものである、組成物。
- 請求項11記載の組成物において、前記反応性末端基は前記末端の総数の約15%〜約0.2%を構成するものである、組成物。
- 請求項12記載の組成物において、前記反応性末端基は約10%〜約0.5%を構成するものである、組成物。
- 請求項12記載の組成物において、前記反応性末端基はフェノール性OH末端基を有し、全末端は60%未満のフェノール性OH末端基を有するものである、組成物。
- 請求項12記載の組成物において、前記末端が80%を超えるフェニル末端基を有するものである、組成物。
- 請求項12記載の組成物において、前記末端が約40%未満のビス−OH末端基を有するものである、組成物。
- 請求項12記載の組成物において、反応性末端基が芳香族ヒドロキシル末端基を有するものである、組成物。
- 請求項1記載の組成物であって、1つ以上の熱硬化性ポリマーをさらに有するものである、組成物。
- 請求項18記載の組成物において、前記1つ以上の熱硬化性ポリマーはエポキシである、組成物。
- 請求項18記載の組成物であって、少なくとも1つの硬化剤をさらに有するものである、組成物。
- 40未満のKOHを有するオリゴマーホスホネートを有する組成物。
- 非反応性オリゴマーホスホネートを調製するための方法であって、前記方法は、
モノマー混合物を作製するためにホスホネートモノマーとコモノマーとを混合する工程であって、前記モノマー混合物はモル過剰のホスホネートモノマーを有するものである、混合する工程と、
前記モノマー混合物を加熱する工程と、
反応混合物を作製するために前記モノマー混合物にオリゴマー化触媒を添加する工程と、
重合温度を維持する工程と
を有する、方法。 - 請求項22記載の方法において、前記ホスホネートモノマーは、ホスホン酸ジアリールエステルまたはホスホン酸ジアリールから選択されるものである、方法。
- 請求項22記載の方法において、前記コモノマーは、芳香族ジヒドロキシ化合物、二価フェノール、ビスフェノールなど、またはそれらの組み合わせから選択されるものである、方法。
- 請求項22記載の方法において、前記オリゴマー化触媒は、ホスホニウム触媒である、方法。
- 請求項24記載の方法において、前記ホスホニウム触媒がテトラフェニルホスホニウムフェノラートを有するものである、方法。
- オリゴマーホスホネートを有する製造品であって、全オリゴマーホスホネートの約60%〜約100%が2つ以上の非反応性末端基を有するものである、製造品。
- 請求項27記載の製造品において、前記製造品は、プラスチック、金属、セラミック、または木材製品のコーティング、自立フィルム、繊維、発泡体、成形品、繊維強化複合材、支持部品、電気部品、電気コネクタ、プリント配線板、ハウジング、従属部品および部品、テレビ、コンピューター、ラップトップコンピューター、プリンター、携帯電話、ビデオゲーム、DVDプレーヤー、ステレオ、デジタル音楽プレーヤー、ハンドヘルドビデオプレーヤー、およびタッチスクリーンからなる群から選択されるものである、製造品。
- 請求項27記載の製造品において、前記製造品は、電気部品、電気コネクタ、プリント配線板、プリント回路基板、テレビ、コンピューター、ラップトップコンピューター、プリンター、コピー機、スキャナー、携帯電話、ビデオゲーム、DVDプレーヤー、ステレオ、デジタル音楽プレーヤー、ハンドヘルドビデオプレーヤー、またはタッチスクリーンに使用される積層体または繊維強化複合材である、製造品。
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