| US 7,550,599 B2 | ||
| Water compatible sterically hindered alkoxyamines and hydroxy substituted alkoxyamines | ||
| Mervin G. Wood, Mobile, Ala. (US); Robert Detlefsen, Putnam Valley, N.Y. (US); James Galbo, Wingdale, N.Y. (US); Wanda Martin, Fruitdale, Ala. (US); Paul Kondracki, Miramar (India); Michael P. DiFazio, Mobile, Ala. (US); and Joseph E. Babiarz, Amawalk, N.Y. (US) | ||
| Assigned to Ciba Specialty Chemicals Corporation, Tarrytown, N.Y. (US) | ||
| Filed on May 25, 2005, as Appl. No. 11/136,792. | ||
| Application 11/136792 is a continuation in part of application No. 10/782524, filed on Feb. 19, 2004, abandoned. | ||
| Claims priority of provisional application 60/450262, filed on Feb. 26, 2003. | ||
| Prior Publication US 2005/0261401 A1, Nov. 24, 2005 | ||
| Int. Cl. C07D 211/94 (2006.01); C08K 5/3435 (2006.01) | ||
| U.S. Cl. 546—244 [524/99; 546/242] | 24 Claims |
1. A water compatible or water soluble sterically hindered hydroxy substituted alkoxyamine compound selected from the group
consisting of compounds of formulae (1 )-(4)
 E is —O-T-(OH)b,
T is a straight or branched chain alkylene of 1 to 18 carbon atoms, cycloalkylene of 5 to 18 carbon atoms, cycloalkenylene
of 5 to 18 carbon atoms, a straight or branched chain alkylene of 1 to 4 carbon atoms substituted by phenyl or by phenyl substituted
by one or two alkyl groups of 1 to 4 carbon atoms;
b is 1, 2 or 3 with the proviso that b cannot exceed the number of carbon atoms in T, and when b is 2 or 3, each hydroxyl
group is attached to a different carbon atom of T;
R is hydrogen or methyl,
R1 is hydrogen, C1-C12alkyl, C5-C8cycloalkyl, C5-C8cycloalkyl substituted by one to three C1-C4alkyl, C2-C12alkenyl, phenyl, C7-C9phenylalkyl, glycidyl, C2-C12alkanoyl, C6-C9cycloalkylcarbonyl, C2-C12carbamoyl, C2-C12alkenoyl, benzoyl, benzoyl substituted by one to three C1-C4alkyl, C2-C12alkanoyl substituted by a di(C1-C6alkyl) phosphonate,
or R1 is C2-C12aIkyl, C2-C12alkanoyl or C7-C18phenylalkyl, each interrupted by one to six oxygen, sulfur or —N(R6)—groups; C1-C12alkyl, C2-C12alkanoyl, phenyl or C7-C18phenylalkyl, each substituted by one to six hydroxy groups or by one to six —NHR6 groups; C2-C12alkyl, C2-C12alkanoyl or C7-C18phenylalkyl, each interrupted by one to three —NR6C(O)— groups; or C1-C12alkyI, C2-C12alkanoyl, phenyl or C7-C18phenylalkyl, each substituted by one to three —SO3H groups or by one to three —COOR6 groups; or
R1 is said alkyl substituted by a piperazine or by a morpholine group; or
R1 is said interrupted group further substituted by one to six hydroxy groups or by one to six —NHR6 groups; or
R1 is said interrupted group further substituted by one to three —SO3H groups or by one to three —COOR6 groups;
or R1 is a mono-valent homo- or co-oligomer consisting of monomer units derived from monomers selected from the group consisting
of ethylene oxide, propylene oxide, ethylene glycol, propylene glycol, acrylic acid, methacrylic acid, ethylene imine, acrylamide,
vinyl formamide, vinyl alcohol and vinyl acetate; which homo- or co-oligomer consists of between 2 and about 24 monomer units;
R1′ is independently defined as for R1,
R6 is hydrogen or C1-C6alkyl,
R6′ and R6″ are independently defined as for R6,
X− is an inorganic or organic anion,
Y+ is a mono-, di- or tri-valent cation,
