US3462249A - Fuel oil compositions containing grafted polymers - Google Patents

Fuel oil compositions containing grafted polymers Download PDF

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US3462249A
US3462249A US627297A US3462249DA US3462249A US 3462249 A US3462249 A US 3462249A US 627297 A US627297 A US 627297A US 3462249D A US3462249D A US 3462249DA US 3462249 A US3462249 A US 3462249A
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ethylene
oil
oils
vinyl
polymers
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Norman Tunkel
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F263/00—Macromolecular compounds obtained by polymerising monomers on to polymers of esters of unsaturated alcohols with saturated acids as defined in group C08F18/00
    • C08F263/02—Macromolecular compounds obtained by polymerising monomers on to polymers of esters of unsaturated alcohols with saturated acids as defined in group C08F18/00 on to polymers of vinyl esters with monocarboxylic acids
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    • C10L1/00—Liquid carbonaceous fuels
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    • C10L1/1625—Hydrocarbons macromolecular compounds
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    • C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
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    • C10M2205/024—Propene
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    • C10M2205/026—Butene
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    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
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    • C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
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    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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    • C10M2209/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an acyloxy radical of saturated carboxylic or carbonic acid
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    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
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    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12

Definitions

  • the present invention relates to the production of ethylene grafted hydrocarbon polymers and copolymers which are particularly useful as pour depressants and flow improvers for hydrocarbon oils, and more especially useful with respect to these properties in compositions of lubricating oils or petroleum middle distillates containing the same.
  • the invention also relates to the production of such polymers, copolymers, and terpolymers, i.e., the ethylene grafted polymers, and their ultimate use in liquid petroleum hydrocarbon oils such as residual fuels or reduced crude oils for improving the aforementioned properties of such liquids.
  • Normally liquid hydrocarbon oils including lubricating oils and petroleum middle distillates such as kerosene, No. 2 heating oils, residual oils, Diesel fuels, and jet fuels, or reduced crude fractions of waxy nature, have,
  • Oils which contain sizeable quantities of waxy components have a tendency to precipitate the wax as large interlocking crystals which trap the fuel or oil into a gel-like structure which has a tendency to markedly increase the viscosity of such fuels and oils upon a lowering of the atmospheric temperature.
  • Such conditions cause the fuel or oil to solidify or tend to have much higher viscosity such that, for all practical purposes, the hydrocarbon oils become nonpumpable, exhibit higher wear qualities to pumps, and, in fact, even become nontransportable.
  • This gel or solidification condition is generally known as the pour point and arises largely by reason of the tendency of the wax crystals to form an interlocking network. This tendency of the crystals to form such networks tends to plug fuel filters, and to increase the wear on pumps handling such products to the point where it becomes impractical at these low ambient temperatures to handle, transport and market such hydrocarbon oils.
  • novel ethylene grafted polymers of the present invention have been found effective in changing the size of the wax crystals which precipitate from the hydrocarbon oils both initially and as the temperature is lowered thus resulting in more crystals of much reduced size than in cases where these novel ethylene grafted polymers are not incorporated into such oils.
  • the polymers per se are, for the most part, already well known and in the past have been employed as additives for hydrocarbon oils.
  • the present invention utilizes these materials as starting materials into which ethylene is incorporated by an ethylene grafting polymerization technique so that the ethylene grafted polymers, by reason of ethylene grafting technique em ployed, thereafter possess the same long chain portions of the polymer and, in addition, possess pending therefrom at numerous points, depending upon the relative activities of the carbon atoms in the alkyl chain, a plurality of polyethylene chains attached thereto so that an increased branchiness in the character of the original polymer as well as an increased number average molecular weight, is achieved.
  • the resultant ethylene grafted polymers exhibit more eflicacious pour point depressant characteristics than do the original polymers while, at the same time, they do not sacrifice combustion qualities in the middle distillate fractions or the desired lubricity and viscosity qualities in the lubricating oil, reduced crude, and heavy oil fractions.
