WO2012085895A1 - Tread compound comprising trialkoxymercaptoalkyl-silanes - Google Patents

Tread compound comprising trialkoxymercaptoalkyl-silanes Download PDF

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Publication number
WO2012085895A1
WO2012085895A1 PCT/IB2011/055953 IB2011055953W WO2012085895A1 WO 2012085895 A1 WO2012085895 A1 WO 2012085895A1 IB 2011055953 W IB2011055953 W IB 2011055953W WO 2012085895 A1 WO2012085895 A1 WO 2012085895A1
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WO
WIPO (PCT)
Prior art keywords
silane coupling
coupling agent
producing
rubber compound
compound
Prior art date
Application number
PCT/IB2011/055953
Other languages
French (fr)
Inventor
Davide Privitera
Original Assignee
Bridgestone Corporation
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 Corporation filed Critical Bridgestone Corporation
Priority to CN201180062205.7A priority Critical patent/CN103269877B/en
Priority to EP11815593.6A priority patent/EP2655092B1/en
Priority to JP2013545626A priority patent/JP5946842B2/en
Priority to US13/993,589 priority patent/US20130331523A1/en
Publication of WO2012085895A1 publication Critical patent/WO2012085895A1/en

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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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/42—Introducing metal atoms or metal-containing groups
    • 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
    • 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
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/45—Heterocyclic compounds having sulfur in the ring
    • C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
    • C08K5/47—Thiazoles
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/548—Silicon-containing compounds containing sulfur
    • 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
    • C08K9/00—Use of pretreated ingredients
    • C08K9/12—Adsorbed ingredients, e.g. ingredients on carriers

Definitions

  • the present invention relates to a tread compound comprising trialkoxymercaptoalkyl-silanes .
  • silica has long been substituted for conventional carbon black as a reinforcing filler, because of its advantages in terms of rolling resistance and wet road-holding performance .
  • Silica is used in combination with silane coupling agents, which bond with silanol groups to prevent the formation of hydrogen bonds between silica particles, and at the same time bond the silica chemically to the polymer base.
  • silane coupling agents As silane coupling agents, mercaptoalkyl-silanes have recently been found to further improve compounds in terms of both rolling resistance and hydrocarbon emissions.
  • trialkoxymercaptoalkyl-silanes have the drawbacks of increasing the viscosity of the compound, and so making it harder to process, impairing wet road-holding performance, and reducing abrasion resistance.
  • a method of producing a rubber compound comprising a first mixing step of mixing at least one cross-linkable unsaturated-chain polymer base, silica, and a silane coupling agent in the mercaptoalkyl-silane class; and a final mixing step, in which a curing system is added to the mix; said method being characterised in that said silane coupling agent is used in adsorbed form on dibenzothiazyl disulphide.
  • the mix comprises 10 to 100 phr of silica with a superficial area of 170 to 230 m 2 /g.
  • the mix comprises 1 to 20 phr of a silane coupling agent in the trialkoxymercaptoalkyl-silane class .
  • said silane coupling agent is used in adsorbed form on 0.5 to 6 phr of said dibenzothiazyl disulphide.
  • said silane coupling agent is also used in adsorbed form on 5 to 10 phr of carbon black.
  • said silane coupling agent has the formula (I)
  • R 1 represents a linear, cyclic or branched alkoxyl group with 1 to 8 carbon atoms
  • R 2 represents a linear, cyclic or branched alkoxyl group with 1 to 8 carbon atoms, or -0- (Y-O) m4-X (where Y represents a linear, cyclic or branched saturated or unsaturated divalent hydrocarbon group with 1 to 20 carbon atoms, X represents a linear, cyclic or branched alkyl group with 1 to 9 carbon atoms, and m4 represents a number of 1 to 40) ; and R 3 represents a linear, cyclic or branched saturated or unsaturated alkylene group with 1 to 12 carbon atoms.
  • said silane coupling agent is in the trialkoxymercaptopropyl-silane class .
  • said silane coupling agent has the formula (II)
  • R 4 is -OCH 2 CH 3 .
  • R 5 is -0 (CH 2 CH 2 0) 5 (CH 2 ) i 3 CH 3
  • control compounds (A-C) and one compound (D) in accordance with the teachings of the present invention were produced. More specifically, a first control compound (A) is one in accordance with the known art, employing a . silane coupling agent not in the trialkoxymercaptoalkyl-silane class; a second control compound (B) is the same as the first, but employing a silane coupling agent in the trialkoxymercaptoalkyl- silane class; and the third control compound (C) is the same as the second, but employing large-area silica.
  • the compounds were produced as follows :
  • a 230-270- litre tangential-rotor mixer was loaded with the cross- linkable unsaturated-chain polymer base, the silica, the carbon black, and the silane coupling agent to a fill factor of 66-72%.
  • silane coupling agent was added in adsorbed form on all the carbon black and on dibenzothiazyl disulphide (MBTS) .
  • the mixer was operated at a speed of 40-60 rpm, and the resulting mix was unloaded on reaching a temperature of 140-160°C.
  • the mix from the first step was mixed again in a mixer operated at 40-60 rpm, and was unloaded on reaching a temperature of 130-150°C.
  • the curing system and zinc oxide were added to the mix from the second step to a fill factor of 63-67%.
  • the mixer was operated at a speed of 20-40 rpm, and the resulting mix was unloaded on reaching a temperature of 100-110°C.
  • Table I shows the compound compositions in parts by weight per hundred parts of total polymer base.
  • Silica 1 is marketed by EVONIK as VN3, and has a surface area of 170 m 2 /g.
  • Silica 2 is marketed by RHODIA as MP200, and has a surface area of 210 m 2 /g and 55 nm particle size.
  • Silane coupling agent 1 is marketed by DEGUSSA as
  • Silane coupling agent 2 is the mercaptosilane of formula I indicated above.
  • Table II shows the test results of each parameter for each compound.
  • Table II The values in Table II are indexed with respect to a value of 100 for compound A.
  • the method according to the invention (compound D) enables silane coupling agents in the trialkoxymercaptoalkyl-silane class to be used in conjunction with large-area silica, without high viscosity compromising the workability of the compound.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)

