LU100868B1 - Method for producing a grafted rubber and tire comprising the grafted rubber - Google Patents

Method for producing a grafted rubber and tire comprising the grafted rubber Download PDF

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Publication number
LU100868B1
LU100868B1 LU100868A LU100868A LU100868B1 LU 100868 B1 LU100868 B1 LU 100868B1 LU 100868 A LU100868 A LU 100868A LU 100868 A LU100868 A LU 100868A LU 100868 B1 LU100868 B1 LU 100868B1
Authority
LU
Luxembourg
Prior art keywords
polymer
rubber
carbon
grafted rubber
terminal
Prior art date
Application number
LU100868A
Inventor
Lehani Verwey
Gyula Julius Vancso
Louis Reuvekamp
Steven M Schultz
Original Assignee
Apollo Tyres Global R & D Bv
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 Apollo Tyres Global R & D Bv filed Critical Apollo Tyres Global R & D Bv
Priority to LU100868A priority Critical patent/LU100868B1/en
Priority to PCT/EP2019/067061 priority patent/WO2020002460A1/en
Application granted granted Critical
Publication of LU100868B1 publication Critical patent/LU100868B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
    • C08G81/028—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G containing polyamide sequences
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B60C1/0016—Compositions of the tread
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
    • 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
    • C08C19/20—Incorporating sulfur atoms into the molecule
    • 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
    • C08C19/22—Incorporating nitrogen atoms into the molecule
    • 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
    • C08F8/04—Reduction, e.g. hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
    • C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C08G81/021—Block or graft polymers containing only sequences of polymers of C08C or C08F
    • C08G81/022—Block or graft polymers containing only sequences of polymers of C08C or C08F containing sequences of polymers of conjugated dienes and of polymers of alkenyl aromatic compounds

Abstract

The present invention relates to a method for producing a grafted rubber, the method comprising the steps of: A) providing a rubber comprising at least one olefinic carbon-carbon-double bond, B) providing a polymer being capable of exhibiting lower critical solution temperature (LCST) properties and comprising a terminal functional thiol group capable of reacting with the olefinic carbon-carbon double bond of the rubber, wherein the polymer is obtained by the steps of: Bl) reversible addition-fragmentation chain transfer (RAFT) polymerization of a monomer comprising at least one olefinic carbon-carbon-double bond in the presence of a thiocarbonylthio RAFT agent thereby forming a polymer comprising a terminal thiocarbonylthio group, and B2) cleaving the terminal thiocarbonylthio group to a thiol group thereby attaining the terminal thiol functionality of the polymer, and C) reacting the polymer with the rubber by a radical thiol-ene reaction thereby forming a grafted rubber, the grafted rubber comprising a backbone derived from the rubber and sidechains derived from the polymer. The polymer in a further step B3) is treated with a reducing agent before being used in the grafting reaction of step C).
LU100868A 2018-06-29 2018-06-29 Method for producing a grafted rubber and tire comprising the grafted rubber LU100868B1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
LU100868A LU100868B1 (en) 2018-06-29 2018-06-29 Method for producing a grafted rubber and tire comprising the grafted rubber
PCT/EP2019/067061 WO2020002460A1 (en) 2018-06-29 2019-06-26 Method for producing a grafted rubber and tire comprising the grafted rubber

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
LU100868A LU100868B1 (en) 2018-06-29 2018-06-29 Method for producing a grafted rubber and tire comprising the grafted rubber

Publications (1)

Publication Number Publication Date
LU100868B1 true LU100868B1 (en) 2019-12-30

Family

ID=63113603

Family Applications (1)

Application Number Title Priority Date Filing Date
LU100868A LU100868B1 (en) 2018-06-29 2018-06-29 Method for producing a grafted rubber and tire comprising the grafted rubber

Country Status (2)

Country Link
LU (1) LU100868B1 (en)
WO (1) WO2020002460A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20230220191A1 (en) * 2020-06-01 2023-07-13 Sumitomo Rubber Industries, Ltd. Polymer composite, rubber composition, and tire
KR20220056554A (en) * 2020-10-28 2022-05-06 주식회사 엘지화학 Modified conjugated diene-based polymer and preparing method thereof
JP2022077143A (en) * 2020-11-11 2022-05-23 住友ゴム工業株式会社 Plasticizer, composition, and tire

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030199653A1 (en) * 2002-03-27 2003-10-23 Mccormick Charles L Preparation of transition metal nanoparticles and surfaces modified with (co)polymers synthesized by RAFT
US20080234391A1 (en) * 2007-03-21 2008-09-25 Mccormick Charles L Synthesis of Reversible Shell Crosslinked Nanostructures
EP2607101A1 (en) * 2011-12-21 2013-06-26 The Goodyear Tire & Rubber Company Method of making a graft copolymer and rubber composition comprising such a graft copolymer
US20140350182A1 (en) * 2011-12-14 2014-11-27 Commonwealth Scientique And Industrial Research Organisation Raft polymers

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8536266B2 (en) 2011-12-21 2013-09-17 The Goodyear Tire & Rubber Company Pneumatic tire
US9156932B2 (en) * 2011-12-21 2015-10-13 The Goodyear Tire & Rubber Company Method of making a graft copolymer
US8415432B1 (en) 2011-12-21 2013-04-09 The Goodyear Tire & Rubber Company Rubber composition and pneumatic tire
US8883884B2 (en) 2012-11-27 2014-11-11 The Goodyear Tire & Rubber Company Pneumatic tire

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030199653A1 (en) * 2002-03-27 2003-10-23 Mccormick Charles L Preparation of transition metal nanoparticles and surfaces modified with (co)polymers synthesized by RAFT
US20080234391A1 (en) * 2007-03-21 2008-09-25 Mccormick Charles L Synthesis of Reversible Shell Crosslinked Nanostructures
US20140350182A1 (en) * 2011-12-14 2014-11-27 Commonwealth Scientique And Industrial Research Organisation Raft polymers
EP2607101A1 (en) * 2011-12-21 2013-06-26 The Goodyear Tire & Rubber Company Method of making a graft copolymer and rubber composition comprising such a graft copolymer

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ANJA S. GOLDMANN ET AL: "Surface Modification of Poly(divinylbenzene) Microspheres via Thiol-Ene Chemistry and Alkyne-Azide Click Reactions", MACROMOLECULES, vol. 42, 27 April 2009 (2009-04-27), USA, pages 3707 - 3714, XP002789968, DOI: 10.1021/ma900332d *
GRAEME MOAD, EZIO RIZZARDO, SAN H THANG: "End-functional polymers, thiocarbonylthio group removal/transformation and reversible addition-fragmentation-chain transfer (RAFT) polymerization", POLYMER INTERNATIONAL, vol. 60, no. 1, 23 December 2010 (2010-12-23), pages 9 - 25, XP002789967, DOI: 10.1002/pi.2988 *
HELEN WILLCOCK, RACHEL K. O'REILLY: "End group removal and modification of RAFT polymers", POLYMER CHEMISTRY, vol. 1, 23 December 2009 (2009-12-23), UK, pages 149 - 157, XP002789969, DOI: 10.1039/B9PY00340A *

Also Published As

Publication number Publication date
WO2020002460A1 (en) 2020-01-02

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FG Patent granted

Effective date: 20191230