US 4,110,279 A · High temperature polymers from methoxy functional ether aromatic monomers

Abstract

A polymer derived by heating in the presence of an acid catalyst at between about 65.degree. C. and 260.degree. C. I. a reaction product, a cogeneric mixture of alkoxy functional compounds, having average equivalent weights in the range from about 220 to about 1200, obtained by heating in the presence of a strong acid at about 50.degree. C. to about 250.degree. C. (a) a diaryl compound selected from naphthalene, diphenyl oxide, diphenyl sulfide, their alkylated or halogenated derivatives or mixtures thereof, (B) formaldehyde or formaldehyde-yielding derivative, (C) water, and (D) a hydroxy aliphatic hydrocarbon compound having at least one free hydroxyl group and from 1 to 4 carbon atoms, which mixture contains up to 50 percent by weight unreacted (A); with Ii. at least one monomeric phenolic reactant selected from the group ##STR1## WHEREIN R is selected from the group consisting of ##STR2## HYDROGEN, ALKYL RADICAL OF 1-20 CARBON ATOMS, ARYL RADICAL OF 6-20 CARBON ATOMS, WHEREIN R.sub.1 represents hydrogen, alkyl or aryl, m represents an integer from 1 to 3; o represents an integer from 1 to 5; p represents an integer from 0 to 3; X represents oxygen, sulfur or alkylidene; and q represents an integer from 0 to 1; and, Iii. optionally an aldehyde or an aldehyde-yielding derivative or a ketone, For from several minutes to several hours. These polymeric materials are liquids or low melting solids which are capable of further modification to thermoset resins. These polymers are capable of being thermoset by heating at a temperature of from about 130.degree. C. to about 260.degree. C. for from several minutes to several hours in the presence of a formaldehyde-yielding compound. These polymers are also capable of further modification by reacting under basic conditions with formaldehyde with or without a phenolic compound. The polymers, both base catalyzed resoles and acid catalyzed novolacs are useful as laminating, molding, film-forming and adhesive materials. The polymers, both resoles and novolacs, can be epoxidized as well as reacted with a drying oil to produce a varnish resin.

Claims18

Dependent claims

A polymer derived by heating in the presence of an acid catalyst at between about 65.degree. C and 260.degree. C

I. a cogeneric mixture of alkoxy functional compounds, having an average equivalent weight in the range from about 220 to about 1200, obtained by heating together in the presence of a strong acid at about 50.degree. C to about 250.degree. C;
(a) a diaryl compound selected from naphthalene, diphenyl oxide, diphenyl sulfide, their alkylated or halogenated derivatives or mixtures thereof,
(B) formaldehyde or formaldehyde-yielding derivative,
(C) water, and
(D) a hydroxy aliphatic hydrocarbon compound having at least one free hydroxyl group and from 1 to 4 carbon atoms,
which mixture contains 0 to 50 percent by weight unreacted (A);
with
Ii. up to one monomeric phenolic reactant per equivalent of I selected from the group ##STR11## wherein R is selected from the group consisting of ##STR12## hydrogen, alkyl radical of 1 to 20 carbon atoms, aryl radical of 6 to 20 carbon atoms, R.sub.1 represents hydrogen, alkyl or aryl, m represents an integer from 1 to 3, o represents an integer from 1 to 5;
p represents an integer from 0 to 3;
X represents oxygen, sulfur or C.sub.1 to C.sub.3 alkylidene;
and, q' represents an integer from 0 to 1.

8 more elements

A polymer derived by heating in the presence of an acid catalyst at between about 65.degree. C and 260.degree. C

I. a reaction mixture of alkoxy functional compounds having average molecular weights in the range from 220 to 1200 obtained by heating together in the presence of a strong acid at about 50.degree. C to about 250.degree. C;
(a) a diaryl compound selected from naphthalene, diphenyl oxide, diphenyl sulfide, their alkylated or halogenated derivatives or mixtures thereof,
(B) formaldehyde or formaldehyde-yielding derivative,
(C) water, and
(D) a hydroxy aliphatic hydrocarbon compound having at least one free hydroxyl
group and from 1 to 4 carbon atoms, which mixture contains 0 to 50 percent by weight unreacted (A);
with
Ii. more than one monomeric phenolic reactant per equivalent of I selected from the group ##STR13## wherein R is selected from the group consisting of ##STR14## hydrogen, alkyl radical of 1 to 20 carbon atoms, aryl radical of 6 to 20 carbon atoms, R.sub.1 represents hydrogen, alkyl or aryl, m represents an integer from 1 to 3, o represents an integer from 1 to 5;
p represents an integer from 0 to 3;
X represents oxygen, sulfur or C.sub.1 to C.sub.3 alkylidene;
and, q' represents an integer from 0 to 1;
and a source of an aldehyde in the presence of a strong acid catalyst.

9 more elements

A polymer derived by heating in the presence of an acid catalyst at between about 65.degree. C and 260.degree. C

I. a mixture of alkoxy functional compounds having average molecular weights in the range from 220 to 1200 obtained by heating together in the presence of a strong acid at about 50.degree. C to about 250.degree. C;
(a) a diaryl compound selected from naphthalene, diphenyl oxide, diphenyl sulfide, their alkylated or halogenated derivatives or mixtures thereof,
(B) formaldehyde or formaldehyde-yielding derivative,
(C) water, and
(D) a hydroxy aliphatic hydrocarbon compound having at least one free hydroxyl group and from 1 to 4 carbon atoms,
which mixture contains 0 to 50 percent by weight unreacted (A);
with
Ii. a monomeric phenolic reactant selected from the group ##STR15## wherein R is selected from the group consisting of ##STR16## hydrogen, alkyl radical of 1 to 20 carbon atoms, aryl radical of 6 to 20 carbon atoms, R.sub.1 represents hydrogen, alkyl or aryl, m represents an integer from 1 to 3, o represents an integer from 1 to 5;
p represents an integer from 0 to 3;
X represents oxygen, sulfur or C.sub.1 to C.sub.3 alkylidene;
and, q' represents an integer from 0 to 1;
and optionally a source of an aldehyde in the presence of an acidic catalyst;
with
Iii. an additional source of an aldehyde and a basic catalyst.

11 more elements

Dependencies are inferred from the claim text.

High temperature polymers from methoxy functional ether aromatic monomers

Life of this patent

High temperature polymers from methoxy functional ether aromatic monomers

Life of this patent

Abstract

Claims18