COLORANT FOR HEAT TRANSFER FLUID, AND COMPOSITION COMPRISING SAME

Abstract

The present invention relates to a colorant for a heat transfer fluid, and a composition comprising same.

Claims

1. A colorant having a structure of Chemical Formula 1 below:
R-[X-A-Z].sub.y  [Chemical Formula 1] wherein in Chemical Formula 1, R is a chromophore; X is a linker that links the chromophore and a water-soluble group; A is a water-soluble group for giving water solubility to the colorant; Z is an alkyl group containing a C.sub.0 to C.sub.4 as an end substituent; and y is an integer of 4 to 16.

2. The colorant of claim 1, wherein the colorant is a porphyrin related tetrapyrrole compound, a phthalocyanine related tetrapyrrole compound, or a porpyrazine related tetrapyrrole compound.

3. The colorant of claim 1, X is selected from the group consisting of C, O, N, and S.

4. The colorant of claim 1, wherein A is a C.sub.1 to C.sub.4 alkoxy group.

5. The colorant of claim 1, wherein the colorant has a structure of Chemical Formula 2 or 3 below: ##STR00005## wherein in Chemical Formula 2 or 3, M is a metal or a metalloid.

6. The colorant of claim 5, wherein the metal or metalloid is copper (Cu), zinc (Zn), silicon (Si), aluminum (Al), gallium (Ga), indium (In), titanium (Ti), tin (Sn), or ruthenium (Ru).

7. The colorant of claim 1, wherein the colorant has a solubility of 1.0 g/L or more with respect to a cooling liquid composition.

8. The colorant of claim 1, wherein the colorant has a weight loss rate of 10% or less at a temperature of 250° C. or lower.

9. A cooling liquid composition, comprising: 0.001 to 10.000 wt % of the colorant of claim 1; 30 to 70 wt % of a glycol compound; and 30 to 70 wt % of water.

10. The cooling liquid composition of claim 9, further comprising 0.001 to 0.100 wt % of a defoamer relative to the total weight thereof.

11. The cooling liquid composition of claim 9, further comprising 0.0005 to 0.1 wt % of a pH adjuster relative to the total weight thereof.

12. The cooling liquid composition of claim 11, wherein the pH adjuster is an amine-based compound.

13. The cooling liquid composition of claim 12, wherein the amine-based compound is at least one selected from the group consisting of alkanol amines, alkyl amines, and cyclic amines.

14. The cooling liquid composition of claim 12, wherein the amine-based compound is triethanolamine.

15. The cooling liquid composition of claim 9, further comprising a metal corrosion inhibitor.

16. The cooling liquid composition of claim 15, wherein the metal corrosion inhibitor is an azole.

17. The cooling liquid composition of claim 9, wherein the cooling liquid composition is a cooling liquid composition for an internal combustion engine, a cooling liquid composition for an electric battery, or a cooling liquid composition for a fuel cell.

18. The cooling liquid composition of claim 9, wherein the cooling liquid composition has an electrical conductivity of 50.0 uS/cm or less.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0075] FIG. 1 is a picture showing colors of colorant compounds prepared according to examples of the present disclosure.

[0076] FIG. 2 is a graph showing ion exchange resin passage evaluation results of the colorant compound (Example 1) prepared according to the example of the present disclosure.

[0077] FIG. 3 is a picture showing ion exchange resin passage evaluation results of a colorant compound (Example 1) prepared according to an example of the present disclosure.

[0078] FIG. 4 is a graph showing ion exchange resin passage evaluation results of a colorant compound (Example 2) prepared according to the example of the present disclosure.

[0079] FIG. 5 is a picture showing ion exchange resin passage evaluation results of a colorant compound (Example 2) prepared according to an example of the present disclosure.

BEST MODE FOR CARRYING OUT THE INVENTION

[0080] An antifreeze composition containing: 0.001 to 10.000 wt % of a colorant having a structure of Chemical Formula 1 or 2; 30 to 70 wt % of a glycol compound; and 30 to 70 wt % of water.

DETAILED DESCRIPTION

[0081] Hereinafter, the present disclosure will be described in more detail by the following examples. However, these examples are used only for illustration, and the scope of the present disclosure is not limited by these examples.

Preparation Example 1: Preparation of Example 1

[0082] PEG 400, 4-nitro phthalonitrile, and CsCO.sub.3 were added and reacted at 70° C. for 12 hours, and THF was used as a solvent. After the reaction, THF and CsCO.sub.3 were removed, and then the reaction product was washed to obtain PEG-PN, a primary reaction product. The synthesized PEG-PN was used to synthesize a colorant. Specifically, PEG-PN, CuCl.sub.2, and DBU were reacted at 160° C. for 8 hours. Thereafter, solvent removal, washing, and recrystallization were performed, and then a bluish green colorant was ultimately obtained.

##STR00003##

Preparative Example 2: Preparation of Example 2

[0083] TEG, di-fluorophthalonitrile, and K.sub.2CO.sub.3 were added and reacted at 70° C. for 12 hours, and THF was used as a solvent. After the reaction, THF and K.sub.2CO.sub.3 were removed, and then the reaction product was washed to obtain Di-PEG-PN, a primary reaction product. The synthesized Di-PEG-PN was used to synthesize a colorant. Specifically, Di-PEG-PN, Zn(OAc).sub.2, and DBU were reacted at 160° C. for 8 hours. Thereafter, solvent removal, washing, and recrystallization were performed, and then a bluish green colorant was ultimately obtained.

