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WO2018160678A1 - Composition de matériau d'étanchéité durcissable - Google Patents

Composition de matériau d'étanchéité durcissable Download PDF

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Publication number
WO2018160678A1
WO2018160678A1 PCT/US2018/020196 US2018020196W WO2018160678A1 WO 2018160678 A1 WO2018160678 A1 WO 2018160678A1 US 2018020196 W US2018020196 W US 2018020196W WO 2018160678 A1 WO2018160678 A1 WO 2018160678A1
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Prior art keywords
polysulfide
group
carbon atoms
catalyst
independently
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PCT/US2018/020196
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English (en)
Inventor
Anping Wang
Karl Matos
Ralph Dieter Maier
Elizabeth R. Burkhardt
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Basf Se
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Publication of WO2018160678A1 publication Critical patent/WO2018160678A1/fr

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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
    • 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
    • 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
    • C09K2003/1034—Materials or components characterised by specific properties
    • C09K2003/1068—Crosslinkable materials

Definitions

  • This disclosure generally relates to a curable sealant composition. More specifically, this disclosure relates a sealant composition that includes a polysulfide having an -SH group, an isocyanate component, and a particular catalyst.
  • Polysulfide compositions in liquid and curable form are known in the art and have been used in a variety of industries.
  • polysulfides are cured by an oxidoreduction reaction wherein manganese dioxide is used to cure the polysulfides over a number of days.
  • manganese dioxide is used to cure the polysulfides over a number of days.
  • the long curing time increases production times and costs and reduces efficiency.
  • sealants in the manufacture or maintenance of aircraft has previously been a very complex process.
  • the reason for this is the numerous joints having sealants, where sealants that often have very long processing times of up to 60 hours must be used.
  • These methods typically require an extremely long time for complete curing and have required a very long tack-free time in the past in proportion to the length of the processing time.
  • an interlayer sealant of class C for the aviation field typically takes 60 to 70 days to achieve a Shore A hardness of 30 if the processing time is 60 hours.
  • This disclosure provides a curable sealant composition that includes a polysulfide having an -SH group, an isoc t having the structure:
  • each of R 1 and R 3 is independently an organic radical having 1 to 20 carbon atoms
  • each of R 2 , R 4 , and R 5 is independently H or an organic radical having 1 to 20 carbon atoms
  • a " is an anion.
  • This disclosure also provides a cured sealant formed from the curable sealant composition, a cured sealant including the polymerization product of the polysulfide and the isocyanate component reacted in the presence of the catalyst, a curable sealant system including a first component including the polysulfide and the catalyst and a second component including the isocyanate component.
  • This disclosure also provides an article including a substrate and the cured sealant or curable sealant disposed on the substrate.
  • This disclosure also provides a method of forming the curable sealant composition wherein the method includes the steps of providing the polysulfide, the isocyanate component, and the catalyst and combining the polysulfide, the isocyanate component, and the catalyst to form the curable composition.
  • This disclosure further provides a method of forming the cured sealant wherein the method includes the steps of providing the polysulfide, the isocyanate component, and the catalyst and combining the polysulfide, the isocyanate component, and the catalyst such that the polysulfide polymerizes with the isocyanate component in the presence of the catalyst to form the cured sealant.
  • this disclosure provides a method of forming the article wherein the method includes the steps of providing the polysulfide, the isocyanate component, and the catalyst and applying the polysulfide, the isocyanate component, and the catalyst onto the substrate such that the polysulfide polymerizes with the isocyanate component in the presence of the catalyst and forms the cured sealant disposed on the substrate.
  • Figure 1 is a chart setting forth various options for physical properties of non-limiting Thiokol polysulfides that maybe utilized in this disclosure.
  • Figure 2A is a formula of a non-limiting Thioplast polysulfide that may be utilized in this disclosure.
  • Figure 2B is a formula of a second non-limiting Thioplast polysulfide that may be utilized in this disclosure.
  • FIG. 2C is a chart setting forth various options for physical properties of non- limiting Thioplast polysulfides that may be utilized in this disclosure including reference back to Figures 2A and 2B.
  • composition a curable sealant composition (hereinafter described as the "composition.”).
  • the composition is curable and maybe cured. After cure, the composition may be described as a curable sealant composition or simply as the cured composition.
  • This disclosure describes an uncured composition, a partially cured composition, and a completely or fully cured composition. Accordingly, below, the terminology “composition” may describe any of the aforementioned types of compositions unless otherwise particularly stated.
  • the composition is not particularly limited and may be used in any industry, for example, in aeronautics, construction, for constructing and/or maintaining aircraft or spacecraft, in motor vehicles, in rail vehicles, in ships, in machines, in 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 composition is used as a sealant in an aircraft.
  • the composition is used as a sealant on a fuel-tank of an aircraft.
  • the composition is used as a sealant on a fuel-tank of a vehicle such as a train, automobile, etc.
  • the composition includes, is, consists essentially of, or consists of, a polysulfide having an -SH group, an isocyanate component, and a particular catalyst.
  • a polysulfide having an -SH group an isocyanate component
  • a particular catalyst a particular catalyst.
  • the terminology "consists essentially of” describes non-limiting embodiments that are free of one or more polymers that are not, for example, polysulfides and/or polymeric isocyanates, free of one or more monomers that are not, for example, monomeric isocyanates, free of one or more catalysts that are not those of this disclosure, and/or free of one or more additives known in the art and/or described below.
  • the selection of which components to exclude from a composition "consisting essentially of the polysulfide, the isocyanate, and the catalyst can be made by one of skill in the art.
  • the composition includes a polysulfide but may include two or more polysulfides or combinations of polysulfides, any one or more of which may be described below.
  • the composition may include at least one polysulfide, at least two polysulfides, etc.
  • the terminology "polysulfide” may include two or more polysulfides.
  • polysulfide typically describes (one or more) polysulfide (homo) polymer(s). However, it is contemplated that (one or more) polysulfide (co)polymer(s) may also be used, either alone or in combination with the (one or more) (homo) polymers.
  • the polysulfide may alternatively be described as a polythioether.
  • various species of the genus polysulfides are polythioethers. Accordingly, the polysulfide may be further defined as polythioether or two or more polythioethers.
  • the composition may include a polysulfide and a polythioether.
  • the polysulfide has an -SH group but otherwise is not particularly limited and maybe any in the art.
  • the polysulfide may have a single -SH group or two or more -SH groups. One or more or all of the groups may be terminal or pendant.
  • the polysulfide is described as part of a class of chemical compounds including chains of sulfur atoms.
  • the polysulfide is a polymer having at least one S-S bond in its chain and an -SH group.
  • the polysulfide of this disclosure is typically described as an organic polysulfide (as opposed to a sulfide anion (S a 2 ).
