JP6689826B2 - 1つ以上の1,1−二置換アルケン化合物を含むポリマー及びそのポリマー組成物 - Google Patents
1つ以上の1,1−二置換アルケン化合物を含むポリマー及びそのポリマー組成物 Download PDFInfo
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- JP6689826B2 JP6689826B2 JP2017513069A JP2017513069A JP6689826B2 JP 6689826 B2 JP6689826 B2 JP 6689826B2 JP 2017513069 A JP2017513069 A JP 2017513069A JP 2017513069 A JP2017513069 A JP 2017513069A JP 6689826 B2 JP6689826 B2 JP 6689826B2
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- Prior art keywords
- monomer
- copolymer
- methylene malonate
- polymer
- glass transition
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- 229920000642 polymer Polymers 0.000 title claims description 312
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- 239000000203 mixture Substances 0.000 title description 62
- 239000000178 monomer Substances 0.000 claims description 323
- 230000009477 glass transition Effects 0.000 claims description 140
- 229920001519 homopolymer Polymers 0.000 claims description 112
- 150000001336 alkenes Chemical class 0.000 claims description 59
- 229920001577 copolymer Polymers 0.000 claims description 59
- BQHDXNZNSPVVKB-UHFFFAOYSA-N diethyl 2-methylidenepropanedioate Chemical group CCOC(=O)C(=C)C(=O)OCC BQHDXNZNSPVVKB-UHFFFAOYSA-N 0.000 claims description 51
- 229920001400 block copolymer Polymers 0.000 claims description 49
- 229920005604 random copolymer Polymers 0.000 claims description 49
- 229910052799 carbon Inorganic materials 0.000 claims description 40
- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical compound OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- KTLZQSZGORXBED-UHFFFAOYSA-N dimethyl 2-methylidenepropanedioate Chemical compound COC(=O)C(=C)C(=O)OC KTLZQSZGORXBED-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- PNIOCTBBHFNVLA-UHFFFAOYSA-N 2-(3-phenylpropoxycarbonyl)prop-2-enoic acid Chemical compound C=C(C(=O)O)C(=O)OCCCC1=CC=CC=C1 PNIOCTBBHFNVLA-UHFFFAOYSA-N 0.000 claims description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
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- ITIAHBUTIYTGJS-UHFFFAOYSA-N 2-(4-phenylbutoxycarbonyl)prop-2-enoic acid Chemical compound C=C(C(=O)O)C(=O)OCCCCC1=CC=CC=C1 ITIAHBUTIYTGJS-UHFFFAOYSA-N 0.000 claims 4
- GOLJHQAYNHRZHE-UHFFFAOYSA-N CC(CCC1=CC=CC=C1)OC(=O)C(=C)C(=O)O Chemical compound CC(CCC1=CC=CC=C1)OC(=O)C(=C)C(=O)O GOLJHQAYNHRZHE-UHFFFAOYSA-N 0.000 claims 1
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- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 6
- YHYKEOAZUABSQX-UHFFFAOYSA-N CCCCCCC(C)OC(=O)C(=C)C(=O)O Chemical compound CCCCCCC(C)OC(=O)C(=C)C(=O)O YHYKEOAZUABSQX-UHFFFAOYSA-N 0.000 description 6
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- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 6
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 6
- 239000004299 sodium benzoate Substances 0.000 description 6
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- 229940054269 sodium pyruvate Drugs 0.000 description 6
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- 239000004115 Sodium Silicate Substances 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
