JP6702953B2 - 表面効果組成物のための非フッ素化モノマー及び非フッ素化ポリマー - Google Patents
表面効果組成物のための非フッ素化モノマー及び非フッ素化ポリマー Download PDFInfo
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- JP6702953B2 JP6702953B2 JP2017516730A JP2017516730A JP6702953B2 JP 6702953 B2 JP6702953 B2 JP 6702953B2 JP 2017516730 A JP2017516730 A JP 2017516730A JP 2017516730 A JP2017516730 A JP 2017516730A JP 6702953 B2 JP6702953 B2 JP 6702953B2
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- 235000016709 nutrition Nutrition 0.000 description 1
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- 229920001778 nylon Polymers 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 125000006353 oxyethylene group Chemical group 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- HSNZZMHEPUFJNZ-SHUUEZRQSA-N sedoheptulose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO HSNZZMHEPUFJNZ-SHUUEZRQSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
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- 229920000428 triblock copolymer Polymers 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/20—Oxygen atoms
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- 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
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- C08F120/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F120/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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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
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- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
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- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
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- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/227—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated
- D06M15/233—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of hydrocarbons, or reaction products thereof, e.g. afterhalogenated or sulfochlorinated aromatic, e.g. styrene
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- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
- D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
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- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
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- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
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Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Engineering & Computer Science (AREA)
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- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Emergency Medicine (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Furan Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Description
CH2=C(R9)C(O)Q(CH2)q(CHR9)iNR10R11 (VIa)
CH2=C(R9)NR12R13 (VIb)
又はこれらの混合物を使用し、式中、R9は、独立的に、H又はCH3から選択され;R10及びR11は、それぞれ独立的に、C1〜C4アルキル、ヒドロキシエチル、又はベンジルであるか;又はR10及びR11は、窒素原子と共に、モルホリン環、ピロリジン環、又はピペリジン環を形成し;R12及びR13は、それぞれ独立的に、H又はC1〜C4アルキルから選択され;Qは、−O−又は−NR14−であり、R14は、H又はC1〜C4アルキルであり;iは、0〜4であり、qは、1〜4であり、このとき、R10及びR11に結合する窒素は、約0%〜100%が塩化していてもよく、四級化していてもよく、又はアミンオキシドとして存在していてもよい。この実施形態のコポリマーは、当業者に知られている任意の手段によって合成することができる。コポリマーは、任意選択的に、当業者に知られている従来の技術によって、部分的又は完全に塩化又は四級化していてもよい。一態様において、塩化又は四級化の程度は、約50%〜約100%である。好ましくは、モノマーを溶媒系(例えば、イソプロピルアルコール及びメチルイソブチルケトン)中で合わせ、この混合物を、開始剤の活性化温度まで加熱し、モノマー混合物に開始剤をゆっくりと入れ、共重合を進行させることによってコポリマーを合成する。次いで、ポリマー混合物を水性塩化溶液(例えば、酢酸溶液)と接触させてもよく、有機溶媒を、好ましくは蒸留によって除去する。最終生成物は、水性エマルションである。
全ての溶媒及び試薬は、特に指示がない限り、Sigma−Aldrich(St.Louis,MO)から購入し、供給された状態のまま使用した。メチルイソブチルケトン(MIBK)及びポリ(エチレングリコール)メタクリレートMW=360(7−EOメタクリレート)は、両方ともSigma−Aldrich(St.Louis,MO)から入手可能である。
この試験で処理した布地は、SDL Atlas Textile Testing Solutions(Rock Hill,South Carolina 29732)から入手可能な100重量%のカーキ色の綿ツイル、及びL.Michael OY(Finland)から入手可能な100重量%の赤色ポリエステル布地であった。従来のパッド浴(浸漬)プロセスを用い、種々のエマルションポリマーの水性分散物を用い、布地を処理した。調製した濃い分散物を脱イオン水で希釈し、浴中に60g/L又は100g/Lの生成物を含むパッド浴を得た。綿布地の処理には、湿潤剤INVADINE PBN及び触媒添加した架橋剤KNITTEX 7636(全てHuntsman(Salt Lake City,UT)から入手可能)も、それぞれ5g/L及び30g/Lで浴中に入れた。布地を浴中でパディングし、過剰の液体を圧搾ローラーによって除去した。含浸量は、綿基材に対して約95%であった。「含浸量」とは、布地の乾燥重量に基づく、布地に塗布されたエマルジョンポリマー及び添加剤の浴溶液の重量である。
処理済み基材の撥水性を、デュポン(DuPont)実験室用方法に従って、テフロングローバル仕様及び品質管理試験情報パケット(Teflon Global Specifications and Quality Control Tests information packet)に概説されるように測定した。試験は、水性液体による濡れに対する、処理済み基材の耐性を測定する。様々な表面張力の水・アルコール混合物の滴を布地の上に置き、表面の濡れの広がりを目視で測定する。本試験は、水性汚れ防止性の目安を提供する。撥水性評点が高いほど耐性は良好であり、仕上げられた基材は、水系物質によって着色される。標準試験液の組成を下表1に示す。試験液がぎりぎり合格することに関して、表1の数値から1/2を引くことによって、0.5の増分の評点が決定される。
処理した布地サンプルについて、AATCC標準試験法118の改変法によって、撥油性を試験し、試験は以下のように行った。布地サンプルをポリマーの水性分散物で処理し、これを試験前に23℃+相対湿度65%で最低15時間かけ、平衡状態にした。次いで、以下の表2で特定する一連の有機液を布地サンプルに滴下した。最も小さな番号の試験液(撥液性の評点1)から初め、1滴(直径約5mm又は体積0.05mL)を、少なくとも5mm離れた3箇所それぞれに置いた。この液滴を30秒間観察した。この期間の終わりに、3滴のうち2滴が、まだ球形のままであり、液滴の周囲にウィッキングが存在しない場合、次に大きな番号の液体を3滴、隣接部位に置き、同様に30秒間観察した。いずれかの試験液が、3滴のうち2滴で球形から半球形を保つことができないか、又は濡れ現象若しくはウィッキングが起こるまで、この手順を続けた。
