WO2013050579A1 - Polysiloxanes à restauration contrôlée, procédé de préparation et utilisation desdits polysiloxanes - Google Patents

Polysiloxanes à restauration contrôlée, procédé de préparation et utilisation desdits polysiloxanes Download PDF

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Publication number
WO2013050579A1
WO2013050579A1 PCT/EP2012/069803 EP2012069803W WO2013050579A1 WO 2013050579 A1 WO2013050579 A1 WO 2013050579A1 EP 2012069803 W EP2012069803 W EP 2012069803W WO 2013050579 A1 WO2013050579 A1 WO 2013050579A1
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WO
WIPO (PCT)
Prior art keywords
group
methyl
silicone polymer
oxime
blocked
Prior art date
Application number
PCT/EP2012/069803
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English (en)
Inventor
Etienne DELEBECQ
François GANACHAUD
Original Assignee
Delphi Connection Systems Holding France
Centre National De La Recherche Scientifique - Cnrs
Universite Montpellier Ii Sciences Et Techniques
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Application filed by Delphi Connection Systems Holding France, Centre National De La Recherche Scientifique - Cnrs, Universite Montpellier Ii Sciences Et Techniques filed Critical Delphi Connection Systems Holding France
Publication of WO2013050579A1 publication Critical patent/WO2013050579A1/fr

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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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • 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
    • C08K5/544—Silicon-containing compounds containing nitrogen
    • C08K5/5465—Silicon-containing compounds containing nitrogen containing at least one C=N bond
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
    • H01R13/00—Details of coupling devices of the kinds covered by groups H01R12/70 or H01R24/00 - H01R33/00
    • H01R13/46—Bases; Cases
    • H01R13/52—Dustproof, splashproof, drip-proof, waterproof, or flameproof cases
    • H01R13/5205—Sealing means between cable and housing, e.g. grommet
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
    • H01R13/00—Details of coupling devices of the kinds covered by groups H01R12/70 or H01R24/00 - H01R33/00
    • H01R13/46—Bases; Cases
    • H01R13/52—Dustproof, splashproof, drip-proof, waterproof, or flameproof cases
    • H01R13/5216—Dustproof, splashproof, drip-proof, waterproof, or flameproof cases characterised by the sealing material, e.g. gels or resins

