JP2014533317A - ポリメタクリル酸無水物テロマー - Google Patents
ポリメタクリル酸無水物テロマー Download PDFInfo
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- JP2014533317A JP2014533317A JP2014541152A JP2014541152A JP2014533317A JP 2014533317 A JP2014533317 A JP 2014533317A JP 2014541152 A JP2014541152 A JP 2014541152A JP 2014541152 A JP2014541152 A JP 2014541152A JP 2014533317 A JP2014533317 A JP 2014533317A
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- Prior art keywords
- telomer
- acid
- methacrylic anhydride
- anhydride
- methacrylic
- Prior art date
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- 150000008064 anhydrides Chemical class 0.000 title claims description 28
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract description 64
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 claims abstract description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims abstract description 6
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 6
- 229920000642 polymer Polymers 0.000 claims description 71
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 26
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 14
- -1 hypophosphorous acid compound Chemical class 0.000 claims description 12
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 5
- 238000001694 spray drying Methods 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000008365 aqueous carrier Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 239000008188 pellet Substances 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000004580 weight loss Effects 0.000 description 10
- 229920002125 Sokalan® Polymers 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 238000005102 attenuated total reflection Methods 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- 239000003999 initiator Substances 0.000 description 6
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000005702 oxyalkylene group Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FWMFMCKIDWLKIH-UHFFFAOYSA-N C(C(=C)C)(=O)O.[PH2](=O)O Chemical compound C(C(=C)C)(=O)O.[PH2](=O)O FWMFMCKIDWLKIH-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 238000012711 chain transfer polymerization Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000013480 data collection Methods 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000006254 rheological additive Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 241000220010 Rhode Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229920000535 Tan II Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- MOZXJNMWVQFSMF-UHFFFAOYSA-N chloro 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCl MOZXJNMWVQFSMF-UHFFFAOYSA-N 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 239000008235 industrial water Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000012899 standard injection Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/08—Anhydrides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
実施例1および2のメタクリル酸無水物の次亜リン酸テロマーは、以下の割合で次亜リン酸ナトリウムの存在下で水溶液中で重合されるpMAAポリマーから生成した。
実施例1Aの比較pMAAホモポリマー(Mw6000、次亜リン酸塩を有さず)について、また、次亜リン酸ナトリウム(SHP、8.8重量%、モノマーの総重量に基づいて)を有する、実施例1のメタクリル酸無水物の次亜リン酸ホモテロマー(Mw6000)についてTGA Q500(TA Instruments、New、Castle、DE)熱重量分析(TGA)装置を使用した。試料をTGA試験の前に凍結乾燥させた。両方の試料をN2中で加熱し、20℃/分にて30℃から110℃の加熱傾斜により加熱し、続いて110℃にて30分間保持して試料をさらに乾燥させた。保持後、試料を20℃/分にて300℃まで加熱した。無水物形成は、水の形態において重量損失により示され、これは誘導体重量損失が上昇するにつれて見られ、次いで無水物形成後、一定の値まで低下し、再びポリマーを分解している間のみ上昇した。以下の表1は、誘導体重量損失または1分あたりの重量損失パーセントを示す。
アルミニウムパンに約0.5gの水性ポリマー溶液(50重量%、固体)を入れ、それに2gの純粋を加えて薄膜を得た。パンを150℃にて60分間加熱して、物質を完全に乾燥させ、次いで乾燥物質を200℃にて30分間加熱した。加熱後、パンをオーブンから除去し、最終生成物の色は以下のスケールに従って等級分けした:白色−0、黄褐色−1、淡褐色−2、茶色−3。以下の物質およびこの方法の試験結果を以下の表2に示す。
