BRPI0821956A2 - polìmeros funcionalizados de hidroxiarila - Google Patents

polìmeros funcionalizados de hidroxiarila Download PDF

Info

Publication number
BRPI0821956A2
BRPI0821956A2 BRPI0821956-7A BRPI0821956A BRPI0821956A2 BR PI0821956 A2 BRPI0821956 A2 BR PI0821956A2 BR PI0821956 A BRPI0821956 A BR PI0821956A BR PI0821956 A2 BRPI0821956 A2 BR PI0821956A2
Authority
BR
Brazil
Prior art keywords
polymer
functionalized polymers
cyclic amine
hydroxyaryl
polymers
Prior art date
Application number
BRPI0821956-7A
Other languages
English (en)
Inventor
Zengquan Qin
Yuan-Yong Yan
Xiao-Dong Pan
Dennis R Brumbaugh
Jason Poulton
Original Assignee
Bridgestone Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bridgestone Corp filed Critical Bridgestone Corp
Publication of BRPI0821956A2 publication Critical patent/BRPI0821956A2/pt

Links

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
    • C08F212/00—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 an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • 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
    • C08F212/00—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 an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
    • C08F212/22—Oxygen
    • C08F212/24—Phenols or alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/08—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
    • C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
    • C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
    • 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
    • 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
    • C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
    • C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
    • 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
    • C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
    • C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
    • C08F279/04—Vinyl aromatic monomers and nitriles as the only monomers
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • 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
    • 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
    • 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
    • C08F297/04—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 polymerising vinyl aromatic monomers and conjugated dienes
    • 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
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • 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
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • 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
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F36/06—Butadiene
    • 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
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F36/08—Isoprene
    • 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
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/46—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from alkali metals
    • 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
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/46—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from alkali metals
    • C08F4/48—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from alkali metals selected from lithium, rubidium, caesium or francium
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/06—Oxidation
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/12—Hydrolysis
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • 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
    • C08L53/02—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 of vinyl-aromatic monomers and conjugated dienes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
    • C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] 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
    • C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F236/10—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with vinyl-aromatic monomers
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Emergency Medicine (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polymerization Catalysts (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

POLìMEROS FUNCIONALIZADOS E INICIADORES PARA FAZER OS MESMOS Um polímero inclui em uma extremidade um radical de amina cíclica ligada ao polimero através de um átomo de nitrogênio de anel. O polímero pode ser fornecido utilizando uma versão litiada da amina cíclica para iniciar polimerização de um ou mais monómeros etilenicamente insaturados. O polímero pode ser utilizado na produção em uma variedade de vulcanizados.
BRPI0821956-7A 2007-12-28 2008-12-28 polìmeros funcionalizados de hidroxiarila BRPI0821956A2 (pt)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US1727807P 2007-12-28 2007-12-28
US12758608P 2008-05-14 2008-05-14
US8218108P 2008-07-18 2008-07-18
US11010708P 2008-10-31 2008-10-31
PCT/US2008/088384 WO2009086490A2 (en) 2007-12-28 2008-12-28 Hydroxyaryl functionalized polymers

Publications (1)

Publication Number Publication Date
BRPI0821956A2 true BRPI0821956A2 (pt) 2011-08-30

Family

ID=40825095

Family Applications (1)

Application Number Title Priority Date Filing Date
BRPI0821956-7A BRPI0821956A2 (pt) 2007-12-28 2008-12-28 polìmeros funcionalizados de hidroxiarila

Country Status (10)

