EP0041555A4 - Nouvelles amines secondaires et tertiaires et leur utilisation dans des compositions et dans la stabilisation de polymeres contre la degradation par la lumiere ultraviolette. - Google Patents

Nouvelles amines secondaires et tertiaires et leur utilisation dans des compositions et dans la stabilisation de polymeres contre la degradation par la lumiere ultraviolette.

Info

Publication number
EP0041555A4
EP0041555A4 EP19810900159 EP81900159A EP0041555A4 EP 0041555 A4 EP0041555 A4 EP 0041555A4 EP 19810900159 EP19810900159 EP 19810900159 EP 81900159 A EP81900159 A EP 81900159A EP 0041555 A4 EP0041555 A4 EP 0041555A4
Authority
EP
European Patent Office
Prior art keywords
independently selected
alkyl
aralkyl
hydroxy substituted
amino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19810900159
Other languages
German (de)
English (en)
Other versions
EP0041555A1 (fr
Inventor
Pyong-Nae Son
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Goodrich Corp
Original Assignee
BF Goodrich Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BF Goodrich Corp filed Critical BF Goodrich Corp
Publication of EP0041555A1 publication Critical patent/EP0041555A1/fr
Publication of EP0041555A4 publication Critical patent/EP0041555A4/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3435—Piperidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4