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- 125000001475 halogen functional group Chemical group 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
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- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 5
- 229910052911 sodium silicate Inorganic materials 0.000 description 5
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 4
- 101710179738 6,7-dimethyl-8-ribityllumazine synthase 1 Proteins 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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- 101710186608 Lipoyl synthase 1 Proteins 0.000 description 4
- 101710137584 Lipoyl synthase 1, chloroplastic Proteins 0.000 description 4
- 101710090391 Lipoyl synthase 1, mitochondrial Proteins 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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- 229920001281 polyalkylene Polymers 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- GIDJHDFSBLVVHB-UHFFFAOYSA-N 2-(1-phenylpentan-2-yloxycarbonyl)prop-2-enoic acid Chemical compound CCCC(CC1=CC=CC=C1)OC(=O)C(=C)C(=O)O GIDJHDFSBLVVHB-UHFFFAOYSA-N 0.000 description 3
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
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- LINIRIAONFDUIR-UHFFFAOYSA-N 5-methoxy-2-methoxycarbonylpent-2-enoic acid Chemical group COCCC=C(C(=O)O)C(=O)OC LINIRIAONFDUIR-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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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
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/14—Esters having no free carboxylic acid groups, e.g. dialkyl maleates or fumarates
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/007—After-treatment
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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
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
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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
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/26—Emulsion polymerisation with the aid of emulsifying agents anionic
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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
- C08F297/00—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer
- C08F297/02—Macromolecular compounds obtained by successively polymerising different monomer systems using a catalyst of the ionic or coordination type without deactivating the intermediate polymer using a catalyst of the anionic type
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D135/00—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 a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D135/02—Homopolymers or copolymers of esters
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D153/00—Coating compositions based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J135/00—Adhesives 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 a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J135/02—Homopolymers or copolymers of esters
