IP Library Granted Patent US 7,479,526
Granted Patent B2
US 7,479,526 · App. 10/565,028 · Granted Jan 20, 2009

Hydroxy-functional binder components

Assignee: Cytec Surface Specialties Austria GmbH
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Quick Facts
Patent No.
US 7,479,526
App. No.
10/565,028
Granted
Jan 20, 2009
Kind
B2
Abstract

The invention relates to hydroxyl-functional binder components ABC containing a linear or branched main chain having a polymethylene structure —(CH 2 ) n — or a polyester structure or a structure derived from the fatty acid esters of glycerin or other polyvalent alcohols. The invention is characterized in that said components have grafted cyclic imide structures on the main chain, wherein the imide-nitrogen atom is substituted by a hydroxyalkyl group or a hydroxyalkyl-aryl group. The invention also relates to method for the production of said components by reacting oleofinically unsaturated acid anhydrides B and hydroxyamines C and to the utilization of the inventive components for the formulation of binders.

Claims (31)

1. Reaction products of

hydroxy-functional binder components containing a linear or branched main chain which has a polymethylene structure —(CH 2 ) n — or a polyester structure or a structure derived from fatty acid esters of glycerol or other polyhydric alcohols, characterised in that they have cyclic imide structures grafted on to the main chain, the imide nitrogen atom carrying a hydroxyalkyl group or a hydroxyalkyl-aryl group as substituent, and

compounds selected from the group consisting of

compounds D′ containing acid groups, wherein the reaction is an esterification reaction, and wherein water is removed, and wherein the reaction products contain at least one acid group per molecule, and of

compounds D″ selected from the group consisting of compounds having at least one isocyanate group and one acid group, and of compounds having at least one isocyanate group and at least one olefinically unsaturated group, wherein the reaction is an addition reaction, and wherein the reaction products have a urethane, an urea, or a thiourea structure, and wherein the reaction products contain, per molecule, at least one acid group, or at least one olefinically unsaturated group.

2. The reaction products of claim 1 wherein the hydroxy-functional binder components are obtained by reaction of olefinically unsaturated substances A having at least one olefinic double bond and a molar mass of from 400 g/mol to 6,000 g/mol, olefinically unsaturated cyclic acid anhydrides B and hydroxyamines C having at least one primary amino group and at least one hydroxyl group, wherein the radicals of the acid anhydrides B are bonded to the compounds A by a carbon-carbon bond, and wherein the acid anhydride groups are converted into acid imide groups by reaction with the hydroxyamines C.

3. The reaction products of claim 2 , wherein the olefinically unsaturated substances A are selected from the group consisting of oils, partially saponified or partially transesterified oils, low molar mass alkyd resins and oligomers or polymers of diolefins.

4. The reaction products of claim 2 , wherein the olefinically unsaturated cyclic acid anhydrides B are intramolecular anhydrides of aliphatic and cycloaliphatic dicarboxylic acids having 4 to 16 carbon atoms and contain at least one olefinic double bond.

5. The reaction products of claim 2 wherein the hydroxyamines C are aromatic-aliphatic or aliphatic linear, branched or cyclic hydroxyamines having at least one hydroxyl groups and at least one primary amino group and at least two carbon atoms.

6. A process for the preparation of reaction products of hydroxy-functional binder components as claimed in claim 2 , characterised in that

olefinically unsaturated substances A having at least one olefinic double bond and a molar mass of from 400 g/mol to 6,000 g/mol are reacted with

olefinically unsaturated cyclic acid anhydrides B to give an adduct linked via carbon-carbon bonds, which is reacted with

hydroxyamines C having at least one primary amino group and at least one hydroxyl group, with conversion of the acid anhydride groups into acid imide groups by reaction with the hydroxyamines C,

to form hydroxy-functional binder components, and subsequent reaction of the hydroxyl groups of the said hydroxy-functional binder components with compounds selected from the group consisting of

compounds D′ containing acid groups, wherein the said subsequent reaction is an esterification reaction, and wherein water is removed, and wherein the reaction products contain at least one acid group per molecule, and of

compounds D″ selected from the group consisting of compounds having at least one isocyanate group and one acid group, and of compounds having at least one isocyanate group and at least one olefinically unsaturated group, wherein the said subsequent reaction is an addition reaction, and wherein the reaction leads to formation of a urethane structure, a urea structure, or a thiourea structure, and wherein the reaction products contain, per molecule, at least one acid group or at least one olefinically unsaturated group.

