CA2633263A1 - Low surface energy block co-polymer preparation methods and applications - Google Patents
Low surface energy block co-polymer preparation methods and applications Download PDFInfo
- Publication number
- CA2633263A1 CA2633263A1 CA002633263A CA2633263A CA2633263A1 CA 2633263 A1 CA2633263 A1 CA 2633263A1 CA 002633263 A CA002633263 A CA 002633263A CA 2633263 A CA2633263 A CA 2633263A CA 2633263 A1 CA2633263 A1 CA 2633263A1
- Authority
- CA
- Canada
- Prior art keywords
- block
- polymer
- monomer
- surface energy
- low surface
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
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- 150000003254 radicals Chemical class 0.000 claims description 26
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- DCBBWYIVFRLKCD-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-methylprop-2-enamide Chemical compound CN(C)CCNC(=O)C(C)=C DCBBWYIVFRLKCD-UHFFFAOYSA-N 0.000 description 1
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- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- BPCNEKWROYSOLT-UHFFFAOYSA-N n-phenylprop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC=C1 BPCNEKWROYSOLT-UHFFFAOYSA-N 0.000 description 1
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- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 1
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- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
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- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
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- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
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- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- QIFZBTPXXULUNF-UHFFFAOYSA-N tert-butyl-ethenyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)C=C QIFZBTPXXULUNF-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- KLQLOEREHUQEPO-UHFFFAOYSA-N tri(propan-2-yl)silylmethyl prop-2-enoate Chemical compound CC(C)[Si](C(C)C)(C(C)C)COC(=O)C=C KLQLOEREHUQEPO-UHFFFAOYSA-N 0.000 description 1
- WEAZWKYSTGLBSQ-UHFFFAOYSA-N tributylsilyl 2-methylprop-2-enoate Chemical compound CCCC[Si](CCCC)(CCCC)OC(=O)C(C)=C WEAZWKYSTGLBSQ-UHFFFAOYSA-N 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- PWVJTRQTFFVDEU-UHFFFAOYSA-N triethylsilyl 2-methylprop-2-enoate Chemical compound CC[Si](CC)(CC)OC(=O)C(C)=C PWVJTRQTFFVDEU-UHFFFAOYSA-N 0.000 description 1
- VOOUWBRSWSNREM-UHFFFAOYSA-N trimethylsilyl prop-2-enoate Chemical compound C[Si](C)(C)OC(=O)C=C.C[Si](C)(C)OC(=O)C=C VOOUWBRSWSNREM-UHFFFAOYSA-N 0.000 description 1
- VGOXVARSERTCRY-UHFFFAOYSA-N trimethylsilylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC[Si](C)(C)C VGOXVARSERTCRY-UHFFFAOYSA-N 0.000 description 1
- UWAWYGLUQDYLTK-UHFFFAOYSA-N trimethylsilylmethyl prop-2-enoate Chemical compound C[Si](C)(C)COC(=O)C=C UWAWYGLUQDYLTK-UHFFFAOYSA-N 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
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- 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
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
- C08L33/12—Homopolymers or copolymers of methyl methacrylate
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
-
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
-
- 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
-
- 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
-
- 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
- C08F220/22—Esters containing halogen
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
-
- 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
- C08F2438/00—Living radical polymerisation
- C08F2438/02—Stable Free Radical Polymerisation [SFRP]; Nitroxide Mediated Polymerisation [NMP] for, e.g. using 2,2,6,6-tetramethylpiperidine-1-oxyl [TEMPO]
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75087005P | 2005-12-16 | 2005-12-16 | |
| US60/750,870 | 2005-12-16 | ||
| PCT/US2006/047685 WO2007078819A2 (en) | 2005-12-16 | 2006-12-14 | Low surface energy block co-polymer preparation methods and applications |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2633263A1 true CA2633263A1 (en) | 2007-07-12 |
Family
ID=38228745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002633263A Abandoned CA2633263A1 (en) | 2005-12-16 | 2006-12-14 | Low surface energy block co-polymer preparation methods and applications |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US20080312377A1 (https=) |
| EP (1) | EP1960839A4 (https=) |
| JP (1) | JP2009520074A (https=) |
| CA (1) | CA2633263A1 (https=) |