Abstract

A method of producing a rubber compound, including a first mixing step of mixing at least one cross-linkable unsaturated-chain polymer base, silica, and a silane coupling agent in the mercaptoalkyl-silane class; and a final mixing step, in which a curing system is added to the mix. The silane coupling agent is used in adsorbed form on dibenzothiazyl disulphide.

Description

TREAD COMPOUND COMPRISING TRIALKOXYMERCAPTOALKYL-SILANES
TECHNICAL FIELD
The present invention relates to a tread compound comprising trialkoxymercaptoalkyl-silanes .
BACKGROUND ART
In certain compounds, such as tread compounds, silica has long been substituted for conventional carbon black as a reinforcing filler, because of its advantages in terms of rolling resistance and wet road-holding performance .
Silica is used in combination with silane coupling agents, which bond with silanol groups to prevent the formation of hydrogen bonds between silica particles, and at the same time bond the silica chemically to the polymer base.
As silane coupling agents, mercaptoalkyl-silanes have recently been found to further improve compounds in terms of both rolling resistance and hydrocarbon emissions.
The following, in particular, has proved highly effective :
SH (CH2) 3Si (OCH2CH3) (0 (CH2CH20) 5 (CH2) i3CH3) 2
Alongside the above advantages, however, trialkoxymercaptoalkyl-silanes have the drawbacks of increasing the viscosity of the compound, and so making it harder to process, impairing wet road-holding performance, and reducing abrasion resistance.
One attempt to solve these problems has been to use large-area (170-230 m2/g) silica. This, however, while improving wet road-holding performance and abrasion resistance, has been found to increase viscosity and so further compound viscosity-related problems.
DISCLOSURE OF INVENTION
It is an object of the present invention to provide a compound enabling silane coupling agents in the trialkoxymercaptoalkyl-silane class to be used in conjunction with large-area silica, without incurring processing problems, and without compromising other significant characteristics of the compound.
According to the present invention, there is provided a method of producing a rubber compound, comprising a first mixing step of mixing at least one cross-linkable unsaturated-chain polymer base, silica, and a silane coupling agent in the mercaptoalkyl-silane class; and a final mixing step, in which a curing system is added to the mix; said method being characterised in that said silane coupling agent is used in adsorbed form on dibenzothiazyl disulphide.
Preferably, at said first mixing step, the mix comprises 10 to 100 phr of silica with a superficial area of 170 to 230 m2/g.
Preferably, at said first mixing step, the mix comprises 1 to 20 phr of a silane coupling agent in the trialkoxymercaptoalkyl-silane class .
Preferably, said silane coupling agent is used in adsorbed form on 0.5 to 6 phr of said dibenzothiazyl disulphide.
Preferably, said silane coupling agent is also used in adsorbed form on 5 to 10 phr of carbon black.
Preferably, said silane coupling agent has the formula (I)
R1R2 2Si-R3-SH (I)
where :
R1 represents a linear, cyclic or branched alkoxyl group with 1 to 8 carbon atoms; R2 represents a linear, cyclic or branched alkoxyl group with 1 to 8 carbon atoms, or -0- (Y-O) m4-X (where Y represents a linear, cyclic or branched saturated or unsaturated divalent hydrocarbon group with 1 to 20 carbon atoms, X represents a linear, cyclic or branched alkyl group with 1 to 9 carbon atoms, and m4 represents a number of 1 to 40) ; and R3 represents a linear, cyclic or branched saturated or unsaturated alkylene group with 1 to 12 carbon atoms.
