IP Library Patent Application 14127850
Patent Application
App. No. 14/127,850

COMPOSITIONS PREPARED FROM AN ALDEHYDE AND A FURFURYL ALCOHOL AND THEIR USE

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Quick Facts
Patent No.
US None
App. No.
14/127,850
Abstract

A furfuryl alcohol derivative having the general formula X[—CH(OR) 2 ] m is prepared by an aldehyde with a furfuryl alcohol in the presence of a copper catalyst. In this formula, X is an aliphatic, cycloaliphatic, aromatic or araliphatic group, R is a 2-furyl group, 2-(5-methylol) furyl group or a mixture thereof, and m is in the range of from 1 to 5. Reaction conditions allow a product having less than 25% free furfuryl alcohol, providing a composition that is suitable as a binder for foundry aggregate in producing a foundry mix.

Claims (46)

1 . A compound of the structure:

X[—CH(OR) 2 ] m   (I)

wherein:

R is a 2-furfuryl group, a 2-(5-methylol) furfuryl group or a combination thereof,

m is in the range of from 1 to 5, and

X is an aliphatic, cycloaliphatic, aromatic or araliphatic group.

2 . A process for making the compound of claim 1 , comprising the step of:

reacting a furfuryl alcohol with an aldehyde in the presence of a copper catalyst, under conditions of dynamic covalent chemistry such that a resulting furfuryl alcohol derivative (“FAD”) composition contains less than 25 percent by weight of free furfuryl alcohol.

3 . (canceled)

4 . The process of claim 2 , wherein:

the aldehyde is reacted with the furfuryl alcohol in an equivalent ratio in the range of from 4:1 to 8:1 molar equivalents.

5 . The process of claim 2 , wherein:

the copper catalyst is copper(II) tetrafluoroborate, copper chloride and mixtures thereof.

6 . The process of claim 2 , wherein:

the aldehyde is a monoaldehyde selected from the group consisting of: formaldehyde, acetaldehyde, propanal, butyraldehyde, benzaldehyde, cinnamaldehyde, and furfural.

7 . The process of claim 2 , wherein:

the aldehyde is a dialdehyde selected from the group consisting of: glyoxal, succindialdehyde, glutaraldehyde, and phthaldialdehyde.

8 . The process of claim 2 , wherein:

the aldehyde is poly(aldehyde guluronate).

9 . A foundry mix, comprising:

a major amount of foundry aggregate; and

a binder, comprising the composition of claim 15 .

10 . The foundry mix of claim 9 , further comprising:

a liquid curing catalyst, preferably selected from the group consisting of copper chloride, copper toluene sulphonate, aluminum phenol sulphonate, phenol sulphonic acid, p-toluene sulphonic acid, lactic acid, benzene sulfonic acid, xylene sulfonic acid, sulfuric acid, salts thereof and mixtures thereof.

11 . The foundry mix of claim 10 , wherein:

the liquid curing catalyst is present in an amount from about 1 to 60 weight percent, based upon the weight of the binder.

12 . A “no-bake” process for forming a foundry shape, comprising the steps of:

introducing the foundry mix of claim 10 into a pattern to form a foundry shape;

allow the liquid curing catalyst present in the foundry mix to cure the formed foundry shape until the formed foundry shape is sufficiently cured to be handleable; and

removing the formed and cured foundry shape from the pattern.

13 . A “cold box” process for forming a foundry shape, comprising the steps of:

introducing the foundry mix of claim 9 into a pattern to form a foundry shape;

contacting the formed foundry shape with a vaporous curing catalyst capable of curing the formed foundry shape until the formed foundry shape is sufficiently cured to be handleable; and

removing the formed and cured foundry shape from the pattern.

14 . A “hot box” process for forming a foundry shape, comprising the steps of:

introducing the foundry mix of claim 10 into a pattern to form a foundry shape;

allow the liquid curing catalyst present in the foundry mix to cure the formed foundry shape until the formed foundry shape is sufficiently cured to be handleable; and

removing the formed and cured foundry shape from the pattern.

15 . A composition, comprising:

a phenolic resin; and

a furfuryl alcohol derivative (“FAD”), having free furfuryl alcohol content of less than 25% by weight, having a structure:

X[—CH(OR) 2 ] m

wherein:

R is a 2-furfuryl group, a 2-(5-methylol) furfuryl group or a combination thereof,

m is in the range of from 1 to 5, and

X is an aliphatic, cycloaliphatic, aromatic or araliphatic group.

Assignments (2)
RELEASE OF SECURITY INTEREST Recorded May 18, 2017
From: INVESTEC BANK, PLC, AS SECURITY AGENT
To: ASK CHEMICALS LP
Reel/Frame 042498/0029 →
SECURITY AGREEMENT SUPPLEMENT Recorded Oct 9, 2014
From: ASK CHEMICALS LP
To: INVESTEC BANK PLC, AS SECURITY AGENT
Reel/Frame 033944/0454 →