  • the polymers which serve as starting materials from which the ethylene grafted products are produced are of varied nature. They may or may not possess olefinic unsaturation and they have a number average molecular weight between about 800 and about 50,000.
  • the following types of classes of polymers are contemplated as starting materials onto which ethylene may begrafted by a chain transfer type of polymerization reaction:
  • polymeric reactants that may be employed as starting materials are the following: (copolymers are shown thus: monomer A-monomer B) polypropylene, polyisobutylene, 2-ethylhexyl acrylate-methyl arcrylate, n-octenel-isobutylene, propylene-pentene-Z, propylene dilorol fumarate, propylene cetyl maleate, propylene-didodecyl fumarate, propylene-dodecyl methacrylate, isobutylene-di-n-decyl fumarate, n-vinyl pyrrolidone-lauryl methacrylate, n-vinyl pyrrolidone-mixed alkyl acrylates (i.e., cetyl acrylate and octadecyl acrylate, or dodecyl methacrylate, and n-hexyl methacrylate,
  • the resultant ethylene grafted polymers or copolymers are generally viscous, heavy, whitish liquids or semisolids having a number average molecular weight substantially above that of the starting polymer, i.e., between about 800 and about 50,000.
  • a number of patents disclose the method by which the aforementioned polymers and copolymers may be formed and exhibit representative teachings of the methods of producing such polymers which have heretofore been found useful in the treatment of lubricating oils and/or middle distillate fuels. As examples, the following patents are noted: 2,327,705,
  • the same type of free radical polymerization may be employed in the preparation of one type of polymer as well as employed in the grafting of the polymer with ethylene.
  • conventional alkyl, acyl, and aroyl peroxides are employed. These are conventional promoters.
  • benzoyl peroxide dicumyl peroxide, tertiary butyl peroxide, tertiary butyl hydroperoxide, tertiary butyl perbenzoate, lauroyl peroxide, acetyl peroxide, peroxy dicarbamate, dichloro-benzoyl peroxide, and alpha,alpha, azo-di-isobutyro nitrile, etc.
  • the reaction conditions employed are generally as follows: a temperature of between about and about 500 F., depending upon the choice of free radical promoter, and sufiicient pressure to maintain the reaction 1 in a liquid phase and to provide a suflicient concentration of ethylene in solution.
  • the solvent employed may be an aromatic solvent such as benzene, toluene, or the like or it may be, for example, an aliphatic solvent such as carbon tetrachloride, hexane, heptane, or mixtures of the lower aliphatic hydrocarbons.
  • the reaction is carried out for varying periods of time depending upon the type of substrate and the degree of branching desired but usually requires from about 2 to about 8 hours, preferably between about 3 and about 5 hours. Pressures of from 50 or p.s.i.g. up to about 3,000 p.s.i.g. are generally satisfactory although higher pressures may be employed if they are necessary in order to maintain a sufficiently high ethylene concentration and liquid phase conditions. Sufiicient pressure is employed in order to maintain a liquid phase reaction medium. Stainless steel pressure vessels equipped with stirrers are ordinarily employed and in the ethylene grafting reaction the pressure is maintained continuously by the application of ethylene pressure from a suitable source. The reactor is charged with solvent and polymer and brought up to the desired temperature.
  • the desired pressure is generally maintained by means of the introduction of ethylene, either continuously or intermittently, throughout the duration of the reaction.
  • the peroxide in solvent is charged continuously to the reaction vessel.
  • the temperature is maintained between about F. and about 300 F. and the pressure will most generally be adequate if it is maintained between about 400 p.s.i.g. and about 1,200 p.s.i.g.
  • the peroxide is employed in the reaction mixture to the extent of between about 0.05 and about 1.5 wt. percent of the total reaction mixture. This is not a critical amount for amounts outside this range may be employed.
