# US 5,708,074 A · Anionically stabilized aqueous polyvinylbutyral dispersions and process for their preparation and use

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- Number: US 5,708,074 A
- Document ID: US5708074A
- Status: Granted
- Kind: A
- Application number: 08/640,715
- Filed: 1996-05-01
- Granted: 1998-01-13
- Earliest claimed: 1995-05-02
- Assignees: Hoechst Aktiengesellschaft
- Inventors: Gerhard Merten; Ralph Schaefer; Markus Schafheutle; Martin Gerlitz
- Web page: https://patentgrep.com/patent/US5708074A

## CPC

- C08G 18/8064: {with monohydroxy compounds}
- C08G 18/0823: {containing carboxylate salt groups or groups forming them}
- C08G 18/4063: {Mixtures of compounds of group C08G18/62 with other macromolecular compounds}
- C08G 18/6212: {Polymers of alkenylalcohols; Acetals thereof; Oxyalkylation products thereof}
- C08G 18/67: Unsaturated compounds having active hydrogen
- C08G 18/8048: {with compounds of C08G18/34}
- C08G 18/8054: {with compounds of C08G18/38}
- Y10T 428/2982: Particulate matter [e.g., sphere, flake, etc.]
- Y10T 428/31551: Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

A process for the preparation of water-dilutable polyvinylbutyral dispersions by (1) reacting an aliphatic acid having from one to three isocyanate-reactive groups and from one to three acid groups, or a mixture of such acids, with one or more polyfunctional isocyanates whose average functionality is at least two, where the quantity of the isocyanate component is chosen such that the ratio of the number of isocyanate groups to the number of isocyanate-reactive groups of the acid component is between 2.2:1 and 1.7:1; (2) then reacting from 25 to 75% of the remaining isocyanate groups with at least one monofunctional compound selected from monoalcohols and monoamines; and (3) reacting this NCO-functional emulsifier resin further with polyvinylbutyral and, if desired, with an appropriate plasticizer resin using a suitable auxiliary solvent. The polyvinylbutyral dispersions prepared in this way can be used as binders and binder components for coatings with good adhesion.

## Claims

### Claim 1

A process for the preparation of water-dilutable polyvinylbutyral dispersions, which comprises reacting
A an aliphatic acid having from one to three groups which are reactive toward isocyanate and from one to three acid groups, or a mixture of such acids, with
B one or more polyfunctional isocyanates whose average functionality is at least two,
wherein the quantity of the isocyanate component B is chosen such that the ratio of the number of isocyanate groups to the number of groups of component A which are reactive toward isocyanate is between 2.2:1 and 1.7:1;
continuing the reaction until at least 70% of the isocyanate reactive groups have been consumed;
thereafter reacting from 25 to 75% of the residual isocyanate groups with
C at least one monofunctional compound selected from monoalcohols and monoamines to produce an NCO-functional emulsifier resin; and
further reacting this NCO-functional emulsifier resin with
D a mixture of proportions by mass of
D1 from 30 to 100% of polyvinylbutyral and
D2 from 0 to 70% of a plasticizer resin or of a mixture of plasticizer resins, in the presence of an auxiliary solvent, until achievement of substantially complete conversion of all isocyanate groups, with the proviso that the sum of the proportions by mass of D1 and D2 is 100% and the reaction product formed is a resin having a quantity of acid groups which is such that the acid number based on solid resin is between 5 and 50 mg/g.

### Claim 2 (depends on 1)

A process as claimed in claim 1, wherein component A comprises one or more saturated, linear, branched or cyclic aliphatic acids having 2 to 25 carbon atoms, which are selected from carboxylic, sulfonic and phosphonic acids.

### Claim 3 (depends on 2)

A process as claimed in claim 2, wherein component A comprises one or more saturated, linear, branched or cyclic aliphatic carboxylic acids having 2 to 25 carbon atoms.

### Claim 4 (depends on 1)

A process as claimed in claim 1, wherein the isocyanate-reactive groups of component A are selected from hydroxyl groups, primary and secondary amino groups and mercapto groups.