Definitions

  • the Field of the Invention - This invention relates to novel compounds, compositions containing such compounds and methods for the stabilization of UV sensitive polymers. More specifically, this invention is directed to novel secondary and tertiary amines, stabilized polymer compositions containing such novel compounds and methods for the UV stabilization of photodegradable polymers.
  • Description of the Prior Art - Polymers have in the past and continue to provide an attractive -substitute for the more traditional types of structural materials (e.g. wood or metals) because of relatively inexpensive materials and fabrication cost. As polymers continue to find new applications in, for example, the fabrication of automotive parts and building materials, they must also become more durable and capable of withstanding prolonged exposure to a variety of degradative forces.
  • Degradation of polymers can be caused by exposure to light, heat, moisture and/or air. Such degradation is usually manifest by either a partial or total loss of structural integrity, changes in light transmission properties, changes in color, loss or reduction of flexibility and/or resiliency, or any combination of the above phenomena.
  • Those attempting to avoid polymer degradation have generally selected from among three possible approaches: (a) elimination or reduction of the degradative forces; (b) isolation of the sensitive material from the degradative forces; or (c) modification of the polymer composition to enhance its resistance to the degradative forces. The latter approach is generally preferable since it does not require elaborate engineering nor structural changes in the polymer product environment.
  • the problems associated with the stabilization of different polymeric materials are affected to a greater extent by the functionality of the polymer and any unsaturation that may be present along the backbone or the side chains of such materials.
  • the polymer contains unsaturation along its backbone and/or side chains, it is highly sensitive to oxidative degradation.
  • Materials that are suitable to prevent oxidative degradation of dienic or unsaturated polymers do not necessarily have similar beneficial effects when incorporated within a polymeric materials lacking such unsaturation.
  • stabilizers which are effective for polyolefins, such as polyethylene may have little, if any, stabilizing effect upon dienic polymers or polymers having unsaturation along their backbone or side chain.
  • additives which have been disclosed in the past as suitable for enhancing polymer resistance to one or more degradative forces described hereinabove.
  • These additives (hereinafter collectively referred to as "stabilizers") can usually be physically combined with or engrafted upon the environmentally sensitive polymer thereby prolonging its useful life in its hostile degradative environment.
  • stabilizers can usually be physically combined with or engrafted upon the environmentally sensitive polymer thereby prolonging its useful life in its hostile degradative environment.
  • polymers i.e. a stabilizer package
  • One of the more difficult to control of the degradative forces is the irradiation of polymers by ultraviolet light.
  • the impact of such irradiation will, of course, vary depending upon the intensity and duration of exposure and thus, may manifiest itself only after a prolonged interval.
  • the irradiation of polymers with ultraviolet light can oftentimes cause crosslinking of these materials, thereby reducing its resiliency and/or impact resistance. Changes in color and opacity are often effected by prolonged exposure of polymers to UV irradiation. While many materials are known and commercially available as stabilizers against ultraviolet light degradation, the degree of protection afforded by such agents is generally concentration dependent and may be geared to a particular limited class of material.
  • the stabilizer is a polyurea having piperdinyl functional moieties appended from its backbone.
  • the '248 patent is similar in its disclosure in that the piperidinyl functional moieties are appended from a polymer backbone composed of alkalene groups. While each of the foregoing stabilizer materials would appear to be attractive from the standpoint of low mobility, (due to its size) the presence of other components of the polymer backbone tends to increase the amount by weight, in relation to polymer, of such stabilizer that must be present in order to insure a sufficient number of stabilizer functional groups to adequately protect the ultraviolet light sensitive polymer against degradation.
  • the stabilization of polymers against changes in their physical, chemical and/or electrical properties can be readily achieved by the incorporation of one or more stabilizer compounds within the environmentally sensitive material.
  • the specific stabilizer materials which have been discussed herein- above are effective to a degree in the prevention of UV degradation of many widely used polymeric materials.
  • such stabilization with the aforementioned materials can apparently result in some alteration in the stabilized polymer properties due to the amount of materials which must be included therein to achieve the desired degree of protection of the host polymer from the degradative agent.
  • R and R' being independently selected from the group consisting of alkyl, hydroxy substituted alkyl, aryl, amino or hydroxy substituted aryl, aralkyl and amino or hydroxy substituted aralkyl;
