Amino photo-reactive binder

Patent metadata

Field	Value
Publication number	US-10000446-B2
Application number	US-201214361433-A
Country	US
Kind code	B2
Filing date	Dec 18, 2012
Priority date	Jan 20, 2012
Publication date	Jun 19, 2018
Grant date	Jun 19, 2018

Abstract

A compound obtained by reaction of one or more amines of the general formula NHR 6 R 7 with a compound of the following general formula (IX):

wherein,
PI is a photoinitiator derivative, G is linker comprising a number p′ of unreacted hydroxyl groups, M is a group comprising a number z of (meth)acrylate groups equal to at least one, as well as inks, coating compositions and adhesives comprising the same.

First claim

The invention claimed is:

1. A compound having the formula,

wherein:
PI is a thioxanthone derivative, a benzophenone derivative, an anthraquinone derivative, or a 1,2-diketone derivative,
M is a group comprising a number z of (meth)acrylate groups equal to at least one,
Q is a linker,
G is a linker comprising a number p of unreacted hydroxyl groups comprised between 0 and 9, the linker being a residue of a polyhydroxy compound having at least 4 and at most 12 hydroxyl groups,
R 1 and R 2 either:
together with the N to which they are attached form a 5-6 membered saturated or aromatic ring optionally fused with a phenyl, said 5-6 membered ring containing one or more carbon atoms, from one to three nitrogen atoms and up to one oxygen atom, or
are independently selected from the group consisting of:
H,
C 1-30 alkyl,
C 2-30 alkenyl, and
5-6 membered saturated or aromatic ring containing one or more carbon atoms, up to three nitrogen atoms and up to two oxygen atoms, said ring being optionally substituted by a C 1-30 alkyl or by a C 1-30 alkyloxy or by a hydroxyl or by a C 1-6 alkyl substituted acyloxy,
or being optionally fused with a phenyl,
wherein each of said C 1-30 alkyl and C 2-30 alkenyl are independently optionally substituted with one or more substituents independently selected from the group consisting of:
a 5-6 membered saturated or aromatic ring containing one or more carbon atoms, up to three nitrogen atoms and up to two oxygen atoms,
a hydroxyl group,
a C 1-10 alkoxy group, and
an amine of formula —NR 3 R 4 , wherein R 3 and R 4 are independently selected from the group consisting of H and C 1-8 alkyl, and

n is from 1 to 10,
m is from 1 to 10, and
x is from 1 to 10,

with the proviso that if R 1 is a hydrogen atom, then the carbon atom in R 2 directly attached to the nitrogen must be attached to at least two carbon atoms.

2. The compound according to claim 1 wherein G is a residue of a polyhydroxy compound selected from the group consisting of polyhydroxy derivatives of aliphatic or aromatic polyethers, polyhydroxy derivatives of polyesters, polyhydroxy derivatives of polyamides, polyhydroxy derivatives of polyimides, polyhydroxy derivatives of polycarbonates, styrene allyl alcohols copolymers, di-trimethylolpropane, pentaerytritol, dipentaerytritol, C 1-3 alkoxylated derivatives thereof and mixtures thereof.

3. The compound according to claim 1 , wherein PI is selected from the group consisting of:

wherein “*” indicates the point of attachment of PI in the compound, wherein R′ is selected from the group consisting of H and phenyl, and wherein the phenyl is optionally substituted with a group R′″,
wherein R, R″ and R′″ are selected from the list group consisting of H, C 1-8 alkyl, C 1-10 alkoxy and halogen,
wherein E is selected from the group consisting of a single bond, a group of formula —O—Y—, and a group of formula -w-O(CO)-J-,
wherein Y and J are selected from the group consisting of C 1-3 alkylene and C 1-3 alkoxy C 1-3 alkylene, and wherein w is a C 1-3 alkylene.

4. The compound according to claim 3 wherein PI is selected from the list consisting of

5. The compound according to claim 4 having the formula

6. The compound of claim 5 wherein: Q is —C(O)—(CH2) 2 —.

7. A compound obtained by reaction of one or more amines of the formula NHR 6 R 7 with a compound of the following formula (IX)

wherein:
PI is a thioxanthone derivative, a benzophenone derivative, an anthraquinone derivative, or a 1,2-diketone derivative,
R 6 and R 7 either:
together with the N to which they are attached form a 5-6 membered saturated or aromatic ring optionally fused with a phenyl, said 5-6 membered ring containing one or more carbon atoms, from one to three nitrogen atoms and up to one oxygen atom, or
are independently selected from the group consisting of:
H,
C 1-30 alkyl,
C 2-30 alkenyl, and
5-6 membered saturated or aromatic ring containing one or more carbon atoms, up to three nitrogen atoms and up to one oxygen atom, said ring being optionally substituted by a C 1-30 alkyl or by a C 1-30 alkyloxy or by a hydroxyl or by a C 1-6 acyloxy, or being optionally fused with a phenyl,

wherein each of said C 1-30 alkyl and C 2-30 alkenyl are independently optionally substituted with one or more substituents independently selected from the group consisting of:
a 5-6 membered saturated or aromatic ring containing one or more carbon atoms, up to three nitrogen atoms and up to one oxygen atom,
a hydroxyl group,
a C 1-10 alkoxy group, and
an amine of formula —NR 3 R 4 , wherein R 3 and R 4 are independently selected from the group consisting of H and C 1-8 alkyl,

M is a group comprising a number z of (meth)acrylate groups equal to at least one,
G is linker comprising a number p′ of unreacted reactive hydroxyl groups, the linker being a residue of a polyhydroxy compound having at least 4 and at most 12 hydroxyl groups,
A is either H or CH 3 ,
n′ is from 1 to 11,
m is from 1 to 11, and
p′ is from 0 to 10;
with the proviso that n′ is at least 2 when M comprises only one (meth)acrylate group.

8. The compound according to claim 7 wherein the amine NHR 6 R 7 is selected from the list consisting of methylamine, ethylamine, propylamine, n-butylamine, sec-butylamine, pentylamine, hexylamine, 2-ethylhexylamine, cyclohexylamine, octylamine, tert-octylamine, 3-morpholinopropylamine, dodecylamine, fatty amines, ethoxylated fatty amines, monoethanolamine, aniline, N-alkyl aniline, 4-aminophenol, Ethyl-4-aminobenzoate, dicocoamine, diethylamine, diethanolamine, dipropylamine, dibutylamine, 2-(methylamino)ethanol, 2-methoxyethylamine, bis(2-hydroxypropylamine), dihexylamine, diisopropylamine, 1-methylpiperazine, 4-methylpiperidine, morpholine, piperidine, Bis(2-ethylhexyl)amine, 2-hydroxypropylamine, N-benzylmethylamine, Dipentylamine, 1,2,3,4-tetrahydroisoquinoline, dicyclohexylamine and dioctylamine.

9. The compound of claim 8 wherein M is the residue of (meth)acrylic acid.

10. An ink, a coating composition or an adhesive comprising the compound according to claim 9 .

11. A substrate on which the ink, coating composition or adhesive of claim 10 has been applied.

12. The substrate according to claim 11 being a food packaging printed with the ink.

Assignees

• ALLNEX Belgium SA

Inventors

• Gevaert Paul
• Cappelle Steven
• Van Den Bergen Hugues
• Gupta Ram

Classifications

• C07C227/16

  by reactions not involving the amino or carboxyl groups · CPC title

• C09D133/14

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

• C07C229/38 Primary

  having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton · CPC title

• C07C229/12 Primary

  to carbon atoms of acyclic carbon skeletons · CPC title

• Y10T428/24802

  Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.] · CPC title