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WO1993005108A1 - Stabilisation de polyols de polyether de polyoxyalkylene - Google Patents

Stabilisation de polyols de polyether de polyoxyalkylene Download PDF

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Publication number
WO1993005108A1
WO1993005108A1 PCT/US1992/007227 US9207227W WO9305108A1 WO 1993005108 A1 WO1993005108 A1 WO 1993005108A1 US 9207227 W US9207227 W US 9207227W WO 9305108 A1 WO9305108 A1 WO 9305108A1
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WIPO (PCT)
Prior art keywords
composition
alkyl
stabilizer
aralkyl
oxidizable
Prior art date
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Ceased
Application number
PCT/US1992/007227
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English (en)
Inventor
Edward L. Wheeler
Lawrence B. Barry
Mark C. Richardson
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.)
Uniroyal Chemical Co Inc
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Uniroyal Chemical Co Inc
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Filing date
Publication date
Application filed by Uniroyal Chemical Co Inc filed Critical Uniroyal Chemical Co Inc
Priority to EP92924451A priority Critical patent/EP0603341A1/fr
Priority to JP5505272A priority patent/JPH06506018A/ja
Publication of WO1993005108A1 publication Critical patent/WO1993005108A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Definitions

  • the present invention relates to the stabilization of polyoxyalkylene polyether polyols and the use of the stabilized polyols in the preparation of polyurethane foam.
  • the invention relates to
  • polyalkylene polyether polyols with antioxidants or stabilizers and the use of stabilized polyols in the preparation of polyurethane foams to inhibit scorch are well known.
  • Polyether polyols, used in the manufacture of slabstock flexible urethane foam are typically stabilized with antioxidant packages consisting of phenolic and amine antioxidants, and may also contain the synergist phenothiazine.
  • United States Patent Nos. 3,567,664 and 3,637,865 disclose polyurethane foams stabilized with a mixture of 2,6-di-tert-butyl-4-methyl phenol [butylated hydroxy toluene (BHT)] and p,p'-dialkyldiphenylamines United States Patent No.
  • United States Patent No. 4,933,374 discloses polyoxyalkylene polyether polyol compositions protected against oxidative degradation with a stabilizing amount of a synergistic mixture of 2,6-di-tert-butyl-4- sec-butyl phenol and a reaction product of
  • United States patent 4,551,493 is concerned with transparent flame-retardant poly(arylether-arylsulfone) molding materials.
  • An example of a heat stabilizer given is a hindered phenol and a diphenylamine/acetone condensate.
  • the final product is used as a flameproofing agent for plastic molding materials.
  • compositions of the instant invention are disclosed but not exemplified as useful in stabilization of the sulfur bearing poly (arylether- arylsulfone) polymers.
  • the cyclic or linear diphenylamine/acetone condensate of US 4,551,493 are used in combination with a poly(2,6-dibrornophenylene 1,4-oxide).
  • the compositions of the instant invention are not halogenated in any manner nor do the stabilized polymer chains contain a sulfur linkage.
  • Antioxidants are used in polyether polyols to protect the polyol from oxidation during the final stages of manufacture; to reduce peroxide formation during storage; and to reduce the possibility of
  • the compounds of this invention are particularly important to the polyol/flexible urethane industry due to the increased concern over chlorofluorocarbons (CFCs) and their deleterious effect on the earth's ozone layer.
  • CFCs chlorofluorocarbons
  • the absence of CFCs places a higher performance requirement on the stabilization system, since the CFCs prevent discoloration, physical scorch and self-ignition of the foam.
  • the stabilizers of the instant invention is comprised of a class of amine stabilizers, known as acridans, which shows efficacy as well as unexpected synergy when combined with traditional amine, phenolic, phenothiazine and phosphite stabilizers in stabilizing polyether polyols for polyurethane flexible foams which may contain flame retardants as well as other non-sulfur contained polymers subject to heat and oxidane
  • Another aspect of this invention concerns a method for the stabilization of polyalkylene polyether polyols against oxidative degradation and the use of such a stabilized polyol together with polyisocyanates to prepare scorch stabilized polyurethane foams.
