# US 5,346,939 A · Water curable resin compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,346,939 A - Document ID: US5346939A - Status: Granted - Kind: A - Application number: 08/008,743 - Filed: 1993-01-25 - Granted: 1994-09-13 - Earliest claimed: 1993-01-25 - Assignees: Minnesota Mining and Manufacturing Company - Inventors: Dean M. Moren; Dean A. Ersfeld - Web page: https://patentgrep.com/patent/US5346939A ## CPC - C08L 101/10: containing hydrolysable silane groups - C08K 5/0091: {Complexes with metal-heteroatom-bonds} - C09D 5/34: Filling pastes (materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) ## Abstract The present invention provides a water-curable resin composition for use in the preparation of composite materials. The resin composition is composed of a water-reactive liquid organometallic compound having a viscosity of no greater than about 500,000 centipoise under ambient conditions; and a nonreactive organic thermoplastic polymer, having a number average molecular weight of at least about 1,000, mixed with the water-reactive liquid organometallic compound. Preferably, the water-reactive liquid organometallic compound is a compound of the formula (R.sup.1 O).sub.x MR.sup.2.sub.(y-x) wherein: each R.sup.1 is independently a substituted or unsubstituted C.sub.1 -C.sub.100 hydrocarbon group, optionally interrupted in the backbone by 1--10 nonperoxide--O--, --S--, --C(O)--, or --N-- groups; each R.sup.2 is independently selected from the group consisting of hydrogen and a substituted or unsubstituted C.sub.1 -C.sub.100 hydrocarbon group, optionally interrupted in the backbone by 1--10 nonperoxide--O--, --S--, --C(O)--, or --N-- groups; x is an integer between 1 and y, inclusive; y is the valence of M; and M is boron, aluminum, silicon, or titanium. ## Claims ### Claim 1 A water-curable polymer solution comprising: (a) about 30-99 wt-% of a water-reactive liquid organometallic compound having at least three hydrolyzable groups per molecule; and (b) about 1-70 wt-% of a nonreactive organic thermoplastic polymer, having a number average molecular weight of at least about 1,000, dissolved within the water-reactive liquid organometallic compound; wherein the polymer solution is stable at a temperature of about 0.degree.-100.degree. C. and is capable of curing upon exposure to water to form a composite material at a temperature of about 10.degree.-100.degree. C. ### Claim 2 (depends on 1) The water-curable polymer solution of claim 1 wherein the polymer solution is capable of curing at a temperature of about 10.degree.-80.degree. C. ### Claim 3 (depends on 1) The water-curable polymer solution of claim 1 wherein the polymer solution is capable of curing at a temperature of about 20.degree.-30.degree. C. ### Claim 4 (depends on 1) The water-curable polymer solution of claim 1 wherein the polymer solution contains substantially no organic solvent. ### Claim 5 (depends on 1) The water-curable polymer solution of claim 1 wherein the hydrolyzable groups are selected from the group consisting of halogen, alkoxy, alkenoxy, carboxy, amino, amide, dialkylaminooxy, ketoxime, and aldoxime. ### Claim 6 (depends on 1) The water-curable polymer solution of claim 1 wherein the nonreactive organic thermoplastic polymer is an alkoxy silane-functional polymer. ### Claim 7 (depends on 1) The water-curable polymer solution of claim 1 wherein the nonreactive organic thermoplastic polymer is a nonethercontaining condensation polymer. ### Claim 8 (depends on 7) The water-curable polymer solution of claim 7 wherein the condensation polymer is coupled to a hydrolyzable silane group through a urethane bond. ### Claim 9 (depends on 1) The water-curable polymer solution of claim 1 wherein the nonreactive organic thermoplastic polymer is an addition polymer. ### Claim 10 (depends on 9) The water-curable polymer solution of claim 9 wherein the addition polymer is a copolymer prepared from a (meth)acryloyloxyalkyl or vinyl functional hydrolyzable silane. ### Claim 11 (depends on 1) The water-curable polymer