In-situ alkylphenol-aldehyde resins

Patent metadata

Field	Value
Publication number	US-10647806-B2
Application number	US-201815947503-A
Country	US
Kind code	B2
Filing date	Apr 6, 2018
Priority date	Oct 17, 2013
Publication date	May 12, 2020
Grant date	May 12, 2020

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.

First claim

We claim:

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.

Assignees

• Si Group Inc

Inventors

• Banach Timothy Edward
• Whitney John Morgan
• Hiscock Jeffrey M
• Makenzie Todd Scott
• Barbiero Gennaro

Classifications

• C08G8/32

  by organic acids or derivatives thereof, e.g. fatty oils · CPC title

• C08G8/28

  Chemically modified polycondensates · CPC title

• C08L7/00

  Compositions of natural rubber · CPC title

• C08L61/14

  Modified phenol-aldehyde condensates · CPC title

• C08G8/24

  with mixtures of two or more phenols which are not covered by only one of the groups C08G8/10 - C08G8/20 · CPC title