  • R 1 and R 2 being independently selected from hydrogen, alkyl, aralkyl;
  • R 3 and R 4 being independently selected from from alkyl of 1 to 4 carbon atoms and capable of collectively forming a cycloalkyl substituent;
  • a and A' being independently selected from the group consisting of alkylene of 1 to 12 carbon atoms; and m is 0 - 4 n is 1 - 3.
  • the amount of stabilizer compounds which can effect satisfactory stabilization of ultraviolet light sensitive polymers is in the range of about 0.1 to about 5 parts by weight of stabilizer per 100 parts by weight of polymer.
  • novel compounds of this invention can be routinely prepared using standard equipment, techniques and readily available starting materials.
  • a typical synthesis of such materials stoichiometric quantities of an appropriately substituted piperidone and a primary amine are reacted with one another in an alcoholic medium in the presence of a catalyst such as platinum.
  • the reaction vessel in which such synthesis is carried out is pressurized and hydrogen introduced therein while the temperature of the reaction mass is elevated (preferably to the refluxing temperature of the alcohol). After the consumption of hydrogen gases essentially ceases, the reaction mass is cooled and filtered.
  • the starting materials which can be used in the synthesis of such novel compounds are either commercially available or can be prepared from readily available materials using standard equipment and techniques.
  • piperazine and piperidone is commercially available from Aldrich Chemical Co.
  • Representative piperazine and piperidone reactants which are suitable for use in the synthesis of the compounds of this invention are N,N'-bis (3-aminopro- pyl) piperazine, N,N'-bis (3-aminopropyl) -2, 5-dimethyl piperazine, 2, 2,6, 6-tetramethyl-4-piperidone and 1,2,2,6, 6-pentamethyl-4-piperidone.
  • the primary amines which are suitable for use in the synthesis of the novel compounds of this, invention are readily available from Dow Chemical Co. or Union Carbide Corp.
  • Representative of the amine reactants which are suitable for use in the synthesis of the compounds of this invention are diethylenetriamine, triethylenetetramine, tetraethylene- pentamine, 3,3-diamino-N-methyldipro ⁇ ylamine, 3,3- diamino-N-ethyldipropylamine and 3, 3-diamino-N-pro ⁇ yl- dipropylamine.
  • the reaction is preferably carried out in the presence of a suitable catalyst, such as platinum.
  • Catalyst concentration is preferably in the range of from about 0.01g to 0.10g of 10% Pt on carbon, per 0.1 mole piperidone reactant.
  • novel compounds can be represented by the following structural formulae:
  • R, R' , A, A' , R, , R 2 and m are the same as previously defined.
  • Typical compounds falling within the scope of the foregoing formulae are bis [3-(2, 2, 6, 6-tetramethylpiperidin-4-yl) aminopropyl]methylamine, bis [3-(2, 2, 6,6- tetramethylpiperidin-4-yl) aminopropyl] ethylamine, bis [3- (2,2,6,6-tetramethylpiperdin-4-yl) aminopropyl] propyl amine, N,N*-bis [3- (2, 2, 6, 6-tetramethylpiperidin-4- yl) aminopropyl] piperazine, N,N'-bis [3-(2, 2, 6, 6-tetra- methylpiperidin-4-yl) aminopropyl] -2, 5-dimethylpiperazine, N,N' -bis [3- (2, 2, 6, 6-tetramethylpiperidin-4-yl) amino- propyl] -2,3,5, 6-tetramethylpiperazine, bis [2-(2, 2, 6, 6- tetramethylpi
  • Ultraviolet light sensitive polymers of the compositions of this invention can include any polymeric material that manifests some degradation upon exposure to UV irradiation. Virtually all polymeric materials are sensitive, at least to some degree, to photodegradation by ultraviolet light.
  • photodegradation as used herein with reference to ultraviolet light sensitive polymeric materials, is intended to be inclusive of any photo-induced change in the physical, chemical and/or electrical properties of the polymer or articles prepared therefrom.
  • UV sensitive polymeric materials are the polyurethanes, PVC resins, ABS resins, polystyrene, polyacfylonitrile, polymethacrylate, polycarbonates, phenol-formaldehyde resins, polyepoxides, polyesters, and polyolefins (especially homopolymers and copolymers of polyethylene, polypropylene, ethylene-propylene copolymers, ethylene-vinyl acetate copolymers), and the like.
  • the ultraviolet light sensitive polymers are derived from ⁇ - monoolefin monomers such as ethylene, propylene, isobutylene, 1-butene, 1-pentene, 1-hexene, 4-methyl-l- pentene, and the like.
  • the stabilized polymeric compositions prepared from the above materials can contain, in addition to the stabilizers and polymers described hereinabove, a variety of optional ingredients.
  • Such optional ingredients can include metal oxides, such as zinc, calcium and magnesium oxides; fatty acids, such as stearic, lauric and salts thereof; fillers such as calcium and magnesium carbonate, calcium and barium, sulfonates, aluminum silicates, asbestos, and the like; plasticizers and extenders, such as dialkyl and diaryl organic acids, such as diisobutyl, diisooctyl, diisodecyl and dibenzyl oleates, stearates, sebacates, azelates, phthalates, and the like; ASTM Type 2 petroleum oils, paraffinic oils, castor oil, tall oil, glycerine, and the like; antioxidants, such as 2,6-di-t- butyl-para-cresol, 2,2'-methylene-bis-(4-ethyl-6-t-butyl phenol), 2, 2' -thio-bis-(4-methyl-6-t-butyl phenol), 2, 2'- m
  • antioxidants are the antioxidants.
