Aromatic aldehyde, and epoxy resin curing agent and epoxy resin composition comprising the aromatic aldehyde

Patent metadata

Field	Value
Publication number	US-9745410-B2
Application number	US-201314404560-A
Country	US
Kind code	B2
Filing date	May 17, 2013
Priority date	May 29, 2012
Publication date	Aug 29, 2017
Grant date	Aug 29, 2017

Abstract

There are provided a novel aromatic aldehyde compound capable of providing an epoxy resin coating film and an epoxy resin cured material satisfying all of the excellent surface property (smoothness, gloss), drying property, water resistance, transparency and adhesion, and an epoxy resin curing agent and an epoxy resin composition containing the aromatic aldehyde compound. The aromatic aldehyde has a branched alkyl group having 10 to 14 carbon atoms.

First claim

The invention claimed is:

1. An epoxy resin curing agent, comprising (A) a polyamine compound and (B) an aromatic aldehyde comprising a branched alkyl group,
wherein the branched alkyl group has 10 to 14 carbon atoms, and
wherein the aromatic aldehyde is represented by the following formula (II):

wherein R 1 and R 2 each independently represent an alkyl group comprising 1 to 12 carbon atoms, and a total number of the carbon atoms of R 1 and R 2 is 9 to 13.

2. The epoxy resin curing agent according to claim 1 , wherein (A) the polyamine compound is at least one selected from the group consisting of a polyamine represented by the following formula (A1), a linear aliphatic polyamine represented by the following formula (A2), and a compound obtained by adding a polyamine represented by the following formula (A1) or (A2) to a compound comprising a glycidyl group in one molecule thereof:
H 2 N—CH 2 -A-CH 2 —NH 2   (A1)

wherein A is a phenylene group or a cyclohexylene group; and
H 2 N—(CH 2 CH 2 NH) n —CH 2 CH 2 NH 2   (A2)

3. An epoxy resin composition, comprising the epoxy resin curing agent according to claim 1 .

4. The epoxy resin composition according to claim 3 , for coating or for civil engineering and construction.

5. A cured epoxy resin coating film, manufactured by curing the epoxy resin composition according to claim 3 .

6. A cured epoxy resin, manufactured by curing the epoxy resin composition according to claim 3 .

7. A method for producing an aromatic aldehyde, wherein the aromatic aldehyde is represented by the following formula (II):

wherein R 1 and R 2 each independently represent an alkyl group comprising 1 to 12 carbon atoms, and a total number of the carbon atoms of R 1 and R 2 is 9 to 13,
the method comprising formylating an aromatic compound which has a branched alkyl group comprising 10 to 14 carbon atoms with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride.

8. The epoxy resin curing agent according to claim 1 , wherein the aromatic aldehyde is at least one selected from the group consisting of 4-(dodecan-6-yl)benzaldehyde and 4-(dodecan-5-yl)benzaldehyde.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• Kitamura Mitsuharu
• Matsuura Yutaka
• Kuwahara Hisayuki
• Wada Tomotaka
• Asai Yuiga

Classifications

• C09D163/00

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title

• C08G59/4007

  Curing agents not provided for by the groups C08G59/42 - C08G59/66 · CPC title

• C07C45/50

  by oxo-reactions · CPC title

• C07C47/228

  containing six-membered aromatic rings, e.g. phenylacetaldehyde · CPC title

• C07C211/27

  having amino groups linked to the six-membered aromatic ring by saturated carbon chains · CPC title