Bisphenol alternative derived from renewable substituted phenolics and their industrial application

Patent metadata

Field	Value
Publication number	US-2017210689-A1
Application number	US-201515313656-A
Country	US
Kind code	A1
Filing date	May 27, 2015
Priority date	May 27, 2014
Publication date	Jul 27, 2017
Grant date	—

Abstract

A compound is provided according to structure 4, (4) wherein n has a value from 0 to 48 and Z is hydroxyl or a benzene ring bearing substituents R 11 -R 15 , wherein R 1 -R 15 are each individually selected from the group consisting of H, allyl, alkyl, alkoxy, phenyl, phenoxy, halide, hydroxyl, glycidyl, (meth)acryloyl, 3-(meth)acryloyl-2-hydroxy-1-propoxy, 2,3-epoxypropyl, maleate, and structure (a) wherein at least one of R 1 -R 5 , at least one of R 6 -R 10 , and at least one of R 11 -R 15 is hydroxyl or an ether or ester derived from it.

First claim

1 . A compound according to structure 4,

wherein n has a value from 0 to 48 and Z is hydroxyl or a benzene ring bearing substituents R 11 -R 15 , wherein R 1 -R 15 are each individually selected from the group consisting of H, allyl, alkyl, alkoxy, phenyl, phenoxy, halide, hydroxyl, glycidyl, (meth)acryloyl, 3-(meth)acryloyl-2-hydroxy-1-propoxy, 2,3-epoxypropyl, maleate, and structure (a)

wherein at least one of R 1 -R 5 , at least one of R 6 -R 10 , and at least one of R 11 -R 15 is hydroxyl or an ether or ester derived from it;
wherein the repeat units comprising R 6 -R 10 , X′ and Y′ may be the same or different from each other when n>1;
wherein X, X′, X″, Y, Y′, and Y″ are each individually selected from the group consisting of H, alkyl, aryl, halo, hydroxyl phenyl, substituted phenyl, or wherein one or more of X and Y, X′ and Y′, and X″ and Y″ together constitute ═O;
excluding compounds according to structure 4 comprising two or fewer glycidyl, (meth)acryloyl and/or 3-(meth)acryloyl-2-hydroxy-1-propoxy substituents in total and in which the only phenolic moieties present are formed from one or more of vanillyl alcohol, hydroquinone, bisphenol A, bisphenol AP, bisphenol AF, bisphenol B, bisphenol BP, bisphenol C, bisphenol E, bisphenol F, bisphenol G, bisphenol M, bisphenol S, bisphenol P, bisphenol PH, bisphenol TMC, bisphenol Z, condensates consisting of only 1 vanillyl alcohol unit and only 1 cresol unit, and condensates consisting of only 1 vanillyl alcohol unit and only 1 phenol unit, except that the following are not excluded:
A) compounds bearing two or fewer meth(acryloyl) and/or 3-(meth)acryloyl-2-hydroxy-1-propoxy substituents, separately or in combination, in which the compounds comprise one or more moieties formed from vanillyl alcohol;
B) compounds bearing two or fewer glycidyl substituents and comprising three or more vanillyl alcohol, hydroquinone, or cresol moieties; and
C) compounds bearing two or fewer glycidyl, (meth)acryloyl and/or 3-(meth)acryloyl-2-hydroxy-1-propoxy substituents, separately or in combination, in which the only phenolic moieties present are formed from vanillyl alcohol and one or more of bisphenol A, bisphenol AP, bisphenol AF, bisphenol B, bisphenol BP, bisphenol C, bisphenol E, bisphenol F, bisphenol G, bisphenol M, bisphenol S, bisphenol P, bisphenol PH, bisphenol TMC, and bisphenol Z.

2 . The compound according to claim 1 , wherein at least one of R 11 -R 15 is structure (a).

3 . The compound according to claim 1 , wherein X, X′, X″, Y, Y′, and Y″ are all H.

4 . The compound according to claim 1 , wherein at least one of R 1 -R 15 is glycidyl.

5 . The compound according to claim 4 , wherein at least one of R 1 -R 15 is (meth)acryloyl or 3-(meth)acryloyl-2-hydroxy-1-propoxy.

6 . The compound according to claim 1 , wherein at least one of R 1 -R 5 , at least one of R 6 -R 10 , or at least one of R 11 -R 15 is neither H nor OH.

7 . A composition comprising the reaction product of the compound according to claim 4 with an epoxy curing agent.

