Tech Alerts-September 2023

Technical News,

[HTML]Thermal stability of levopimaric acid and its oxidation products

Y Li, H Chen, H Yan, Y Xu, J Tang, R Wang, M Yan… - BMC chemistry, 2023

… Gumrosin is produced at an estimated 1,200,000 tonnes per year worldwide, and 
its use as a raw industrial material has been widespread. Levopimaric acid, however, 
presents a tricky challenge to use in applications: the conjugated linkages in the …

Of academic interest since LPA isn’t a significant part of gum or tall oil rosin.

 

[PDF]Industrial Fragrance Chemistry: A Brief Historical Perspective

ORP David, F Doro - European Journal of Organic Chemistry

Perfumery has evolved from a handcraft activity, marking supreme aristocratic luxury 
in the Renaissance, to a global industry powering scent experiences for presentday 
consumers through the use of a myriad of consumer packaged goods. This …

Fascinating and comprehensive of the history of synthetic fragrance chemicals – a significant portion of the pine chemicals industry. Well worth reading.

 

 

[PDF]Biorefineries in Kraft pulp mills for biofuels production: A critical review

LFL Luz-Junior, CN Avila-Neto

… [109] This approach was successfully tested with talloilfatty acids, methanol, and 
hydrogen, in the presence of Cu-based SiO2-Al2O3-supported catalysts at 30–32atm 
and 453K. The results proved that the one-step process is capable of reducing the 

A useful paper with a lot of background.

 

 

[HTML]Followup of the reevaluation of glycerol esters of wood rosins (E 445) as a food additive

M Younes, G Aquilina, G Degen, KH Engel, P Fowler… - EFSA Journal, 2023

… Excluded from these specifications are substances derived from gumrosin, and 
exudate of living pine trees, and substances derived from tall oil rosin, a byproduct 
of kraft (paper) pulp processing. The final product is composed of ~ 90% resin acids …

An important study concerning the European food regulations for wood rosin glycerol ester – the only one allowed. 

 

 

 

 

 

 

 

HEAVY DUTY TIRE

European Patent EP3800220 B1 · Filed: 09/10/2020 · Published: 08/23/2023

Assignee:

SUMITOMO RUBBER IND (JP)

Inventors:

KASEI YUKI (JP)

The performance of rubber tires on ice and abrasion resistance are inversely related, meaning it is difficult to accomplish concurrently.  This is highly desired in heavy duty tires.  This patent claims tires and tire treads rubbers where the preferred resin is alpha-pinene or has a large percentage of alpha-pinene.  Other tackifiers work but apparently not like alpha-pinene. Terpene-phenol resins and aromatic modified resins work but not like pure alpha-pinene resins.  Rosin resins work also but not like alpha-pinene.

 

 

TREAD RUBBER COMPOSITION AND PNEUMATIC TIRE

European Patent EP3851488 B1 · Filed: 10/01/2019 · Published: 08/09/2023

Assignee:

SUMITOMO RUBBER IND (Kobe-shi, Hyogo 651-0072, JP)

Inventors:

TOMITA KOTA (JP)
SAKAGUCHI YUMI (JP)

This patent also from Sumitomo claims tire rubber compositions that are very good on dry roads.  In this case performance is good with aromatic modified resins and very good with alpha-pinene.  This technology looks like the previous patent on the surface, but it has a lot of differences compared to the previous patent.  The lesson from these two patents is that tire rubber technology is so dependent on polymers, resins, fillers, oils (if they’re used), the roads (huge number of variables) and the like that there might never be a useful one size fits all theory for tires.  However, based on my observations of tire rubber technology, using resins heavy with alpha-pinene is a correct thing to do much of the time.

 

 

METHOD OF TREATING CITRUS GREENING

European Patent EP3742899 B1 · Filed: 01/17/2019 · Published: 08/30/2023

Assignee:

Greening Be Gone, LLC (Fredericksburg VA 22401, US)

Inventors:

Eveland, Winsor Gebhard (Englewood, FL 34224, US)
Brown, Kenneth Earl (Fredericksburg, VA 22401, US)

It has been discovered that a composition that contains at least citrus oil, pine oil, and salt water is effective in mitigating or eliminating detrimental microbials including, in one example, gram-negative bacteria disease in plants. This mixture is effective as an antimicrobial including against citrus greening and other gram-negative bacteria diseases.

“This patent claims very economical and effective compositions based on terpenes for treating very serious, damaging bacteria that destroy citrus plants.” One of our PCA members was actively pursuing this use.

 

 

PRODUCTION OF AN EXTRACT OF PHYTOSTEROLS AND STANOLS FROM TALL OIL PITCH

European Patent EP4025676 B1 · Filed: 09/02/2020 · Published: 08/02/2023

Assignee:

PINE CHEMICAL HOLDING S A (1251 Luxembourg, LU)

Inventors:

TSEBULAEV VICTOR (LU)
KHODOV NIKOLAY (LU)
RADBIL ARKADY (RU)
DOLINSKI TARAS (RU)
KORSHUNOV ALEXEY (RU)
CHERNOV ILYA (RU)
LAZAREV MIKHAIL (RU)

This patent claims another process for recovering sterols from tall oil pitch.  I’ll leave this one for the experts to read and analyze.

