US20050245695A1 - Polymer blend and compositions and methods for using the same - Google Patents

Polymer blend and compositions and methods for using the same Download PDF

Info

Publication number
US20050245695A1
US20050245695A1 US10/935,856 US93585604A US2005245695A1 US 20050245695 A1 US20050245695 A1 US 20050245695A1 US 93585604 A US93585604 A US 93585604A US 2005245695 A1 US2005245695 A1 US 2005245695A1
Authority
US
United States
Prior art keywords
sealant
polysulfide
polymer blend
component
polythioether
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/935,856
Inventor
Michael Cosman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
PRC-DeSoto International Inc
Original Assignee
PRC-DeSoto International Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to US10/837,337 priority Critical patent/US20040220327A1/en
Application filed by PRC-DeSoto International Inc filed Critical PRC-DeSoto International Inc
Priority to US10/935,856 priority patent/US20050245695A1/en
Assigned to PRC-DESOTO INTERNATIONAL, INC. reassignment PRC-DESOTO INTERNATIONAL, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: COSMAN, MICHAEL A.
Publication of US20050245695A1 publication Critical patent/US20050245695A1/en
Application status is Abandoned legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00Compositions of 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; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/02Polythioethers; Polythioether-ethers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00Compositions of 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; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/04Polysulfides
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/28Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2848Three or more layers
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31533Of polythioether

Abstract

A polymer blend having at least one polysulfide component and at least one polythioether component is disclosed. The polymer blend offers numerous advantages, including the ability to compatibilize formulations based on either polysulfide chemistry or polythioether chemistry alone. Compositions comprising the polymer blend, particularly sealant formulations for use in aerospace applications, are also disclosed, as are multilayer sealant assemblies and methods for repairing the same.

