POLYMER

Abstract

The present application relates to a polymer and a use thereof. The present application may provide a functional polymer which expresses a low solubility to a polar solvent and a non-polar solvent and which is suitable for forming a film. If applied to the use of cosmetics such as mascara or to medical uses, the polymer in the present application may express a tolerance to diverse solvents such as sebum, sweat, tears and the like, and thus enables makeup to last, etc. Accordingly, the polymer may be applied to diverse uses and used in film forming agents, cosmetic compositions, or cosmetics, or the like.

Claims

1. A polymer comprising polymerized units of a first monomer of which homopolymer has a solubility parameter of less than 10.0 (cal/cm.sup.3).sup.1/2 and polymerized units of a second monomer of which homopolymer has a solubility parameter of 10.0 (cal/cm.sup.3).sup.1/2 or more, wherein a glass transition temperature is 10° C. or more.

2. The polymer according to claim 1, wherein the solubility is 10 or less in a solvent having a dielectric constant (25° C.) in a range of 1 to 3 and the solubility is 10 or less in a solvent having a dielectric constant (25° C.) in a range of 75 to 85.

3. The polymer according to claim 1, wherein the solubility is 15 or more in a solvent having a dielectric constant (25° C.) in a range of 4 to 15.

4. The polymer according to claim 1, wherein the homopolymer of the first monomer has a solubility parameter in a range of 5 (cal/cm.sup.3).sup.1/2 to 9.5 (cal/cm.sup.3).sup.1/2.

5. The polymer according to claim 1, wherein the first monomer is a compound represented by Formula 1 below: ##STR00004## wherein, Q is hydrogen or an alkyl group, B is a straight or branched alkyl group having 5 or more carbon atoms, an alicyclic hydrocarbon group, or an aromatic substituent.

6. The polymer according to claim 5, wherein in Formula 1 Q is hydrogen or an alkyl group having 1 to 4 carbon atoms and B is an alkyl group having 7 or more carbon atoms or an alicyclic hydrocarbon group having 6 to 12 carbon atoms.

7. The polymer according to claim 1, wherein the homopolymer of the second monomer has a solubility parameter in a range of 10.0 (cal/cm.sup.3).sup.1/2 to 15.0 (cal/cm.sup.3).sup.1/2.

8. The polymer according to claim 1, wherein the second monomer is a compound represented by Formula 2 or 3 below: ##STR00005## wherein Q is hydrogen or an alkyl group, U is an alkylene group, Z is hydrogen or an alkyl group, and m is any number: ##STR00006## wherein Q is hydrogen or an alkyl group, A and U are each independently an alkylene group, and X is a hydroxy group or a cyano group.

9. The polymer according to claim 8, wherein in Formula 3 Q is hydrogen or an alkyl group having 1 to 4 carbon atoms, U is an alkylene group having 1 to 4 carbon atoms, Z is hydrogen or an alkyl group having 1 to 4 carbon atoms and m is a number in a range of 1 to

10. The polymer according to claim 1, comprising 50 to 99.9 parts by weight of the polymerized units of the first monomer and 0.1 to 20 parts by weight of the polymerized units of the second monomer.

11. The polymer according to claim 1, wherein a weight average molecular weight is in a range of 10,000 to 500,000.

12. A film forming agent comprising the polymer of claim 1.

Description

EXAMPLE 1

[0092] As shown in Table 1 below, a monomer mixture in which EHMA (ethylhexyl methacrylate), IBOMA (isobornyl methacrylate) and EOEOEA (ethoxyethoxyethyl acrylate) were mixed in a weight ratio (EHMA:IBOMA:EOEOEA) of 25:60:15 was introduced into isododecane as a solvent to have the total monomer concentration of 35% by weight, and subsequently, the dissolved oxygen was removed by bubbling with nitrogen at room temperature for about 30 minutes together with stirring. The nitrogen bubbling was further carried out for about 40 minutes while elevating the reaction mixture removing oxygen to a temperature of about 70° C. If the temperature increased to 70° C. through the above process, the polymerization reaction proceeded while further introducing an appropriate amount of a thermal initiator (V-65, Wako chemicals) into isododecane as a solvent. After performing the reaction for about 24 hours, the reaction was completed by decreasing the temperature to room temperature to obtain a polymer solution.

