Multi-functional acrylates

Patent metadata

Field	Value
Publication number	US-9834522-B2
Application number	US-201314768217-A
Country	US
Kind code	B2
Filing date	Nov 21, 2013
Priority date	Feb 15, 2013
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

Disclosed herein are derivatives of phenolic and melamine compounds, methods of making these derivatives, and methods of using them. The compounds include phenolic and melamine compounds with multi-functional acrylate groups, polyethylene glycol and amino groups. The compounds may be cured to form resins that may be used in a variety of applications, such as paints, hydrogels, polyacrylate super absorbent polymers (SAPs), adhesives, composites, sealants, fillers, fire retardants, crosslinking agents, and the like.

First claim

What is claimed is:

1. A compound of formula II:

wherein:
R 1 is H, —(CH 2 —CH 2 —O) n H, —(CH 2 —CH 2 —CH 2 —O) n H, or —(CH 2 —CH 2 —O) n —(CH 2 —CH 2 —CH 2 —O) n H, wherein each n is, independently, an integer from 1 to 18;
R 2 is H, —C(═O)—CH═CH 2 , —(CH 2 —CH 2 —O) p H, —(CH 2 —CH 2 —CH 2 —O) p H, or —(CH 2 —CH 2 —O) p —(CH 2 —CH 2 —CH 2 —O) p H, wherein each p is, independently, an integer from 1 to 18;
R 3 is —N(CH 2 —CH 2 —NH 2 ) 2 , —O—(═O)—CH═CH 2 , N[CH 2 O—C(═O)—CH═CH 2 ] 2 , —NHC(═O)CH═CH 2 , —(CH 2 —CH 2 —O) q H, —(CH 2 —CH 2 —CH 2 —O) q H, —N[CH 2 —CH 2 —O—C(═O)—CH═CH 2 ] 2 , or —N[CH 2 —CH 2 —NH—C(═O)—CH═CH 2 ] 2 , wherein each q is, independently, an integer from 1 to 18;
R 4 is —N(CH 2 —CH 2 —NH 2 ) 2 , —O—C(═O)—CH═CH 2 , —NH—C(═O)CH═CH 2 , —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , —(CH 2 —CH 2 —O) r H, —(CH 2 —CH 2 —CH 2 —O) r H, —N[CH 2 —CH 2 —O—C(═O)—CH═CH 2 ] 2 , or —N[CH 2 —CH 2 —NH—C(═O)—CH═CH 2 ] 2 , wherein each r is, independently, an integer from 1 to 18;
R 5 is —N(CH 2 —CH 2 —NH 2 ) 2 , —O—C(═O)—CH═CH 2 , —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , —NH—C(═O)CH═CH 2 , —(CH 2 —CH 1 —O) s H, —(CH 2 —CH 2 —CH 2 —O) s H, —N[CH 2 —CH 2 —O—C(═O)—CH═CH 2 ] 2 , or —N[CH 2 —CH 2 —NH—C(═O)—CH═CH 2 ] 2 , wherein each s is, independently, an integer from 1 to 18;
R 6 is —N(CH 2 —CH 2 —NH 2 ) 2 , —O—C(═O)—CH═CH 2 , —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , —NH—C(═O)CH═CH 2 , —(CH 2 —CH 2 —O) t H, —(CH 2 —CH 2 —CH 2 —O) t H, —N[CH 2 —CH 2 —O—C(═O)—CH═CH 2 ] 2 , or —N[CH 2 —CH 2 —NH—C(═O)—CH═CH 2 ] 2 , wherein each t is, independently, an integer from 1 to 18; and
X is —CH 2 —, —C(CH 3 ) 2 —, —S—, —S(═O) 2 —, —S(═O)—, —CH(CCl 3 )—, —C(Cl) 2 —, —O—, or —C(F) 2 —.

