Aqueous binder compositions of aliphatic or cycloaliphatic dicarboxaldehydes and resorcinol

Patent metadata

Field	Value
Publication number	US-9574079-B2
Application number	US-201414552889-A
Country	US
Kind code	B2
Filing date	Nov 25, 2014
Priority date	Nov 26, 2013
Publication date	Feb 21, 2017
Grant date	Feb 21, 2017

Abstract

The present invention provides substantially formaldehyde free aqueous thermosetting binder resins from resorcinol and cycloaliphatic dialdehydes, glutaraldehyde or their mixtures and urea which may be excluded or included up to amounts which deter hot wet tensile strength in the cured binder. The compositions provide binders that on a performance cost basis are equivalent to phenol formaldehyde resins but without the formaldehyde.

First claim

We claim:

1. A substantially formaldehyde free thermosetting binder composition that is free from added formaldehyde and phenol formaldehyde resins and which does not liberate substantial formaldehyde as a result of drying and/or curing, the composition comprising resorcinol dialdehyde resin from (i) resorcinol and (ii) one or more dialdehyde selected from the group consisting of cyclohexane dicarboxaldehyde, glutaraldehyde, and their mixtures and, further comprising an epoxy functional hydrolysable silane in the amount of from 0.3 to 1.5 wt.%, based on total resin composition solids, the compositions comprising aqueous or non-aqueous systems, wherein in the compositions, the ratio of the number of hydroxyl equivalent groups of the resorcinol to the number of aldehyde equivalent groups of the one or more dialdehyde ranges from 1:1 to 4:1, and, further,
wherein when the (ii) one or more dialdehyde is glutaraldehyde the composition further comprises (iii) urea in the amount of from 0 to 10 moles urea per mole of glutaraldehyde.

2. The composition as claimed in claim 1 , wherein the dialdehyde is a cyclohexane dialdehyde selected from the group consisting of cis-1,3cyclohexane dicarboxaldehyde, a trans-1,3 cyclohexane dicarboxaldehyde, a cis-1,4cyclohexane dicarboxaldehyde, a trans-1,4 cyclohexane dicarboxaldehyde, and mixtures of any two or more thereof and dissolved in water in presence of resorcinol.

3. The composition as claimed in claim 1 , further comprising a base catalyst, the equivalent ratio of hydroxy groups in the base catalyst to the hydroxy groups which are present in the aqueous mixture of resorcinol and dialdehyde ranges from 0:1 to 0.28:1.

4. The composition as claimed in claim 1 , comprising resorcinol dialdehyde resin from the (i) resorcinol, the (ii) one or more dialdehyde (iii) urea and (iv) base.

5. The composition as claimed in claim 1 , wherein the number of hydroxyl equivalent groups of the resorcinol to the number of aldehyde equivalent groups of the one or more dialdehydes ranges from 1:1 to 3:1.

6. The composition as claimed in claim 1 , wherein the epoxy functional hydrolysable silane is 3-glycidoxypropyl trimethoxy silane.

7. The composition as claimed in claim 1 , wherein the binder composition is an aqueous binder composition or a binder composition powder.

8. A method of making a substantially formaldehyde free thermosetting binder composition that is free from added formaldehyde, are free from added phenol formaldehyde and which do not liberate substantial formaldehyde as a result of drying and/or curing, the method comprising reacting an aqueous mixture of (i) resorcinol and (ii) one or more dialdehyde selected from the group consisting of cyclohexane dicarboxaldehyde, glutaraldehyde, and their mixtures in the presence of a hard base catalyst to form a resorcinol dialdehyde resin, wherein the ratio of the number of hydroxyl equivalent groups of the resorcinol to the number of aldehyde equivalent groups of the one or more dialdehyde ranges from 1:1 to 4:1, and,
further comprising including in the composition an epoxy functional hydrolysable silane in the amount of from 0.3 to 1.5 wt.%, based on total resin composition solids.

9. The method as claimed in claim 8 , wherein the aqueous mixture further comprises (iii) urea.

Assignees

• Rohm & Haas
• Dow Global Technologies Llc

Inventors

• Finch William C
• Mulik Sudhir M
• Sekharan Manesh Nadupparambil

Classifications

• C08G14/08

  Ureas; Thioureas · CPC title

• C08L61/12 Primary

  with polyhydric phenols · CPC title

• C09J161/34

  Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C09J161/04, C09J161/18 and C09J161/20 · CPC title

• C09J161/12

  with polyhydric phenols · CPC title

• C08K5/5435

  containing oxygen in a ring · CPC title