7. The process of claim 6 wherein the reaction with the compounds D′ is carried out by esterifying the hydroxy-functional binder components with compounds D′ being selected from the group consisting of compounds D 1 , compounds D 2 , compounds D 3 , and compounds D 4 , under removal of water to form reaction products, the said reaction products containing at least one acid group per molecule, and wherein compounds D 1 are polybasic acids having at least two acid groups, compounds D 2 are fatty acids grafted with olefinically unsaturated acids, compounds D 3 are oils grafted with olefinically unsaturated acids, and compounds D 4 are polymers containing acid groups.

8. The process of claim 6 wherein in the reaction with the compounds D″, the said compounds D″ are selected from the group consisting of

compounds D 5 having at least one isocyanate group and at least one acid group, which are adducts of polyfunctional isocyanates with compounds that contain at least one group which is reactive towards isocyanate groups, and at least one acid group, and

compounds D 6 having at least one isocyanate group and at least one olefinically unsaturated group, which are adducts polyfunctional isocyanates and olefinically unsaturated compounds having hydroxyl groups,

wherein the reaction is an addition reaction, and wherein the reaction is carried out by formation of reaction products having a urethane structure, a urea structure or a thiourethane structure, the said reaction products containing either at least one acid group or at least one olefinically unsaturated group per molecule.

9. A process for the preparation of reaction products of hydroxy-functional binder components as claimed in claim 1 , wherein

the said hydroxy-functional binder components contain a linear or branched main chain which has a polymethylene structure —(CH 2 ) n — or a polyester structure or a structure derived from fatty acid esters of glycerol or other polyhydric alcohols, characterised in that they have cyclic imide structures grafted on to the main chain, the imide nitrogen atom carrying a hydroxyalkyl group or a hydroxyalkyl-aryl group as substituent, are reacted with

compounds selected from the group consisting of

compounds D′ containing acid groups, wherein the reaction is an esterification reaction, and wherein water is removed and reaction products are formed, and wherein the said reaction products contain at least one acid group per molecule, and of

compounds D″ selected from the group consisting of compounds having at least one isocyanate group and one acid group, and of compounds having at least one isocyanate group and at least one olefinically unsaturated group, wherein the reaction leads to formation of reaction products having a urethane structure, a urea structure, or a thiourea structure, and wherein the said reaction products contain, per molecule, at least one acid group or at least one olefinically unsaturated group.

10. The process of claim 9 wherein the reaction with the compounds D′ is carried out by esterifying the hydroxy-functional binder components with compounds D′ being selected from the group consisting of compounds D 1 , compounds D 2 , compounds D 3 , and compounds D 4 , under removal of water and reaction products are formed, the said reaction products containing at least one acid group per molecule, and wherein compounds D 1 are polybasic acids having at least two acid groups, compounds D 2 are fatty acids grafted with olefinically unsaturated acids, compounds D 3 are oils grafted with olefinically unsaturated acids, and compounds D 4 are polymers containing acid groups.

11. The process of claim 9 wherein the reaction is an addition reaction, and wherein in the reaction with the compounds D″, the said compounds D″ are selected from the group consisting of

compounds D 5 having at least one isocyanate group and at least one acid group, which are adducts of polyfunctional isocyanates with compounds that contain at least one group which is reactive towards isocyanate groups, and at least one acid group, and

compounds D 6 having at least one isocyanate group and at least one olefinically unsaturated group, which are adducts polyfunctional isocyanates and olefinically unsaturated compounds having hydroxyl groups,

and wherein the reaction is carried out by formation of reaction products having a urethane structure, a urea structure or a thiourethane structure, the said reaction products containing either at least one acid group or at least one olefinically unsaturated group per molecule.

Assignments (3)
CHANGE OF NAME Recorded Dec 27, 2013
From: CYTEC SURFACE SPECIALTIES AUSTRIA GMBH
To: CYTEC AUSTRIA GMBH
Reel/Frame 031870/0323 →
CHANGE OF NAME Recorded Dec 27, 2013
From: CYTEC AUSTRIA GMBH
To: ALLNEX AUSTRIA GMBH
Reel/Frame 031870/0341 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 8, 2006
From: REIDLINGER, GERHARD; BILLIANI, JOHANN; ZRIN, EWALD; SCHERZ, JOHANNES
To: CYTEC SURFACE SPECIALTIES AUSTRIA GMBH
Reel/Frame 018500/0102 →
Priority Claims (1)
AT A 1160/2003 · Jul 23, 2003 · national
Continuity (1)
Related Publication 20060194922A1 · Aug 31, 2006