JPH0359026A - Fluorinated polyester - Google Patents
Fluorinated polyesterInfo
- Publication number
- JPH0359026A JPH0359026A JP19267389A JP19267389A JPH0359026A JP H0359026 A JPH0359026 A JP H0359026A JP 19267389 A JP19267389 A JP 19267389A JP 19267389 A JP19267389 A JP 19267389A JP H0359026 A JPH0359026 A JP H0359026A
- Authority
- JP
- Japan
- Prior art keywords
- structural units
- formulas
- fluorine
- diol
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 17
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract 2
- 239000011737 fluorine Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 9
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- DAHZCNRVTNHGGR-UHFFFAOYSA-N 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononane-1,2-diol Chemical compound OCC(O)CC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F DAHZCNRVTNHGGR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
- 238000006068 polycondensation reaction Methods 0.000 description 6
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- -1 polytetrafluoroethylene Polymers 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 238000012696 Interfacial polycondensation Methods 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 239000004811 fluoropolymer Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は透明性を有し、かつ優れた撥水、撥油性を有す
る樹脂、フィルム等の成形物として有用な含弗素ポリエ
ステルに関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a fluorine-containing polyester that is transparent and has excellent water and oil repellency and is useful as a molded product such as a resin or film.
有ｉ弗ｇ化合物、特にパーフルオロアルキル基を有する
化合物は低い臨界界面張力を有し、顕著な撥水、撥油性
を示す。そして脂肪族ポリマーではあるが、ポリテトラ
フルオロエチレンに代表される弗素ポリマーは弗素の有
する特有の性質、例えば耐熱性、耐薬品性、撥油、撥水
性、非粘着性々どの優れた特性を活かし、高機能樹脂フ
ィルムとしてその用途は最近ではかなり広範囲に及んで
いる。Compounds having a perfluoroalkyl group, particularly compounds having a perfluoroalkyl group, have a low critical interfacial tension and exhibit remarkable water and oil repellency. Although they are aliphatic polymers, fluoropolymers such as polytetrafluoroethylene take advantage of the unique properties of fluorine, such as heat resistance, chemical resistance, oil repellency, water repellency, and non-stick properties. Recently, its use as a high-performance resin film has expanded considerably.
本発明は透明性を有し、かつ優れた撥水、撥油性を有す
る樹脂、フィルム等の成形物として有用な含弗素ポリエ
ステルを提供するものである。The present invention provides a fluorine-containing polyester that is transparent and has excellent water and oil repellency and is useful as molded products such as resins and films.
本発明者らはポリエチレンテレフタレートの側鎖部分に
弗化アルキル基を導入することにより、透明でかつ撥水
、撥油性に優れた含弗素ポリエステルを見出し、本発明
を完成した。The present inventors have discovered a fluorine-containing polyester that is transparent and has excellent water and oil repellency by introducing a fluorinated alkyl group into the side chain portion of polyethylene terephthalate, and have completed the present invention.
本発明は、−数式
％式％（）
（式中Ｒｆは炭素原子数１〜１０のフルオロアルキル基
、Ｒは炭素原子数１〜１０のフルキレン基、Ｒ１は二価
の芳香族基又は脂肪族基を示す）で表わされる構造単位
からなり、構造単位α）と（ＩＩ＋とのモル比が１００
１０〜２０／８０で、構造単位（１）と（ＩＩ）の合計
モル数と構造単位（Ｉ［Ｄのモル数が実質的に等しい含
弗素ポリエステルである。The present invention is based on the following formula: The molar ratio of the structural units α) and (II+) is 100.
It is a fluorine-containing polyester in which the total number of moles of structural units (1) and (II) and the number of moles of structural unit (I[D) are substantially equal to 10 to 20/80.
本発明の含弗素ポリエステルは常法により、製造するこ
とができる。すなわち二塩基酸と弗素含有ジオールとの
直接法、又はテレフタル酸ジメチル等の二塩基酸の低級
アルキルエステルとのエステル交換反応により製造する
ことができる。この際触媒として亜鉛、コバルト、マン
ガン、カルシウム、チタン、アンチモン、ケルマニウム
等の金属化合物、安定剤としてリン酸、亜リン酸、ホス
ホン酸又はこれらのエステル等が必要に応じて添加され
る。The fluorine-containing polyester of the present invention can be produced by a conventional method. That is, it can be produced by a direct method using a dibasic acid and a fluorine-containing diol, or by a transesterification reaction between a dibasic acid and a lower alkyl ester such as dimethyl terephthalate. At this time, metal compounds such as zinc, cobalt, manganese, calcium, titanium, antimony, and kermanium are added as catalysts, and phosphoric acid, phosphorous acid, phosphonic acid, or esters thereof as stabilizers are added as necessary.