##STR00004##

Test Example 1: Evaluation of Physiochemical Stability

[0084] Thermogravimetric analysis was measured using a TA Q600 instrument while the temperature was raised to 300° C. at a temperature rise rate of 10° C. per minute in a nitrogen atmosphere. As for the acid/alkali stability test, the decomposition of the compounds in a solution of pH 2 to 12 was investigated through visual observation and the absorbance area change and the absorbance intensity were measured through UV-Vis measurement.

[0085] The results of stability are shown in Table 1 below by marking ⊚ when the weight change rate was 10% or less at 250° C. or higher as a result of thermogravimetric analysis and the acid/alkali stability was excellent; marking ◯ when the weight change rate was approximately 20% at 250° C. or higher as a result of thermogravimetric analysis and the acid/alkali stability was excellent; marking Δ when the weight change rate was approximately 30% at 250° C. or higher as a result of thermogravimetric analysis and the acid/alkali stability was excellent; and marking X in all other cases.

TABLE-US-00001 TABLE 1 Physiochemical Sample stability Example 1 ⊚ Example 2 ⊚

[0086] As can be identified in Table 1, the thermogravimetric analysis results of Examples 1 and 2 could identify that both examples 1 and 2 showed superior thermal stability at a temperature of 250° C. Especially, both Examples 1 and 2 were thermally stable at up to about 300° C., and decomposed at higher temperatures. Examples 1 and 2 were excellent in terms of acid and alkali stability. In other words, Examples 1 and 2 were identified to be thermally and chemically very stable.

Experimental Example 2: Evaluation of Solubility Properties

[0087] As for solubility properties, the solubility was visually observed and measured by preparing 1 L of a cooling liquid at room temperature, adding 0.1 g of a compound, and further adding 0.4 g if the compound was completely dissolved, checking whether the compound was completely dissolved, and then adding 0.5 g. The results are shown in Table 2 by marking ⊚ when the solubility in a commercial cooling liquid composition containing ethylene glycol as a main ingredient was 1.0 g/L or more, ∘ when 0.5 g/L or more, Δ when 0.1 g/L or more, and X when less than the last value.

TABLE-US-00002 TABLE 2 Solubility Sample properties Example 1 ⊚ Example 2 ⊚

[0088] As can be identified in Table 2, Examples 1 and 2 showed superb solubility properties of 1.5 g/L and 3.0 g/L, respectively, in the cooling liquid composition containing ethylene glycol as a main ingredient. That is, Examples 1 and 2 were identified to be well dissolved in a cooling liquid at a higher level compared with other dyes that are usually used, and it can be therefore identified that the colorants of the present disclosure can display colors stably and uniformly in a cooling liquid composition due to excellent solubility properties in the cooling liquid composition.

Experimental Example 3: Evaluation of Electrical Conductivity

[0089] Conductivity was measured for a cooling liquid composition containing 0.01 wt % of a colorant by using a TCX-90.sup.3 instrument, and the results are shown in Table 3.

TABLE-US-00003 TABLE 3 Electrical conductivity Sample (uS/cm) Example 1 0.944 Example 2 0.951

[0090] As can be identified in Table 3, both the cooling liquid compositions containing Examples 1 and 2 showed electrical conductivity of 1.0 uS/cm or less, indicating vary low electrical conductivity. That is, it was identified that the cooling liquid compositions containing the colorants of the present disclosure showed excellent electric insulation.

Experimental Example 4: Evaluation of Ion Exchange Resin Passage

[0091] An ion exchange resin is used to remove ions eluted from fuel cell cooling system components (stacks, radiators, rubber, etc.) and to maintain electrical conductivity at a constant level. When a cooling liquid passes through the ion exchange resin, a general colorant is decolorized and thus the discriminability of the cooling liquid is lost. Therefore, a developed colorant was applied to a cooling liquid to check whether the cooling liquid was discolored by passing through an ion exchange resin.

[0092] For evaluation, 3 wt % or more of an ion exchange resin was added to a cooling liquid employing a developed colorant and stirred for 30 minutes or more to check a color, and then the ion exchange resin was replaced 3 times. The color development was visually checked and the absorbance intensity values of the solution before and after passage were compared, and the results are shown in Table 4 and FIGS. 2 to 5.

TABLE-US-00004 TABLE 4 First Second Third replacement replacement replacement of ion exchange of ion exchange of ion exchange Sample resin resin resin Example 1 No discoloration No discoloration No discoloration (bluish green) (bluish green) (bluish green) Example 2 No discoloration No discoloration No discoloration (bluish green) (bluish green) (bluish green)

[0093] As can be identified in Table 4 and FIGS. 2 to 5, Examples 1 and 2 did not contaminate ion exchange resins.

INDUSTRIAL APPLICABILITY

[0094] The present disclosure relates to a colorant for a heat transfer fluid and a composition containing the same.