Processes for producing molded articles stabilized against ultraviolet light and thermal degradation

Patent metadata

Field	Value
Publication number	US-2017349730-A1
Application number	US-201715624229-A
Country	US
Kind code	A1
Filing date	Jun 15, 2017
Priority date	May 1, 2014
Publication date	Dec 7, 2017
Grant date	—

Abstract

A process for producing a stabilized molded article including: combining a stabilizing amount of a thermal and ultraviolet (UV) light stabilizer composition with an organic material subject to degradation induced by light, heat or oxidation to form a stabilized organic material; and forming the stabilized organic material into a molded article, wherein the stabilizer composition comprises an ortho-hydroxyl tris-aryl-s-triazine compound; a hindered amine light stabilizer compound; a hindered hydroxybenzoate compound; an acid scavenger; a phosphite compound; a hindered phenol antioxidant compound; and a thioester compound

First claim

What is claimed is:

1 . A process for producing a stabilized molded article, said process comprising:
combining a stabilizing amount of a thermal and ultraviolet (UV) light stabilizer composition with an organic material subject to degradation induced by light, heat or oxidation to form a stabilized organic material; and forming the stabilized organic material into a molded article, wherein the stabilizer composition comprises an ortho-hydroxyl tris-aryl-s-triazine compound; a hindered amine light stabilizer compound; a hindered hydroxybenzoate compound; an acid scavenger; a phosphite compound; a hindered phenol antioxidant compound; and a thioester compound.

2 . The process according to claim 1 , wherein the organic material subject to degradation induced by light, heat or oxidation is selected from the group consisting of polyolefins, polyesters, potyethers, polyketones, polyamides, natural and synthetic rubbers, polyurethanes, polystyrenes, high-impact polystyrenes, polyacrylates, polymethacrylates, polyacetals, potyacrylonitriles, polybutadienes, polystyrenes, acrylonitrile-butadiene-styrene, styrene acrylonitrile, acrylate styrene acrylonitrile, cellulosic acetate butyrate, cellulosic polymers, polyimicles polyamideimides, polyetherimides, polyphenylsulfides, polyphenyloxidepolysulfones, polyethersulfones, polyvinylchlorides, polycarbonates, polyketones, aliphatic polyketones, thermoplastic olefins, aminoresin cross-linked polyacrylates and polyesters, polyisocyanate cross-linked polyesters and polyacrylates, phenol/formaldehyde, urea/formaldehyde and melamine/formaldehyde resins, drying and non-drying alkyd resins, alkyd resins, polyester resins, acrylate resins cross-linked with melamine resins, urea resins, isocyanates, isocyanurates, carbamates, and epoxy resins, cross-linked epoxy resins derived from aliphatic, cycloaliphatic, heterocyclic and aromatic glycidyl compounds, which are cross-linked with anhydrides or amines, polysiloxanes, Michael addition polymers, amines, blocked amines with activated unsaturated and methylene compounds, ketimines with activated unsaturated and methylene compounds, polyketimines in combination with unsaturated acrylic polyacetoacetate resins, polyketimines in combination with unsaturated acrylic resins, radiation curable compositions, epoxymelamine resins, organic dyes, cosmetic products, cellulose-based paper formulations, photographic film paper, fibers, waxes, inks, and blends thereof.

3 . The process according to claim 2 , wherein the organic material is selected from the group consisting of thermoplastic olefins, acrylonitrile-butadiene-styrene, polyesters, polyvinylchloride, polyamides, polyurethanes, or homo- and copolymers of propylene, isobutylene, butene, methylpentene, hexene, heptene, octene, isoprene, butadiene, hexadiene, dicyclopentadiene, ethylidene cyclopentene and norbornene.

4 . The process according to claim 3 , wherein the material to be stabilized is polyethylene or polypropylene.

5 . The process according to claim 1 or claim 3 , wherein:
(a) the ortho-hydroxyl tris-aryl-s-triazine compound is a 2-(2′-hydroxyphenyI)-1,3,5-triazine compound according to Formula (I):

wherein

each of R 34 and R 35 in Formula (I) is independently chosen from C 6 -C 10 aryl optionally substituted, C 1 -C 10 hydrocarbyl-substituted amino, C 1 -C 10 acyl or C 1 -C 10 alkoxyl; and R 36 in Formula (I) is present at from 0 to 4 positions of the phenoxy portion of Formula I and in each instance is independently chosen from hydroxyl, C 1 -C 12 hydrocarbyl, C 1 -C 12 alkoxyl, C 1 -C 12 alkoxyester, or C 1 -C 12 acyl,
(b) the hindered amine light stabilizer compound comprises a molecular fragment according to Formula (II):

