Compounds containing (meth)acrylate groups and sulfonate or sulfate groups, polymers and condensates made therefrom and use of the polymers and condensates

Patent metadata

Field	Value
Publication number	US-9353226-B2
Application number	US-201214122698-A
Country	US
Kind code	B2
Filing date	May 24, 2012
Priority date	May 27, 2011
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

The invention relates to a compound, comprising at least three functionalities, that is (a) a sulfonate or sulfate group of the formula —(O) d —SO 3 M with d=0 or 1 and M=hydrogen or a monovalent metal cation or the corresponding fraction of a polyvalent metal cation, (b) a (meth)acryl group, and (c) either (c1) at least one further (meth)acryl group or an inorganically condensable group, and/or (c2) a further carboxylic acid function, and/or (c3) a function which increases the refractive index of a material produced from the compounds, that is a thioether group, with the proviso that a sulfonate or sulfate group and a (meth)acrylate group are separated from one another in a silicon-free compound via a hydrocarbon-containing group, the carbon chain of which is either interrupted by O, S or NH or contains a linking group.

First claim

What is claimed is:

1. A compound comprising:
a first functionality (a) that is a sulfonate group or a sulfate group of the formula —(O) d —SO 3 M with d=0 or 1 and with M=hydrogen or a monovalent metal cation or a corresponding portion of a multivalent metal cation;
a second functionality (b) that is a (meth)acryl residue;
a third functionality (c1) that is an inorganically condensable silyl group; and
at least one fourth functionality selected from the group consisting of (c2) a carboxylic acid function and (c3) a function by which the refractive index of a material made from the compound is increased and that is a thioether group.

2. The compound according to claim 1 with the formula (II)

wherein
R 1 is a bivalent hydrocarbon residue which is optionally interrupted by one or more oxygen atoms, sulfur atoms, ester groups, amino groups or amide groups and which is bonded by a carbon atom to the silicon atom,
R 9 is H or alkyl or, in case of a=0 and g=1, a hydrolytically condensable residue or

R 3 is an alkylene that is unsubstituted or substituted with a functional group, straight-chain, branched or has at least one cyclic structure,
A is a linking group,
R 4 is a hydrocarbon group that is unsubstituted or substituted with a functional substituent and that is optionally interrupted by O, S, NH or NR 8 ,
M is hydrogen or a monovalent metal cation or the corresponding portion of a multivalent metal cation,
R 5 and R 6 , independently of each other, are either residues that are condensable under hydrolysis conditions or alkyl, aryl, arylalkyl, alkylaryl or alkylarylalkyl substituted or unsubstituted, straight-chain, branched or having at least one cyclic structure, or a corresponding alkenyl, arylalkenyl, or alkenylaryl,
R 8 is alkyl or alkenyl or a (meth)acryl residue,
B is vinyl, 2-allyl or, in case of e>1, an organic residue with e vinyl groups, wherein each one of the e vinyl groups is bonded to one of the e groups defined by the curly brackets,
Y is a nitrogen atom, —O—CH═, —S—CH═ or —NH—CH═, wherein in each case the oxygen atom, the sulfur atom or the NH group has a bond to the adjacent C(O) group,
a is 0 or 1,
b is 0 or 1,
c is 0 or 1,
d is 0 or 1,
e is 1, 2 or 3,
f is 1, and
g is 0 or 1.

3. The compound according to claim 2 , wherein at least one of the residues R 3 and R 4 is substituted with a residue R 10 COOM and optionally with at least one hydroxyl group and/or a residue SO 3 M, wherein R 10 is a chemical bond or a C 1 -C 6 alkylene residue.

4. The compound according to claim 2 , with the proviso that, when Y is a nitrogen atom, b=0 and c=0, the residue R 3 means unsubstituted or substituted ethylene, and, when Y is a nitrogen atom, b=0 and c=1, the residue R 4 is an alkylene that is unsubstituted or substituted with a functional substituent and that is interrupted by O, S, NH or NR 8 .

5. The compound according to claim 2 , wherein the linking group A in the formula (II) is selected from (read from the left to the right in the formula (II)) C(O)NH, NHC(O), NR 8 C(O), C(O)O, and OC(O), wherein R 8 is alkyl or alkenyl or a (meth)acryl residue.

