US 4,215,208 A · Thermochromic polyacetylenes containing urethane groups

Abstract

Certain polyacetylenes exhibit reversible color changes at transition temperatures in the range -180.degree. to 220.degree. C., wherein the thermochromic cycles can be repeated many times with no apparent degradation and little change in spectroscopic properties. These thermochromic polyacetylenes are useful in temperature-indicator and indicia-display device applications. A process for laser-beam recording of images is described employing a thermochromic polyacetylene, in which the hysteresis properties of the polyacetylene can be suitably altered allowing for selectively storing or erasing the formed image.

A thermochromic polyacetylene composition selected from the group consisting of

(1) polydiacetylenes obtained by polymerizing monomers having the following formula:
(A) RHNOCO--(CH.sub.2).sub.n --C.tbd.C--C.tbd.C--(CH.sub.2).sub.n --OCONHR' wherein
(a) n is 4 and R and R' can be the same or different and are isopropyl, n-octadecyl, linear C.sub.1 -C.sub.4 p- or m-alkylphenyl, o- or m-chlorophenyl or linear C.sub.1 -C.sub.4 monochloroalkyl;
(b) n is 3 and R and R' can be the same or different and are, linear C.sub.1 -C.sub.4 m-alkylphenyl, m- or p-chlorophenyl;
(c) n is 2 and R and R' can be the same or different and are linear C.sub.1 -C.sub.4 m-alkylphenyl, p-methoxyphenyl or linear C.sub.1 -C.sub.4 m-alkoxyphenyl;
(2) polyacetylenic network polymers obtained by 1,4-addition of crosslinkable polyacetylenes having the following formulas:
(B) [OCONH(CH.sub.2).sub.6 --NHOCO(CH.sub.2).sub.n --C.tbd.C--C.tbd.C--(CH.sub.2).sub.2 --C.tbd.C--C.tbd.C--(CH.sub.2).sub.n ].sub.x wherein x is large and n is an integer from 2-6;
(C) {OCONH-(CH.sub.2).sub.6 --NHOCO(CH.sub.2).sub.n --[C.tbd.C--C.tbd.C--(CH.sub.2).sub.2 ].sub.2 C.tbd.C--C.tbd.C--(CH.sub.2).sub.n }.sub.x wherein x is large and n is 3;
and copolymers formed of the above formulas (B), and (C) where n is 3;
(3) partially polymerized acetylenic compounds containing from about 0.1 to about 50 weight percent polymer obtained by polymerizing acetylenic compositions having the following formulas:
(C) {OCONH--(CH.sub.2).sub.6 --NHOCO(CH.sub.2).sub.n [C.tbd.C--C.tbd.C--(CH.sub.2).sub.2 ].sub.2 C.tbd.C--C.tbd.C--(CH.sub.2).sub.n }.sub.x wherein x is large and n is 2 or 4;
(D) RNHOCO(CH.sub.2).sub.n --C.tbd.C--C.tbd.C--(CH.sub.2).sub.n --OCONHR' wherein
(a) n is 4 and R and R' are p-chlorophenyl,
(b) n is 3 and R and R' can be the same or different and are linear C.sub.4 -C.sub.18 alkyl, linear C.sub.1 -C.sub.4 o-alkoxyphenyl or linear C.sub.1 -C.sub.4 o-alkylphenyl;
(c) n is 2 and R and R' can be the same or different and are linear C.sub.2 -C.sub.18 alkyl, alkoxy- or m-chlorophenyl;
(d) n is 1 and R and R' can be the same or different and are linear C.sub.6 -C.sub.18 alkyl;
(E) RNHOCO--(CH.sub.2).sub.n --C.tbd.C--C.tbd.C--(CH.sub.2).sub.2 --C.tbd.C--C.tbd.C--(CH.sub.2).sub.n --OCONHR' wherein
(a) n is 4 and R and R' can be the same or different and are linear C.sub.1 -C.sub.18 alkyl;
(b) n is 3 and R and R' can be the same or different and are linear C.sub.1 -C.sub.18 alkyl;
(c) n is 2 and R and R' can be the same or different and are linear C.sub.2 -C.sub.18 alkyl;
(F) RNHOCO--(CH.sub.2).sub.n --[C.tbd.C--C.tbd.C--(CH.sub.2).sub.2 ].sub.2 --C.tbd.C--C.tbd.C--(CH.sub.2).sub.n --OCONHR' wherein
(a) n is 4 and R and R' can be the same or different and are linear C.sub.2 -C.sub.18 alkyl;
(b) n is 3 and R and R' can be the same or different and are linear C.sub.1 -C.sub.18 alkyl;
(c) n is 2 and R and R' can be the same or different and are linear C.sub.1 -C.sub.18 alkyl or phenyl;
and
(G) [HO--(CH.sub.2).sub.n --C.quadrature.C--C.tbd.C--(CH.sub.2).sub.2 --C.tbd.C].sub.2 wherein n is 2 or 3.

23 more elements

Thermochromic polyacetylenes containing urethane groups

Life of this patent

Thermochromic polyacetylenes containing urethane groups

Life of this patent

Abstract

Claims14