  • antioxidants can be present within the polymer composition at a concentration within the range of from about 0.1 to about 10 parts by weight per 100 parts by weight polymer, and preferably from about 0.2 to about 5 parts by weight per 100 parts by weight polyer.
  • the phenolic antioxidants are preferred for use in conjunction with the UV stabilizers of this invention.
  • This combination of UV stabilizer and phenolic antioxidants is especially suitable for use in conjunction with polyolefins; that is, in an environment in which the polyolefin is subjected to a plurality of degradative forces, including heat, oxygen and ultraviolet light.
  • the photodegradable polymers of the compositions of this invention can be compounded with the various stabilizers and additives described hereinabove in accord with standard mixing techniques and equipment; such as in a Banbur.y mixer, Henschel mixer, a rubber mill, an extruder mixer or other equivalent device.
  • the various components of such a composition may be physically and intimately blended either in the absence of, or in the presence of, a common solvent; or in a solvent which is capable of dissolving the polymer component of the composition yet substantially incapable of dissolving the stabilizer ingredients.
  • solvents/dispersing agents include hexane or benzene.
  • the dispersing agent (if any) can be removed by selective evaporation and the resultant resin compounded and recovered.
  • the resin compound may thereafter be formed into useful products by a variety of molding techniques.
  • the ultraviolet light stability of the compositions prepared in the above manner can be evaluated by exposing a sample thereof to a Xenon or Carbon arc light in a Weather-Ometer operated at a temperature of about 60°C. Degradation of similarly prepared samples is determined by measurement of the difference in tensile strength after exposure to UV light. Where the tensile strength of the sample is reduced to fifty percent (50%) of its original value, the sample is regarded as degraded.
  • the protocol used in such evaluation is generally recognized as an accepted method for evaluation of photodegradation of plastics and correlate with other more elaborate techniques.
  • Degradation of the sample can also be monitored periodically, by measuring the carbonyl absorption band at 1720cm 1 , using an IR spectrophotometer. The relatively rapid formation of carbonyl sites indicates photodegradation occurring within the sample.
  • This test procedure is also a recognized method for evaluation of the efficacy of such UV stabilizers and is fully described in the open literature, see for example "Photodegradation, Photooxi- dation and Photostabilization of Polymers", by Ranby & Raybeck, John Wiley & Sons, New York City (1975) at page 125 et seq; and U.S. Patent 3,909,493.
  • Photodegradation of the sample can also be visibly manifest as cracking of the sample upon prolonged heating at 180°C. Oxidative degradation and thermal stability of the sample can be verified by monitoring the time required to effect discoloration and/or embrittlement of the sample in a standard aging oven maintained at 149 °C.
  • the concentrate is fractionated under reduced pressure for removal of 2,2,6,6-tetramethyl-4-piperidonol and the desired product isolated from the remaining fraction, boiling point 168 - 172°C @ 0.002mm Hg, total yield 12.9 grams or 72% based upon diethylenetriamine content of the charge. Elemental analysis yields the following results: Calculated for C 22 H 47 N 5 : C, 69.23;H,12.42;N,18.35. Found: C,68.41; H,12.38; N,18.03.
  • the concentrate is fractionated under reduced pressure to remove 2,2,6,6-tetramethyl-4-piperidinol and to collect the desired product which boils at 220°C/0.7 mm Hg.
  • the total weight of the desired product is 12.60 grams (59.2% yield based on triethylenetetramine). Elemental analysis gives the following results:
  • Good-rite 3125 is 3,5- di-tert-butyl-4-hydroxy-hydrocinnamic acid triester with 1,3, 5-tris(2-hydroxyethyl-s- triazine)-2,4,6( IH,3H,5H)-trione.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Hydrogenated Pyridines (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Nouveaux composes, compositions et procedes de stabilisation de polymeres sensibles a la lumiere ultraviolette contre la photodegradation. Les nouvelles amines secondaires et tertiaires de cette invention peuvent etre representees par la formule suivante: (FORMULE) R et R' etant choisis independamment parmi le groupe comprenant un alkyle, un alkyle a substitution hydroxy, un aryle un aryle a substitution hydroxy ou amino, un aralkyle et un aralkyle a substitution hydroxy ou amino; R1 et R2 etant choisis independamment parmi l'hydrogene, un alkyle, l'aralkyle, R3 et R4 etant choisis independamment un alkyle de 1 a 4 atomes de carbone et capables de former collectivement un substituant de cyclo alkyle; A et A' etant choisis independamment parmi le groupe consistant en alkylene de 1 a 12 atomes de carbone; et m a une valeur de 0 a 4, et n de valeur 1 a 3. Les composes ci-dessus sont specialement appropries pour la stabilisation de polyolefines (polypropylene) contre les forces de degradation de la lumiere ultraviolette.
EP19810900159 1979-12-10 1980-11-06 Nouvelles amines secondaires et tertiaires et leur utilisation dans des compositions et dans la stabilisation de polymeres contre la degradation par la lumiere ultraviolette. Withdrawn EP0041555A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10197279A 1979-12-10 1979-12-10
US101972 1979-12-10

