JP6199874B2 - 不飽和カルボン酸の小粒径次亜リン酸テロマー - Google Patents
不飽和カルボン酸の小粒径次亜リン酸テロマー Download PDFInfo
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- JP6199874B2 JP6199874B2 JP2014541165A JP2014541165A JP6199874B2 JP 6199874 B2 JP6199874 B2 JP 6199874B2 JP 2014541165 A JP2014541165 A JP 2014541165A JP 2014541165 A JP2014541165 A JP 2014541165A JP 6199874 B2 JP6199874 B2 JP 6199874B2
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- telomer
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- 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
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/24—Macromolecular compounds
- C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C04B24/2641—Polyacrylates; Polymethacrylates
- C04B24/2647—Polyacrylates; Polymethacrylates containing polyether side chains
-
- 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/08—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
- 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
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
- C08G81/025—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G containing polyether sequences
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
- C04B2103/30—Water reducers, plasticisers, air-entrainers, flow improvers
- C04B2103/32—Superplasticisers
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
- C04B2103/40—Surface-active agents, dispersants
- C04B2103/408—Dispersants
-
- 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
- C08F2500/00—Characteristics or properties of obtained polyolefins; Use thereof
- C08F2500/24—Polymer with special particle form or size
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
Description
MAAの次亜リン酸テロマーは、モノマーの総重量に基づいて、9.0重量%の次亜リン酸ナトリウム水和物を含む次亜リン酸ナトリウムの存在下で、水溶液中で重合させたメタクリル酸から形成した。
材料をエステル化させて櫛型ポリマーを作った。まず、重量平均分子量が約6000であるメタクリル酸の次亜リン酸テロマーを、150℃で2時間加熱し、水分を蒸発させ、実施例1として使用した。それから、オーブン乾燥させた次亜リン酸塩含有pMAAの一部を、200℃で30分加熱し、酸を無水物(pMAAn)に変換し、これを実施例2とした。また、過硫酸塩で開始させた、Mwが6,500であるpMAAを実施例3で用いた。3つの材料はすべて、乳鉢と乳棒を用いてすりつぶした後、さらにRetsch(ペンシルバニア州ニュータウン)MM400ボールミルを用いて30Hzで2分間粉砕した。粒径分析は、Beckman−Coulter(カリフォルニア州ブレア)のLS 13 320レーザー回折式粒径分析器(Beckman−Coulter、カリフォルニア州ブレア)を用いて、乾燥材料で行った。その結果生じた平均粒径サイズを以下の表1に示す。
実施例7および7Aの各ポリマーは、150℃で2時間加熱し、水分を蒸発させた。それから、乳棒と乳鉢を用いて、いずれも手で粉末化した。乾燥材料の粒径は、Beckman−Coulter LS 13 320レーザー回折式粒径分析器(Beckman−Coulter、カリフォルニア州ブレア)で評価および測定した。その結果を下の表4に示す。
下の表5に示すように、高流動化剤反応物の配合は、ポリエーテル側鎖を形成する反応物ならびに実施例7および7Aの乾燥ポリマーから成り、Mw2,000のポリ(エチレングリコール)メチルエーテル(mPEG2K)(Aldrich Chemicals、ミズーリ州セントルイス)ならびにmPEG 5,000ポリ(エチレングリコール)メチルエーテル(mPEG5K)(Aldrich Chemicals、ミズーリ州セントルイス)、p−トルエンスルホン酸一水和物(p−TSA、純度>98.5%、固体)(Aldrich)ならびに水酸化リチウム(純度>98%、固体)(Aldrich);Irganox(登録商標)5057安定剤(BASF、イリノイ州ヴァンダリア)を含んでいた。
Claims (10)
- 平均粒径が5.9μm〜215.2μmである、1つまたは複数の不飽和カルボン酸並びに1つまたは複数の不飽和カルボン酸無水物の酸化リンテロマーまたはコテロマー((コ)テロマー)の粒子または凝集体を含む組成物。
- 前記不飽和カルボン酸が、アクリル酸およびメタクリル酸から選択され、並びに不飽和カルボン酸無水物がメタクリル酸無水物である、請求項1に記載の組成物。
- 前記(コ)テロマーの重量平均分子量(Mw)が、1,000〜20,000である、請求項1〜2のうちいずれか一項に記載の組成物。
- 前記(コ)テロマーが、前記(コ)テロマーを作るために使われる反応物の総重量に基づいて、20〜99.2重量%のカルボン酸またはその塩基を有する重合単位の重合残基を含む、請求項1〜3のうちいずれか一項に記載の組成物。
- 前記(コ)テロマーが、前記(コ)テロマーにおける酸性重合単位の総重量に基づいて、少なくとも0.8重量%および最大70重量%のメタクリル酸無水物基を含む、請求項1〜4のうちいずれか一項に記載の組成物。
- 前記(コ)テロマーが、前記(コ)テロマーを作るために使われる反応物の総重量に基づいて、2〜20重量%のホスホン酸塩化合物、次亜リン酸塩化合物またはその塩を含む、請求項1〜5のうちいずれか一項に記載の組成物。
- 酸化リンテロマーを作るための方法であって:
酸化リン酸またはその塩化合物の存在下で、1つまたは複数の不飽和カルボン酸のモノマー混合物を水溶液付加重合する工程、その結果生じるコポリマーを120〜230℃の温度で乾燥させる工程、ならびにその粒径を小さくして、平均粒径が5.9μm〜215.2μmである、不飽和カルボン酸および不飽和カルボン酸から生じる無水物の(コ)テロマー粒子または凝集体を作る工程を含む方法。 - 前記乾燥させる工程が、噴霧乾燥、流動層乾燥、溶融押出成形、および噴霧乾燥に続く押出成形を含む、請求項7に記載の方法。
- 前記粒径を小さくする工程が、粉砕、製粉、摩砕、粉末状化、破砕または凍結粉砕を含む、請求項7または8に記載の方法。
- 前記方法が、さらに:
