JP2007224263A - ヒドロキシアルキル化キトサン溶液 - Google Patents
ヒドロキシアルキル化キトサン溶液 Download PDFInfo
- Publication number
- JP2007224263A JP2007224263A JP2006213775A JP2006213775A JP2007224263A JP 2007224263 A JP2007224263 A JP 2007224263A JP 2006213775 A JP2006213775 A JP 2006213775A JP 2006213775 A JP2006213775 A JP 2006213775A JP 2007224263 A JP2007224263 A JP 2007224263A
- Authority
- JP
- Japan
- Prior art keywords
- chitosan
- acid
- hydroxyalkylated
- solution
- hydroxyalkylated chitosan
- 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.)
- Granted
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- 229920001661 Chitosan Polymers 0.000 title claims abstract description 172
- 150000007524 organic acids Chemical class 0.000 claims abstract description 31
- 239000000758 substrate Substances 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000002798 polar solvent Substances 0.000 claims abstract description 19
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 239000000243 solution Substances 0.000 claims description 93
- 238000000576 coating method Methods 0.000 claims description 47
- 239000011248 coating agent Substances 0.000 claims description 45
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
- 239000007864 aqueous solution Substances 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 17
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 12
- 230000006196 deacetylation Effects 0.000 claims description 11
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- 150000007519 polyprotic acids Polymers 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 8
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 6
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 3
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 3
- 239000001630 malic acid Substances 0.000 claims description 3
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- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
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- 230000032683 aging Effects 0.000 description 4
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- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
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- RLHGFJMGWQXPBW-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC(CC=2NC=NC=2)=C1O RLHGFJMGWQXPBW-UHFFFAOYSA-N 0.000 description 1
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
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Abstract
【解決手段】非プロトン性極性溶媒中にヒドロキシアルキル化キトサンと有機酸またはその誘導体とを含むことを特徴とするヒドロキシアルキル化キトサン溶液。
【選択図】なし
Description
前述の如く、これまでのところ疎水性または親油性表面の塗布に適する有機溶媒を使用したキトサン誘導体(ヒドロキシアルキル化キトサン)の溶液は知られていない。そこでヒドロキシアルキル化キトサンを有機溶媒に溶解させるための条件について鋭意検討した結果、本発明者らは、ヒドロキシアルキル化キトサンと有機酸またはその誘導体(以下誘導体を含めて「有機酸」と云う場合がある)とを各種非プロトン性極性溶媒に加えると、ヒドロキシアルキル化キトサンと有機酸とが相互作用してヒドロキシアルキル化キトサン溶液が得られることを見出した。
