Use of compounds having n 2-oxo-1,3-dioxolane-4-carboxamide units in two-component adhesives

Patent metadata

Field	Value
Publication number	US-11613681-B2
Application number	US-201716306174-A
Country	US
Kind code	B2
Filing date	May 29, 2017
Priority date	Jun 3, 2016
Publication date	Mar 28, 2023
Grant date	Mar 28, 2023

Abstract

A description is given of the use of compounds having n 2-oxo-1,3-dioxolane-4-carboxamide units as a reactive component in 2-component adhesives, especially for preparing hydroxypolyurethanes or hydroxypolycarbonates for adhesives applications, where n is a number greater than or equal to 2. A description is also given of corresponding two-component adhesives and adhesive bonding methods. Employed preferably as a second component of the two-component adhesive is a polyfunctional curing agent compound which is preferably selected from polyamines which have two or more amine groups and polyols which have two or more alcoholic hydroxyl groups.

First claim

What is claimed is:

1. A method for preparing a two-component adhesive, the method comprising:
introducing a compound having n 2-oxo-1,3-dioxolane-4-carboxamide units as a reactive component into the two-component adhesive, wherein the compound having n 2-oxo-1,3-dioxolane-4-carboxamide units is represented by formula (I)

where
R 1 and R 3 independently of one another are H or an organic radical; and
R 2 is an n-valent organic radical which is substituted by n−1 further 2-oxo-1,3-dioxolane-4-carboxamide groups
where n is a number greater than 2,
wherein the 2-oxo-1,3-dioxolane-4-carboxamide is a compound of formula (VII)

where

 is an alkoxylated glycerol radical having 2 to 5 C atoms in the alkoxy group,
introducing a polyfunctional curing agent compound into the two-component adhesive,
wherein the curing agent is selected from the group consisting of a polyamine which has two or more amine groups and a polyol which has two or more alcoholic hydroxyl groups.

2. The method according to claim 1 , wherein in the formula (I)
R 1 is H, and
R 3 is H.

3. The method according to claim 1 , wherein at least one of the compound having n 2-oxo-1,3-dioxolane-4-carboxamide units and the curing agent compound comprises at least one linear or branched spacer group having a molecular weight of at least 200 g/mol.

4. A two-component adhesive, comprising
at least one compound having n 2-oxo-1,3-dioxolane-4-carboxamide units as a reactive, first component;
wherein the compound having n 2-oxo-1,3-dioxolane-4-carboxamide units is represented by formula (I)

where
R 1 and R 3 independently of one another are H or an organic radical; and
R 2 is an n-valent organic radical which is substituted by n−1 further 2-oxo-1,3-dioxolane-4-carboxamide groups,
and
at least one curing agent compound selected from the group consisting of a polyamine having two or more amine groups and a polyol having two or more alcoholic hydroxyl groups as a second component;
wherein n is a number greater than 2,
where either the compound having n 2-oxo-1,3-dioxolane-4-carboxamide units or the curing agent compound or both comprises at least one linear or branched flexible spacer group, where the flexible spacer group has a molecular weight of at least 200 g/mol; wherein the 2-oxo-1,3-dioxolane-4-carboxamide is a compound of formula (VII)

where

 is an alkoxylated glycerol radical having 2 to 5 C atoms in the alkoxy group,
wherein the two-component adhesive has a bond strength of greater than 1.5 N/15 mm, measured as the peel strength of two polyester films bonded to one another with a 3 μm layer of adhesive and with an applied pressure of 3 bar after 24 hours.

5. The two-component adhesive according to claim 4 , which at a temperature of 70° C. or below has a Brookfield viscosity of less than 10 000 mPa s, measured at 12 rpm with spindle 3.

6. The two-component adhesive according to claim 4 , further comprising
at least one catalyst for catalyzing the reaction of cyclocarbonate groups with the functional groups of the curing agent.

7. A method for bonding two substrates to one another, the method comprising:
applying a two-component adhesive to a surface of at least one of the substrates,
wherein the method for bonding is a laminating method producing laminated articles selected from high-gloss films, composite films, and laminated moldings, where
a) a first substrate is provided in the form of a first film,
b) a second substrate is provided, selected from paper, a second film, which may be identical to or different from the first film, and moldings,
c) the two-component adhesive is applied to the first substrate and/or to the second substrate, and is optionally allowed to dry, and the first substrate is laminated onto the second substrate, wherein the lamination may optionally take place with thermal activation;
wherein the two component adhesive comprises at least one compound having n 2-oxo-1,3-dioxolane-4-carboxamide units as a reactive component, wherein the compound having n 2-oxo-1,3-dioxolane-4-carboxamide units is represented by formula (I)

where
R 1 and R 3 independently of one another are H or an organic radical; and
R 2 is an n-valent organic radical which is substituted by n−1 further 2-oxo-1,3-dioxolane-4-carboxamide groups,
and n is a number greater than 2,
wherein the 2-component lamination adhesive has a bond strength of greater than 1.5 N/15 mm, measured as the peel strength of two polyester films bonded to one another with a 3 μm layer of adhesive and with an applied pressure of 3 bar after 24 hours;
wherein a polyfunctional curing agent compound is used as a second component of the two-component adhesive and is selected from polyamines which have two or more amine groups and polyols which have two or more alcoholic hydroxyl groups;
wherein either the compound having n 2-oxo-1,3-dioxolane-4-carboxamide units or the curing agent compound or both comprise at least one linear or branched flexible spacer group, where the flexible spacer group has a molecular weight of at least 200 g/mol; wherein the 2-oxo-1,3-dioxolane-4-carboxamide is a compound of formula (VII)

where

 is an alkoxylated glycerol radical having 2 to 5 C atoms in the alkoxy group.

8. A film-laminated article, produced by the method according to claim 7 .

9. A 2-oxo-1,3-dioxolane-4-carboxamide of formula (1)

where
R 1 and R 3 independently of one another are H or an organic radical; and
R 2 is an n-valent organic radical which is substituted by n−1 further 2-oxo-1,3-dioxolane-4-carboxamide groups,
n is a number greater than 2, and
where between the 2-oxo-1,3-dioxolane-4-carboxamide groups there is at least one linear or branched spacer group having a molecular weight of at least 200 g/mol, wherein the 2-oxo-1,3-dioxolane-4-carboxamide is a compound of formula (VII)

where

 is an alkoxylated glycerol radical having 2 to 5 C atoms in the alkoxy group.

Assignees

• Basf Se

Inventors

• Schumacher Karl-Heinz
• Fenlon Thomas
• Putzien Sophie
• Vautravers Nicolas
• Licht Ulrike

Classifications

• C08G18/4841

  containing oxyethylene end groups · CPC title

• C08G18/7621

  being toluene diisocyanate including isomer mixtures · CPC title

• C09J175/04 Primary

  Polyurethanes · CPC title

• C08G71/04

  Polyurethanes · CPC title

• C09J5/06

  involving heating of the applied adhesive · CPC title