6. The compound according to claim 1 that is a silane of the formula (I)
R 7 a R 2 b SiZ 4-a-b   (1)

wherein
R 7 is a hydrolytically condensable residue;
R 2 is an alkyl, aryl, arylalkyl, alkylaryl or alkylarylalkyl that is substituted or unsubstituted, straight-chain, branched or has a cyclic structure or is a corresponding alkenyl whose carbon chain in all cases optionally can be interrupted by —O—, —S—, —NH—, —S(O)—, —C(O)NH—, —NHC(O)—, —C(O)O—, —C(O)S, —NHC(O)NH—, or C(O)NHC(O) groups which can optionally be oriented in both possible directions;
Z is a residue in which are present at least one (meth)acryl group and either at least a sulfonate group or a sulfate group that are bonded directly or indirectly by an unsubstituted or substituted hydrocarbon group via an Si—C bond to the silicon atom, wherein Z contains the at least one fourth functionality;
a is 1, 2or 3;
b is 0, 1 or 2; and
a+b together are 2 or 3.

7. The compound according to claim 6 with the formula (Ia)

wherein
R 1 is a bivalent hydrocarbon group bonded by a carbon atom to the silicon atom, which is optionally interrupted by one or more oxygen atoms, sulfur atoms, ester groups, amino groups or amide groups,
R 7 is a hydrolytically condensable residue,
R 3 is an alkylene that is unsubstituted or substituted with a functional group, straight-chain, branched or has at least one cyclic structure,
R 4 is a hydrocarbon group that is unsubstituted or substituted with a functional substituent and that is optionally interrupted by O, S, NH or NR 8 ,
R 5 and R 6 , independently of each other, are either residues that are condensable under hydrolysis conditions or alkyl, aryl, arylalkyl, alkylaryl or alkylarylalkyl substituted or unsubstituted, straight-chain, branched or having at least one cyclic structure, or a corresponding alkenyl, arylalkenyl, or alkenylaryl,
B is vinyl, 2-allyl or, in case of e>1, an organic residue with e vinyl groups wherein each one of the e vinyl groups is bonded to one of the e groups defined by the curly brackets,
Y is a nitrogen atom, —O—CH═, —S—CH═ or —NH—CH═, wherein in each case the oxygen atom, the sulfur atom or the NH group has a bond to the adjacent C(O) group,
b is 0 or 1,
c is 0 or 1,
d is 0 or 1, and
e is 1, 2or 3.

8. The compound according to claim 7 , with the proviso that, when Y is a nitrogen atom, b=0 and c=0, the residue R 3 means optionally substituted ethylene, and, when Y is a nitrogen atom, b=0 and c=1, the residue R 4 is an alkylene that is unsubstituted or substituted with a functional substituent and that is interrupted by O, S, NH or NR 8 .

9. The compound according to claim 7 , wherein the linking group A in the formula (Ia) is selected from (read from the left to the right in the formula Ia) C(O)NH, NHC(O), NR 8 C(O), C(O)O, and OC(O), wherein R 8 is alkyl or alkenyl or a (meth)acryl residue.

10. The compound according to claim 7 , wherein at least one of the residues R 3 and R 4 is substituted with at least a residue R 10 COOM and optionally with at least one hydroxyl group and/or with a residue SO 3 M, wherein M is hydrogen or a monovalent metal cation or a corresponding portion of a multivalent metal cation, wherein R 10 is a chemical bond or a C 1 -C 6 alkylene residue.

11. A method for preparing a compound with the formula (II) as defined in claim 2 , the method comprising the steps of:
(a) Providing a hydrocarbon compound which carries at least two functional groups, selected from primary amines, secondary amines, hydroxyl groups and thiol groups;
(b) Reacting a first one of the two functional groups with optionally activated (meth)acrylic acid and reacting the second one of the two functional groups with a carboxylic acid that is optionally activated and has a C═C double bond, wherein said carboxylic acid can be (meth)acrylic acid or a different double bond-containing carboxylic acid; and
(c) Adding, subsequent to the step (b), a sulfonate group-containing compound or a sulfate group-contain

Assignees

• Wolter Herbert
• Seyfried Mona
• Nique Somchith
• Fraunhofer Ges Forschung

Inventors

• Wolter Herbert
• Seyfried Mona
• Nique Somchith

Classifications

• C08G77/18 Primary

  to alkoxy or aryloxy groups · CPC title

• C08G77/20

  containing silicon bound to unsaturated aliphatic groups · CPC title

• C08F30/08 Primary

  containing silicon · CPC title

• 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

• C08G77/28

  sulfur-containing groups · CPC title