EXAMPLES 2 TO 5 AND COMPARATIVE EXAMPLES 1 TO 3

[0093] The polymer solutions were obtained in the same manner as Example 1 except that the monomer types and proportions of the monomer mixture were changed as Table 1 below.

TABLE-US-00001 TABLE 1 Example Comparative Example 1 2 3 4 5 1 2 3 Polymer A B C D E F G H BMA 15 EHA 15 40 LMA 20 15 EHMA 30 CHMA 75 IBOMA 60 74 75 75 50 EOEOEA 10 10 10 10 10 PEGMA 6 TMSS 100 PVP 100 Content unit: g BMA: butyl methacrylate (solubility parameter of homopolymer: 8.8 (cal/cm.sup.3).sup.1/2) EHA: ethyl hexyl acrylate (solubility parameter of homopolymer: 8.4 (cal/cm.sup.3).sup.1/2) LMA: lauryl methacrylate (solubility parameter of homopolymer: 8.2 (cal/cm.sup.3).sup.1/2) EHMA: ethylhexyl methacrylate (solubility parameter of homopolymer: 8.3 (cal/cm.sup.3).sup.1/2) CHMA: cyclohexyl methacrylate (solubility parameter of homopolymer: 7.9 (cal/cm.sup.3).sup.1/2) IBOMA: isobornyl methacrylate (solubility parameter of homopolymer: 8.1 (cal/cm.sup.3).sup.1/2) EOEOEA: ethoxyethoxy ethylacrylate (solubility parameter of homopolymer: 10.6 (cal/cm.sup.3).sup.1/2) PEGMA: polyethyleneglycol monoethyl ether methacrylate (ethylene oxide unit addition mole: 9 moles, solubility parameter of homopolymer: 10.8 (cal/cm.sup.3).sup.1/2) TMSS: trimethylsiloxysilicate (solubility parameter of homopolymer: 7.5 (cal/cm.sup.3).sup.1/2) (Trimethyl siloxysilicate: Dow Corning MQ-1600 Resin) PVP: polyvinyl pyrrolidone (solubility parameter of homopolymer: 11 (cal/cm.sup.3).sup.1/2, Aldrich K30)

[0094] 1. Evaluation of NMR

[0095] As a result of evaluating NMR for the polymer of Example 1 1H peaks derived from ═CH2 of the double bond terminus were little identified, whereby it can be confirmed that the polymerization has been carried out effectively. In addition, —CH— peaks adjacent to —COO— of EHMA and IBOMA forming the polymer and peaks derived from —OCH2CH2O— of EOEOEA were observed in the region of 5.0 μm to 3.5 ppm, where an area value of peaks is 9. Furthermore, peaks derived from —CH2- of the side chain and —CH3 derived from the meta-position were identified in the region of 2.5 ppm to 1.3 ppm as peaks having an area value of 36, and 1H peaks identified from —CH2CH— and —CH2CH2- derived from the polymer backbone, were identified in the region of 1.3 ppm to 0.5 ppm as an area of 55.

[0096] For the polymer of Example 2, NMR was also equally evaluated. As a result of evaluation, 1H peaks derived from ═CH2 of the double bond terminus were little identified, whereby it could be confirmed that the polymerization has been carried out efficiently. In addition, —CH— peaks adjacent to —COO— of EHA and CHMA forming the polymer and peaks derived from —OCH2CH2O— of EOEOEA were identified in the region of 4.8 ppm to 3.4 ppm as an area value of 10. Furthermore, from —CH2- adjacent to —COO— of EHA forming the polymer, peaks having an area value of about 3 were identified in the region o 2.5 ppm to 2.0 ppm, and from —CH2- of the side chain and —CH3 derived from the meta-position, peaks having an area value of 57 were identified in the region of 2.0 ppm to 1.5 ppm. Furthermore, 1H area value identified from —CH2CH— and —CH2CH2- derived from the polymer backbone was about 29 in 1.5 ppm to 0.5 ppm.

