EP1791903A1 - Verbrennungsverzögernde zusammensetzung - Google Patents

Verbrennungsverzögernde zusammensetzung

Info

Publication number
EP1791903A1
EP1791903A1 EP05802600A EP05802600A EP1791903A1 EP 1791903 A1 EP1791903 A1 EP 1791903A1 EP 05802600 A EP05802600 A EP 05802600A EP 05802600 A EP05802600 A EP 05802600A EP 1791903 A1 EP1791903 A1 EP 1791903A1
Authority
EP
European Patent Office
Prior art keywords
tetramethyl
nitroxide
tert
crosslinking
peroxide
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.)
Ceased
Application number
EP05802600A
Other languages
English (en)
French (fr)
Inventor
Fabien Debaud
Jacques Kervennal
Alfredo Defrancisci
Olivier Guerret
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arkema France SA
Original Assignee
Arkema France SA
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 Arkema France SA filed Critical Arkema France SA
Publication of EP1791903A1 publication Critical patent/EP1791903A1/de
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • 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
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups

Definitions

  • the present invention relates to the prevention of roasting before the crosslinking of a thermoplastic and / or elastomer composition by peroxides and more particularly to a composition comprising a nitroxide and at least one organic peroxide, for delaying roasting.
  • Patent EP 0837 080 describes a method of grafting a functional monomer, in particular maleic anhydride, onto a thermoplastic polymer in the presence of a nitroxide, the function of which is to prevent crosslinking during the grafting.
  • scorch retarding compositions comprising a nitroxide, a crosslinking promoter and an organic peroxide.
  • R 1 , R 2 , R 5 and R 6 represent an alkyl group of 1 to 4 carbons and R 3 and R 4 represent an alkyl group of 1 to 4 carbons or are connected and represent a group - CH 2 -CHX- CH 2 - with X being a hydroxy, methoxy, cyano, phenylcarbonyloxy, carboxyl or methoxycarbonyl group.
  • TEMPO 2,2,6,6-tetramethyl-1-piperidinyloxy
  • HTEMPO 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinyloxy
  • TEMPO 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinyloxy
  • nitroxides of formula I are used in admixture with an organic peroxide.
  • organic peroxide also known as DCP
  • bis ( ⁇ -tert-butylperoxyisopropyl) benzene in combination with a compound of general formula I are preferred as scorch-retarding agents.
  • the organic peroxide and the compound of general formula I are used in proportions by weight ranging from 1: 0.02 to 1: 1 and advantageously from 1: 0.1 to 1: 0.5. Apart from these proportions, if the content of the compound of the general formula I in terms of peroxide is less than 1: 0.02, the reduction effect of the roasting is less marked; if it is greater than 1: 1, then a substantial decrease in the crosslinking density is noted.
  • the weight proportion of organic peroxide is normally between 0.3 and 5 parts per 100 parts by weight of polyethylene and advantageously between e-1-and-3-parts ⁇
  • Table 1 of the patent application JP 11-49865 shows that the addition in 500 g of low density polyethylene of 12.5 g of DCP with 2.5 g (0.5%) or 5 g ( 1, 0%) of TEMPO or HTEMPO makes it possible to increase the roasting time at 145 ° C. expressed as time A (time necessary to reach 10% of the maximum torque) and time B (time required to reach the value of torque of 0.4 kgf.cm) compared to the addition of 12.5 g of DCP alone.
  • time A time necessary to reach 10% of the maximum torque
  • time B time required to reach the value of torque of 0.4 kgf.cm
  • DCP with 2.5 g (0.5%) or 5 g (1.0%) of TEMPO or HTEMPO causes a very marked decrease in the crosslinking density expressed as a maximum value of the torque at 180 ° C., compared with with the addition of DCP alone.
  • the reduction of the final crosslinking density represents a major drawback.
  • the crosslinking density is an indication of the mechanical properties of the final part.
  • a decrease in the crosslinking density most likely indicates a decrease in mechanical properties. It may be envisaged in certain cases to compensate for this reduction in crosslinking density by increasing the amount of crosslinking system (peroxide), to the detriment of the economic aspect and the formation of higher amounts of decomposition products.
  • the Applicant has discovered that this loss of crosslinking density can be avoided by using a lower amount of nitroxide in a composition comprising a nitroxide and at least one organic peroxide.