  • the polysulfide of this disclosure has the formula RS a R(-SH) b , wherein (a) is a number of 2 or greater, each R is independently an alkyl or aryl group, each -SH group is terminal or pendant, and (b) is a number of 1 or greater.
  • the polysulfide is further defined as including a plurality of blocks each having the formula -R ⁇ S x - wherein x is from 1 to 5 and R 1 is an alkyl group having 2 to 16 carbon atoms or an alkyl group 16 carbon atoms that further comprises one or more ether groups, and further having a terminal thiol group having the formula -R 2 -SH, wherein R is an alkyl group having 2 to 16 carbon atoms or an alkyl group having 2 to 16 carbon atoms that further comprises an ether-bond.
  • the polysulfide is a polythioether that has the formula -R 3 - [-S-(CH 2 )2-0-[-R 4 -0-] m -(CH 2 )2-S-R 3 -] perennial-.
  • each of R 3 and R 4 is independently a C 2 -C6 n-alkylene group, a C3-C6 branched alkylene group, a C6-C 8 cycloalkylene group, a C 6 -Cio alkylcycloalkylene group, or -[(-CH 2 -) p -X-] q -(-CH 2 -) r -, or -[(-CH 2 -) p -X-] q -(-CH 2 -) r in which at least one CH 2 unit is substitute with a methyl group.
  • m is a number from 0 to 10, e.g.
  • n is a number from 1 to 60, e.g. 5 to 55, 10 to 50, 15 to 45, 20 to 40, 25 to 35;
  • p is a number from 2 to 6, e.g. 2, 3, 4, 5, or 6;
  • q is a number from 1 to 5, e.g. 1, 2, 3, 4, or 5, and
  • r is a number from 2 to 10, e.g. 2, 3, 4, 5, 6, 7, 8, 9, or 10.
  • all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the polysulfide is a polythioether that has the formula:
  • x is from 1 to 200, e.g. 5 to 195, 10 to 190, 15 to 185, 20 to 180, 25 to 175, 30 to 170, 35 to 165, 40 to 160, 45 to 155, 50 to 150, 55 to 145, 60 to 140, 65 to 135, 70 to 130, 75 to 125, 80 to 120, 85 to 1 15, 90 to 110, 95 to 105, or 95 to 100.
  • all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the polysulfide is a polythioether that has the formula:
  • z is from 7 to 43, e.g. 10 to 40, 15 to 35, 20 to 30, or 20 to 25.
  • the polysulfide has the formula: HS-(R-SS) t -R-SH, wherein each R is independently a C 2 -C6 n-alkylene group, a C3-C6 branched alkylene group, a C6-C 8 cycloalkylene group, or a C6-C 10 alkylcycloalkylene group and wherein t is from 5 to 40, e.g. 10 to 35, 15 to 30, 20 to 30, or 25 to 30.
  • all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the polysulfide has the formula: HS-(R-SS) q -CH 2 CH((SS- R) v -SH)-CH 2 -(SS-R) r -SH, wherein each R is independently a C 2 -C6 n-alkylene group, a C3- Ce branched alkylene group, a C6-C 8 cycloalkylene group, or a C6-C10 alkylcycloalkylene group, wherein q+v+r is from 5 to 40, e.g. 10 to 35, 15 to 30, 20 to 30, or 25 to 30. In various non-limiting embodiments, all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the polysulfide is a polythioether that has the formula:
  • the polysulfide may be described as a long-chain polymer with a weight average molecular weight of 2800 to 9000 g/mol, e.g. those of Thioplast G131 or with a weight average molecular weight of 3300 to 5000 g/mol such as Thioplast G10, Thioplast G12, Thioplast Gl , Thiokol LP 32, and/or Thiokol LP 12.
  • a weight average molecular weight of 2800 to 9000 g/mol e.g. those of Thioplast G131 or with a weight average molecular weight of 3300 to 5000 g/mol
  • all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the polysulfide may be described as a short-chain polymer with a weight average molecular weight of 100 to 3200 g/mol, e.g. from 400 to 2800 g/mol and/or from 500 to 1200 g/mol, such as, for example, Thiokol LP3, Thioplast G4, Thioplast G22 or Thioplast G44.
  • both long-chain polymers with a weight average molecular weight of 2800 to 9000 g/mol or 3300 to 5000 g/mol and short-chain polymers with a weight average molecular weight of 400 to 2800 g mol or from 500 to 1200 g mol are used, e.g. in a weight ratio of 25:1 to 0.5:1, from 10:1 to 1:1 or from 6:1 to 2:1.
  • all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the polysulfide is described as a liquid polymer having a weight average molecular weight of from 100 to 7500 g/mol or from 500 to 6000 g/mol or from 1000 to 3000 g/mol.
  • the polysulfide may have a weight average molecular weight of from 1,000 to 7,500, from 1,500 to 6,000, from 2,000 to 5,500, from 2,500 to 5,000, from 3,000 to 4,500, or from 3,500 to 4,000, g/mol.
  • all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the polysulfide has a total sulfur content of from 1 to 50 wt %, 2 to 45 wt % or 10 to 38 wt %.
  • the polysulfide has an average functionality of -SH groups of greater than 2, greater than or equal to 2, 2, less than 2, or less than or equal to 2, e.g. from 1.5 to 2.5 or 1.9 to 2.2.
  • the average functionality is from 1.5 to 2 or 0.8 to 1.5.
  • the polysulfide has an average glass transition temperature Tg of from -80 to -30°C or -60 to -40°C, measured according to AITM 1-0003 Airbus Industry Test Method of June 1995. In various non- limiting embodiments, all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the polysulfide is chosen from one or more of the polysulfides described in one or more of Figures 1 and 2A-2C. Any and all values and ranges of values including and between any one or more of the values set forth in these Figures are hereby expressly contemplated herein in one or more non-limiting embodiments.
  • the amount of the polysulfide in the composition is not particularly limited.
  • the polysulfide is present in the composition in an amount of from 1 to 80, from 1 to 30, from 5 to 30, from 5 to 80, from 60 to 80, or from 30 to 80, parts by weight per 100 parts by weight of the composition.
  • the polysulfide is present in an amount of from 50 to 80, 60 to 80, 55 to 75, 60 to 70, or 65 to 70, parts by weight per 100 parts by weight of "Part A", as described below.
  • Part A parts by weight per 100 parts by weight of "Part A"
  • the isocyanate is not particularly limited and may be any known in the art.
  • the isocyanate maybe alternatively described as an isocyanate component that itself includes two or more individual isocyanates.
  • the isocyanate may be, include, consist essentially of, or consist of, any isocyanate known in the art, e.g. aliphatic isocyanates, aromatic isocyanates, polymeric isocyanates, or combinations thereof.