処理済み基材の動的撥水性を、繊維化学染色協会(American Association of Textile Chemists and Colorists)(AATCC)TM−22に従って測定した。サンプルを、公開基準を参照して目視で採点し、100の評点は、水の浸透又は表面付着がないことを示す。評点90は、浸透がなく、ランダムな貼り付き又は濡れ現象がわずかにあることを示す。値が低いほど、濡れ現象及び浸透が多くなることを示す。試験方法2の動的撥水性試験は、要件の厳しい現実的な撥水性の試験である。
本試験は、家庭での洗濯中に、油っぽい汚れを除去する布地の能力を測定する。
未処理の布地サンプルを、上の試験方法に従って試験した。綿布地及びポリエステル布地は、両方とも水滴下の評点が0であり、油滴下の評点が0であり、スプレーの評点が0であった。
CH2=C(CH3)−C(O)−STS、ここで、STSは、ソルビタントリステアレートの残基である。
乾燥した1L丸底4ッ口フラスコに、熱電対、メカニカルスターラー、窒素投入口、凝縮器、及び気体出口を取り付けた。このフラスコに、ソルビタントリステアレート(100g、OH値76、162.57mmol)、ジクロロメタン(300g)、及びトリエチルアミン(17.82g、176.11mmol)を投入した。この溶液に、シリンジによって塩化メタクリロイル(15.79mL、162.57mmol)をゆっくりと加えた。このフラスコを箔で絶縁した。反応混合物を窒素下、室温で48時間攪拌し、その時点で200mLのエーテルを加えた。トリエチルアンモニウムクロリドを濾過によって除去した。有機層を5重量%の酢酸溶液(250mL)で洗浄し、水層をジクロロメタンで抽出し、有機層を飽和NaHCO3溶液で洗浄した。有機層をMgSO4で乾燥させ、濾過した。0.01gのp−メトキシフェノール重合開始剤を加え、ロータリーエバポレーションによって、加熱することなく有機溶媒を除去した。生成物は、室温で淡黄色固体であった。
CH2=C(CH3)−C(O)OCH2CH2NHC(O)−STS、ここで、STSは、ソルビタントリステアレートの残基である。
乾燥した4ッ口の500mL丸底フラスコに、熱電対、メカニカルスターラー、窒素投入口、凝縮器、及び気体出口を取り付けた。このフラスコに、2−イソシアナトエチルメタクリレート(25.0g、161.13mmol)、MIBK(141.44g)、及び0.50重量% FeCl3のMIBK溶液(2.5g)を投入した。この混合物を60℃まで加熱し、このフラスコにソルビタントリステアレート(118.94g、OH値76)を加えた。次いで、温度を80℃まで上げ、一晩攪拌した。24時間後、1,8−ジアザビシクロウンデカ−7−エン(0.05g)を加え、反応混合物を80℃でさらに24時間攪拌した。試験した溶液がイソシアネートに不活性である場合、これをミルクフィルタで濾過し、集めた。
CH2=CH−(C6H4)−C(CH3)2−NHC(O)−STS、ここで、STSは、ソルビタントリステアレートの残基である。
乾燥した4ッ口の500mL丸底フラスコに、熱電対、メカニカルスターラー、窒素投入口、凝縮器、及び気体出口を取り付けた。このフラスコに、3−イソプロペニル−α,α−ジメチルベンジルイソシアネート(36.0g、178.8mmol)、MIBK(168g)、0.50重量% FeCl3のMIBK溶液(6.0g)、及び1,8−ジアザビシクロウンデカ−7−エン(0.1g)を投入した。混合物を60℃まで加熱した。このフラスコにソルビタントリステアレート(132.04g、178.8mmol)を加えた。次いで、温度を80℃まで上げ、一晩攪拌した。試験した溶液がイソシアネートに不活性である場合、45℃まで冷却し、ミルクフィルタで濾過し、集めた。
CH2=C(CH3)−C(O)−STO、ここで、STOは、ソルビタントリオレエートの残基である。
乾燥した250gの丸底フラスコに、ソルビタントリオレエート(50.0g、0.0522mol)、ジクロロメタン(50mL)、及びトリエチルアミン(14.6mL)を投入した。混合物を氷浴で0℃まで冷却した。この溶液に塩化メタクリロイル(5.1mL、0.0522mol)をゆっくりと加え、反応混合物を窒素下、室温で一晩攪拌した。次いで、第2の塩化メタクリロイル(5.1mL、0.0522mol)を加え、反応混合物を室温でさらに24時間攪拌し、水(100mL)を加えた。層分離させ、水層をジクロロメタンで抽出した。合わせた有機層を飽和Na2CO3及び水で洗浄し、MgSO4で乾燥させ、濾過し、濃縮した。
4ッ口の500mL丸底フラスコに、ガラス栓、熱電対、メカニカルスターラー、窒素投入口、凝縮器、及び気体出口を取り付けた。このフラスコに、表3のモノマーとMIBKを投入した(モノマーを約50重量%まで希釈するため)。この溶液に窒素を10分間流し、60℃まで加熱した。VAZO 67開始剤を加え、反応混合物を70℃まで加熱し、一晩攪拌した。
4ッ口の500mL丸底フラスコに、滴下漏斗、熱電対、メカニカルスターラー、窒素投入口、凝縮器、及び気体出口を取り付けた。このフラスコに、ソルビタントリオレエートメタクリレート(53.5g、30重量%)及び125gのMIBKを投入した。この溶液に窒素を10分間流し、65℃まで加熱した。この溶液にVAZO 67(3.2g)を加え、反応混合物を80℃まで加熱し、一晩攪拌した。