前記(コ)テロマー粒子または凝集体を、1つまたは複数のポリエーテルポリオール、アルキルポリエーテルポリオール、ポリエーテルアミンまたはアルキルポリエーテルアミンと、加熱して反応させ、櫛型ポリマーを形成する工程を含む、請求項7〜9のうちいずれか一項に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161558802P | 2011-11-11 | 2011-11-11 | |
US61/558,802 | 2011-11-11 | ||
US13/644,600 | 2012-10-04 | ||
US13/644,600 US9499642B2 (en) | 2011-11-11 | 2012-10-04 | Small particle size hypophosphite telomers of unsaturated carboxylic acids |
PCT/US2012/063774 WO2013070644A1 (en) | 2011-11-11 | 2012-11-07 | Small particle size hypophosphite telomers of unsaturated carboxylic acids |
Publications (3)
Publication Number | Publication Date |
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JP2014533318A JP2014533318A (ja) | 2014-12-11 |
JP2014533318A5 JP2014533318A5 (ja) | 2016-12-08 |
JP6199874B2 true JP6199874B2 (ja) | 2017-09-20 |
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JP2014541165A Active JP6199874B2 (ja) | 2011-11-11 | 2012-11-07 | 不飽和カルボン酸の小粒径次亜リン酸テロマー |
JP2014541167A Pending JP2014533319A (ja) | 2011-11-11 | 2012-11-07 | メタクリル酸またはその無水物の小粒径テロマー |
JP2017162285A Active JP6480992B2 (ja) | 2011-11-11 | 2017-08-25 | メタクリル酸またはその無水物の小粒径テロマー |
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JP2014541167A Pending JP2014533319A (ja) | 2011-11-11 | 2012-11-07 | メタクリル酸またはその無水物の小粒径テロマー |
JP2017162285A Active JP6480992B2 (ja) | 2011-11-11 | 2017-08-25 | メタクリル酸またはその無水物の小粒径テロマー |
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US (2) | US9365657B2 (ja) |
EP (2) | EP2748213B1 (ja) |
JP (3) | JP6199874B2 (ja) |
KR (2) | KR101942775B1 (ja) |
CN (2) | CN103930453B (ja) |
BR (2) | BR112014010920A2 (ja) |
MX (2) | MX347061B (ja) |
WO (2) | WO2013070644A1 (ja) |
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EP2778183B1 (en) * | 2013-03-15 | 2015-04-29 | Rohm and Haas Company | Polymethacrylic acid anhydride telomers |
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CN101747885B (zh) * | 2008-12-15 | 2013-05-15 | 安徽天润化学工业股份有限公司 | 一种高分子量抗盐聚合物驱油剂的制备方法 |
US20120301686A1 (en) * | 2009-12-03 | 2012-11-29 | Yvonne Wilhelmina Smak | Polymer, process and composition |
WO2011131526A1 (de) * | 2010-04-19 | 2011-10-27 | Basf Se | Verfahren zur herstellung wasserabsorbierender polymerpartikel |
KR101898466B1 (ko) | 2011-11-11 | 2018-09-13 | 롬 앤드 하스 캄파니 | 폴리메타크릴산 무수물 텔로머 |
US9365657B2 (en) * | 2011-11-11 | 2016-06-14 | Rohm And Haas Company | Small particle size telomers of methacrylic acid or anhydride |
CN102532558A (zh) * | 2011-12-29 | 2012-07-04 | 上海三瑞高分子材料有限公司 | 一种酰胺型聚羧酸系减水剂的制备方法 |
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JP2018035351A (ja) | 2018-03-08 |
WO2013070652A1 (en) | 2013-05-16 |
MX347794B (es) | 2017-05-10 |
EP2748213B1 (en) | 2019-09-25 |
JP2014533319A (ja) | 2014-12-11 |
BR112014010920A2 (pt) | 2017-05-16 |
EP2748213A1 (en) | 2014-07-02 |
KR101942775B1 (ko) | 2019-01-28 |
CN103930454B (zh) | 2017-05-24 |
MX347061B (es) | 2017-04-10 |
EP2748212B1 (en) | 2019-09-25 |
JP2014533318A (ja) | 2014-12-11 |
KR20140088876A (ko) | 2014-07-11 |
CN103930453A (zh) | 2014-07-16 |
US9365657B2 (en) | 2016-06-14 |
KR101942777B1 (ko) | 2019-01-28 |
MX2014005586A (es) | 2014-07-30 |
JP6480992B2 (ja) | 2019-03-13 |
BR112014010918B1 (pt) | 2020-12-15 |
US20130122299A1 (en) | 2013-05-16 |
CN103930454A (zh) | 2014-07-16 |
EP2748212A1 (en) | 2014-07-02 |
MX2014005587A (es) | 2014-07-30 |
US9499642B2 (en) | 2016-11-22 |
US20130123436A1 (en) | 2013-05-16 |
WO2013070644A1 (en) | 2013-05-16 |
CN103930453B (zh) | 2016-12-21 |
BR112014010918A2 (pt) | 2017-05-16 |
KR20140088877A (ko) | 2014-07-11 |
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