Definitions

  • the instant invention relates to controlied-healing po 1 ys i loxar.es intended notably to be used as additives for sealing oints .
  • the invention relates also to a process for their preparation and to the use of said polymers.
  • Connectors are notably used for connecting an electrical, optical or electro-optical apparatus to another, and can be found in any kind of electrical, optical or electro-optical devices.
  • Such connectors can , for example, be of the type comprising an electrically insulative housing in which electrical wires or optical fibres are inserted.
  • an electrical connector is taken as an example, but the person skilled in the art will easily transpose this example into connectors for optical or electro-optical applications.
  • a given class of connectors therefore comprises a so-called mat sealing joint disposed between a housing body (main part of the housing) and a rear grid (rear part of the housing) . Sealing is performed peripherally, for example by the sealing joint being compressed on the housing . Further, the mat sealing j oint is also designed to provide sealing on each cable.
  • the cable insertion step is an aggressive step for the mat sealing joint, which may cause damages to the sealing joint, whereby the sealing efficiency of the sealing joint can be highly affected after several cable insertion/removal operations .
  • Said controlled-healing polysiloxane is intended to be used on at least a part of the surface of sealing joint for improving sealing efficiency. Under controlled conditions, such as moisture and temperature, said polymer is capable to cross-link, thereby ensuring a "self repairing" of the damaged sealing j oint .
  • a controlled-healing polysiloxane which is a silicone polymer with a protected isocyanate having the general formula (I) according to claim 1.
  • the invention relates to polysiloxanes with a protected isocyanate having the following general formula (I) :
  • A is an alkanediyi group in Ci-Cio, possibly substituted, preferably an alkanediyi group in C1-C , even more preferably a propanediyl group;
  • B is a protecting group which can be released at a temperature ranging from 50 to 200 °C, preferably from
  • each X represents independently hydrogen or a C1-C4- alkyl group, preferably a methyl or ethyl group;
  • p is an integer ranging from 2 to 850 preferably from
  • n is an integer higher than 1, preferably higher than
  • the molecular mass should preferentially not be above around 60000g/mol . If p is above 850, too important bodying up can occur.
  • the man skilled in the art can modified the final mechanical properties of the cross-linked polymer by varying the number of xsocyanate groups, i.e., the n value.
  • B is selected from the group comprising N-alkyl-aniline , ketone oximes such as 2- butanone oxime, methyl n-amyl ketone oxime, methyl isoamyl ketone oxime, cyclohexanone oxime, methyl isopropyl ketone oxiine , methyl isobutyl ketone oxime, di i sobutyl ketone oxime, methyl tert -butyl ketone oxime, diisopropyl ketone oxime, 2,2,6, 6- Letramethylcyclohexanonc oxime or tetramethylcyclobutanedxone monooxime ; thiols such as thiophenol or 2-mercaptopyridine; CH-azidic compounds such as dimethyl malonate, diethyl malonate, methyl acetoacetate, ethyl acetoacetate , ethyl
  • B groups are mono-or di-alkyl- substituted pyrazole, di-a i. kyl-ketoxyrne ; and mixtures thereof.
  • B is selected from the group comprising dimethylpyrazole , methylethylketoxyme , and mixtures thereof.
  • the polysiloxane according to the invention has the following formulas ( la) or (lb) :
  • polymers according to the invention are 3, 5-dimethylpyrazole-blocked isocyanatopropyltriethoxysilane having the following formula (l ' ) or methylethylketoxime-blocked
  • Said polymers are prepared by a two-steps process .
  • the isocyanate group of a si lane monomer is blocked and in the second step the blocked monomer is linked to a macromolecular structure, e.g. a polysiloxane . .
  • Blocking reaction In the first step the isocyanate group of a si lane monomer is blocked and in the second step the blocked monomer is linked to a macromolecular structure, e.g. a polysiloxane . . Blocking reaction
  • X, A, B , n and p are such as mentioned above.
  • the poiycon.densaLion step is carried out in the presence of a catalyst.
  • a catalyst Any product capable of catalyzing the a 1 koxy- silanoi reaction can e used.
  • catalysts can be zirconium and aluminium derivatives, such as those described in GB2144758 and FR2856694; tin catalysts, such as those described in GB841825, GB1097379, FR2557582, EP0235049, US 3862919 and BE842305; calcium and magnesium catalysts, such as those described in US 6818721; titane, as described in US4111890, US5698653, US3689454 and US4722967 ; or basic catalysts, such as alkali metal hydroxide or amine.
  • the amount of catalyst will depend on the type of catalyst used. Generally, said amount will be from 0.01 to 1.5 mo1% , preferably from 0.1 to 0.8 mol% with respect to the silanol content.
  • the catalyst is tin C ⁇ -
  • Ci2-alkanoate preferably tin hexanoate, tin heptanoate or tin octanoate.
  • the temperature of the polycondensation will be between 0 and 80°C, preferably from 20 to 50°C.
  • the polycondensation is stopped when the desired molecular weight is obtained.
  • the man skilled in the art can use any method for stopping the polycondensation reaction.
  • the catalyst activity can be quenched, for example using a ether crown, tetraglyme, phosphine, tertiary amine, phosphazene, carbene.
