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Title: Lignin poly(lactic acid) copolymers

Abstract

Provided herein are graft co-polymers of lignin and poly(lactic acid) (lignin-g-PLA copolymer), thermoset and thermoplastic polymers including them, methods of preparing these polymers, and articles of manufacture including such polymers.

Inventors:
; ; ; ; ; ;
Publication Date:
Research Org.:
The Board of Trustees of the Leland Stanford Junior University, Stanford, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1343766
Patent Number(s):
9,567,432
Application Number:
13/975,101
Assignee:
The Board of Trustees of the Leland Stanford Junior University CHO
DOE Contract Number:
SC0005430
Resource Type:
Patent
Resource Relation:
Patent File Date: 2013 Aug 23
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE

Citation Formats

Olsson, Johan Vilhelm, Chung, Yi-Lin, Li, Russell Jingxian, Waymouth, Robert, Sattely, Elizabeth, Billington, Sarah, and Frank, Curtis W. Lignin poly(lactic acid) copolymers. United States: N. p., 2017. Web.
Olsson, Johan Vilhelm, Chung, Yi-Lin, Li, Russell Jingxian, Waymouth, Robert, Sattely, Elizabeth, Billington, Sarah, & Frank, Curtis W. Lignin poly(lactic acid) copolymers. United States.
Olsson, Johan Vilhelm, Chung, Yi-Lin, Li, Russell Jingxian, Waymouth, Robert, Sattely, Elizabeth, Billington, Sarah, and Frank, Curtis W. Tue . "Lignin poly(lactic acid) copolymers". United States. doi:. https://www.osti.gov/servlets/purl/1343766.
@article{osti_1343766,
title = {Lignin poly(lactic acid) copolymers},
author = {Olsson, Johan Vilhelm and Chung, Yi-Lin and Li, Russell Jingxian and Waymouth, Robert and Sattely, Elizabeth and Billington, Sarah and Frank, Curtis W.},
abstractNote = {Provided herein are graft co-polymers of lignin and poly(lactic acid) (lignin-g-PLA copolymer), thermoset and thermoplastic polymers including them, methods of preparing these polymers, and articles of manufacture including such polymers.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Feb 14 00:00:00 EST 2017},
month = {Tue Feb 14 00:00:00 EST 2017}
}

Patent:

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  • Air–water interfacial monolayers of poly((d,l-lactic acid-ran-glycolic acid)-block-ethylene glycol) (PLGA–PEG) exhibit an exponential increase in surface pressure under high monolayer compression. In order to understand the molecular origin of this behavior, a combined experimental and theoretical investigation (including surface pressure–area isotherm, X-ray reflectivity (XR) and interfacial rheological measurements, and a self-consistent field (SCF) theoretical analysis) was performed on air–water monolayers formed by a PLGA–PEG diblock copolymer and also by a nonglassy analogue of this diblock copolymer, poly((d,l-lactic acid-ran-glycolic acid-ran-caprolactone)-block-ethylene glycol) (PLGACL–PEG). The combined results of this study show that the two mechanisms, i.e., the glass transition of the collapsed PLGA filmmore » and the lateral repulsion of the PEG brush chains that occur simultaneously under lateral compression of the monolayer, are both responsible for the observed PLGA–PEG isotherm behavior. Upon cessation of compression, the high surface pressure of the PLGA–PEG monolayer typically relaxes over time with a stretched exponential decay, suggesting that in this diblock copolymer situation, the hydrophobic domain formed by the PLGA blocks undergoes glass transition in the high lateral compression state, analogously to the PLGA homopolymer monolayer. In the high PEG grafting density regime, the contribution of the PEG brush chains to the high monolayer surface pressure is significantly lower than what is predicted by the SCF model because of the many-body attraction among PEG segments (referred to in the literature as the “n-cluster” effects). The end-grafted PEG chains were found to be protein resistant even under the influence of the “n-cluster” effects.« less
  • Lactic acid has been an intermediate-volume specialty chemical (world production {approximately}40,000 tons/yr) used in a wide range of food processing and industrial applications. lactic acid h,as the potential of becoming a very large volume, commodity-chemical intermediate produced from renewable carbohydrates for use as feedstocks for biodegradable polymers, oxygenated chemicals, plant growth regulators, environmentally friendly ``green`` solvents, and specially chemical intermediates. In the past, efficient and economical technologies for the recovery and purification of lactic acid from crude fermentation broths and the conversion of tactic acid to the chemical or polymer intermediates had been the key technology impediments and main processmore » cost centers. The development and deployment of novel separations technologies, such as electrodialysis (ED) with bipolar membranes, extractive distillations integrated with fermentation, and chemical conversion, can enable low-cost production with continuous processes in large-scale operations. The use of bipolar ED can virtually eliminate the salt or gypsum waste produced in the current lactic acid processes. In this paper, the recent technical advances in tactic and polylactic acid processes are discussed. The economic potential and manufacturing cost estimates of several products and process options are presented. The technical accomplishments at Argonne National Laboratory (ANL) and the future directions of this program at ANL are discussed.« less
  • Poly(lactic acid) [PLA] was melt blended with polyethylene(oxide) [PEG] and poly(ethylene glycol) [PEG] in different compositions to form blown films. It was determined that PLA was miscible with PEO in all compositions. Based on Gordon-Taylor equation, it was determined that the interactions between PLA and PEO is stronger than PEG. The addition of low molecular weight PEG improved the elongation and tear strength of the blends. Enzymatic degradation results shows that the weight loss of all the samples was more than 80% of the initial weight in 48 hours.
  • The ternary blends of poly(lactic acid) (PLA), poly(ethylene-co-vinyl alcohol) (EVOH), and poly(ethylene-co-glycidyl methacrylate) (EGMA) were prepared. The role of EGMA as a compatibilizer was evaluated. The weight ratio of PLA:EVOH was 80:20 and the EGMA loadings were varied from 5-20 phr. The blends were characterized as follows: thermal properties by differential scanning calorimetry, morphology by scanning electron microscopy, and mechanical properties by pendulum impact tester, and universal testing machine. The glass transition temperature of PLA blends did not change much when compared with that of PLA. The blends of PLA/EGMA and EVOH/EGMA showed EGMA dispersed droplets where the latter ledmore » to poor impact properties. However, the tensile elongation at break and tensile toughness substantially increased upon addition of EGMA to blends of PLA and EVOH. It was noted in tensile test samples that both PLA and EVOH domains fibrillated significantly to produce toughness.« less
  • This paper discusses a method for recovering oil from subterranean wells. It comprises dispersing a positively-charged soluble graft copolymer of lignin with a neutralizing anion in injection water; injecting the dispersion into the subterranean formation; and moving the injection fluid through the formation as a hydraulic ram, thereby pushing the resident oil to a production well.