IP Library Granted Patent US 10,647,806
Granted Patent B2
US 10,647,806 · App. 15/947,503 · Granted May 12, 2020

In-situ alkylphenol-aldehyde resins

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Quick Facts
Patent No.
US 10,647,806
App. No.
15/947,503
Granted
May 12, 2020
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 (45)

1. An alkylphenol-aldehyde resin prepared by reacting, in an in-situ process, without pre-purification, a raw alkylphenol composition directly with one or more aldehydes, wherein the raw alkylphenol composition comprises

alkylphenol compounds, each compound having one or more alkyl substituents, wherein a main alkylphenol compound is present in an amount ranging from about 50 to about 85 wt %, and

about 5 to about 10 wt % phenol.

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

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

4. The alkylphenol-aldehyde resin of claim 1 , further comprising alkylphenol-aldehyde resins prepared from pure alkylphenol.

5. The alkylphenol-aldehyde resin of claim 1 , wherein the aldehyde is formaldehyde.

6. The alkylphenol-aldehyde resin of claim 1 , wherein the raw alkylphenol composition comprises about 6% to about 8 wt % phenol.

7. The alkylphenol-aldehyde resin of claim 1 , wherein the raw 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.

8. The alkylphenol-aldehyde resin of claim 1 , wherein the raw alkylphenol composition comprises a butylphenol composition comprising one or more butylphenol compounds, each compound having one or more butyl substituents.

9. The alkylphenol-aldehyde resin of claim 8 , wherein the butylphenol composition comprises para-tert-butylphenol, di-tert-butylphenol, and optionally tri-tert-butylphenol and ortho-tert-butylphenol.

10. The alkylphenol-aldehyde resin of claim 1 , wherein the raw 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.

11. The alkylphenol-aldehyde resin of claim 1 , wherein the raw alkylphenol composition comprises an octylphenol composition comprising one or more octylphenol compounds, each compound having one or more octyl substituents.

12. The alkylphenol-aldehyde resin of claim 11 , wherein the octylphenol composition comprises para-tert-octylphenol, di-tert-octylphenol, and optionally ortho-tert-octylphenol and tri-tert-octylphenol.

13. The alkylphenol-aldehyde resin of claim 1 , wherein the raw alkylphenol composition comprises:

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

about 5 to about 10 wt % phenol,

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

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

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

14. The alkylphenol-aldehyde resin of claim 1 , wherein the raw alkylphenol composition comprises 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.

15. The alkylphenol-aldehyde resin of claim 14 , wherein the ratio of the butylphenol composition to the octylphenol composition ranges from 90:10 to 10:90.

16. The alkylphenol-aldehyde resin of claim 14 , wherein the raw 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.

17. A tackifier composition having improved tack or tack retention, when used in a rubber composition, comprising the alkylphenol-aldehyde resin of claim 1 .

18. The tackifier composition of claim 17 , wherein the tack or tack retention of the formed alkylphenol-aldehyde resin increases about 10% or more compared to a tackifier composition comprising an alkylphenol-aldehyde resin prepared from a purified alkylphenol.

19. The tackifier composition of claim 18 , wherein the tack retention of the formed alkylphenol-aldehyde resin increases about 40% or more.

20. A rubber composition comprising:

the alkylphenol-aldehyde resin of claim 1 , and

a natural rubber, a synthetic rubber, or a mixture thereof.

21. The rubber composition of claim 20 , wherein the alkylphenol-aldehyde resin is used in an amount ranging from about 1 phr to about 7 phr.

22. The rubber composition of claim 20 , further comprising alkylphenol-aldehyde resins prepared from pure alkylphenol.

23. A tire comprising the rubber composition of claim 20 .

24. An alkylphenol-aldehyde resin prepared by reacting, in an in-situ process, without pre-purification, a raw alkylphenol composition directly with one or more aldehydes, wherein the raw alkylphenol composition comprises

alkylphenol compounds, each compound having one or more alkyl substituents, wherein a di-tert-alkylphenol compound is present in an amount ranging from about 7 to about 14 wt %, and

about 5 to about 10 wt % phenol.

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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2019
From: BANACH, TIMOTHY E.; WHITNEY, JOHN M.; HISCOCK, JEFFREY M.; MAKENZIE, TODD S.; BARBIERO, GENNARO
To: SI GROUP, INC.
Reel/Frame 049010/0900 →
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 →