  • the pressure is reduced by flashing or by other means of reducing the pressure and the reactor contents are emptied, stripped of solvent and unreacted reactants either by distillation under vacuum or at atmospheric pressure, after which the ethylene grafted polymer is usually redissolved in a suitable diluent oil for convenience in handling and shipping.
  • a suitable diluent oil for convenience in handling and shipping.
  • the amount of ethylene incorporated into the copolymer by grafting will range between about and about 20 wt. percent based upon the weight of the original polymer or copolymer.
  • ethylene is incorporated to the extent of about wt. percent on the same basis.
  • the polymer so grafted generally has its effectiveness increased over the ungrafted polymer. For example, 0.02% of a particular ungrafted copolymer in any given oil will not depress the pour point of a middle distillate heating oil.
  • the use of the same amount of the ethylene graft of the same copolymer in the same oil will result in the reduction of the pour point to the extent of about 10 to F.
  • the petroleum oil fractions to which these ethylene grafted polymers or copolymers are added are the hydrocarbon middle distillate fuels such as kerosene, No. 2 heating oil, diesel fuels, jet fuels, the residual heating oils, and the reduced crudes obtained from waxy or parafiinic crude oils.
  • the middle distillate fuels generally have a boiling range of between about 250 F. and about 800 F. while the lubricating oil fractions have a boiling range of between about 650 F. and about 1,100 F.
  • the amount of additive employed generally ranges between about 0.01 and about 5.0 wt. percent, and in the case of lubricating oils, the amount of novel additive therein will range between about 0.01 and about 10.0 wt. percent.
  • additives may be employed alone or in combination with other well known additives for hydrocarbon fuel oils or lubricating oils such as other pour depressants, e.g., the commercially available ethylene-vinyl acetate copolymers or other commercially available pour point depressants, viscosity index improvers, corrosion inhibitors, antioxidants, and the like.
  • other pour depressants e.g., the commercially available ethylene-vinyl acetate copolymers or other commercially available pour point depressants
  • viscosity index improvers e.g., the commercially available ethylene-vinyl acetate copolymers or other commercially available pour point depressants
  • viscosity index improvers e.g., the high molecular weight polymers Acryloids and Paraflow, i.e., chlorinated wax-naphthalene condensation products, isobutylene polymers, acrylate or methacrylate polyesters and the like.
  • the corrosion inhibitors are those customarily employed such as the inorganic or organic nitrites, for example, sodium nitrite or lithium nitrite, diisopropyl ammonium nitrite or dicyclohexyl ammonium nitrite, the metallic organic phosphates, for example, calcium or zinc dicyclohexylthiophosphate or the same salts of methyl-cyclohexylthiophosphate; antioxidants such as the commercially available and conventionally used phenols and amines such as octadecylamine, 2,6-di-tertiary-butyl- 4-methyl phenol; or even in association with the extreme pressure additives such as the conventional organic phosphites and phosphates.
  • the inorganic or organic nitrites for example, sodium nitrite or lithium nitrite, diisopropyl ammonium nitrite or dicyclohexyl ammonium nitrite
  • EXAMPLE 1 500 grams of polyisobutylene of about 800 number average molecular weight and 1,125 cc. of benzene were charged to a pressure reactor. 1,100 to 1,150 p.s.i.g. of
  • ethylene was thereafter maintained on the reactor which was heated to 150 C. for 2% hours.
  • 23 wt. percent concentration of di-tertiary butyl peroxide in benzene was added at the rate of 30 cc./hr. throughout this time.
  • the temperature was lowered, the reactor vented, and the product worked up by removing the solvent on a steam bath.
  • 800 grams of ethylene grafted polyisobutylene was obtained. 0.02 wt. percent of this grafted polymer lowered the pour point of at 0 F. pour point heating oil by 15 degrees.