wherein
R 31 in Formula I is chosen from: hydrogen; OH; C 1 -C 20 hydrocarbyl; —CH 2 CN; C 1 -C 2 acyl; or C 1 -C 18 al koxy;
R 38 in Formula (II) is chosen from: hydrogen; or C 1 -C 8 hydrocarbyl; and
each of R 29 , R 30 , R 32 , and R 33 in Formula (II) is independently chosen from C 1 -C 20 hydrocarbyl, or R 29 and R 30 and/or R 32 and R 33 in Formula (II) taken together with the carbon to which they are attached form a C 5 -C 10 cycloalkyl; or
according to Formula (IIa)

wherein
m in Formula is an integer from 1 to 2;
R 39 is chosen from: hydrogen; OH; C 1 -C 20 hydrocarbyl; —CH 2 CN; C 1 -C 12 acyl; or C 1 -C 18 alkoxy; and
each of G 1 -G 4 in Formula (IIa) is independently chosen from C 1 -C 20 hydrocarbyl,

(c) the hindered hydroxybenzoate compound is according to Formula (III):

wherein
R 17 in Formula (III) is a C 1 -C 8 alkyl and R 18 in Formula (III) is a C 1 -C 24 alkyl or substituted or unsubstituted C 6 -C 24 aryl,

(d) the acid scavenger is selected from the group consisting of zinc oxide, calcium lactate, natural and synthetic hydrotalcites, natural and synthetic hydrocalumites, alkali metal salts and alkaline earth metal salts of higher fatty acids, calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium stearate, sodium ricinoleate and potassium palmitate, antimony pyrocatecholate, zinc pyrocatecholate; and mixtures thereof,
(e) the hindered phenol antioxidant compound coinptises a molecular fragment according to one or more of Formula (IVa), (IVb), or (IVc):

wherein
R 18 in Formulae (IVa), (IVb) and (IVc) is chosen from hydrogen or a C 1-4 hydrocarbyl;
each of R 19 and R 20 in Formulae (IVa), (IVb) and (IVc) is individually chosen from hydrogen or a C 1 -C 20 hydrocarbyl; and
R 37 in Formulae (IVa), (IVb) and (IVc) is chosen from C 1 -C 12 hydrocarbyl, and
(f) the phosphite compound is chosen from a hindered arylalkyl phosphite compound according to Formula (V):

wherein
each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 in Formula (V) is individually chosen from hydrogen, C 1 -C 12 alkyl, C 3 -C 12 cycloalkyl, C 4 -C 12 alkyl cycloalkyl, C 6 -C 10 aryl, or C 7 -C 12 alkylaryl,

R 1 and R 5 together comprise at least 5 carbons and at least one of R 1 and R 5 comprises a tertiary carbon,
R 6 and R 10 together comprise at least 5 carbons and at least one of R 6 and R 10 comprises a tertiary carbon; or
a trisarylphosphite according to Formula (VI):

wherein
each of R 16 , R 17 , R 40 , R 41 , and R 42 in Formula (VI) is individually chosen from hydrogen, C 1 -C 20 alkyl, C 3 -C 20 cycloalkyl, C 4 -C 20 alkyl cycloalkyl, C 6 -C 10 aryl, or C 7 -C 20 alkylaryl; or
mixtures of Formula (V) and Formula (VI); and

(g) the thioester compound is selected from the group consisting of dilauryl thiodipropionate, distearyl thiodipropionate, pentaerythrithol tetrakis-(3-dodecylthipropionate), tetra-alkyl thioethyl thiodisuccinate, 2,12-dihydroxy-4,10-dithia-7-oxatridecamethylene bis[3-(dodecylthio)propionate], polyalkanoll esters of alkylthio-alkanoic acids, and dialkyl 3,3′-thiodipropionates; and mixtures thereof.

6 . The process ac

Assignees

• Cytec Ind Inc

Inventors

• Gupta Ram B
• Eng Jerry Mon Hei
• Khawam Fadi
• Kamat Ranjan Kumar

Classifications

• C08K5/105

  with phenols · CPC title

• C08K5/132

  Phenols containing keto groups {, e.g. benzophenones} · CPC title

• C08K5/524

  Esters of phosphorous acids, e.g. of H3PO3 · CPC title

• C08K5/3462

  Six-membered rings · CPC title

• C08K5/20

  Carboxylic acid amides · CPC title