US4339951A
Expired / Lapsed
US
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Tempeature measurement and display of indicia using thermochromic polyacetylenes
Assignee: Honeywell International Inc
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Filing: 1979-04-30
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Granted: 1982-07-20
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Expires: 1999-04-30
Abstract
Abstract Certain polyacetylenes exhibit reversible color changes at transition temperatures in the range -180° to 220° 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.
Inventors
- 👤 Kwok C. Yee
- 👤 Anthony F. Preziosi
- 👤 Gordhanbhai N. Patel
- 👤 Ronald R. Chance
- 👤 Granville G. Miller
- 👤 Ray H. Baughman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 21:22
CPC Classifications
G; G01; G01K; G01K11/00; G01K11/12; G01K11/16; C; C08; C08F; C08F38/00
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
535 words
A device for measuring temperature comprising a substrate having deposited thereon at least one thermochromic polyacetylene being a 1,4 addition polymer of an acetylenic compound selected from the group consisting of (1) polydiacetylenes which are 1,4 addition polymers of 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 1 -C 4 alkoxycarbonylmethyl, linear C 1 -C 4 p- or m-alkylpenyl, o- or m-chlorophenyl or linear C 1 -C 4 monochloroalkyl; (b) n is 3 and R and R' can be the same or different and are linear C 1 -C 4 alkoxycarbonylmethyl, linear C 1 -C 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 1 -C 4 m-alkylphenyl, p-methoxyphenyl or linear C 1 -C 4 m-alkoxyphenyl; (2) polyacetylenic network polymers which are 1,4-addition products of crosslinking of 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 3; and copolymers formed of the above formulas (B), and (C) where n is an integer from 2 to 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 of 1,4 addition polymers of acetylenic compositions having the following formulas: (D) [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; (E) 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 4 -C 18 alkyl, linear C 1 -C 4 o-alkoxyphenyl or linear C 1 -C 4 o-alkylphenyl; (c) n is 2 and R and R' can be the same or different and are linear C 2 -C 18 alkyl, linear C 1 -C 4 alkoxycarbonylmethyl or m-chlorophenyl; (d) n is 1 and R and R' can be the same or different and are linear C 6 -C 18 alkyl, p-chlorophenyl or o-nitrophenyl; (F) 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 1 -C 18 alkyl; (b) n is 3 and R and R' can be the same or different and are linear C 1 -C 18 alkyl; (c) n is 2 and R and R' can be the same or different and are linear C 2 -C 18 alkyl; (G) 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 2 -C 18 alkyl; (b) n is 3 and R and R' can be the same or different and are linear C 1 -C 18 alkyl; (c) n is 2 and R and R' can be the same or different and are linear C 1 -C 18 alkyl or phenyl; and (H) [HO--(CH.sub.2).sub.n --C.tbd.C--C.tbd.C--(CH.sub.2).sub.2 --C.tbd.C].sub.2 wherein n is 2 or 3.
Claim 2
Independent Claim
535 words
A device for measuring temperature comprising a substrate having deposited thereon at least one thermochromic polyacetylene being a 1,4 addition polymer of an acetylenic compound selected from the group consisting of (1) polydiacetylenes which are 1,4 addition polymers of 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 1 -C 4 alkoxycarbonylmethyl, linear C 1 -C 4 p- or m-alkylpenyl, o- or m-chlorophenyl or linear C 1 -C 4 monochloroalkyl; (b) n is 3 and R and R' can be the same or different and are linear C 1 -C 4 alkoxycarbonylmethyl, linear C 1 -C 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 1 -C 4 m-alkylphenyl, p-methoxyphenyl or linear C 1 -C 4 m-alkoxyphenyl; (2) polyacetylenic network polymers which are 1,4-addition products of crosslinking of 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 3; and copolymers formed of the above formulas (B), and (C) where n is an integer from 2 to 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 of 1,4 addition polymers of acetylenic compositions having the following formulas: (D) [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; (E) 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 4 -C 18 alkyl, linear C 1 -C 4 o-alkoxyphenyl or linear C 1 -C 4 o-alkylphenyl; (c) n is 2 and R and R' can be the same or different and are linear C 2 -C 18 alkyl, linear C 1 -C 4 alkoxycarbonylmethyl or m-chlorophenyl; (d) n is 1 and R and R' can be the same or different and are linear C 6 -C 18 alkyl, p-chlorophenyl or o-nitrophenyl; (F) 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 1 -C 18 alkyl; (b) n is 3 and R and R' can be the same or different and are linear C 1 -C 18 alkyl; (c) n is 2 and R and R' can be the same or different and are linear C 2 -C 18 alkyl; (G) 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 2 -C 18 alkyl; (b) n is 3 and R and R' can be the same or different and are linear C 1 -C 18 alkyl; (c) n is 2 and R and R' can be the same or different and are linear C 1 -C 18 alkyl or phenyl; and (H) [HO--(CH.sub.2).sub.n --C.tbd.C--C.tbd.C--(CH.sub.2).sub.2 --C.tbd.C].sub.2 wherein n is 2 or 3.
Claim 3
Dependent Claim
26 words
The device of claim 1 wherein the thermochromic polyacetylene possesses a hysteresis transition temperature which is at least about 5° C. below its thermochromic transition temperature.
Claim 4
Dependent Claim
48 words
The device of claim 2, further comprising a recording thermometer, wherein the thermochromic polyacetylene possesses a thermochromic transition temperature of at least about 5° above ambient temperature, of about 20° to 30° C., and a hysteresis transition temperature of at least about 5° C. below said ambient temperature.
Claim 5
Dependent Claim
27 words
A device for displaying indicia comprising a substrate having deposited thereon at least one thermochromic polyacetylene, as defined in claim 1, in the form of a symbol.
Claim 6
Dependent Claim
26 words
The device of claim 4 wherein the thermochromic polyacetylene possesses a hysteresis transition temperature which is at least about 5° C. below its thermochromic transition temperature.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-07-19 | 1986-01-18 | 1986-07-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-07-19 | 1990-01-18 | 1990-07-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-07-19 | 1994-01-18 | 1994-07-20 | $7700.00 | Window Closed / Lapsed |