Preferably, said silane coupling agent is in the trialkoxymercaptopropyl-silane class .
Preferably, said silane coupling agent has the formula (II)
SH (CH2) 3SiR4R52 (II)
where :
R4 is -OCH2CH3, and
R5 is -0 (CH2CH20) 5 (CH2) i3CH3
BEST MODE FOR CARRYING OUT THE INVENTION
The following are non-limiting examples for a clearer understanding of the invention.
EXAMPLES
Three control compounds (A-C) and one compound (D) in accordance with the teachings of the present invention were produced. More specifically, a first control compound (A) is one in accordance with the known art, employing a . silane coupling agent not in the trialkoxymercaptoalkyl-silane class; a second control compound (B) is the same as the first, but employing a silane coupling agent in the trialkoxymercaptoalkyl- silane class; and the third control compound (C) is the same as the second, but employing large-area silica. The compounds were produced as follows :
- First mixing step -
Before commencing the mixing operation, a 230-270- litre tangential-rotor mixer was loaded with the cross- linkable unsaturated-chain polymer base, the silica, the carbon black, and the silane coupling agent to a fill factor of 66-72%.
In compound D according to the invention, the silane coupling agent was added in adsorbed form on all the carbon black and on dibenzothiazyl disulphide (MBTS) .
The mixer was operated at a speed of 40-60 rpm, and the resulting mix was unloaded on reaching a temperature of 140-160°C.
- Second mixing step -
The mix from the first step was mixed again in a mixer operated at 40-60 rpm, and was unloaded on reaching a temperature of 130-150°C.
- Third mixing step -
The curing system and zinc oxide were added to the mix from the second step to a fill factor of 63-67%.
The mixer was operated at a speed of 20-40 rpm, and the resulting mix was unloaded on reaching a temperature of 100-110°C.
- Compound compositions -
Table I shows the compound compositions in parts by weight per hundred parts of total polymer base.
TABLE I
Figure imgf000007_0001
* indicates 10 phr of silane coupling agent2 are added to the mix in adsorbed form on 3 phr of MBTS and 7 phr of carbon black.
Silica1 is marketed by EVONIK as VN3, and has a surface area of 170 m2/g.
Silica2 is marketed by RHODIA as MP200, and has a surface area of 210 m2/g and 55 nm particle size.
Silane coupling agent1 is marketed by DEGUSSA as
S175.
Silane coupling agent2 is the mercaptosilane of formula I indicated above.
- Laboratory test results -
The above compounds were tested to determine a number of particularly significant parameters.
Table II shows the test results of each parameter for each compound.
The parameters tested were :
- Mooney Scorch at 130 °C as per ASTM Standard D1646;
- elasticity modulus (E' ) and Tan5 as per ASTM Standard D5992, from which wet road-holding and rolling resistance were extrapolated and indexed with respect to compound A;
- abrasion resistance as per DIN Standard 53516, and indexed with respect to compound A;
- viscosity (MLl'+4' at 130°C) as per ASTM Standard D1646, and indexed with respect to compound A.
The values in Table II are indexed with respect to a value of 100 for compound A.
TABLE II
Figure imgf000008_0001
As shown in Table II, the method according to the invention (compound D) enables silane coupling agents in the trialkoxymercaptoalkyl-silane class to be used in conjunction with large-area silica, without high viscosity compromising the workability of the compound.
As the scorch values show, though MBTS is normally used as an accelerant and so added at the third mixing step, using it at the first mixing step as an adsorbed silane coupling agent support in no way affects curing