  • phosphines and ether crown can be found in WO2011/018161, in particular, it can e mentioned 12-crown- , 15-crown-5, 18-crown-6, dibenzo 18 -crown- 6, mono- or di-hyd ogen phosphine, tri- (C1-C12- aikyl ) -phosphines such as tri-ethyl phosphine, tri-methyl phosphine, tri-isopropyl phosphine, tri-hexyl phosphine, tri-cyclohexyl phosphine; arylphosphines such as triphenyl phosphine, tritolylphosphine .
  • Tertiary amines can also be used as quenching agents.
  • suitable tertiary amines are tris [2- ( dimethylamino ) ethyl ] amine ; ⁇ , ⁇ , ⁇ ' , ⁇ ' ' , ⁇ ' ' - pentamethyldiethylenetriamine; 1,1,4,7,10, 10- hexamethyltriethylenetetramine; N, N ' -diethyl-N, N ' - dimethylethylenediamine ; N, -diethyl-N ' , N ' - dimethylethylenediamine ; N , , N ' , ' - tetraethylethylenediamine .
  • Ethers which can be used as quenching agents for example diethylene glycol dimethyl ether; tetraethylene glycol dimethyl ether; triethylene glycol dimethyl ether; l-tert-butoxy-2-methoxyethane ; ethylene glycol diethyl ether; diethylene glycol diethyl ether.
  • Said quenching agents can be used alone or in combination with each others.
  • the amount of quenching agent depends on its nature. For examples, when ⁇ , ⁇ , ⁇ ', ⁇ ' ', ⁇ ' ' - pentamethyldiethylenetriamine is used as a quenching agent, it is used within a range from 50% to 500% by weight with respect to the catalyst weight/ tetraethylene glycol dimethyl ether is used in an amount ranging from 50% to 500% by weight with respect to the catalyst weight.
  • the poiycondensation reaction is carried out with an alkoxylated polydimethylsiloxane, preferably an ethoxylated polydimethylsiloxane, to enhance the poiycondensation.
  • Each X' representing independently a Ci-C 4 -alkyl group, preferably a methyl or ethyl group.
  • a capping reaction can be carried out. Without being linked by any theory, the inventors believe that the capping reaction allows stabilizing the polysiloxane by avoiding a condensation of molecules of polysiloxane on other molecules of polysiloxane. The product is thus more stable.
  • X and X 1 being as defined above, preferably, X and X' are methyl or ethyl.
  • the blocked isocyanate groups of the siloxane polymer are de-blocked by temperature rise and then the siloxane polymers are able to cross-link with formation of carbon dioxide.
  • the de-blocked isocyanate group of a polymer chain reacts with an amine radical of the same polymer chain or of another polymer chain forming bridges between the polymer chains, according to the following reactio : I. Deblocking reaction
  • Said reaction is carried out in- the. presence of moisture and at a temperature ranging from 50 to 200 °C, preferably from. 80 to 150 °C, and even more preferably from .90 to 120°C.
  • the invention also relates to composition
  • composition comprising the silicone polymer with a protected isocyanate group having the following general formula (I) as disclosed above with additives and/or solvent.
  • additives which can be used in the composition according to the invention are colors, inks, plasticizers , etc.
  • solvent examples include alkanes (for instance pentane, hexane, heptanes), ethers (such as diethyl ether, tetrahydro uran) , and aromatic solvent (toluene, xylene) .
  • alkanes for instance pentane, hexane, heptanes
  • ethers such as diethyl ether, tetrahydro uran
  • aromatic solvent toluene, xylene
  • composition or the polymer according to the invention can be applied on silicone surfaces and cross- linked in-situ by heating in presence of moisture.
  • silicone mat seal joint which has been damaged (e.g. cracks) .
  • the polymer will enter in said cracks and after cross-linking, will heal the cracks.
  • this polymer ca be chosen for cross-linking in the condition of use of the motorized vehicle.
  • the polymer will be formulated such that it is able to cross-link at the temperature in the vehicle engine compartment when the vehicle is running.
  • IPTES MEKO MEKO-blocked IPTES A 100 ml two-necked flask equipped with magnetic stirrer, argon inlet, condenser was charged with 3,87 g (44 mmol) of methylethyl ketoxime (MEKO) . The reactants were heated to 3 ° C and 10 g (40 mmol) of isocyanatopropyl triethoxysilane (IPTES) was dropwise added to the reaction mixture. The reaction was carried out until no NCO peak (2273 cm "1 ) could be detected in the IR spectrum.
  • IPTES isocyanatopropyl triethoxysilane
  • Molecular weights were determined through Steric Exclusion Chromatography (SEC) equipped with RI (refractive index) and UV detectors, both of them show one peak of polymer at 890s with similar weight distribution.
  • the DMP-blocked IPTES was detected in RI and UV at 1110s and tetraglyme was only detected with RI detector at 1140s.
  • Steric Exclusion Chromatography (SEC) analyses were performed using a Spectra-Physics apparatus, equipped with a set of PL gel (5 mm) MIXED-C columns, from Polymer Laboratories and two detectors, refractive index and UV absorption.
  • the eluent was tetrahydrof ran at a flow rate of 1 mL.min "1 .
  • the calibration curve was established using Polystyrene standards from Polymer Laboratories and toluene as flowmarker.
  • the RI detection is represented in Figure 5.
  • the polymer peak (890s) analysis was as follows:
  • Mz+1 ( ⁇ i + iN i+1 x M i+ i 3 ) / ( ⁇ i+ iN i+1 x M i+1 2 )
  • the UV detection is represented in Figure 6.
  • the polymer obtained in example 3 was applied on the surface of a first si 1 i cone film with a brush thus forming a polymer layer. Then, a second silicone film was applied on said polymer layer.
  • the two films could be peeled * Then the assembly was placed in an oven during 2 hours at 80°C at 90% moisture.
  • both films were firmly attached to each other, they could not be peeled off, indicating that the cross- linking reaction has occurred.