solution of claim 1 wherein the water-reactive liquid organometallic compound has a viscosity of no greater than about 1,000 centipoise. ### Claim 12 (depends on 1) The water-curable polymer solution of claim 1 further comprising a second water-reactive liquid organometallic compound having at least three hydrolyzable groups. ### Claim 13 (depends on 1) The water-curable polymer solution of claim 1 further comprising a second dissimilar nonreactive organic thermoplastic polymer. ### Claim 14 (depends on 1) The water-curable polymer solution of claim 1 wherein the nonreactive organic thermoplastic polymer is a copolymer. ### Claim 15 (depends on 1) The water-curable polymer solution of claim 1 wherein the polymer solution has a viscosity of about 100-500,000 centipoise. ### Claim 16 (depends on 1) The water-curable polymer solution of claim 1 further comprising an effective amount of a catalyst. ### Claim 17 (depends on 16) The water-curable polymer solution of claim 16 wherein the acid catalyst is selected from the group consisting of an alkane sulfonic acid, a perfluorocarboxylic acid, a bis(perfluoroalkylsulfonyl)methane, a dialkyl phosphate, and mixtures thereof. ### Claim 18 (depends on 1) The water-curable polymer solution of claim 1 wherein the polymer solution is capable of curing upon exposure to water without the generation of substantial heat. ### Claim 19 A water-curable polymer solution comprising: (a) about 40-60 wt-% of a water-reactive liquid organometallic compound having the formula (R.sup.1 O).sub.x MR.sup.2.sub.(y-x) wherein: (i) each R.sup.1 is independently a substituted or unsubstituted C.sub.1 -C.sub.100 hydrocarbon group, optionally interrupted in the backbone by 1--10 nonperoxide --0--, --S--, --C(O)--, or --N-- groups; (ii) each R.sup.2 is independently selected from the group consisting of hydrogen and a substituted or unsubstituted C.sub.1 -C.sub.100 hydrocarbon group, optionally interrupted in the backbone by 1--10 nonperoxide --0--, --S--, --C(O)--, or --N-- groups; (iii) x is an integer between 1 and y, inclusive; (iv) y is the valence of M; (v) M is selected from the group consisting of boron, aluminum, silicon, and titanium; and (b) about 40-60 wt-% of a nonreactive organic thermoplastic nonether-containing condensation polymer, having a number average molecular weight of at least about 1,000, dissolved within the water-reactive liquid organometallic compound; wherein the polymer solution is stable at a temperature of about 0.degree.-100.degree. C. and is capable of curing upon exposure to water to form a composite material at a temperature of about 10.degree.-100.degree. C. ### Claim 20 (depends on 19) The water-curable polymer solution of claim 19 comprising greater than about 50 wt-% of the liquid organometallic compound. ### Claim 21 (depends on 19) The water-curable polymer solution of claim 19 wherein R.sup.1 is selected from the group consisting of C.sub.1 -C.sub.8 alkyl, a C.sub.5 -C.sub.8 cycloalkyl, a C.sub.6 -C.sub.10 aryl, C.sub.1 -C.sub.8 acyl, and a C.sub.3 -C.sub.6 ketoxime. ### Claim 22 (depends on 21) The water-curable polymer solution of claim 21 wherein R.sup.2 is selected from the group consisting of hydrogen, methyl, ethyl, phenyl, and vinyl. ### Claim 23 (depends on 19) The water-curable polymer solution of claim 19 further comprising an effective amount of a catalyst. ### Claim 24 (depends on 19) The water-curable polymer solution of claim 19 further comprising a toughening agent. ### Claim 25 A water-curable resin composition comprising: (a) a water-reactive liquid organometallic compound having at least one hydrolyzable group per molecule; and (b) a nonreactive organic thermoplastic addition polymer, having a number average molecular weight of at least about 1,000, mixed with the water-reactive liquid organometallic compound; wherein the resin composition is stable at a temperature of about 0.degree.-100.degree. C. and is capable of curing upon exposure to water to form a composite material at a temperature of about 10.degree.-100.degree. C.