  • the isocyanate may be, include, consist essentially of, or consist of, more than one different isocyanate, e.g., polymeric diphenylmethane diisocyanate and 4,4'- diphenylmethane diisocyanate.
  • the isocyanate is chosen from diphenylmethane diisocyanates (MDIs), polymeric diphenylmethane diisocyanates (pMDIs), toluene diisocyanates (TDIs), hexamethylene diisocyanates (HDIs), isophorone diisocyanates (IPDIs), and combinations thereof.
  • MDIs diphenylmethane diisocyanates
  • pMDIs polymeric diphenylmethane diisocyanates
  • TDIs toluene diisocyanates
  • HDIs hexamethylene diisocyanates
  • IPDIs isophorone diisocyanates
  • the isocyanate typically includes, but is not limited to, isocyanates, diisocyanates, polyisocyanates, and combinations thereof.
  • the isocyanate includes an n-functional isocyanate.
  • n is a number typically from 2 to 5, more typically from 2 to 4, still more typically of from 2 to 3, and most typically about 2. It is to be understood that n may be an integer or may have intermediate values from 2 to 5.
  • the isocyanate typically includes an isocyanate selected from the group of aromatic isocyanates, aliphatic isocyanates, and combinations thereof.
  • the isocyanate includes an aliphatic isocyanate such as hexamethylene diisocyanate (HDI), dicyclohexyl-methylene-diisocyanate (H12MDI), isophorone- diisocyanate, and combinations thereof. If the isocyanate includes an aliphatic isocyanate, the isocyanate may also include a modified multivalent aliphatic isocyanate, i.e., a product which is obtained through chemical reactions of aliphatic diisocyanates and/or aliphatic polyisocyanates.
  • HDI hexamethylene diisocyanate
  • H12MDI dicyclohexyl-methylene-diisocyanate
  • isophorone- diisocyanate and combinations thereof.
  • the isocyanate may also include a modified multivalent aliphatic isocyanate, i.e., a product which is obtained through chemical reactions of aliphatic diisocyanates and/or alipha
  • the isocyanate may also include, but is not limited to, modified diisocyanates employed individually or in reaction products with polyoxyalkyleneglycols, diethylene glycols, dipropylene glycols, polyoxyethylene glycols, polyoxypropylene glycols, polyoxypropylenepolyoxethylene glycols, polyesterols, polycaprolactones, and combinations thereof.
  • the isocyanate can include an aromatic isocyanate. If the isocyanate includes an aromatic isocyanate, the aromatic isocyanate typically corresponds to the formula R'(NCO)z wherein R' is aromatic and z is an integer that corresponds to the valence of R'. Typically, z is at least two.
  • aromatic isocyanates include, but are not limited to, tetramethylxylylene diisocyanate (TMXDI), 1 ,4-diisocyanatobenzene, 1,3- diisocyanato-o-xylene, 1,3-diisocyanato-p-xylene, 1,3-diisocyanato-m-xylene, 2,4- diisocyanato-l-chlorobenzene, 2,4-diisocyanato-l-nitro-benzene, 2,5-diisocyanato-l- nitrobenzene, m-phenylene diisocyanate, p-phenylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, mixtures of 2,4- and 2,6-toluene diisocyanate, 1,5 -naphthalene diisocyanate, l-methoxy-2,
  • the aromatic isocyanate may include a triisocyanate product of m-TMXDI and 1,1,1-trimethylolpropane, a reaction product of toluene diisocyanate and 1,1,1-trimethyolpropane, and combinations thereof.
  • the isocyanate includes a diisocyanate selected from the group of methylene diphenyl diisocyanates, toluene diisocyanates, hexamethylene diisocyanates, H12MDIs, and combinations thereof.
  • the isocyanate may be an isocyanate pre-polymer.
  • the isocyanate pre-polymer may be a reaction product of an isocyanate and a polysulfide, polythioether, polyol and/or a polyamine.
  • the isocyanate may be a prepolymer that is the reaction product of an isocyanate and the polysulfide.
  • the isocyanate used in the pre-polymer can be any isocyanate as described above.
  • the polyol used to form the pre-polymer may be any polyol having a number average molecular weight of 400 g/mol or greater. For example, polyetherols, polyesterols, and combinations thereof can be used. Castor oil can also be used.
  • the isocyanate typically has an NCO content of from 3 to 50, alternatively from 3 to 33, alternatively from 18 to 30, weight percent when tested in accordance with DIN EN ISO 11909, and a viscosity at 25°C of from 5 to 2000, alternatively from 100 to 1000, alternatively from 150 to 250, alternatively from 180 to 220, mPa » sec when tested in accordance with DIN EN ISO 3219. In alternative embodiments, all values and ranges of values between and including the aforementioned values are hereby expressly contemplated. [0037] In various embodiments the isocyanate is, includes, consists essentially of, or consists of, monomelic and polymeric isocyanate.
  • the isocyanate includes polymeric diphenylmethane diisocyanate and 4,4 '-diphenylmethane diisocyanate, and has an NCO content of about 33.5 weight percent.
  • the isocyanate includes polymeric diphenylmethane diisocyanate and 4,4'-diphenylmethane diisocyanate, and has an NCO content of about 31.3 weight percent.
  • the isocyanate can be utilized in the composition in any amount.
  • the isocyanate is utilized in an amount of from 10 to 100, 20 to 90, 30 to 80, 40 to 70, or 50 to 60, weight percent based on a total weight of the composition.
  • the isocyanate is present in an amount of from 80 to 100, from 85 to 95, or from 90 to 65, parts by weight per 100 parts by weight of "Part B", as described below.
  • the isocyanate content is from 10 to 100% depending on additive choice and prepolymer composition. In various non-limiting embodiments, all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the composition also includes the catalyst.
  • the catalyst has the structure:
  • each of R 1 and R 3 is independently an organic radical having 1 to 20 carbon atoms
  • each of R 2 , R 4 , and R 5 is independently H or an organic radical having 1 to 20 carbon atoms
  • a " is an anion.
  • This catalyst may be alternatively described as an imidazolium ion.
  • each of R 1 , R 2 , R 3 , R 4 , and R 5 may independently be an organic radical having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, or 20 carbon atoms.
  • Any organic radical may be utilized, e.g. linear, branched, cyclic, and acyclic organic radicals.
  • the organic radical may be aliphatic or aromatic, or may include both aromatic and aliphatic groups.
  • the organic radical may include only carbon and hydrogen or may include carbon, hydrogen, and one or more heteroatoms such as oxygen atoms, nitrogen atoms, sulfur atoms, and/or phosphorus atoms.
