IP Library Granted Patent US 9,765,174
Granted Patent B2
US 9,765,174 · App. 14/710,273 · Granted Sep 19, 2017

Modified phenolic resins and methods of making and using the same as reinforcing resins

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Quick Facts
Patent No.
US 9,765,174
App. No.
14/710,273
Granted
Sep 19, 2017
Kind
B2
Abstract

This invention relates to processes for preparing novolak resins and using the same as reinforcing resins. One process comprises reacting one or more alkylphenols with an aldehyde in the presence of a base to form a resole resin, wherein for each mole of alkylphenol at least 1.5 moles of aldehyde are reacted; and reacting the resole resin with one or more phenolic compounds in the presence of an acidic catalyst to form a novolac resin, wherein for each mole of alkylphenol at least 1.5 moles of the phenolic compounds are reacted. Another process comprises reacting one or more alkylphenols with an aldehyde in the presence of a base to form a resole resin, and reacting the resole resin with one or more phenolic compounds under an elevated temperature to form a novolac resin.

Claims (27)

1. A process for preparing a novolac resin, comprising:

(a) reacting one or more alkylphenols having an alkyl group of 8-12 carbons with an aldehyde in the presence of a base to form a resole resin, wherein for each mole of alkylphenol at least 1.5 moles of aldehyde are reacted, and

(b) reacting the resole resin with one or more phenolic compounds in the presence of an acidic catalyst to form a novolac resin, wherein for each mole of alkylphenol at least 1.5 moles of the phenolic compounds are reacted,

wherein step (b) further comprises, after the step of reacting the resole resin with one or more phenolic compounds, adding additional aldehyde,

wherein the novolac resin has a residual alkylphenol of less than 1% without being subjected to a distillation process.

2. The process of claim 1 , wherein at least one alkyl group in the alkylphenols is not C 8 .

3. The process of claim 1 , wherein one or more alkyl groups in the alkylphenols is C 8 or C 12 alkyl.

4. The process of claim 1 , wherein the phenolic compound is phenol.

5. The process of claim 4 , wherein the phenolic compound further comprises resorcinol.

6. The process of claim 5 , wherein the phenolic compound contains about 50-80 wt % phenol and about 20-50 wt % resorcinol.

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

8. The process of claim 1 , wherein the step of reacting one or more alkylphenols with an aldehyde is conducted at a temperature ranging from 50 to 90° C.

9. The process of claim 1 , wherein the step of reacting the resole resin with one or more phenolic compounds is conducted at a temperature ranging from room temperature to 130° C.

10. A process for preparing a novolac resin, comprising:

(a) reacting one or more alkylphenols having an alkyl group of 8-12 carbons with an aldehyde in the presence of a base to form a resole resin, wherein for each mole of alkylphenol at least 1.5 moles of aldehyde are reacted,

(b) reacting the resole resin with one or more phenolic compounds at an elevated temperature to form a novolac resin, wherein for each mole of alkylphenol at least 1.5 moles of the phenolic compounds are reacted,

wherein step (b) further comprises, after the step of reacting the resole resin with one or more phenolic compounds, neutralizing the resole resin with an acid and adding additional aldehyde,

wherein the novolac resin has a residual alkylphenol of less than 1% without being subjected to a distillation process.

11. The process of claim 10 , wherein one or more alkyl groups in the alkylphenols is C 8 or C 12 alkyl.

12. The process of claim 10 , wherein the phenolic compound is phenol.

13. The process of claim 12 , wherein the phenolic compound further comprises resorcinol.

14. The process of claim 13 , wherein the phenolic compound contains about 50-80 wt % phenol and about 20-50 wt % resorcinol.

15. The process of claim 10 , wherein the aldehyde is formaldehyde.

16. The process of claim 10 , wherein the step of reacting one or more alkylphenols with an aldehyde is conducted at a temperature ranging from 50 to 90° C.

17. The process of claim 10 , wherein the step of reacting the resole resin with one or more phenolic compounds is conducted at a temperature ranging from 100° C. to 200° C.

18. The process of claim 1 , further comprising the step of subjecting the novolac resin to a distillation process.

19. The process of claim 10 , further comprising the step of subjecting the novolac resin to a distillation process.

Assignments (3)
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 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 Jun 25, 2015
From: BANACH, TIMOTHY E.; WHITNEY, JOHN M.; LAMB, JAMES J.
To: SI GROUP, INC.
Reel/Frame 035908/0419 →