本発明に使用するヒドロキシアルキル化キトサンとしては、例えば、ヒドロキシエチルキトサン、ヒドロキシプロピルキトサン、ヒドロキシブチルキトサン、グルセリル化キトサンの如く、キトサンのアミノ基にアルキレンオキサイドやオキシランメタノールが付加した構造を有しており、キトサンとアルキレンオキサイドまたはオキシランメタノールとを反応させて製造することが好ましいが、本発明で使用するヒドロキシアルキル化キトサンはこれに限定されるものではなく、他の方法で製造されたヒドロキシアルキル化キトサンも同様に使用することができる。また、上記のアルキレンオキサイドやオキシランメタノールは単独で使用してもよいし、複数種を混合して使用してもよい。
<グリセリル化キトサンの実施例および比較例>
表1に、実施例および比較例として用いた各グリセリル化キトサン溶液の組成を示した。実施例14〜16はそれぞれ組成が同一であるが、本発明の被覆方法における条件が異なることから重複して記載してある。表中「原料キトサン1%粘度」とあるのは、グリセリル化キトサンの原料となるキトサンを1質量%含む1質量%酢酸溶液の粘度(粘度測定方法:測定温度20℃、測定回転数30rpmの条件下、ブルックフィールド型回転粘度計で測定)のことである。また、各グリセリル化キトサン溶液に使用した非プロトン性極性溶媒は、N−メチル−2−ピロリドンをNMP、N−エチル−2−ピロリドンをNEP、N,N−ジメチルホルムアミドをDMF、ジメチルスルホキシドをDMSO、N,N−ジメチルアセトアミドをDMAC、および1,3−ジメチル−2−イミダゾリジノンをDMIと略した。
NMP80質量部中にグリセリル化キトサン(原料キトサンの脱アセチル化度83%)10質量部を分散し、該分散液にサリチル酸10質量部を加えた後、室温で4時間撹拌溶解し、一晩静置後、再度室温で1時間撹拌溶解し、100質量部のグリセリル化キトサン溶液を調製した。
表1に示すように、グリセリル化キトサンの原料キトサンを1質量%含む1質量%酢酸水溶液の粘度、グリセリル化キトサンのグリセリル化度および質量、有機酸の種類および質量、グリセリル化キトサンと有機酸との配合比または非プロトン性極性溶媒の種類および質量を変えた本発明のグリセリル化キトサン溶液を、実施例1と同様の方法により調製した。また、使用した原料キトサンの脱アセチル化度は83%である。なお、グリセリル化キトサンが室温撹拌で溶解し難い場合は、加熱撹拌し溶液の調製を行った。
<比較例1>
比較例1は、グリセリル化反応を実施していないキトサン(脱アセチル化度85%、グリセリル化度0、当該キトサンを1質量%含む1質量%酢酸水溶液の粘度6mPa・s、以下単に「キトサン」という)を用いたものである。NMP90質量部にキトサン5質量部を分散し、ピロメリット酸5質量部を加えた後、室温で4時間撹拌したが溶解しなかった。そこで、NMPを80℃に加熱して2時間撹拌したがキトサンは全く溶解せず、キトサンNMP溶液を得ることはできなかった。
比較例2は、有機酸を一切使用しないで溶液を調製したものである。NMP90質量部にグリセリル化キトサン(原料キトサンの脱アセチル化度83%)10質量部を分散し、室温で4時間撹拌し、一晩静置後、再度室温で1時間撹拌溶解し、100質量部のグリセリル化キトサン溶液を調製した。
NMP90質量部にグリセリル化キトサン(原料キトサンの脱アセチル化度85%)5質量部を分散し、ピロメリット酸5質量部を加えた後、室温で4時間撹拌溶解し、一晩静置後、再度室温で1時間撹拌溶解し、100質量部のグリセリル化キトサン溶液を調製した。
脱脂処理などの前処理を一切施していないステンレス板(SUS304、板厚1mm×縦10cm×横10cm)の表面に、バーコーターを用いて実施例1〜21並びに比較例2および3の各種溶液を2g/m2の乾燥被膜量になるよう塗布し、次いで表2に示す条件で乾燥を行った。これを以下の評価試験に用いる供試材とした。
供試材を24時間純水に浸漬し、次いで105℃に調整した送風乾燥機内で1時間加熱乾燥した。室温まで放冷した後、重量測定を行い、下記に示す式より被膜残存率を求めた。
(C−A)/(B−A)×100(%)
ここで、A:各溶液を塗布する前のステンレス板の重量。
B:各溶液を塗布・乾燥後のステンレス板の重量。
C:各溶液を塗布・乾燥後、24時間水中浸漬した後、再度乾燥したステンレス板の重量である。
上記の式より得た値から、各被膜の耐水性を4段階で評価した。評価方法は以下の通りである。
◎:塗膜残存率が95%以上。
○:塗膜残存率が80%以上95%未満。
△:塗膜残存率が50%以上80%未満。
×:塗膜残存率が50%未満。
厚さ50μmのポリイミドフィルム(10cm×5cm)に対し、実施例14の5質量%グリセリル化キトサン溶液(溶液粘度:174mPa・s)をバーコーターで塗布したところ、当該NMP溶液は一切ハジキが見られず、表面疎水性のポリイミドフィルムに対し均一塗布が可能であった。
厚さ50μmのポリイミドフィルム(10cm×5cm)に対し、5質量%のキトサンを含むクエン酸5質量%水溶液(溶液粘度:186mPa・s)をバーコーターで塗布したところ、当該水溶液はハジキを発生してしまい、ポリイミドフィルムに均一に塗布することができなかった。
表3に、実施例23〜25として用いた各ヒドロキシアルキル化キトサン溶液の組成を示した。各ヒドロキシアルキル化キトサン溶液に使用した非プロトン性極性溶媒の略号も前記と同じである。なお、ヒドロキシアルキル化キトサンの製造は公知の方法に従って行った。ヒドロキシアルキル化キトサンの原料キトサンは前記実施例6と同じである。
応用例1(塗工液、電極板)
本例で用いた正極活物質を含む正極塗工液を以下の方法により作製した。正極塗工液の材料としては、1〜100μmの粒径を持つLiCoO2粉末を90質量部、導電助剤としてアセチレンブラックを5質量部、結着剤として前記表1の実施例14の溶液を50質量部の配合比で、プラネタリーミキサーにて回転数60rpmで120分間撹拌混合することによりスラリー状の正極活物質を含む正極塗工液を得た。
