Novolac resins and use in rubber compositions

Patent metadata

Field	Value
Publication number	US-11236190-B2
Application number	US-201816489197-A
Country	US
Kind code	B2
Filing date	Feb 28, 2018
Priority date	Feb 28, 2017
Publication date	Feb 1, 2022
Grant date	Feb 1, 2022

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

What is claimed is:

1. A pastille or prill comprising a resorcinolic novolac resin composition including:
(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 1 mole % to 10 mole % of the total resorcinolic aromatic rings in formula (I) and formula (II) have been aralkylated, and wherein the composition has an aldehyde to resorcinol molar ratio of from about 0.50:1 to about 0.62:1, and
wherein the pastille or prill only exhibits up to 0.56 weight % fines when tested for brittleness as measured with a Tyler Ro-Tap Model B sieve shaker.

2. The pastille or prill of claim 1 , where the aralkyl groups are styryl groups.

3. The pastille or prill of claim 1 , where the alkylene bridge is a methylene bridge.

4. A method for forming a pastille or prill comprising an aralkyl-substituted resorcinolic novolac resin, the method comprising:
reacting (i) an aldehyde or ketone with (ii) an aralkyl-substituted resorcinol and resorcinol, in the presence of a catalyst of toluene sulfonic acid, 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, to provide a solid resorcinolic novolac resin; and
forming the solid resorcinolic novolac resin into the form of a pastille or prill, and wherein the pastille or prill only exhibits up to 0.56 weight % fines when tested for brittleness as measured with a Tyler Ro-Tap Model B sieve shaker.

5. The method of claim 4 , 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.

6. The method of claim 4 , 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.

7. The method of claim 4 , where the aldehyde or ketone is an aldehyde and the aldehyde is formaldehyde or methyl formcel.

8. The method of claim 4 , where the aralkyl-substituted resorcinol is styryl resorcinol or methyl styryl resorcinol.

9. The method of claim 4 , 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.

10. 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 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, wherein the resin is disposed in the natural rubber in the form of pastilles or prills, and wherein the pastilles or prills only exhibit up to 0.56 weight % fines when tested for brittleness as measured with a Tyler Ro-Tap Model B sieve shaker.

11. The rubber composition of claim 10 , wherein the resorcinol is aralkylated with styrene.

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

13. The composition of claim 10 , 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.

14. The composition of claim 10 , wherein the diene rubber is natural rubber.

15. The composition of claim 10 , 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
• Sumitomo Chemical Co

Inventors

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

Classifications

• C08L61/14

  Modified phenol-aldehyde condensates · CPC title

• C08K5/34922

  Melamine; Derivatives thereof · CPC title

• C09J161/14

  Modified phenol-aldehyde condensates · CPC title

• C08J7/12

  Chemical modification · CPC title

• C08L2205/04

  containing interpenetrating networks · CPC title