  • Yet another aspect of this invention concerns a method of stabilizing polyglycols, heat transfer fluids, lubricating additives, and the like using the synergist of this invention with traditional stabilizers to increase the efficacy of- the stabilizer system and enhance the properties of the respective products.
  • the instant invention is directed to the use of:
  • R 1 , R 2 , R 3 , R 4 can be H, C 1 -C 18 alkyl, or C 7 -C 18 aralkyl.
  • R 3 and R 4 can also be aryl, preferably phenyl.
  • acridan as depicted in structure I above will be used hereinafter to refer to the group of compounds structurally represented by (I).
  • the acridan may be optionally combined with an amine stabilizer of the structure II
  • R 5 and R 6 can be H, C 1 -C 18 alkyl, C 7 -C 18
  • R 9 can be C 1 -C 18 alkyl or C 1 -C 18 aralkyl and R 7 and R 8 are C 4 -C 12 alkyl, C 7 -C 12 aralkyl, preferably t-butyl; or optionally combined with a phosphite
  • R 10 and R 11 are independently selected from C 6 -C 18 alkyl, aryl, C 7 -C 18 aralkyl, or C 7 -C 18 alkaryl.
  • stabilizing amines examples include dioctyl diphenylamine, butylated hydroxytoluene, (2,6-di-t-butyl-4-methylphenol),
  • phenothiazine 4,4'-bis(alpha,alpha-dimethylbenzyl) diphenylamine, styrenated diphenylamines, diisobutylated diphenylamines, mixtures of styrenated and diisobutylated diphenylamines, mixtures of styrenated and ⁇ , ⁇ ,dimethylbenzyl diphenylamines, mixtures of butyl, dibutyl, and octyl diphenylamines, dimerized 2,2'-methylene bis-6-t-butyl-p-cresol, 2,6-di-t-butyl 4-sec-butylphenol, tris(nonylphenyl) phosphite,
  • Preferred substituents of Structure I include those when R 1 and R 2 are hydrogen and R 3 and R 4 are alkyl. A more preferred substitution would include R 1 and R 2 as hydrogen and R 3 and R 4 as methyl.
  • a preferred amine compound for the stabilizer package of this invention includes structure II above wherein R 5 and R 6 are ⁇ , ⁇ ,dimethylbenzyl.
  • the stabilizer system containing an acridan along with currently used commercially available stabilizers will contain, from 1 to 50% by weight of the acridan component in the polyether polyol stabilizer system.
  • a preferred range is from 2 to 20% by weight of the acridan component in the polyether polyol stabilizer system.
  • a most preferred range is from 2 to 10% by weight of the acridan component in the polyether polyol stabilizer system.
  • this invention relates to the manufacture of flexible polyurethane slabstock manufactured from polyether polyols stabilized by the compositions described herein.
  • antioxidants considered to be within the scope of this invention include phenothiazine, phosphites, bisphenols, and the like. These type products are well-known and familiar to those skilled in the art. Acridans provide increased performance in systems where simply increasing antioxidant levels shows little or no increase in performance.
  • acridans of Structure (I) are made by an analogous reaction of a p-di-alkylated diphenylamine with a ketone where the alkyl substituents of the DPA are R 3 and R 4 and the ketone is of the form
  • R is C 1 -C 18 alkyl, or aryl, alkaryl (C 7 -C 18 ) or C 1 -C 18 aralkyl of Structure I and other synthesis techniques and routes can be contemplated to produce improved selectivity and yield.
  • AC2 has the following representative structure: R 1 , R 2 are t-octyl, R 3 is phenyl and R 4 is methyl.
  • a di-p-t-octyl-diphenylamine was reacted with acetophenone to form the acridan AC2; in the case of AC3 di-p-t-butyl diphenylamine was reacted with acetophenone.
  • This AC2 and AC3 compounds demonstrated excellent utility although AC1 is slightly superior; therefore, AC1 is highlighted in the subsequent comparisons with commercial control stabilization systems.
  • the acridan component of the stabilizer package was combined with commercially available amine and phenolic stabilizers including dioctyl diphenylamine (abbreviated as dioctyl DPA), 2,6-di-t-butyl-4-methylphenol
  • styrenated/diisobutylated diphenylamine also known as Naugalube 680
  • Table 1 styrenated/diisobutylated diphenylamine
  • antioxidant stabilizer packages Both the commercial and experimental types of stabilizer systems are listed in Table 1. All of the antioxidant packages were loaded into 3,000 average molecular weight polyol at levels typically used by the major polyol producers, ranging from 0.2 to 0.7 weight percent.