8 . The compound according to claim 4 , wherein n=0 and Z is said benzene ring bearing substituents R 11 -R 15 .

9 . A composition comprising the reaction product of the compound according to claim 8 with an epoxy curing agent.

10 . A polymer or oligomer comprising two or more units of the compound according to claim 1 , wherein each unit is joined to one or more other units by a CH 2 CH(OH)CH 2 group attached to phenolic oxygen atoms on the units, and wherein at least one of R 1 -R 15 on at least one of the units is glycidyl.

11 . The polymer or oligomer according to claim 10 wherein at least one of R 1 -R 15 is (meth)acryloyl or 3-(meth)acryloyl-2-hydroxy-1-propoxy.

12 . A composition comprising the reaction product of the polymer or oligomer according to claim 10 with an epoxy curing agent.

13 . The composition according to claim 10 , wherein n=0 and Z is said benzene ring bearing substituents R 11 -R 15 .

14 . A composition comprising the reaction product of the polymer or oligomer according to claim 13 with an epoxy curing agent.

15 . The composition according to claim 7 , further comprising one or more materials selected from the group consisting of fibers, reinforcing materials, clays, silicates, fillers and whiskers.

16 . The composition according to claim 7 , further comprising one or more materials selected from the group consisting of nanofibers, nanoclays, nanofillers, and nanowhiskers.

17 . The composition according to claim 7 , further comprising one or more materials selected from the group consisting of solvents, flow additives, pigments, corrosion inhibitors, film formers, defoamers, coupling agents, antioxidants, stabilizers, flame retardants, reheating aids, plasticizers, flexibilizers, anti-fogging agents, and nucleating agents.

18 . A polymer or oligomer comprising two or more units of the compound according to claim 1 , wherein each unit is joined to one or more other units by a CH 2 CH(OH)CH 2 group attached to phenolic oxygen atoms on the units, and wherein at least one of R 1 -R 15 on at least one of the units is 3-(meth)acryloyl-2-hydroxy-1-propoxy.

19 . A composition comprising units of the polymer or oligomer of claim 18 joined by chain growth polymerization.

20 . The polymer or oligomer of claim 18 , wherein n=0 and Z is said benzene ring bearing substituents R 11 -R 15 .

21 . A composition comprising units of the polymer or oligomer of claim 20 joined by chain growth polymerization.

22 . A polymer or oligomer comprising two or more units of the compound according to claim 1 , wherein each unit is joined to one or more other units by a CH 2 CH(OH)CH 2 group attached to phenolic oxygen atoms on the units, and wherein at least one of R 1 -R 15 on at least one of the units is (meth)acryloyl.

23 . A composition comprising units of the polymer or oligomer of claim 22 joined by chain growth polymerization.

24 . The polymer or oligomer of claim 22 , wherein n=0 and Z is said benzene ring bearing substituents R 11 -R 15 .

25 . A composition comprising units of the polymer or oligomer of claim 24 joined by chain growth polymerization.

26 . The compound according to claim 1 , wherein at least one of R 1 -R 15 is 3-(meth)acryloyl-2-hydroxy-1-propoxy.

27 . A composition comprising the compound according to claim 26 , homopolymerized or copolymerized through chain growth polymerization.

28 . The compound according to claim 26 , wherein n=0 and Z is said benzene ring bearing substituents R 11 -R 15 .

29 . A composition comprising the compound according to claim 28 , homopolymerized or copolymerized through chain growth polymerization.

30 . The composition according to claim 19 , further comprising one or more materials selected from the group consisting of fibers, reinforcing materials, clays, silicates, fillers and whiskers.

31 . The composition according to claim 19 , further comprising one or more materials selected from the group consisting of nanofibers, nanoclays, nan

Assignees

• Wool Deborah
• Reno Kaleigh Havery
• STANZIONE Joseph Francis
• Sadler Joshua M
• Lascala John Joseph
• Hernandez Eric David
• Univ Delaware
• Dept Of The Army
• Univ Rowan

Inventors

• Reno Kaleigh Harvey
• Stanzione Iii Joseph Francis
• Wool Richard Patrick
• Sadler Joshua M
• Lascala John Joseph
• Hernandez Eric David

Classifications

• C08G63/547

  Hydroxy compounds containing aromatic rings · CPC title

• C08G18/3215

  containing aromatic groups or benzoquinone groups · CPC title

• C08G64/06

  not containing aliphatic unsaturation · CPC title

• C08G59/063 Primary

  with epihalohydrins · CPC title

• C08G64/28

  and phenols · CPC title