  • EXAMPLE 2 500 grams of polypropylene having a number average molecular weight of 843 was charged to a pressure reactor in 1,125 cc. of benzene and a 23 wt. percent concentration of di-tertiary butyl peroxide in benzene was added thereto at the rate of 30 cc. per hour for 3 hours and 25 minutes, during which time ethylene pressure was maintained on the reactor to the extent above specified. At the end of this time the reactor was cooled and the pressure gradually released. The product was worked up as in Example 1. There was recovered from the reactor mixture 693 grams of ethylene grafted polypropylene having a number average molecular weight of about 975. 0.02% of this grafted polymer lowered the pour point of a 0 F. natural pour point heating oil by 10 degrees.
  • EXAMPLE 3 153.7 grams of a copolymer of 2-ethyl hexyl acrylate and methyl acrylate, and 1,000 grams of benzene were charged to a pressure reactor essentially according to the procedure of Example 1. An ethylene pressure of 1,150 p.s.i.g. was maintained for about 1 /2 hours, during which time 45 cc. of 23.0 wt. percent solution of ditertiary butyl peroxide in benzene were added. 257 grams of ethylene grafted copolymer were obtained. The following table shows the comparative pour potency of the grafted and ungrafted copolymers in a typical heating oil.
  • Natural pour point 0 0.1% ungrafted polymer 5 0.1% grafted polymer -20 As used in this description and accompanying claims, the term polymer is intended to include homopolymers, copolymers, and terpolymers.
  • a composition comprising a major amount of petroleum oil selected from the group consisting of middle distillate fuels, residual fuels and reduced crude oils, and about .01 to about 5 wt. percent of a pour point depressant formed by grafting ethylene onto a hydrocarbon oil soluble polymer of polymerizable, monoolefinically unsaturated organic monomers, said polymers having a number average molecular weight of between about 800 and about 50,000, the grafting reaction being promoted with a free radical polymerization promoter at a temperature of between about F. and about 500 F. under at least sufficient superatmospherie pressure to maintain a liquid phase reaction medium.
  • a composition comprising a major amount of p troleum oil selected from the group consisting of middle distillate fuels, residual fuels and reduced crude oils and about 0.1 to 5.0 wt. percent of a pour point depressant and flowability improver prepared by a process which comprises reacting ethylene with a hydrocarbon oil-soluble polymer having a number average molecular wt.
  • composition as in claim 2 wherein said oil is a distillate fuel oil.
  • composition as in claim 2, wherein said oil is a residual fuel oil.
  • composition as in claim 2 wherein said oil is a reduced crude oil.
  • composition as in claim 2, wherein the hydrocarbon oil-soluble polymer is polypropylene.
  • composition as in claim 2, wherein the hydrocarbon oil-soluble polymer is polyisobutylene.
  • hydrocarbon oil-soluble polymer is a polymer of C to C alkyl ester of acrylic acid.

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US3549535A (en) * 1965-06-24 1970-12-22 Sinclair Research Inc Mineral oils containing a graft polymer of natural rubber and polydiene
US3767460A (en) * 1969-08-08 1973-10-23 Raffinage Co Franc De Method of decreasing the wear of flexible bodies rubbing on a rigid surface
US3776247A (en) * 1967-07-07 1973-12-04 Shell Oil Co Process for the preparation of a crude-oil composition with a depressed pour point