Publications (2)

Publication Number Publication Date
EP0041555A1 EP0041555A1 (fr) 1981-12-16
EP0041555A4 true EP0041555A4 (fr) 1982-04-22

Family

ID=22287446

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19810900159 Withdrawn EP0041555A4 (fr) 1979-12-10 1980-11-06 Nouvelles amines secondaires et tertiaires et leur utilisation dans des compositions et dans la stabilisation de polymeres contre la degradation par la lumiere ultraviolette.

Country Status (7)

Country Link
EP (1) EP0041555A4 (fr)
JP (1) JPS56501681A (fr)
BE (1) BE886428A (fr)
BR (1) BR8008958A (fr)
ES (1) ES497599A0 (fr)
GR (1) GR71618B (fr)
WO (1) WO1981001706A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4315859A (en) * 1979-01-15 1982-02-16 Ciba-Geigy Corporation 1,3,5-Triazines containing at least one piperidine radical
DE3530666A1 (de) * 1985-08-28 1987-03-12 Basf Ag Glykolurilderivate und ihre verwendung als stabilisatoren fuer polymere
EP0224720A1 (fr) * 1985-11-01 1987-06-10 The B.F. GOODRICH Company Stabilisants à la lumière comportant des extrémités pipéridines substituées
DE3643892A1 (de) * 1986-12-22 1988-06-30 Basf Ag Glykolurilderivate und ihre verwendung als stabilisatoren fuer polymere
IT1227953B (it) * 1988-12-23 1991-05-14 Ciba Geigy Spa Composti piperidin-triazinici atti all'impiego come stabilizzanti per materiali organici
IT1231329B (it) * 1989-07-28 1991-11-28 Ciba Geigy Spa Composti piperazin piperidinici atti all'impiego come stabilizzanti per materiali organici
US5112979A (en) * 1990-11-29 1992-05-12 Texaco Chemical Company Polyoxyalkyleneamines containing tetraalkylpiperidine functionality and their use as light, heat and oxidation stabilizers
US5204474A (en) * 1991-06-03 1993-04-20 Ciba-Geigy Corporation 2,6-diarylpiperidin-1-yl substituted 2-butene stabilizers

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3937711A (en) * 1973-10-15 1976-02-10 Ciba-Geigy Corporation 4-(carboxamidoethyl) piperidines
CH592129A5 (en) * 1973-10-18 1977-10-14 Ciba Geigy Ag Stabilising organic materials, esp. polymers - against light, oxygen and heat, with piperidine derivs.
US4104248A (en) * 1975-03-21 1978-08-01 Montefibre S.P.A. Polyolefine-based polymeric compositions stabilized by organic polyamines, textile fibers obtained therefrom, and novel organic polyamines

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3106552A (en) * 1960-07-19 1963-10-08 Geschickter Fund Med Res Nu-substituted azaspiranes and azaspirane-diones and processes for their preparation
US3291808A (en) * 1961-08-14 1966-12-13 Parke Davis & Co Naphthalene diamine compounds and methods for their production
US4240954A (en) * 1979-02-26 1980-12-23 American Cyanamid Company Polymers stabilized against degradation by ultraviolet radiation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3937711A (en) * 1973-10-15 1976-02-10 Ciba-Geigy Corporation 4-(carboxamidoethyl) piperidines
CH592129A5 (en) * 1973-10-18 1977-10-14 Ciba Geigy Ag Stabilising organic materials, esp. polymers - against light, oxygen and heat, with piperidine derivs.
US4104248A (en) * 1975-03-21 1978-08-01 Montefibre S.P.A. Polyolefine-based polymeric compositions stabilized by organic polyamines, textile fibers obtained therefrom, and novel organic polyamines

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO8101706A1 *

Also Published As

Publication number Publication date
EP0041555A1 (fr) 1981-12-16
ES8203344A1 (es) 1982-04-01
ES497599A0 (es) 1982-04-01
WO1981001706A1 (fr) 1981-06-25
GR71618B (fr) 1983-06-17
BR8008958A (pt) 1981-10-20
JPS56501681A (fr) 1981-11-19
BE886428A (fr) 1981-04-01

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