メタクリル酸のポリマー無水物への次亜リン酸テロマーの変換は、フーリエ変換赤外分光法(FTIR)によりモニターされ得る。可変温度Specac Golden Gate(商標)ダイヤモンド減衰全反射(ATR)装置(Specac Inc(USA)Cranston、RI)と、ThermoNicolet(商標)6700FTIR(Thermo Fisher Scientific Waltham、MA)分光計を使用してスペクトルを測定した。データ収集パラメーターは、4cm−1分解能、16スキャンHapp−Genzelアポディゼーションであり、ゼロ充填はなかった。ATR装置を所望の温度まで予熱し、次いで約600ダルトンにおいて次亜リン酸メタクリル酸テロマーの水溶液のフィルムをATR結晶上で成型した。スペクトルを経時的に継続して測定した。
Claims (10)
- 1,000〜20,000の範囲の重量平均分子量を有し、カルボン酸または塩基を有するメタクリル酸無水物の次亜リン酸(コ)テロマーを含むポリマー組成物であって、次亜リン酸が塩の形態であり得る、ポリマー組成物。
- 前記重量平均分子量が2,000〜15,000の範囲である、請求項1に記載のポリマー組成物。
- 前記メタクリル酸無水物の次亜リン酸(コ)テロマーは、ポリマー骨格の炭素原子に結合されるポリマー中に平均で少なくとも1つのリン原子を有する、請求項1に記載のポリマー組成物。
- 前記メタクリル酸無水物の次亜リン酸(コ)テロマーは、i)酸性重合単位の総重量に基づいて、カルボン酸または塩基を保有する30〜80%の重合単位の平均、およびii)酸性重合単位の総重量に基づいて、20〜70%の無水物基の平均を有し、全てのパーセンテージはフーリエ変換赤外分光法(FTIR)により決定される、請求項1に記載のポリマー組成物。
- 前記メタクリル酸無水物の(コ)テロマーは、反応物の総重量に基づいて、2〜20重量%の次亜リン酸化合物またはその塩を含む、請求項1に記載のポリマー組成物。
- 前記メタクリル酸無水物の次亜リン酸塩を含有する(コ)テロマーは、メタクリル酸無水物の次亜リン酸塩を含有するホモテロマー、および追加のモノマーで作製されたメタクリル酸無水物の次亜リン酸コテロマーから選択される、請求項1に記載のポリマー組成物。
- 前記メタクリル酸無水物の次亜リン酸塩を含有する(コ)テロマーは、コテロマーを作製するために使用される次亜リン酸塩を含むモノマーおよび反応物の総重量に基づいて、90重量%またはそれ以上のメタクリル酸および次亜リン酸化合物から作製されたコテロマーである、請求項6に記載のポリマー組成物。
- 非水性担体中の粉末、ペレット、顆粒、または懸濁液の形態である、請求項1に記載のポリマー組成物。
- 175〜230℃の温度にてメタクリル酸の1つまたは複数の(コ)テロマーを乾燥させる工程を含む、メタクリル酸無水物の次亜リン酸(コ)テロマーを作製する方法。
- 前記乾燥させる工程は、噴霧乾燥後に、押出機、捏加機または捏加機リアクタ、流動床乾燥機、蒸発器、加熱混合器およびこれらのいずれかにおいて行われる、請求項9に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161558771P | 2011-11-11 | 2011-11-11 | |
US61/558,771 | 2011-11-11 | ||
PCT/US2012/063674 WO2013070581A1 (en) | 2011-11-11 | 2012-11-06 | Polymethacrylic acid anhydride telomers |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2014533317A true JP2014533317A (ja) | 2014-12-11 |
JP2014533317A5 JP2014533317A5 (ja) | 2017-02-23 |
JP6165756B2 JP6165756B2 (ja) | 2017-07-19 |
Family
ID=47178992
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014541152A Active JP6165756B2 (ja) | 2011-11-11 | 2012-11-06 | ポリメタクリル酸無水物テロマー |
Country Status (8)
Country | Link |
---|---|
US (1) | US9045575B2 (ja) |
EP (1) | EP2748214A1 (ja) |
JP (1) | JP6165756B2 (ja) |
KR (1) | KR101898466B1 (ja) |
CN (1) | CN104169315B (ja) |
BR (1) | BR112014010919A2 (ja) |
MX (1) | MX342237B (ja) |
WO (1) | WO2013070581A1 (ja) |
Cited By (1)
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US9499642B2 (en) | 2011-11-11 | 2016-11-22 | Rohm And Haas Company | Small particle size hypophosphite telomers of unsaturated carboxylic acids |
EP2876117B1 (en) | 2013-11-22 | 2019-12-25 | Rohm and Haas Company | (Meth)acrylic propene co-polymers and a method for their production |
US20180340045A1 (en) | 2014-12-22 | 2018-11-29 | Dow Global Technologies Llc | Polymethacrylic imide-acid polymers and methods of making and using |
EP3237462A1 (en) | 2014-12-22 | 2017-11-01 | Dow Global Technologies LLC | Amphiphilic comb polymers containing methacrylic anhydride |
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JP2017538827A (ja) * | 2014-12-22 | 2017-12-28 | ダウ グローバル テクノロジーズ エルエルシー | 誘導体化されたポリイミドならびに作製及び使用方法 |
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KR101898466B1 (ko) | 2018-09-13 |
WO2013070581A1 (en) | 2013-05-16 |
KR20140088875A (ko) | 2014-07-11 |
EP2748214A1 (en) | 2014-07-02 |
CN104169315B (zh) | 2017-03-22 |
JP6165756B2 (ja) | 2017-07-19 |
US9045575B2 (en) | 2015-06-02 |
MX2014005588A (es) | 2014-07-30 |
BR112014010919A2 (pt) | 2017-05-16 |
US20140323743A1 (en) | 2014-10-30 |
MX342237B (es) | 2016-09-21 |
CN104169315A (zh) | 2014-11-26 |
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