US20130137817A1 - Cure-On-Demand Liquid Sealant Composition, Process For The Preparation Thereof And Uses Thereof - Google Patents

Cure-On-Demand Liquid Sealant Composition, Process For The Preparation Thereof And Uses Thereof Download PDF

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US20130137817A1
US20130137817A1 US13/690,084 US201213690084A US2013137817A1 US 20130137817 A1 US20130137817 A1 US 20130137817A1 US 201213690084 A US201213690084 A US 201213690084A US 2013137817 A1 US2013137817 A1 US 2013137817A1
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crosslinking agent
chosen
function
unsaturated
composition according
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Elise LABORBE
Benoit Le Rossignol
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Hutchinson SA
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Hutchinson SA
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Assigned to HUTCHINSON reassignment HUTCHINSON ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: AUVERGNE, REMI, BOUTEVIN, BERNARD, FROIDEVAUX, VINCENT, LABORBE, ELISE, LE ROSSIGNOL, BENOIT
Priority to US14/703,111 priority Critical patent/US9850412B2/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J181/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Adhesives based on polysulfones; Adhesives based on derivatives of such polymers
    • C09J181/04—Polysulfides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/48—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding
    • B29C65/52—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding characterised by the way of applying the adhesive
    • B29C65/54—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding characterised by the way of applying the adhesive between pre-assembled parts
    • 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
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
    • C09K3/1012—Sulfur-containing polymers, e.g. polysulfides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2079/00—Use of polymers having nitrogen, with or without oxygen or carbon only, in the main chain, not provided for in groups B29K2061/00 - B29K2077/00, as moulding material
    • B29K2079/08—PI, i.e. polyimides or derivatives thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
    • B29K2081/00—Use of polymers having sulfur, with or without nitrogen, oxygen or carbon only, in the main chain, as moulding material
    • B29K2081/04—Polysulfides, e.g. PPS, i.e. polyphenylene sulfide or derivatives thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
    • B29L2031/00—Other particular articles

Definitions

  • the subject of the invention is a new liquid sealant composition based on polysulphide, capable of curing on demand, and the process for preparing same.
  • the present invention also relates to a process for coating a substrate with a composition according to the invention.
  • the cured sealant materials formed from this composition also form part of the invention.
  • the invention also relates to the use of a liquid sealant composition according to the invention for the construction and/or the maintenance, and more particularly for the adhesive bonding and/or the protection, of vehicles and machines.
  • Polysulphide compositions in liquid and curable form have been used for a long time in the sealant field, owing to the durability and impermeability of these polymers (ALIPS—Aliphatic Polysulfides—Monograph of an elastomer—Heinz LUCKE, Hüthig & Wepf, 1994).
  • sealant materials are used in particular for the isolation, adhesive bonding or protection against corrosion of construction materials used in the construction, transport or aeronautical fields. They are generally two-component systems consisting of a base (or matrix) and a curing agent (or crosslinking agent). It is during a mixing step that these two components react together and crosslink so as to form the final mastic.
  • EP 0 619 355 describes a polysulphide system crosslinked with (meth)acrylates, using a guanidine derivative as catalyst.
  • the reaction brought about is very rapid (very short gel time), which leaves little time for using the mastic.
  • the gel times vary from less than one minute to 20 minutes without retarder, and can be increased at most up to 7 hours through the use of an acid retarder.
  • PS polysulphide
  • Patent EP 1 478 703 describes a process for coating a substrate by applying a sealant material capable of curing on demand.
  • the material used can be based on polysulphide with an —SH end group, together with a crosslinking agent such as an acrylate, an isocyanate or an epoxy resin, said not yet cured material containing a latent catalyst which is formed and/or released in active form under the action of external energy, such as heating or electromagnetic radiation, and by which the reaction between the polysulphide and the curing agent is initiated and/or accelerated. This reaction results in the curing of the sealant material.
  • the latent catalyst used is an amine encapsulated in a polymer shell.