重縮合反応は、通常、溶融状態で行われるが、溶融重縮
合反応、溶液重縮合反応、界面重縮合反応により得られ
たプレポリマーを固相重縮合反応に付することもできる
。The polycondensation reaction is usually carried out in a molten state, but a prepolymer obtained by a melt polycondensation reaction, a solution polycondensation reaction, or an interfacial polycondensation reaction can also be subjected to a solid-phase polycondensation reaction.
本発明では弗素含有ジオール成分として、４゜４．４−
）リフルオロブタン−１，２−ジオール、４．４，５
．５−テトラフルオロペンタン−１，２−ジオール、４
，４，５，５．５−ぺ／タフルオロペンタンー１．２−
ジオール、４．４．５．５．６．６−ヘキサフルオロヘ
キサン−１，２−ジオール、４，４，５．５，６，６．
６−へブタフルオロヘキサン−１，２−ジオール、４．
４．５．５．６．６．７．７−オクタフルオロペンタン
−１，２−ジオール、４，４．５，５，６，６，７，７
，８，８，９．９．９−トリデカフルオロノナン−１，
２−ジオール、４．４，５．５．６．６．７，７．８．
８，９，９．１０．１０，１１，１１．ｉｆ −ヘプタ
デカフルオロトリデカン−１，２−ジオール等が用いら
れる。In the present invention, as a fluorine-containing diol component, 4°4.4-
) Refluorobutane-1,2-diol, 4.4,5
．． 5-tetrafluoropentane-1,2-diol, 4
,4,5,5.5-pe/tafluoropentane-1.2-
Diol, 4.4.5.5.6.6-hexafluorohexane-1,2-diol, 4,4,5.5,6,6.
6-hebutafluorohexane-1,2-diol, 4.
4.5.5.6.6.7.7-octafluoropentane-1,2-diol, 4,4.5,5,6,6,7,7
,8,8,9.9.9-tridecafluorononane-1,
2-diol, 4.4, 5.5.6.6.7, 7.8.
8, 9, 9. 10. 10, 11, 11. if -heptadecafluorotridecane-1,2-diol and the like are used.
また弗素非含有ジオールとしてエチレングリコール、ネ
オペンチルグリコール、ブチレングリコール等が用いら
れる。弗素含有ジオール成分と弗素非含有ジオール成分
の使用量はモル比で１００１０〜２０／８０である。Ethylene glycol, neopentyl glycol, butylene glycol, etc. are also used as fluorine-free diols. The molar ratio of the fluorine-containing diol component to the fluorine-free diol component is 10,010 to 20/80.
二塩基酸としては、テレフタル酸、イソフタル酸、１．
４−ナフタレンジカルボン酸、１．５−ナフタレンジカ
ルボン酸、２．６−ナフタレンジカルボン酸等の芳香族
二塩基酸、又はマロン酸、コハク酸、グルタル酸、アジ
ピン酸、ピメリン酸、スヘリ／酸、アゼライン酸、セバ
シン酸等の脂肪族二塩基酸の１種又は２種以上の混合物
が用いられる。Examples of dibasic acids include terephthalic acid, isophthalic acid, 1.
Aromatic dibasic acids such as 4-naphthalene dicarboxylic acid, 1.5-naphthalene dicarboxylic acid, 2.6-naphthalene dicarboxylic acid, or malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, Suheri/acid, azelain One or a mixture of two or more of aliphatic dibasic acids such as sebacic acid and sebacic acid are used.
二塩基酸の使用量は、弗素含有ジオール成分と弗素非含
有ジオール成分の合計モル数と実質的に等しいモル数で
ある。The amount of dibasic acid used is substantially equal to the total number of moles of the fluorine-containing diol component and the fluorine-free diol component.
本発明の含弗素ポリエステルは、透明性を有し、かつ優
れた撥水、撥油性を有する。このポリエステルは、樹脂
、フィルム等の成形物として有用である。The fluorine-containing polyester of the present invention has transparency and excellent water and oil repellency. This polyester is useful as molded products such as resins and films.
以下、実施例により本発明の詳細な説明する。 Hereinafter, the present invention will be explained in detail with reference to Examples.
実施例１
４．４，５，５．６．６．７．７．Ｂ、８．９．９．９
− ） ゛リデカフルオロノナンー１，２−ジオール３
９４重量部とテレフタル酸ジメチル８．３重量部を攪拌
機付きの重縮合反応器に仕込み、重縮合触媒としてテト
ラブチルチタネート０．０１部をブタノール１０％溶液
として添加し、窒素気流下１８０°Ｃ常圧で５時間反応
させた後、２ ｓ ｏ ’ｃに昇温し、徐々に減圧して
１時間でｌｍｍＨｇ以下とし、この条件下で３時間重合
反応を行った。透明なボリエステル２３．１重量部が得
られた。Example 1 4.4, 5, 5.6.6.7.7. B, 8.9.9.9
-) Ridecafluorononane-1,2-diol 3
94 parts by weight and 8.3 parts by weight of dimethyl terephthalate were placed in a polycondensation reactor equipped with a stirrer, 0.01 part of tetrabutyl titanate was added as a 10% butanol solution as a polycondensation catalyst, and the mixture was heated at 180°C under a nitrogen stream. After reacting under pressure for 5 hours, the temperature was raised to 2 s o 'C, the pressure was gradually reduced to 1 mmHg or less in 1 hour, and the polymerization reaction was carried out under these conditions for 3 hours. 23.1 parts by weight of transparent polyester were obtained.
実施例２
４．４．５，５，６，６，７，７．８，８，９，９．９
−トリデカフルオロノナン−１，２−ジオール１９．
ｙ 重ＪＩＳ、 −ｃ。Example 2 4.4.5, 5, 6, 6, 7, 7.8, 8, 9, 9.9
-tridecafluorononane-1,2-diol19.
y heavy JIS, -c.
チレングリコール６．１重量部及びテレフタル酸ジメチ
ル８．６重量部を用いて実施例１と同様の方法で透明な
ポリエステル１８．７重量部を得た。18.7 parts by weight of transparent polyester was obtained in the same manner as in Example 1 using 6.1 parts by weight of ethylene glycol and 8.6 parts by weight of dimethyl terephthalate.
実施例１及び２で得られた透明々ポリエステルは示差熱
分析法により非品性であることが示された。またＦ含量
を元素分析法により求め共重合比を求めた。The transparent polyesters obtained in Examples 1 and 2 were shown to be of poor quality by differential thermal analysis. Further, the F content was determined by elemental analysis and the copolymerization ratio was determined.
第１図及び第２図にそれぞれの赤外分光スペクトルを示
す。また溶融圧延フィルムにし水との接触角を測定した
ところ９１°及び６５°であった。FIG. 1 and FIG. 2 show their respective infrared spectra. Furthermore, when the contact angle of the melt-rolled film with water was measured, it was 91° and 65°.
第１図は実施例１で得られたポリエステルの赤外分光ス
ペクトル、第２図は実施例２で得られたポリエステルの
赤外分光スペクトルを示す。FIG. 1 shows an infrared spectrum of the polyester obtained in Example 1, and FIG. 2 shows an infrared spectrum of the polyester obtained in Example 2.
Claims (1)
基、Ｒは炭素原子数１〜１０のアルキレン基、Ｒ＾１は
二価の芳香族基又は脂肪族基を示す）で表わされる構造
単位からなり、構造単位（１）と（II）とのモル比が１
００／０〜２０／８０で、構造単位（ I ）と（II）の
合計モル数と構造単位（III）のモル数が実質的に等し
い含弗素ポリエステル。[Claims] General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (III) (In the formula R_f is a fluoroalkyl group having 1 to 10 carbon atoms, R is an alkylene group having 1 to 10 carbon atoms, R^1 is a divalent aromatic group or an aliphatic group), The molar ratio of structural units (1) and (II) is 1
A fluorine-containing polyester ranging from 00/0 to 20/80, in which the total number of moles of structural units (I) and (II) is substantially equal to the number of moles of structural unit (III).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19267389A JPH0359026A (en) | 1989-07-27 | 1989-07-27 | Fluorinated polyester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19267389A JPH0359026A (en) | 1989-07-27 | 1989-07-27 | Fluorinated polyester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0359026A true JPH0359026A (en) | 1991-03-14 |
Family
ID=16295140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19267389A Pending JPH0359026A (en) | 1989-07-27 | 1989-07-27 | Fluorinated polyester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0359026A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8953426B2 (en) | 2012-10-05 | 2015-02-10 | Panasonic Intellectual Property Management Co., Ltd. | Information reproducing apparatus and information reproducing method |
-
1989
- 1989-07-27 JP JP19267389A patent/JPH0359026A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8953426B2 (en) | 2012-10-05 | 2015-02-10 | Panasonic Intellectual Property Management Co., Ltd. | Information reproducing apparatus and information reproducing method |
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