Sealant composition having reduced permeability to gas

• US 7,569,653 B2
• Filed: 02/01/2006
• Issued: 08/04/2009
• Est. Priority Date: 02/01/2006
• Status: Active Grant

• Current Assignee: Momentive Performance Materials Incorporated (Momentive Performance Materials Holdings LLC)
• Original Assignee: Momentive Performance Materials Incorporated (Momentive Performance Materials Holdings LLC)
• Inventors: Landon, Shayne J.
• Primary Examiner(s): Gulakowski; Randy
• Assistant Examiner(s): LOEWE, ROBERT S
• Application Number:
  US11/345,563
• Publication Number:
  US 20070179242A1
• Time in Patent Office: 1,280 Days
• Field of Search: 524/588, 525/106
• US Class Current: 528/65
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: C03C 27/10 with the aid of adhesive specially adapted for that purpose
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/289 containing silicon
• CPC Class Codes: C08G 18/4825 Polyethers containing two hydroxy groups C08G18/4833 - C08G18/5096 take precedence
• CPC Class Codes: C08G 18/718 containing silicon
• CPC Class Codes: C08G 2190/00 Compositions for sealing or packing joints
• CPC Class Codes: C08J 2300/108 containing hydrolysable silane groups
• CPC Class Codes: C08J 2375/04 Polyurethanes
• CPC Class Codes: C08J 5/005 Reinforced macromolecular compounds with nanosized materials, e.g. nanoparticles, nanofibres, nanotubes, nanowires, nanorods or nanolayered materials
• CPC Class Codes: C08L 101/10 containing hydrolysable silane groups
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials

Abstract

This invention relates to a moisture-curable silylated resin-containing composition containing, inter alia, moisture-curable silylated resin, the cured composition exhibiting low permeability to gas(es).

Claims

1. A moisture-curable silylated resin-containing composition comprising:

a) moisture-curable silylated resin, prepared by reacting a hydroxyl-terminated polyurethane prepolymer with and isocyanatosilane, wherein the hydroxyl terminated prepolymer is prepared by reacting a molar excess of a polyol selected from the group consisting of poly(oxyethylene) diols, poly(oxypropylene) diols, poly(oxyethylene-oxypropylene) diols, polyoxyalkylene triols and polytetramethylene glycols, having a number average molecular weight of from 4,000 to 18,000 grams/mole and an end group unsaturation level no greater than 0.04 milliequivalent per gram of polyol with a diisocyanate and wherein the isocyanatosilane is of the formula;

OCN—

R⁵—

Si(R⁶)_y(OR⁷)_3-y

 

where R⁵ is an alkylene group of up to 12 carbon atoms;

R⁶ is a alkyl or aryl group of up to 8 carbon atoms;

R⁷ is the same or different alkyl group of up to 6 carbon atoms; and

y is 0, 1 or 2

which upon curing, provides a cured resin exhibiting permeability to gas;

b) at least one other polymer having a permeability to gas that is less than the permeability of cured resin (a); and

,

c) at least one nanoclay modified with a cationic surfactant-exfoliating agent, wherein the nanoclay particles have a lateral dimension of between 0.01 microns and 5 microns and a vertical dimension of between 0.5 nanometers to 10 nanometers.

2. The composition of claim 1 wherein moisture-curable silylated resin (a) ranges from about 10 to about 50 weight percent of the total composition.

3. The composition of claim 1 wherein moisture-curable silylated resin (a) ranges from about 20 to about 30 weight percent of the total composition.

4. The composition of claim 1 wherein polymer (b) is selected from the group consisting of low density polyethylene, very low density polyethylene, linear low density polyethylene, high density polyethylene, polypropylene, polyisobutylene, polyvinyl acetate, polyvinyl alcohol, polystyrene, polycarbonate, polyester, such as, polyethylene terephthalate, polybutylene terephthalate, polyethylene napthalate, glycol-modified polyethylene terephthalate, polyvinylchloride, polyvinylidene chloride, polyvinylidene fluoride, thermoplastic polyurethane, acrylonitrile butadiene styrene, polymethylmethacrylate, polyvinyl fluoride, polyamides, polymethylpentene, polyimide, polyetherimide, polyether ether ketone, polysulfone, polyether sulfone, ethylene chlorotrifluoroethylene, polytetrafluoroethylene, cellulose acetate, cellulose acetate butyrate, plasticized polyvinyl chloride, ionomers, polyphenylene sulfide, styrene-maleic anhydride, modified polyphenylene oxide, ethylene-propylene rubber, polybutadiene, polychloroprene, polyisoprene, polyurethane, styrene-butadiene-styrene, styrene-ethylene-butadiene-styrene, polymethylphenyl siloxane and mixtures thereof.

5. The composition of claim 4 wherein polymer (b) is selected from the group consisting of low density polyethylene, very low density polyethylene, linear low density polyethylene, high density polyethylene, and mixtures thereof.

6. The composition of claim 5 wherein polymer (b) is selected from the group consisting of low density polyethylene, very low density polyethylene, linear low density polyethylene, and mixtures thereof.

7. The composition of claim 1, wherein polymer (b) ranges from about 5 to about 50 weight percent of the total composition.

8. The composition of claim 1, wherein polymer (b) ranges from about 10 to about 20 weight percent of the total composition.