Country Link
US (4) US8871871B2 (pt)
EP (3) EP2937365B1 (pt)
JP (1) JP5701062B2 (pt)
KR (4) KR101657603B1 (pt)
CN (2) CN105601782B (pt)
BR (1) BRPI0821956A2 (pt)
ES (3) ES2612683T3 (pt)
RU (2) RU2497835C2 (pt)
WO (1) WO2009086490A2 (pt)
ZA (1) ZA201004493B (pt)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5701062B2 (ja) * 2007-12-28 2015-04-15 株式会社ブリヂストン ヒドロキシアリール官能化重合体
ES2458120T3 (es) * 2009-06-30 2014-04-30 Bridgestone Corporation Polímeros funcionalizados con hidroxiarilo
EP2448900B1 (en) 2009-06-30 2017-04-26 Bridgestone Corporation Anionic polymerization initiators and processes
WO2011002830A2 (en) 2009-06-30 2011-01-06 Bridgestone Corporation Polymers functionalized with hydroxyl group-containing diphenylethylene
JP5889787B2 (ja) * 2009-07-01 2016-03-22 株式会社ブリヂストン フリーラジカル開始重合によるヒドロキシアリール官能化共重合体の製造方法
KR101909756B1 (ko) 2009-12-31 2018-10-18 가부시키가이샤 브리지스톤 아미노실란 개시제 및 이로부터 제조된 관능화된 중합체
EP2539394B1 (en) * 2010-02-28 2014-11-19 Bridgestone Corporation Rubber compositions including siliceous fillers
BR112012030344B1 (pt) 2010-05-31 2020-10-27 Bridgestone Corporation metilestireno contendo grupo hidroxila e polímeros incorporando o mesmo
US9371434B2 (en) 2010-07-02 2016-06-21 Bridgestone Corporation Elastomeric compounds having increased cold flow resistance and methods producing the same
US8637600B2 (en) * 2010-08-11 2014-01-28 Bridgestone Corporation Processing of rubber compositions including siliceous fillers
EP2630190B1 (en) 2010-10-18 2018-08-22 Bridgestone Corporation Tread rubber compounds having improved abrasion resistance using functionalized liquid polybutadiene
WO2012091753A1 (en) 2010-12-30 2012-07-05 Bridgestone Corporation Aminosilane initiators and functionalized polymers prepared therefrom
US9221923B2 (en) 2010-12-31 2015-12-29 Bridgestone Corporation Coupled polymers and methods for making same
JP5783797B2 (ja) 2011-05-25 2015-09-24 株式会社ブリヂストン ゴム組成物の製造方法
US9000070B2 (en) 2011-10-19 2015-04-07 Bridgestone Corporation Mixing of telechelic rubber formulations
TWI585115B (zh) 2011-12-15 2017-06-01 普利司通股份有限公司 經穩定之多價陰離子聚合反應引發劑及其製備方法
US9868805B2 (en) 2012-05-01 2018-01-16 Bridgestone Corporation Polydienes and diene copolymers having organophosphine functionality
FR3027602B1 (fr) 2014-10-27 2017-12-29 Michelin & Cie Procede de synthese d'un polymere porteur de groupement hydroxyaryle, produit issu de ce procede et composition le contenant
FR3027904B1 (fr) 2014-11-04 2016-12-30 Michelin & Cie Procede de synthese d'un polymere porteur de groupement hydroxyaryle, produit issu de ce procede et composition le contenant
US10584186B2 (en) 2015-07-22 2020-03-10 Bridgestone Corporation Silane-functionalized polymer and process for making and using same
FR3040058B1 (fr) 2015-08-13 2019-07-19 Compagnie Generale Des Etablissements Michelin Procede de synthese d'un polymere porteur d'un groupement fonctionnel, produit issu de ce procede et composition le contenant.
FR3043591A1 (fr) * 2015-11-13 2017-05-19 Michelin & Cie Composite a base de composant metallique et d'une matrice polymere fonctionnelle
EP3374407B1 (en) 2015-11-13 2020-04-08 Bridgestone Corporation Functional initiator for anionic polymerization
FR3043680B1 (fr) * 2015-11-13 2017-12-08 Michelin & Cie Composition de caoutchouc comprenant un polymere dienique fonctionnel
TWI699885B (zh) * 2016-03-22 2020-07-21 聯華電子股份有限公司 半導體結構與其製作方法
JP7059378B2 (ja) * 2017-12-30 2022-04-25 株式会社ブリヂストン 複数の末端官能化ポリマーを含む組成物
US12319795B2 (en) 2019-12-30 2025-06-03 Bridgestone Corporation Rubber compositions prepared with a polar polysulfide crosslinking agent
JP7413795B2 (ja) * 2020-01-27 2024-01-16 住友ゴム工業株式会社 共重合体、ゴム組成物及びタイヤ
EP4245803B1 (en) * 2020-11-16 2025-07-09 NOK Corporation Nitrile rubber-based composition