US3807975A (en) * 1968-10-23 1974-04-30 Standard Oil Co Middle distillate fuel oil compositions having improved pumpability
US3868231A (en) * 1971-12-27 1975-02-25 Shell Oil Co Fuel composition
US3947368A (en) * 1971-02-25 1976-03-30 Texaco Inc. Lubricating oil compositions
DE2634033A1 (de) * 1975-07-31 1977-02-10 Rohm & Haas Pfropfcopolymerisate
US4178951A (en) * 1978-10-10 1979-12-18 Texaco Inc. Low pour point crude oil compositions
US4178950A (en) * 1978-10-10 1979-12-18 Texaco Inc. Residual fuel compositions with low pour points
US4862908A (en) * 1986-07-17 1989-09-05 Ruhrchemie Aktiengesellschaft Mineral oils and mineral oil distillates having improved flowability and method for producing same
US4970011A (en) * 1979-05-08 1990-11-13 Kao Soap Company, Ltd. Lubricating oil useful in the rolling of metal and a method for supplying the same
US5035719A (en) * 1988-12-27 1991-07-30 Texaco Inc. Middle distillate containing storage stability additive
US5094764A (en) * 1979-05-08 1992-03-10 Kao Soap Co., Ltd. Method for supplying a lubricating oil composition
US6203583B1 (en) 1999-05-13 2001-03-20 Equistar Chemicals, Lp Cold flow improvers for distillate fuel compositions
US6206939B1 (en) 1999-05-13 2001-03-27 Equistar Chemicals, Lp Wax anti-settling agents for distillate fuels
US6342081B1 (en) 1999-07-13 2002-01-29 Equistar Chemicals, Lp Cloud point depressants for middle distillate fuels
US20030159336A1 (en) * 2002-01-17 2003-08-28 Botros Maged G. Fuel additive compositions and distillate fuels containing same
US20050113266A1 (en) * 2003-10-25 2005-05-26 Clariant Gmbh Cold flow improvers for fuel oils of vegetable or animal origin
US20050126070A1 (en) * 2003-12-11 2005-06-16 Clariant Gmbh Fuel oils composed of middle distillates and oils of vegetable or animal origin and having improved cold flow properties
US20050126072A1 (en) * 2003-12-11 2005-06-16 Clariant Gmbh Fuel oils composed of middle distillates and oils of vegetable or animal origin and having improved cold flow properties
US20050126071A1 (en) * 2003-12-11 2005-06-16 Clariant Gmbh Fuel oils composed of middle distillates and oils of vegetable or animal origin and having improved cold flow properties
US7476264B2 (en) 2003-10-25 2009-01-13 Lariant Produkte (Deutshland) Gmbh Cold flow improvers for fuel oils of vegetable or animal origin
US20100175310A1 (en) * 2007-06-11 2010-07-15 Martyak Nicholas M Acrylic polymer low temperature flow modifiers in bio-derived fuels
US20100237544A1 (en) * 2007-09-28 2010-09-23 Bayer Materialscience Ag Method for producing a deep-drawn film part from a thermoplastic material
JP2013504667A (ja) * 2009-09-14 2013-02-07 ダウ グローバル テクノロジーズ エルエルシー エチレンおよびポリアルケン由来の単位を含むポリマー
CN103740300A (zh) * 2013-12-24 2014-04-23 上海邦中高分子材料有限公司 一种铝塑复合板用高强粘结树脂
US9732220B2 (en) 2013-03-13 2017-08-15 Covestro Llc Polymers and polymer blends with enhanced gloss level

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CN102695735B (zh) 2009-09-14 2014-11-05 陶氏环球技术有限责任公司 包含源于乙烯和硅氧烷的单元的聚合物

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3549535A (en) * 1965-06-24 1970-12-22 Sinclair Research Inc Mineral oils containing a graft polymer of natural rubber and polydiene
US3776247A (en) * 1967-07-07 1973-12-04 Shell Oil Co Process for the preparation of a crude-oil composition with a depressed pour point
US3807975A (en) * 1968-10-23 1974-04-30 Standard Oil Co Middle distillate fuel oil compositions having improved pumpability
US3767460A (en) * 1969-08-08 1973-10-23 Raffinage Co Franc De Method of decreasing the wear of flexible bodies rubbing on a rigid surface
US3947368A (en) * 1971-02-25 1976-03-30 Texaco Inc. Lubricating oil compositions