  • the polyols used in these tests were selected from the commercially available polyols VoranolTM 3137
  • polyether polyols that were stabilized by these stabilizer systems indicated in Table 1, were tested by differential scanning calorimetry (DSC), thermogravi- metrically analyzed (TGA) and APHA color tested.
  • Thermogravimetric analysis measures the dynamic relationship between the temperature and the mass of a system. By comparing the mass of a sample to that of a controlled system, the temperature at which weight loss is experienced due to evaporation, decomposition, or combustion may be determined.
  • DSC Differential scanning calorimetry
  • Platinum-Cobalt system used follows ASTM D1209. The values on this scale range from 0 (water white) to 300 (cream white). This data is presented because of the importance of color to the polyol manufacturers. The lower values, indicating lightest color, are those most desirable. It can be seen from the data that the addition of
  • synergistic compound of this invention is equal to the
  • thermogravimetric analysis and microwave scorch as well.
  • the small hand-mixed foam samples were made by the procedure below, and is typical of formulations used by the polyol manufacturers.
  • a premix of 10.0 grams of water, 0.30 grams of an amine catalyst (Dabco 33-LV sold and trademarked by Air Products & Chemicals) and 2.0 grams of a surfactant (L-5810, a tin catalyst sold by Union Carbide) was added to 200 grams of a 3000 average molecular weight polyether polyol which had minimal initial stabilization (100 ppm BHT) but also containing the stabilizer package indicated in Table 1.
  • the amine catalyst Dabco 33-LV sold and trademarked by Air Products & Chemicals
  • a surfactant L-5810, a tin catalyst sold by Union Carbide
  • formulation may also contain a flame retardant as used by foam manufacturers. These flame retardants are typically chlorinated, chlorinated and brominated or brominated phosphates. The mixture was stirred for five seconds in a high speed Lightning Mixer. Then 0.40 grams of tin catalyst (stannous octoate in
  • Examples 1 and 2 demonstrate superior performance as compared to comparative Examples A-D.
  • the microwave scorch test is a rapid and
  • a microwave oven is used to uniformly heat the foam bun by radiant energy rather than by conduction of heat. This promotes uniform heating of the small foam bun resulting in reproducible scorch values.
  • the formulation used to prepare the foam buns is given above, and is typical of the formulations used in the industry.
  • the formulation was prepared, it was poured into a 10" x 10" x 5" cardboard box and allowed to rise. Five minutes after the appearance of bubbles on the surface of the foam, the sides of the box are pulled away from the foam bun and immediately placed into a preconditioned microwave oven for 5 minutes and 30 seconds at 60% power.
  • the microwave oven is
  • microwave for each bun tested to maintain a constant temperature and humidity within the microwave during testing.
  • the foam bun Upon removal of the foam bun from the microwave oven, it is placed into an air circulating oven for 3 minutes at 125°C to cure the skin of the bun. Upon removal from the air circulating oven, the foam sample was cut in half, perpendicular to the rise of the foam and inspected for degree of scorch. A one-inch thick slice is cut from the center of each bun and analyzed via a Hunter Lab Colorimeter, Model D25M/L.
  • Example D provides the highest scorch protection of the commercial systems evaluated, while Example 1 provides a slight increase in scorch protection over the Example C, while Example 2 provides a sizeable increase in scorch protection over comparative Example D.
  • the acridans of the invention may be used in a wide variety of polymers and long chain hydrocarbons which do not contain sulfur linkages in the chains. These may include polyolefins, petroleum based oils, lubes and greases as well as polyalkylene glycols, preferably polyethylene glycols and methoxy polyethylene glycols such as the Carbowax family of products (trademarked and marketed by Union Carbide Chemical and Plastics
  • Various stabilization systems including several containing the acridan synergists of this invention, were evaluated in polyglycol.
  • the polyglycol used was P-2000 (a product of Dow Chemical) and the stabilizers employed included the comparative control, BHT,