Family Cites Families (107)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3109871A (en) 1960-12-27 1963-11-05 Phillips Petroleum Co Production and curing of polyfunctional terminally reactive polymers
JPS4941116B1 (pt) 1970-06-29 1974-11-07
JPS4941116Y2 (pt) 1971-03-19 1974-11-11
US3978103A (en) 1971-08-17 1976-08-31 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Sulfur containing organosilicon compounds
US3873489A (en) 1971-08-17 1975-03-25 Degussa Rubber compositions containing silica and an organosilane
US3770698A (en) * 1971-12-17 1973-11-06 C Riew Phenol terminated carboxy containing diene elastomers
CH585166A5 (pt) * 1973-03-30 1977-02-28 Hoffmann La Roche
US4182803A (en) 1973-06-07 1980-01-08 Sumitomo Chemical Company, Limited Elastomer
US3931107A (en) * 1973-06-21 1976-01-06 Phillips Petroleum Company Polyalkoxy monovinylaromatic compound in copolymerization of a conjugated diene with a monovinyl-substituted aromatic compound
SU580840A3 (ru) 1974-02-07 1977-11-15 Дегусса (Фирма) Способ получени серосодержащих кремнийорганических соединений
FR2313389A1 (fr) * 1975-06-06 1976-12-31 Anvar Nouveaux amorceurs de polymerisation organolithiens bi-fonctionnels et leurs applications, en particulier pour l'obtention d'elastomeres thermoplastiques
US4002594A (en) 1975-07-08 1977-01-11 Ppg Industries, Inc. Scorch retardants for rubber reinforced with siliceous pigment and mercapto-type coupling agent
US3993853A (en) * 1975-10-24 1976-11-23 Phillips Petroleum Company Preparation of functional polymers
US4181545A (en) 1977-04-28 1980-01-01 United Technologies Corporation Hydroxylic aromatic compounds as additives for rubber-based, composite solid propellants
US4255296A (en) 1977-12-02 1981-03-10 Bridgestone Tire Company Limited Polybutadiene rubber composition
US4321343A (en) 1980-10-17 1982-03-23 W. R. Grace & Co. Polyisobutylene/phenol polymers treated with diisocyanates and poly(oxyalkylene)polyols
JPS5821434A (ja) 1981-07-31 1983-02-08 Japan Synthetic Rubber Co Ltd ポリブタジエンゴム組成物
JPS58189203A (ja) 1982-04-30 1983-11-04 Nippon Zeon Co Ltd ゴム組成物
US4429091A (en) 1983-03-09 1984-01-31 The Firestone Tire & Rubber Company Oligomeric oxolanyl alkanes as modifiers for polymerization of dienes using lithium-based initiators
US4499243A (en) 1983-11-07 1985-02-12 Monsanto Company Method of treating diene rubber with amino- and hydroxy aryl compounds
DE3482472D1 (de) 1983-12-26 1990-07-19 Nippon Zeon Co Verfahren zur modifizierung von polymeren von konjugierten dienen.
JPS61225202A (ja) 1985-03-29 1986-10-07 Nippon Zeon Co Ltd ゴムの変性方法
JPS63218705A (ja) * 1987-03-06 1988-09-12 Nippon Paint Co Ltd 保護された官能基を有するアニオン重合開始剤およびその製造方法
US5153291A (en) 1988-06-28 1992-10-06 Bayer Aktiengesellschaft Trialkylsilyloxy-1,1-diphenyl ethylenes and polymers produced therewith
DE3821745A1 (de) * 1988-06-28 1990-02-08 Bayer Ag Trialkylsilyloxy-diphenylethylene und damit hergestellte polymere
US4908404A (en) 1988-08-22 1990-03-13 Biopolymers, Inc. Synthetic amino acid-and/or peptide-containing graft copolymers
US5081191A (en) 1989-01-18 1992-01-14 The Dow Chemical Company Functionalized polymers prepared by anionic polymerization
US4975491A (en) 1989-01-18 1990-12-04 The Dow Chemical Company Functionalized polymers prepared by anionic polymerization
