IP Library Granted Patent US 9,944,744
Granted Patent B2
US 9,944,744 · App. 14/514,636 · Granted Apr 17, 2018

In-situ alkylphenol-aldehyde resins

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Quick Facts
Patent No.
US 9,944,744
App. No.
14/514,636
Granted
Apr 17, 2018
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 a raw alkylphenol composition comprising:

one or more alkylphenol compounds, each compound having one or more alkyl substituents, and

phenol;

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

wherein the alkylphenol composition comprises:

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

about 5 to about 10 wt % phenol,

about 7 to about 14 wt % di-tert-alkylphenol,

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

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

2. The process of claim 1 , wherein the alkylphenol composition includes para-tert-butylphenol.

3. The process of claim 1 , wherein the alkylphenol composition comprises para-tert-butylphenol, phenol, di-tert-butylphenol, and optionally tri-tert-butylphenol and ortho-tert-butylphenol.

4. The process of claim 1 , wherein the alkylphenol composition comprises:

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

about 5 to about 10 wt % phenol,

about 7 to about 14 wt % di-tert-butylphenol,

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

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

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

6. The process of claim 1 , wherein the alkylphenol composition includes para-tert-butyl phenol and para-tert-octylphenol.

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

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

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

10. The process of claim 9 , 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.

11. The process of claim 9 , further comprising the step of reacting the amine-modified alkylphenol-aldehyde resin with a salicylic acid.

12. The process of claim 11 , wherein the amine is morpholine.

Assignments (7)
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 →
RELEASE OF SECURITY INTEREST Recorded Nov 1, 2024
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: SI GROUP, INC.; ADDIVANT USA, LLC; SI GROUP USA (USAA), LLC (F/K/A ADDIVANT USA, LLC)
Reel/Frame 069290/0057 →
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 →
SECURITY INTEREST Recorded Nov 16, 2018
From: SI GROUP, INC.; ADDIVANT USA, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 048822/0965 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 16, 2015
From: BANACH, TIMOTHY E.; WHITNEY, JOHN M.; HISCOCK, JEFFREY M.; MAKENZIE, TODD S.; BARBIERO, GENNARO
To: SI GROUP, INC.
Reel/Frame 034740/0286 →