Description

    CROSS REFERENCE TO RELATED APPLICATIONS
  • This application is a continuation-in-part of Ser. No. 10/837,337, filed Apr. 30, 2004.
  • FIELD OF THE INVENTION
  • The present invention relates to a polymer blend comprising at least one polysulfide component and at least one polythioether component.
  • BACKGROUND INFORMATION
  • Sulfur-containing polymers are known to be well suited for use in aerospace sealants due to their fuel resistant nature upon crosslinking. Polysulfide sealants offer high tensile strength, high tear strength, thermal resistance and resistance to high ultraviolet light. Such sealants also offer resistance to fuel and maintain their adhesion upon exposure to fuel.
  • Various sulfur-containing polymers, including for example thiol-terminated sulfur-containing polymers and polysulfide polymers, are used in commercially available sealant formulations. It is often desirable to use different sealant formulations in combination to achieve the desired properties contributed by each. For example, a sealant prepared from a polysulfide has good chemical resistance, whereas a sealant prepared with a polythioether has a lower Tg and a higher service temperature. Use of sealant formulations having different chemistries together, however, can often have long-term compatibility problems. The present invention addresses this issue.
  • SUMMARY OF THE INVENTION
  • The present invention is generally directed to a polymer blend comprising at least one polysulfide component and at least one polythioether component. Sealants comprising this blend and a curing agent are further within the scope of the invention.
  • DETAILED DESCRIPTION OF THE INVENTION
  • The present invention is directed to a polymer blend comprising at least one polysulfide component and at least one polythioether component.
  • The “polysulfide component” of the present invention comprises a polysulfide polymer that contains multiple sulfur-sulfur linkages, i.e., —[S—S]—, in the polymer backbone and/or in the terminal or pendant positions on the polymer chain. Typically, the polysulfide polymers in the present invention will have two or more sulfur-sulfur linkages. Suitable polysulfides are commercially available from Akzo Nobel under the name THIOPLAST. THIOPLAST products are available in a wide range of molecular weights ranging, for example, from less than 1100 to over 8000, with molecular weight being the average molecular weight in grams per mole. Particularly suitable is a number average molecular weight of 1000 to 4000. The crosslink density of these products also varies, depending on the amount of crosslinking agent used. The “—SH” content, i.e. the mercaptan content, of these products can also vary. The mercaptan content and molecular weight of the polysulfide can affect the cure speed of the blend, with cure speed increasing with molecular weight.
  • In some embodiments, it is desired to use a combination of polysulfides to achieve the desired molecular weight and/or crosslink density in the polymer blend. Different molecular weights and/or crosslink densities can contribute different characteristics to the blend and compositions incorporating the blend. For example, blends wherein the polysulfide component comprises more than one polysulfide polymer and one of the polysulfide polymers has a molecular weight of approximately 1000 have desirable non-crystallization properties.
  • The second component in the polymer blend of the present invention is a polythioether. The “polythioether component” of the present invention is a polymer comprising at least one polythioether linkage, i.e., —[—CH2—CH2—S—CH2—CH 2—]—. Typical polythioethers have from 8 to 200 of these linkages. Polythioethers suitable for use in the present invention include those described in U.S. Pat. No. 6,372,849. Suitable polythioethers typically have a number average molecular weight of 1000 to 10,000, such as 2,000 to 5,000 or 3,000 to 4,000. In some embodiments, the polythioether component will be terminated with non-reactive groups, such as alkyl, and in other embodiments will contain reactive groups in the terminal or pendant positions. Typical reactive groups are thiol, hydroxyl, amino, vinyl and epoxy. For a polythioether component that contains reactive functional groups, the average functionality typically ranges from 2.05 to 3.0, such as from 2.1 to 2.6. A specific average functionality can be achieved by suitable selection of reactive ingredients. Examples of suitable polythioethers are available from PRC-Desoto International, Inc., under the trademark PERMAPOL, such as PERMAPOL P-3.1e or PERMAPOL P-3. As with the polysulfide component, combinations of polythioethers can be used to prepare the polythioether component according to the present invention.
  • The polymer blends of the present invention can-be prepared according to any standard means known in the art, such as by mixing the polysulfide component and polythioether component and blending in a standard mixer such as a cowls mixer or planetary mixer. The ratio of polysulfide component to polythioether component in the blend can range from 10:90 to 90:10. A 50:50 ratio is particularly suitable for some embodiments, such as when making a Class A sealant. The molecular weight of the present polymer blend is typically from 1,000 to 8,000, such as 3,500 to 4,500, as measured theoretically or using GPC. The Tg of the polymer blend is typically −70° C. or lower, such as −60° C. or lower. The viscosity of the blend will typically be lower than the viscosity of a polysulfide having a comparable molecular weight; this contributes to ease of handling and use of the present blend and can minimize if not eliminate the need for solvents in certain sealants.
  • In some embodiments it may be desirable to further mix the polymer blend of the present invention with other polymers or additives to control various physical performance parameters of the blend. For example, the blend, with its relatively fast cure (i.e. faster than eight hours), can be mixed with a polymer having a relatively slow cure (i.e. greater than eight hours), to get the desired cure rate. In this embodiment, a suitable slow curing polymer is the reaction product of a polysulfide, DMDS, and an amine. Such a product is commercially available from PRC-DeSoto International, Inc. as PERMAPOL P.5.
  • A particularly suitable use for the blend of the present invention is in all classes of sealants. “Sealant” and like terms refer to compositions that have the ability to resist atmospheric conditions such as moisture and temperature and at least partially block transmission of materials such as water, fuel, and other liquids and gases. Sealants often have adhesive properties, as well. Sealants are generally identified by “Class”, based on their viscosity. Class A sealants generally have a viscosity of 100 to 400 poise. Because these sealants are typically brush-applied, they are often referred to as a “brush coat”. Class B sealants typically have a viscosity of 6000 to 18000 poise, and are typically applied through use of an extrusion gun or a spatula. These sealants are typically used on a fillet seal, and are commonly used as fuel tank sealants. Class C sealants generally have a viscosity between that of Class A and Class B sealants, such as from 1000 to 4000 poise. Class C sealants can be applied in various manners, such as with a brush, roller or extrusion gun, and are typically used for “fay seal”. Different classes of sealant are often used in combination. When different chemistries are present in the different sealants, compatibility issues can arise, particularly long-term compatibility. For example, the application of a polythioether-containing sealant on a cured polysulfide-containing sealant may fail over time. Compositions comprising the polymer blend of the present invention are extremely effective in promoting adhesion between a polysulfide-containing sealant and a polythioether-containing sealant. Because polysulfide chemistries and polythioether chemistries tend to be incompatible, it was surprising that the present polymer blends could be prepared, and then used in a sealant formulation. Indeed, a blend comprising a polysulfide sealant formulation and a polythioether sealant formulation could not be made.
  • In addition to its ability to promote compatibility or adhesion between two different sealant layers, the combination of polysulfide and polythioether chemistries in the present invention provides for the desired properties of each chemistry to be combined in one formulation. For example, in some embodiments, the blend has a lower viscosity than a polysulfide formulation, and a greater cold temperature stability than a polysulfide formulation and greater chemical resistance than a polythioether formulation. The cure rate of compositions comprising the present polymer blend are also faster than compositions comprising either polysulfide or polythioether alone. It is particularly desirable that aerospace sealants have a relatively long application time, (i.e., the time during which the sealant remains usable) and short curing time (i.e. the time required to reach a predetermined strength). Compositions comprising the present polymer blend can have an application time of about one hour and a cure time of about six hours.
  • The present polymer blends, as well as the compositions in which they are incorporated, also have a relatively low glass transition temperature (“Tg”) (i.e. ≦−70° C.). A low Tg is desired in many aerospace applications as it is indicative of good low temperature flexibility. Tg can be determined by known methods, for example, by DSC, DMA, or TMA, and by methods similar to those described in ASTM (American Society for Testing and Materials) D 522-88. In addition, the present polymers and compositions have excellent performance and handling properties and in some embodiments have good adhesion to various substrates.
  • The present invention is further directed to a composition comprising the polymer blend of the present invention. A particularly suitable composition is one used as a sealant. Sealants, according to the present invention, can be prepared having many different viscosities. Class A sealants prepared using the polymer blend of the present invention, i.e., having a viscosity of from about 100 to 400 poise, often require less solvent than other Class A sealants since the polymer blend has a lower viscosity than polysulfide alone. Class A sealants of the present invention, therefore, offer an environmental advantage. Class B sealants prepared using the present polymer blend, i.e., sealants having a viscosity of 6000 to 18000, often have a lower Tg and higher temperature resistance than Class B sealants prepared with polysulfide alone, and a better chemical resistance than sealants prepared with a polythioether alone. The present polymer blends can also be used in the preparation of Class C sealants, which have a viscosity of 1000 to 4000 poise.