JPH06102737B2 (ja) 1989-04-13 1994-12-14 東洋ゴム工業株式会社 タイヤ用トレッドゴム組成物
DE4003079A1 (de) 1990-02-02 1991-08-08 Bayer Ag Benzophenonderivate und polymere mit phenolischen hydroxylgruppen
GB9002804D0 (en) * 1990-02-08 1990-04-04 Secr Defence Anionic polymerisation
US5109907A (en) 1990-04-09 1992-05-05 Bridgestone/Firestone, Inc. Diene polymers and copolymers terminated by reaction with N-alkyl and N-aryl imines
US5153159A (en) 1990-04-09 1992-10-06 Bridgestone/Firestone, Inc. Elastomers and products having reduced hysteresis
CA2040457A1 (en) * 1990-04-30 1991-10-31 Timothy E. Long Block copolymers containing poly(1,3-conjugated dienes) and poly (vinylphenols), silyl protected poly (vinylphenols) or poly (metal phenolates)
JP3057508B2 (ja) * 1990-06-21 2000-06-26 日本曹達株式会社 ｐ―アルケニルフェノール系重合体の製造方法
FR2677544B1 (fr) 1991-06-14 1993-09-24 Oreal Composition cosmetique contenant un melange de nanopigments d'oxydes metalliques et de pigments melaniques.
US5362819A (en) 1992-01-30 1994-11-08 Gencorp Inc. Polyester-flexible polymer block copolymers and mixtures thereof
JPH05230126A (ja) 1992-02-25 1993-09-07 Nippon Steel Chem Co Ltd 芳香族ヒドロキシル基を有するスチレン系ポリマーとその製造法
US5455307A (en) 1992-04-03 1995-10-03 Exxon Chemical Patents Inc. Polymeric stabilizers for polyolefins
US5674798A (en) * 1992-10-16 1997-10-07 Bridgestone Corporation Hydrocarbon soluble anionic polymerization initiators
US5336726A (en) * 1993-03-11 1994-08-09 Shell Oil Company Butadiene polymers having terminal silyl groups
US5565526A (en) * 1994-05-13 1996-10-15 Fmc Corporation Functionalized initiators for anionic polymerization
EP0746572B1 (en) * 1994-02-18 1999-04-28 Fmc Corporation New functionalized initiators for anionic polymerization
JP3246172B2 (ja) 1994-03-18 2002-01-15 住友化学工業株式会社 ゴム組成物およびそれを用いるスチールコードとの加硫接着方法
US5708092A (en) * 1994-05-13 1998-01-13 Fmc Corporation Functionalized chain extended initiators for anionic polymerization
US5567815A (en) 1994-07-18 1996-10-22 Bridgestone Corporation Teritary amine containing antonic initiators used in preparing polymers and process for the preparation thereof
US6489389B1 (en) 1994-08-19 2002-12-03 Bridgestone Corporation Rubber composition for tire treads
US5486568A (en) * 1994-12-20 1996-01-23 Shell Oil Company Protected functional initiated polymers capped with low surface energy fluorocarbons
US5574109A (en) 1995-02-01 1996-11-12 Bridgestone Corporation Aminoalkyllithium compounds containing cyclic amines and polymers therefrom
US5580919A (en) 1995-03-14 1996-12-03 The Goodyear Tire & Rubber Company Silica reinforced rubber composition and use in tires
RU2074197C1 (ru) * 1995-04-14 1997-02-27 Воронежский филиал Государственного предприятия "Научно-исследовательский институт синтетического каучука им.акад.Лебедева С.В." Способ получения полимеров бутадиена и сополимеров его со стиролом
EP0745655A3 (en) * 1995-06-02 1998-04-29 National Starch and Chemical Investment Holding Corporation Dissipative laminating adhesive
JP3388949B2 (ja) 1995-07-28 2003-03-24 株式会社東芝 耐熱部材およびその製造方法
US5922810A (en) * 1995-07-31 1999-07-13 Fmc Corporation Deprotection of protected functional polymers
US5780551A (en) 1995-11-02 1998-07-14 Fmc Corporation Telechelic polymers from mixed initiator
