IP Library › Granted Patent US 9,834,522
Granted Patent B2
US 9,834,522 · App. 14/768,217 · Granted Dec 5, 2017

Multi-functional acrylates

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Quick Facts
Patent No.
US 9,834,522
App. No.
14/768,217
Granted
Dec 5, 2017
Kind
B2
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.

Claims (18)

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.

Assignments (2)
SECURITY INTEREST Recorded Jan 29, 2019
From: EMPIRE TECHNOLOGY DEVELOPMENT LLC
To: CRESTLINE DIRECT FINANCE, L.P.
Reel/Frame 048373/0217 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 15, 2015
From: ADAM, GEORGIUS ABIDAL
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 036334/0123 →