  • the present invention aims to overcome these drawbacks by developing liquid sealant compositions in which the reaction between the matrix and the curing agent would be effectively blocked by making the reactive function of the curing agent inaccessible, independently of the presence or absence of a catalyst.
  • This concept allows the preparation of a “one-component” mastic system which is stable over time at ambient temperature, and consequently stable during storage. This system can be irreversibly and rapidly cured on demand by virtue of the provision of external (thermal, photochemical, etc.) energy.
  • the strategy of blocking the crosslinking according to the invention by chemical blocking of the reactive function of the crosslinking agent, results in a more effective blocking of the mastics of the invention compared with the mastics of patent EP 1 478 703.
  • liquid sealant compositions of the invention also allow the use of curing agents which are very reactive with respect to the polysulphide, without the risk of impairing the stability of the one-component system.
  • compositions of the invention result in crosslinked mastics exhibiting excellent mechanical and chemical properties:
  • compositions of the invention correspond much more satisfactorily to the SCOD concept as it is really defined, than the solutions hitherto described in the prior art (a scheme of the principle of an ideal SCOD system is represented in FIG. 1 ).
  • FIG. 1 illustrates a scheme of the principle of an ideal SCOD system.
  • the first subject of the invention is a liquid sealant composition
  • a liquid sealant composition comprising at least:
  • a crosslinking agent chosen from ethylenically unsaturated or acetylenically unsaturated compounds, said unsaturated ethylenic or unsaturated acetylenic functions being chemically blocked with a blocking agent, by Diels-Alder reaction,
  • the blocking agent serves to protect the unsaturated ethylenic or unsaturated acetylenic function of the crosslinking agent. It is subsequently removed under the effect of external energy which causes the release of the unsaturated ethylenic or unsaturated acetylenic function, and which results in the initiation of the reaction between the polysulphide and the crosslinking agent and therefore in the curing of the mass.
  • the polysulphide of the invention preferably has a —SH functionality ⁇ 2.
  • Said polysulphide can have an average molecular weight of between 1000 and 6500 g ⁇ mol ⁇ 1 , and preferably between 2000 and 3500 g ⁇ mol ⁇ 1 . Its viscosity can be between 1 and 150 Pa ⁇ s, and preferably between 10 and 50 Pa ⁇ s.
  • the Tg of the polysulphide can be between ⁇ 55 and ⁇ 65° C.
  • the crosslinking agent of the invention has a functionality f ⁇ 2, and preferably 2 ⁇ f ⁇ 4.
  • the crosslinking agent can be a compound or a mixture of several compounds bearing an allyl function, a maleimide function, or an ethylenically unsaturated or acetylenically unsaturated function bearing an electron-withdrawing group in the alpha position with respect to this double bond or this triple bond, it being possible for said function to be an aldehyde function, ketone function, ester function, hemiester function, amide function, hemiamide function, ester-amide function, nitrile function or imide function which is ⁇ , ⁇ -ethylenically unsaturated.
  • the crosslinking agents which are most preferred are maleimides, hemiesters and ester-amides.
  • the stoichiometric ratio between the ethylenic function of the curing agent and the —SH group of the polysulphide can range from 1 to 1.4.
  • the crosslinking agent is an ⁇ , ⁇ -ethylenically unsaturated imide compound or a mixture of several ⁇ , ⁇ -ethylenically unsaturated imide compounds chosen from monomaleimide, bismaleimide or trismaleimide compounds of formula:
  • a polysulphide is a polymer comprising at least one S—S bond in its chain.
  • the W unit may be a C 1 -C 30 alkyl chain comprising one or more heteroatoms chosen from O, S or N.
  • W is a polyether unit
  • it is preferably a polyethylene glycol (PEG) unit, a polypropylene glycol (PPG) unit, or a mixed PEG/PPG unit.
