# US 5,710,281 A · Organic compounds suitable as reactive diluents and binder precursor compositions including same

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- Number: US 5,710,281 A
- Document ID: US5710281A
- Status: Granted
- Kind: A
- Application number: 08/606,325
- Filed: 1996-02-23
- Granted: 1998-01-20
- Earliest claimed: 1993-10-27
- Assignees: Minnesota Mining and Manufacturing Company
- Inventors: Ernest L. Thurber; Eric G. Larson; Alan R. Kirk; Gregg D. Dahlke
- Web page: https://patentgrep.com/patent/US5710281A

## CPC

- C07D 209/48: with oxygen atoms in positions 1 and 3, e.g. phthalimide
- B24D 3/28: Resins {or natural or synthetic macromolecular compounds (B24D3/22 takes precedence)}
- B24D 3/344: {the bonding agent being organic}
- B24D 11/00: Constructional features of flexible abrasive materials; Special features in the manufacture of such materials
- C07C 69/017: Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
- C07C 69/54: Acrylic acid esters; Methacrylic acid esters
- C07D 261/14: Nitrogen atoms
- C07D 263/14: with radicals substituted by oxygen atoms
- C07D 277/24: Radicals substituted by oxygen atoms
- C07D 307/68: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D 333/38: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- Y10T 428/25: Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
- Y10T 428/252: Glass or ceramic [i.e., fired or glazed clay, cement, etc.] [porcelain, quartz, etc.]
- Y10T 428/257: Iron oxide or aluminum oxide
- Y10T 428/259: Silicic material
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- B24D: TOOLS FOR GRINDING, BUFFING OR SHARPENING (abrading-bodies specially designed for tumbling apparatus, e.g. abrading-balls B24B31/14; honing tools B24B33/08; lapping tools B24B37/11)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Organic compounds having at least one ethylenically-unsaturated group are described, the organic compounds being suitable for use in coatable compositions as reactive diluents; compounds of the invention preferably have a divalent organic linking moiety devoid of reactive groups other than optional ethylenically-unsaturated groups, and a polar organic moiety and are particularly adept in solubilizing aminoplast resins having radiation-curable pendant groups.

## Claims

### Claim 1

Organic compounds having at least one ethylenically-unsaturated group and being suitable for use as reactive diluents, said compounds being N-substituted succinimide derivatives of formula (III): ##STR18## wherein: R.sup.12 is selected from the group consisting of --C.sub.x H.sub.2x -- and --(C.sub.y H.sub.2y)--O--(C.sub.y' H.sub.2y'), wherein x is an integer ranging from 1 to 12 inclusive and y and y' are independently an integer ranging from 1 to 6 inclusive;
R.sup.13 is H;
W is selected from the group consisting of O, S, NR.sup.13 ; Y is selected from the group consisting of O, S, NR.sup.14 ;
R.sup.14 is selected from the group consisting of H, --C.sub.x H.sub.2x+1 -- wherein x is an integer ranging from 1 to 12 inclusive, --C(.dbd.O)--C(R.sup.13).dbd.CH.sub.2, and --R.sup.12 --O--C(.dbd.O)--C(R.sup.13).dbd.CH.sub.2 ;
Q is an organic radical which forms phthalimide, hexahydrophthalimide, tetrahydrophthalimide, or derivatives thereof with an N-substituted succinimide ring; and
t is 0 or 1.

### Claim 2 (depends on 1)

Compounds in accordance with claim 1 wherein a plurality of ethylenically unsaturated groups are present in the compound.

### Claim 3 (depends on 1)

Compounds in accordance with claim 1 wherein the number of ethylenically unsaturated groups in the compound ranges from 1 to 10.

### Claim 4

Compounds selected from the group consisting of cyclic imides within general formula (VI): ##STR19## wherein: Q is an organic radical which forms phthalimide, hexahydrophthalimide, tetrahydropthalimide, or derivatives thereof with an N-substituted succinimide ring;
W is selected from the group consisting of NR.sup.27, O, and S;
Y is selected from the group consisting of O, S, and NR.sup.28 ;
R.sup.25 is selected from the group consisting of --C.sub.x H.sub.2x -- and --(C.sub.y H.sub.2y)--)--(C.sub.y' H.sub.2y'), wherein x is an integer ranging from 1 to 12 inclusive and y and y' are independently an integer ranging from 1 to 6 inclusive;
R.sup.26 is --H;
R.sup.27 is selected from the group consisting of H and --C.sub.x H.sub.2x+1 ;
R.sup.28 is selected from the group consisting of H, --C.sub.x H.sub.2x+l, --C(.dbd.W)--C.dbd.CH.sub.2, and C.sub.x H.sub.2x --O--C(.dbd.W)--C.dbd.CH.sub.2 ; and wherein for R.sup.27 and R.sup.28, x ranges from 1 to 10 inclusive;
R.sup.27 and R.sup.28 may be the same or different.

### Claim 5

Carbocyclic imides selected from the group consisting of compounds within general formula (XII): ##STR20## wherein: Z.sup.1 is selected from the group consisting of H, and --C.sub.x H.sub.2x+1 wherein x ranges from 1 to 10 inclusive;
Y.sup.1 is selected from the group consisting of NR.sup.43 and O;
W is selected from the group consisting of O, S, NR.sup.42 ;
R.sup.41 is selected from the group consisting of --C.sub.x H.sub.2x -- and --(C.sub.y H.sub.2y)--O--(C.sub.y' H.sub.2y'), wherein x is an integer ranging from 1 to 12 inclusive and y and y' are independently an integer ranging from 1 to 6 inclusive;
R.sup.42 is --H;
R.sup.43 is selected from the group consisting of --H, --C.sub.x H.sub.2x+1, --C(.dbd.W)--CH.dbd.CH.sub.2, and --C.sub.x H.sub.2x --O--C(.dbd.W)--CH.dbd.CH.sub.2 wherein x ranges from 1 to 10 inclusive.

### Claim 6

Compounds selected from the group consisting of:
N-›2,3-Di(acryloyloxy)propyl!tetrahydrophthalimide;
N-›2,3-Di(acryloyloxy)propyl!hexahydrophthalimide; and
N-›2,3-Di(acryloyloxy)propyl!methyl nadimide.

### Claim 7 (depends on 1)

A coatable, addition polymerizable binder precursor composition comprising:
(a) an addition polymerizable resin; and
(b) an organic compound in accordance with claim 1.

### Claim 8 (depends on 7)

A coatable, addition polymerizable binder precursor composition in accordance with claim 7 comprising a plurality of abrasive particles.

### Claim 9 (depends on 1)

A coatable, addition polymerizable binder precursor composition comprising:
(a) an organic compound in accordance with claim 1; and
(b) a plurality of abrasive particles.