 

 

Method to prepare an aviation fuel component

United States Patent 11718800 B2 · Filed: 11/23/2020 · Published: 08/08/2023

Assignee:

Neste Oyj (Espoo, FI)

Inventors:

Kiiski, Ulla (Porvoo, FI)
Likander, Salla (Porvoo, FI)
Sandberg, Kati (Porvoo, FI)
Saikkonen, Pirjo (Porvoo, FI)

This is a new method to produce aviation fuel using mixtures of fossil and biorenewable feeds (mostly tall oil pitch).  However, there is no discussion (that I could see) about qualities such as heat yields, rates of combustion and greenhouse gas emissions.  It’s hard to know what this process really provides.

 

 

Asphalt emulsion surface treatment containing sterol

United States Patent 11718756 B2 · Filed: 10/11/2018 · Published: 08/08/2023

Assignee:

A.L.M. Holding Company (Onalaska, WI, US)
Ergon Asphalt & Emulsions, Inc. (Jackson, MS, US)

Inventors:

Reinke, Gerald H. (La Crosse, WI, US)
Baumgardner, Gaylon L. (Arkadelphia, AR, US)
Hanz, Andrew (LaCrosse, WI, US)

This patent claims that the use of sterols in asphalt retards the oxidation and other age related changes that befall asphalt.  I wonder how they decided to examine the effect of sterols on asphalt.

This part is dated September 30, 2023)

 

 

Low volatile tackifier compositions

United States Patent 11753566 B2 · Filed: 01/29/2020 · Published: 09/12/2023

Assignee:

Synthomer Adhesive Technologies LLC (Beachwood, OH, US)

Inventors:

Yuan, Bing (Methuen, MA, US)
Dickerson, James Palmer (Kingsport, TN, US)
Liew, Bee Kim (Kingsport, TN, US)
Osborne, Christopher Wayne (Johnson City, TN, US)
Siera, Jacobus (Hoogerheide, NL)

This is another patent claiming tackifier compositions with very low levels of volatile organics due to different methods of distillation of the resins.

 

 

IMPROVED CONDUCTIVE INK COMPOSITIONS

WIPO Patent Application WO/2023/168452 A2 · Filed: 03/05/2023 · Published: 09/07/2023

Assignee:

ELECTRONINKS INCORPORATED (US)

Inventors:

WALKER S BRETT (US)
LEMIEUX MELBURNE (US)
PERERA K L IRESHA SAMPATHI (US)
MCKERRICHER GARRET (US)
CHERTAKOVSKY RON (US)
LEE SCOTT SOUNG JAE (US)

This patent claims unique conductive inks where terpenes, hydrocarbons and alcohols play key roles in their preparation.  The present disclosure relates generally to novel conductive ink compositions and their methods of preparation and use. More particularly, the present disclosure relates to improved particle-free ink compositions comprising silver carboxylates that form conductive structures at low temperature.  Silver decanoate appears to be unique in its effectiveness. Pinenes, limonene, and terpineols are specified as excellent solvents.

 

 

RUBBER COMPOSITION AND TIRE CONTAINING VEGETABLE OIL EXTENDED STYRENE/BUTADIENE ELASTOMER AND RESIN

European Patent EP4000956 B1 · Filed: 11/10/2021 · Published: 09/13/2023

Assignee:

GOODYEAR TIRE & RUBBER (Akron, OH 44316, US)

Inventors:

GERSMAN MICHAEL LAWRENCE (US)
ISITMAN NIHAT ALI (US)
YOUNG PHILIP JORDAN (US)

This patent discloses the use of triglyceride oils to extend relatively high Tg polymers, in contrast to adding petroleum oils to very high Tg polymers (usually made by emulsion polymerization) to be used in tire treads.  These extended polymers could be used in tires now.

Opaque water-based inks

United States Patent 11753556 B2 · Filed: 04/25/2018 · Published: 09/12/2023

Assignee:

SUN CHEMICAL CORPORATION (Parsippany, NJ, US)

Inventors:

Lahr, Alexander (Rock Hill, SC, US)
Marshall, Bruce (Fort Mill, SC, US)

Described herein are opaque water-based inks that include water and an opacity-providing polymer component. In one aspect, the opacity providing polymer component is a hollow sphere polymer material. The opacity-providing polymer material may replace all or part of white opacifying pigment material, such as titanium dioxide. Also described herein is a method of opacifying a printing ink by adding hollow sphere resin particles and a colorant to a printing ink that comprises water as a volatile component.  

Very interesting technology.

 

 

Method for identifying the extent of aging in an asphalt

United States Patent 11760882 B2 · Filed: 11/08/2021 · Published: 09/19/2023

Assignee:

A.L.M. Holding Co. (Onalaska, WI, US)
Ergon Asphalt & Emulsions, Inc. (Jackson, MS, US)

Inventors:

Reinke, Gerald H. (La Crosse, WI, US)
Baumgardner, Gaylon L. (Arkadelphia, AR, US)
Hanz, Andrew (La Crosse, WI, US)

Disclosed are asphalt and asphalt binders and methods for making such compositions with sterols. The sterols improve various rheological properties. Also disclosed are methods of determining the changes or improvements of various rheoloical properties.

Note the use of sterols for enhancing the performance of asphalt.

 


Courtesy of Kerry Thompson, Nelson Lawson, and the PCA.