  • As noted above, certain embodiments of the present polymer blends, and compositions comprising these blends, can be non-crystallizing. “Non-crystallizing” and like terms refer to polymers that are liquid at ambient temperature, and are not semi-crystalline waxes, gums, or solids. A non-crystallizing polymer, even when cooled to a sufficiently low temperature to become a solid, will be an amorphous solid which, when the temperature is raised to ambient, will return to the liquid state. Accordingly, the present invention is further directed to a noncrystallizing composition comprising a polymer blend comprising at least one polysulfide component and at least one polythioether component. In one embodiment, the molecular weight of the polysulfide component in the noncrystallizing composition is less than 1500, such as about 1000.
  • In addition to the polysulfide/polythioether blend described above, the compositions of the present invention typically further comprise a curing agent and one or more additional additives. The term “curing agent” refers to a material that can be added to the present polymer blend to accelerate the curing or gelling of the blend. “Curing” or “cure” refers to the point at which the sealant achieves a cure hardness of 30 Durometer “A” as measured according to ASTM D2240. Any suitable curing agent can be used. In certain embodiments, the curing agent contains oxidizing agents that oxidize terminal mercaptan groups to form disulfide bonds. Suitable oxidizing curing agents include, for example, lead dioxide, manganese dioxide, calcium dioxide, sodium perborate monohydrate, calcium peroxide, zinc peroxide, dichromate and epoxy. Other suitable curing agents may contain reactive functional groups that are reactive with the functional groups in the polymer blend. Examples include but are not limited to polythiols such as polythioethers; polyisocyanates such as isophorone, diisocyanate, and hexamethylene diisocyanate including mixtures thereof and including isocyanurate derivatives thereof; and polyepoxides. Examples of polyepoxides include hydantoin diepoxide, bisphenol-A epoxides, bisphenol-F epoxides, novolac type epoxides, aliphatic polyepoxides, and any of the epoxidized unsaturated and phenolic resins. The term “polyepoxide” refers to a material having a 1,2-epoxy equivalent greater than one and includes monomers, oligomers, and polymers.
  • Various additives such as fillers, adhesion promoters and plasticizers can also be used in the present compositions. Fillers useful in the present compositions, especially for aerospace applications, include those commonly used in the art, such as carbon black, calcium carbonate (CaCO3), silica, nylon and the like. Potting compound fillers include high band gap materials such as zinc sulfide and inorganic barium compounds. In one embodiment, the compositions include about 10 to about 70 weight percent of the selected filler or combination of fillers, such as about 10 to 50 weight percent based upon the total weight of the composition.
  • One or more adhesion promoters can also be used. Suitable adhesion promoters include phenolics such as METHYLON phenolic resin available from Occidental Chemicals, organosilanes such as epoxy, mercapto or amino functional silanes such as A-187 and A-1100 available from Osi Specialties. An adhesion promoter can be used in an amount from. 0.1 to 15 weight percent based upon total weight of the formulation.
  • A plasticizer can be used in the compositions in an amount ranging from 1 to 8 weight percent based upon total weight of the formulation. Useful plasticizers include phthalate esters, chlorinated paraffins, and hydrogenated terphenyls.
  • The compositions can further comprise one or more organic solvents, such as isopropyl alcohol, in an amount ranging from 0 to 15 percent by weight on a basis of total weight of the formulation, such as less than 15 weight percent or less than 10 weight percent.
  • Compositions of the present invention can also optionally include other standard additives, such as pigments; thixotropes; retardants; catalysts; and masking agents.
  • Useful pigments include those conventional in the sealant art, such as carbon black and metal oxides. Pigments can be present in an amount from about 0.1 to about 10 weight percent based upon total weight of the composition.
  • Thixotropes, for example fumed silica or carbon black, can be used in an amount from about 0.1 to about 5 weight percent based upon total weight of the composition.
  • Compositions of the present invention typically comprise 20 to 70 weight percent, such as 35 to 50 weight percent of the present polymer blend; from 1 to 50 weight percent, such as 5 to 25 weight percent or about 10 weight percent of a curing agent; and 10 to 50 weight percent, such as 5 to 30 weight percent or about 25 weight percent of other additives, with weight percent being based on the total weight of the composition.
  • The present compositions are typically packaged as a two-component or “2K” systems. One component comprises the polymer blend of the present invention and various additives, such as filler(s), extender(s), adhesion promoter(s), accelerator(s), and/or (retardant(s); the second component generally comprises the curing agent and various additives, such as plasticizer(s), filler(s), accelerator(s), and/or retardant(s). The two components are then mixed immediately prior to use. For example, the two components can be mixed using a specially adapted cartridge/rod system such as that commercially available from PRC-DeSoto International, Inc. as SEMKIT. Alternatively, the components can be mixed together and the mixture maintained at a temperature below that at which the curing agent is reactive. The term “reactive” means capable of chemical reaction and includes any level of reaction from partial to complete reaction of a reactant. A storage temperature of below about −40° C. is typically suitable to retard or prevent the reaction between the curing agent and the polysulfide and/or polythioether components of the polymer blend.
  • Because the compositions of the present invention find particular application in compatibilizing polysulfide and polythioether chemistries, the present compositions, when used in a sealant formulation, are particularly useful when making repairs. “Repair” is typically needed in the case of sealant leakage or damage. For example, a sealant having polysulfide chemistry may be deposited on a substrate. If a polythioether layer was deposited directly on top of the polysulfide layer, it would not maintain compatibility over the long term with the already-cured. polysulfide layer. Application of the present sealant to the already-cured polysulfide layer facilitates adhesion with the subsequently deposited polythioether layer. Accordingly, the present invention is further directed to a method for repairing a sealant comprising applying the present composition to an already-cured first sealant, and depositing a second sealant onto the composition of the present invention; either the first or second sealant utilizes polysulfide chemistry and the other utilizes polythioether chemistry. The second sealant can be deposited onto the composition of the present invention at any time, such as while it is still wet, when it has undergone sufficient cure so as to be “tack-free”, or after more advanced levels of curing.
  • A multilayer sealant combination is also the subject of the present invention, comprising a first sealant layer, and a second sealant layer, wherein a layer of the sealant of the present invention is between the first sealant layer and second sealant layer; again, either the first or second sealant layers will be based on polysulfide chemistry and the other will be based on polythioether chemistry.
  • The compositions of the present invention can be applied to any number of substrates including, for example, titanium, stainless steel, aluminum, and the primed, organic coated and chromate forms thereof, epoxy, urethane, graphite, fiber glass composite, KEVLAR, acrylics and polycarbonates. The present compositions are particularly useful in aerospace applications, such as aerospace sealants and the linings for fuel tanks, fuselages, and the like. An aerospace sealant material according to the present invention can exhibit properties including high temperature resistance, fuel resistance and flexural strength. The formulations described herein are also well suited for uses in which temperature extremes, chemically harsh environments and/or mechanical vibrations are experienced.
  • The polymer blend of the present invention is generally ungelled, which means that the polymer blend has an intrinsic viscosity that can be measured. The present polymer blends, however, as noted above, are capable of being cured with a suitable curing agent. The cured formulations of the present invention generally have good low temperature flexibility, which is desired in aerospace applications since the formulations are subjected to wide variations in environmental conditions, such as temperature and pressure, and physical conditions such as joint contraction and expansion and vibration.
  • Viscosities as reported herein are measured at a temperature of about 25° C. and a pressure of about 760 mm Hg determined according to ASTM D-2849, paragraphs 79-90 using a Brookfield Viscometer.
  • As used herein, unless otherwise expressly specified, all numbers such as those expressing values, ranges, amounts or percentages may be read as if prefaced by the word “about”, even if the term does not expressly appear. Any numerical range recited herein is intended to include all sub-ranges subsumed therein. Plural encompasses singular and vice versa. Also, as used herein, the term “polymer” is meant to refer to prepolymers, oligomers and both homopolymers and copolymers; the prefix “poly” refers to two or more.
  • EXAMPLE
  • The following example is intended to illustrate the invention, and should not be construed as limiting the invention in any way.
  • A Class A sealant was prepared by mixing the components listed in Table 1 in a double shaft cowls type batch mixer until homogeneous under a vacuum of 27 inches of mercury or greater. Component B represents the polymer blend of the present invention and Component A represents an accelerator. Components B and A were mixed in a weight ratio of 100:12 to prepare the final sealant. The sealant was tested to the requirements of BMS 5-45 Rev. B Class A Grade 1. For example, long-term compatibility of the sealant was tested. The sealant comprising the blend was applied over a cured polysulfide aerospace sealant that had been previously exposed to jet reference fluid; the sealant comprising the blend was allowed to cure to a tack-free condition and then a polythioether sealant was applied over the sealant comprising the blend, allowed to cure for 14 days, immersed in jet reference fluid at 140° F. for 42 days then tested for adhesion to BMS 5-45 Rev. B requirements. TABLE 1 Component A Ingredient Weight Percent Polythioether1 23.91 Polysulfide2 23.91 Phenolic resin3 0.71 Sulfur-containing Phenolic 0.47 Sulfur-containing Phenolic 0.30 Silica4 0.14 Silica5 3.32 Titanium dioxide6 1.90 Blue color paste7 0.95 Polyamide8 2.37 Sulfur9 0.06 Calcium carbonate10 19.00 Stearic acid 0.10 Polysulfide latex 0.66 Amino silane11 0.84 Ethyl acetate 7.12 Toluene 14.24
    1PERMAPOL P-3.1e from PRC-DeSoto International, Inc.

