Curable material comprising silylated polymers containing urethane groups, and use thereof in sealants, adhesives, binders and/or surface modifiers

Patent metadata

Field	Value
Publication number	US-9441145-B2
Application number	US-201514624634-A
Country	US
Kind code	B2
Filing date	Feb 18, 2015
Priority date	Aug 19, 2009
Publication date	Sep 13, 2016
Grant date	Sep 13, 2016

Abstract

Curable material comprising silylated polymers containing urethane groups, and use thereof in sealants, adhesives, binders and/or surface modifiers.

First claim

The invention claimed is:

1. A curable material comprising:
urethane-group-containing reaction products, which is obtainable by reacting:
a) at least one compound containing one or more isocyanate groups with;
b) at least one compound bearing one or more alkoxysilyl groups and additionally bearing at least one hydroxyl group;
c) optionally in the presence of one or more catalysts;
d) optionally in the presence of further components reactive towards the reaction products; and
e) optionally in the presence of further compounds which are not reactive towards the reaction products and reactants;

wherein component (b) is one or more silyl polyethers 1 of the formula (2):

where:
a is an integer from 1 to 3;
b is an integer from 0 to 2, and the sum of a and b is 3;
c is an integer from 0 to 22;
d is an integer from 2 to 500;
e is an integer from 2 to 10,000;
f is an integer from 0 to 1,000;
g is an integer from 0 to 1,000;
h, i,and j independently of one another are integers from 0 to 500;
n is an integer between 2 and 8;
R independently at each occurrence represents a radical selected from linear or branched, saturated, alkyl radicals having 1 to 20 carbon atoms or haloalkyl groups having 1 to 20 carbon atoms;
R 1 is a hydroxyl group or a saturated linear, branched or cyclic oxyorganic radical having 1 to 1500 carbon atoms, that is optionally further substituted, wherein the chain is optionally interrupted by a heteroatom or a radical comprising an oxyaromatic system;
R 2 and R 3 are independently of one another, H, or a saturated or singly or multiply unsaturated monovalent hydrocarbon radical that is optionally further substituted;
R 5 and R 6 are independently of one another, H, or a saturated or singly or multiply unsaturated monovalent hydrocarbon radical that is optionally further substituted;
Y is absent;
R 4 independently at each occurrence is a linear or branched alkyl radical of 1 to 24 carbon atoms or an aromatic or cycloaliphatic radical, which optionally further comprises alkyl groups;
R 7 and R 8 are independently of one another either hydrogen or an alkyl, alkoxy, aryl or aralkyl group; and
R 9 , R 10 , R 11 , and R 12 are independently of one another either hydrogen or an alkyl, alkenyl, alkoxy, aryl or aralkyl group, wherein R 10 and R 11 are optionally bridged via the fragment Z, wherein Z is absent or is a divalent alkylene radical or alkenylene radical;
with the proviso that the fragments having the indices d, e, f and/or h are present with statistical distribution or blockwise sequencing.

2. The curable material according to claim 1 ;
wherein component (a) containing isocyanate groups bears no alkoxysilyl and/or alkylsilyl groups.

3. The curable material according to claim 1 ;
wherein, based on an individual molecule of the reaction product, there are on average more than one alkoxysilyl group per urethane group or reaction deriviative thereof.

4. The curable material according to claim 1 , further comprising:
compounds having at least one isocyanate, hydroxyl, amino, epoxy, or unsaturated C═C group, or reactive silanes.