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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)
  • Silicon Polymers (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne un polymère de silicone qui comprend un groupe isocyanate protégé représenté par la formule (I) dans lequel A représente un groupe alcanediyle en C1-C10; B représente un groupe protecteur qui peut être libéré à une température comprise entre 50 et 200° C, chaque X représente indépendamment hydrogène ou un groupe alkyle C1-C4, p représente un entier compris entre 2 et 850, n représente un entier supérieur à 1. L'invention concerne également le procédé de préparation desdits polysiloxanes et l'utilisation de ces derniers.
PCT/EP2012/069803 2011-10-06 2012-10-05 Polysiloxanes à restauration contrôlée, procédé de préparation et utilisation desdits polysiloxanes WO2013050579A1 (fr)

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IBPCT/IB2011/002829 2011-10-06
IB2011002829 2011-10-06

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103819498A (zh) * 2014-01-27 2014-05-28 合肥工业大学 一种封闭异氰酸酯偶联剂及其应用
CN106800639A (zh) * 2017-01-23 2017-06-06 天津大学 一种高强高韧离子自修复聚合物材料及制备方法
CN105802576B (zh) * 2016-05-07 2018-06-29 南京大学 一种自修复强力胶及其制备方法
CN111393648A (zh) * 2020-03-26 2020-07-10 中国海洋大学 一种环境友好型自修复可拉伸的聚硅氧烷基材料及其合成方法与应用
CN112063153A (zh) * 2020-08-27 2020-12-11 华南理工大学 兼具高机械性能和自修复功能的聚硅氧烷超分子弹性体及其制备方法与应用

Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB841825A (en) 1955-08-05 1960-07-20 Wacker Chemie Gmbh Process for the manufacture of elastomeric organo-polysiloxane products
GB1097379A (en) 1965-12-30 1968-01-03 Dow Corning Silicone rubbers
US3689454A (en) 1971-01-06 1972-09-05 Gen Electric Curable compositions
US3862919A (en) 1972-12-06 1975-01-28 Wacker Chemie Gmbh Organopolysiloxane compositions having resilient properties
BE842305A (fr) 1975-05-30 1976-11-29 Composes stanno-siliciques utilisables pour la preparation de polyorganosiloxanes
US4111890A (en) 1977-12-19 1978-09-05 Sws Silicones Corporation Curable organopolysiloxane compositions containing titanium esters
GB2144758A (en) 1983-08-08 1985-03-13 Gen Electric Method for making alkoxy terminated polydiorganosiloxane
FR2557582A1 (fr) 1983-12-28 1985-07-05 Rhone Poulenc Spec Chim Composition polyorganosiloxanique durcissant en elastomere et comportant un catalyseur a l'etain chelate
EP0235049A1 (fr) 1986-01-09 1987-09-02 Rhone-Poulenc Chimie Système catalytique à l'étain pour composition organopolysiloxane durcissable dès la température ambiante
US4722967A (en) 1980-07-02 1988-02-02 General Electric Company Titanium chelate catalyst for silicone compositions
US5698653A (en) 1996-05-10 1997-12-16 General Electric Company Non-corrosive translucent RTV compositions
US6818721B2 (en) 2002-12-02 2004-11-16 Rpo Pty Ltd. Process for producing polysiloxanes and use of the same
FR2856694A1 (fr) 2003-06-25 2004-12-31 Rhodia Chimie Sa Compositions polyorganosiloxanes (pos) monocomposantes reticulant par des reactions de polycondensation en elastomeres a temperature ambiante et en presence d'eau, et elastomeres ainsi obtenus
WO2011018161A1 (fr) 2009-08-11 2011-02-17 Bayer Materialscience Ag Composés pour la désactivation d’espèces catalytiques métalliques résiduelles dans des résines à base de polyol de polyester, procédé de désactivation et son application dans la production de polyuréthanne
US20110120344A1 (en) * 2008-07-29 2011-05-26 E.I. Dupont De Nemours And Company Surface active blocked isocyanates and coating compositions thereof