    2THIOPLAST G-1, LP-2 from Akzo Nobel.

    3METHYLON 75108, from Occidental Chemical or Durez Corp.

    4CAB-O-SIL TS-720, from Cabot Corp.

    5SIPERNAT D13, from Degussa Corp.

    6TI-PURE R-900, from DuPont.

    7SUNFAST BLUE, from Sun Chemical Corp.

    8ORGASOL, from Atofina.

    9Sulfur, rubber makers from Reagent Chemical and Research Inc..

    10SOCAL 31, from Solvay.

    11SILIQUEST A-1100, from OSI Corp., a Crompton Company.
  • Component B Ingredient Weight Percent MnO2 54.0 Plasticizer12 34.0 Stearic acid 0.6 Sodium stearate 0.7 Molecular sieve powder13 0.7 Dipentamethylene/thiuram/ 5.0 polysulfide mixture14 Silane adhesion promoter 5.0
    12Partially hydrogenated terphenyl (HB-40 from Solutia).

    13Alkali metal alumino-silicate 3-angstrom powder from UOP.

    14Akrochem Accelerator DPTT Powder from Akrochem Corp.
  • Whereas particular embodiments of this invention have been described above for purposes of illustration, it will be evident to those skilled in the art that numerous variations of the details of the present invention may be made without departing from the invention as defined in the appended claims.

Claims (23)

1. A polymer blend comprising:
a) at least one polysulfide component; and
b) at least one polythioether component.
2. The polymer blend of claim 1, wherein the ratio of a:b is 10:90 to 90:10.
3. The polymer blend of claim 2, wherein the ratio of a:b is 50:50.
4. The polymer blend of claim 1, wherein the polysulfide component comprises more than one polysulfide polymer.
5. The polymer blend of claim 4, wherein one polysulfide polymer in the polysulfide component has a molecular weight of 1000 and one polysulfide polymer in the polysulfide component has a molecular weight of 4000.
6. The polymer blend of claim 1, wherein the polysulfide component has a number average molecular weight of 1000 to 4000.
7. The polymer blend of claim 1, wherein the polythioether component has a number average molecular weight of 3000 to 4000.
8. The polymer blend of claim 7, wherein the polythioether component has an average functionality from 2.1 to 2.6.
9. The polymer blend of claim 1, having a Tg of −70° C., or less.
10. A non-crystallizing composition comprising the polymer blend of claim 1.
11. The non-crystallizing composition of claim 10, wherein the number average molecular weight of the polysulfide component is less than 1500.
12. A composition comprising the polymer blend of claim 1.
13. The composition of claim 12, having a viscosity of 100 to 400 poise.
14. The composition of claim 12, having a viscosity of 6000 to 18000 poise.
15. The composition of claim 13, having a viscosity of 1000 to 4000 poise.
16. A sealant composition comprising:
a) a polymer blend comprising:
i) at least one polysulfide component and
ii) at least one polythioether component; and
b) a curing agent.
17. The sealant of claim 16, wherein the curing agent comprises an oxidizing agent.
18. The sealant of claim 17, wherein the curing agent comprises manganese dioxide.
19. The sealant of claim 16, further comprising at least one additive selected from fillers, adhesion promoters, plasticizers, pigments, thixotropes, retardants, catalysts, and masking agents.
20. The sealant of claim 19 comprising a filler.
21. A method for repairing a first sealant, comprising:
a) applying the composition of claim 12 to the first sealant layer; and
b) applying a second sealant layer thereon;
wherein either the first or second sealant layer is based on polysulfide chemistry, and the other sealant layer is based on polythioether chemistry.
22. A multilayer sealant composition comprising:
a) a first sealant;
b) a second sealant; and
c) a sealant comprising a polymer blend comprising at least one polysulfide component and at least one polythioether component, wherein the sealant layer comprising the polymer blend is between the first sealant and the second sealant, and wherein either the first or second sealant is based on polysulfide chemistry and the other of the first or second sealant is based on polythioether chemistry.
23. A mixture comprising:
a) the polymer blend of claim 1; and
b) a polymer having a cure time of greater than eight hours.
US10/935,856 2003-04-30 2004-09-08 Polymer blend and compositions and methods for using the same Abandoned US20050245695A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10/837,337 US20040220327A1 (en) 2003-04-30 2004-04-30 Preformed EMI/RFI shielding compositions in shaped form
US10/935,856 US20050245695A1 (en) 2004-04-30 2004-09-08 Polymer blend and compositions and methods for using the same

Applications Claiming Priority (20)

