Crystallized diacetylenic indicator compounds and methods of preparing the compounds
View Patent ↗Crystallized diacetylenic compounds having certain crystallographic and other characteristics; diacetylenic compounds and mixtures crystallized from diacetylenic solutions; methods of preparing and identifying solvent systems for dissolving diacetylenic compounds; diacetylenic solutions; methods of recrystallizing diacetylenic compounds; crystals of 2,4-hexadiyn-1,6-bis(alkylurea) compounds; and ambient condition indicators and time-temperature condition indicators comprising crystallized diacetylenic compounds.
1. Crystallized 2,4-hexadiyn-1,6-bis(ethylurea) having a crystal structure wherein the molecules have a center-to-center separation of less than 4.7 Å between the geometric centers of the diacetylene units in neighboring molecules in a direction wherein solid-state polymerization can occur.
2. Crystallized 2,4-hexadiyn-1,6-bis(ethylurea) according to claim 1 wherein the center-to-center separation corresponds to a unit cell repeat distance of the crystallized diacetylenic compound.
3. Crystallized 2,4-hexadiyn-1,6-bis(ethylurea) according to claim 1 having a triclinic crystal structure.
4. Crystallized 2,4-hexadiyn-1,6-bis(ethylurea) according to claim 1 having a triclinic crystal structure in space group P1(bar).
5. Crystallized 2,4-hexadiyn-1,6-bis(ethylurea) according to claim 1 comprising two hydrogen bonds to each urea group in the molecule, each one of the two hydrogen bonds extending between one of the two NH groups in a urea group in one molecule of 2,4-hexadiyn-1,6-bis(ethylurea) and a C═O group in a neighboring molecule of 2,4-hexadiyn-1,6-bis(ethylurea).
6. Crystallized 2,4-hexadiyn-1,6-bis(ethylurea) according to claim 5 having a triclinic crystal structure and a purity of at least about 98 percent by weight.
7. Crystallized 2,4-hexadiyn-1,6-bis(ethylurea) according to claim 1 wherein the center-to-center separation is 4.620 Å.
8. Crystallized 2,4-hexadiyn-1,6-bis(ethylurea) according to claim 1 having a crystal structure with unit cell parameters of a=4.248 Å, b=4.620 Å, c=16.558 Å, 60=88.97° , 62 =84.66° and γ=81.41°.
9. Crystallized 2,4-hexadiyn-1,6-bis(ethylurea) according to claim 8 having a centrosymmetric crystal structure.
10. Crystallized 2,4-hexadiyn-1,6-bis(ethylurea) according to claim 1 having a crystal size in a first direction of greater than about 100 micron and a maximum dimension in a second direction perpendicular to the first direction of not more than about 10 micron.
11. Crystallized 2,4-hexadiyn-1,6-bis(ethylurea) according to claim 1 comprising not more than 3 percent by weight of polymerized 2,4-hexadiyn-1,6-bis(ethylurea), based upon the weight of 2,4-hexadiyn-1,6-bis(ethylurea) and of the polymer.
12. Crystallized 2,4-hexadiyn-1,6-bis(propylurea) having a crystal structure wherein the molecules have a center-to-center separation of less than 4.7 Å between the geometric centers of the diacetylene units in neighboring molecules in a direction wherein solid-state polymerization can occur.
13. Crystallized 2,4-hexadiyn-1,6-bis(propylurea) according to claim 12 wherein the center-to-center separation corresponds to a unit cell repeat distance of the crystallized diacetylenic compound.
14. Crystallized 2,4-hexadiyn-1,6-bis(propylurea) according to claim 12 having a monoclinic crystal structure.
15. Crystallized 2,4-hexadiyn-1,6-bis(propylurea) according to claim 12 having a monoclinic crystal structure in space group P2 1 /a.
16. Crystallized 2,4-hexadiyn-1,6-bis(propylurea) according to claim 12 comprising two hydrogen bonds to each urea group in the molecule, each one of the two hydrogen bonds extending between one of the two NH groups in a urea group in one molecule of 2,4-hexadiyn-1,6-bis(propylurea) and a C═O group in a neighboring molecule of 2,4-hexadiyn-1,6-bis(propylurea).
17. Crystallized 2,4-hexadiyn-1,6-bis(propylurea) according to claim 16 having a monoclinic crystal structure and a purity of at least about 98 percent by weight.
18. Crystallized 2,4-hexadiyn-1,6-bis(propylurea) according to claim 12 wherein the center-to-center separation is 4.594 Å.
19. Crystallized 2,4-hexadiyn-1,6-bis(propylurea) according to claim 12 having a crystal structure with unit cell parameters of a=8.447 Å, b=4.594 Å, c=19.10 Å, α=90° β=91.960°, and γ=90°.
20. Crystallized 2,4-hexadiyn-1,6-bis(propylurea) according to claim 12 comprising not more than 3 percent by weight of polymerized 2,4-hexadiyn-1,6-bis(propylurea), based upon the weight of 2,4-hexadiyn-1,6-bis(propylurea) and of the polymer.