JP2016135589A - 水溶解性または水崩壊性の共重合体 - Google Patents
水溶解性または水崩壊性の共重合体 Download PDFInfo
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- JP2016135589A JP2016135589A JP2015246849A JP2015246849A JP2016135589A JP 2016135589 A JP2016135589 A JP 2016135589A JP 2015246849 A JP2015246849 A JP 2015246849A JP 2015246849 A JP2015246849 A JP 2015246849A JP 2016135589 A JP2016135589 A JP 2016135589A
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- copolymer
- weight
- impact modifier
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- unsaturated monocarboxylic
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- VXASQTMYWZHWMX-UHFFFAOYSA-N 4-ethoxybutyl 2-methylprop-2-enoate Chemical compound CCOCCCCOC(=O)C(C)=C VXASQTMYWZHWMX-UHFFFAOYSA-N 0.000 description 1
- RWHRFHQRVDUPIK-UHFFFAOYSA-N 50867-57-7 Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O RWHRFHQRVDUPIK-UHFFFAOYSA-N 0.000 description 1
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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
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/02—Homopolymers or copolymers of acids; Metal 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
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
-
- 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
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
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)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
【解決手段】α−β−不飽和モノカルボン酸、好ましくはアクリル酸に基づいた共重合体であって、モル質量(M)<100000g/モルを持つ共重合体。モル質量Mが25000〜90000g/モル、好ましくは30000〜85000g/モル、特に好ましくは35000〜75000g/モルである共重合体。α−β−不飽和モノカルボン酸が共重合の全重量に対し、60〜95重量%、好ましくは70〜90重量%、特に好ましくは75−85重量%含有する共重体。
【選択図】なし
Description
で規定される。
である。
ここでNiは、試料中の正確に繰り返し単位iを持ちかつモル質量Miを持つポリマー分子またはポリマーの数である。
ガラス温度計、らせんコイル凝縮器、及び攪拌器を備えた2リットルの容量を持つ三口フラスコが、温浴内に置かれた。フラスコは、次いで200gのエタノール、40gのアクリル酸ブチル、160gのアクリル酸、及び1.5gのα−メチルスチレン二量体を充填された。温浴は約83℃の温度に設定され、攪拌器は160回転/分の速度に設定された。約77℃の材料温度で、3gのPerkadox LB 75(開始剤)が添加された。材料の温度は、続く30分で83℃の最大値に上昇し、その後、それは77℃の温度に低下した。4時間後、重合は終わった。溶剤は100℃で減圧オーブン内で蒸発された。得られた試料は、次いで約220℃のオーブン内で半時間の間、乾燥された。この方法で製造された共重合体の持つ性質は以下の通りであった:
遊離カルボキシル基の分率:40.8%(共重合体の全重量に基づいて)
M:46000g/モル
Mn:17000g/モル
Tg:108°C
220°Cで60rpmでの15分後のBrabenderトルク:580kpm(キロポンドメーター)
200°C/5kgでのメルトインデックス:8.3g/10分
表1中の記号の意味:
PAAm: ポリアクリルアミド
PAA: ポリアクリル酸
PMAA: ポリメタクリル酸
Tg: ガラス転移温度
表1は、従来技術から既知の水溶解性アクリル酸系重合体がそれらの加工温度で不安定であるという欠点を持つことを示す。対照的に、本発明の共重合体の特別な利点は、それらが問題なしに熱可塑的に加工させることができること、さらに水溶解性であることまたはいかなる場合でも水中で崩壊可能であることである(これに関しては、以下の表2及び3も参照されたい)。
表2中の記号の意味:
S: 水膨潤可能または水による洗浄で除去可能
SC: 透明溶液
I: 溶解不可
MEA: アクリル酸メトキシエチル
BA: アクリル酸ブチル
AA: アクリル酸
MA: アクリル酸メチル
BMA: メタクリル酸ブチル
IBMA: メタクリル酸イソブチル
EMA: メタクリル酸エチル
MMA: メタクリル酸メチル
PAA: ポリアクリル酸
PMAA: ポリメタクリル酸
Tg: ガラス転移温度
表2に記載された結果は、第一に、本発明の共重合体(共重合体1〜7)が大部分は水溶解性であるか、または少なくとも水膨潤可能もしくは水での洗浄により除去可能であることを示す。第二に、その結果はまた、本発明の共重合体がそれらの分解温度より十分に低いガラス転移温度で顕著であり、それにより例えば押出適性のような熱可塑性加工性を改善し、または実際にこの加工性を可能にする。特に、大多数に基づいて、本発明の共重合体は、通常の単独アクリル系重合体(単独重合体8及び9)のガラス転移温度より低いガラス転移温度で顕著であり、それによりこれらの単独アクリル酸系重合体と比べたときのそれらの熱可塑性加工性を明確に改善する。