  • the organic radical may include one or more functional groups such as hydroxyl groups, ether groups, ester groups, or carbonyl groups. It is contemplated that the organic radical may be free of one or more of any non- carbon and non-hydrogen heteroatoms including, but not limited to, those described above. Moreover, it is contemplated that the organic radical may be free of one or more functional groups including, but not limited to, those described above. In various non-limiting embodiments, all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • each of R 1 and R 3 is independently a hydrocarbon radical which, apart from carbon and hydrogen, may further include hydroxyl groups, ether groups, ester groups or carbonyl groups.
  • each of R 1 and R 3 includes no non-carbon or non-hydrogen heteroatoms, e.g., oxygen or nitrogen.
  • each of R 1 and R 3 is independently an aliphatic hydrocarbon radical.
  • Non-limiting examples of suitable hydrocarbon radicals include a phenyl group, benzyl group, a benzyl or phenyl group substituted by one or more Ci to C 4 alkyl groups, or a mesityl group, alkyl groups, and/or alkenyl groups, or combinations thereof.
  • each of R 1 and R 3 is independently a Q to Ci 8 alkyl group, a Ci to Ci6 alkyl group, a Q to C14 alkyl group, a Ci to C12 alkyl group, a Ci to C10 alkyl group, a Ci to Ce alkyl group, or a Q to C 4 alkyl group.
  • each of R and R is independently a methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl group.
  • each of R 1 and R 3 is independently a methyl, ethyl n-propyl, or n-butyl group.
  • R 1 is a Q to C alkyl group or a Q to C 4 alkyl group.
  • R 3 may be, for example, a methyl group.
  • R may be an H atom.
  • R may be an alkyl group such as a Ci to Ci 8 alkyl group, a Q to Ci6 alkyl group, a Q to Q 4 alkyl group, a Q to C12 alkyl group, a Ci to C10 alkyl group, a Ci to Ce alkyl group, or a Ci to C 4 alkyl group.
  • each of R 4 and R 5 may independently be a hydrogen atom or an organic radical having 1 to 10 carbon atoms.
  • each of R 4 and R 5 may independently be an organic radical having 1 , 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms and may be any of those described above.
  • Any organic radical may be utilized, e.g. linear, branched, cyclic, and acyclic organic radicals.
  • the organic radical may be aliphatic or aromatic, or may include both aromatic and aliphatic groups.
  • the organic radical may include only carbon and hydrogen or may include carbon, hydrogen, and one or more heteroatoms such as oxygen atoms, nitrogen atoms, sulfur atoms, and/or phosphorus atoms.
  • the organic radical may include one or more functional groups such as hydroxyl groups, ether groups, ester groups, or carbonyl groups. It is contemplated that the organic radical may be free of one or more of any non-carbon and non-hydrogen heteroatoms including, but not limited to, those described above. Moreover, it is contemplated that the organic radical may be free of one or more functional groups including, but not limited to, those described above. In various non-limiting embodiments, all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • each of R 4 and R 5 is independently a hydrocarbon radical which, apart from carbon and hydrogen, may further include hydroxyl groups, ether groups, ester groups or carbonyl groups.
  • each of R 4 and R 5 includes no non-carbon or non-hydrogen heteroatoms, e.g., oxygen or nitrogen.
  • each of R 4 and R 5 is independently an aliphatic hydrocarbon radical.
  • Non-limiting examples of suitable hydrocarbon radicals include a phenyl group, benzyl group, a benzyl or phenyl group substituted by one or more Ci to C 4 alkyl groups, or a mesityl group, alkyl groups, and/or alkenyl groups, or combinations thereof.
  • each of R 4 and R 5 is independently a Q to Ci 8 alkyl group, a Ci to Ci6 alkyl group, a Q to C14 alkyl group, a Ci to C12 alkyl group, a Ci to C10 alkyl group, a Ci to C6 alkyl group, or a Q to C 4 alkyl group.
  • each of R 4 and R 5 is independently a methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl group.
  • each of R 4 and R 5 is independently a methyl, ethyl n-propyl, or n-butyl group.
  • R 4 and R 5 are each H atoms.
  • R 2 , R 4 , and R 5 are each H atoms.
  • each of R 2 , R 4 and R 5 are hydrogen. In another
  • R and R are the same.
  • At least one of the two radicals R 1 and R 3 has at least 4 carbon atoms, e.g. and one or more is n-butyl, hexyl or 2-ethylhexyl.
  • R 1 and R 3 are the same and are each, for example, methyl, ethyl or n-butyl.
  • imidazolium ions include, but are not limited to, l,2-dimethyl-3- propylimidazolium, l-ethyl-2,3-dimethylimidazolium, l-butyl-2,3-dimethylimidazolium, 1- benzyl-3-methylimidazolium, 3-ethyl-l-methylimidazolium, l-propyl-3-methylimidazolium, 3 -n-butyl- 1 -methylimidazolium, 1 -hexyl-3 -methylimidazolium, 1 -methyl-3 - octylimidazolium, l-decyl-3-methylimidazolium, l-dodecyl-3 -methylimidazolium, 1,3- diethylimidazolium, 1,3-diisopropylimidazolium, 1,3-di-n-butylimid
  • the imidazolium ion is chosen from 3-ethyl-l-methylimidazolium, 1,3-diethylimidazolium, 1,3- dihexylimidazolium, and 1,3-di-n-butylimidazolium.
  • this anion is typically an aromatic or heteroaromatic carboxylate anion.
  • a " is an aromatic carboxylate anion.
  • Suitable non- limiting examples of the anion A " are the anions of aromatic carboxylic acids such as benzoic acid, 2-, 3- or 4-methylbenzoic acid, 3,5-dimethylbenzoic acid, 2-, 3- or 4-chlorobenzoic acid, 2,3-, 2,4-, 2,5- or 3,4-dichlorobenzoic acid, 2-, 3- or 4-cyanobenzoic acid, 2-, 3- or 4- methoxybenzoic acid, 2-, 3- or 4-nitrobenzoic acid, 2,4-dinitrobenzoic acid, salicylic acid, 3- hydroxy-4-methylbenzoic acid, acetylsalicylic acid, 2-, 3- or 4-aminobenzoic acid, 4- dimethylaminobenzoic acid, 4-diethyl-aminobenzoic acid, phthalic acid, isophthal
  • the anion is an anion of benzoic acid.
  • the anion is chosen from acetate, thocyanate, tetrafluoroborate, dicyanamide, trifluoromethanesulfonate, methylsulfate, diethylphosphate, ethylsulfate, chloride, and methane sulfonate .
  • the synthesis of such imidazolium ions with carboxylate anions as a counterion is described, for example, in WO 2009/040242.
  • the synthesis of the symmetrical imidazolium salts is described, for example, in WO 2009/074535 A2.
