Nova Patents
EP0246483B1

Urethane-functional s-triazine crosslinking agents and curable compositions containing the same

Abstract

This record has no abstract on file.

EP0246483B1, drawing sheet 1
Sheet 1 of 199

Term

Term ended

Expired 4 May 2007, 19.4 years ago.

  1. Priority
  2. Filed
  3. Granted
  4. Expired
  5. Today

10 claims: 4 independent, 6 dependent

  1. 1
    A urethane-functional s-triazine crosslinking agent selected from (i) a compound of the formula wherein R¹ is wherein A¹ and A² are, independently, straight or branched chain divalent alkylene of from 2 to 10 carbon atoms and Q¹ and Q² are, independently, straight or branched chain alkyl or alkoxyalkyl of from 1 to 20 carbon atoms or straight or branched chain beta-hydroxyalkyl of from 2 to 10 carbon atoms;R² and R³ are, independently, the same as R¹ and, in addition, Cl, Br, I, OR⁴, -NHR⁵, -NR⁵R⁶, and R⁴, R⁵ and R⁶ are, independently, a monovalent C₁-C₃₀ radical selected from R being hydrogen or alkyl;and R⁷ is a divalent radical which forms divalent radicals selected from and R⁸ and R⁹ are the same as R⁴, R⁵ and R⁶ and in addition hydrogen;(ii) a self-condensed oligomer of (i);(iii) a urethane or urea compound comprising the reaction product of (i) or (ii) with a mono- or polyol or a mono- or polyamine;or (iv) a mixture of any of the foregoing.
  2. 2
    A triazine compound (i) as defined in Claim 1 wherein A¹ and A² are C₂-C₆ alkylene, and Q¹ and Q² are, independently, beta-hydroxyethyl, beta-hydroxypropyl, C₁-C₁₈ alkyl, or a mixture of two or more thereof.
  3. 3
    A triazine (i) as defined in Claim 1 wherein R¹ and R² are the same in which A¹ and A² are -CH₂CH₂- and Q¹ and Q² are beta-hydroxyethyl or beta-hydroxypropyl and R³ is NR⁵R⁶ wherein R⁵ and R⁶ are alkyl.
  4. 4
    An oligomer (ii) of a triazine compound (i) as defined in Claim 1 wherein A¹ and A² are -CH₂CH₂- and at least one of Q¹ and Q² are beta-hydroxyethyl or beta-hydroxypropyl.
  5. 5
    A thermosettable composition comprising:(a) a urethane-functional s-triazine cross-linking agent as defined in Claim 1;(b) a polymer containing two or more active hydrogen functional groups;and (c) optionally, a cross-linking catalyst;the cross-linking agent (a) and the polymer (b) being stable relative to each other in the composition at ambient temperature and reactive with each other at elevated temperature.
  6. 6
    A thermosettable composition comprising:(a) a self-condensable s-triazine compound selected from (i) a compound of the formula: wherein R¹ is wherein A¹, A², R¹, R², R³, Q¹ and Q² are as defined in Claim 1;(ii) a self-condensed oligomer of (i);(iii) a urethane or urea compound comprising the reaction product of (i) or (ii) with a mono- or polyol or a mono- or polyamine;or (iv) a mixture of any of the foregoing;and (b) optionally, a cross-linking catalyst.
  7. 7
    A composition as defined in Claim 5 wherein the components (a) - (c) thereof are present in weight proportions, based on the weight of resin solids for the resinous components, of from 15 to 50 parts of the cross-linking agent (a);from 50 to 85 parts of the polymer (b);and, when present, from 0.1 to 5 parts of the catalyst (c);A¹ and A² are C₂-C₆ alkylene and Q¹ and Q² are beta-hydroxyethyl, beta-hydroxypropyl or a C₁-C₁₈ alkyl radical.
  8. 8
    A composition as defined in Claim 5 wherein said polymer (b) containing active functional groups is selected from the class consisting of one or more of acrylic, polyester, vinyl, epoxy, polyurethane, polyamide, cellulosic, alkyd and silicone resins, and said active functional groups are selected from one or more of hydroxyl groups, amino groups, amide groups, carboxyl groups and mercapto groups.
  9. 9
    A substrate protectively coated with a cured composition as defined in Claim 5.
  10. 10
    A process for the preparation of a triazine compound of the formula wherein R 1 a is wherein A¹ and A² are, independently, straight or branched chain divalent alkylene of from 2 to 10 carbon atoms and Q 1 a and Q 2 b are, independently, straight or branched chain beta-hydroxyalkyl of from 2 to 10 carbon atoms;R 2 b and R 3 c are, independently, the same as R 1 a and, in addition, Cl, Br, I, or OR 4 a , wherein R 4 a is monovalent aliphatic of from 1 to 6 carbon atoms, said process comprising reacting a compound of the formula with a compound of the formula wherein at least one of X, Y and Z are displaceable groups selected from Cl, Br, I or -OR 4 a and any remaining groups are non-displaceable groups of the formula wherein A¹, A², Q 1 a , Q 1 b , and R 4 a are as defined above, optionally in the presence of a condensation catalyst, until formation of the desired compound is substantially complete and, if desired, reacting a product having no more than one of said displaceable groups X, Y and Z with a dialkyl amine to form a dimer, self-condensing the product to an oligomer, or forming a urethane or urea compound comprising a product from any such compound having at least one of said displaceable groups by reaction with a mono- or polyol or a mono- or polyamine, and recovering said products.
Independent claims10