表3中の記号の意味:
S 溶解可能
R 迅速に溶解可能
C 溶液透明
T わずかに濁った溶液
Tp 部分的に溶解
Tg: ガラス転移温度
Mw: モル質量
Mn: 数平均モル質量
d: モル質量分布の幅
RT: 室温
MFI: メルトフローインデックス
上の表3の遊離カルボキシル基の百分率分率は、共重合体の全重量に関する。
本発明の共重合体のモル質量は、ゲル浸透クロマトグラフィー(GPC)により決定され、THPの溶液中の共重合体の溶離容積は、THFの溶液中の参照標準重合体の溶離容積と比較されている。使用されたクロマトグラフィーのカラムは、ShodexからのGPCカラムであり、Kontron HPLC UV検出器430が使用された(標準::PSS Ready Cal.Standards、Polymer Standards Service,Mainzからの高分子、モレキュラーシーブ Union Carbide type 4A,evaluation PSS Win−GPC)。
Claims (16)
- α−β−不飽和モノカルボン酸、好ましくはアクリル酸に基づく共重合体において、共重合体がモル質量<100000g/モルを持つことを特徴とする共重合体。
- モル質量が25000g/モル〜90000g/モル、特に30000g/モル〜85000g/モル、好ましくは35000g/モル〜75000g/モルであることを特徴とする請求項1に記載の共重合体。
- α−β−不飽和モノカルボン酸が、共重合体の全重量に基づいて、60重量%〜95重量%、特に70重量%〜90重量%、好ましくは75重量%〜85重量%の重量分率を持つことを特徴とする請求項1または2に記載の共重合体。
- 共重合体が、α−β−不飽和モノカルボン酸に加えて、共単量体としてα−β−不飽和モノカルボン酸のエステル、特にアルキルエステル及び/またはアルコキシアルキルエステルを持つことを特徴とする請求項1〜3のいずれかに記載の共重合体。
- α−β−不飽和モノカルボン酸のエステルが、アクリル酸メチル、アクリル酸エチル、アクリル酸n−ブチル、アクリル酸イソブチル、アクリル酸メトキシエチル、アクリル酸グリシジル、メタクリル酸メチル、メタクリル酸エチル、メタクリル酸n−ブチル、メタクリル酸イソブチル、メタクリル酸メトキシエチル、メタクリル酸グリシジル、及びそれらの混合物を包含する群から選ばれることを特徴とする請求項4に記載の共重合体。
- エステルが、共重合体の全重量に基づいて、5重量%〜40重量%、特に10重量%〜30重量%、好ましくは15重量%〜25重量%の重量分率を持つことを特徴とする請求項4または5に記載の共重合体。
- 共重合体がα−β−不飽和モノカルボン酸とα−β−不飽和モノカルボン酸のエステルの共重合体であることを特徴とする請求項1〜6のいずれかに記載の共重合体。
- 共重合体が溶液付加共重合体または溶液共重合体の形であることを特徴とする請求項1〜7のいずれかに記載の共重合体。
- 共重合体が60℃〜140℃、特に80℃〜120℃、好ましくは100℃〜120℃のガラス転移温度を持つことを特徴とする請求項1〜8のいずれかに記載の共重合体。
- 共重合体が5g/10分〜50分g/10分、特に10g/10分〜45g/10分、好ましくは15g/10分〜30g/10分のメルトフローインデックスを持つことを特徴とする請求項1〜9のいずれかに記載の共重合体。
- 共重合体が水性pH中性環境で及び/または水性アルカリ性環境で崩壊可能または溶解可能または実質的に溶解可能であることを特徴とする請求項1〜10のいずれかに記載の共重合体。
- 共重合体が、衝撃改質剤、好ましくはカルボキシル基に対して反応性の衝撃改質剤、好ましくはエポキシ基及び/またはアミノ基を持つ衝撃改質剤を与えられているか、またはそれを配合されていることを特徴とする請求項1〜11のいずれかに記載の共重合体。
- 衝撃改質剤が、衝撃改質剤を与えられているかまたはそれを配合されている共重合体の全重量に基づいて、10重量%〜40重量%、特に12重量%〜30重量%、好ましくは15重量%〜25重量%の重量分率を持つことを特徴とする請求項12に記載の共重合体。
- 請求項1〜13のいずれかに記載の共重合体を製造するための方法において、α−β−不飽和モノカルボン酸、好ましくはアクリル酸、及び共単量体、好ましくはα−β−不飽和モノカルボン酸のエステルが、溶液中で共重合されることを特徴とする方法。
- 請求項1〜11のいずれかに記載の共重合体と衝撃改質剤を含むことを特徴とする共重合体化合物。
- 特に請求項15に記載の共重合体化合物を製造するための方法において、共重合体が、剪断力の作用下で衝撃改質剤と溶融状態で混合され、共重合体と衝撃改質剤の割合が、好ましくは共重合体が連続相を形成しかつ衝撃改質剤が不連続相を形成するように選ばれることを特徴とする方法。
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US20180022847A1 (en) | 2018-01-25 |
WO2012055972A1 (de) | 2012-05-03 |
CN103314022A (zh) | 2013-09-18 |
JP2013540874A (ja) | 2013-11-07 |
US20160297910A1 (en) | 2016-10-13 |
US9777090B2 (en) | 2017-10-03 |
JP6343598B2 (ja) | 2018-06-13 |
CN106883339B (zh) | 2019-07-23 |
US9399691B2 (en) | 2016-07-26 |
US10308743B2 (en) | 2019-06-04 |
EP2447292B1 (de) | 2017-03-29 |
EP2447292A1 (de) | 2012-05-02 |
CN106883339A (zh) | 2017-06-23 |
TW201229066A (en) | 2012-07-16 |
CN103314022B (zh) | 2016-11-09 |
ES2625878T3 (es) | 2017-07-20 |
US20130225779A1 (en) | 2013-08-29 |
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