IP Library Granted Patent US 10,793,757
Granted Patent B2
US 10,793,757 · App. 15/776,893 · Granted Oct 6, 2020

Polymer compositions and hot-melt adhesives formed therefrom

Inventors: Patrick Hayes (Ringoes, NJ); Daniel Carraway (Bainbridge, GA); Steven Wann (Bainbridge, GA); Rachelle Arnold (Bainbridge, GA); Joe B. Grubbs, III (Bainbridge, GA)
Assignees: Henkel IP & Holding GmbH; Danimer Bioplastics, Inc.
C09J167/04C08G63/60C08G81/00C09J5/06C08G2170/20C09J2453/00
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Quick Facts
Patent No.
US 10,793,757
App. No.
15/776,893
Granted
Oct 6, 2020
Kind
B2
Abstract

Predominately bio-sourced polymer compositions that may be used as hot-melt adhesives are disclosed herein. The polymer compositions may contain a polymer that has the following structure: G 1 and G 2 are independently (CH 2 ) x . Variable x is an integer ranging between 1 and 10. Variable y is an integer ranging between about 50 and about 500. Variable z is an integer ranging between about 100 and about 600. Variable n is an integer ranging between about 5 and about 10,000. X is H, a functionalized alkylene polymer block containing alcohol functional groups, or a mixture thereof. Y is H, an acyl group, a functionalized alkylene polymer containing carboxylic acid functional groups, or a mixture thereof.

Claims (39)

1. A polymer composition comprising:

a polymer comprising a lactic acid block and an aliphatic polyester block, the polymer having a structure of:

wherein G 1 and G 2 are independently (CH R ) x , R is an alkyl group or H, and x is an integer ranging between 1 and 10;

wherein y is an integer ranging between 50 and 500;

wherein z is an integer ranging between 100 and 600;

wherein n is an integer ranging between 5 and 10,000;

wherein X is H, a functionalized alkylene polymer block containing alcohol functional groups, or a mixture thereof; and

wherein Y is H, an acyl group, a functionalized alkylene polymer containing carboxylic acid functional groups, or a mixture thereof.

2. The polymer composition of claim 1 , wherein the lactic acid block contains L-lactic acid.

3. A method comprising:

combining a lactic acid block and an aliphatic polyester block, the lactic acid block having a structure of

and the aliphatic polyester block having a structure of

and

reacting the lactic acid block and the aliphatic polyester block to form the polymer of claim 1 ;

wherein G 1 and G 2 are independently (CH R ) x , R is an alkyl group or H, and x is an integer ranging between 1 and 10;

wherein y is an integer ranging between about 50 and 500;

wherein z is an integer ranging between about 100 and 600;

wherein X is H, a functionalized alkylene polymer block containing alcohol functional groups, or a mixture thereof; and

wherein Y is H, an acyl group, a functionalized alkylene polymer containing carboxylic acid functional groups, or a mixture thereof.

4. A hot melt adhesive including:

a polymer comprising a lactic acid block and an aliphatic polyester block, the polymer having a structure of:

wherein G 1 and G 2 are independently (CH R ) x , R is an alkyl group or H, and x is an integer ranging between 1 and 10;

wherein y is an integer ranging between 50 and 500;

wherein z is an integer ranging between 100 and 600;

wherein n is an integer ranging between 5 and 10,000;

wherein X is H, a functionalized alkylene polymer block containing alcohol functional groups, or a mixture thereof; and

wherein Y is H, an acyl group, a functionalized alkylene polymer containing carboxylic acid functional groups, or a mixture thereof.

5. The hot melt adhesive of claim 4 , wherein the lactic acid block contains L-lactic acid.

6. The hot-melt adhesive of claim 4 consisting of the polymer and optionally one or more additives.

7. The hot melt adhesive of claim 4 having a viscosity of 800 to 3000 cPs at 290° F.

8. The hot melt adhesive of claim 4 having less than 10% drop in viscosity after storage for 24 hours at 290° F.

9. The hot melt adhesive of claim 4 having an open time of 5 seconds or more.

10. A package comprising two substrates bonded together by the hot melt adhesive of claim 4 .

11. The hot melt adhesive of claim 4 having a viscosity of 4000 to 5000 cPs at 290° F.

12. The hot melt adhesive of claim 4 having a drop in viscosity after storage for 24 hours at 290° F. from about 10% to about 30%.

13. The polymer composition of claim 1 , wherein Y is an acyl group having from 2 to 20 carbon atoms.

14. The polymer composition of claim 1 , wherein Y is a propionyl group.

15. The hot melt adhesive of claim 4 , wherein Y is an acyl group having from 2 to 20 carbon atoms.

16. The hot melt adhesive of claim 4 , wherein Y is a propionyl group.

Assignments (16)
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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 9, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059357/0267 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 19, 2019
From: WANN, STEVEN
To: DANIMER BIOPLASTICS, INC.
Reel/Frame 048631/0068 →
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 →
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 Feb 28, 2019
From: CARRAWAY, DANIEL
To: DANIMER BIOPLASTICS, INC.
Reel/Frame 048466/0880 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 17, 2018
From: HAYES, PATRICK
To: HENKEL IP & HOLDING GMBH
Reel/Frame 047794/0344 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 17, 2018
From: GRUBBS, JOE B., III; ARNOLD, RACHELLE
To: DANIMER BIOPLASTICS, INC.
Reel/Frame 047794/0277 →
Continuity (2)
Provisional Application 62257318 · Nov 19, 2015
Related Publication 20180334599A1 · Nov 22, 2018