Binding agent systems

Patent metadata

Field	Value
Publication number	US-9840635-B2
Application number	US-201415033768-A
Country	US
Kind code	B2
Filing date	Oct 23, 2014
Priority date	Nov 5, 2013
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

The invention relates to coatings which can be obtained by adding mercapto groups to acrylates and/or by a radiation curing process, said coatings having good properties, to methods for producing same, and to the use thereof.

First claim

The invention claimed is:

1. A coating composition comprising
at least one compound (S) having at least two α-(1′-hydroxyalkyl)acrylate groups,
optionally at least one compound (S1) having one α-(1′-hydroxyalkyl)acrylate group,
at least one compound (C) which carries at least two thiol groups,
optionally at least one reactive diluent (D) having a number-average molecular weight M n of less than 1000 g/mol and having at least two (meth)acrylate groups,
optionally at least one catalyst (E) which is able to accelerate the addition of thiol groups onto acrylate groups, and
optionally at least one photoinitiator (F).

2. The coating composition according to claim 1 , wherein compound (S) comprises at least one compound (S2) obtained by reaction of a polyfunctional acrylate (IV) with a monofunctional carbonyl compound (II) to form compound (V)

or by reaction of a monofunctional acrylate (I) with a carbonyl compound (VI) having a functionality of two or more to form compound (VII)

in which
R 1 , R 2 , and R 3 independently of one another are C 1 -C 18 -alkyl, C 2 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 6 -C 12 -aryl, C 5 -C 12 -cycloalkyl, or a five- to six-membered heterocycle with oxygen, nitrogen and/or sulfur atoms, wherein C 2 -C 18 -alkyl is optionally interrupted by one or more oxygen atoms and/or sulfur atoms and/or by one or more substituted or unsubstituted imino groups, wherein C 1 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 6 -C 12 -aryl, C 5 -C 12 -cycloalkyl are optionally substituted in each case by aryl, alkyl, aryloxy, alkyloxy, heteroatoms and/or heterocycles,
R 2 and/or R 3 additionally are hydrogen, C 1 -C 18 -alkoxy optionally substituted by aryl, alkyl, aryloxy, alkyloxy, heteroatoms and/or heterocycles, or —COOR 4 ,
R 2 may additionally, together with R 1 , form a ring, in which R 2 is a carbonyl group, wherein the group COOR 1 and R 2 together form an acid anhydride group —(CO)—O—(CO)—,
R 4 has the same definition as listed for R 1 , but may be different from R 1 ,
R 5 and R 6 independently of one another are hydrogen, C 1 -C 18 -alkyl, C 2 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 6 -C 12 -aryl, C 5 -C 12 -cycloalkyl, a five- to six-membered heterocycle with oxygen, nitrogen and/or sulfur atoms, or together form a ring, wherein C 2 -C 18 -alkyl is optionally interrupted by one or more oxygen atoms and/or sulfur atoms and/or by one or more substituted or unsubstituted imino groups, wherein C 1 -C 18 -alkyl, C 2 -C 18 -alkenyl, C 6 -C 12 -aryl, C 5 -C 12 -cycloalkyl are optionally substituted in each case by aryl, alkyl, aryloxy, alkyloxy, heteroatoms and/or heterocycles,
n is a positive integer from 2 to 10,
R 7 is an n-valent organic radical having 1 to 50 carbon atoms, which are unsubstituted or substituted by halogen, C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, carboxyl, carboxy-C 1 -C 8 -alkyl, C 1 -C 20 -acyl, C 1 -C 8 -alkoxy, C 6 -C 12 -aryl, hydroxyl or hydroxyl-substituted C 1 -C 8 -alkyl, and/or have one or more —(CO)—, —O(CO)O—, —(NH)(CO)O—, —O(CO)(NH)—, —O(CO)—, or —(CO)O— groups, and
R 8 is C 6 -C 12 -arylene, C 3 -C 12 -cycloalkylene, C 1 -C 20 -alkylene, C 2 -C 20 -alkylene, or a single bond, wherein R 8 is unsubstituted or substituted by halogen, C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, carboxyl, carboxy-C 1 -C 8 -alkyl, C 1 -C 20 -acyl, C 1 -C 8 -alkoxy, C 6 -C 12 -aryl, hydroxyl or hydroxyl-substituted C 1 -C 8 -alkyl, wherein C 2 -C 20 -alkylene is interrupted by one or more oxygen atoms and/or sulfur atoms and/or by one or more substituted or unsubstituted imino groups and/or by one or more —(CO)—, —O(CO)O—, —(NH)(CO)O—, —O(CO)(NH)—, —O(CO)—, or —(CO)O— groups.