  • the synthetic workup may be as described in WO 2009/027250 A2.
  • the synthesis and identity of the catalyst may also be as described in US 20150322289.
  • R 2 may be n-alkyl radical with chain length as per the table below:
  • the catalyst is l-methyl-3-vinylimidazolium carboxylate, more particularly l-methyl-3-vinylimidazolium benzoate; l-benzyl-3-methylimidazolium carboxylate, more particularly l-benzyl-3-methylimidazolium benzoate.
  • each of R 1 and R 3 is independently an organic radical having 1 to 20, e.g. 1 to 6, carbon atoms and that optionally includes one or more heteroatoms such as oxygen atoms, nitrogen, sulfur atoms, or phosphorus atoms.
  • the organic radical may also include or be a functional group, e.g. a hydroxyl group, an ether group, an ester group, or a carbonyl group. These groups could be aliphatic or aromatic but are typically aliphatic.
  • Each of R 2 , R 4 and R 5 is independently a hydrogen atom or a hydrocarbon having 1 to 20 carbon atoms.
  • A is benzoate
  • R 2 , R 4 , and R 5 are each H
  • R 1 is ethyl
  • R 3 is methyl.
  • the catalyst may be EMIMBz, which is l-Ethyl-3-methylimidazolium benzoate.
  • the composition may also include one or more additives or be free of any one or more additives, such as those described below.
  • Fillers based on magnesium silicate hydrate such as, for example, talc, based on aluminum hydroxide such as, for example, Al(OH)3, based on a feldspar, based on quartz powder and/or based on a calcium silicate and/or aluminum silicate may be used and may have a particle size from 1 to 20 micrometers. Adding one or more fillers may serve to improve the mechanical properties of the composition.
  • the fillers are chosen from calcium silicate, magnesium silicate hydrate, aluminum silicate, quartz powder and/or aluminum hydroxide such as, for example, aluminum trihydrate. Fillers based on CaC0 3 , Ti0 2 , carbon black and/or BaS0 4 as well as fillers with a significant Fe content and/or containing additional heavy metals may be used.
  • Plasticizers such as, but not limited to, aliphatic oils, waxes, fatty acid salts, resins derived from alkylated phenols and esters, and combinations thereof.
  • the composition includes one or more fillers such as, but not limited to, microspheres, polystyrene foam, polyacrylates, polyolefins, silica, aluminum/silica, aluminum silicate, calcium carbonate, coated polyvinylidene, calcium silicates, fumed silica, precipitated silica, polyethylene, Calcium carbonate, carbon black, calcined clay, talc, silica, silicate fillers, rutile titanium dioxide, zeolites, and combinations thereof.
  • fillers such as, but not limited to, microspheres, polystyrene foam, polyacrylates, polyolefins, silica, aluminum/silica, aluminum silicate, calcium carbonate, coated polyvinylidene, calcium silicates, fumed silica, precipitated silica, polyethylene,
  • the composition includes one or more adhesion promoters such as, but not limited to, methylon AP-108, Duerz 16674, Bakelite BRL 3741, Resinex 468, silanes, phenolic resins, polysulfides, epoxy functional molecules, and combinations thereof.
  • adhesion promoters such as, but not limited to, methylon AP-108, Duerz 16674, Bakelite BRL 3741, Resinex 468, silanes, phenolic resins, polysulfides, epoxy functional molecules, and combinations thereof.
  • the composition includes surfactants, such as those known in the art, thixotropic agents such as sepiolite and those known in the art, solvents such as organic solvents, ethyl acetate, terphenyls, hydrogenated terphenyls, toluene, and those known in the art, and/or pigments such as titanium dioxide, zinc sulfide, carbon black, organic and inorganic pigments, and those known in the art, and combinations thereof.
  • the composition includes photosensitizers and/or photo initiators, or combinations thereof.
  • the composition maybe free of any one or more such additives.
  • the composition may include or be free of one or more of calcium carbonate, butanone, toluene, titanium dioxide, Ethanethiol, 2,2,-thiobis-l reaction products with reduced l,l'-[methylenebis(oxy)]bis [2-chloroethane]-sodium sulfide (Na2 (Sx)-l,2,3-trichloropropane polymer, ethyl acetate, hydrogenated Terphenyls, Zeolites, quarter- and higher, partially hydrogenated Polyphenyls, Talc, carbon black, magnesium carbonate, 1,3-diphenylguanidine, bis(piperidinothiocarbonyl) tetrasulphide, photo initiators, photosensitizers such as benzophenone, isopropyl thioxanthone, aluminum silicate, phenolic resins, Sepiolite, NaAl-based zeolite, phosphorous acid esters, monomeric
  • Lightweight fillers in particular those based on polyurethane including their copolymers, polyamide wax and/or polyolefin wax may also be used. Lightweight fillers may also be used to reduce the density of the composition and/or sealant. Alternatively or additionally, hollow filing bodies may also be used.
  • Thixotropy agents in particular based on feldspar, silicic acid/silica, sepiolite and/or bentonite may be used to adjust rheological properties, in particular for thixotropic behavior, of the composition.
  • Plasticizers in particular based on an adipate, a benzoate, a citrate, a phthalate, an ester of a polyethylene glycol, and/or a terphenyl may be used, for example, to increase the flexibility of the composition and/or sealant.
  • Adhesion promoters in particular those based on a phenolic resin, a resol and/or a silane/silanol/siloxane, e.g.
  • mercaptopropyltrimethoxysilane, mercaptopropyltriethoxysilane, glycidoxypropyltrimethoxysilane, glycidoxypropyltriethoxysilane, methacryloxymethyl trimethoxysilane and/or (methacryloxymethyl)methyldimethoxysilane and/or a bis-silylsilane may be used to improve the adhesion of the composition and/or sealant to a substrate.
  • Anti-aging agents may also be used such as sterically hindered phenols, phenyleneamine and/or hindered amine light stabilizers such as 4,6-bis(dodecylthiomethyl)- o-cresol, ethylene-bis(oxyethylene)bis(3-(5-tert-butyl-4-hydroxy-m-tolyl)propionate- , thiodiethylene-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate) and/or phenylene amines such as, for example, N-isopropyl-N'-phenyl-p-phenylenediamine. Anti-aging agents may be used to scavenge the free radicals formed due to aging processes involving the composition and may contribute to delaying and/
  • Water scavengers e.g. those based on an organofunctional alkoxysilane, based on a zeolite such as an alkali aluminum zeolite and/or based on a mono functional isocyanate may also be used.
  • Flame retardants in particular those based on phosphate esters, based on ammonium polyphosphate, based on melamine, based on aluminum hydroxide and/or based on magnesium hydroxide may also be used to improve the fire prevention behavior of the composition and/or sealant such as, for example, to delay the onset of burning of the sealant, to spontaneously terminate the burning process and/or to reduce the formation of smoke.