2. The compound of claim 1 , wherein X is —C(CH 3 ) 2 —, R 1 is —(CH 2 —CH 2 —O) n H, R 2 is —(CH 2 —CH 2 —O) p H, R 3 is —O—C(═O)—CH═CH 2 , R 4 is —O—C(═O)—CH═CH 2 , R 5 is —O—C(═O)—CH═CH 2 , and R 6 is —O—C(═O)—CH═CH 2 .

3. The compound of claim 1 , wherein X is —C(CH 3 ) 2 —, R 1 is —(CH 2 —CH 2 —O) n H, R 2 is —(CH 2 —CH 2 —O) p H, R 3 is —N(CH 2 —CH 2 —NH 2 ) 2 , R 4 is —N(CH 2 —CH 2 —NH 2 ) 2 , R 5 is —N(CH 2 —CH 2 —NH 2 ) 2 , and R 6 is —N(CH 2 —CH 2 —NH 2 ) 2 .

4. The compound of claim 1 , wherein X is —C(CH 3 ) 2 —, R 1 is —(CH 2 —CH 2 —O) n H, R 2 is —(CH 2 —CH 2 —O) p H, R 3 is —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , R 4 is —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , R 5 is —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , and R 6 is —N[CH 2 O—C(═O)—CH═CH 2 ] 2 .

5. The compound of claim 1 , wherein X is —C(CH 3 ) 2 —, R 1 is H, R 2 is H, R 3 is —O—C(═O)—CH═CH 2 , R 4 is —O—C(═O)—CH═CH 2 , R 5 is —O—C(═O)—CH═CH 2 , and R 6 is —O—C(═O)—CH═CH 2 .

6. The compound of claim 1 , wherein X is —CH 2 —, R 1 is —(CH 2 —CH 2 —O) n H, R 2 is —(CH 2 —CH 2 —O) p H, R 3 is —O—C(═O)—CH═CH 2 , R 4 is —O—C(═O)—CH═CH 2 , R 5 is —O—C(═O)—CH═CH 2 , and R 6 is —O—C(═O)—CH═CH 2 .

7. The compound of claim 1 , wherein X is —CH 2 —, R 1 is —(CH 2 —CH 2 —O) n H, R 2 is —(CH 2 —CH 2 —O) p H, R 3 is —N(CH 2 —CH 2 —NH 2 ) 2 , R 4 is —N(CH 2 —CH 2 —NH 2 ) 2 , R 5 is —N(CH 2 —CH 2 —NH 2 ) 2 , and R 6 is —N(CH 2 —CH 2 —NH 2 ) 2 .

8. The compound of claim 1 , wherein X is —CH 2 —, R 1 is —(CH 2 —CH 2 —O) n H, R 2 is —(CH 2 —CH 2 —O) p H, R 3 is —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , R 4 is —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , R 5 is —N[CH 2 O—C(═O)—CH═CH 2 ] 2 , and R 6 is —N[CH 2 O—C(═O)—CH═CH 2 ] 2 .

9. The compound of claim 1 , wherein X is —CH 2 —, R 1 is H, R 2 is H, R 3 is —O—C(═O)—CH═CH 2 , R 4 is —O—C(═O)—CH═CH 2 , R 5 is —O—C(═O)—CH═CH 2 , and R 6 is —O—C(═O)—CH═CH 2 .

10. The compound of claim 1 , wherein the compound is incorporated into a polymer, a coating composition, or a hydrogel.

Assignees

• Empire Technology Dev Llc

Inventors

• Adam Georgius Abidal

Classifications

• C08F222/1006

  of polyhydric alcohols or polyhydric phenols · CPC title

• C09D167/02

  Polyesters derived from dicarboxylic acids and dihydroxy compounds (C09D167/06 takes precedence) · CPC title

• C08F220/30

  containing aromatic rings in the alcohol moiety · CPC title

• C07C215/50

  with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain · CPC title

• C07D251/70 Primary

  Other substituted melamines · CPC title