Water compatible sterically hindered alkoxyamines and...

C - Chemistry – Metallurgy – 07 – D

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C07D 211/94 (2006.01) C07D 401/14 (2006.01) C08K 5/3435 (2006.01) C08K 5/3492 (2006.01)

Patent

CA 2517334

Sterically hindered alkoxyamine and hydroxy substituted alkoxyamine stabilizer compounds are made water compatible via certain backbones with affinity towards water. The sterically hindered amines are for example of the formula where for example E and E~ are 2-hydroxycydohexyloxy, 2-hydroxy-2- methylpropoxy, benzyloxy, methoxy, propoxy, hexyloxy, heptyloxy, oclyloxy or cyclohexyloxy, Rx is for example -NH2+CH2CH20H Cl-, -NH3+ -OAc, =NOH, - NHCH(CH3)COO-K+,- NHCH2CH2NH(CH3)2+ -OAC, -NHCH2CH2SO3-K+, -NHCH(COO- K+)CH2CH2SCH3, -NHCH2COO- K+, -OCH(CH3)COO-K+, -OCH2CH2NH(CH3)2+ -OAC, - OCH2CH2SO3-K+, -OCH(COO- K+)CH2CH2SCH3 or -OCH2COO-K+, and where R5 comprises repeating units of -(OCH2CH2)-, -(OCH2CH2(CH3))-,-(CH2CHCOOH)-, - (CH2C(CH3)COOH)-, -(CH2CHCOOCH3)-, -(NHCH2CH2)-, -(CH2CHOH)-, -(CH2CHCONH2)-or -(CH2CH(NHCOH))-. These compounds are particularly effective in stabilizing aqueous polymer systems against the deleterious effects of oxidative, thermal and actinic radiation. The compounds are effective for example in stabilizing water borne coatings, aqueous inks, aqueous inkjet media and photocured aqueous systems.

L'invention concerne des composés d'alcoxyamine stériquement encombrée et des composés stabilisateurs d'alcoxyamine hydroxy substituée, qui sont rendus hydrocompatibles grâce à certains squelettes présentant une affinité pour l'eau. Les amines stériquement encombrée sont par exemple représentées par la formule (1), dans laquelle E et E' représentent par exemple 2-hydroxycyclohexyloxy, 2-hydroxy-2-méthylpropoxy, benzyloxy, méthoxy, propoxy, hexyloxy, heptyloxy, octyloxy ou cyclohexyloxy, R¿x? représente par exemple -NH¿2??+¿CH¿2?CH¿2?OH Cl?-¿, -NH¿3??+ -¿OAc, =NOH, -NHCH(CH¿3?)COO?-¿K?+¿,- NHCH¿2?CH¿2?NH(CH¿3?)¿2??+¿ ?-¿OAC, -NHCH¿2?CH¿2?SO¿3??-¿K?+¿, -NHCH(COO?-¿ K?+¿)CH¿2?CH¿2?SCH¿3?, -NHCH¿2?COO?-¿ K?+¿, -OCH(CH¿3?)COO?-¿K?+¿, -OCH¿2?CH¿2?NH(CH¿3?)¿2??+ -¿OAC, -OCH¿2?CH¿2?SO¿3??-¿K?+¿, -OCH(COO?-¿ K?+¿)CH¿2?CH¿2?SCH¿3? ou -OCH¿2?COO?-¿K?+¿, et R¿5? comporte des motifs répétés de -(OCH¿2?CH¿2?)-, -(OCH¿2?CH¿2?(CH¿3?))-,-(CH¿2?CHCOOH)-, -(CH¿2?C(CH¿3?)COOH)-, -(CH¿2?CHCOOCH¿3?)-, -(NHCH¿2?CH¿2?)-, -(CH¿2?CHOH)-, -(CH¿2?CHCONH¿2?)- ou -(CH¿2?CH(NHCOH))-. Ces composés sont particulièrement efficaces pour stabiliser des systèmes polymères aqueux contre les effets nuisibles d'un rayonnement oxydatif, thermique et actinique. Ces composés servent par exemple à stabiliser des revêtements aqueux, des encres aqueuses, des milieux aqueux pour impression à jet d'encre et des systèmes aqueux durcis par effet photochimique.

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