US5583245A (en) 1996-03-06 1996-12-10 The Goodyear Tire & Rubber Company Preparation of sulfur-containing organosilicon compounds
FR2746803B1 (fr) 1996-03-29 1998-04-24 Ceca Sa Resines novolaques phenol/diene, procede de preparation et compositions a base de caoutchouc renfermant lesdites resines
US5696197A (en) 1996-06-21 1997-12-09 The Goodyear Tire & Rubber Company Heterogeneous silica carbon black-filled rubber compound
US5663396A (en) 1996-10-31 1997-09-02 The Goodyear Tire & Rubber Company Preparation of sulfur-containing organosilicon compounds
US5684171A (en) 1997-02-11 1997-11-04 The Goodyear Tire & Rubber Company Process for the preparation of organosilicon polysulfide compounds
US5684172A (en) 1997-02-11 1997-11-04 The Goodyear Tire & Rubber Company Process for the preparation of organosilicon polysulfide compounds
US6008295A (en) * 1997-07-11 1999-12-28 Bridgestone Corporation Diene polymers and copolymers incorporating partial coupling and terminals formed from hydrocarboxysilane compounds
US6525118B2 (en) 1997-07-11 2003-02-25 Bridgestone Corporation Processability of silica-filled rubber stocks with reduced hysteresis
JP2002507511A (ja) 1998-01-21 2002-03-12 リフレキサイト・コーポレーション 長寿命ポリ塩化ビニル蛍光シ−ト材
US6242522B1 (en) 1998-03-24 2001-06-05 Bridgestone Corporation Rubber composition for tire tread and pneumatic tire using same
US6852785B1 (en) 1999-04-22 2005-02-08 Dunlop Tire Corporation Vulcanizable elastomeric compositions for use as tire treads
US6977281B1 (en) 1999-11-12 2005-12-20 Bridgestone Corporation Modified polymers prepared with lanthanide-based catalysts
DE60041550D1 (de) 1999-11-12 2009-03-26 Bridgestone Corp Modifizierte polymere hergestellt mit katalysator auf basys von lanthaniden
US6476110B1 (en) 2000-02-18 2002-11-05 Continental Ag Rubber composition containing solid magnetizable particles of greater stiffness than the rubbery compounds
AU2001245882A1 (en) * 2000-03-20 2001-10-03 Fmc Corporation Terminal olefin functionalized macromonomers
EP1290083A1 (fr) * 2000-05-22 2003-03-12 Société de Technologie Michelin Composition pour bande de roulement de pneumatique et son procede de preparation
US6558805B2 (en) * 2000-10-05 2003-05-06 The Goodyear Tire & Rubber Company Functionalized rubbery polymer containing polysiloxane
JP4431268B2 (ja) * 2000-11-17 2010-03-10 株式会社ミクニ 電子制御燃料噴射装置
RU2175330C1 (ru) * 2001-01-25 2001-10-27 Федеральное государственное унитарное предприятие "Научно-исследовательский институт синтетического каучука им. академика С.В. Лебедева" Способ получения диеновых (со)полимеров, содержащих функциональные группы
US7618937B2 (en) 2001-07-20 2009-11-17 Northwestern University Peptidomimetic polymers for antifouling surfaces
US7858679B2 (en) 2001-07-20 2010-12-28 Northwestern University Polymeric compositions and related methods of use
WO2003008376A2 (en) 2001-07-20 2003-01-30 Northwestern University Adhesive dopa-containing polymers and related methods of use
US8815793B2 (en) 2001-07-20 2014-08-26 Northwestern University Polymeric compositions and related methods of use
US6699813B2 (en) 2001-11-07 2004-03-02 Bridgestone Corporation Lanthanide-based catalyst composition for the manufacture of polydienes
US6838539B2 (en) 2002-02-12 2005-01-04 Bridgestone Corporation Cureable silane functionalized sealant composition and manufacture of same