  • a nitroxide in low proportion with at least one organic peroxide leads to a composition for retarding the roasting during the crosslinking of thermoplastic and / or elastomeric compositions with peroxides, without deleterious effect on the final crosslinking density. It thus makes it possible to obtain curing / crosslinking compositions which give good properties of the final product with significant productivity.
  • the presence of residual nitroxide in the crosslinked rubber piece gives this piece increased resistance to aging.
  • the subject of the present invention is therefore a composition for retarding roasting comprising a nitroxide and at least one organic peroxide, characterized in that the organic peroxide (s) is (are) used in proportions by weight ranging from from 1: 0.01 to 1: 0.1 relative to the amount of nitroxide present.
  • the (or) peroxide (s) is (are) used in proportions by weight ranging from 1: 0.03 to 1: 0.05 relative to the amount of nitroxide present.
  • the nitroxide is selected from the group consisting of 2,2,6,6-tetramethyl-1-piperidinyloxy (generally marketed as TEMPO), 4-hydroxy 2,2,6,6-tetramethyl-1-piperidinyloxy (generally marketed under the name 4-hydroxy-TEMPO), 4-methoxy-2,2,6,6-tetramethyl-1-piperidinyloxy (commonly known as 4-methoxy-TEMPO), 4-oxo-2,2,6,6 1-tetramethyl-1-piperidinyloxy (commonly known as 4-oxo-TEMPO), 2,2,5,5-tetramethyl-1-pyrrolidinyloxy, bis (1-oxyl-2,2,6,6-tetramethylpiperidin-4-yl) sebacate (marketed under the trademark CXA 5415 by the company Ciba Specialty Chemical), 1 -piperidinyloxy-4,4 '- (1,10-dioxo-10-decanediyl) bis (oxy)) bis (2,2,
  • the organic peroxide (s) is (are) chosen from dicumyl peroxide, 1,3-1,4 bis (tert-butylperoxyisopropyl) benzene; 1,1 'di (tert-butylperoxy) -3,3,5-trimethylcyclohexane; n-butyl-4,4'-di (tert-butylperoxy) valerate; 2,5-dimethyl-2,5-di- (tert-butylperoxy) hexane.
  • Organic peroxides such as 1,3-1,4 bis (tert-butylperoxyisopropyl) benzene, 1,1 'di (tert-butylperoxy) -3,3,5-trimethylcyclohexane, or n-butyl-4,4 '-di (tert-butylperoxy) valerate are particularly preferred.
  • the composition comprises 1, 3-1, 4 bis (tert-butylperoxyisopropyl) benzene and 4-hydroxy-TEMPO in a weight ratio ranging from 1: 0.01 to 1: 0.1, from preferably 1: 0.025 to 1: 0.075.
  • the composition comprises 1,3-1,4 bis (tert-butylperoxyisopropyl) benzene and di-TEMPO sebacate in a weight ratio ranging from 1: 0.01 to 1: 0.1, from preferably 1: 0.025 to 1: 0.075.
  • the composition comprises 1,1 'di (tert-butyliperoxy) -373,5-trimethylhexane-and-4-hydr-ox-y-TE-MP-O-in-a-recap.ori Mass ratio ranging from 1: 0.01 to 1: 0.1, preferably from 1: 0.025 to 1: 0.075.
  • the composition comprises n-butyl-4,4'-di (tert-butylperoxy) valerate and 4-hydroxy TEMPO in a weight ratio ranging from 1: 0.01 to 1: 0.1, preferably from 1: 0.025 to 1: 0.075.
  • the composition comprises n-butyl-4,4'-di (tert-butylperoxy) valerate and di-TEMPO sebacate in a weight ratio ranging from 1: 0.01 to 1: 0.1. preferably from 1: 0.025 to 1: 0.075.
  • compositions according to the invention may be mixed with a crosslinking promoter chosen from the group consisting of compounds containing at least one double bond which may be bifunctional or polyfunctional, such as, for example, bifunctional vinyl monomers, monomers bifunctional allylic, polyfunctional vinyl monomers or polyfunctional allylic monomers.
  • a crosslinking promoter chosen from the group consisting of compounds containing at least one double bond which may be bifunctional or polyfunctional, such as, for example, bifunctional vinyl monomers, monomers bifunctional allylic, polyfunctional vinyl monomers or polyfunctional allylic monomers.
  • compositions according to the invention can be advantageously used to control the crosslinking in a crosslinking process of a thermoplastic polymer and / or elastomer that can be crosslinked by means of a peroxide.
  • the present invention also provides a crosslinkable composition
  • a crosslinkable composition comprising a thermoplastic polymer and / or an elastomeric polymer capable of being cross-linked by means of a peroxide, a nitroxide and at least one organic peroxide, the amount by weight of organic peroxide (s) ranging from 1: 0.01 to 1: 0.1 relative to the amount of nitroxide present, preferably from 1: 0.025 to 1: 0.075.
  • the organic peroxide (s) is (are) preferably between 0.2 and 5 parts and advantageously between 1 and 4 parts per 100 parts by weight of polymer.
  • the nitroxide and the peroxides are preferably those used for the scorch retarding composition.
