Non-yellowing part-tertiary-alkyl phenyl substituted...

Details Non-yellowing part-tertiary-alkyl phenyl substituted... Non-yellowing part-tertiary-alkyl phenyl substituted...

2001-05-18

2003-01-21

Sanders, Kriellion (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

C524S091000, C524S096000, C524S099000, C524S100000, C524S102000, C252S400230, C252S400240, C252S401000, C252S403000, C428S704000, C528S423000

Reexamination Certificate

active

06509399

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates generally to novel para-tertiary alkyl phenyl substituted triazines and pyrimidines and their use as protectants against degradation by environmental forces, including ultraviolet light, actinic radiation, oxygen, moisture, atmospheric pollutants and combinations thereof.
Exposure to sunlight and other sources of ultraviolet radiation is known to cause degradation of a variety of materials, especially polymeric materials. For example, polymeric materials such as plastics often discolor and may become brittle as a result of exposure to ultraviolet light. Accordingly, a large body of art has been developed directed towards materials such as ultraviolet light absorbers and stabilizers which are capable of inhibiting such degradation.
A class of materials known to be ultraviolet light absorbers are o-hydroxyphenyltriazines, in which at least one substituent on the 1, 3 or 5 carbon on the triazine ring is a phenyl group with a hydroxyl group ortho to the point of attachment to the triazine ring. In general this class of materials is well known in the art. Disclosures of such compounds can be found in U.S. Pat. Nos. 3,242,175 and 3,244,708.
A further example is found in U.S. Pat. Nos. 3,843,371 and 3,896,125, which disclose various hydroxyphenyltriazines. These triazines show poor solubilities and poor stabilities, and can discolor with time.
Hydroxyphenyltriazines in combination with other UV absorbers such as hydroxyphenylbenzotriazoles, benzophenones, oxanilides, cyanoacrylates, salicylates, acrylonitriles and thiozlines, are also well known. For example, U.S. Pat. Nos. 4,853,471, 4,973,702, 4,921,966 and 4,973,701 disclose such combinations.
Typically, the aforementioned aryl ring with the hydroxyl group ortho to the point of attachment to the triazine ring is based on resorcinol and, consequently, this aryl ring also contains a second substituent (either a hydroxyl group or a derivative thereof) para- to the point of attachment to the triazine ring. For example, U.S. Pat. Nos. 3,118,837 and 3,244,708 disclose p-alkoxy-o-hydroxyphenyl triazines with improved UV protection, but such triazines also exhibit poor solubility and poor long-term stabilities.
This para-substituent can be “non-reactive,” as in the case of an alkyloxy group, or “reactive” as in the case of a hydroxyalkyloxy (active hydrogen reactive site) or (meth)acryloyl (ethylenic unsaturation reactive site) group. For the purposes of the present invention, the former are referred to as “non-bondable” benzocycle-substituted pyrimidines and triazines and the latter are referred to as “bondable” para-tertiary alkyl phenyl substituted pyrimidines and triazines.
Many polymer additives (such as ultraviolet light stabilizers) volatilize or migrate out of the polymer substrate to be protected, or are adsorbed (chemically or physically) by one or more systems components (such as pigments), thereby diminishing their effectiveness. Such volatilization, migration and adsorption problems are examples of the general problems of lack of solubility and compatibility found for many commercial polymer additives.
Bondable triazines are well known in the art. For example, U.S. Pat. Nos. 3,423,360, 4,962,142 and 5,189,084 disclose various bondable and the incorporation of these compounds into polymers by chemical bonding. Bondable stabilizers have a potential advantage in this respect in that, depending on the bondable functionality and the particular polymer system to be stabilized, they can be chemically incorporated into a polymer structure via reaction of the bondable functionality either during polymer formation (such as in the case of polymerizing monomers or a crosslinking polymer system) or subsequently with a preformed polymer having appropriate reactive functionality. Due to such bonding, migration of these UV absorbers between layers of multi-layer coatings and into polymer substrates is greatly reduced.