Patent Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB841825A (en) 1955-08-05 1960-07-20 Wacker Chemie Gmbh Process for the manufacture of elastomeric organo-polysiloxane products
GB1097379A (en) 1965-12-30 1968-01-03 Dow Corning Silicone rubbers
US3689454A (en) 1971-01-06 1972-09-05 Gen Electric Curable compositions
US3862919A (en) 1972-12-06 1975-01-28 Wacker Chemie Gmbh Organopolysiloxane compositions having resilient properties
BE842305A (fr) 1975-05-30 1976-11-29 Composes stanno-siliciques utilisables pour la preparation de polyorganosiloxanes
US4111890A (en) 1977-12-19 1978-09-05 Sws Silicones Corporation Curable organopolysiloxane compositions containing titanium esters
US4722967A (en) 1980-07-02 1988-02-02 General Electric Company Titanium chelate catalyst for silicone compositions
GB2144758A (en) 1983-08-08 1985-03-13 Gen Electric Method for making alkoxy terminated polydiorganosiloxane
FR2557582A1 (fr) 1983-12-28 1985-07-05 Rhone Poulenc Spec Chim Composition polyorganosiloxanique durcissant en elastomere et comportant un catalyseur a l'etain chelate
EP0235049A1 (fr) 1986-01-09 1987-09-02 Rhone-Poulenc Chimie Système catalytique à l'étain pour composition organopolysiloxane durcissable dès la température ambiante
US5698653A (en) 1996-05-10 1997-12-16 General Electric Company Non-corrosive translucent RTV compositions
US6818721B2 (en) 2002-12-02 2004-11-16 Rpo Pty Ltd. Process for producing polysiloxanes and use of the same
FR2856694A1 (fr) 2003-06-25 2004-12-31 Rhodia Chimie Sa Compositions polyorganosiloxanes (pos) monocomposantes reticulant par des reactions de polycondensation en elastomeres a temperature ambiante et en presence d'eau, et elastomeres ainsi obtenus
US20110120344A1 (en) * 2008-07-29 2011-05-26 E.I. Dupont De Nemours And Company Surface active blocked isocyanates and coating compositions thereof
WO2011018161A1 (fr) 2009-08-11 2011-02-17 Bayer Materialscience Ag Composés pour la désactivation d’espèces catalytiques métalliques résiduelles dans des résines à base de polyol de polyester, procédé de désactivation et son application dans la production de polyuréthanne

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103819498A (zh) * 2014-01-27 2014-05-28 合肥工业大学 一种封闭异氰酸酯偶联剂及其应用
CN103819498B (zh) * 2014-01-27 2017-01-11 合肥工业大学 一种封闭异氰酸酯偶联剂及其应用
CN105802576B (zh) * 2016-05-07 2018-06-29 南京大学 一种自修复强力胶及其制备方法
CN106800639A (zh) * 2017-01-23 2017-06-06 天津大学 一种高强高韧离子自修复聚合物材料及制备方法
CN106800639B (zh) * 2017-01-23 2019-06-14 天津大学 一种高强高韧离子自修复聚合物材料及制备方法
CN111393648A (zh) * 2020-03-26 2020-07-10 中国海洋大学 一种环境友好型自修复可拉伸的聚硅氧烷基材料及其合成方法与应用
CN111393648B (zh) * 2020-03-26 2021-06-08 中国海洋大学 一种环境友好型自修复可拉伸的聚硅氧烷基材料及其合成方法与应用
CN112063153A (zh) * 2020-08-27 2020-12-11 华南理工大学 兼具高机械性能和自修复功能的聚硅氧烷超分子弹性体及其制备方法与应用

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