ソルビタントリステアレート25.0gを用いたスケールで、ソルビタントリステアレートウレタンメタクリレートを上述のように調製した。反応が終了した直後に、反応混合物を60℃まで冷却し、0.90gのVAZO 67を加えた。反応物を80℃で一晩攪拌した。温かいDI水(114g)、ARMEEN 18D(1.49g)、TERGITOL TMN−10(1.14g)、酢酸(1.12g)、及びトリプロピレングリコール(14.6g)をこの混合物に加え、70℃で30分間攪拌した。30分後、混合物を音波処理した。蒸留によってMIBKを除去し、生成物をソックフィルタ−によって濾過し、固形分が20.0%になるまで希釈した。分散物を、パッド浴200gあたりポリマー3.6gに相当する固形分20%、90g/Lで布地サンプルに塗布し、上の試験方法に従って試験した。
異なる界面活性剤系を使用した以外は、ソルビタントリステアレート62.43gを用いたスケールで実施例12を繰り返した。温かいDI水(284g)、ARMEEN 18D(2.82g)、ジアセチン(13.76g)、酢酸(1.76g)、STEPOSOL SB−W(1.06g)、及びBRIJ L4(1.41g)をこの混合物に加え、70℃で30分間攪拌した。30分後、混合物を41MPa(6000psi)で4回均質化した。蒸留によってMIBKを除去し、生成物をソックフィルタ−によって濾過し、固形分が20.0%になるまで希釈した。分散物を、パッド浴200gあたりポリマー3.6gに相当する固形分20%、90g/Lで布地サンプルに塗布し、上の試験方法に従って試験した。
反応混合物を80℃で一晩加熱したこと、パッド浴にPHOBOL XANを用いなかったことを除き、表6に列挙した試薬を用い、35重量%のモノマー、30重量%のMIBK、35重量%のイソプロピルアルコール共溶媒を用いて、実施例5を繰り返した。
表7に列挙した試薬を用いて施例14を繰り返した。
7−EOメタクリレート、N−イソ−ブトキシメチルメタアクリルアミド、ヒドロキシエチルメタクリレート、及びドデシルメルカプタンのストック溶液を、表8の量に従って、MIBK中、50重量%で調製した。30mLバイアル中、さらなるモノマーとMIBKをストック溶液及び開始剤と合わせた。バイアルに蓋をし、窒素ラインを接続した。ほとんどの反応をMIBK中、固形分25〜40%で行う。反応物を一晩かけて80℃まで加熱した。塩化ビニリデンが存在した場合、反応混合物を50℃まで加熱し、その後、温度をゆっくりと80℃まで上げ(15分ごとに10℃ずつ)、一晩攪拌した。試料をMIBKで固形分10%になるまで希釈し、布地に塗布し、上の試験方法に従って試験した。
表9に列挙した量に従って、30mLバイアルにモノマーと開始剤を加えた。バイアルに蓋をし、窒素ラインを接続した。反応混合物を80℃まで加熱し、一晩攪拌した。試料をMIBKで固形分10%になるまで希釈し、布地に塗布し、上の試験方法に従って試験した。
表10の試薬を用いて実施例27を繰り返した。
表11の試薬を用いて実施例27を繰り返した。
表12に列挙した試薬を用いて実施例27を繰り返した。
500mLの4ッ口丸底フラスコに、熱電対、メカニカルスターラー、窒素投入口、凝縮器、及び気体出口を取り付けた。このフラスコに、表14のモノマー、MIBK(25〜40重量%溶液を調製するためのもの)、tert−ブチルアルコール(44.17g)を投入した。実施例44の場合、MIBKを使用せず、tert−ブチルアルコールは85.73gであった。混合物を80℃で加熱し、VAZO 67(0.19g)を加えた。反応物を一晩攪拌した。次いで、別のVAZO 67(0.19g)を加え、反応物を80℃で一晩攪拌した。このフラスコに温かい(65℃)DI水及びクロロ酢酸ナトリウム(11.17g)を加え、混合物を82℃で2.5時間攪拌した。次いで、有機溶媒をロータリーエバポレーションによって除去した。生成物をソックフィルタ−によって濾過し、固形分が20%になるまで希釈した。分散物を、パッド浴200gあたりポリマー3.6gに相当する固形分20%、90g/Lで布地サンプルに塗布し、上の試験方法に従って試験した。
Claims (11)
- 式(I)の化合物であって、
R3は、H又はC1〜C4アルキル基から選択され;
Yは、O、置換アリーレン基、又は非置換アリーレン基から選択され;
Aは、直鎖又は分岐鎖のC1〜C10アルキレン基であり;
wは、0又は1であり;
vは、0又は1であり;
yは、1であり;
w+yは、1又は2であり;wが0の場合、Yは、置換又は非置換のアリーレン基であり;YがOの場合、vが1であることを条件とし;
Xは、式(IIa)、(IIb)、又は(IIc)から選択され:
XXは、水素原子またはROCH 2 (CHOR) p −であり、
各nは、独立的に、0〜20であり;
各mは、独立的に、0〜20であり;
m+nは、0よりも大きく;
各R1は、独立的に、任意選択的に少なくとも1つの不飽和結合を含んでもよい9〜29個の炭素を有する直鎖又は分岐鎖のアルキル基であり;
各R2は、独立的に、−H、任意選択的に少なくとも1つの不飽和結合を含んでもよい6〜30個の炭素を有する直鎖又は分岐鎖のアルキル基、又はこれらの混合物であり、 rは、1〜3であり;
pは、独立的に、0〜2から選択され;
rが3のとき、XXは水素原子であることを条件とし;