  • the crosslinking agent is then preferably chosen from the compounds of formula:
  • W is a polythioether or polysulphide unit
  • said unit may be a C 1 -C 30 alkyl chain comprising one or more O heteroatoms or one or more S heteroatoms. It is preferably a unit of formula:
  • n ′ CH 2 —CH 2 —CH 2 —CH 2 —CH 2 —S—[CH 2 —CH 2 —O—CH 2 —O—CH 2 —CH 2 —S—S] n′ —CH 2 —CH 2 —O—CH 2 —O—CH 2 —CH 2 —S—CH 2 —CH 2 —,in which n ′ ranges from 0 to 7.
  • the blocking agent may be a diene comprising at least one pentacyclic nucleus, and preferably a diene corresponding to the following formula:
  • the blocking agents which are the most preferred are chosen from:
  • the catalyst used is preferably chosen from:
  • the catalysts which are the most preferred are tertiary amines, and more particularly 1,4-diazabicyclo[2,2,2]octane (DABCO or TEDA) and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU).
  • DABCO 1,4-diazabicyclo[2,2,2]octane
  • DBU 1,8-diazabicyclo[5,4,0]undec-7-ene
  • the amount of catalyst used ranges from 0 to 10 parts by weight per 100 parts of polysulphide polymer, and preferably from 0.5 to 5 parts.
  • Another subject of the invention relates to a process for preparing a liquid sealant composition according to the invention, namely a “ready-to-use” one-component mastic, comprising at least the following steps:
  • the mixing step ii) can be carried out mechanically using a mixer, for instance a Dispermat® blade (butterfly or notched) mixer, or a planetary mixer (mixer comprising a blade and one or more dispersers).
  • a mixer for instance a Dispermat® blade (butterfly or notched) mixer, or a planetary mixer (mixer comprising a blade and one or more dispersers).
  • the “ready-to-use” liquid sealant composition or mastic thus prepared is subsequently packaged in a pot or in a cartridge.
  • the invention also relates to a coating process for attaching or adhesively bonding sealing trims and/or pieces or filling hollow spaces or intermediate gaps, said process comprising a step of applying a liquid sealant composition according to the invention to a substrate (made of aluminium, steel, glass, composites, etc.), followed by a step of deprotecting the crosslinking agent chemically blocked with a blocking agent, under the effect of external energy, which results in the initiation of the reaction between the polysulphide and the crosslinking agent, and therefore in the curing of the mass of the sealant material.
  • the external energy required for deblocking the crosslinking agent can be thermal energy provided:
  • the crosslinking agent chemically blocked with a blocking agent is deprotected by heating at a temperature in the range of from 60 to 120° C., and preferably from 70 to 100° C.
  • the crosslinking agent chemically blocked with a blocking agent is subjected to the action of heat for a period ranging from 15 minutes to 2 hours.
  • the coating process of the invention may also comprise, after the step of deprotecting the crosslinking agent, a step of curing the mass of the sealant material.
  • This curing step is preferably carried out at a temperature ranging from 18 to 35° C., for a period ranging from 1 to 3 days.
  • Another subject of the invention relates to a cured sealant material which results from the curing of a liquid sealant composition according to the invention, and which exhibits, after complete curing, a tensile strength according to standard ISO 37 of at least 1 MPa, a tensile elongation at break according to standard ISO 37 of at least 100%, and a hardness according to standard ISO 7619 of at least 40 shA.
  • a last subject of the present invention relates to the use of a liquid sealant composition according to the invention for constructing and/or maintaining aircraft or spacecraft, motor vehicles, rail vehicles, ships, machines, appliances and furniture, and more particularly for adhesive bonding and/or protection against corrosion of aircraft or spacecraft, motor vehicles, rail vehicles, ships, machines, appliances and furniture.
  • the invention also comprises other arrangements which will emerge from the following further description, which refers to examples demonstrating the advantageous properties of the compositions of the invention, and also to the appended FIG. 1 which represents a scheme of the principle of an ideal SCOD system.
  • This example studies the preparation of a crosslinking agent, the maleimide function of which is blocked by Diels-Alder (DA) reaction, and also the deblocking conditions, and more specifically the temperature of the retro-Diels-Alder (r-DA) reaction.