  • Vulcanization promoters may also be used such as diphenylguanidine, thiuram, and/or sulfur (e.g. sulfur paste).
  • At least one organic solvent in particular based on an ester and/or an ether such as, for example, ethyl acetate and/or monopropylene glycol monomethyl ether can be used.
  • the one or more additives may be present in an amount of from 0 to 40, 0.1 to 10, from 0.1 to 5, or from 0.1 to 2, parts by weight per 100 parts by weight of the composition or per 100 parts by weight of "Part A” and/or "Part B", described below. In other embodiments, the one or more additive may be present in an amount of from 0.01 to 5, from 0.1 to 5, or from 0.1 to 2, parts by weight per 100 parts by weight of the composition or per 100 parts by weight of "Part A” and/or "Part B", described below.
  • the one or more additive may be present in an amount of from 0.01 to 40, from 0.2 to 1, from 10 to 40, from 1 to 10, or from 5 to 10, parts by weight per 100 parts by weight of the composition or per 100 parts by weight of "Part A" and/or "Part B", described below.
  • all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • This disclosure also provides a sealant system, e.g. a two-part system.
  • this system includes a first component including, consisting essentially of, or consisting of, the polysulfide and the catalyst, and a second component including, consisting essentially of, or consisting of, the isocyanate and optionally one or more additives.
  • this system includes a first component including, consisting essentially of, or consisting of, the polysulfide and one or more optional additives, and a second component including, consisting essentially of, or consisting of, the isocyanate and the catalyst.
  • the terminology "consisting essentially of describes that the first and/or second component is free of other polymers, monomers, catalysts, etc.
  • the first component and the second component are utilized in an amount of 1 :1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, 10:1, 11:1, 12:1, 13:1, 14:1, 15:1, 16:1, 17:1, 18:1, 19:1, or 20:1, or vice versa, or any combinations thereof.
  • all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the first component may be alternatively described as "Part A" as first introduced above.
  • the second component may be alternatively described as "Part B" also introduced above.
  • the polysulfide and the isocyanate component are present in the composition in a weight ratio of from 16:1 to 2:1, referred as part A to Part B ratio for the two part sealant system.
  • the disclosure also provides a sealant, which may be described as the result of the composition after cure. Alternatively, the sealant may be described as a partially cured composition.
  • the composition cures typically using the mechanism based on the catalyst.
  • the catalyst itself can catalyze the reaction of the polysulfide and the isocyanate at room temperature.
  • UV light irradiation can also trigger the catalyst to release an amidine that can greatly accelerate a surface cure at depths of less than 200 um on a surface.
  • diffusion of the amidine in the composition matrix can surface cure up to 7mm.
  • the heat generated from a UV source or an external heat source can also accelerate the reaction of the polysulfide and the isocyanate and diffusion of amidine and therefore can improve bulk cure.
  • the catalyst of this disclosure has a different pH level than those of the art which allows for bulk cure rates to be customized by using catalysts with differing pH , e.g.
  • a synergistic effect may also be observed between UV and thermal curing, surface curing, and bulk curing, thereby allowing for design of cure on demand compositions in a wide range of applications including not only in aircraft sealant, automotive sealant, electronic sealant and construction sealants, but also in industrial coatings and adhesives applications.
  • the sealant may be described as the polymerization product of the polysulfide and the isocyanate reacted in the presence of the catalyst. This typically forms a thio-urethane.
  • the sealant may include, consist essentially of, or consist of, such a polymerization product.
  • the terminology "consist essentially of” describes embodiments that are free of polymers or co-polymers, of any known in the art, that are not the sealant itself, i.e., the polymerization product of the polysulfide and isocyanate reacted in the presence of the catalyst.
  • the composition cures to have a viscosity of greater than 1,000, 1,500, 2,000, 2,500, or 3,000 cps in 45, 40, 35, 30, 25, 20, 15, 10, or 5 minutes.
  • a maximum viscosity in 15, 10, or 5 minutes is greater than 1000 cps as measured using a viscometer such as a Brookfield DV-II + Pro with an appropriate spindle such as a #RV7 spindle.
  • the maximum viscosities in these times may be 10,000, 50,000, 100,000, 500,000, 1,000,000, 1,500,000, etc. up to about 350,000,000, cps, measured in the same way.
  • all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the composition cures to a tack-free time of from 0.05 to 5 minutes after the start of cure according to DIN 65262-1. In other embodiments, the composition cures to a tack-free time of less than 120, 115, 110, 105, 100, 96, 90, 85, 80, 75, 70, 65, 60, 55, 50, 45, 40, 35, 30, 25, 20, 15, 10,or 5, minutes, after the start of cure according to DIN 65262-1. In other embodiments, the sealant has a complete curing time or the time until reaching a Shore hardness of 30, determined according to ISO 7619 or ASTM D2240, from 1 to 960 min, of from 5 to 300 min, of from 10 to 60 min.
  • one or more portions of the sealant composition may have a density, determined according to ISO 2781, of from 0.9 to 1.6 g/cm or from 1.2 to 1.5 g/cm 3 . In various non-limiting embodiments, all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the sealant has a Shore A hardness, determined according to ISO 7619 and measured 2 weeks after cure in storage in air at 23 °C. and 50% relative atmospheric humidity, of from 20 to 80, of from 30 to 60, or of from 40 to 55. In additional embodiments, the sealant has a Shore A hardness of at least 10 within 30 to 180 minutes of curing.
  • the sealant has an elongation at break, determined according to ISO 37 and measured 2 weeks after cure during storage in air at 23 °C and 50% relative atmospheric humidity, of from 100 to 1000%, of from 200% to 800% or from 300% to 600%. In various non-limiting embodiments, all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the sealant has an elongation, determined according to ISO 37 and measured after 168 hours in storage in a fuel at 60°C, using the jet Al type of fuel, is of from 100 to 800%, of from 200 to 600% or of from 300 to 500%.
  • the sealant has an elongation at break of the sealants according to the invention, determined according to ISO 37 and measured after 300 hours in storage in fuel at 100°C, using the jet Al type of fuel is preferably of from 100 to 700%, especially preferably of from 200 to 600% or 400 to 500%.
  • the sealant has an elongation at break, determined according to ISO 37 and measured after 1000 hours in storage in water at 35°C, of from 100 to 700%, e.g. from 200 to 500% or 250 to 350%. In various non-limiting embodiments, all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the sealant has a peel resistance on aluminum alloy 2024 T3, determined according to DIN 65262-1, of from 60 to 350 N/25 mm, e.g. from 100 to 250 N/25 mm or 160 to 200 N/25 mm.