5. The curable material according to claim 4 ;
wherein the reactive silanes are those of the formula (4);
U x SiV (4-x)   (4);

where:
U represents identical or different groups which are non-hydrolysable in the presence of water and catalytic amounts of Brønsted acid at temperatures of up to 100° C.;
V represents identical or different groups which are hydrolysable in the presence of water and catalytic amounts of Brønsted acid at temperatures up to 100° C., or hydroxyl groups; and
x is 1, 2, 3, or 4; and/or

wherein the silyl-functional compounds are those of the formula (5):

where:
X 1 , X 2 , and X 3 independently of one another are alkyl or alkoxy radicals having 1-8 C atoms;
A represents a carboxyl, carbamate, amide, carbonate, ureido, or sulphonate group containing radical, or denotes an oxygen atom;
w is an integer from 1 to 8; and
v is an integer from 1 to 20; and

wherein the polymer radical is selected from a group consisting of alkyd resins, oil-modified alkyd resins, saturated and unsaturated polyesters, natural oils, epoxides, polyamides, polycarbonates, polyethylenes, polypropylenes, polybutylenes, polystyrenes, ethylene-propylene copolymers, (meth)acrylates, (meth)acrylamides and salts thereof, phenolic resins, polyoxymethylene homopolymers and copolymers, polyurethanes, polysulphones, polysulphide rubbers, nitrocelluloses, vinyl butyrates, vinyl polymers, ethylcelluloses, cellulose acetates and butyrates, rayon, shellac, waxes, ethylene copolymers, organic rubbers, polysiloxanes, polyethersiloxanes, silicone resins, polyethers, polyether esters, and polyether carbonates.

6. The curable material according to claim 1 , further comprising
one or more blowing agents.

7. A method of improving the adhesive properties of a composition selected from the group consisting of curable compositions, adhesives, sealants, sealing compounds, binders, surface-coating materials, reactive crosslinkers, adhesion promoters, water repellents, wetting agents, primers and surface modifiers, architectural water repellents, additives in lacquer formulations, nail varnish formulations, reactive diluents, emulsions, wetting agents, paints, adhesion promoters, binders, plasticisizers, thixotropic agents, fungicides, flame retardants, pigments, fillers, functional additives in plastics, polymeric foams, organic resins or silicone resins, melt-flow-index improvers, slip additives for textiles or fibres, lubricants, matting agents, adsorbants and adsorbants, self-dispersible particles, particulate emulsifiers, defoamers, binders for ceramic compositions, architectural preservatives, encapsulants, sealing systems, antistatic additives, free-flow aids, microbicidal additives, fluorescent markers, effect pigments, matting agents, release agents, low-temperature-resistant cable coatings, conductive coatings, conductor tracks, antistatic coatings, electronic and electrical components, rubber parts and membranes, sizes in the textile and glass fibre industries, paper, additives for toners, abrasives and line fillers in cosmetics, formulating agents and carrier materials, dyes and preservatives, coatings, corrosion inhibitors, inks, varnishes, tribological, and haptic coatings, the method comprising:
adding the curable material of claim 1 to said composition.

8. A method of improving the adhesive properties on or for a macroscopic or microscopic substrate comprising a material selected from the group consisting of:
metals and metal oxides, glass and glass fibres/glass fabrics, wood, wood-based materials, natural fibres, cork, silicatic materials, concrete, mortar, plaster, masonry, particles, oxidic particles, fumed silica, precipitated silicas, quartz particles and other inorganic oxide particles, glass particles, titanium dioxide, aluminium oxide, zirconium dioxide, cerium dioxide, iron oxides, copper oxides, kaolin, wollastonite, talc, mica, feldspars, hydroxides, aluminium trihydroxide, magnesium dihydroxide, boehmite, hydrotalcite and hydroxydic iron pigments, FeO(OH), carbonates, calcium carbonate and dolomite, iron, copper, zinc, nickel, aluminium, magnesium, metal alloys and carbon-containing materials, graphite and carbon black, organic particulate substrates, silicone resins, organically modified silicones, organic polymers and biopolymers, leather, tissue, paper, and mixtures thereof, t

Assignees

• Evonik Degussa Gmbh

Inventors

• Schubert Frank
• Knott Wilfried
• Ferenz Michael
• Silber Stefan

Classifications

• C08J2375/08

  from polyethers · CPC title

• C09D175/08

  from polyethers · CPC title

• C08G65/22

  Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08G18/289

  containing silicon · CPC title