Special imines and their starting materials, and their use in the hardening of reactive resins by polyaddition or free-radical polymerisation

Patent metadata

Field	Value
Publication number	US-2023323008-A1
Application number	US-202118012950-A
Country	US
Kind code	A1
Filing date	Jun 14, 2021
Priority date	Jul 2, 2020
Publication date	Oct 12, 2023
Grant date	—

Abstract

Imine, obtainable by reaction of (i) an amino-functionalised polyoxyalkylene, the polyoxyalkylene chains of which are a copolymer of oxyethylene and oxypropylene units, those polyoxyalkylene chains carrying primary amino groups (preferably two terminal primary amino groups per molecule), and (ii) a ketone and/or aldehyde having a hydrogen atom at the carbon atom in the alpha-position to the carbonyl carbon; and various subjects of the invention based thereon, especially in coating systems or adhesive systems.

First claim

1 . An imine, obtainable by reaction of (i) an amino-functionalised polyoxyalkylene, the polyoxyalkylene chains of which are a copolymer of oxyethylene and oxypropylene units, those polyoxyalkylene chains carrying alkoxy groups having primary amino groups, and (ii) a ketone and/or aldehyde having a hydrogen atom at the carbon atom in the alpha-position to the carbonyl group.

2 . The imine according to claim 1 , which is obtainable by reaction of the amino-functionalised polyoxyalkylene (i), which carries a primary amino group in each case bonded to the terminal oxyalkylene group, with an alkanaldehyde (ii) having a hydrogen atom at the carbon atom in the alpha-position to the carbonyl group.

3 . The imine according to claim 1 , obtainable by reaction of the amino-functionalised polyoxyalkylene (i) with isobutyraldehyde (ii).

4 . The imine according to claim 1 , wherein the amino-functionalised polyoxyalkylene (i) carries two 2-aminopropyloxy groups which are terminal in each case.

5 . The imine according to claim 1 , wherein the amino-functionalised polyoxyalkylene (i) has the following formula:
wherein I and n each independently of the other denote, on average, from 1 to 10,; and m denotes from 1 to 50.

6 . The imine according to claim 5 , in wherein in the formula, on average, l and n denote approximately 3.6 and, on average, m denotes approximately 9.

7 . The imine according to claim 1 , wherein it has an average molecular weight of 2000 g/mol or less.

8 . The imine according to claim 1 in admixture with its starting materials (i) amino-functional polyoxyalkylene and (ii) ketone and/or, aldehyde.

9 . A mixture of (i) an amino-functional polyoxyalkylene and (ii) an aldehyde (preferred) and/or ketone, in each case as defined in claim 1 .

10 . A mixture according to claim 9 as constituent of a coating system or adhesive system or adhesive.

11 . A hardener as initiator for a free-radical-hardening system and/or for compounds that are hardenable by polyaddition, which
in the case of the free-radical-hardenable compounds (Case A) includes the following initiator system:
(a) at least one activator in the form of a metal salt and as free-radical starter
(b1) an amino-functional polyoxyalkylene (i) as defined in one of the above embodiments in admixture with an aldehyde (preferred) and/or ketone (ii) as defined in one of the above embodiments; or
(b2) an imine as defined in claim 1 ,
or a mixture of constituents (b1) and (b2); or
in the case of the compounds that are hardenable by polyaddition (Case B) represents the following constituent:
(b2) an imine as defined in claim 1 .

12 . A coating system or, adhesive system, including a hardener according to claim 11 and, as reactive resin, either (Aa) a free-radical-polymerisable reactive resin (Case A) or a reactive resin that includes epoxy groups (Ba1) or isocyanate groups (Ba2) (Case B), or a mixture of (Aa) and (Ba).

13 . A coating system or, adhesive system according to claim 12 , wherein the reactive resin is a free-radical-hardenable reactive resin according to (Aa), of the formula
in which a and b each independently of the other denote a number greater than or equal to 0, with the proviso that at least one of the values is greater than 0.

14 . A coating system or adhesive system according to claim 12 , Case B, wherein the reactive resin is a reactive resin that includes isocyanate groups in accordance with (Ba2), and particularly a prepolymer that includes at least two isocyanate groups.

15 . A coating system or adhesive system according to claim 12 in the form of a multi-component system, which includes a reactive resin according to (Aa) or (Ba) in one component and the hardener according to claim 12 in another component.

16 . A coatiing system or, adhesive system according to claim 14 in the form of a single-component system, and particularly in the form of a surface-coating that cures by polyaddition or in the form of an adhesive that cures by polyaddition.

17 . A method of usinng an adhesive system according to claim 12 (a) for adhesively bonding articles to one another or (b) for adhesively bonding an article to a fixed substrate.

18 . A method of using an adhesive system according to claim 17 , Case (b), wherein
an article is to be understood as being an accessory for a swimming pool, bedroom, bathroom or kitchen or an adapter element for holding such an accessory; a plate or a block, preferably made of metal, glass, plastics, concrete or stone; fibres, especially high-modulus fibres, preferably carbon fibres, especially for reinforcing built structures, for example walls, pillars or ceilings or floors; a structural element, such as a panel, a disc, or a block, for example made of stone, glass or plastics; or - in each case implemented in planar form as a mat and as loose material or as composite fabric or material - a non-woven, a woven fabric, a knitted fabric, a planar material obtained by knitting, a material obtained by tufting, preferably in each case with high-modulus fibres, for example made of glass fibres, carbon fibres and/or synthetic fibres, in the case of a composite material having a synthetic matrix; and a substrate is to be understood as being a building substrate, especially a wall, a ceiling or a floor in the construction field, preferably made of masonry, concrete, unglazed or glazed ceramics, or furthermore made of glass, wood, metal or plastics.

19 . A method of using an adhesive system according to claim 18 for adhesively bonding an anchoring element in a hole or a recess in the substrate.

20 . A method of using a coating system according to claim 12 for coating a substrate, the substrate.

21 . A method for coating a substrate with a coating system according to claim 12 , wherein the coating system is applied, if necessary with or after mixing of components thereof that do not cure on their own, and cured, with polymerisation taking place.

22 . A method
(a) for adhesively bonding articles to one another or (b) for adhesively bonding an article to a fixed substrate, wherein an adhesive system according to claim 12 is applied, if necessary with or after mixing of components thereof that otherwise do not react with one another, to one or more areas to be adhesively bonded of one or more of the articles to be adhesively bonded, and areas to be adhesively bonded are brought into contact with one another and the adhesive system is cured, with polymerisation taking place.

Assignees

• Fischerwerke Gmbh & Co Kg

Inventors

• Weinelt Christian
• Vogel Martin

Classifications

• C08G18/3256 Primary

  Reaction products of polyamines with aldehydes or ketones · CPC title

• C07C251/08

  being acyclic · CPC title

• C08G18/10

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• C09D175/02

  Polyureas · CPC title

• C09J175/02

  Polyureas · CPC title