### Claim 5 (depends on 4)

A process as claimed in claim 4, wherein the isocyanate-reactive groups of component A comprise hydroxyl groups.

### Claim 6 (depends on 4)

A process as claimed in claim 4, wherein the compounds of component A comprise two hydroxyl groups and one carboxylic acid group.

### Claim 7 (depends on 1)

A process as claimed in claim 1, wherein dimethylolpropionic acid is employed as component A.

### Claim 8 (depends on 1)

A process as claimed in claim 1, wherein component A is dissolved in an inert, high-boiling, water-miscible solvent.

### Claim 9 (depends on 1)

A process as claimed in claim 1, wherein component B comprises one or more organic diisocyanates.

### Claim 10 (depends on 9)

A process as claimed in claim 9, wherein up to 10% of the isocyanates of component B comprise isocyanates of higher functionality than said diisocyanates.

### Claim 11 (depends on 9)

A process as claimed in claim 9, wherein the diisocyanates of component B are selected from aliphatic, cycloaliphatic and aromatic diisocyanates having 3 to 30 carbon atoms.

### Claim 12 (depends on 1)

A process as claimed in claim 1, wherein component C is selected from aliphatic alcohols having a linear or branched carbon chain with 2 to 30 carbon atoms; monoetherified mono-, di- and oligoglycols containing oxyalkylene groups having in each case from two to four carbon atoms and a degree of polymerization of up to 20; reaction products of monoepoxides with aliphatic, cycloaliphatic or aromatic monocarboxylic acids; monohydroxy-functional esters of acrylic or methacrylic acid; hydroxy-functional allyl ethers; aliphatic, linear or branched, primary and secondary monoamines having 2 to 30 carbon atoms; polyoxyalkylene-monoamines containing oxyalkylene groups having from two to four carbon atoms; alkoxyalkylamines having 3 to 30 carbon atoms, or mixtures of these compounds.

### Claim 13 (depends on 1)

A process as claimed in claim 1, wherein the polyvinylbutyral of component D1 has a solution viscosity of from 1 to 200 mPa.s, measured on a 6% strength methanolic solution at 23.degree. C., a degree of acetalization of from 65 to 90%, a proportion by mass of acetate groups of from 2 to 5%, and a proportion by mass of hydroxyl groups of from 10 to 30%.

### Claim 14 (depends on 1)

A process as claimed in claim 1, wherein the plasticizer resin is selected from phenolic resins, novolaks, dialkyl phthalates, epoxy resins, castor oil and alkyd resins, or a mixture.

### Claim 15 (depends on 1)

An aqueous polyvinylbutyral dispersion prepared by the process of claim 1.

### Claim 16 (depends on 1)

An aqueous polyvinylbutyral dispersion, prepared by the process of claim 1, comprising an organic solvent in a proportion by mass of from 0.5 to 20%.

### Claim 17 (depends on 15)

A mixture of aqueous binders comprising an aqueous polyvinylbutyral dispersion as claimed in claim 15.

### Claim 18 (depends on 15)

A mixture of aqueous binders comprising an aqueous polyvinylbutyral dispersion as claimed in claim 15 and an aqueous dispersion of a phenolic resin.

### Claim 19 (depends on 15)

A mixture of aqueous binders comprising an aqueous polyvinylbutyral dispersion as claimed in claim 15 and an aqueous dispersion of an amino resin.

### Claim 20 (depends on 15)

A coating composition comprising at least one coating resin and a binder comprising an aqueous polyvinylbutyral dispersion as claimed in claim 15.

### Claim 21 (depends on 15)

A binder for use with abrasives, comprising an aqueous phenolic resin and a flexibilizer resin comprising an aqueous polyvinylbutyral dispersion as claimed in claim 15.

### Claim 22 (depends on 21)

An abrasive, comprising a plurality of abrasive particles bound together with the binder of claim 21.

### Claim 23 (depends on 16)

An adhesion system, comprising a substrate, an adhesion primer applied to the substrate and an adhered layer applied to the adhesion primer, wherein the adhesion primer comprises the aqueous polyvinylbutyral dispersion as claimed in claim 16.