IP Library Granted Patent US 9,598,580
Granted Patent B2
US 9,598,580 · App. 14/642,285 · Granted Mar 21, 2017

Polymers, composites, and methods for making polymers and composites

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Quick Facts
Patent No.
US 9,598,580
App. No.
14/642,285
Granted
Mar 21, 2017
Kind
B2
Abstract

Polymeric materials and methods for making the polymeric materials utilizing bisphenolic stillbottoms, lignosulfonates, or both are disclosed. In one embodiment, a polymer is provided that includes a condensate of bisphenolic stillbottoms, an optional phenolic compound independent of bisphenolic stillbottoms, an aldehyde, and a lignosulfonate compound. The condensate may further include an amino compound, a catalyst, or combinations thereof. Alternatively, the polymer may be free of a phenolic compound independent of bisphenolic stillbottoms. The polymers may be used in the manufacture of articles including composites, laminates and paper products.

Claims (43)

1. A polymer comprising:

a condensate comprising:

from about 1 wt. % to about 20 wt. % of bisphenolic stillbottoms;

an optional phenolic compound independent of bisphenolic stillbottoms;

from about 10 wt. % to about 40 wt. % an aldehyde;

from about 5 wt. % to about 20 wt. % of a lignosulfonate compound;

from about 5 wt. % to about 12 wt % of catalyst;

from about 5 wt. % to about 20 wt. % of amino compound; and

from about 40 wt. % to about 60 wt. % of water, wherein the total weight percent (wt. %) is 100%.

2. The polymer of claim 1 , wherein the bisphenolic stillbottoms comprise a single-phase bisphenolic stillbottoms composition comprising:

bisphenolic stillbottoms in an amount from about 99% to about 85% based on the weight of the composition; and

a solvent in an amount from about 1% to about 15% based on the weight of the composition.

3. The polymer of claim 2 wherein the solvent is water or an organic solvent.

4. The polymer of claim 1 , wherein the bisphenolic stillbottoms comprise:

10 wt. % to 84 wt. % of p,p-Bisphenol A;

0 wt. % to 30 wt. % of o,p-Bisphenol A;

10 wt. % to 25 wt. % of trisphenol;

0 wt. % to 30 wt. % Chroman-I (p-(2,2,4-trimethyl-4-chromanyl)phenol);

0 wt % to 25 wt. % of phenol; and

45 wt. % to 75 wt. % of other phenol-acetone reaction products.

5. The polymer of claim 1 , wherein the phenolic compound independent of bisphenolic stillbottoms is selected from the group consisting of phenol, cresol, xylenol, alkyl substituted phenol, bisphenol A, bisphenol F, and combinations thereof.

6. The polymer of claim 5 , wherein the phenolic compound independent of bisphenolic stillbottoms composition comprises at least 90% phenol.

7. The polymer of claim 1 , wherein the aldehyde is selected from the group consisting of formaldehyde, acetaldehyde, propionaldehyde, n-butyraldehyde, isobutyraldehyde, benzaldehyde, glyoxal, furfural, glyoxal, glutaraldehyde, and combinations thereof.

8. The polymer of claim 1 , wherein the condensate further comprises an organic solvent.

9. The polymer of claim 1 , wherein the lignosulfonate compound comprises a compound selected from the group consisting of lignosulfonic acid sodium salt, lignosulfonic acid ammonium salt, lignosulfonic acid potassium salt, lignosulfonic acid calcium salt, and combinations thereof.

10. The polymer of claim 1 , wherein the condensate is free of the phenolic compound independent of bisphenolic stillbottoms.

11. The polymer of claim 1 , wherein the condensate comprises:

from about 0.5 wt. % to about 15 wt. % phenolic compound independent of bisphenolic stillbottoms, wherein the total weight percent (wt. %) is 100%.

12. The polymer of claim 1 , wherein the bisphenolic stillbottoms is derived from a bisphenol A process, the bisphenolic stillbottoms is derived from a bisphenol F process, and combinations thereof.

13. A method of making a polymer, the method comprising:

mixing and reacting:

from about 10 wt. % to about 40 wt. % of an aldehyde,

from about 5 wt. % to about 20 wt. % of a lignosulfonate compound, and

from about 1 wt. % to about 20 wt. % of bisphenolic stillbottoms;

from about 5 wt. % to about 12 wt. % of catalyst;

from about 5 wt. % to about 20 wt. % of amino compound; and

from about 40 wt. % to about 60 wt. % of water, wherein the total weight percent (wt. %) is 100%.

14. The method of claim 13 , further comprising adding a phenolic compound independent of bisphenolic stillbottoms.

15. The method of claim 13 , wherein the mixing and reacting comprises:

at least mixing bisphenolic stillbottoms and a lignosulfonate compound to produce a reaction product;

adding at least an aldehyde to the reaction product; and

mixing and reacting the reaction product and the at least an aldehyde.

16. The method of claim 13 , wherein the bisphenolic stillbottoms is derived from a bisphenol A process, the bisphenolic stillbottoms is derived from a bisphenol F process, and combinations thereof.

Assignments (11)
RELEASE OF SECURITY INTEREST IN PATENTS (TERM LOAN) RECORDED AT REEL/FRAME 049741/0425 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0473 →
RELEASE OF SECURITY INTEREST IN PATENTS (ABL) RECORDED AT REEL/FRAME 049740/0770 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0490 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0748 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0823 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: ROYAL BANK OF CANADA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0842 →
PATENT SECURITY INTEREST (ABL) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049740/0770 →
PATENT SECURITY INTEREST (TERM LOAN) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049741/0425 →
PATENT SECURITY INTEREST ASSIGNMENT AGREEMENT Recorded Apr 3, 2019
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS THE PRIOR COLLATERAL AGENT
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS THE CURRENT COLLATERAL AGENT
Reel/Frame 048788/0617 →
RELEASE OF SECURITY INTEREST Recorded Feb 23, 2017
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: HEXION INC.
Reel/Frame 041793/0920 →
SECURITY INTEREST Recorded Feb 13, 2017
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 041693/0888 →
SECURITY INTEREST Recorded Feb 2, 2016
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 037639/0795 →