9. The composition of claim 1 further comprising a catalyst wherein the catalyst is a tin catalyst.

10. The composition of claim 1 wherein the tin catalyst is selected from the group consisting of dibutyltin dilaurate, dibutyltindiacetate, dibutyltindimethoxide, tinoctoate, isobutyltintriceroate, dibutyltinoxide, solubilized dibutyl tin oxide, dibutyltin bis-diisooctylphthalate, bis-tripropoxysilyl dioctyltindibutyltin bis-acetylacetone, silylated dibutyltin dioxide, carbomethoxyphenyl tin tris-uberate, isobutyltin triceroate, dimethyltin dibutyrate, dimethyltin di-neodecanoate, triethyltin tartarate, dibutyltin dibenzoate, tin oleate, tin naphthenate, butyltintri-2-ethylhexylhexoate, tinbutyrate, diorganotin bis β

-diketonates, and mixtures thereof.

11. The composition of claim 1 further comprising an adhesion promoter wherein the adhesion promoter is selected from the group consisting of N-2-aminoethyl-3-aminopropyltrimethoxysilane, 1,3,5-tris(trimethoxysilylpropyl)isocyanu rate, γ

-aminopropyltriethoxysilane, γ

-aminopropyltrimethoxysilane, aminopropyltrimethoxysilane, bis-γ

-(trimethoxysilylpropyl)amine, N-phenyl-γ

-aminopropyltrimethoxysilane, triaminofunctionaltrimethoxysilane, γ

-aminopropylmethyldiethoxysilane, γ

-aminopropylmethyldiethoxysilane, methacryloxypropyltrimethoxysilane, methylaminopropyltrimethoxysilane, γ

-glycidoxypropylethyldimethoxysilane, γ

-glycidoxypropyltrimethoxysilane, γ

-glycidoxyethyltrimethoxysilane, β

-(3,4-epoxycyclohexyl)propyltrimethoxysilane, β

-(3,4-epoxycyclohexyl)ethylmethyldimethoxysilane, isocyanatopropyltriethoxysilane, isocyanatopropylmethyldimethoxysilane, β

-cyanoethyltrimethoxysilane, γ

-acryloxypropyltrimethoxysilane, γ

-methacryloxypropylmethyldimethoxysilane, 4-amino-3,3,-dimethylbutyltrimethoxysilane, N-ethyl-3-trimethoxysilyl-2-methylpropanamine, and mixtures thereof.

12. The composition of claim 1 further comprising at least one additional filler wherein said at least one additional filler is selected from the group consisting of calcium carbonate, precipitated calcium carbonate, colloidal calcium carbonate, calcium carbonate treated with compounds such as stearic acid or stearate esters fumed silica, precipitated silica, silica gels, hydrophobized silicas, hydrophilic silica gels, crushed quartz, ground quartz, alumina, aluminum hydroxide, titanium hydroxide, clay, kaolin, bentonite montmorillonite, diatomaceous earth, iron oxide, carbon black and graphite, mica, talc, and mixtures thereof.

13. The composition of claim 1 wherein the nanoclay is selected from the group consisting of montmorillonite, sodium montmorillonite, calcium montmorillonite, magnesium montmorillonite, nontronite, beidellite, volkonskoite, laponite, hectorite, saponite, sauconite, magadite, kenyaite, sobockite, svindordite, stevensite, vermiculite, halloysite, aluminate oxides, hydrotalcite, illite, rectorite, tarosovite, ledikite, kaolinite and, mixtures thereof.

14. The composition of claim 13 wherein the nanoclay is modified with ammonium, primary alkylammonium, secondary alkylammonium, tertiary alkylammonium, quaternary alkylammonium, phosphonium derivatives of aliphatic, aromatic or arylaliphatic amines, phosphines or sulfides or sulfonium derivatives of aliphatic, aromatic or arylaliphatic amines, phosphines or sulfides.

15. The composition of claim 13 wherein the nanoclay is modified with at least one tertiary amine compound R³R⁴R⁵N and/or quarternary ammonium compound R⁵R⁶R⁷R⁸N⁺ X⁻

wherein R³, R⁴, R⁵, R⁶, R⁷ and R⁸ each independently is an alkyl, alkenyl or alkoxy silane group of up to 60 carbon atoms and X⁻

is an anion.

16. The composition of claim 1 further comprising a surfactant, wherein the surfactant is a nonionic surfactant selected from the group consisting of polyethylene glycol, polypropylene glycol, ethoxylated castor oil, oleic acid ethoxylate, alkylphenol ethoxylates, copolymers of ethylene oxide and propylene oxide and copolymers of silicones and polyethers, copolymers of silicones and copolymers of ethylene oxide and propylene oxide and mixtures thereof.

17. The composition of claim 16 wherein the non-ionic surfactant is selected from the group consisting of copolymers of ethylene oxide and propylene oxide, copolymers of silicones and polyethers, copolymers of silicones and copolymers of ethylene oxide and propylene oxide and mixtures thereof.

18. A sealant, adhesive or coating composition prepared with the moisture-curable silylated resin-containing-composition of claim 1.

19. A sealant, adhesive or coating composition prepared with polymer (b) of claim 4.

20. A sealant, adhesive or coating composition prepared with the nanoclay composition of claim 15.

21. The cured silylated resin-containing composition of claim 1.

22. The cured silylated resin-containing composition of claim 4.

23. The cured silylated resin-containing composition of claim 15.