Liquid-applied waterproofing membrane for roofs comprising a trialdimine

Patent metadata

Field	Value
Publication number	US-9752054-B2
Application number	US-201414760878-A
Country	US
Kind code	B2
Filing date	Jan 21, 2014
Priority date	Jan 22, 2013
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

The present invention describes a one-part moisture-curing liquid-applied waterproofing membrane including a polyurethane polymer and both a trialdimine and a dialdimine as blocked amine hardeners in a specific ratio range. The membrane has a low odor, a long shelf life stability, a low viscosity at low solvent content, a sufficiently long open time to allow hand application and cures fast to a solid elastic material. The liquid-applied waterproofing membrane can be suitable for roofing applications, possessing high strength, high elongation and good durability under outdoor weathering conditions in a broad temperature range.

First claim

The invention claimed is:

1. A one-part moisture-curing liquid-applied waterproofing membrane comprising:
at least one isocyanate-functional polyurethane polymer;
at least one trialdimine of the formula (I),

 wherein
A is a trivalent hydrocarbyl moiety of molecular weight in the range of 380 to 5000 g/mol containing ether groups,
R 1 and R 2 are the same or different C 1 to C 12 linear or branched alkyls, or are joined together to form a divalent linear or branched C 4 to C 12 hydrocarbyl moiety which is part of a 5- to 8-membered carbocyclic ring,
R 3 is hydrogen or a linear or branched C 1 to C 12 alkyl or arylalkyl or alkoxycarbonyl, and
R 4 and R 5 are the same or different linear or branched C 1 to C 20 alkyl or cycloalkyl or aralkyl optionally containing ether groups, or are joined together to form a divalent linear or branched C 4 to C 12 hydrocarbyl moiety which is part of a 5- to 8-membered heterocyclic ring which, besides the nitrogen atom, may contain an ether or thioether or tertiary amino group; and

at least one dialdimine;

wherein the ratio between the number of the aldimino groups of the trialdimine and the number of aldimino groups of the dialdimine is in the range of 90/10 to 40/60.

2. The membrane according to claim 1 , wherein the isocyanate-functional polymer is based on an aliphatic polyisocyanate.

3. The membrane according to claim 1 , wherein the trialdimine of the formula (I) is N,N′,N″-tris(2,2-dimethyl-3-(N-morpholino)-propylidene)-polyoxypropylene triamine with an average molecular weight in the range of 860 to 5500 g/mol.

4. The membrane according to claim 1 , wherein the dialdimine is a dialdimine of the formula (II),

wherein
G is a divalent hydrocarbyl moiety of molecular weight in the range of 28 to 400 g/mol,
and R 1 , R 2 , R 3 , R 4 and R 5 are the same as in the formula (I).

5. The membrane according to claim 4 , wherein the dialdimine of the formula (II) is selected from the group consisting of N,N′-bis(2,2-dimethyl-3-(N-morpholino)-propylidene)-hexamethylene-1,6-diamine and N,N′-bis(2,2-dimethyl-3-(N-morpholino)-propylidene)-3-aminomethyl-3,5,5-trimethylcyclohexylamine.

6. The membrane according to claim 1 , wherein the dialdimine is a dialdimine of the formula (III),

wherein
G is a divalent hydrocarbyl moiety of a molecular weight in the range of 28 to 400 g/mol,
R 6 is a monovalent C 6 to C 20 hydrocarbyl moiety optionally containing ether, carbonyl or ester groups,
and R 1 , R 2 and R 3 are the same as in the formula (I).

7. The membrane according to claim 1 further comprising:
at least one ingredient selected from the group consisting of inorganic fillers and pigments,
at least one ingredient selected from the group consisting of flame-retarding plasticizers and flame-retarding fillers, and
at least one ingredient selected from the group consisting of catalysts, plasticizers, solvents and UV-stabilizers.

8. The membrane according to claim 1 containing
from 15 to 70 weight-% isocyanate-functional polyurethane polymers;
from 20 to 80 weight-% of fillers including inorganic fillers, flame-retarding fillers and pigments;
from 5 to 30 weight-% of plasticizers including flame-retarding plasticizers; and
at least one further ingredient selected from the group consisting of catalysts, solvents and UV-stabilizers.

9. The membrane according to claim 1 having a Brookfield viscosity in the range of 2000 to 15000 mPa·s at 20° C.

10. The membrane according to claim 1 containing 50 g VOC per liter or less.

11. A method for forming the membrane according to claim 1 , the method comprising applying a composition in liquid state onto a substrate of a roof structure in a layer thickness in the range of 0.5 to 3 mm, and curing the composition to form the membrane according to claim 1 .

12. Waterproofing system, consisting of:
optionally a primer and/or an undercoat,
one or more than one layer of the membrane according to claim 1 , and
optionally a top coat.

13. The waterproofing system according to claim 12 , wherein the one or more than one layer of the membrane according to claim 1 is in combination with a fibre reinforcement mesh.

14. Method of waterproofing a roof structure, comprising:
applying a composition in liquid state onto a substrate of the roof structure in a layer thickness in the range of 0.5 to 3 mm,
wherein the applying of the composition results in forming the membrane according to claim 1 ;
contacting the membrane with a fibre reinforcement mesh within the open time of the membrane;
exposing the membrane to moisture to thereby cure the membrane partially or fully to obtain an elastic coating,
optionally applying a second layer of the membrane in a layer thickness in the range of 0.5 to 3 mm and curing it by exposure to moisture.

15. Waterproof roof structure, obtained by the method according to claim 14 .

16. A one-part moisture-curing liquid-applied waterproofing membrane comprising:
at least one isocyanate-functional polyurethane polymer;
at least one trialdimine of the formula (I),

 wherein
A is a trivalent hydrocarbyl moiety of molecular weight in the range of 380 to 5000 g/mol containing ether groups,
R 1 and R 2 are the same or different C 1 to C 12 linear or branched alkyls, or are joined together to form a divalent linear or branched C 4 to C 12 hydrocarbyl moiety which is part of a 5- to 8-membered carbocyclic ring,
R 3 is hydrogen or a linear or branched C 1 to C 12 alkyl or arylalkyl or alkoxycarbonyl, and
R 4 and R 5 are the same or different linear or branched C 1 to C 20 alkyl or cycloalkyl or aralkyl optionally containing ether groups, or are joined together to form a divalent linear or branched C 4 to C 12 hydrocarbyl moiety which is part of a 5- to 8-membered heterocyclic ring which, besides the nitrogen atom, may contain an ether or thioether or tertiary amino group; and

at least one dialdimine;
wherein the ratio between the number of the aldimino groups of the trialdimine and the number of aldimino groups of the dialdimine is in the range of 90/10 to 40/60,
wherein the at least one trialdimine of the formula (I) increases the cure speed of the one-part moisture-curing liquid-applied waterproofing membrane.

Assignees

• Sika Tech Ag

Inventors

• Byrne Michael
• Gatrell Mark
• Coward Alexander
• Burckhardt Urs

Classifications

• C08G18/755 Primary

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C08G18/12 Primary

  using two or more compounds having active hydrogen in the first polymerisation step · CPC title

• C08G18/3256

  Reaction products of polyamines with aldehydes or ketones · CPC title

• C08G18/792

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

• C09D175/04 Primary

  Polyurethanes · CPC title