Claims

1. A method of producing a rubber compound, comprising a first mixing step of mixing at least one cross-linkable unsaturated-chain polymer base, silica, and a silane coupling agent in the mercaptoalkyl-silane class; and a final mixing step, in which a curing system is added to the mix; said method being characterised in that said silane coupling agent is used in adsorbed form on dibenzothiazyl disulphide.
2. A method of producing a rubber compound, as claimed in Claim 1, characterized in that, at said first mixing step, the mix comprises 10 to 100 phr of silica with a superficial area of 170 to 230 m2/g.
3. A method of producing a rubber compound, as claimed in Claim 2, characterized in that, at said first mixing step, the mix comprises 1 to 20 phr of a silane coupling agent in the trialkoxymercaptoalkyl-silane class .
4. A method of producing a rubber compound, as claimed in one of the foregoing Claims, characterized in that said silane coupling agent is used in adsorbed form on 0.5 to 6 phr of said dibenzothiazyl disulphide.
5. A method of producing a rubber compound, as claimed in one of the foregoing Claims, characterized in that said silane coupling agent is also used in adsorbed form on 5 to 10 phr of carbon black.
6. A method of producing a rubber compound, as claimed in one of the foregoing Claims, characterized in that said silane coupling agent has the formula (I)
R1R2 2Si-R3-SH (I)
where :
R1 represents a linear, cyclic or branched alkoxyl group with 1 to 8 carbon atoms; R2 represents a linear, cyclic or branched alkoxyl group with 1 to 8 carbon atoms, or -0- (Y-0) m4-X (where Y represents a linear, cyclic or branched saturated or unsaturated divalent hydrocarbon group with 1 to 20 carbon atoms, X represents a linear, cyclic or branched alkyl group with 1 to 9 carbon atoms, and m4 represents a number of 1 to 40) ; and R3 represents a linear, cyclic or branched saturated or unsaturated alkylene group with 1 to 12 carbon atoms.
7. A method of producing a rubber compound, as claimed in Claim 6, characterized in that said silane coupling agent is in the trialkoxymercaptopropyl-silane class .
8. A method of producing a rubber compound, as claimed in Claim 7, characterized in that said silane coupling agent has the formula (II)
SH(CH2)3SiRR5 2 (II)
where:
R4 is -OCH2CH3, and
R5 is -0(CH2CH20) 5(CH2)i3CH3
9. A tread compound, characterized by being produced using the method as claimed in one of the foregoing Claims.
10. A tread, characterized by being produced from the compound as claimed in Claim 9.
11. A tyre comprising a tread as claimed in Claim
10.
PCT/IB2011/055953 2010-12-23 2011-12-23 Tread compound comprising trialkoxymercaptoalkyl-silanes WO2012085895A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN201180062205.7A CN103269877B (en) 2010-12-23 2011-12-23 Comprise the tread compounds of tri-alkoxy mercaptoalkyl-silane
EP11815593.6A EP2655092B1 (en) 2010-12-23 2011-12-23 Tread compound comprising trialkoxymercaptoalkyl-silanes
JP2013545626A JP5946842B2 (en) 2010-12-23 2011-12-23 Trialkoxymercaptoalkyl-silane-containing tread mixture
US13/993,589 US20130331523A1 (en) 2010-12-23 2011-12-23 Tread compound comprising trialkoxymercaptoalkyl-silanes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITTO2010A001056 2010-12-23
ITTO2010A001056A IT1403426B1 (en) 2010-12-23 2010-12-23 COMPOUND COMPRESS FOR TRIALCOSSIMERCAPTOALCHIL-SILANI

Publications (1)

Publication Number Publication Date
WO2012085895A1 true WO2012085895A1 (en) 2012-06-28

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PCT/IB2011/055953 WO2012085895A1 (en) 2010-12-23 2011-12-23 Tread compound comprising trialkoxymercaptoalkyl-silanes

Country Status (6)

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US (1) US20130331523A1 (en)
EP (1) EP2655092B1 (en)
JP (1) JP5946842B2 (en)
CN (1) CN103269877B (en)
IT (1) IT1403426B1 (en)
WO (1) WO2012085895A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITRM20120646A1 (en) * 2012-12-18 2014-06-19 Bridgestone Corp METHOD FOR THE PREPARATION OF RUBBER COMPOUNDS FOR TIRES

Families Citing this family (1)

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Publication number Priority date Publication date Assignee Title
KR101832064B1 (en) * 2016-08-18 2018-04-04 금호타이어 주식회사 Rubber composite for tread part of tyre

