ADAMANTATE™ is the generic name for a family of derivatives Idemitsu has developed based on adamantane, whose functional group provides the advantages of the adamantane framework in a range of materials. By using ADAMANTATE™ as a base resin, Idemitsu can introduce superior adamantane characteristics such as heat resistance, stiffness and transparency for a variety of products including flat panel displays and semiconductor manufacturing photoresists.
The ADAMANTATE™ Product Lineup
Idemitsu produces many adamantane derivatives carrying the brand name ADAMANTATE™. These advanced products have proven useful for semiconductor applications, as well as the creation of new materials.
Other Adamantane Derivatives
Adamantane and Derivatives
| Chemical name | CAS no. | Structure | Stage |
|---|---|---|---|
| Adamantane (Tricyclo[3.3.1.1.3.7]decane) | 281-23-2 |  |
C |
| 1,3-adamantanediol | 5001-18-3 |  |
C |
| 1,3-dibromoadamantane | 876-53-9 |  |
P |
| 1,3-adamantane dicarboxylic acid | 39269-10-8 |  |
L |
| 1,3-adamantane dimethanol | 17071-62-4 |  |
L |
| 1-adamantanol | 768-95-6 |  |
L |
| 2-adamantanol | 700-57-2 |  |
L |
| 1-adamantane carboxylic acid | 828-51-3 |  |
L |
| 1-adamantane methanol | 770-71-8 |  |
L |
| 2-adamantanone | 700-58-3 |  |
P |
| 1-bromoadamantane | 768-90-1 |  |
L |
C: Commercial; P: Pilot; L: Laboratory
Acrylates
| Product name | Chemical name | CAS no. | Structure | Stage |
|---|---|---|---|---|
| ADAMANTATE™ MM | 2-methyl-2-adamantyl methacrylate | 177080-67-0 |  |
C |
| ADAMANTATE™ EM | 2-ethyl-2-adamantyl methacrylate | 209982-56-9 |  |
C |
| ADAMANTATE™ HM | 3-hydroxy-1-adamantyl methacrylate | 115372-36-6 |  |
C |
| ADAMANTATE™ HA | 3-hydroxy-1-adamantyl acrylate | 209982-56-9 |  |
C |
| ADAMANTATE™ MA | 2-methyl-2-adamantyl acrylate | 249562-06-9 |  |
P |
| ADAMANTATE™ EA | 2-ethyl-2-adamantyl acrylate | 303186-13-3 |  |
P |
| ADAMANTATE™ X-M-104 | 1-adamantyl methacrylate | 16887-36-8 |  |
P |
| ADAMANTATE™ X-A-101 | 1-adamantyl acrylate | 121601-93-2 |  |
L |
C: Commercial; P: Pilot; L: Laboratory
General Properties of a Typical Monomer
| X-M-104 Polymer | PMMA | |
|---|---|---|
| Tg (°C) | 170 to 200 | 108 |
| Total transparency (%, 3 mm) | 91 | 91 to 92 |
| Refractive index | 1.52 | 1.49 |
| Water absorbency | 0.11 | 0.3 |
| Yellow index | 3.2 to 3.6 | 4.1 |
| Chemical name | Structure |
|---|---|
| 1,3-adamantanediol di(meth)acrylate |  |
| 1,3-adamantanedimethenol di(meth)acrylate |  |
* Applications: High transparent resin Heat resistance resin...
Epoxides
| Product name and Chemical name | Structure |
|---|---|
| ADAMANTATE™ E-201 1,3-bis(1-adamantyl)-4,6-bis(glycidyloxy)benzene |
 |
| ADAMANTATE™ X-E-202 1-(2',4'-bis(glycidyloxy)phenyl)adamantane |
 |
| ADAMANTATE™ X-E-203 1,3-bis(4'-glycidyloxyphenyl)adamantane |
 |
| ADAMANTATE™ X-E-401 1,3-bis(2',4'-bis(glycidyloxy)phenyl)adamantane |
 |
* These structures are the model, and contained the compound of many kinds of reaction products actually.
