Process for preparing an indicator composition and indicator compositions
View Patent ↗Indicator inks, indicators formed by printing or otherwise utilizing the inks and host products utilizing the indicators are disclosed. Reactivity-enhancing adjuvants stimulate enhanced thermal reactivity of diacetylenic or other indicator agents capable of responding to ambient thermal conditions with a visual change signaling an end point. The diacetylenic or other agents may be sensitive or relatively insensitive to ambient temperatures. Use of a reactivity-enhancing adjuvant provides a useful means for adapting the reactivities of indicator agents to the response characteristics of prospective host products, for example perishables such as vaccines or fresh fish and maturables such as fruit, cheese and wine. Some exemplary adjuvants include low-temperature polymerization initiators, for example methyl ethyl ketone peroxide and polymerization accelerators, for example cobalt compounds. Such initiators and accelerators can also be used in combination.
1. A process for preparing an indicator composition comprising: contacting solid particles of a diacetylenic indicator agent dispersed in a liquid medium with a non-gaseous reactivity-enhancing adjuvant without heating to provide an indicator composition;
wherein the solid particles of the diacetylenic indicator agent in the indicator composition have an increased polymerization reactivity as compared to an indicator composition that is identical except that it lacks the non-gaseous reactivity enhancing adjuvant;
wherein the diacetylenic indicator agent comprises about 1 wt. % to about 30 wt. % of the indicator composition;
wherein the diacetylenic indicator agent is insoluble in the liquid medium and is polymerizable in response to ambient temperature heat exposure to exhibit an appearance change;
wherein the diacetylenic indicator agent is an acetylenic compound having the structure:
[R′NHC(O)NH(CH 2 ) n —(C≡C—)] 2
wherein n is an integer from 1 to 10 and R′ is a linear alkyl group having 1 to 18 carbon atoms or wherein the diacetylenic agent is an acetylenic compound selected from the group consisting of 2,4-hexadiyn-1,6-bis(ethylurea), 2,4-hexadiyn-1,6-bis(propylurea), 2,4-hexadiyn-1,6-bis(butylurea), 2,4-hexadiyn-1,6-bis(octylurea), 2,4-hexadiyn-1,6-bis(dodecylurea), 2,4-hexadiyn-1,6-bis(octyldecylurea), 5,7-dodecadiyn-1,12 diol bis(n-octadecyl urethane), 2,4-hexadiyn-1,6-diol bis(phenylurethane), 2,4-hexadiyn-1,6-diol bis(p-methoxybenzene sulfonate), 9-(N-carbazolyl)-5,7-nonadiyn-1-ol phenylurethane, o,o′-diacetylenyldiphenyl glutarate, 2,4-hexadiyn-1,6-diol-bis-p-toluene sulfonate, 2,4-hexadiyn-1,6-diol-bis-(p-chlorobenzene sulfonate), (N,N-diacetyl)-diaminodiphenyldiacetylene, and di-(phenylureido)-diphenyldiacetylene;
wherein the non-gaseous reactivity-enhancing adjuvant comprises a polymerization initiator in the amount from about 0.2 wt. % to about 10 wt. % based on the weight of the indicator composition; and the polymerization initiator is selected from the group consisting of azonitrile, alkyl peroxide, peroxyester, hydroperoxide, acyl peroxide, ketone peroxide, peroxyketal, peroxydicarbonate, redox initiator, and combinations thereof or the polymerization initiator is selected from the group consisting of a polymerization initiator having a 10-hour half-life of not more than about 50° C., an azo initiator having a 10-hour half-life of not more than about 50° C., an organic peroxide having a 10-hour half-life of not more than about 50° C., a room-temperature ketone peroxide polymerization initiator and combinations thereof.
2. The process according to claim 1 , wherein the non-gaseous reactivity-enhancing adjuvant is in solution.
3. The process according to claim 1 , further comprising dispersing the solid particles of the polyacetylenic agent in the liquid medium and dissolving or dispersing the non-gaseous reactivity-enhancing adjuvant in the liquid medium wherein the non-gaseous reactivity-enhancing adjuvant enhances the ambient temperature thermal reactivity of the dried indicator composition.
4. The process according to claim 1 , wherein the non-gaseous reactivity-enhancing adjuvant is a dispersible solid.
5. The process according to claim 1 , further comprising correlating the reactivity of the diacetylenic indicator agent with the temperature-response parameters of a prospective host product.
6. The process according to claim 1 , wherein no polymerization accelerator is present.
7. The process according to claim 1 , further comprising dissolving or dispersing a film-forming agent in the liquid medium.
8. The process according to claim 1 , wherein the non-gaseous reactivity-enhancing adjuvant further comprises a polymerization accelerator in an amount from about 0.01 wt. % to about 5 wt. % based on the weight of the indicator composition.
9. The process according to claim 8 , wherein the polymerization accelerator comprises a single metal salt of a carboxylic acid, a mixed metal salt of a carboxylic acid, a single metal salt of an organic acid, or a mixed metal salt of an organic acid.
10. The process according to claim 8 , wherein the polymerization accelerator comprises ions selected from the group consisting of transitional metal ions, cobalt ions, iron ions, manganese ions, vanadium ions, calcium ions, lithium ions, potassium ions, cerium ions, rare earth metal ions, zinc ions, zirconium ions, strontium ions, and combinations thereof.
11. The process according to claim 1 , further comprising fabricating a time-temperature indicator by applying the indicator composition to a substrate.
12. The process according to claim 11 , further comprising associating the time-temperature indicator device with the prospective host product.