JP3797262B2 (ja) * 2002-04-05 2006-07-12 住友化学株式会社 変性ジエン系重合体ゴム、その製造方法及びゴム組成物
DE60326850D1 (de) * 2002-07-11 2009-05-07 Bridgestone Corp Herstellung von initiatoren mit funktionellen gruppen für die anionische polymerisation
US20080171012A1 (en) 2007-01-11 2008-07-17 Phillip Messersmith Fouling Resistant Coatings and Methods of Making Same
US8911831B2 (en) 2002-07-19 2014-12-16 Northwestern University Surface independent, surface-modifying, multifunctional coatings and applications thereof
WO2004020475A1 (en) * 2002-08-30 2004-03-11 Bridgestone Corporation Functionalized polymers and improved vulcanizates therefrom
WO2004041870A2 (en) 2002-10-30 2004-05-21 Bridgestone Corporation The use of sulfur containing initiators for anionic polymerization of monomers
EP1562630A4 (en) 2002-10-31 2009-02-18 Univ Northwestern INJECTABLE BIOADHûSIVE POLYMERS HYDROGELES AND RELEVANT PROCESSES FOR ENZYMATIC PRODUCTION
JP3913210B2 (ja) 2003-05-30 2007-05-09 住友ゴム工業株式会社 タイヤ用ゴム組成物およびそれを用いたタイヤ
US6972307B2 (en) 2003-07-29 2005-12-06 The Goodyear Tire & Rubber Company Rubber composition containing nanoscaled zinc oxide particles
US7056985B2 (en) 2004-02-11 2006-06-06 University Of Massachusetts Lowell End-capped polymer chains and products thereof
US7226979B2 (en) 2004-02-11 2007-06-05 University Of Massachusetts Lowell Copolymers comprising olefin and protected or unprotected hydroxystyrene units
CN1960719B (zh) 2004-03-25 2011-12-07 密执安州立大学董事会 棉酚共结晶及其应用
US7842830B2 (en) * 2004-06-14 2010-11-30 Georgia Tech Research Corporation Transition-metal charge-transport materials, methods of fabrication thereof, and methods of use thereof
US7279527B2 (en) 2005-04-22 2007-10-09 Bridgestone Corporation Method of converting anionic living end to protected free radical living end and applications thereof
US7868110B2 (en) * 2005-05-20 2011-01-11 Bridgestone Corporation Anionic polymerization initiators and polymers therefrom
JP4934323B2 (ja) 2006-02-07 2012-05-16 株式会社ブリヂストン 変性天然ゴム及びその製造方法、並びにそれを用いたゴム組成物及びタイヤ
WO2008049108A1 (en) 2006-10-19 2008-04-24 Northwestern University Surface-independent, surface-modifying, multifunctional coatings and applications thereof
US8841376B2 (en) 2006-12-31 2014-09-23 Bridgestone Corporation Methods for identifying and utilizing rubber compositions with good wet traction performance
JP5701062B2 (ja) * 2007-12-28 2015-04-15 株式会社ブリヂストン ヒドロキシアリール官能化重合体
ATE522372T1 (de) 2008-06-30 2011-09-15 Yokohama Rubber Co Ltd Gummizusammensetzung für reifen
WO2011002830A2 (en) * 2009-06-30 2011-01-06 Bridgestone Corporation Polymers functionalized with hydroxyl group-containing diphenylethylene
ES2458120T3 (es) 2009-06-30 2014-04-30 Bridgestone Corporation Polímeros funcionalizados con hidroxiarilo
EP2448900B1 (en) 2009-06-30 2017-04-26 Bridgestone Corporation Anionic polymerization initiators and processes
JP5889787B2 (ja) 2009-07-01 2016-03-22 株式会社ブリヂストン フリーラジカル開始重合によるヒドロキシアリール官能化共重合体の製造方法
EP2539394B1 (en) 2010-02-28 2014-11-19 Bridgestone Corporation Rubber compositions including siliceous fillers
BR112012030344B1 (pt) 2010-05-31 2020-10-27 Bridgestone Corporation metilestireno contendo grupo hidroxila e polímeros incorporando o mesmo
US8637600B2 (en) 2010-08-11 2014-01-28 Bridgestone Corporation Processing of rubber compositions including siliceous fillers