  • the sealant has a peel resistance on enamels, such as, for example, on base enamels including solvent such as, for example, epoxy base enamel 37035 A from Akzo Nobel Aerospace Coatings, on water-based base enamels such as, for example, those based on epoxy such as Seevenax 313-01 and Seevenax 313-02 from Mankiewicz, on cover enamels such as, for example, water-based top coats based on epoxies such as Seevenax 313-01 from Mankiewicz, on finish F 70-A from Mapaero and/or on solvent-containing top coats based on polyurethanes such as Aerodur 21-100 from Akzo Nobel and Alexit 406-22 from Mankiewicz, determined according to DIN 65262-1, of from 50 to 350 N/25 mm, e.g.
  • the peel resistance is determined on substrates of aluminum or aluminum alloys, of titanium or titanium alloys, of stainless steels, of composite materials such as, for example, carbon fiber-reinforced plastic CFP and/or on enamel substrates that have been enameled, for example, with at least one solvent-containing or water-based base coat and/or top coat, in particular based on epoxy, polyester or polyurethane enamel.
  • all values and ranges of values between the aforementioned values are hereby expressly contemplated.
  • the sealant has a tensile strength, determined according to ISO 37 and measured after 2 weeks after UV irradiation with storage in air at 23 °C. and 50% relative atmospheric humidity, of from 0.5 to 3.5 MPa, e.g. from 1 to 3 MPa or 1.8 to 2.7 MPa.
  • the sealant has a tensile strength, determined according to ISO 37 and measured after 168 hours at 60°C in storage in fuel of jet Al type, is of from 0.5 to 3 MPa, e.g. of from 1 to 2.5 or 1.5 to 2 MPa.
  • the sealant has a tensile strength, determined according to ISO 37 and measured after 300 hours at 100°C.
  • the sealant in storage in fuel of jet Al type, of from 0.5 to 3 MPa, e.g. from 1 to 2 or 0.8 to 1.1 MPa.
  • the sealant has a tensile strength, determined according to ISO 37 and measured after 1000 hours at 35°C in storage in water, of from 0.5 to 3 MPa, e.g. of from 1 to
  • the sealant exhibits no cracks or other defects that occur in determination of low temperature flexibility due to bending at an angle of 30 degrees at a temperature of -55°C, a tensile strength of from 0.5 to 2.8 MPa after 168 hours of storage in a fuel at a temperature of 60°C, after 300 hours of storage in a fuel at a temperature of 100°C, and after 1000 hours of storage in water at a temperature of 35°C, an elongation at break of from 100 to 800% after 168 hours of storage in fuel at a temperature of 60°C, after 300 hours of storage in a fuel at a temperature of 100°C, and after 1000 hours of storage in water at a temperature of 35°C and/or a density of from 1.00 to 1.45 g/cm 3 .
  • the sealant as the following properties after complete curing: a tensile strength of from 0.5 to
  • This disclosure also provides an article that includes a substrate and the composition and/or (cured or partially cured) sealant disposed thereon.
  • the article may be one used in the aviation industry, but may also be used wherever a rapid and complete curing and especially a very rapid surface curing with a relatively long sealant processing time are necessary and/or advantageous.
  • the article may be a tank or area to be sealed.
  • the composition and/or sealant may be used for plastering as in gas stations and chemical installations, for example, for connecting structural elements placed on top of one another such as sheet metal, films and other substrates, for filling cavities and intermediate spaces, for coating metallic materials in particular and composites such as, for example, carbon fiber reinforced or glass fiber reinforced plastics, for aerodynamic smoothing and compaction as well as for preventing corrosion in locations where the anticorrosion layers of the metallic elements have been damaged or removed, for example, in the area of boreholes.
  • a load-bearing function may also be fulfilled, for example, during shipping.
  • the article is used in the shipping industry such as, for example, in automotive engineering, in the construction of rail vehicles, in shipbuilding, in the airplane construction industry or in the spacecraft construction industry, in machine and equipment construction, in the building industry or for the production of furniture.
  • the article is an aircraft fuel tank.
  • the article is further defined as a construction article, aircraft/aerospace article, motor or rail vehicle, ship, machine, glass insulation, and/or furniture.
  • the article is further defined as glass insulation.
  • This disclosure also provides a method of forming the curable sealant composition wherein the method includes the steps of providing the polysulfide, the isocyanate component, and the catalyst and combining the polysulfide, the isocyanate component, and the catalyst to form the curable composition.
  • This disclosure farther provides a method of forming the cured sealant wherein the method includes the steps of providing the polysulfide, the isocyanate component, and the catalyst and combining the polysulfide, the isocyanate component, and the catalyst such that the polysulfide polymerizes with the isocyanate component in the presence of the catalyst to form the cured sealant.
  • this disclosure provides a method of forming the article wherein the method includes the steps of providing the polysulfide, the isocyanate component, and the catalyst and applying the polysulfide, the isocyanate component, and the catalyst onto the substrate such that the polysulfide polymerizes with the isocyanate component in the presence of the catalyst and forms the cured sealant disposed on the substrate.
  • This method also provides a method of cure-on-demand triggered by UV irradiation wherein one or more catalysts are used to adjust processing time and cure time; surface cure time and bulk cure time.
  • the sealant is triggered by UV irradiation.
  • a developed sealant may be capable of curing in darkness with a time lag and also capable of continuing to cure after a UV source is removed.
  • This disclosure also provides a method to achieve cure-on-demand for thicknesses significantly larger that traditional cure- on-demand systems. For example, the system and method of this disclosure could cure up to more than 10mm of thickness.
  • each step of providing may be any known in the art.
  • any step of combining may be any known in the art such that any one or more of the aforementioned components may be combined in any order and as a whole or in parts.
  • the step of applying may be further defined as dipping, pouring, spraying, brushing, or any other method of application known in the art.
  • any one or more of the aforementioned additives may be utilized and combined with any one or more of the aforementioned components in any one or more steps of the method.
  • heat and/or UV light may also be used as part of the method.
  • one or more components of the method maybe heated to a temperature of from 10 to 100, 20 to 90, or 20 to 80, °C, to cure the components.
  • UV light at wavelengths of from 310 to 380, from 280 to 310, or from 270 to 310, nm, may be used to cure the components.
  • the article, the curable composition, and/or the composition after curing have one or more of the following:
  • an Elongation Before Jet Fuel Test of from 150 to 1500, 200 to 1450, 250 to 1400, 300 to 1350, 350 to 1300, 400 to 1250, 450 to 1200, 500 to 1150, 550 to 1100, 600 to 1050, 650 to 1000, 700 to 950, 750 to 900, 800 to 850, 100 to 500, 150 to 450, 200 to 400, 250 to 350, 300 to 350, 160 to 290, 170 to 300, 165 to 295, 170 to 290, 175 to 285, 180 to 280, 185 to 275, 190 to 270, 195 to 265, 200 to 260, 205 to 255, 210 to 250, 215 to 245, 220 to 240, 225 to 235, or 225 to 230, % as determined using ASTM D 412.
