Curable composition

Abstract

The present application relates to a resin composition or a use thereof. In the present application, it is possible to provide a resin composition or a cured body thereof that exhibits low adhesion force to a predetermined adherend while exhibiting high thermal conductivity. Also, in the present application, the low adhesion force can be achieved without using an adhesion force adjusting component such as a plasticizer or in a state where the use ratio thereof is minimized. The present application can also provide a product comprising the curable composition or the cured body thereof.

Claims

1. A curable composition comprising a polyol compound and a filler, wherein the polyol compound comprises at least one substituent of Formula 1 at its terminal: ##STR00015## wherein in Formula 1, R is a branched alkyl group having 5 or more carbon atoms, a branched alkenyl group having 5 or more carbon atoms, or a branched alkynyl group having 5 or more carbon atoms.

2. The curable composition according to claim 1, forming a cured body having an adhesion force to aluminum of 0.1 N/mm.sup.2 or less.

3. The curable composition according to claim 1, forming a cured body having an adhesion force to a polyester surface of 100 gf/cm or less.

4. The curable composition according to claim 1, forming a cured body having a shore OO hardness of 95 or less.

5. The curable composition according to claim 1, wherein the polyol compound has a polyester backbone or a polyether backbone.

6. The curable composition according to claim 1, wherein the polyol compound has a polycaprolactone backbone or a polyalkylene backbone.

7. The curable composition according to claim 1, wherein the polyol compound comprises a polyol compound having a weight average molecular weight in a range of 100 g/mol to 3000 g/mol.

8. The curable composition according to claim 1, further comprising a polyol compound having no branched hydrocarbon group having 5 or more carbon atoms.

9. The curable composition according to claim 8, wherein the polyol compound having no branched hydrocarbon group having 5 or more carbon atoms comprises a polycaprolactone polyol, or a polyol having an alkanediol unit, a polyol unit, and a dicarboxylic acid unit.

10. The curable composition according to claim 1, further comprising a polyisocyanate.

11. The curable composition according to claim 1, further comprising a plasticizer.

12. The curable composition according to claim 1, wherein the filler is aluminum hydroxide, magnesium hydroxide, calcium hydroxide, hydromagnesite, magnesia, alumina, aluminum nitride, boron nitride, silicon nitride, silicon carbide, zinc oxide or beryllium oxide.

13. A two-component composition comprising: a main part comprising a polyol compound and a filler; and a curing agent part comprising a curing agent component and a filler, wherein the polyol compound comprises at least one substituent of Formula 1 at its terminal: ##STR00016## wherein in Formula 1, R is a branched alkyl group having 5 or more carbon atoms, a branched alkenyl group having 5 or more carbon atoms, or a branched alkynyl group having 5 or more carbon atoms.

14. A product comprising a heat-generating component, and a cured body of the curable composition of claim 1.

15. A product comprising a heat-generating component, and a cured body of the curable composition of the two-component composition of claim 13, which is present adjacent to the heat-generating component.

Description

DESCRIPTION OF DRAWINGS

(1) FIGS. 1 and 2 are analysis results for hydroxy functional components synthesized in Preparation Examples 1 and 2.

DETAILED DESCRIPTION

(2) Hereinafter, the present application will be specifically described through Examples, but the scope of the present application is not limited by the following examples.

(3) The cured body mentioned below is formed by mixing main and curing agent parts of all resin compositions in Examples, which are prepared in a two-component type, so that the OH/NCO equivalent ratio described in each example is satisfied, and then maintaining the mixture at room temperature for about 24 hours.

(4) 1. Thermal Conductivity

(5) The thermal conductivity of the resin composition (curable composition) or the cured body thereof was measured by a hot-disk method according to ISO 22007-2 standard. Specifically, mixtures of the main parts and the curing agent parts in a volume ratio of 1:1 in Examples or Comparative Examples composed of a two-component type were each placed in a mold having a thickness of about 7 mm or so, and the thermal conductivity was measured in the through plane direction using the Hot Disk equipment. As stipulated in the above standard (ISO 22007-2), the Hot Disk equipment is an equipment that can check the thermal conductivity by measuring the temperature change (electrical resistance change) while the sensor with the nickel wire double spiral structure is heated, and the thermal conductivity was measured according to this standard.