Application Number Priority Date Filing Date Title
US10/935,856 US20050245695A1 (en) 2004-04-30 2004-09-08 Polymer blend and compositions and methods for using the same
ES05794862.2T ES2606664T3 (en) 2004-09-08 2005-09-02 Mixture of polymers and compositions and procedures for using them
AU2005282552A AU2005282552B2 (en) 2004-09-08 2005-09-02 Polymer blend and compositions and methods for using the same
ES10007548.0T ES2607502T3 (en) 2004-09-08 2005-09-02 Mixture of polymers and compositions and procedures for use
PCT/US2005/031694 WO2006029144A1 (en) 2004-09-08 2005-09-02 Polymer blend and compositions and methods for using the same
KR1020077005398A KR100934051B1 (en) 2004-09-08 2005-09-02 Polymer blends, compositions and their use methods
JP2007531264A JP4787836B2 (en) 2004-09-08 2005-09-02 Polymer blends and compositions and methods using the polymer blends
EP05794862.2A EP1797143B1 (en) 2004-09-08 2005-09-02 Polymer blend and compositions and methods for using the same
CN 200580030170 CN101014665B (en) 2004-09-08 2005-09-02 Polymer blend and compositions and methods for using the same
EP10007548.0A EP2239300B1 (en) 2004-09-08 2005-09-02 Polymer blend and compositions and methods for using the same
UAA200703760A UA87519C2 (en) 2004-09-08 2005-09-02 Polymer blend and compositions and methods for using the same
RU2007112922A RU2391363C2 (en) 2004-09-08 2005-09-02 Polymer mixture, composition based on said mixture and method of reparing sealing material
CA 2579661 CA2579661C (en) 2004-09-08 2005-09-02 Polymer blend and compositions and methods for using the same
IL18175207A IL181752A (en) 2004-09-08 2007-03-06 Multilayer sealant and a method for repairing a first sealant
US12/106,620 US7598326B2 (en) 2004-04-30 2008-04-21 Polymer blend and compositions and methods for using the same
US12/106,632 US7638162B2 (en) 2004-04-30 2008-04-21 Polymer blend and compositions and methods for using the same
US12/106,574 US7524564B2 (en) 2004-04-30 2008-04-21 Polymer blend and compositions and methods for using the same
US12/504,918 US7786226B2 (en) 2004-04-30 2009-07-17 Polymer blend and compositions and methods for using the same
JP2010043556A JP5570247B2 (en) 2004-09-08 2010-02-26 Polymer blends and compositions and methods using the polymer blends
IL22158912A IL221589A (en) 2004-09-08 2012-08-22 Polymer blend, a non-crystallizing composition, a composition comprising the polymer blend, a sealant composition and a method for repairing a first sealant layer

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US10/837,337 Continuation-In-Part US20040220327A1 (en) 2003-04-30 2004-04-30 Preformed EMI/RFI shielding compositions in shaped form

Related Child Applications (5)

Application Number Title Priority Date Filing Date
US12/106,574 Division US7524564B2 (en) 2003-04-30 2008-04-21 Polymer blend and compositions and methods for using the same
US12/106,620 Division US7598326B2 (en) 2003-04-30 2008-04-21 Polymer blend and compositions and methods for using the same
US12/106,620 Continuation US7598326B2 (en) 2003-04-30 2008-04-21 Polymer blend and compositions and methods for using the same
US12/106,632 Continuation US7638162B2 (en) 2003-04-30 2008-04-21 Polymer blend and compositions and methods for using the same
US12/106,632 Division US7638162B2 (en) 2003-04-30 2008-04-21 Polymer blend and compositions and methods for using the same

Publications (1)

Publication Number Publication Date
US20050245695A1 true US20050245695A1 (en) 2005-11-03

Family

ID=35457571

Family Applications (5)

Application Number Title Priority Date Filing Date
US10/935,856 Abandoned US20050245695A1 (en) 2003-04-30 2004-09-08 Polymer blend and compositions and methods for using the same
US12/106,632 Active US7638162B2 (en) 2003-04-30 2008-04-21 Polymer blend and compositions and methods for using the same
US12/106,574 Active US7524564B2 (en) 2003-04-30 2008-04-21 Polymer blend and compositions and methods for using the same
US12/106,620 Active US7598326B2 (en) 2003-04-30 2008-04-21 Polymer blend and compositions and methods for using the same
US12/504,918 Active US7786226B2 (en) 2003-04-30 2009-07-17 Polymer blend and compositions and methods for using the same

Family Applications After (4)

Application Number Title Priority Date Filing Date
US12/106,632 Active US7638162B2 (en) 2003-04-30 2008-04-21 Polymer blend and compositions and methods for using the same
US12/106,574 Active US7524564B2 (en) 2003-04-30 2008-04-21 Polymer blend and compositions and methods for using the same
US12/106,620 Active US7598326B2 (en) 2003-04-30 2008-04-21 Polymer blend and compositions and methods for using the same
US12/504,918 Active US7786226B2 (en) 2003-04-30 2009-07-17 Polymer blend and compositions and methods for using the same

Country Status (12)

Country Link
US (5) US20050245695A1 (en)
EP (2) EP2239300B1 (en)
JP (2) JP4787836B2 (en)
KR (1) KR100934051B1 (en)
CN (1) CN101014665B (en)
AU (1) AU2005282552B2 (en)
CA (1) CA2579661C (en)
ES (2) ES2607502T3 (en)
IL (2) IL181752A (en)
RU (1) RU2391363C2 (en)
UA (1) UA87519C2 (en)
WO (1) WO2006029144A1 (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080200610A1 (en) * 2004-04-30 2008-08-21 Prc-Desoto International, Inc. Polymer blend and compositions and methods for using the same
WO2008137198A1 (en) * 2007-05-01 2008-11-13 Prc-Desoto International, Inc. Sealant composition comprising polythioether
WO2012129088A1 (en) 2011-03-18 2012-09-27 Prc-Desoto International, Inc. Multifunctional sulfur-containing polymers, compositions thereof and methods of use
WO2012129090A1 (en) 2011-03-18 2012-09-27 Prc-Desoto International, Inc. Terminal-modified difunctional sulfur-containing polymers, compositions thereof and methods of use
WO2012141841A1 (en) 2011-03-18 2012-10-18 Prc-Desoto International, Inc. Polyurea compositions and methods of use
US20130295290A1 (en) * 2012-05-03 2013-11-07 Ppg Industries Ohio, Inc. Compositions with a sulfur-containing polymer and graphenic carbon particles
WO2016004008A1 (en) 2014-06-30 2016-01-07 Prc-Desoto International, Inc. Polyurea compositions and methods of use
US20160300646A1 (en) * 2015-04-08 2016-10-13 The Boeing Company Core-shell particles, compositions incorporating the core-shell particles and methods of making the same
US9580635B2 (en) 2011-03-18 2017-02-28 Prc-Desoto International, Inc. Polyurea compositions and methods of use
WO2018057337A1 (en) * 2016-09-21 2018-03-29 3M Innovative Properties Company Polysulfide or polythioether sealant composition including glycol organic acid esters