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US5798009A (en) * 1994-12-27 1998-08-25 Bridgestone Corporation Foamed rubber compositions for tires and pneumatic tire using the same
US6096833A (en) * 1996-12-16 2000-08-01 Bridgestone Corporation Rubber composition and pneumatic tire using said rubber composition
US6095217A (en) * 1996-07-11 2000-08-01 Bridgestone Corporation Pneumatic tire including cap layer and base layer
US6180703B1 (en) * 1997-02-28 2001-01-30 The Yokohama Rubber Co., Ltd. Rubber composition
US6376587B1 (en) * 1998-06-25 2002-04-23 Bridgestone Corporation Rubber composition for tire tread and pneumatic tire using said rubber composition
US20070185239A1 (en) * 2003-12-10 2007-08-09 Diego Tirelli Crosslinkable elastomeric composition and tire for vehicle wheels comprising the same
US20080161458A1 (en) * 2006-12-29 2008-07-03 Shaun Fox Elastomeric composition containing multiple silane coupling agents
WO2009092811A1 (en) * 2008-01-24 2009-07-30 Bridgestone Corporation Mix comprising trialkoxymercaptoalkyl-silanes
EP2105461A1 (en) * 2007-01-17 2009-09-30 Bridgestone Corporation Rubber composition and pneumatic tire using the same
EP2128186A1 (en) * 2007-03-27 2009-12-02 Bridgestone Corporation Process for producing rubber composition for tire tread

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JP2002508425A (en) * 1997-12-15 2002-03-19 エクソンモービル・ケミカル・パテンツ・インク Transparent and colorable elastomeric composition
JPH11240982A (en) * 1998-02-25 1999-09-07 Bridgestone Corp Rubber composition and pneumatic tire using the same
JP2005232354A (en) * 2004-02-20 2005-09-02 Bridgestone Corp Rubber composition and tire using it
CN101117408A (en) * 2007-07-14 2008-02-06 昊华南方(桂林)橡胶有限责任公司 All-steel giant-scale engineering tyre base glue and all-steel giant-scale engineering tyre using the same

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Publication number Priority date Publication date Assignee Title
US5798009A (en) * 1994-12-27 1998-08-25 Bridgestone Corporation Foamed rubber compositions for tires and pneumatic tire using the same
US6095217A (en) * 1996-07-11 2000-08-01 Bridgestone Corporation Pneumatic tire including cap layer and base layer
US6096833A (en) * 1996-12-16 2000-08-01 Bridgestone Corporation Rubber composition and pneumatic tire using said rubber composition
US6180703B1 (en) * 1997-02-28 2001-01-30 The Yokohama Rubber Co., Ltd. Rubber composition
US6376587B1 (en) * 1998-06-25 2002-04-23 Bridgestone Corporation Rubber composition for tire tread and pneumatic tire using said rubber composition
US20070185239A1 (en) * 2003-12-10 2007-08-09 Diego Tirelli Crosslinkable elastomeric composition and tire for vehicle wheels comprising the same
US20080161458A1 (en) * 2006-12-29 2008-07-03 Shaun Fox Elastomeric composition containing multiple silane coupling agents
EP2105461A1 (en) * 2007-01-17 2009-09-30 Bridgestone Corporation Rubber composition and pneumatic tire using the same
EP2128186A1 (en) * 2007-03-27 2009-12-02 Bridgestone Corporation Process for producing rubber composition for tire tread
WO2009092811A1 (en) * 2008-01-24 2009-07-30 Bridgestone Corporation Mix comprising trialkoxymercaptoalkyl-silanes

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Publication number Priority date Publication date Assignee Title
ITRM20120646A1 (en) * 2012-12-18 2014-06-19 Bridgestone Corp METHOD FOR THE PREPARATION OF RUBBER COMPOUNDS FOR TIRES
WO2014097195A1 (en) * 2012-12-18 2014-06-26 Bridgestone Corporation Method of producing rubber tyre compounds
US9592704B2 (en) 2012-12-18 2017-03-14 Bridgestone Corporation Method of producing rubber tyre compounds

Also Published As

Publication number Publication date
US20130331523A1 (en) 2013-12-12
CN103269877B (en) 2015-12-16
CN103269877A (en) 2013-08-28
JP2014507504A (en) 2014-03-27
JP5946842B2 (en) 2016-07-06
IT1403426B1 (en) 2013-10-17
EP2655092A1 (en) 2013-10-30
EP2655092B1 (en) 2014-11-05
ITTO20101056A1 (en) 2012-06-24

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