R2 is C1-C12alkyl, C2-C12alkanoyl, phenyl or C7-C18phenylalkyl, each substituted by one or two —COO−Y+, —N(R6)(R6′)(R6′)+X−or —SO3−Y+ groups; or
R2 is said C1-C12aIkyl, C2-C12alkanoyl, phenyl or C7-C18phenylalkyl, each of which is substituted by one or two —COO−Y+, —N(R6)(R6′)(R6″)+X− or —SO3−Y+ groups, each further substituted by one or two —OH, —COOR6 or —NHR6 groups; or
R2 is a mono-valent homo- or co-oligomer consisting of monomer units derived from monomers selected from the group consisting
of ethylene oxide, propylene oxide, ethylene glycol, propylene glycol, acrylic acid, methacrylic acid, ethylene imine, acrylamide,
vinyl formamide, vinyl alcohol and vinyl acetate; which homo- or co-oligomer consists of between 2 and about 24 monomer units,
R2′ is glycidyl, C2-C12alkanoyl substituted by a di(C1-C6alkyl) phosphonate, or
R2′ is C2-C12alkyl, C2-C12alkanoyl or C7-C18phenylalkyl, each interrupted by one to six oxygen, sulfur or —N(R6)— groups; C1-C12alkyl, C2-C12alkanoyl, phenyl or C7-C18phenylalkyl, each substituted by one to six hydroxy groups or by one to six —NHR6 groups; C2-C12alkyl, C2-C12alkanoyl or C7-C18phenylalkyl, each interrupted by one to three —NR6C(O)—groups; or R2′ is C1-C12alkyl, C2-C12alkanoyl, phenyl or C7-C18phenylalkyl, each substituted by one to three —SO3H groups or by one to three —COOR6 groups; or
R2′ is said alkyl substituted by a piperazine or by a morpholine group; or
R2′ is said interrupted group further substituted by one to six hydroxy groups or by one to six —NHR6 groups; or
R2′ is said interrupted group further substituted by one to three —SO3H groups or by one to three —COOR6 groups; or
R2′ is C1-C12alkyl, C2-C12alkanoyl, phenyl or C7-C18phenylalkyl, each substituted by one or two —COO−Y+, —N(R6)(R6′)(R6″)+X−or —SO3−Y+ groups; or
R2′ is said C1-C12alkyl, C2-C12alkanoyl, phenyl or C7-C18phenylalkyl, each of which is substituted by one or two —COO−Y+, —N(R6)(R6′)(R6″)+X− or —SO3−Y+ groups, each further substituted by one or two —OH, —COOR6 or —NHR6 groups; or
R2′ is a mono-valent homo- or co-oligomer consisting of monomer units derived from monomers selected from the group consisting
of ethylene oxide, propylene oxide, ethylene glycol, propylene glycol, acrylic acid, methacrylic acid, ethylene imine, acrylamide,
vinyl formamide, vinyl alcohol and vinyl acetate; which homo- or co-oligomer consists of between 2 and about 24 monomer units,
or
R2′ may also be hydrogen,
R3 is C1-C12alkyl, C2-C12alkanoyl, phenyl or C7-C18phenylalkyl, each substituted by one or two —COO−Y+, —N(R6)(R6′)(R6″)+X− or —SO3−Y+ groups; or
R3 is said C1-C12alkyl, C2-C12alkanoyl, phenyl or C7-C18phenylalkyl, each of which is substituted by one or two —COO−Y+, —N(R6)(R6′)(R6″)+X−or —SO3−Y+groups, each further substituted by one or two —OH, —COOR6 or —NHR6 groups; or
R3 is a mono-valent homo- or co-oligomer consisting of monomer units derived from monomers selected from the group consisting
of ethylene oxide, propylene oxide, ethylene glycol, propylene glycol, acrylic acid, methacrylic acid, ethylene imine, acrylamide,
vinyl formamide, vinyl alcohol and vinyl acetate; which homo- or co-oligomer consists of between 2 and about 24 monomer units,
or
R3 is —SO3H, —PO3H2, —SO3−Y+ or —PO3H−Y+, and R4 is defined as for R2′.
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