但し、Xが式(IIa)である場合、1つのRは、式(I)のC=Oに対する直接結合であり;少なくとも1つのRは、−R 1 、−C(O)R 1 、−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 、又は−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 であり;
各R 4 は、独立して、式(I)のC=Oに対する直接結合、−H、任意選択的に少なくとも1つの不飽和結合を含んでもよい6〜30個の炭素を有する直鎖若しくは分岐鎖のアルキル基、又はこれらの組み合わせ、−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 、あるいは−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 であり;
Xが式(IIb)である場合、1つのR又はR 4 は、式(I)のC=Oに対する直接結合であり;少なくとも1つのR又はR 4 は、任意選択的に少なくとも1つの不飽和結合を含んでもよい直鎖若しくは分岐鎖のアルキル基、又はこれらの組み合わせ、−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 、あるいは−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 であることを条件とし;
各R 19 は、式(I)のC=Oに対する直接結合、−H、−C(O)R 1 、又は−CH 2 C[CH 2 OR] 3 であり、
Xが式(IIc)である場合、1つのR 19 又はRは、式(I)のC=Oに対する直接結合であり;少なくとも1つのR 19 又はRは、−C(O)R 1 、−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 、又は−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 であることを条件とする、
化合物。 - Xが式(IIb)から選択される、請求項1に記載の化合物。
- (a)式(III)から選択される化合物:
式中、Yは、O、置換アリーレン基、又は非置換アリーレン基から選択され;
Aは、直鎖又は分岐鎖のC1〜C10アルキレン基であり;
R3は、H又はC1〜C4アルキル基から選択され;
wは、0又は1であり;
vは、0又は1であり;
yは、1であり;
Zは−NCOであり;
w+yは、1又は2であり;wが0の場合、Yは、置換又は非置換のアリーレン基であり;YがOの場合、vが1であることを条件とし;
XXは、水素原子またはR 5 OCH 2 (CHOR 5 ) p −であり、
各nは、独立的に、0〜20であり;
各mは、独立的に、0〜20であり;
m+nは、0よりも大きく;
各R1は、独立的に、任意選択的に少なくとも1つの不飽和結合を含んでもよい9〜29個の炭素を有する直鎖又は分岐鎖のアルキル基であり;
各R2は、独立的に、−H、任意選択的に少なくとも1つの不飽和結合を含んでもよい6〜30個の炭素を有する直鎖若しくは分岐鎖のアルキル基、又はこれらの混合物であり、
rは、1〜3であり;
pは、独立的に、0〜2から選択され;
rが3のとき、XXは水素原子であることを条件とし;
式(IVa)の化合物が使用される場合、少なくとも1つのR 5 は、−R 1 、−C(O)R 1 、−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 、又は−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 であることを条件とし;
各R 6 は、独立的に、−H、任意選択的に少なくとも1つの不飽和結合を含んでもよい10〜30個の炭素を有する直鎖若しくは分岐鎖のアルキル基、又はこれらの組み合わせ、−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 、あるいは−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 であり;
式(IVb)の化合物が使用される場合、少なくとも1つのR 5 又はR 6 は、任意選択的に少なくとも1つの不飽和結合を含んでもよい直鎖若しくは分岐鎖のアルキル基、又はこれらの組み合わせ、−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 、あるいは−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 であることを条件とし;
各R 7 は、−H、−C(O)R 1 、又は−CH 2 C[CH 2 OR 5 ] 3 であり、
式(IVc)の化合物が使用される場合、少なくとも1つのR 7 又はR 5 は、−C(O)R 1 、−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 、又は−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 であるとこを条件とする、
方法。 - ポリマー化合物であって、式(V)の繰り返し単位を含み:
R3は、H又はC1〜C4アルキル基から選択され;
xは、1〜200の整数であり;
Yは、O、置換アリーレン基、又は非置換アリーレン基から選択され;
Aは、直鎖又は分岐鎖のC1〜C10アルキレン基であり;