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8092128B1 (en) * 2007-02-20 2012-01-10 Bray Alan V Self-sealing fasteners
US9080004B2 (en) 2010-10-07 2015-07-14 Prc-Desoto International, Inc. Diethylene glycol monomethyl ether resistant coating
BR112013010824A2 (en) 2010-11-02 2018-05-02 Systems And Materials Res Corporation method and mechanism for making and using an automatic seal fastener
BR112015007871A2 (en) 2012-10-11 2017-07-04 Prc Desoto Int Inc method for preparing a neutralized base aqueous resin dispersion
US9029437B2 (en) 2011-09-14 2015-05-12 Prc-Desoto International, Inc. Coating/sealant systems, aqueous resinous dispersions, methods for making aqueous resinous dispersions, and methods of electrocoating
US9181628B2 (en) 2011-09-14 2015-11-10 Prc-Desoto International, Inc. Coating/sealant systems, aqueous resinous dispersions, and methods of electrocoating
US8901256B2 (en) 2012-01-12 2014-12-02 Prc-Desoto International, Inc. Polythioethers, moisture curable compositions and methods for their manufacture and use
DE102012205951B4 (en) 2012-04-12 2016-09-01 Chemetall Gmbh Sealant system, uncured base material and mixture, hardener, method for coating a substrate and use of a sealant system
US8871896B2 (en) 2012-06-21 2014-10-28 Prc Desoto International, Inc. Michael addition curing chemistries for sulfur-containing polymer compositions
US8952110B2 (en) 2012-06-21 2015-02-10 Prc-Desoto International, Inc. Moisture-curable, amine-catalyzed sulfur-containing polymer compositions
EP2881418A4 (en) 2012-08-01 2016-04-27 Toray Finechemicals Co Ltd Thiol group-containing polymer and curable composition thereof
US9328275B2 (en) 2014-03-07 2016-05-03 Prc Desoto International, Inc. Phosphine-catalyzed, michael addition-curable sulfur-containing polymer compositions
US9518197B2 (en) 2014-03-07 2016-12-13 Prc-Desoto International, Inc. Cure-on-demand moisture-curable urethane-containing fuel resistant prepolymers and compositions thereof
CA2952792A1 (en) * 2014-06-18 2015-12-23 Ppg Industries Ohio, Inc. Elastic gas barrier coating compositions
US9422451B2 (en) * 2015-01-09 2016-08-23 Prc-Desoto International, Inc. Low density fuel resistant sulfur-containing polymer compositions and uses thereof
US10035926B2 (en) 2016-04-22 2018-07-31 PRC—DeSoto International, Inc. Ionic liquid catalysts in sulfur-containing polymer compositions
US10370561B2 (en) 2016-06-28 2019-08-06 Prc-Desoto International, Inc. Urethane/urea-containing bis(alkenyl) ethers, prepolymers prepared using urethane/urea-containing bis(alkenyl) ethers, and uses thereof

Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2450940A (en) * 1944-04-20 1948-10-12 John C Cowan Polyamides from polymeric fat acids
US2466963A (en) * 1945-06-16 1949-04-12 Thiokol Corp Polysulfide polymer
US3499863A (en) * 1963-09-23 1970-03-10 Thiokol Chemical Corp Air-curable polysulfide-polyurethane sealants
US3659896A (en) * 1970-03-17 1972-05-02 Thiokol Chemical Corp Adhesive semi-cured sealing strip for automobile windshield
US4020033A (en) * 1974-08-29 1977-04-26 Hooker Chemicals & Plastics Corporation Polythioether sealant compositions
US4137361A (en) * 1975-01-13 1979-01-30 Graham Magnetics Incorporated Powder products
US4366307A (en) * 1980-12-04 1982-12-28 Products Research & Chemical Corp. Liquid polythioethers
US4606848A (en) * 1984-08-14 1986-08-19 The United States Of America As Represented By The Secretary Of The Army Radar attenuating paint
US4689395A (en) * 1985-03-14 1987-08-25 Ruetgerswerke Aktiengesellschaft Anhydrous thermosetting adhesive/sealant composition comprising mercapto terminated polymer and MnO2 hardener
US5284888A (en) * 1989-12-28 1994-02-08 Chomerics, Inc. Corrosion inhibiting EMI/RFI shielding composition and method of its use
US5482655A (en) * 1992-06-17 1996-01-09 Ciba-Geigy Corporation Electrically conductive thermoplastic polymer formulations and the use thereof
US5866273A (en) * 1990-03-20 1999-02-02 The Boeing Company Corrosion resistant RAM powder
US6184280B1 (en) * 1995-10-23 2001-02-06 Mitsubishi Materials Corporation Electrically conductive polymer composition
US6201100B1 (en) * 1997-12-19 2001-03-13 Moltech Corporation Electroactive, energy-storing, highly crosslinked, polysulfide-containing organic polymers and methods for making same
US20010052591A1 (en) * 2000-03-09 2001-12-20 Kovalev Igor P. Methods for preparing non-corrosive, electroactive, conductive organic polymers
US6358437B1 (en) * 1997-12-23 2002-03-19 Bayer Aktiengesellschaft Screen printing paste for producing electrically conductive coatings
US6372849B2 (en) * 1997-02-19 2002-04-16 Prc-Desoto International, Inc. Sealants and potting formulations including polymers produced by the reaction of a polythiol and polyvinyl ether monomer
US6426863B1 (en) * 1999-11-25 2002-07-30 Lithium Power Technologies, Inc. Electrochemical capacitor
US6461458B1 (en) * 1999-04-20 2002-10-08 Bae Systems Plc Method of sealing a panel to an aircraft structure
US6486297B2 (en) * 2000-03-09 2002-11-26 Pbt Brands, Inc. High strength polymers and aerospace sealants therefrom
US6486822B1 (en) * 2000-06-07 2002-11-26 The Boeing Company Chemically modified radar absorbing materials and an associated fabrication method
US20030065062A1 (en) * 2001-09-14 2003-04-03 Corvasce Filomeno Gennaro Preparation of starch reinforced rubber and use thereof in tires