  • DA Diels-Alder
  • r-DA retro-Diels-Alder
  • the study of the chemical blocking and deblocking of the maleimide function is carried out on a bifunctional model compound, with several blocking agents, namely furan derivatives of different natures.
  • the determination of the DA and r-DA reaction temperatures is measured by means of NMR monitoring of the blocked maleimide, by gradual increase in the temperature.
  • the furan derivatives make it possible to block the maleimide function at “low temperature”, the DA temperatures being 40° C. (it being possible for these temperatures to be brought back to ambient temperature by increasing the reaction time from 4 hours to 4 days).
  • the r-DA temperatures are between 65 and 95° C., thus making it possible to envisage deblocking at “moderate temperature”, and which is consequently compatible with the intended final application and the thermal activation envisaged.
  • This example studies the preparation of a polysulphide mastic by crosslinking of a liquid polysulphide (PS) polymer with a bismaleimide.
  • PS liquid polysulphide
  • Two liquid bismaleimides having a PPG-type backbone are tested in parallel: one synthesized from PPG 230 (Jeffamine D230, Huntsman) and the other from PPG 400 (Jeffamine D400, Huntsman).
  • the reactivity of these systems is studied comparatively on the bismaleimides in the blocked and nonblocked state.
  • the deblocking of the bismaleimide crosslinking agent, and therefore the activation of the crosslinking is carried out by heating in an oven.
  • the blocked bismaleimide crosslinking agents are prepared beforehand.
  • liquid bismaleimides are synthesized, then purified and characterized by NMR.
  • these bismaleimides are blocked by Diels-Alder reaction, via a furan-derived blocking agent, furfuryl acetate. NMR verification makes it possible to check that the double bonds of the bismaleimides are actually blocked.
  • the apparatus is then placed under nitrogen for a period of 10 minutes, and then ZnBr 2 (2.3 eq) is added under a nitrogen stream.
  • ZnBr 2 2.3 eq
  • the mixture is heated to 40° C., and then a solution of bis(trimethylsilyl)amine (HMDS) solubilized in THF (1 ml/ml of HMDS) is added dropwise using a dropping funnel.
  • HMDS bis(trimethylsilyl)amine
  • the viscous liquid is then extracted via a liquid/liquid extraction with water and chloroform (1/3 ratio). The operation is carried out three times, in order to remove any trace of water due to the cyclization (2 nd step). After having dried the organic phase with anhydrous Na 2 SO 4 , the solvent is evaporated off. Finally, the product obtained is solubilized in toluene (3 ml/g of product), and then heated at 100° C. overnight, in order to obtain exclusively the maleimide.
  • the bismaleimide to be blocked is placed in a single-necked round-bottomed flask.
  • Solvent THF or DCM, 1 ml/g of product
  • the blocking agent is added in stoichiometric amount, and then the mixture is left to react for 3 to 4 days at ambient temperature, or 4 hours at 40° C. Two diastereoisomers are obtained (endo and exo), demonstrated by NMR verification.
  • liquid sealant compositions are subsequently prepared from:
  • the amounts of polysulphide and of crosslinking agent to be mixed observe the stoichiometry of 1.1 between the ethylenic functions of the bismaleimide and the thiol functions of the polysulphide.
  • the catalyst if it is used, is added in an amount of 3 parts (per hundred parts of polysulphide). All the constituents are mixed manually or mechanically using a Dispermat® blade mixer/disperser.
  • the gel time which characterizes the time for the mastic to start to set (start of formation of the three-dimensional crosslinking network), and therefore the end of the safety period for using the mastic, is determined by a simple bench test.
  • the test is carried out in an aluminium dish, on the basis of 20 g of polysulphide. The measurement begins as soon as the polysulphide and the crosslinking agent are brought into contact (start of the mixing step).
