IP Library Granted Patent US 11,001,727
Granted Patent B2
US 11,001,727 · App. 15/794,093 · Granted May 11, 2021

Renewable, biodegradable marking wax composition

Inventors: Rob Falken (Carlsbad, CA); Adam Johnson (Bainbridge, GA); Rachelle Arnold (Bainbridge, GA); Phillip Van Trump (Decatur, GA)
Assignees: Danimer Bioplastics, Inc.; Tecniq Holdings, LLC
C09D13/00C08K5/09C08L67/02C11C3/00
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Quick Facts
Patent No.
US 11,001,727
App. No.
15/794,093
Granted
May 11, 2021
Kind
B2
Abstract

The present disclosure is directed to marking compositions that are derived from environmentally friendly, biodegradable, and sustainable resources. Such compositions may be formulated in to writing and/or drawing instruments such as crayons. In various embodiments, the marking compositions include one or more of a structural component, a stiffening and/or laydown component, and a colorant. For instance, the structural component may be an ester wax composed of a diol and diacid, such as where the diols and diacids contain about 2 to about 14 carbon atoms each, such as where the structural component is present in an amount of from about 10% by weight to about 90% by weight, such as about 20% to about 80%, including about 60% of the composition. Additionally, the stiffening and/or lay down component may be a bifunctional fatty acid, such as stearic acid, which may be included in the composition, such as a stiffening agent as well as to enhance smoothness of laydown. A typically useful amount that may be used ranges from about 20% or less to about 80% or more, such as about 40% to 60% or more by weight of the composition. Further, in various embodiments, a naturally occurring, organic colorant may be provided as part of the marking composition.

Claims (35)

1. A marking composition comprising:

a condensation polymer which is a reaction product of a diol and a dicarboxylic acid, in an amount from about 10% to about 90% by weight of the composition;

one or more fatty acids containing from 10 to 24 carbon atoms, or an ester thereof, in an amount from about 20% to about 80% by weight of the composition; and

a colorant, in an amount from about 1% to about 15% by weight of the composition,

wherein the polymer has a Shore D hardness value from 35 to 65, and

wherein the condensation polymer has a weight average molecular weight of from about 5000 to about 15,000 daltons and is selected from the group consisting of poly(butylene adipate), poly(hexylene succinate), and poly(propylene adipate).

2. The marking composition of claim 1 , wherein the polymer comprises from about 20% to about 80% by eight of the composition.

3. The marking composition of claim 1 , wherein the diol and the dicarboxylic acid each contain 2 to 14 carbon atoms.

4. The marking composition of claim 1 , wherein the polymer has a melting point from about 40 C to about 75 C.

5. The marking composition of claim 1 , wherein the composition comprises one or more fatty acids containing from 14 to 18 carbon atoms, or an ester thereof, in an amount from about 20% to about 80% by weight of the composition.

6. The marking composition of claim 1 , wherein the one or more fatty acids comprise are fully saturated fatty acids.

7. The marking composition of claim 1 , wherein the one or more fatty acids have a weight average molecular weight of from about 100 to about 400 daltons.

8. The marking composition of claim 1 , wherein the colorant is an inorganic pigment.

9. The marking composition of claim 1 , wherein the colorant is a pigment having an average particle size from about 0.1 micron to about 25 microns.

10. The marking composition of claim 1 , wherein the colorant is derived from plants or vegetables.

11. The marking composition of claim 1 , further comprising one or more additives selected from the group consisting of rust preventives, anticorrosive agents, fillers, leveling agents, viscosity modifiers, drying agent, plasticizers, foam inhibitors, mold release agents, and polymer stabilizers.

12. A writing instrument comprising a marking composition,

wherein the writing instrument is selected from the group consisting of crayons, wax pastels, grease pencils, water-soluble crayons, colored ink markers, colored charcoals, and chalks; and

wherein the marking composition comprises

a condensation polymer which is a reaction product of a diol and a dicarboxylic acid, in an amount from about 10% to about 90% by weight of the composition;

one or more fatty acids containing from 10 to 24 carbon atoms, or an ester thereof, in an amount from about 20% to about 80% by weight of the composition; and

a colorant, in an amount from about 1% to about 15% by weight of the composition;

wherein the polymer has a Shore D hardness value from 35 to 65, and

wherein the polymer has a weight average molecular weight of from about 5000 to about 15,000 daltons and is selected from the group consisting of poly(butylene adipate), poly(hexylene succinate), and poly(propylene adipate).

13. The writing instrument of claim 12 , wherein the polymer comprises from about 20% to about 80% by eight of the composition.

14. The writing instrument of claim 12 , wherein the diol and the dicarboxylic acid each contain 2 to 14 carbon atoms.

15. The writing instrument of claim 12 , wherein the polymer has a melting point from about 40 C to about 75 C.

16. The writing instrument of claim 12 , wherein the marking composition comprises one or more fatty acids containing from 14 to 18 carbon atoms, or an ester thereof, in an amount from about 20% to about 80% by weight of the composition.