| WO (1) | WO2007078819A2 (https=) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2007136552A2 (en) | 2006-05-09 | 2007-11-29 | Jeffrey Jacob Cernohous | Compatibilized polymer processing additives |
| KR101560854B1 (ko) * | 2008-02-22 | 2015-10-15 | 바스프 에스이 | 플루오로 레벨링제 |
| WO2009128504A1 (ja) * | 2008-04-18 | 2009-10-22 | 東亞合成株式会社 | シーリング材組成物 |
| JP5067482B2 (ja) * | 2008-06-20 | 2012-11-07 | 東亞合成株式会社 | 接着剤組成物 |
| CN102753592A (zh) * | 2010-02-12 | 2012-10-24 | 大金工业株式会社 | 嵌段聚合物的制造方法和嵌段聚合物以及表面处理剂 |
| WO2011116223A1 (en) * | 2010-03-18 | 2011-09-22 | Board Of Regents The University Of Texas System | Silicon-containing block co-polymers, methods for synthesis and use |
| WO2011144407A1 (de) | 2010-05-19 | 2011-11-24 | Evonik Goldschmidt Gmbh | Polysiloxan blockcopolymere und deren verwendung in kosmetischen formulierungen |
| US20130035452A1 (en) * | 2010-05-19 | 2013-02-07 | Evonik Goldschmidt Gmbh | Polysiloxane block copolymers and use thereof in cosmetic formulations |
| DE102011005493A1 (de) * | 2011-03-14 | 2012-09-20 | Evonik Rohmax Additives Gmbh | Estergruppen-umfassende Copolymere und deren Verwendung in Schmiermitteln |
| US20120264884A1 (en) * | 2011-04-12 | 2012-10-18 | Guojun Liu | Amphiphobic Surfaces from Block Copolymers |
| US9359499B2 (en) | 2011-05-05 | 2016-06-07 | Stratasys, Inc. | Radiation curable polymers |
| EP2716669B1 (en) | 2011-06-03 | 2018-11-07 | Sumitomo Rubber Industries, Ltd. | Tire and gasket for syringes |
| JP5763565B2 (ja) | 2012-02-02 | 2015-08-12 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| CN104125984B9 (zh) * | 2012-02-23 | 2017-09-22 | 巴斯夫欧洲公司 | 具有低动态表面张力的氟代丙烯酸酯嵌段共聚物 |
| JP5812935B2 (ja) | 2012-05-16 | 2015-11-17 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| JP6247216B2 (ja) | 2012-09-10 | 2017-12-13 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| JP5620456B2 (ja) | 2012-11-20 | 2014-11-05 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| JP6053482B2 (ja) | 2012-11-30 | 2016-12-27 | 住友ゴム工業株式会社 | 注射器用ガスケットの製造方法 |
| JP6105292B2 (ja) * | 2013-01-07 | 2017-03-29 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| US8822615B1 (en) * | 2013-02-08 | 2014-09-02 | Rohm And Haas Electronic Materials Llc | Block copolymer composition and methods relating thereto |
| US8822616B1 (en) * | 2013-02-08 | 2014-09-02 | Rohm And Haas Electronic Materials Llc | Block copolymer formulation and methods relating thereto |
| US9765169B2 (en) | 2013-04-18 | 2017-09-19 | Carnegie Mellon University | Functionalized polymer hybrids |
| JP5816222B2 (ja) | 2013-04-25 | 2015-11-18 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
| JP5797239B2 (ja) | 2013-06-11 | 2015-10-21 | 住友ゴム工業株式会社 | 立体形状物の表面改質方法及び注射器用ガスケット |
| US10647829B2 (en) | 2013-06-20 | 2020-05-12 | Sumitomo Rubber Industries, Ltd. | Surface modification method and surface modification body |
| FR3010413B1 (fr) * | 2013-09-09 | 2015-09-25 | Arkema France | Procede de controle de la periode d'un assemblage nano-structure comprenant un melange de copolymeres a blocs |
| US9109067B2 (en) * | 2013-09-24 | 2015-08-18 | Xerox Corporation | Blanket materials for indirect printing method with varying surface energies via amphiphilic block copolymers |
| JP5820489B2 (ja) | 2014-01-06 | 2015-11-24 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
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| JP6613692B2 (ja) | 2015-08-03 | 2019-12-04 | 住友ゴム工業株式会社 | 表面改質方法及び表面改質弾性体 |
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| FR2853317B1 (fr) * | 2003-04-01 | 2006-07-07 | Atofina | Alcoxyamines issues de nitroxydes b-phosphores, leur utilisation pour la preparation de mono-ou polyalcoxyamines, polymerisees ou non |
| FR2866026B1 (fr) * | 2004-02-06 | 2008-05-23 | Arkema | Procede de polymerisation radicalaire en emulsion mettant en oeuvre des alcoxyamines hydrosolubles |
-
2006
- 2006-12-14 JP JP2008545802A patent/JP2009520074A/ja active Pending
- 2006-12-14 CA CA002633263A patent/CA2633263A1/en not_active Abandoned
- 2006-12-14 US US12/097,149 patent/US20080312377A1/en not_active Abandoned
- 2006-12-14 EP EP06845400A patent/EP1960839A4/en not_active Withdrawn
- 2006-12-14 WO PCT/US2006/047685 patent/WO2007078819A2/en not_active Ceased
-
2011
- 2011-05-24 US US13/114,297 patent/US20110224356A1/en not_active Abandoned
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| Publication number | Publication date |
|---|---|
| US20110224356A1 (en) | 2011-09-15 |
| US20080312377A1 (en) | 2008-12-18 |
| EP1960839A2 (en) | 2008-08-27 |
| WO2007078819A3 (en) | 2007-12-06 |
| JP2009520074A (ja) | 2009-05-21 |
| EP1960839A4 (en) | 2012-01-11 |
| WO2007078819A2 (en) | 2007-07-12 |
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