(6) 2. Measurement of Adhesion Force to Polyester

(7) The adhesion force to polyester was evaluated for a specimen prepared by attaching a PET (polyethylene terephthalate) film and an aluminum plate. A film having a width of 10 mm or so and a length of 200 mm or so was used as the PET film, and an aluminum plate having each of a width and a length of 100 mm was used as the aluminum plate. A resin composition was applied to the entire surface of the aluminum plate and maintained at room temperature (about 25 C.) for about 24 hours in a state where the PET film was attached on the resin composition to prepare a specimen. At this time, the entire width and 100 mm or so of the length portion in the PET film were attached to the aluminum plate via the resin composition. The adhesion force was measured while the PET film was peeled from the aluminum plate in the longitudinal direction in a state where the aluminum plate of the specimen was fixed. The attachment was performed by applying the resin composition (the mixture of the main part and the curing agent part in a volume ratio of 1:1) to the aluminum plate to have a thickness of about 2 mm or so after curing, and then closely attaching the PET film on the layer of the resin composition, and maintaining them at room temperature (about 25 C.) for about 24 hours to cure the resin composition. The peeling was performed at a peel rate of about 0.5 mm/min or so and a peel angle of 180 degrees until the PET film was completely peeled off.

(8) 3. Measurement of Adhesion Force to Aluminum

(9) An uncured resin composition (a mixture of a main part and a curing agent part) was coated in the center of an aluminum substrate having horizontal and vertical lengths of 2 cm and 7 cm, respectively, to have a width of 2 cm and a length of 2 cm or so, and an aluminum substrate having horizontal and vertical lengths of 2 cm and 7 cm, respectively, was attached again on the coating layer, and the resin composition was cured by maintaining the state. Here, the two aluminum substrates were attached to form an angle of 90 degrees to each other. Hereinafter, with the upper aluminum substrate fixed, the lower aluminum substrate was pressed at a speed of 0.5 mm/min to measure the force while the lower aluminum substrate was separated, and the adhesion force to aluminum was obtained by dividing the maximum force measured in the process by the area of the specimen.

(10) 4. Hardness Measurement

(11) The hardness of the cured body of the resin composition was measured according to ASTM D 2240 and JIS K 6253 standards. It was performed using ASKER's durometer hardness device, where the initial hardness was measured by applying a load of 1 Kg or more (about 1.5 Kg) to the surface of the sample (resin layer) in a flat state, and after 15 seconds, the hardness was evaluated by confirming the stabilized measurement value.

(12) 5. Measurement of Curvature Radius

(13) The curvature radius of the cured body was evaluated using a cured body having a width, a length, and a thickness of 1 cm, 10 cm, and 2 mm, respectively. When the cured body is attached to cylinders having various radii and bent along the longitudinal direction, the curvature radius is the minimum radius of the cylinder at which cracks do not occur in the cured body.

(14) 6. Measurement of Weight Average Molecular Weight

(15) The weight average molecular weight (Mw) was measured using GPC (Gel permeation chromatography). Specifically, the weight average molecular weight (Mw) can be measured by adding a sample to be analyzed into a 5 mL vial, diluting it with a THF (tetrahydrofuran) solvent to a concentration of about 1 mg/mL, and then filtering a standard sample for calibration and the analysis sample through a syringe filter (pore size: 0.45 m). Agilent technologies' ChemStation is used as an analysis program, and the weight average molecular weight (Mw) can be obtained by comparing the elution time of the sample with the calibration curve.

(16) <GPC Measurement Conditions>

(17) Instrument: Agilent technologies' 1200 series Column: using Agilent technologies' TL Mix. A & B Solvent: THF (tetrahydrofuran) Column temperature: 35 C. Sample concentration: 1 mg/mL, 200 l injection Standard samples: using polystyrene (MP: 3900000, 723000, 316500, 52200, 31400, 7200, 3940, 485)

Preparation Example 1

(18) A hydroxy functional component (A) consisting of an oil-modified polyol compound of the following formula A was prepared in the following manner.

(19) ##STR00009##

(20) In Formula A, n and m are each more than 0, and their sum is about 4.8.

(21) Polycaprolactone polyol (Perstorp Capa 3031) and isononanoic acid as a saturated fatty acid were mixed in a weight ratio of 1:0.53 (Capa 3031: isononanoic acid). Subsequently, a catalyst (Tin (II) 2-ethylhexanoate (Sigma-Aldrich)) was added in an amount of 0.1 parts by weight relative to 100 parts by weight of the mixture, and maintained while stirring at 150 C. for 30 minutes under an inert gas purge condition. Subsequently, a small amount of xylene as an azeotropic solution was introduced thereto, the temperature was raised to 200 C., and the mixture was reacted for 3 hours or more, and then the pressure was reduced to 80 Torr or less, and the xylene and unreacted materials were removed. The reactant was filtered after cooling to obtain a target product (compound of Formula A).

(22) As a result of GPC analysis performed on the target product, the weight average molecular weight was about 876 g/mol. FIG. 1 is a view showing the results of GPC analysis performed on the target product.

