Liquid-applied waterproofing membrane for roofs comprising two different aldimines

Patent metadata

Field	Value
Publication number	US-9879154-B2
Application number	US-201414762379-A
Country	US
Kind code	B2
Filing date	Jan 21, 2014
Priority date	Jan 22, 2013
Publication date	Jan 30, 2018
Grant date	Jan 30, 2018

Abstract

A one-part moisture-curing liquid-applied waterproofing membrane is disclosed as including a polyurethane polymer and two different aldimines 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 is particularly 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 aldimine of the formula (I); and
at least one aldimine of the formula (II),

wherein
A 1 is an m-valent hydrocarbyl moiety of molecular weight in a range of 28 to 5,000 g/mol optionally containing ether or urethane groups,
A 2 is an n-valent hydrocarbyl moiety of molecular weight in a range of 28 to 5,000 g/mol optionally containing ether or urethane 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,
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,
R 6 is a monovalent C 6 to C 20 hydrocarbyl moiety optionally containing ether, carbonyl or ester groups, and
m and n are from 2 to 6;
wherein the ratio between the number of the aldimino groups of the aldimine of the formula (I) and the aldimine of the formula (II) is in a range of 90/10 to 50/50,
wherein the molecular weight refers to the molar mass (given in grams per mole) of a molecule or a part of a molecule and, for an oligomeric or polymeric mixture of molecules or moieties, to the number-average molecular weight (Mn).

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
A 1 is a divalent or a trivalent hydrocarbyl moiety of molecular weight in a range of 180 to 5,000 g/mol containing ether groups; and
A 2 is a divalent hydrocarbyl moiety of molecular weight in a range of 28 to 400 g/mol.

4. The membrane according to claim 3 , wherein
the aldimine of the formula (I) is selected from the group consisting of: N,N′-bis(2,2-dimethyl-3-(N-morpholino)-propylidene)-polyoxypropylene diamine with an average molecular weight in a range of 500 to 4,400 g/mol and N,N′,N″-tris(2,2-dimethyl-3-(N-morpholino)-propylidene)-polyoxypropylene triamine with an average molecular weight in a range of 860 to 5,500 g/mol; and
the aldimine of the formula (II) is selected from the group consisting of: N,N′-bis(2,2-dimethyl-3-lauroyloxypropylidene)-hexamethylene-1,6-diamine and N,N′-bis(2,2-dimethyl-3-lauroyloxypropylidene)-3-aminomethyl-3,5,5-trimethylcyclohexylamine.

5. The membrane according to claim 1 , wherein:
A 1 is a divalent hydrocarbyl moiety of molecular weight in a range of 28 to 400 g/mol; and
A 2 is a divalent or a trivalent hydrocarbyl moiety of molecular weight in a range of 180 to 5,000 g/mol containing ether groups.

6. The membrane according to claim 5 , wherein:
the aldimine of the formula (I) 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; and
the aldimine of the formula (II) is selected from the group consisting of: N,N′-bis(2,2-dimethyl-3-lauroyloxypropylidene)-polyoxypropylene diamine with an average molecular weight in a range of 700 to 4,600 g/mol and N,N′,N″-tris(2,2-dimethyl-3-lauroyloxypropylidene)-polyoxypropylene triamine with an average molecular weight in a range of 1200 to 5,800 g/mol.

7. The membrane according to claim 1 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 comprising:
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 a range of 2,000 to 15,000 mPa·s at 20° C.

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

11. The membrane according to claim 1 , in combination with a roof.

12. A 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. A method of waterproofing a roof structure having a one-part moisture-curing liquid-applied waterproofing membrane including:
at least one isocyanate-functional polyurethane polymer;
at least one aldimine of the formula (I); and
at least one aldimine of the formula (II),

wherein
A 1 is an m-valent hydrocarbyl moiety of molecular weight in a range of 28 to 5,000 g/mol optionally containing ether or urethane groups,
A 2 is an n-valent hydrocarbyl moiety of molecular weight in a range of 28 to 5,000 g/mol optionally containing ether or urethane 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,
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,
R 6 is a monovalent C 6 to C 20 hydrocarbyl moiety optionally containing ether, carbonyl or ester groups, and
m and n are from 2 to 6;
wherein the ratio between the number of the aldimino groups of the aldimine of the formula (I) and the aldimine of the formula (II) is in a range of 90/10 to 50/50,
wherein the molecular weight refers to the molar mass (given in grams per mole) of a molecule or a part of a molecule and, for an oligomeric or polymeric mixture of molecules or moieties, to the number-average molecular weight (Mn),
the method comprising:
applying the membrane in liquid state onto a substrate of the roof structure in a layer thickness in a range of 0.5 to 3 mm;
contacting the membrane with a fibre reinforcement mesh within an open time of the membrane;
exposing the membrane to moisture to thereby cure the membrane partially or fully to obtain an elastic coating; and
optionally applying a second layer of the membrane in a layer thickness in a range of 0.5 to 3 mm and curing it by exposure to moisture.

14. A waterproof roof structure, obtained by the method according to

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

• C08G2190/00

  Compositions for sealing or packing joints · CPC title

• C09D175/12

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title

• C08G18/3256

  Reaction products of polyamines with aldehydes or ketones · CPC title

• C08G18/307

  Atmospheric humidity · CPC title