[0097] In the case of the polymer of Example 3, 1H peaks derived from ═CH2 of the double bond terminus were little identified. In addition, —CH2- and —CH— peaks adjacent to —COO— of LMA and IBOMA forming the polymer and peaks derived from —OCH2CH2-O and —OCH3 of PEGMA appeared in the region of 4.7 ppm to 3.3 ppm, and the area value of the peaks was 17. Furthermore, peaks from —CH2- of the side chain and —CH3 derived from the meta-position were identified in the region of 2.0 ppm to 1.5 ppm as an area value of 72, and the area value of 1H peaks identified from —CH2CH— derived from the polymer backbone was 11 in the region of 1.5 ppm to 0.5 ppm.

[0098] In results of measuring NMR for the polymer of Example 4, 1H peaks derived from ═CH2 of the double bond terminus were also little observed. In addition, —CH2- and —CH— peaks adjacent to —COO— of LMA and IBOMA forming the polymer and peaks derived from —OCH2CH2O— of EOEOEA appeared in the region of 4.7 ppm to 3.3 ppm, and the area value of the peaks was 9. Furthermore, from —CH2- of the side chain and —CH3 derived from the meta-position, peaks having an area value of 36 were identified in the region of 2.0 ppm to 1.5 ppm, and 1H area value identified from —CH2CH— and —CH2CH2- derived from the polymer backbone was 55 in 1.5 ppm to 0.5 ppm.

[0099] Moreover, in the results of NMR measuring the polymer of Example 5, 1H peaks derived from ═CH2 of the double bond terminus were also little observed. In addition, —CH— peaks adjacent to —COO— of BMA and IBOMA forming the polymer and peaks derived from —OCH2CH2O— of EOEOEA appeared in the region of 4.8 ppm to 3.4 ppm, and the area value of the peaks was 11. Furthermore, from —CH2- of the side chain and —CH3 derived from the meta-position, peaks having an area value of 35 were identified in the region of 2.5 ppm to 1.3 ppm, and 1H area value identified from —CH2CH— and —CH2CH2- derived from the polymer backbone was 54 in 1.3 ppm to 0.5 ppm.

[0100] For the polymer of Comparative Example 3, NMR was also equally evaluated. As a result, —CH— peaks adjacent to —COO— of EHA and IBOMA and peaks derived from —OCH2CH2O— of EOEOEA appeared in the region of 4.8 ppm to 3.4 ppm, and the area value of the peaks was 9. Furthermore, from —CH2- adjacent to —COO— of EHA forming the polymer, peaks having an area value of about 8 were identified in 2.5 ppm to 2.0 ppm, and from —CH2— of the side chain and —CH3 derived from the meta-position, peaks having an area value of 21 were identified in the region of 2.0 ppm to 1.5 ppm, and 1H area value identified from —CH2CH— and —CH2CH2- derived from the polymer backbone was 61 in 1.5 ppm to 0.5 ppm.

[0101] 2. Physical Property Evaluation Results

[0102] The results of measuring physical properties for each polymer of Examples and Comparative Examples were summarized and described in Table 2 below.

TABLE-US-00002 TABLE 2 Example Comparative Example 1 2 3 4 5 1 2 3 Polymer A B C D E F G H Solubility Hexane D C D D D A D C Ethyl A A A A A A D A acetate Acetone C D D D D A D B Water D D D D D D A D Weight average 340,000 300,000 200,000 200,000 350,000 — — 200,000 molecular weight Glass transition 39 31 38 42 65 — — −8 temperature (° C.) Sebum In-vitro 3.9 4.0 3.8 4.0 4.0 3.0 3.3 3.3 blurring In-vivo 3200 3100 3200 3000 3000 4500 3800 3800 Water resistance test A A A A A A B A

[0103] It can be confirmed from the above results that in the case of the polymer satisfying the requirements of the present application, it exhibits a low solubility in polar solvents (water, acetone) and non-polar solvents (hexane) and exhibits an excellent solubility in solvents (ethyl acetate) having middle characteristics. Also, if such a polymer was applied, it was confirmed to have an excellent sebum resistance even in the sebum blurring test while securing water resistance.