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56109275A (en) * 1980-01-31 1981-08-29 Yokohama Rubber Co Ltd:The Nonstaining polysulfide-based sealing material
US4623711A (en) * 1985-08-21 1986-11-18 Products Research & Chemical Corp. Modified disulfide polymer composition and method for making same from mercaptan terminated disulfide polymer and diethyl formal mercaptan terminated polysulfide
JPH0768456B2 (en) * 1989-10-18 1995-07-26 東レチオコール株式会社 Polymer composition
JPH041267A (en) * 1990-04-18 1992-01-06 Toray Chiokoole Kk Curable composition
US5225472A (en) * 1992-05-19 1993-07-06 Courtaulds Aerospace, Inc. Low viscosity polythiol and method therefor
AT243232T (en) * 1997-02-19 2003-07-15 Prc Desoto Int Inc Composition and method for producing liquid, fuel-resistant polymers with high flexibility at low temperature
US5971030A (en) 1997-06-06 1999-10-26 Maimets; Lembit Apparatus and method for repairing pressure pipes and for securing other elements with a curable sealant
JP2001522896A (en) 1997-11-03 2001-11-20 カール・ギールニク Plastic material
US6069211A (en) * 1997-11-07 2000-05-30 Courtaulds Aerospace, Inc. Chromate-free, one-part, non-curing corrosion inhibitive sealant with resistance to aviation fuel
RU2144553C1 (en) 1998-04-29 2000-01-20 Центральный научно-исследовательский институт технологии судостроения Method of attaching elastic coating to metal surfaces
US6486268B2 (en) * 2000-03-09 2002-11-26 Pbt Brands, Inc. Sealants containing multimodal polymer blends
US7067612B2 (en) * 2003-01-30 2006-06-27 Prc-Desoto International, Inc. Preformed compositions in shaped form
UA81885C2 (en) * 2004-09-08 2008-02-11 Прк-Дэсото Интэрнэшнл, Инк. Preformed compositions in shaped form comprising polymer blends and method for sealing apertures
US20050245695A1 (en) * 2004-04-30 2005-11-03 Cosman Michael A Polymer blend and compositions and methods for using the same
MXPA05011558A (en) * 2003-04-30 2005-12-14 Prc Desoto Int Inc Preformed emi/rfi shielding compositions in shaped form.
US7097883B2 (en) * 2003-06-05 2006-08-29 Ppg Industries Ohio, Inc. Low temperature liquid polythioether polymers

Patent Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2450940A (en) * 1944-04-20 1948-10-12 John C Cowan Polyamides from polymeric fat acids
US2466963A (en) * 1945-06-16 1949-04-12 Thiokol Corp Polysulfide polymer
US3499863A (en) * 1963-09-23 1970-03-10 Thiokol Chemical Corp Air-curable polysulfide-polyurethane sealants
US3659896A (en) * 1970-03-17 1972-05-02 Thiokol Chemical Corp Adhesive semi-cured sealing strip for automobile windshield
US4020033A (en) * 1974-08-29 1977-04-26 Hooker Chemicals & Plastics Corporation Polythioether sealant compositions
US4137361A (en) * 1975-01-13 1979-01-30 Graham Magnetics Incorporated Powder products
US4366307A (en) * 1980-12-04 1982-12-28 Products Research & Chemical Corp. Liquid polythioethers
US4606848A (en) * 1984-08-14 1986-08-19 The United States Of America As Represented By The Secretary Of The Army Radar attenuating paint
US4689395A (en) * 1985-03-14 1987-08-25 Ruetgerswerke Aktiengesellschaft Anhydrous thermosetting adhesive/sealant composition comprising mercapto terminated polymer and MnO2 hardener
US5284888A (en) * 1989-12-28 1994-02-08 Chomerics, Inc. Corrosion inhibiting EMI/RFI shielding composition and method of its use
US5866273A (en) * 1990-03-20 1999-02-02 The Boeing Company Corrosion resistant RAM powder
US5482655A (en) * 1992-06-17 1996-01-09 Ciba-Geigy Corporation Electrically conductive thermoplastic polymer formulations and the use thereof
US6184280B1 (en) * 1995-10-23 2001-02-06 Mitsubishi Materials Corporation Electrically conductive polymer composition
US6372849B2 (en) * 1997-02-19 2002-04-16 Prc-Desoto International, Inc. Sealants and potting formulations including polymers produced by the reaction of a polythiol and polyvinyl ether monomer
US6201100B1 (en) * 1997-12-19 2001-03-13 Moltech Corporation Electroactive, energy-storing, highly crosslinked, polysulfide-containing organic polymers and methods for making same
US6358437B1 (en) * 1997-12-23 2002-03-19 Bayer Aktiengesellschaft Screen printing paste for producing electrically conductive coatings
US6461458B1 (en) * 1999-04-20 2002-10-08 Bae Systems Plc Method of sealing a panel to an aircraft structure
US6426863B1 (en) * 1999-11-25 2002-07-30 Lithium Power Technologies, Inc. Electrochemical capacitor
US20010052591A1 (en) * 2000-03-09 2001-12-20 Kovalev Igor P. Methods for preparing non-corrosive, electroactive, conductive organic polymers
US6486297B2 (en) * 2000-03-09 2002-11-26 Pbt Brands, Inc. High strength polymers and aerospace sealants therefrom
US6486822B1 (en) * 2000-06-07 2002-11-26 The Boeing Company Chemically modified radar absorbing materials and an associated fabrication method
US20030065062A1 (en) * 2001-09-14 2003-04-03 Corvasce Filomeno Gennaro Preparation of starch reinforced rubber and use thereof in tires