本例で用いた負極活物質を含む負極塗工液を以下の方法により作製した。石炭コークスを1,200℃で熱分解させて得られるカーボン粉末を90質量部、導電補助剤としてのアセチレンブラック5質量部および前記実施例8の溶液50質量部の配合比で、プラネタリーミキサーにて回転数60rpmで120分間撹拌混合させてスラリー状の負極活物質含有塗工液を得た。
以上で得られた応用例1の正極板および応用例2の負極板を用い、正極板より幅広の三次元空孔構造(海綿状)を有するポリオレフィン系(ポリプロピレン、ポリエチレンまたはそれらの共重合体)の多孔性フィルムからなるセパレータを介して、渦巻き状に捲回して、先ず電極体を構成した。次にこの電極体を、負極端子を兼ねる有底円筒状のステンレス容器内に挿入し、AAサイズで定格容量500mAhの電池を組み立てた。この電池にEC(エチレンカーボネート):PC(プロピレンカーボネート):DME(ジメトキシエタン)をそれぞれ体積比1:1:2で全量1リットルになるように調製した混合溶媒に、支持塩として1モルのLiPF6を溶解したものを電解液として注液した。
Claims (10)
- 非プロトン性極性溶媒中にヒドロキシアルキル化キトサンと有機酸またはその誘導体とを含むことを特徴とするヒドロキシアルキル化キトサン溶液。
- 非プロトン性極性溶媒が、N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N−メチル−2−ピロリドン、N−エチル−2−ピロリドン、1,3−ジメチル−2−イミダゾリジノンおよびジメチルスルホキシドからなる群から選ばれる少なくとも1種である請求項1に記載のヒドロキシアルキル化キトサン溶液。
- 有機酸が、多塩基酸である請求項1に記載のヒドロキシアルキル化キトサン溶液。
- 多塩基酸が、ピロメリット酸、クエン酸、トリメリット酸、リンゴ酸、ポリマレイン酸、フタル酸、およびコハク酸からなる群から選ばれる少なくとも1種である請求項3に記載のヒドロキシアルキル化キトサン溶液。
- 有機酸またはその誘導体の使用量が、ヒドロキシアルキル化キトサン100質量部当たり20〜300質量部である請求項1に記載のヒドロキシアルキル化キトサン溶液。
- ヒドロキシアルキル化キトサンの濃度が、1〜40質量%である請求項1に記載のヒドロキシアルキル化キトサン溶液。
- ヒドロキシアルキル化キトサンのヒドロキシアルキル化度が、0.2以上である請求項1に記載のヒドロキシアルキル化キトサン溶液。
- ヒドロキシアルキル化キトサンが、脱アセチル化度が30%以上かつ1質量%酢酸水溶液に1質量%の濃度で溶解したときの該溶液の粘度が1mPa・s〜10,000mPa・sであるキトサンのヒドロキシアルキル化物である請求項1に記載のヒドロキシアルキル化キトサン溶液。
- 請求項1〜8のいずれか1項に記載のヒドロキシアルキル化キトサン溶液を基材の表面に付着させる工程、および該工程で得られた基材を100℃以上で1秒間以上加熱する工程を包含することを特徴とする基材の被覆方法。
- ヒドロキシアルキル化キトサン溶液が、有機または無機粒子を含み、基材が金属性物品である請求項9に記載の基材の被覆方法。
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EP06834947.1A EP1978056B1 (en) | 2006-01-25 | 2006-12-19 | Hydroxyalkylated chitosan solution |
KR1020087018228A KR100984439B1 (ko) | 2006-01-25 | 2006-12-19 | 히드록시알킬화 키토산 용액 |
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PCT/JP2006/325237 WO2007086211A1 (ja) | 2006-01-25 | 2006-12-19 | ヒドロキシアルキル化キトサン溶液 |
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EP (1) | EP1978056B1 (ja) |
JP (1) | JP4866173B2 (ja) |
KR (1) | KR100984439B1 (ja) |
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- 2006-12-19 KR KR1020087018228A patent/KR100984439B1/ko active IP Right Grant
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Also Published As
Publication number | Publication date |
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EP1978056B1 (en) | 2015-10-07 |
WO2007086211A1 (ja) | 2007-08-02 |
KR20080087136A (ko) | 2008-09-30 |
CN101336272B (zh) | 2011-01-19 |
CN101336272A (zh) | 2008-12-31 |
KR100984439B1 (ko) | 2010-09-29 |
EP1978056A4 (en) | 2013-05-01 |
JP4866173B2 (ja) | 2012-02-01 |
US20100291306A1 (en) | 2010-11-18 |
US8133541B2 (en) | 2012-03-13 |
EP1978056A1 (en) | 2008-10-08 |
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