Novel paper sizing agents based on renewables. Part 5: characterization of maleated oleates by ozonolysis

Holzforschung ◽  
2012 ◽  
Vol 66 (1) ◽  
Author(s):  
Elisabeth Lackinger ◽  
Jürgen Sartori ◽  
Antje Potthast ◽  
Thomas Rosenau
Keyword(s):  
Oleic Acid ◽  
Double Bond ◽  
Structural Analysis ◽  
Molecular Fragments ◽  
Acid Moiety ◽  
High Oleic Sunflower Oil ◽  
High Oleic ◽  
Paper Sizing ◽  
Sizing Agents

Abstract Maleated high oleic sunflower oil (maleated SOHO, MSOHO) is a promising substitute for alkenyl succinic anhydrides (ASA) that are widely used as sizing agents for paper. The part of the MSOHO molecule that is believed to be responsible for adhesion of the molecule onto cellulose, i.e., the maleated oleic acid moiety, was separately prepared and analytically characterized. Structural analysis was completed by studies of the molecular fragments obtained upon ozonolysis. The interesting question of whether there was a preferential reactivity during the ene-reaction of maleic anhydride with oleates was answered in a way that the newly formed double bond was placed to either side with no apparent selectivity.

Novel paper sizing agents from renewables. Part 2: Characterization of maleated high oleic sunflower oil (MSOHO)

Holzforschung ◽  
2011 ◽  
Vol 65 (1) ◽  
pp. 13-19 ◽  
Author(s):  
Elisabeth Lackinger ◽  
Leo Schmid ◽  
Jürgen Sartori ◽  
Akira Isogai ◽  
Antje Potthast ◽  
...  
Keyword(s):  
Sunflower Oil ◽  
Total Reflection ◽  
Attenuated Total Reflection ◽  
Resonance Spectroscopy ◽  
High Oleic Sunflower Oil ◽  
High Oleic ◽  
Alkenyl Succinic Anhydride ◽  
Paper Sizing ◽  
Sizing Agents

Abstract Maleated oils derived from high oleic sunflower oil (MSOHO) have promising applications in paper sizing as a green alternative to conventional reactive sizing agents, such as alkenyl succinic anhydride. In this study, MSOHO was comprehensively characterized analytically by attenuated total reflection infrared spectroscopy, 1H and 13C nuclear magnetic resonance spectroscopy with full resonance assignment, and mass spectrometry.

Novel Paper Sizing Agents Based on Renewables. Part 6: Sizing Properties of Maleated High Oleic Sunflower Oil

2012 ◽  
Vol 32 (1) ◽  
pp. 51-65 ◽  
Author(s):  
Elisabeth Lackinger ◽  
Johannes Fallmann ◽  
Jürgen Sartori ◽  
Antje Potthast ◽  
Thomas Rosenau
Keyword(s):  
Sunflower Oil ◽  
High Oleic Sunflower Oil ◽  
High Oleic ◽  
Paper Sizing ◽  
Sizing Agents

Novel paper sizing agents based on renewables. Part 4: Application properties in comparison to conventional ASA sizes

Holzforschung ◽  
2011 ◽  
Vol 65 (2) ◽  
Author(s):  
Elisabeth Lackinger ◽  
Leo Schmid ◽  
Jürgen Sartori ◽  
Antje Potthast ◽  
Thomas Rosenau
Keyword(s):  
Water Molecules ◽  
The Novel ◽  
Practical Application ◽  
High Oleic Sunflower Oil ◽  
High Oleic ◽  
Anhydride Group ◽  
Alkenyl Succinic Anhydride ◽  
Paper Sizing ◽  
Reaction With Water ◽  
Sizing Agents

