IP Library Granted Patent US 12,012,487
Granted Patent B2
US 12,012,487 · App. 17/407,947 · Granted Jun 18, 2024

In-situ alkylphenol-aldehyde resins

Inventors: Timothy Edward Banach (Schenectady, NY); John Morgan Whitney (Schenectady, NY); Jeffrey M. Hiscock (Schenectady, NY); Todd Scott Makenzie (Schenectady, NY); Gennaro Barbiero (Schenectady, NY)
Assignee: SI GROUP, INC.
C08G8/12C08G8/24C08G8/28C08G8/32C08L7/00C08L21/00C08L61/06C08L61/14
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Quick Facts
Patent No.
US 12,012,487
App. No.
17/407,947
Granted
Jun 18, 2024
Kind
B2
Abstract

The invention relates to an in-situ process for preparing an alkylphenol-aldehyde resin. The process comprises the step of providing a raw alkylphenol composition. The raw alkylphenol composition comprises one or more alkylphenol compounds and at least about 1 wt % phenol. Each alkylphenol compound has one or more alkyl substituents. The raw alkylphenol composition is reacted directly, without pre-purification, with one or more aldehydes to form an in-situ alkylphenol-aldehyde resin. The invention also relates to an in-situ alkylphenol-aldehyde resin formed from the in-situ process, and its use in a tackifier composition and rubber composition. The tackifier composition and rubber composition containing the in-situ alkylphenol-aldehyde resin show, inter alia, improved tack performance.

Claims (27)

1. An in-situ process for preparing an alkylphenol-aldehyde resin, comprising:

providing an alkylphenol composition comprising:

a butylphenol composition comprising one or more butylphenol compounds, each compound having one or more butyl substituents; and an octylphenol composition comprising one or more octylphenol compounds, each compound having one or more octyl substituents, wherein at least one of the butylphenol composition and the octylphenol composition is a raw alkylphenol composition;

about 7 to about 14 wt % di-tert-alkylphenol; and

at least about 1 wt % phenol; and

reacting, without pre-purifying the raw alkylphenol composition, the alkylphenol composition directly with one or more aldehydes to form an in-situ alkylphenol-aldehyde resin.

2. The in-situ process of claim 1 , wherein the alkylphenol-aldehyde resin is a novolak type resin.

3. The in-situ process of claim 1 , wherein the alkylphenol-aldehyde resin is a resole type resin.

4. The in-situ process of claim 1 , wherein the alkylphenol-aldehyde resin further comprises alkylphenol-aldehyde resins prepared from pure alkylphenol.

5. The in-situ process of claim 1 , wherein the aldehyde is formaldehyde.

6. The in-situ process of claim 1 , wherein the alkylphenol composition comprises about 1 wt % to about 10 wt % phenol.

7. The in-situ process of claim 1 , wherein the alkylphenol composition comprises one main alkylphenol component in an amount ranging from about 50 to about 85 wt %.

8. The in-situ process of claim 1 , wherein the alkylphenol composition comprises:

about 50 to about 85 wt % para-tert-alkylphenol,

0 to about 3 wt % ortho-tert-alkylphenol, and

0 to about 1 wt % tri-tert-alkylphenol.

9. The in-situ process of claim 1 , wherein the butylphenol composition comprises para-tert-butylphenol, di-tert-butylphenol, and optionally tri-tert-butylphenol and ortho-tert-butylphenol.

10. The in-situ process of claim 1 , wherein the octylphenol composition comprises para-tert-octylphenol, di-tert-octylphenol, and optionally ortho-tert-octylphenol and tri-tert-octylphenol.

11. The in-situ process of claim 1 , wherein the alkylphenol composition comprises para-tert-butylphenol, para-tert-octylphenol, di-tert-butylphenol, di-tert-octylphenol, and optionally ortho-tert-butylphenol, tri-tert-butylphenol, ortho-tert-octylphenol and tri-tert-octylphenol.

12. The in-situ process of claim 1 , further comprising the step of reacting the alkylphenol-aldehyde resin with an amine, forming an amine-modified alkylphenol-aldehyde resin.

13. The in-situ process of claim 12 , further comprising the step of reacting the amine-modified alkylphenol-aldehyde resin with an epoxide or a chemical reagent for stabilizing the amine moiety in the alkylphenol-aldehyde resin.

14. The in-situ process of claim 12 , further comprising the step of reacting the amine-modified alkylphenol-aldehyde resin with a salicylic acid.

15. The in-situ process of claim 12 , wherein the amine is morpholine.

16. The in-situ process of claim 1 , wherein the butylphenol composition is a raw alkylphenol composition, and the octylphenol composition is a raw alkylphenol composition.

17. The in-situ process of claim 16 , wherein the ratio of the raw butylphenol composition to the raw octylphenol composition ranges from about 90:10 to about 10:90.

18. The in-situ process of claim 16 , wherein the ratio of the raw butylphenol composition to the raw octylphenol composition ranges from about 75:25 to about 25:75.

19. The in-situ process of claim 18 , wherein the ratio of the raw butylphenol composition to the raw octylphenol composition ranges from about 60:40 to about 40:60.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Dec 30, 2025
From: ALTER DOMUS (US) LLC, AS COLLATERAL AGENT
To: SI GROUP, INC.
Reel/Frame 074136/0039 →
ASSIGNMENT OF SECURITY INTEREST IN PATENTS [REEL 068968/FRAME 0001] Recorded Dec 24, 2024
From: JPMORGAN CHASE BANK, N.A.
To: ALTER DOMUS (US) LLC
Reel/Frame 069770/0736 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 068968/0001 →
SECURITY INTEREST Recorded Sep 19, 2024
From: SI GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 068968/0024 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 10, 2022
From: BANACH, TIMOTHY EDWARD; WHITNEY, JOHN MORGAN; HISCOCK, JEFFREY M.; MAKENZIE, TODD SCOTT; BARBIERO, GENNARO
To: SI GROUP, INC.
Reel/Frame 059228/0554 →