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Abstract

L'invention concerne l'utilisation d'un composé acridan de structure (I) en tant que stabilisateur, et de préférence combiné à des stabilisateurs à base d'amine empêchée, de phénol ou de phosphite pour stabiliser les polyols de polyéther pour la préparation de mousses flexibles de polyuréthane et comme stabilisateurs pour les polyglycols, les fluides de transfert de chaleur et les additifs lubrifiants.
PCT/US1992/007227 1991-09-09 1992-08-26 Stabilisation de polyols de polyether de polyoxyalkylene Ceased WO1993005108A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP92924451A EP0603341A1 (fr) 1991-09-09 1992-08-26 Stabilisation de polyols de polyether de polyoxyalkylene
JP5505272A JPH06506018A (ja) 1991-09-09 1992-08-26 ポリオキシアルキレン　ポリエーテル　ポリオールの安定化

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US75674591A 1991-09-09 1991-09-09
US756,745 1991-09-09

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WO1993005108A1 true WO1993005108A1 (fr) 1993-03-18

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JP (1) JPH06506018A (fr)
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Cited By (1)

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Publication number Priority date Publication date Assignee Title
CN103868913A (zh) * 2014-02-11 2014-06-18 中生北控生物科技股份有限公司 碱性磷酸酶的酶促化学发光底物液

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5505016B2 (ja) * 2010-03-24 2014-05-28 東洋インキＳｃホールディングス株式会社 インク組成物、インクジェット記録方法、及び印刷物
JP6191244B2 (ja) * 2013-05-30 2017-09-06 旭硝子株式会社 ポリマー分散ポリオール組成物の製造方法および引火点を上昇させる方法

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US3003995A (en) * 1960-07-18 1961-10-10 Allied Chem Stabilized polycaproamide compositions
DE1163829B (de) * 1960-12-09 1964-02-27 Geigy Ag J R Verfahren zum Stabilisieren organischer Stoffe gegen Oxydation durch Sauerstoff
US3406144A (en) * 1965-02-17 1968-10-15 Ici Ltd Stabilised olefin polymer compositions
EP0223000A2 (fr) * 1985-10-21 1987-05-27 Allied Corporation Additifs dans l'apprêt de cordes de Polyester pour pneus pour réduire la pénétration du trempage
US4794126A (en) * 1988-05-02 1988-12-27 Akzo America Inc. Reduction of discoloration in flame retarded polyurethane foams

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3003995A (en) * 1960-07-18 1961-10-10 Allied Chem Stabilized polycaproamide compositions
DE1163829B (de) * 1960-12-09 1964-02-27 Geigy Ag J R Verfahren zum Stabilisieren organischer Stoffe gegen Oxydation durch Sauerstoff
US3406144A (en) * 1965-02-17 1968-10-15 Ici Ltd Stabilised olefin polymer compositions
EP0223000A2 (fr) * 1985-10-21 1987-05-27 Allied Corporation Additifs dans l'apprêt de cordes de Polyester pour pneus pour réduire la pénétration du trempage
US4794126A (en) * 1988-05-02 1988-12-27 Akzo America Inc. Reduction of discoloration in flame retarded polyurethane foams

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103868913A (zh) * 2014-02-11 2014-06-18 中生北控生物科技股份有限公司 碱性磷酸酶的酶促化学发光底物液

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EP0603341A1 (fr) 1994-06-29
JPH06506018A (ja) 1994-07-07

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