wは、0又は1であり;
vは、0又は1であり;
yは、1であり;
w+yは、少なくとも1であり;wが0の場合、Yは、置換又は非置換のアリーレン基であり;YがOの場合、vが1であることを条件とし;
Xは、式(IIa)、(IIb)、又は(IIc)から選択され:
XXは、水素原子またはROCH 2 (CHOR) p −であり、
各nは、独立的に、0〜20であり;
各mは、独立的に、0〜20であり;
m+nは、0よりも大きく;
各R1は、独立的に、任意選択的に少なくとも1つの不飽和結合を含んでもよい9〜29個の炭素を有する直鎖又は分岐鎖のアルキル基であり;
各R2は、独立的に、−H、任意選択的に少なくとも1つの不飽和結合を含んでもよい6〜30個の炭素を有する直鎖若しくは分岐鎖のアルキル基、又はこれらの混合物であり、
rは、1〜3であり;
pは、独立的に、0〜2から選択され;
rが3のとき、XXは水素原子であることを条件とし;
但し、Xが式(IIa)である場合、1つのRは、式(I)のC=Oに対する直接結合であり;少なくとも1つのRは、−R 1 、−C(O)R 1 、−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 、又は−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 であり;
各R 4 は、独立して、式(I)のC=Oに対する直接結合、−H、任意選択的に少なくとも1つの不飽和結合を含んでもよい6〜30個の炭素を有する直鎖若しくは分岐鎖のアルキル基、又はこれらの組み合わせ、−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 、あるいは−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 であり;
Xが式(IIb)である場合、1つのR又はR 4 は、式(I)のC=Oに対する直接結合であり;少なくとも1つのR又はR 4 は、任意選択的に少なくとも1つの不飽和結合を含んでもよい直鎖若しくは分岐鎖のアルキル基、又はこれらの組み合わせ、−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 、あるいは−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 であることを条件とし;
各R 19 は、式(I)のC=Oに対する直接結合、−H、−C(O)R 1 、又は−CH 2 C[CH 2 OR] 3 であり、
Xが式(IIc)である場合、1つのR 19 又はRは、式(I)のC=Oに対する直接結合であり;少なくとも1つのR 19 又はRは、−C(O)R 1 、−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m R 2 、又は−(CH 2 CH 2 O) n (CH(CH 3 )CH 2 O) m C(O)R 1 であることを条件とする、
ポリマー化合物。 - 直鎖若しくは分岐鎖の炭化水素、直鎖若しくは分岐鎖のフルオロカーボン、エーテル、アルコール、無水物、オキシアルキレン、エステル、ホルメート、カルボン酸、カルバメート、ウレア、アミン、アミド、スルホネート、スルホン酸、スルホンアミド、ハロゲン化物、飽和若しくは不飽和の環状炭化水素、モルホリン、ピロリジン、ピペリジン、又はこれらの混合物から選択される官能基を有するエチレン性不飽和モノマーに由来する少なくとも1つの繰り返し単位をさらに含む、請求項6に記載のポリマー化合物。
- 直鎖又は分岐鎖のアルキル(メタ)アクリレート、アミノ(メタ)アクリレート及びジアミノ(メタ)アクリレート、任意選択的にO、CH2、CH2CH2、又はSO2NHによって中断されてもよい直鎖又は分岐鎖のフルオロアルキル(メタ)アクリレート、アルコキシル化(メタ)アクリレート、(メタ)アクリル酸、塩化ビニル又は塩化ビニリデン、グリシジル(メタ)アクリレート、酢酸ビニル、ヒドロキシアルキレン(メタ)アクリレート、ウレタン又はウレア(メタ)アクリレート、N−メチロイル(メタ)アクリルアミド、アルコキシアルキル(メタ)アクリルアミドを含む(メタ)アクリルアミド、スチレン、α−メチルスチレン、クロロメチル−置換スチレン、エチレンジオールジ(メタ)アクリレート、2−アクリルアミド−2−メチル−1−プロパンスルホン酸(AMPS)、及び無水マレイン酸から選択されるエチレン性不飽和モノマーに由来する少なくとも1つの繰り返し単位をさらに含む、請求項6に記載のポリマー化合物。
- 請求項6に記載のポリマー化合物を基材表面に塗布することを含む、繊維基材を処理する方法。
- 請求項10に記載の方法に従って処理される基材。
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CN107001304B (zh) | 2021-04-30 |
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KR102470190B1 (ko) | 2022-11-24 |
JP2020143291A (ja) | 2020-09-10 |
US9915025B2 (en) | 2018-03-13 |
WO2016048642A1 (en) | 2016-03-31 |
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