  • the crosslinkable composition may further contain a crosslinking promoter as defined above.
  • the present invention also provides a process for crosslinking a crosslinkable composition
  • a crosslinkable composition comprising a thermoplastic polymer and / or an elastomeric polymer capable of being crosslinked by means of a peroxide, wherein said polymer is mixed in the presence of a nitroxide and at least one an organic peroxide, the amount by weight of organic peroxide (s) ranging from 1: 0.01 to 1: 0.1 with respect to the amount of -nitroxide-preferably de-1- ⁇ ⁇ 0 025 to 1 -: - 0.0 to 75, -per proceedings- thereby control the crosslinking.
  • the present invention also provides molded articles or extrusions such as wires, electrical cables obtained from a crosslinkable composition defined above.
  • thermoplastic and / or elastomeric polymers considered in the present invention can be defined as natural or synthetic polymers which have a thermoplastic and / or elastomeric character and which can be crosslinked (cured) under the action of a crosslinking agent. .
  • a crosslinking agent for Rubber World, "Elastomer Crosslinking with Diperoxyketals", October 1983, pages 26-32, and in Rubber and Plastic News, "Organic Peroxides for Rubber Crosslinking", September 29, 1980, pages 46-50, the crosslinking action is described. and crosslinkable polymers.
  • Polyolefins suitable for the present invention are described in Modern Plastics Encyclopedia 89, pp. 63-67, 74-75.
  • polymers and / or elastomers By way of example of polymers and / or elastomers, mention may be made of low density linear polyethylene, low density polyethylene, high density polyethylene, chlorinated polyethylene, and ethylene-propylene-diene terpolymers (EPDM). , ethylene-vinyl acetate copolymers, ethylene-propylene copolymers, silicone rubber, natural rubber (NR), polyisoprene (IR), polybutadiene (BR), acrylonitrile-butadiene copolymers (NBR) , styrene-butadiene copolymers (SBR). chlorosulfonated polyethylene or fluoroelastomers.
  • NR natural rubber
  • IR polyisoprene
  • BR polybutadiene
  • NBR acrylonitrile-butadiene copolymers
  • SBR styrene-butadiene copolymers
  • ethylene (meth) acrylate copolymers Mention may also be made of ethylene (meth) acrylate copolymers and ethylene-glycidyl methacrylate copolymers.
  • compositions retarding roasting and crosslinkable compositions according to the invention may comprise antioxidants, stabilizers, plasticizers and inert fillers such as silica, clay or calcium carbonate.
  • the crosslinking temperature is between 140 and 250 ° C. and preferably between 160 and 200 ° C.
  • the crosslinking process is carried out in the presence of a nitroxide and at least one organic peroxide as defined for the crosslinkable composition.
  • Transformation of the crosslinkable compositions into molded or extruded articles can be carried out during or after the crosslinking.
  • EPDM ethylene-propylene-diene terpolymer marketed by Enichem OHT: 4-hydroxy TEMPO SDT: di-TEMPO sebacate Luperox F: 1, 3-1, 4 bis (tert-butylperoxyisopropyl) benzene
  • Luperox 230 n-butyl-4,4'-di (tert-butylperoxy) valerate)
  • Luperox 231 1,1 'di (tert-butylperoxy) -3,3,5-trimethylcyclohexane
  • Luperox 101 2,5-dimethyl- 2,5-di- (tert-butylperoxy) hexane
  • the crosslinking density (MH) and the crosslinking time (t 90 ) of the tested mixtures were measured at 170 or 180 ° C. using a Monsanto ODR rheometer. 2000 E (Alpha Technologies, oscillation arc 3 °, oscillation frequency 100 cycles / min).
  • the roasting time (t s5 ) was measured at 110 or 130 ° C. using a Mooney MV 2000 viscometer (Alpha Technologies).
  • M ⁇ maximum value of the torque obtained from the curve recorded by the rheometer, expressed in N. m. It indicates the level of crosslinking density.
  • t 90 time required to reach 90% of the maximum torque.
  • This is the crosslinking time expressed in min: st s5 time required at a given temperature for the nominal torque to increase by 5 Mooney units.
  • the temperatures selected are those at which the compounding operation typically takes place, namely 130 ° C. for Luperox F and Luperox 101, and 110 ° C. for Luperox 231 and Luperox 230. The examples are all carried out according to the following procedure:
  • EPDM compound 300 g are mixed in the presence of a crosslinking system on a roller mixer at 80 ° C for 5 minutes.
  • the contents in Organic peroxide and nitroxide are expressed in parts or milli parts by weight per 100 parts by weight of polymer (phr or mphr).
  • the sample is then placed in the rheometer chamber or viscometer to perform the measurements of MH,

