Cross-linkable monomers and polymers and the use thereof
View Patent ↗The invention relates to novel cross-linkable monomers that may be polymerized with ethylenically unsaturated comonomers to form cross-linkable copolymers. Said copolymers may particularly be used in the form of aqueous dispersions as formaldehyde-free adhesives or as coatings with good water resistance. The cross-linkable monomer is a compound in acid or salt form comprising an anion of the formula (I) and one or more cations for producing electrical neutrality, where R 1 and R 2 represent, independently of one another, hydrogen alkyl, cycloalkyl, aryl, aralkyl, —COOR 5 , —COO − cat + or —CON(R 6 R 7 ), R 6 and R 7 represent, independently of one another, hydrogen, alkyl, or aryl, cat + represents a monovalent cation, and one of the groups R 1 or R 2 may also represent a group —X—R 4 —CR 5 (OH)SO 3 − ), wherein X, R 4 , and R 5 assume one of the meanings listed below, R 3 represents hydrogen, alkyl, or aryl, X is selected from the group of direct C—C bond, —O—, —CH 2 —O—, —CH 2 —NR 8 —, —COO— or —CONR 8 —, R 8 represents hydrogen, alkyl, or aryl, R 4 represents alkylene, polyoxyalkylene, cycloalkylene, or arylene, and R 5 represents hydrogen, alkyl, cycloalkyl, or aryl.
1. A compound in acid or salt form, which contains an anion of the formula (I) and one or more cations for producing electroneutrality
in which:
R 1 and R 2 , independently of one another, are hydrogen, alkyl, cycloalkyl, aryl, aralkyl, —COOR 5 , —COO − Cat + , —CON(R 6 R 7 ) or —X—R 4 —CR 5 (OH)(SO 3 − );
R 4 is alkylene, polyoxyalkylene, cycloalkylene or arylene;
R 5 is hydrogen, alkyl, cycloalkyl or aryl;
R 3 , R 6 and R 7 , independently of one another, are hydrogen, alkyl or aryl:
Cat + is a monovalent cation;
X is selected from the group consisting of —O—, —CH 2 —O—, —COO— or —CONR 8 —; and
R 8 is hydrogen, alkyl or aryl.
2. The compound as claimed in claim 1 , wherein R 1 and R 2 , independently of one another, are hydrogen, alkyl, —COOR 5 or —COO − Cat + , and wherein R 3 is hydrogen or alkyl.
3. The compound as claimed in claim 2 , wherein one of the radicals R 1 or R 2 is —COOR 5 or —COO − Cat + .
4. The compound as claimed in claim 3 , wherein R 1 and R 2 , independently of one another, are hydrogen, methyl, —COOR 5a or —COO − Cat+ and wherein at least one of the radicals R 1 or R 2 is —COOR 5a or —COO − Cat+, R 5a being hydrogen or C 1 -C 6 -alkyl, and wherein R 3 is hydrogen or methyl.
5. The compound as claimed in claim 1 , wherein one of the radicals R 1 or R 2 is an —X—R 4 —CR 5 (OH)(SO 3 − ) group.
6. The compound as claimed in claim 1 , wherein X is —COO—.
7. The compound as claimed in claim 1 , wherein R 4 is alkylene or polyoxyalkylene.
8. The compound as claimed in claim 7 , wherein R 4 is unsubstituted C 1 -C 6 -alkylene.
9. The compound as claimed in claim 8 , wherein R 4 is unsubstituted C 1 -C 4 -alkylene.
10. The compound as claimed in claim 1 , wherein R 5 is hydrogen or alkyl.
11. The compound as claimed in claim 1 , wherein the cations for producing electroneutrality are selected from the group consisting of hydrogen, ammonium, or mono- to tetravalent metal ions.
12. The compound as claimed in claim 1 , wherein the anion of formula (I) is an anion of the formula (IVa) or (IVb)
13. A compound in acid or salt form, which contains an anion of the formula (I) and one or more cations for producing electroneutrality
in which:
R 1 and R 2 , independently of one another, are hydrogen, alkyl, cycloalkyl, aryl, aralkyl, —COOR 5 , —COO − Cat + , —CON(R 6 R 7 ), or —X—R 4 —CR 5 (OH)(SO 3 − ), wherein at least one of the radicals R 1 or R 2 is —X—R 4 —CR 5 (OH)(SO 3 − );
R 4 is alkylene, polyoxyalkylene, cycloalkylene or arylene;
R 5 is hydrogen, alkyl, cycloalkyl or aryl;
R 3 , R 6 and R 7 , independently of one another, are hydrogen, alkyl or aryl;
Cat + is a monovalent cation;
X is selected from the group consisting of —O—, —CH 2 —O—, —CH 2 —NR 8 —, —COO— or —CONR 8 —; and
R 8 is hydrogen, alkyl or aryl.
14. A compound in acid or salt form, which contains an anion of the formula (IVa) or (IVb) and one or more cations for producing electroneutrality
in which:
R 4 is alkylene, polyoxyalkylene, cycloalkylene or arylene; and
R 5 is hydrogen, alkyl, cycloalkyl or aryl.