Novolac resins and use in rubber compositions

Patent metadata

Field	Value
Publication number	US-2020062884-A1
Application number	US-201816489197-A
Country	US
Kind code	A1
Filing date	Feb 28, 2018
Priority date	Feb 28, 2017
Publication date	Feb 27, 2020
Grant date	—

Abstract

A resorcinolic novolac resin composition comprising the reaction product of (i) an aldehyde or ketone, and (ii) aralkyl-substituted resorcinol and resorcinol, where the moles of the aralkyl-substituted resorcinol to the total moles of the resorcinol and aralkyl-substituted resorcinol is 0.01:1 to 0.4:1.

First claim

1 . A resorcinolic novolac resin composition comprising:
(i) a resin including units defined by the formula (I)

where R 1 is a hydrogen atom or an aralkyl group, at least one of R 2 and R 3 is an alkylene bridge, and the other of R 2 and R 3 is an alkylene bridge or a hydrogen atom; and

(ii) unreacted resorcinolic compounds defined by the formula (II)

where R 1 is a hydrogen atom or an aralkyl group, and where the composition includes greater than 1 mole and less than 40 moles of aralkyl groups per mole of units defined by the formula (I) plus moles of compounds defined by the formula (II).

2 . The composition of claim 1 , where the aralkyl groups are styryl groups.

3 . The composition of claim 1 , where the composition includes less than 14 moles of aralkyl groups per mole of units defined by the formula (I) plus moles of compounds defined by the formula (II).

4 . The composition of claim 1 , where the composition includes less than 10 moles of aralkyl groups per mole of units defined by the formula (I) plus moles of compounds defined by the formula (II).

5 . The composition of claim 1 , where the alkylene bridge is a methylene bridge.

6 . The composition of claim 1 , where the resin is in the form of pastilles or prills.

7 . (canceled)

8 . (canceled)

9 . (canceled)

10 . (canceled)

11 . (canceled)

12 . (canceled)

13 . (canceled)

14 . A method for forming an aralkyl-substituted resorcinolic novolac resin, the method comprising:
reacting (i) an aldehyde or ketone with (ii) an aralkyl-substituted resorcinol and resorcinol, where the moles of the aralkyl-substituted resorcinol to the total moles of the resorcinol and aralkyl-substituted resorcinol is 0.01:1 to 0.4:1.

15 . The method of claim 14 , where the moles of the aralkyl-substituted resorcinol to the total moles of the resorcinol and aralkyl-substituted resorcinol is 0.01:1 to 0.1:1.

16 . The method of claim 14 , where the moles of the aralkyl-substituted resorcinol to the total moles of the resorcinol and aralkyl-substituted resorcinol is 0.01:1 to 0.09:1.

17 . The method of claim 14 , where the aldehyde or ketone is selected from the group consisting of formaldehyde, methyl formcel, acetaldehyde, propionaldehyde, butyraldehyde, crotonaldehyde, cinnamaldehyde, benzaldehyde, furfural, acetone, and methyl ethyl ketone.

18 . The method of claim 14 , where the aldehyde or ketone is and aldehyde and the aldehyde is formaldehyde or methyl formcel.

19 . The method of claim 14 , where the aralkyl-substituted resorcinol is styryl resorcinol or methyl styryl resorcinol.

20 . The method of claim 14 , where the molar ratio of (i) the aldehyde or ketone to (ii) the aralkyl-substituted resorcinol and resorcinol is from about 0.5:1 to 1:1.

21 . An improved rubber composition comprising (1) per 100 parts diene rubber component selected from natural rubber, synthetic rubber or combinations thereof, and (2) 0.1 to 10 parts aralkyl-substituted resorcinolic novolac resin having from 1 mole % to about 40 mole % of the resorcinol aralkylated with one or more compounds selected from the group consisting of styrene, alpha-methyl styrene, beta-methyl styrene and p-methyl styrene.

22 . The rubber composition of claim 21 , wherein the aralkyl-substituted resorcinolic novolac resin has from 1 mole % to about 10 mole % of the resorcinol aralkylated with one or more compounds selected from the group consisting of styrene, alpha-methyl styrene, beta-methyl styrene and p-methyl styrene.

23 . The rubber composition of claim 21 , wherein the resorcinol is aralkylated with styrene.

24 . The rubber composition of claim 21 , wherein the rubber composition further comprises 0.1 to 10 parts methylene donor based on 100 parts diene rubber component.

25 . The composition of claim 21 , wherein the synthetic rubber is selected from the group consisting of styrene-butadiene rubber, butadiene rubber, isoprene rubber, acrylonitrile-butadiene rubber, chloroprene rubber, isobutylene-isoprene rubber, ethylene propylene copolymer and ethylene propylene diene rubber.

26 . The composition of claim 21 , wherein the diene rubber is natural rubber.

27 . The composition of claim 21 , further comprising a methylene donor selected from the group consisting of hexamethylenetetramine, methylol melamine, etherified methylol melamines and esterified methylol melamines.

Assignees

• Sumitomo Chemical Advanced Tech Llc D B A Sumika Electronic Materials
• Sumitomo Chemical Co

Inventors

• Itahashi Tamon
• Mcnaughton David P
• Tajima Koichiro
• Walkup Michael C

Classifications

• C08L2205/04

  containing interpenetrating networks · CPC title

• C08G8/22 Primary

  Resorcinol · CPC title

• C08L61/12 Primary

  with polyhydric phenols · CPC title

• C09J161/14

  Modified phenol-aldehyde condensates · CPC title

• C08J7/12

  Chemical modification · CPC title