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Synthesis, stereocomplex crystallization and homo-crystallization of enantiomeric poly(lactic acid-co-alanine)s with ester and amide linkages†
Polymer Chemistry ( IF 4.1 ) Pub Date : 2017-12-28 00:00:00 , DOI: 10.1039/c7py02024d Hideto Tsuji 1, 2, 3, 4, 5 , Shotaro Sato 6, 7, 8, 9, 10 , Noriaki Masaki 1, 2, 3, 4, 5 , Yuki Arakawa 1, 2, 3, 4, 5 , Akinori Kuzuya 6, 7, 8, 9, 10 , Yuichi Ohya 6, 7, 8, 9, 10
Polymer Chemistry ( IF 4.1 ) Pub Date : 2017-12-28 00:00:00 , DOI: 10.1039/c7py02024d Hideto Tsuji 1, 2, 3, 4, 5 , Shotaro Sato 6, 7, 8, 9, 10 , Noriaki Masaki 1, 2, 3, 4, 5 , Yuki Arakawa 1, 2, 3, 4, 5 , Akinori Kuzuya 6, 7, 8, 9, 10 , Yuichi Ohya 6, 7, 8, 9, 10
Affiliation
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α-Hydroxy acid and α-amino acid-derived poly(L-lactic acid-co-L-alanine)s and poly(D-lactic acid-co-D-alanine)s with different alanine unit contents were synthesized by copolymerization of L-lactide and (3S,6S)-3,6-dimethyl-morpholine-2,5-dione and of D-lactide and (3R,6R)-3,6-dimethyl-morpholine-2,5-dione, respectively. The effects of the incorporated alanine units in lactic acid units or amide linkages in ester linkages on the crystallization behavior of solution- and melt-crystallized 50/50 blended samples as well as that of solution- and melt-crystallized nonblended samples were investigated. This article reports for the first time a stereocomplex (SC) formation between enantiomeric random copolyesteramides poly(lactic acid-co-alanine)s with ester and amide linkages. The solution-crystallized nonblended samples crystallized in α- or δ-form homo-crystallites for an L-alanine unit content up to 6 mol% or a D-alanine unit content up to 3 mol%, whereas all the melt-crystallized samples crystallized in α- or δ-form homo-crystallites for the L- or D-alanine unit content at least up to 12 and 13 mol%. In contrast, the solution-crystallized blended samples with the alanine unit contents of 0–13 mol% and the melt-crystallized blended samples with the alanine unit contents of 4–13 mol% crystallized only in SC crystallites, whereas the melt-crystallized blended samples with an alanine unit content of 0 mol% [i.e., poly(L-lactic acid)/poly(D-lactic acid) blends] crystallized in both SC crystallites and homo-crystallites. The alanine units of melt-crystallized nonblended samples were incorporated into homo-crystalline regions, whereas those of solution-crystallized nonblended samples were excluded from homo-crystalline regions. In contrast, the alanine units of solution-crystallized blended samples were incorporated into SC crystalline regions, whereas those of melt-crystallized blended samples were excluded from SC crystalline regions.
中文翻译：
合成，立体络合物结晶和对映体的聚同型结晶（乳酸-共-丙氨酸）s的酯和酰胺键†
α羟基酸和α -氨基酸衍生的聚（大号-乳酸酸共-大号丙氨酸）和聚（d -乳酸酸共- d -丙氨酸）■通过共聚合成不同丙氨酸单元内容L-丙交酯和（3 S，6 S）-3,6-二甲基吗啉-2,5-二酮和D-丙交酯和（3 R，6 R）-3,6-二甲基吗啉-2,5-二酮。研究了掺入乳酸单元中的丙氨酸单元或酯键中的酰胺键对溶液和熔融结晶的50/50混合样品以及溶液和熔融结晶的非共混样品的结晶行为的影响。这是第一次对映体无规共聚酯酰胺之间的立体络合物（SC）的形成聚（乳酸-文章报道共丙氨酸）s的酯和酰胺键。溶液结晶的非共混物，结晶成α-或δ-均晶，L-丙氨酸单元含量最高为6 mol％或D-丙氨酸单元的含量最高为3mol％，而所有以L-或D-丙氨酸单元的α-或δ-型均晶结晶的熔融结晶样品的含量至少为12和13mol％。相比之下，丙氨酸单位含量为0–13 mol％的固溶混合样品和丙氨酸单位含量为4–13 mol％的熔融结晶混合样品仅在SC微晶中结晶，而熔融结晶混合样品丙氨酸单位含量为0 mol％的样品[即聚（L-乳酸）/聚（D-乳酸）共混物]在SC微晶和均晶中均结晶。将熔融结晶的非共混样品的丙氨酸单元并入均晶区域，而溶液结晶的非共混样品的丙氨酸单元从均晶区域中排除。相反，将溶液结晶混合样品的丙氨酸单元并入SC结晶区域，而将熔融结晶混合样品的丙氨酸单元排除在SC结晶区域之外。
更新日期：2017-12-28
中文翻译：
合成，立体络合物结晶和对映体的聚同型结晶（乳酸-共-丙氨酸）s的酯和酰胺键†
α羟基酸和α -氨基酸衍生的聚（大号-乳酸酸共-大号丙氨酸）和聚（d -乳酸酸共- d -丙氨酸）■通过共聚合成不同丙氨酸单元内容L-丙交酯和（3 S，6 S）-3,6-二甲基吗啉-2,5-二酮和D-丙交酯和（3 R，6 R）-3,6-二甲基吗啉-2,5-二酮。研究了掺入乳酸单元中的丙氨酸单元或酯键中的酰胺键对溶液和熔融结晶的50/50混合样品以及溶液和熔融结晶的非共混样品的结晶行为的影响。这是第一次对映体无规共聚酯酰胺之间的立体络合物（SC）的形成聚（乳酸-文章报道共丙氨酸）s的酯和酰胺键。溶液结晶的非共混物，结晶成α-或δ-均晶，L-丙氨酸单元含量最高为6 mol％或D-丙氨酸单元的含量最高为3mol％，而所有以L-或D-丙氨酸单元的α-或δ-型均晶结晶的熔融结晶样品的含量至少为12和13mol％。相比之下，丙氨酸单位含量为0–13 mol％的固溶混合样品和丙氨酸单位含量为4–13 mol％的熔融结晶混合样品仅在SC微晶中结晶，而熔融结晶混合样品丙氨酸单位含量为0 mol％的样品[即聚（L-乳酸）/聚（D-乳酸）共混物]在SC微晶和均晶中均结晶。将熔融结晶的非共混样品的丙氨酸单元并入均晶区域，而溶液结晶的非共混样品的丙氨酸单元从均晶区域中排除。相反，将溶液结晶混合样品的丙氨酸单元并入SC结晶区域，而将熔融结晶混合样品的丙氨酸单元排除在SC结晶区域之外。
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