US4278561A
Expired / Lapsed
US
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Fluorinated benzenesulfonate diacetylenes
Assignee: Lifelines Technology Inc
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Filing: 1978-09-13
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Granted: 1981-07-14
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Expires: 1998-09-13
Abstract
Abstract New fluorinated benzenesulfonate diacetylene compositions are described which are useful in time-temperature devices for monitoring the shelf-lives of perishable articles. The compositions are solid-state polymerizable by thermal annealing or exposure to actinic or high energy ionizing radiation. Some of the compositions, in addition, exhibit relatively longer polymerization induction periods, compared to other known diacetylene compositions, and an "autocatalytic" effect upon polymerization during which a rapid color change occurs. These characteristics are extremely useful in monitoring situations which require a striking color change as an indication that a particular time-temperature history profile, e.g. shelf-life, has expired.
Inventors
- 👤 Kwok C. Yee
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 12:59
CPC Classifications
G; G01; G01N; G01N31/00; G01N31/22; G01N31/229; C; C07; C07C; C07C309/00; C07C309/63; C07C309/72; C07C309/73; C08; C08F; C08F138/00; G01N33/00; G01N33/02
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
74 words
A composition of the following formula: ##STR2## wherein m is an integer value from 1 to 4 and X, Y and Z are selected from hydrogen, fluoro and C 1 -C 4 fluorinated normal, iso- or secondary alkyl, containing 1-9 fluorine atoms, said composition being symmetrical and containing at least two fluorine atoms and being capable of undergoing solid state polymerization upon thermal annealing or exposure to actinic radiation or high energy ionizing radiation.
Claim 2
Dependent Claim
74 words
A composition of the following formula: ##STR2## wherein m is an integer value from 1 to 4 and X, Y and Z are selected from hydrogen, fluoro and C 1 -C 4 fluorinated normal, iso- or secondary alkyl, containing 1-9 fluorine atoms, said composition being symmetrical and containing at least two fluorine atoms and being capable of undergoing solid state polymerization upon thermal annealing or exposure to actinic radiation or high energy ionizing radiation.
Claim 3
Dependent Claim
11 words
The composition of claim 1 wherein X and Y are hydrogen.
Claim 4
Dependent Claim
15 words
The composition of claim 2 wherein Z is selected from m-fluoro, p-fluoro, m-trifluoromethyl and p-trifluoromethyl.
Claim 5
Dependent Claim
22 words
The composition of claim 3 selected from the group consisting of 2,4-hexadiyn-1,6-diol bis(p-fluorobenzenesulfonate), 2,4-hexadiyn-1,6-diol bis(m-trifluoromethylbenzenesulfonate), 4,6-decadiyn-1,10-diol bis(m-trifluoromethylbenzenesulfonate), 5,7-dodecadiyn-1,12-diol bis(m-trifluorobenzenesulfonate) and 5,7-dodecadiyn-1,12-diol bis(p-fluorobenzenesulfonate).
Claim 6
Dependent Claim
8 words
The composition of claim 4 being 2,4-hexadiyn-1,6-diol bis(p-fluorobenzenesulfonate).
Claim 7
Dependent Claim
23 words
A colored composition containing up to 10% by weight of a colored polymer of at least one monomer as defined in claim 1.
Claim 8
Dependent Claim
24 words
A colored composition containing from 10% to 100% by weight of a colored polymer of at least one monomer as defined in claim 1.
Claim 9
Dependent Claim
71 words
In a device for monitoring the time-temperature history of a perishable article including a housing, in which is positioned a time-temperature indicating material, capable of undergoing solid state polymerization upon thermal annealing to produce a contrasting color change, prior to the expiration of the shelf-life of said article, and means for observing said color change; the improvement which comprises providing a composition of claim 1 as the time-temperature history indicating material.
Claim 10
Dependent Claim
36 words
The device of claim 8 wherein said composition exhibits a longer induction period, prior to undergoing a contrasting color change upon thermal annealing, as contrasted to the bis(p-toluenesulfonate) of 2,4-hexadiyn-1,6-diol, as measured under the same conditions.
Claim 11
Dependent Claim
12 words
Device of claim 8 wherein the time-temperature indicating material is 2,4-hexadiyn-1,6-diol bis(para-fluorobenzenesulfonate).
Claim 12
Dependent Claim
12 words
Device of claim 8 wherein the time-temperature indicating material is 2,4-hexadiyn-1,6-diol bis(meta-trifluoromethylbenzenesulfonate).
Claim 13
Dependent Claim
78 words
In a device for monitoring the exposure history of a perishable article, during successive time intervals of exposure to the effects of temperature and/or radiation, said device comprising a housing in which is positioned an exposure indicating material capable, upon exposure to thermal annealing and/or to radiation, of undergoing a color change, and positioned to allow observation of said color change; the improvement which consists essentially in providing a composition of claim 1 as the exposure indicating material.
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) | 1984-07-13 | 1985-01-12 | 1985-07-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-07-13 | 1989-01-12 | 1989-07-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-07-13 | 1993-01-12 | 1993-07-14 | $7700.00 | Window Closed / Lapsed |