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
Description
本出願は、2015年7月1日に出願された米国特許出願第14/789,178号、2015年7月28日に出願された同第14/810,741号;2015年6月30日に出願された米国仮特許出願第62/186,479号、2015年6月19日に出願された同第62/182,076号、2014年9月8日に出願された同第62/047,283号、及び2014年9月8日に出願された同第62/047,328号の優先権を主張し、それらの内容全体を参照によって本願明細書に引用したものとする。
BI=(f(M1−M2)+f(M2−M1))/(2XM1(1−XM2))
定義により、真の統計学的ランダム共重合体は、1のBI(1.0)を有する。ブロック状ランダム共重合体は、より低い濃度のM1−M2及びM2−M1ダイアド分率を有することになり、BIが1.0よりも小さくなる。ブロック共重合体は、非常に低い濃度のM1−M2及びM2−M1ダイアド分率を有することになり、BIが1よりもはるかに小さくなり、ゼロに近づく。一方、XM1が0.5以上である交互共重合体は、BI=1+(1/XM1)を有する。ダイアド分率の濃度及びXM1は、Yi−Jun Huange et al.“Random Copolymers of Propylene Oxide and Ethylene Oxide Prepared by Double Metal Cyanide Complex Catalyst”,Chinese Journal of Polymer Science、20:5、2002、pages 453〜459(これはその全体が参照によって本明細書中に組み込まれる)に記載される類似のピーク割当及び技術を使用して、13C−NMR分光法を使用して測定することができる。
Claims (13)
- i)2重量%〜98重量%の第1のモノマーと;
ii)2重量%〜98重量%の第2のモノマーと;
を含む、共重合体であって、
該第1のモノマーは、1つ以上の1,1−二置換アルケンモノマーであり、当該1,1−二置換アルケンモノマーは、別の炭素原子に二重結合し、および2つのカルボニル基にさらに結合する中心炭素原子を含み、
前記第1のモノマーが、前記第1のモノマーのホモポリマーが35℃以上のTgを有して重合することができるような構造を有し、および
前記第2のモノマーが、前記第2のモノマーのホモポリマーが15℃以下のTgを有するような構造を有し、
前記第1のモノマーが、前記共重合体の総重量に基づいて、20重量%以上の濃度で存在し、および前記第2のモノマーが、前記共重合体の総重量に基づいて、20重量%以上の濃度で存在する、前記共重合体。 - 前記第1のモノマーが、第1の1,1−二置換アルケンモノマーであり、前記第2のモノマーが、前記第1のモノマーとは異なる第2の1,1−二置換アルケンモノマーであり、および前記第1のモノマー及び前記第2のモノマーの総濃度が、前記共重合体の総重量に基づいて、30重量%以上である、請求項1に記載の共重合体。
- 前記共重合体が、前記第1のモノマー及び前記第2のモノマーとは異なる1つ以上のさらなるモノマーを含む、請求項1または2に記載の共重合体。
- 前記第1のモノマーが、メチレンマロン酸ジエチル、メチレンマロン酸ジメチル、メチレンマロン酸フェニルプロピルメチル、メチレンマロン酸フェニルプロピルメチル、メチレンマロン酸フェンキルメチル、メチレンマロン酸フェンキルエチル、メチレンマロン酸メンチルエチル、メチレンマロン酸フェニルプロピルエチル、メチレンマロン酸ジシクロヘキシル、メチレンマロン酸シクロヘキシルエチル、メチレンマロン酸イソボルニルエチル、メチレンマロン酸ベンジルエチル、メチレンマロン酸ベンジルメチル、メチレンマロン酸ジベンジル、及びそれらの任意の組み合わせからなる群から選択される、請求項1〜3のいずれかに記載の共重合体。
- 前記第2のモノマーが、メチレンマロン酸メチルメトキシエチル、メチレンマロン酸エチルエトキシエチル、メチレンマロン酸ヘキシルエチル、メチレンマロン酸ジブチル、メチレンマロン酸ジヘキシル、メチレンマロン酸ヘキシルエチル、及びそれらの任意の組み合わせからなる群から選択される、請求項1〜4のいずれかに記載の共重合体。
- 前記共重合体が、第2のポリマーブロックに付着した第1のポリマーブロックを含むブロック共重合体であり、該第1のポリマーブロックが、前記第1のモノマーを含み、前記共重合体が、25℃〜250℃の第1のガラス転移温度を有し、および前記共重合体が、−100℃〜15℃の第2のガラス転移温度を有する、請求項1〜5のいずれかに記載の共重合体。
- 前記共重合体が、−100℃〜15℃の第2のガラス転移温度を有する、請求項1〜5のいずれかに記載の共重合体。
- 前記第1のポリマーブロックが、メチレンマロン酸ジエチル、メチレンマロン酸ジメチル、メチレンマロン酸フェニルプロピルメチル、メチレンマロン酸フェニルプロピルメチル、メチレンマロン酸フェンキルメチル、メチレンマロン酸フェンキルエチル、メチレンマロン酸メンチルエチル、メチレンマロン酸フェニルプロピルエチル、メチレンマロン酸ジシクロヘキシル、メチレンマロン酸シクロヘキシルエチル、メチレンマロン酸イソボルニルエチル、メチレンマロン酸ベンジルエチル、メチレンマロン酸ベンジルメチル、メチレンマロン酸ジベンジル、及びそれらの任意の組み合わせからなる群から選択される1つ以上のモノマーの50重量%以上を含み、および前記第2のポリマーブロックが、メチレンマロン酸メチルメトキシエチル、メチレンマロン酸エチルエトキシエチル、メチレンマロン酸ヘキシルエチル、メチレンマロン酸ジブチル、メチレンマロン酸ジヘキシル、メチレンマロン酸ヘキシルエチル、及びそれらの任意の組み合わせからなる群から選択される1つ以上のモノマーの約50重量%以上を含む、請求項6に記載の共重合体。
- 前記共重合体が、3つ以上のポリマーブロックを含む、請求項6または8に記載の共重合体。
- 前記共重合体が、0.6以上のブロック状化指数、かつ、1以下のブロック状化指数を有するランダム共重合体である、請求項1〜9のいずれかに記載の共重合体。
- 前記共重合体中の1,1−二置換アルケンモノマーの総量が、前記共重合体の総重量に基づいて、98重量%〜100重量%であり、当該共重合体が、25重量%以上の前記第1のモノマー及び25重量%以上の前記第2のモノマーを含む、請求項1〜5のいずれかに記載の共重合体。
- 前記第2のモノマーが、1,1−二置換アルケンモノマーではなく、かつ、1つ以上のアクリレート類、1つ以上のメタクリレート類、スチレン、ブタジエン、アクリロニトリル、またはそれらの任意の組み合わせを含む、請求項1〜5のいずれかに記載の共重合体。
- 前記共重合体が、ブロック共重合体である、請求項12に記載の共重合体。
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