Also Published As

Publication number Publication date
US20190322777A1 (en) 2019-10-24
US10227425B2 (en) 2019-03-12
KR20160110557A (ko) 2016-09-21
RU2637124C2 (ru) 2017-11-30
CN105601782B (zh) 2019-06-18
KR101604566B1 (ko) 2016-03-17
US20150141582A1 (en) 2015-05-21
CN101959903B (zh) 2016-02-17
EP2231719A4 (en) 2011-06-29
EP2231719A2 (en) 2010-09-29
US20190233557A1 (en) 2019-08-01
RU2497835C2 (ru) 2013-11-10
JP2011508068A (ja) 2011-03-10
ES2619365T3 (es) 2017-06-26
KR101598234B1 (ko) 2016-02-26
WO2009086490A3 (en) 2009-09-24
WO2009086490A2 (en) 2009-07-09
ZA201004493B (en) 2011-03-30
RU2010131491A (ru) 2012-06-20
KR20150008934A (ko) 2015-01-23
EP2589611A1 (en) 2013-05-08
ES2612683T3 (es) 2017-05-18
US20100286348A1 (en) 2010-11-11
CN105601782A (zh) 2016-05-25
EP2589611B1 (en) 2016-10-26
JP5701062B2 (ja) 2015-04-15
KR20160033242A (ko) 2016-03-25
CN101959903A (zh) 2011-01-26
RU2013136050A (ru) 2015-02-10
US11117987B2 (en) 2021-09-14
EP2937365A1 (en) 2015-10-28
KR101657603B1 (ko) 2016-09-19
EP2937365B1 (en) 2016-12-14
US8871871B2 (en) 2014-10-28
KR20100114054A (ko) 2010-10-22
US11028195B2 (en) 2021-06-08
EP2231719B1 (en) 2015-07-29
ES2551103T3 (es) 2015-11-16

Similar Documents

Publication Publication Date Title
BRPI0908915A2 (pt) polìmeros funcionalizados e iniciadores para fazer os mesmos
BR112017026162A2 (pt) polímero com base em dieno conjugado modificado e método de produção do mesmo, composição de borracha e pneu
BRPI0605394A (pt) polìmeros funcionalizados
AR084330A1 (es) Polimeros a base de etileno y procesos para formarlos
BR112015003477A2 (pt) processo para fabricação de placa de madeira, placa de madeira ou placa de partículas, e uso da pós-cura de uma placa de madeira em um processo
BR112012006015A2 (pt) borrachas de nitrila e sua fabricação em solventes orgânicos
SG11201900914XA (en) Modified conjugated diene-based polymer, rubber composition and tire
BR112013018415A2 (pt) composição ou compósito, material pré-impregnado, material termoplástico ou um produto moldado de resina de termocura modificado com termoplástico, poliaril sulfona, e, composto de benzoxazina
EA201000369A1 (ru) Водные клеевые полимерные дисперсии с низкой вязкостью
GB2474623A (en) Indacenodithiophene and indaenodiseelenophene polymers and their use as organic semiconductors
BR112012012210A2 (pt) polímeros á base de ciclodextrina para distribuição terapêutica
BR112013016665A2 (pt) método de modificação de superfície, corpo elástico de superfície modificada, gaxeta para injetor, injetor e pneu
BR112014009065A2 (pt) polímeros de arquitetura controlada
GB201015397D0 (en) Polymerisation method
BR112013009032A2 (pt) métodos para produzir uma dispersão de copolímero, um asfalto modificado por polímero, e uma emulsão de asfalto modificado por polímero, copolímero, mistura, dispersão aquosa, método, e, composição de asfalto modificado com polímero
EA201691318A1 (ru) Блок-сополимер и клеевая композиция
BRPI0720482B8 (pt) processo para produzir partículas poliméricas absorventes de água, partículas poliméricas absorvedoras de água, uso de partículas poliméricas, e, artigo de higiene
BR112015004803A2 (pt) método para preparação livre de solvente de um polímero de ácido (met)acrílico em solução, solução aquosa de polímeros de ácido (met)acrílico, e uso da mesma
GB2475667A (en) Polymers derived from bis (thienocyclopenta) benzothiadiazole and their use as organic semiconductors
BR112013020735A8 (pt) Diluente não ureia de farinha de soja de baixo ph e métodos para produção do mesmo
BR112015019114A2 (pt) composto polimérico termoplástico, método para a produção de um composto polimérico, artigo moldado e uso de um composto polimérico
BR112014013641A2 (pt) composição de polímero curável, e, compósito
ATE555141T1 (de) Kern-schale-polymer
BR112017025599A2 (pt) resinas de farneseno, composições de borracha e composições de pneus
BR112017003093A2 (pt) filme polimérico termoplástico e respectivo método de obtenção

Legal Events

Date Code Title Description
B06F Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]
B06U Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette]
B06A Patent application procedure suspended [chapter 6.1 patent gazette]
B09A Decision: intention to grant [chapter 9.1 patent gazette]
B11D Dismissal acc. art. 38, par 2 of ipl - failure to pay fee after grant in time