17. The writing instrument of claim 12 , wherein the one or more fatty acids comprise are fully saturated fatty acids.

18. The writing instrument of claim 12 , wherein the one or more fatty acids have a weight average molecular weight of from about 100 to about 400 daltons.

19. The writing instrument claim 12 , wherein the colorant is an inorganic pigment.

20. The writing instrument of claim 12 , wherein the colorant is a pigment having an average particle size from about 0.1 micron to about 25 microns.

21. The writing instrument of claim 12 , wherein the colorant is derived from plants or vegetables.

22. The writing instrument of claim 12 , wherein the marking composition further comprises one or more additives selected from the group consisting of rust preventives, anticorrosive agents, fillers, leveling agents, viscosity modifiers, drying agent, plasticizers, foam inhibitors, mold release agents, and polymer stabilizers.

23. The writing instrument of claim 12 , wherein the writing instrument is a crayon.

Assignments (15)
SECURITY INTEREST Recorded Dec 17, 2024
From: DANIMER SCIENTIFIC, INC.; MEREDIAN HOLDINGS GROUP, INC.; DANIMER SCIENTIFIC HOLDINGS, LLC; MEREDIAN, INC.; DANIMER SCIENTIFIC, L.L.C.; DANIMER BIOPLASTICS, INC.; DANIMER IPCO, LLC; DANIMER IPHOLDCO, LLC; NOVOMER, INC.
To: JEFFERIES CAPITAL SERVICES, LLC; RIVA RIDGE MASTER FUND, LTD.; BPI CREDIT 6, L.L.C.
Reel/Frame 069888/0715 →
SECURITY INTEREST Recorded Mar 22, 2023
From: DANIMER SCIENTIFIC, INC.; MEREDIAN HOLDINGS GROUP, INC.; DANIMER SCIENTIFIC HOLDINGS, LLC; DANIMER SCIENTIFIC MANUFACTURING, INC.; MEREDIAN, INC.; DANIMER SCIENTIFIC, L.L.C.; DANIMER SCIENTIFIC KENTUCKY, INC.; DANIMER BIOPLASTICS, INC.; DANIMER IPCO, LLC; NOVOMER, INC.; DANIMER IPHOLDCO, LLC
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 063146/0091 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 17, 2023
From: MEREDIAN, INC.
To: DANIMER IPCO, LLC
Reel/Frame 063113/0383 →
RELEASE OF SECURITY INTEREST Recorded Mar 16, 2023
From: SOUTHEAST COMMUNITY DEVELOPMENT FUND X, L.L.C.
To: DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.; DANIMER SCIENTIFIC, L.L.C.
Reel/Frame 063006/0860 →
RELEASE OF SECURITY INTEREST Recorded Jan 20, 2023
From: WHITE OAK GLOBAL ADVISORS, LLC
To: DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.,; DANIMER SCIENTIFIC, L.L.C.
Reel/Frame 062440/0763 →
NUNC PRO TUNC ASSIGNMENT Recorded Jan 12, 2023
From: TECNIQ HOLDINGS, LLC
To: DANIMER BIOPLASTICS, INC.
Reel/Frame 062353/0128 →
RELEASE OF SECURITY INTEREST Recorded Aug 5, 2022
From: TRUIST BANK
To: DANIMER SCIENTIFIC, L.L.C.; DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.
Reel/Frame 061088/0018 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 29, 2022
From: DANIMER BIOPLASTICS, INC.
To: MEREDIAN, INC.
Reel/Frame 060675/0123 →
SECURITY INTEREST Recorded May 3, 2021
From: DANIMER SCIENTIFIC, L.L.C.; DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.
To: TRUIST BANK
Reel/Frame 056122/0473 →
RELEASE OF SECURITY INTEREST Recorded Feb 5, 2021
From: WHITE OAK GLOBAL ADVISORS, LLC
To: DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.; DANIMER SCIENTIFIC, L.L.C.
Reel/Frame 055225/0196 →
SECURITY INTEREST Recorded Mar 19, 2019
From: DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.; DANIMER SCIENTIFIC, L.L.C.
To: SOUTHEAST COMMUNITY DEVELOPMENT FUND X, L.L.C.
Reel/Frame 048639/0606 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 19, 2019
From: EFFEKT LLC
To: TECNIQ HOLDINGS, LLC
Reel/Frame 048636/0753 →
SECURITY INTEREST Recorded Mar 15, 2019
From: DANIMER BIOPLASTICS, INC.; MEREDIAN, INC.; MEREDIAN BIOPLASTICS, INC.; DANIMER SCIENTIFIC, L.L.C.
To: WHITE OAK GLOBAL ADVISORS, LLC
Reel/Frame 048612/0195 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 9, 2019
From: ARNOLD, RACHELLE; JOHNSON, ADAM; VAN TRUMP, PHILLIP
To: DANIMER BIOPLASTICS, INC.
Reel/Frame 047937/0057 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 25, 2018
From: FALKEN, ROB
To: EFFEKT LLC
Reel/Frame 044730/0479 →
Continuity (2)
Provisional Application 62413150 · Oct 26, 2016
Related Publication 20180112095A1 · Apr 26, 2018