  • the curable composition, and/or the composition after curing has an Elongation Before Jet Fuel Test of from 200 to 500, 250 to 450, 300 to 400, or 350 to 400, % as determined using ASTM D
  • an Elongation After Jet Fuel Test of from 150 to 1500, 200 to 1450, 250 to 1400, 300 to 1350, 350 to 1300, 400 to 1250, 450 to 1200, 500 to 1150, 550 to 1100, 600 to 1050, 650 to 1000, 700 to 950, 750 to 900, 800 to 850, 100 to 500, 150 to 450, 200 to 400, 250 to 350, 300 to 350, 160 to 290, 170 to 300, 165 to 295, 170 to 290, 175 to 285, 180 to 280, 185 to 275, 190 to 270, 195 to 265, 200 to 260, 205 to 255, 210 to 250, 215 to 245, 220 to 240, 225 to 235, or 225 to 230, % as determined using ASTM D 412.
  • the curable composition, and/or the composition after curing has an Elongation After Jet Fuel Test of from 300 to 500, 350 to 450, or 400 to 450, % as determined using ASTM D 412.
  • a Strength Before Jet Fuel Test of from 150 to 1500, 200 to 1450, 250 to 1400, 300 to 1350, 350 to 1300, 400 to 1250, 450 to 1200, 500 to 1150, 550 to 1100, 600 to 1050, 650 to 1000, 700 to 950, 750 to 900, 800 to 850, 100 to 500, 150 to 450, 200 to 400, 250 to 350, 300 to 350, 160 to 290, 170 to 300, 165 to 295, 170 to 290, 175 to 285, 180 to 280, 185 to 275, 190 to 270, 195 to 265, 200 to 260, 205 to 255, 210 to 250, 215 to 245, 220 to 240, 225 to 235, 225 to 230, 200 to 400, 250 to 350, 300 to 350, 160
  • the curable composition, and/or the composition after curing has a Strength Before Jet Fuel Test of from 200 to 1000, 250 to 950, 300 to 900, 350 to 850, 400 to 800, 450 to 750, 500 to 700, 550 to 650, or 600 to 650, % as determined using ASTM D 412.
  • a Strength after Jet Fuel Test of 150 to 1500, 200 to 1450, 250 to 1400, 300 to 1350, 350 to 1300, 400 to 1250, 450 to 1200, 500 to 1150, 550 to 1100, 600 to 1050, 650 to 1000, 700 to 950, 750 to 900, 800 to 850, 100 to 500, 150 to 450, 200 to 400, 250 to 350, 300 to 350, 160 to 290, 170 to 300, 165 to 295, 170 to 290, 175 to 285, 180 to 280, 185 to 275, 190 to 270, 195 to 265, 200 to 260, 205 to 255, 210 to 250, 215 to 245, 220 to 240, 225 to 235, 225 to 230, 200 to 400, 250 to 350, 300 to 350, 250 to 300, 255 to 295, 260 to 290, 265 to 285, 270 to 280, or 275 to 280, psi as determined using ASTM D 412.
  • the curable composition, and/or the composition after curing has a Strength after Jet Fuel Test of from 150 to 800, 200 to 750, 250 to 700, 300 to 650, 350 to 600, 400 to 550, or 450 to 500, % as determined using ASTM D 412.
  • a Strength after Jet Fuel Test of from 150 to 800, 200 to 750, 250 to 700, 300 to 650, 350 to 600, 400 to 550, or 450 to 500, % as determined using ASTM D 412.
  • compositions are formed by mixing Parts A and B as shown below. After mixing Parts A and B, various physical properties are determined, as shown below.
  • Catalyst 1 is
  • A is benzoate
  • R 2 , R 4 , and R 5 are each H
  • R 1 is ethyl
  • R 3 is methyl
  • Tack Free Time (min) is determined using ASTM C679 test.
  • Shore A is determined using ASTM D2240 test.
  • Elongation Before Jet Fuel Test (%) is determined using ASTM D 412 test.
  • Jet Fuel Test Weight Loss (%) is determined using in house weight loss method test.
  • one or more elements, components, compounds, method steps, etc. from one or both of concurrently filed provisional applications can be utilized.
  • Each of these provisional applications is expressly incorporated herein by reference in its entirety relative to these non- limiting embodiments.
  • an expressly contemplated embodiment may include any one or more elements described above selected and combined from any portion of the disclosure.
  • One or more of the values described above may vary by ⁇ 5%, ⁇ 10%, ⁇ 15%, ⁇ 20%, ⁇ 25%, etc. so long as the variance remains within the scope of the disclosure. Unexpected results may be obtained from each member of a Markush group independent from all other members. Each member maybe relied upon individually and or in combination and provides adequate support for specific embodiments within the scope of the appended claims.
  • any ranges and subranges relied upon in describing various embodiments of the present disclosure independently and collectively fall within the scope of the appended claims, and are understood to describe and contemplate all ranges including whole and/or fractional values therein, even if such values are not expressly written herein.
  • One of skill in the art readily recognizes that the enumerated ranges and subranges sufficiently describe and enable various embodiments of the present disclosure, and such ranges and subranges may be further delineated into relevant halves, thirds, quarters, fifths, and so on. As just one example, a range "of from 0.1 to 0.9" may be further delineated into a lower third, i.e.
  • a range of "at least 10" inherently includes a subrange of from at least 10 to 35, a subrange of from at least 10 to 25, a subrange of from 25 to 35, and so on, and each subrange may be relied upon individually and/or collectively and provides adequate support for specific embodiments within the scope of the appended claims.
  • an individual number within a disclosed range may be relied upon and provides adequate support for specific embodiments within the scope of the appended claims.
  • a range "of from 1 to 9" includes various individual integers, such as 3, as well as individual numbers including a decimal point (or fraction), such as 4.1, which may be relied upon and provide adequate support for specific embodiments within the scope of the appended claims.

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Abstract

La présente invention concerne une composition de matériau d'étanchéité durcissable qui comprend un polysulfure comportant un groupe -SH, un constituant isocyanate, et un catalyseur ayant la structure : dans laquelle chacun des R1 et R3 représente indépendamment un radical organique ayant de 1 à 20 atomes de carbone, chacun des R2, R4 et R5 représente indépendamment H ou un radical organique ayant de 1 à 20 atomes de carbone, et A¯ représente un anion.
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