Preparation Example 2

(23) A hydroxy functional component (B) consisting of an oil-modified polyol compound represented by the following formula B was prepared in the following manner.

(24) ##STR00010##

(25) In Formula B, each n is about 4, R.sub.4 is a substituent of Formula B-1 below, and R.sub.3 is a substituent of Formula B-2 below.

(26) ##STR00011##

(27) In Formula B-1, n is about 4.

(28) ##STR00012##

(29) A compound of Formula C below (PPG, manufacturer: Perstorp, product name: Polyol3380) and isononanoic acid as a saturated fatty acid were mixed in a flask at a weight ratio of 1:0.38 (compound of Formula C: isononanoic acid).

(30) ##STR00013##

(31) In Formula C, each n is about 4, and R.sub.4 is a substituent represented by Formula C-1 below.

(32) ##STR00014##

(33) In Formula C-1, n is about 4.

(34) A catalyst (Tin (II) 2-ethylhexanoate (Sigma-Aldrich)) was added to the mixture in an amount of 0.3 parts by weight relative to 100 parts by weight of the total mixture, and stirred at 150 C. for 30 minutes under an inert gas purge condition. Subsequently, a small amount of xylene as an azeotropic solution was added thereto, the temperature was raised to 190 C., and the mixture was reacted for 10 hours or more, and the pressure was reduced to 40 Torr or less for 1 hour or more to remove xylene and unreacted materials. The reactant was cooled and filtered through a filter to obtain a target product.

(35) As a result of GPC analysis performed on the target product, the weight average molecular weight was about 800 g/mol. FIG. 2 is a view showing the results of GPC analysis performed on the target product.

Example 1

Preparation of Main Part

(36) The main part was prepared by mixing the hydroxy functional component (B) of Preparation Example 2, a filler component and a plasticizer (diisononyl adipate) in a weight ratio of 10:89:1 (component (B):filler component:plasticizer). Here, the filler component was prepared by mixing a first alumina filler having an average particle diameter of about 70 m, a second alumina filler having an average particle diameter of about 20 m, and a third alumina filler having an average particle diameter of about 1 m. The weight ratio during the mixing was about 6:2:2 (first alumina filler:second alumina filler:third alumina filler).

Preparation of Curing Agent Part

(37) A polyisocyanate (Tolonate HDT-LV2, manufactured by Vencorex) was used as a curing agent. The curing agent part was prepared by mixing the polyisocyanate, filler component, and plasticizer (diisononyl adipate) in a weight ratio of 5:5:90 (polyisocyanate:filler component:plasticizer). Here, as the filler component, the same filler component as the filler component of the main part was used.

Preparation of Resin Composition and Cured Body

(38) A resin composition (curable composition) was prepared by preparing the main part and the curing agent part, respectively, and the main and curing agent parts were mixed, and then maintained at room temperature to form a cured body. Here, the mixing was made so that the equivalent ratio (OH/NCO) of the hydroxy group (OH) present in the main part and the isocyanate group (NCO) present in the curing agent part was about 100.

Example 2

(39) A resin composition (curable composition) was prepared by preparing the main part and the curing agent part in the same manner, respectively, as in Example 1, and the main part and the curing agent part were mixed, and then maintained at room temperature to form a cured body, but the mixing was made so that the equivalent ratio (OH/NCO) of the hydroxy group (OH) present in the main part and the isocyanate group (NCO) present in the curing agent part was about 170.

Example 3

Preparation of Main Part

(40) The main part was prepared by mixing the hydroxy functional component (A) of Preparation Example 1, a filler component and a plasticizer (diisononyl adipate) in a weight ratio of 9.7:89:1.3 (component (A):filler component:plasticizer). Here, as the filler component, the same filler component as in Example 1 was used.

Preparation of Curing Agent Part

(41) A polyisocyanate (Vencorex, Tolonate HDT-LV2) was used as a curing agent. The curing agent part was prepared by mixing the polyisocyanate, filler component, and plasticizer (diisononyl adipate) in a weight ratio of 5:5:90 (polyisocyanate:filler component:plasticizer). Here, as the filler component, the same filler component as in Example 1 was used.

Preparation of Resin Composition

(42) A resin composition (curable composition) was prepared by preparing the main part and the curing agent part, respectively, and the main and curing agent parts were mixed, and then maintained at room temperature to form a cured body. Here, the mixing was made so that the equivalent ratio (OH/NCO) of the hydroxy group (OH) present in the main part and the isocyanate group (NCO) present in the curing agent part was about 100.

Example 4

(43) A resin composition (curable composition) was prepared by preparing the main part and the curing agent part in the same manner, respectively, as in Example 3, and the main part and the curing agent part were mixed, and then maintained at room temperature to form a cured body, but the mixing was made so that the equivalent ratio (OH/NCO) of the hydroxy group (OH) present in the main part and the isocyanate group (NCO) present in the curing agent part was about 170.

Example 5

Preparation of Main Part

(44) The main part was prepared by mixing the hydroxy functional component (A) of Preparation Example 1, a general polyol compound (Kuraray, F-2010), a filler component and a plasticizer (diisononyl adipate) in a weight ratio of 11.4:1.1:87:0.5 (component (A):general polyol compound:filler component:plasticizer). Here, as the filler component, the same filler component as in Example 1 was used.

Preparation of Curing Agent Part

(45) A polyisocyanate (Vencorex, Tolonate HDT-LV2) was used as a curing agent. The curing agent part was prepared by mixing the polyisocyanate, filler component, and plasticizer (diisononyl adipate) in a weight ratio of 5:5:90 (polyisocyanate:filler component:plasticizer). Here, as the filler component, the same filler component as in Example 1 was used.

Preparation of Resin Composition

(46) A resin composition (curable composition) was prepared by preparing the main part and the curing agent part, respectively, and the main and curing agent parts were mixed, and then maintained at room temperature to form a cured body. Here, the mixing was made so that the equivalent ratio (OH/NCO) of the hydroxy group (OH) present in the main part and the isocyanate group (NCO) present in the curing agent part was about 179.

Example 6

(47) A resin composition (curable composition) was prepared by preparing the main part and the curing agent part in the same manner, respectively, as in Example 5, and the main part and the curing agent part were mixed, and then maintained at room temperature to form a cured body, but the mixing was made so that the equivalent ratio (OH/NCO) of the hydroxy group (OH) present in the main part and the isocyanate group (NCO) present in the curing agent part was about 157.

Example 7

(48) A resin composition (curable composition) was prepared by preparing the main part and the curing agent part in the same manner, respectively, as in Example 5, and the main part and the curing agent part were mixed, and then maintained at room temperature to form a cured body, but the mixing was made so that the equivalent ratio (OH/NCO) of the hydroxy group (OH) present in the main part and the isocyanate group (NCO) present in the curing agent part was about 140.

Example 8

Preparation of Main Part

(49) The main part was prepared by mixing the hydroxy functional component (A) of Preparation Example 1, a general polyol compound (Kuraray, F-2010), a filler component and a plasticizer (diisononyl adipate) in a weight ratio of 7.4:3.2:87:2.4 (component (A):general polyol:filler component:plasticizer). Here, as the filler component, the same filler component as in Example 1 was used.

Preparation of Curing Agent Part

(50) A polyisocyanate (Vencorex, Tolonate HDT-LV2) was used as a curing agent. The curing agent part was prepared by mixing the polyisocyanate, filler component, and plasticizer (diisononyl adipate) in a weight ratio of 5:5:90 (polyisocyanate:filler component:plasticizer). Here, as the filler component, the same filler component as in Example 1 was used.

Preparation of Resin Composition

(51) A resin composition (curable composition) was prepared by preparing the main part and the curing agent part, respectively, and the main and curing agent parts were mixed, and then maintained at room temperature to form a cured body. Here, the mixing was made so that the equivalent ratio (OH/NCO) of the hydroxy group (OH) present in the main part and the isocyanate group (NCO) present in the curing agent part was about 170.

Example 9

(52) A resin composition (curable composition) was prepared by preparing the main part and the curing agent part in the same manner, respectively, as in Example 8, and the main part and the curing agent part were mixed, and then maintained at room temperature to form a cured body, but the mixing was made so that the equivalent ratio (OH/NCO) of the hydroxy group (OH) present in the main part and the isocyanate group (NCO) present in the curing agent part was about 140.

(53) The physical property evaluation results summarized for the respective examples are as shown in Table 1 below.

(54) TABLE-US-00001 TABLE 1 Adhesion Al force to adhesion Thermal polyester force Shore OO conductivity Curvature (gf/cm) (N/mm.sup.2) hardness (W/mK) radius Example 1 182 0.15 91 2.546 8 Example 2 90 0.13 64 2.626 0 Example 3 333 0.15 98 2.755 >12 Example 4 125 0.039 92 2.631 8 Example 5 96 0.064 74 2.481 4 Example 6 133 0.048 88 2.556 6 Example 7 116 0.07 93 2.434 7 Example 8 255 0.045 86 2.558 3 Example 9 222 0.032 95 2.627 8