Properties of Curing Compounds
| Structure | Tg (°C) |
Td5 (°C) |
Water absorbance (%) |
Bending strength (MPa) |
Bending elasticity (MPa) |
Shore hardness (D) |
|
|---|---|---|---|---|---|---|---|
| 25°C 24 hr |
100°C 3 hr |
||||||
 |
140 | 341 | 0.12 | 0.34 | 141 | 3083 | 81 |
 |
165 | 362 | 0.10 | 0.27 | 148 | 3207 | 83 |
 |
183 | 366 | 0.06 | 0.25 | 105 | 3547 | 89 |
 |
219 | 347 | 0.08 | 0.44 | 157 | 4368 | 91 |
Tg: differential scanning calorimetry and bending test according to JIS K7171
Td: TG, differential thermal analysis and Shore hardness according to JIS K7215
Curing conditions: 110°C × 2
hr + 150°C × 3 hr
In the presence of 4-methylhexahydrophtalic anhydride
Cat.: 1,8-diaza-bicyclo (5.4.0) undecene octanoate
 |
Tg (°C) |
Td5 (°C) |
Water Absorbance (%) |
Permittivity (1GHz) |
Dissipation factor (1GHz) |
Coefficient of linear expansion (×10-5/°C) |
|
|---|---|---|---|---|---|---|---|
| 25°C 24 hr |
100°C 3 hr |
||||||
| 75/25 | 222 | 353 | 0.17 | 0.36 | 2.61 | 0.009 | 5.80 |
| 50/50 | 210 | 349 | 0.18 | 0.35 | 2.63 | 0.009 | 5.87 |
| 25/75 | 200 | 351 | 0.18 | 0.35 | 2.63 | 0.009 | 6.02 |
| 0/100 | 183 | 366 | 0.06 | 0.25 | 2.71 | 0.012 | 6.30 |
Tg: differential scanning calorimetry
Td: TG and differential thermal analysis
Coefficient of linear expansion: thermochemical analysis
Curing conditions: 110°C × 2
hr + 150°C × 3 hr
In the presence of 4-methylhexahydrophtalic anhydride
Cat.: DBU 1,8-diaza-bicyclo (5.4.0) undecene octanoate
Perfluoroadamantane Acrylate
| Product name | ADAMANTATE™ X-F-101 |
ADAMANTATE™ X-F-102 |
ADAMANTATE™ X-F-203 |
ADAMANTATE™ X-F-204 |
|---|---|---|---|---|
| Structure |  |
 |
 |
 |
| Appearance | Clear liquid | Clear liquid | White solid | White solid |
| Melting point (°C) | 11 to 14 | 24 to 28 | 92 to 107 | 42 to 52 |
| Refractive index (at 25°C) | 1.376 | 1.372 | N/A | N/A |
| Solubility | Soluble acetone Hexane Methanol THF Insoluble water |
Soluble acetone Hexane Methanol THF Insoluble water |
Soluble acetone Hexane Methanol THF Insoluble water |
Soluble acetone Hexane Methanol THF Insoluble water |
Properties of Curing Compounds
| Monomer | Total light transmittance (%) | Refractive index (nD23) | Abbe number |
|---|---|---|---|
| Perfluoroadamantane diacrylate | 95.0 | 1.434 | 47.5 |
 |
94.8 | 1.433 | 44.5 |
| Monomer | Shore hardness (D) | Bending strengt (MPa) | Bending elasticity (MPa) | Shrinkage volume (%) |
|---|---|---|---|---|
| Perfluoroadamantane diacrylate | 87 | 71.5 | 2880 | 5.8 |
|
82 | 32.8 | 1760 | 11.3 |
Optical property: JIS K7105
Bending test: JIS K7171
Shore hardness: JIS K7215
Thickness: 1 mm
Curing conditions:
Initial: Benzoin isobutyl ether (2 wt%)
UV: Mercury lamp
Thickness: 1 mm
*1 N.B. The data shown above was measured under specific conditions and has been verified for accuracy. Nevertheless, results in applications may differ depending on use and products may not perform for all recommended uses depending on use conditions. The content above is subject to change without notice. Figures of physical characteristics of other resins than the products have been referred from other catalogues and sources thereof.
*2 ADAMANTATE is trademarks registerd in Japan under the name of Idemitsu Kosan Co., Ltd.