Abstract Reactive paper sizing agents, such as alkenyl succinic anhydride (ASA), provide hydrophobicity to paper. The reactive anhydride group of these reagents is highly susceptible to reaction with water and thus resistance against hydrolysis is of primary importance for their practical application. This study describes different application-relevant properties of recently developed sizing agents that are based on renewable vegetable oils including hydrolysis behavior, time-dependent sizing efficiency, and tendency to form deposits or foam. The novel sizing agents – maleated high oleic sunflower oil (MSOHO) and maleated rapeseed oil (MRSO) – are compared to conventional ASA as the state-of-the-art sizing agent. Although the reactive group is the same in all reagents, there are pronounced differences between the three reagents, with MSOHO showing the best performance, i.e., the slowest hydrolysis. This oil has a higher ratio of hydrophobic side chains that impede the water attack at the anhydride group. Also, the higher viscosity of MSOHO plays an important role in performance, because diffusion of water molecules into a MSOHO emulsion droplet is much slower than in the case of conventional ASA.

Selection and Molecular Characterization of Soybeans with High Oleic Acid from Plant Germplasm of Genebank

2019 ◽  
Vol 22 (4) ◽  
pp. 323-333
Author(s):  
Kyung Jun Lee ◽  
Jung-Ro Lee ◽  
Myoung-Jae Shin ◽  
Gyu-Taek Cho ◽  
Kyung-Ho Ma ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Molecular Characterization ◽  
High Oleic Acid ◽  
High Oleic ◽  
Plant Germplasm

Novel paper sizing agents from renewables. Part 3: Emulsion stability and hydrolysis behavior compared to conventional sizes

Holzforschung ◽  
2011 ◽  
Vol 65 (1) ◽  
pp. 21-27 ◽  
Author(s):  
Elisabeth Lackinger ◽  
Akira Isogai ◽  
Leo Schmid ◽  
Jürgen Sartori ◽  
Antje Potthast ◽  
...  
Keyword(s):  
Hydrolytic Stability ◽  
Water Repellency ◽  
Commercial Sample ◽  
Agent Based ◽  
High Oleic ◽  
Alkenyl Succinic Anhydride ◽  
Paper Sizing ◽  
Ph Conditions ◽  
Sizing Agents ◽  
Positive Effect

Abstract The hydrolytic stability and sizing behavior of a new paper sizing agent based on renewable vegetable oils (maleated sunflower oil, high oleic: MSOHO) was compared to two conventional alkenyl succinic anhydride (ASA) specimens, a commercial sample, and a reagent-grade ASA sample. At various pH conditions as well as upon addition of Ca2+ ions, MSOHO was more stable than both ASA samples. This superior stability of MSOHO was also supported by zeta potential measurements over 1 week. Whereas for sizing of paper higher dosages of MSOHO were needed to gain certain water repellency as compared to the ASA samples, the addition of alum had a pronounced positive effect on the sizing efficiency of MSOHO. The higher stability of MSOHO made it possible to size with an MSOHO-starch emulsion that was aged for one day at room temperature, when conventional ASA-starch emulsion had long lost any sizing efficiency.

Novel paper sizing agents from renewables. Part 1: Preparation of a paper sizing agent derived from natural plant oils

Holzforschung ◽  
2011 ◽  
Vol 65 (1) ◽  
pp. 3-11 ◽  
Author(s):  
Elisabeth Lackinger ◽  
Leo Schmid ◽  
Jürgen Sartori ◽  
Akira Isogai ◽  
Antje Potthast ◽  
...  
Keyword(s):  
Oleic Acid ◽  
Fatty Acid ◽  
Maleic Anhydride ◽  
Plant Oils ◽  
Natural Plant ◽  
Natural Oils ◽  
Paper Sizing ◽  
Sizing Agents ◽  
Product Viscosity ◽  
Increased Pressure

Abstract Natural oils derived from linseed, rapeseed, soybean, and a special breed of sunflower were tested for the production of maleated fatty oils for paper sizing in the ene-reaction with maleic anhydride. All these maleated oils were subjected to a conventional sizing test proving their ability to hydrophobize handsheets. Natural oils having only monounsaturated fatty acid residues (oleic acid) in the triglycerides worked best by having lower product viscosity and higher yields. The optimized production procedure employs antioxidant addition, an increased maleic anhydride:triglyceride ratio of 4:1, as well as increased pressure to reduce undesired polymeric byproducts and to increase yield.

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