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080200610A1 (en) * 2004-04-30 2008-08-21 Prc-Desoto International, Inc. Polymer blend and compositions and methods for using the same
US20080199603A1 (en) * 2004-04-30 2008-08-21 Prc-Desoto International, Inc. Polymer blend and compositions and methods for using the same
US7598326B2 (en) * 2004-04-30 2009-10-06 Prc Desoto International, Inc. Polymer blend and compositions and methods for using the same
US7638162B2 (en) * 2004-04-30 2009-12-29 Prc Desoto International, Inc. Polymer blend and compositions and methods for using the same
WO2008137198A1 (en) * 2007-05-01 2008-11-13 Prc-Desoto International, Inc. Sealant composition comprising polythioether
US20090012244A1 (en) * 2007-05-01 2009-01-08 Prc-Desoto International, Inc. Compositions including a polythioether
JP2010526173A (en) * 2007-05-01 2010-07-29 ピーアールシー−デソト インターナショナル,インコーポレイティド Sealant composition comprising a polythioether
US7879955B2 (en) 2007-05-01 2011-02-01 Rao Chandra B Compositions including a polythioether
US9382447B2 (en) 2011-03-18 2016-07-05 Prc-Desoto International, Inc. Multifunctional sulfur-containing polymers, compositions thereof and methods of use
WO2012129090A1 (en) 2011-03-18 2012-09-27 Prc-Desoto International, Inc. Terminal-modified difunctional sulfur-containing polymers, compositions thereof and methods of use
WO2012141841A1 (en) 2011-03-18 2012-10-18 Prc-Desoto International, Inc. Polyurea compositions and methods of use
US8507617B2 (en) 2011-03-18 2013-08-13 Prc-Desoto International, Inc. Polyurea compositions and methods of use
US8541513B2 (en) 2011-03-18 2013-09-24 Prc-Desoto International, Inc. Terminal-modified difunctional sulfur-containing polymers, compositions thereof and methods of use
WO2012129088A1 (en) 2011-03-18 2012-09-27 Prc-Desoto International, Inc. Multifunctional sulfur-containing polymers, compositions thereof and methods of use
US20130310531A1 (en) * 2011-03-18 2013-11-21 Prc-Desoto International, Inc. Terminal-modified difunctional sulfur-containing polymers, compositions thereof and methods of use
US8680214B2 (en) * 2011-03-18 2014-03-25 Prc Desoto International, Inc. Terminal-modified difunctional sulfur-containing polymers, compositions thereof and methods of use
US8729216B2 (en) 2011-03-18 2014-05-20 Prc Desoto International, Inc. Multifunctional sulfur-containing polymers, compositions thereof and methods of use
US8889800B2 (en) 2011-03-18 2014-11-18 Prc-Desoto International, Inc. Terminal-modified difunctional sulfur-containing polymers, compositions thereof and methods of use
US9012592B2 (en) 2011-03-18 2015-04-21 Prc-Desoto International, Inc. Multifunctional sulfur-containing polymers, compositions thereof and methods of use
US9109089B2 (en) 2011-03-18 2015-08-18 Prc-Desoto International, Inc. Multifunctional sulfur-containing polymers, compositions thereof and methods of use
US9580635B2 (en) 2011-03-18 2017-02-28 Prc-Desoto International, Inc. Polyurea compositions and methods of use
US9260567B2 (en) 2011-03-18 2016-02-16 Prc-Desoto International, Inc. Multifunctional sulfur-containing polymers, compositions thereof and methods of use
US20130295290A1 (en) * 2012-05-03 2013-11-07 Ppg Industries Ohio, Inc. Compositions with a sulfur-containing polymer and graphenic carbon particles
WO2016004008A1 (en) 2014-06-30 2016-01-07 Prc-Desoto International, Inc. Polyurea compositions and methods of use
US20160300646A1 (en) * 2015-04-08 2016-10-13 The Boeing Company Core-shell particles, compositions incorporating the core-shell particles and methods of making the same
US9856359B2 (en) * 2015-04-08 2018-01-02 The Boeing Company Core-shell particles, compositions incorporating the core-shell particles and methods of making the same
WO2018057337A1 (en) * 2016-09-21 2018-03-29 3M Innovative Properties Company Polysulfide or polythioether sealant composition including glycol organic acid esters

Also Published As

Publication number Publication date
US20080200610A1 (en) 2008-08-21
EP1797143B1 (en) 2016-11-09
JP4787836B2 (en) 2011-10-05
US7598326B2 (en) 2009-10-06
KR20070040840A (en) 2007-04-17
US7786226B2 (en) 2010-08-31
US20100003525A1 (en) 2010-01-07
AU2005282552B2 (en) 2008-09-11
IL181752D0 (en) 2007-07-04
US7638162B2 (en) 2009-12-29
CA2579661A1 (en) 2006-03-16
IL221589A (en) 2014-01-30
ES2607502T3 (en) 2017-03-31
US20080199603A1 (en) 2008-08-21
RU2391363C2 (en) 2010-06-10
CN101014665B (en) 2011-08-03
AU2005282552A1 (en) 2006-03-16
EP2239300B1 (en) 2016-11-09
IL221589D0 (en) 2012-10-31
ES2606664T3 (en) 2017-03-27
IL181752A (en) 2013-01-31
US20080199694A1 (en) 2008-08-21
WO2006029144A1 (en) 2006-03-16
EP1797143A1 (en) 2007-06-20
UA87519C2 (en) 2009-07-27
EP2239300A1 (en) 2010-10-13
CN101014665A (en) 2007-08-08
JP2010132924A (en) 2010-06-17
KR100934051B1 (en) 2009-12-24
JP2008512554A (en) 2008-04-24
JP5570247B2 (en) 2014-08-13
US7524564B2 (en) 2009-04-28
CA2579661C (en) 2010-05-25
RU2007112922A (en) 2008-10-20

Similar Documents

Publication Publication Date Title
US3225017A (en) Modified polysulfide composition
US6355317B1 (en) Thermoplastic moisture cure polyurethanes
US5849832A (en) One-component chemically curing hot applied insulating glass sealant
KR100534168B1 (en) Composition and method for producing fuel resistant liquid polythioether polymers with good low temperature flexibility
US6796102B2 (en) Insulating glass unit with structural primary sealant system
US6548593B2 (en) Thixotropic agent
US7834105B2 (en) Thiol-, hydroxyl-, amine- or vinyl-terminated polythioethers
EP1078012B1 (en) Composition and method for producing polythioethers having pendent methyl chains
AU652439B2 (en) Moisture curable polyurethane composition
CN103025797B (en) Polythioether polymers, their preparation, and compositions containing thereof
KR101226337B1 (en) High modulus, nonconductive adhesive based on polyurethane prepolymers useful for installing vehicle windows
EP0811656B1 (en) Double-glazed unit comprising resin composition
US4623711A (en) Modified disulfide polymer composition and method for making same from mercaptan terminated disulfide polymer and diethyl formal mercaptan terminated polysulfide
US4595718A (en) Fluorocarbon polymer compositions
CA1330846C (en) Fast-cure polyurethane sealant composition containing titanium ester accelerators
US3659896A (en) Adhesive semi-cured sealing strip for automobile windshield
US5367036A (en) Moisture-curable urethane-based sealing composition
US5714563A (en) One-part, low viscosity, moisture curable composition
RU2444537C2 (en) Sealing compound containing polythioether
CA2275779C (en) Composition and method for producing fuel resistant liquid polythioether polymers with good low temperature flexibility
EP0857186A4 (en) Thermosetting resin compositions
EP0601021A4 (en) Silane containing polyurethane polymer and adhesive composition.
CA2402113A1 (en) Chemically resistant polythioethers and formation thereof
EP0603342B1 (en) Coating compositions containing urethane and epoxy components and articles coated thereof
AU2013277251B2 (en) Copolymerizable sulfur-containing adhesion promoters and compositions thereof

Legal Events

Date Code Title Description
AS Assignment

Owner name: PRC-DESOTO INTERNATIONAL, INC., CALIFORNIA

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:COSMAN, MICHAEL A.;REEL/FRAME:015783/0277

Effective date: 20040902

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION