JP4258381B2 - ポリエステルの製造方法 - Google Patents
ポリエステルの製造方法 Download PDFInfo
- Publication number
- JP4258381B2 JP4258381B2 JP2004000912A JP2004000912A JP4258381B2 JP 4258381 B2 JP4258381 B2 JP 4258381B2 JP 2004000912 A JP2004000912 A JP 2004000912A JP 2004000912 A JP2004000912 A JP 2004000912A JP 4258381 B2 JP4258381 B2 JP 4258381B2
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- Prior art keywords
- toner
- polyester
- dispersion
- acid
- producing
- 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.)
- Expired - Lifetime
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- -1 anthraquinone compound Chemical class 0.000 claims description 28
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- PYFRLDVYGBCYLI-UHFFFAOYSA-N decyl dihydrogen phosphite Chemical compound CCCCCCCCCCOP(O)O PYFRLDVYGBCYLI-UHFFFAOYSA-N 0.000 description 1
- NMGYKLMMQCTUGI-UHFFFAOYSA-J diazanium;titanium(4+);hexafluoride Chemical compound [NH4+].[NH4+].[F-].[F-].[F-].[F-].[F-].[F-].[Ti+4] NMGYKLMMQCTUGI-UHFFFAOYSA-J 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- HTDKEJXHILZNPP-UHFFFAOYSA-N dioctyl hydrogen phosphate Chemical compound CCCCCCCCOP(O)(=O)OCCCCCCCC HTDKEJXHILZNPP-UHFFFAOYSA-N 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- IRXRGVFLQOSHOH-UHFFFAOYSA-L dipotassium;oxalate Chemical compound [K+].[K+].[O-]C(=O)C([O-])=O IRXRGVFLQOSHOH-UHFFFAOYSA-L 0.000 description 1
- RXCBCUJUGULOGC-UHFFFAOYSA-H dipotassium;tetrafluorotitanium;difluoride Chemical compound [F-].[F-].[F-].[F-].[F-].[F-].[K+].[K+].[Ti+4] RXCBCUJUGULOGC-UHFFFAOYSA-H 0.000 description 1
- VVTXSHLLIKXMPY-UHFFFAOYSA-L disodium;2-sulfobenzene-1,3-dicarboxylate Chemical compound [Na+].[Na+].OS(=O)(=O)C1=C(C([O-])=O)C=CC=C1C([O-])=O VVTXSHLLIKXMPY-UHFFFAOYSA-L 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 150000002291 germanium compounds Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940097364 magnesium acetate tetrahydrate Drugs 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- XKPKPGCRSHFTKM-UHFFFAOYSA-L magnesium;diacetate;tetrahydrate Chemical compound O.O.O.O.[Mg+2].CC([O-])=O.CC([O-])=O XKPKPGCRSHFTKM-UHFFFAOYSA-L 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000003607 modifier Substances 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
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- WVWHRXVVAYXKDE-UHFFFAOYSA-N piperine Natural products O=C(C=CC=Cc1ccc2OCOc2c1)C3CCCCN3 WVWHRXVVAYXKDE-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- HHDOORYZQSEMGM-UHFFFAOYSA-L potassium;oxalate;titanium(4+) Chemical compound [K+].[Ti+4].[O-]C(=O)C([O-])=O HHDOORYZQSEMGM-UHFFFAOYSA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 238000001028 reflection method Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000013555 soy sauce Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Landscapes
- Investigating Or Analysing Materials By Optical Means (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
凍結粉砕した樹脂粒状体ポリエステルペレット試料0.50gを、フェノール/1,1,2,2−テトラクロロエタン(重量比1/1)の混合溶媒に溶解させて濃度(c)1.0g/dlの溶液を調製した。この際、溶融重合樹脂の場合は110℃で20分かけて溶解し、固相重合樹脂の場合は120℃で20分かけて溶解した。その後、ウベローデ型毛細粘度管を使用し、30℃で、原液との相対粘度(ηrel)を測定し、この相対粘度(ηrel)−1から求めた比粘度(ηsp)と濃度(c)との比(ηsp/c)を求めた。同様の方法により、濃度(c)が0.5g/dl、0.2g/dl、0.1g/dlの各場合についても比(ηsp/c)を求めた。そして、これらの値より、濃度(c)を0に外挿したときの比(ηsp/c)を固有粘度〔η〕(dl/g)として求めた。
内径36mm、深さ15mmの円柱状の粉体測色用セルに、樹脂粒状体試料をすりきりに充填し、測色色差計(日本電色工業社製「ND−300A」)を使用し、JIS Z8730の参考1に規定される、Lab表色系によるハンターの色差式の色座標bを、反射法により、測定セルを90度ずつ回転させて4箇所測定した値の単純平均値として求めた。色座標b値はマイナスになるほど青味が強く、逆に、プラスになるほど黄味が強い色調を表す。
トナー(有機系調色剤)として、カラーインデックスで、ソルベントブルー104(クラリアント社製「Polysynthren Blue RBL」使用。以下、「S.B.104」と略す。)とソルベントレッド135(クラリアント社製「Sandoplast Red G」使用。以下、「S.R.135」と略す。)を使用した。分液ロートに、上記のトナーの混合エチレングリコール分散液1mLとクロロホルム30mLを添加し、よく振り混ぜてトナーをクロロホルム相へ抽出した。抽出溶液(クロロホルム相)を採取し、分光光度計にて450nmと632nmの吸光度を測定し、後述する検量式よりトナー濃度を定量した。
分液ロートに、「S.B.104」/「S.R.135」混合エチレングリコールスラリー分散液(調製濃度0.050/0.050w%)1mLとクロロホルム30mLを添加し、よく振り混ぜてトナーをクロロホルム相に抽出した。抽出溶液(クロロホルム相)を採取し、分光光度計にて450nmと632nmの吸光度を測定した。
<トナー濃度の定量>
「S.B.104」/「S.R.135」混合エチレングリコール分散液0.074/0.102wt%を調製し(分散液A)、分液ロートに分散液A1mLとクロロホルム30mLを添加し、よく振り混ぜてトナーをクロロホルム相に抽出した。抽出溶液(クロロホルム相)を採取し、分光光度計にて450nmと632nmの吸光度を測定し、前記の検量式より濃度を定量した。その結果を表1に示す。
実施例1において、抽出操作を省略し、分散液A(エチレングリコール分散液)のまま吸光度を測定した。その結果を表2に示す。
実施例2
スラリー調製槽、それに直列に接続された2段のエステル化反応槽、2段目のエステル化反応槽に直列に接続された3段の溶融重縮合槽から成る連続重合装置を使用し、スラリー調製槽に、テレフタル酸とエチレングリコールを重量比で8W65:485の割合で連続的に供給すると共に、エチルアシッドホスフェートの0.6重量%エチレングリコール溶液を、得られるポリエステル樹脂1トン当たりのリン原子としての総量Pが0.129モル/樹脂トンとなる量で連続的に添加し、且つ、トナー分散液調製槽にて調製した「S.B.104」/「S.R.135」混合エチレングリコール分散液(調製濃度0.10/0.10wt%)を、得られるポリエステル樹脂1トン当たりのトナーの総量が1.0g/樹脂トンとなる量で連続的に添加した。
実施例2において、「S.B.104」/「S.R.135」0.1/0.1wt%混合エチレングリコール分散液を、得られるポリエステル樹脂1トン当たりのトナーの総量が1.0g/樹脂トンとなる様に調製濃度から計算して連続的に添加したこと以外は、同様の方法にてポリエステル樹脂を製造した。この樹脂のカラーb値を表5に示す。
Claims (6)
- トナー分散液調製工程、反応系にトナー分散液を混合する工程、エステル化またはエステル交換反応工程、重縮合工程を含み、トナーを含有するポリエステルを連続式に製造する方法に於いて、トナーがポリエステルの色調改良剤として使用される化合物であり、反応系にトナー分散液を混合する工程を行なうに際し、トナー分散液と有機溶媒とを接触させて有機溶媒でトナーを抽出し、得られた抽出溶液の吸光度を測定することにより、トナー分散液中のトナー濃度を定量し、その結果に基づき、生成ポリマーに対するトナー添加量が所定の量となる様にトナー分散液の供給量および/またはトナー分散液調製濃度をコントロールすることを特徴とするポリエステルの製造方法。
- トナーが、アントラキノン系化合物およびペリノン系化合物の群から選択される1種または2種以上である請求項1に記載のポリエステルの製造方法。
- トナーが、カラーインデックスのソルベントブルー97、ソルベントブルー104、ソルベントレッド135、ソルベントレッド179の群から選択される1種または2種以上である請求項1又は2に記載のポリエステルの製造方法。
- 分散媒がエチレングリコール及び/又は水である請求項1〜3の何れかに記載のポリエステルの製造方法。
- トナーの抽出に使用する有機溶媒がクロロホルム又はトルエンである請求項1〜4の何れかに記載のポリエステルの製造方法。
- ポリエステルがその製造過程で重縮合触媒として使用されたチタンを含んでいる請求項1〜5の何れかに記載のポリエステルの製造方法。
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