Several of the previously incorporated references disclose tertiary alkylated substituted triazines. For example U.S. Pat. Nos. 3,242,175 and 3,244,708 disclose mono-tertiary butylated benzene triazines. There remains a need for new UV-stabilizers which possess improved compatibility with the polymer systems to which they are added, as well as impart improved environmental stability to such systems. The present invention provides novel para-tertiary alkyl phenyl substituted triazine and pyrimidine stabilizers which satisfy this need.
SUMMARY OF THE INVENTION
The present invention provides a new class of para-tertiary alkyl phenyl-substituted pyrimidines and triazines depicted below, in which a substituent attached to the triazine or pyrimidine ring is a bondable or non-bondable para-tertiary alkyl phenyl group:
wherein Z signifies a resorcinol radical which is bound through a cyclic carbon atom directly to the triazine ring or a substituted resorcinol radical, A can be a nitrogen or optionally substituted methine, and each R signifies a hydrocarbyl group to form a tertiary carbon attached to the ring. These para-tertiary alkyl phenyl substituted triazines and pyrimidines have the advantage of being highly soluble in and compatible with many polymers and coatings while being stable to environmental degradation that has lead previous UV stabilizers to turn yellow and to degrade with respect to performance as UV absorbers.
More specifically, the new para-tertiary alkyl phenyl substituted pyrimidines and triazines of the present invention have general formula (II):
wherein
each A is independently nitrogen or methine optionally substituted with R
2
, and at least two A are nitrogen;
X is independently selected from hydrogen and a blocking group
each of L, R
3
and R
4
are independently a hydrogen, hydrocarbyl, halogen, hydroxyl, cyano, —O(hydrocarbyl), —O(functional hydrocarbyl), —N(hydrocarbyl)(hydrocarbyl), —N(functional hydrocarbyl)(functional hydrocarbyl), —S(hydrocarbyl), —S(functional hydrocarbyl), —SO
2
(hydrocarbyl), —SO
3
(hydrocarbyl), —SO
2
(functional hydrocarbyl), —SO
3
(functional hydrocarbyl), —COO(hydrocarbyl), —COO(functional hydrocarbyl), —CO(hydrocarbyl), —CO(functional hydrocarbyl), —OCO(hydrocarbyl), —OCO(functional hydrocarbyl), —CONH
2
, —CONH(hydrocarbyl), —CONH(functional hydrocarbyl), —CON (hydrocarbyl)(hydrocarbyl), —CON(functional hydrocarbyl)(hydrocarbyl), —CON(functional hydrocarbyl)(functional hydrocarbyl), or a hydrocarbyl group substituted by any of the above groups; and
each R is identical or different, and is independently a hydrocarbyl group of between 1 and 21 carbon atoms, an alkenyl group of between 2 and 21 atoms, a cycloalkyl of between 5 and 21 carbon atoms, an aralkyl of between 7 and 21 carbon atoms, and of the above hydrocarbyl groups substituted with one or more groups selected from the following: halogen, hydroxyl, cyano, —O(hydrocarbyl), —O(functional hydrocarbyl), —N(hydrocarbyl)(hydrocarbyl), —N(functional hydrocarbyl)(functional hydrocarbyl), —S(hydrocarbyl), —S(functional hydrocarbyl), —SO
2
(hydrocarbyl), —SO
3
(hydrocarbyl), —SO
2
(functional hydrocarbyl), —SO
3
(functional hydrocarbyl), —COO(hydrocarbyl), —COO(functional hydrocarbyl), —CO(hydrocarbyl), —CO(functional hydrocarbyl), —OCO(hydrocarbyl), —OCO(functional hydrocarbyl), —CONH
2
, —CONH(hydrocarbyl), —CONH(functional hydrocarbyl), —CON(hydrocarbyl)(hydrocarbyl), —CON(functional hydrocarbyl)(hydrocarbyl), —CON(functional hydrocarbyl)(functional hydrocarbyl); provided that the R groups are connected to a quaternary carbon that is attached to the ring.
Preferably L is hydrogen, a hydrocarbyl group of 1 to 24 carbon atoms, or a functional hydrocarbyl group of 1 to 24 carbon atoms; and R is methyl, ethyl, propyl or phenyl. It is more preferred that each tertiary carbon attached to the ring have two R groups of methyl, ethyl or propyl and one of phenyl, or all three R groups being methyl, ethyl or propyl. It is most preferred for each tertiary carbon to have two R groups being methyl with the third R group being alkyl or phenyl. More preferably, each L in formula (II) is i

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