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Polymerisation Methods In General (AREA)
EP05802600A 2004-09-22 2005-09-16 Verbrennungsverzögernde zusammensetzung Ceased EP1791903A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0410002A FR2875502B1 (fr) 2004-09-22 2004-09-22 Composition retardant le grillage
PCT/FR2005/002295 WO2006032765A1 (fr) 2004-09-22 2005-09-16 Composition retardant le grillage

Publications (1)

Publication Number Publication Date
EP1791903A1 true EP1791903A1 (de) 2007-06-06

Family

ID=34948829

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05802600A Ceased EP1791903A1 (de) 2004-09-22 2005-09-16 Verbrennungsverzögernde zusammensetzung

Country Status (7)

Country Link
US (1) US7829634B2 (de)
EP (1) EP1791903A1 (de)
JP (1) JP5000518B2 (de)
KR (1) KR101184239B1 (de)
CN (1) CN101023127B (de)
FR (1) FR2875502B1 (de)
WO (1) WO2006032765A1 (de)

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EP2118195B1 (de) * 2007-02-05 2014-06-04 Dow Global Technologies LLC Vernetzbare polyethylenzusammensetzung, verfahren zu deren herstellung und artikel daraus
JP4236686B2 (ja) 2007-04-19 2009-03-11 横浜ゴム株式会社 変性ブチルゴム組成物
US8310813B2 (en) * 2007-04-25 2012-11-13 Nippon Chemi-Con Corporation Sealing material for electrolytic capacitor and electrolytic capacitor employing the sealing material
JP4420095B2 (ja) 2007-10-01 2010-02-24 横浜ゴム株式会社 変性ブチルゴム組成物
US8686071B2 (en) 2010-07-01 2014-04-01 The Goodyear Tire & Rubber Company Rubber composition, preparation and tire with component
FR2963352B1 (fr) * 2010-07-27 2014-03-14 Arkema France Procede pour preparer un cable et utilisation de peroxydes organiques pour reduire l'etape de degazage dans un procede pour preparer un cable
US8584725B2 (en) 2010-09-17 2013-11-19 The Goodyear Tire & Rubber Company Rubber composition, preparation and tire with component
CN103206541B (zh) * 2013-04-23 2015-07-15 广州机械科学研究院有限公司 一种夹布油封及其制备方法与应用
FR3022543B1 (fr) 2014-06-20 2021-05-14 Lafarge Sa Nouveau beton a ultra haute performance
JP6830063B2 (ja) * 2014-12-09 2021-02-17 アーケマ・インコーポレイテッド 大気酸素の存在下でポリマーを架橋させるための組成物および方法
JP6707541B2 (ja) * 2014-12-09 2020-06-10 アーケマ・インコーポレイテッド 大気酸素の存在下においてポリマーを架橋させるための組成物および方法
GB2561796A (en) 2016-02-08 2018-10-24 Shell Int Research Method for providing zonal isolation in an underground wellbore
KR102544970B1 (ko) 2016-03-30 2023-06-20 다우 글로벌 테크놀로지스 엘엘씨 메틸-라디칼 포착제를 갖는 가교결합성 폴리머 조성물 및 이로부터 제조된 물품
BR112020006330B1 (pt) 2017-09-30 2023-03-07 Dow Global Technologies Llc Composição, composição reticulada e artigo
US11898026B2 (en) 2017-11-08 2024-02-13 Dow Global Technologies Llc Air-curable ethylene/alpha-olefin/diene interpolymer composition
FR3084369B1 (fr) * 2018-07-25 2021-10-29 Arkema France Composition comprenant un melange de peroxydes organiques dont le 1,3-1,4-bis (tert-butylperoxy isopropyl)benzene pour la reticulation de polymeres reticulables
IT202100014606A1 (it) 2021-06-04 2022-12-04 Rubber Conv Srl Additivo devulcanizzante, relativo metodo di devulcanizzazione e prodotto devulcanizzato
WO2024031619A1 (en) * 2022-08-12 2024-02-15 Dow Global Technologies Llc Air curable ethylene/alpha-olefin interpolymer compositions

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Also Published As

Publication number Publication date
WO2006032765A8 (fr) 2007-04-12
WO2006032765A1 (fr) 2006-03-30
CN101023127A (zh) 2007-08-22
JP5000518B2 (ja) 2012-08-15
FR2875502B1 (fr) 2007-01-05
KR20070054654A (ko) 2007-05-29
JP2008513592A (ja) 2008-05-01
US20080051496A1 (en) 2008-02-28
FR2875502A1 (fr) 2006-03-24
CN101023127B (zh) 2013-03-27
US7829634B2 (en) 2010-11-09
KR101184239B1 (ko) 2012-09-21

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