3. The coating composition according to claim 2 , wherein compound (IV) is selected from the group consisting of ethylene glycol diacrylate, 1,2-propanediol diacrylate, 1,3-propanediol diacrylate, 1,4-butanediol diacrylate, 1,3-butanediol diacrylate, 1,5-pentanediol diacrylate, 1,6-hexanediol diacrylate, 1,8-octanediol diacrylate, neopentyl glycol diacrylate, 1,1-cyclohexanedimethanol diacrylate, 1,2-cyclohexanedimethanol diacrylate, 1,3-cyclohexanedimethanol diacrylate, 1,4-cyclohexanedimethanol diacrylate, 1,2-cyclohexanediol diacrylate, 1,3-cyclohexanediol diacrylate, 1,4-cyclohexanediol diacrylate, trimethylolpropane triacrylate, ditrimethylolpropane pentaacrylate, ditrimethylolpropane hexaacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, glycerol diacrylate, glycerol triacrylate, diacrylates of sugar alcohols, sorbitol, mannitol, diglycerol, threitol, erythritol, adonitol (ribitol), arabitol (lyxitol), xylitol, dulcitol (galactitol), maltitol, isomalt, polyester polyols, polyetherols, polyTHF having a molar mass of between 162 and 2000, poly-1,3-propanediol having a molar mass of between 134 and 1178, or polyethylene glycol having a molar mass of between 106 and 898, polyacrylates of sugar alcohols, sorbitol, mannitol, diglycerol, threitol, erythritol, adonitol (ribitol), arabitol (lyxitol), xylitol, dulcitol (galactitol), maltitol, isomalt, polyester polyols, polyetherols, polyTHF having a molar mass of between 162 and 2000, poly-1,3-propanediol having a molar mass of between 134 and 1178, or polyethylene glycol having a molar mass of between 106 and 898, urethane acrylates and polycarbonate acrylates.

4. The coating composition according to claim 2 , wherein compounds (II) and (VI) are aromatic aldehdyes.

5. The coating composition according to claim 1 , wherein compound (S) comprises at least one compound (Sz) obtainable by reaction of at least one difunctional carbonyl compound (A2) and/or at least one more-than-difunctional carbonyl compound (Ax) with at least one difunctional acrylate compound (B2) and/or at least one more-than-difunctional acrylate compound (By).

6. The coating composition according to claim 5 , wherein compound (S) comprises at least one compound (Sz) obtainable by reaction of at least one difunctional carbonyl compound (A2) with at least one difunctional acrylate compound (B2).

7. The coating composition according to claim 5 , wherein compound (A2) is selected from the group consisting of glyoxal, malonaldehyde, succinaldehyde, glutaraldehyde, capronaldehyde, furan-2,5-dialdehyde, pyrrole-2,5-dialdehyde, pyridine-2,6-dialdehyde, phthalaldehyde, isophthalaldehyde, and terephthalaldehyde.

8. The coating composition according to claim 5 , wherein compound (B2) is selected from the group consisting of ethylene glycol diacrylate, 1,2-propanediol diacrylate, 1,3-propanediol diacrylate, 1,4-butanediol diacrylate, and 1,6-hexanediol diacrylate.

9. The coating composition according to claim 5 , wherein compound (By) is selected from the group consisting of trimethylolpropane triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, triacrylate of singly to vigintuply ethoxylated trimethylolpropane, and tetraacrylate of singly to vigintuply ethoxylated pentaerythritol.

10. The coating composition according to claim 1 , wherein the compounds (C) are compounds (C1) of the formula

or compounds (C2) of the formula

or compounds (C3) of the formula

in which
Z 1 , Z 2 , Z 3

Assignees

• Construction Research & Technology Gmbh

Inventors

• Walther Burkhard
• Feichtenschlager Bernhard
• Woelfle Heimo
• Bruchmann Bernd
• Smeets Alfons

Classifications

• C09J4/00

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title

• C09D133/14 Primary

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title

• C09J133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08F220/38

  Esters containing sulfur · CPC title