  • the increase in viscosity of the system is evaluated qualitatively by stirring the mixture with a spatula, until the “gel time” or “string time” is reached, i.e. the moment at which the system begins to become elastic and begins to form a “string” when trying to withdraw the spatula.
  • the viscous liquid then undergoes a liquid/liquid extraction with water and chloroform (1/3 respectively); the operation is repeated three times in order to remove any trace of water due to the cyclization (2 nd step).
  • the solvent is evaporated off.
  • the product obtained is then solubilized in toluene (3 ml/g of product), and then heated at 100° C. for two days, in order to obtain exclusively the maleimide.
  • a mastic was then prepared from:
  • the mastic was subsequently characterized in a standard manner, after 14 days at ambient temperature, once the temperature deblocking had been carried out by placing in an oven at a temperature of 100° C. for a period of 1h30:
  • compositions evaluated in the counterexample are representative of the prior art described in patent EP 1 478 703. They are PS/epoxy resin or PS/acrylate reactive systems, with a “latent” catalyst, namely an encapsulated tertiary amine.
  • the PS/acrylate system is a Thioplast® G21 (Akzo Nobel)/SR 454 (Sartomer): triacrylate (TMPEOTA, ethoxylated trimethylolpropane triacrylate) system.
  • the encapsulated amine catalyst was prepared in the form of microparticles based:
  • the amine in liquid form is adsorbed onto the silica.
  • the silica particles containing the amine are then coated with wax in a fluidized airbed (vaporization of the wax in the molten state).
  • the systems are prepared by manually mixing the polysulphide, the crosslinking agent (epoxy resin or acrylate) and the amine catalyst (liquid in its free form or else encapsulated in its latent form).
  • the manual mixing allows “gentle” mixing of the constituents, and thus avoids any damage to the catalyst microparticles which could generate early activation of the reactive system.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Sealing Material Composition (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US13/690,084 2011-11-30 2012-11-30 Cure-On-Demand Liquid Sealant Composition, Process For The Preparation Thereof And Uses Thereof Abandoned US20130137817A1 (en)

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FR1160969A FR2983204B1 (fr) 2011-11-30 2011-11-30 Composition liquide d'etancheite reticulable a la demande, son procede de preparation et ses applications
FR1160969 2011-11-30

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EP (1) EP2599817B1 (fr)
CN (1) CN103131185B (fr)
BR (1) BR102012030396A8 (fr)
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JP2016512278A (ja) * 2013-03-13 2016-04-25 スリーエム イノベイティブ プロパティズ カンパニー アルキン系結合を有する放射線硬化性ポリチオエーテル
WO2016090221A1 (fr) * 2014-12-04 2016-06-09 Prc-Desoto International, Inc. Matériaux d'étanchéité à base de polythioéther à temps de travail prolongé
WO2016128548A1 (fr) 2015-02-13 2016-08-18 Chemetall Gmbh Matière d'étanchéité à base de composé époxy/polymère de base à terminaison mercapto et procédé de durcissement au moyen d'un catalyseur photolatent
US12023709B2 (en) 2015-02-13 2024-07-02 Chemetall Gmbh Method of applying a sulphur-containing sealing compound, apparatus therefor, correspondingly treated aerospace vehicle and use thereof

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016512278A (ja) * 2013-03-13 2016-04-25 スリーエム イノベイティブ プロパティズ カンパニー アルキン系結合を有する放射線硬化性ポリチオエーテル
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FR2983204B1 (fr) 2014-01-10
CA2796259C (fr) 2020-03-31
BR102012030396A8 (pt) 2017-11-28
US20150232725A1 (en) 2015-08-20
CN103131185A (zh) 2013-06-05
CN103131185B (zh) 2018-09-28
BR102012030396A2 (pt) 2015-01-13
EP2599817A1 (fr) 2013-06-05
FR2983204A1 (fr) 2013-05-31
ES2570702T3 (es) 2016-05-19
EP2599817B1 (fr) 2016-02-03
US9850412B2 (en) 2017-12-26

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