US3868231A (en) * 1971-12-27 1975-02-25 Shell Oil Co Fuel composition
DE2634033A1 (de) * 1975-07-31 1977-02-10 Rohm & Haas Pfropfcopolymerisate
US4178950A (en) * 1978-10-10 1979-12-18 Texaco Inc. Residual fuel compositions with low pour points
US4178951A (en) * 1978-10-10 1979-12-18 Texaco Inc. Low pour point crude oil compositions
US4970011A (en) * 1979-05-08 1990-11-13 Kao Soap Company, Ltd. Lubricating oil useful in the rolling of metal and a method for supplying the same
US4985158A (en) * 1979-05-08 1991-01-15 Kao Corporation Lubricating oil composition and method for supplying same
US5094764A (en) * 1979-05-08 1992-03-10 Kao Soap Co., Ltd. Method for supplying a lubricating oil composition
US4862908A (en) * 1986-07-17 1989-09-05 Ruhrchemie Aktiengesellschaft Mineral oils and mineral oil distillates having improved flowability and method for producing same
US5035719A (en) * 1988-12-27 1991-07-30 Texaco Inc. Middle distillate containing storage stability additive
US6203583B1 (en) 1999-05-13 2001-03-20 Equistar Chemicals, Lp Cold flow improvers for distillate fuel compositions
US6206939B1 (en) 1999-05-13 2001-03-27 Equistar Chemicals, Lp Wax anti-settling agents for distillate fuels
US6342081B1 (en) 1999-07-13 2002-01-29 Equistar Chemicals, Lp Cloud point depressants for middle distillate fuels
US6673131B2 (en) 2002-01-17 2004-01-06 Equistar Chemicals, Lp Fuel additive compositions and distillate fuels containing same
US20030159336A1 (en) * 2002-01-17 2003-08-28 Botros Maged G. Fuel additive compositions and distillate fuels containing same
US20050113266A1 (en) * 2003-10-25 2005-05-26 Clariant Gmbh Cold flow improvers for fuel oils of vegetable or animal origin
US7476264B2 (en) 2003-10-25 2009-01-13 Lariant Produkte (Deutshland) Gmbh Cold flow improvers for fuel oils of vegetable or animal origin
US7500996B2 (en) 2003-10-25 2009-03-10 Clariant International Ltd. Cold flow improvers for fuel oils of vegetable or animal origin
US7815697B2 (en) 2003-12-11 2010-10-19 Clariant Finance (Bvi) Limited Fuel oils composed of middle distillates and oils of vegetable or animal origin and having improved cold flow properties
US20050126070A1 (en) * 2003-12-11 2005-06-16 Clariant Gmbh Fuel oils composed of middle distillates and oils of vegetable or animal origin and having improved cold flow properties
US20050126072A1 (en) * 2003-12-11 2005-06-16 Clariant Gmbh Fuel oils composed of middle distillates and oils of vegetable or animal origin and having improved cold flow properties
US20050126071A1 (en) * 2003-12-11 2005-06-16 Clariant Gmbh Fuel oils composed of middle distillates and oils of vegetable or animal origin and having improved cold flow properties
US7473284B2 (en) 2003-12-11 2009-01-06 Clariant Produkte (Deutschland) Gmbh Fuel oils composed of middle distillates and oils of vegetable or animal origin and having improved cold flow properties
US20100175310A1 (en) * 2007-06-11 2010-07-15 Martyak Nicholas M Acrylic polymer low temperature flow modifiers in bio-derived fuels
US8236069B2 (en) * 2007-06-11 2012-08-07 Arkema Inc. Acrylic polymer low temperature flow modifiers in bio-derived fuels
US20100237544A1 (en) * 2007-09-28 2010-09-23 Bayer Materialscience Ag Method for producing a deep-drawn film part from a thermoplastic material
US8168110B2 (en) 2007-09-28 2012-05-01 Bayer Materialscience Ag Method for producing a deep-drawn film part from a thermoplastic material
JP2013504667A (ja) * 2009-09-14 2013-02-07 ダウ グローバル テクノロジーズ エルエルシー エチレンおよびポリアルケン由来の単位を含むポリマー
US8987385B2 (en) 2009-09-14 2015-03-24 Dow Global Technologies Llc Interconnected copolymers of ethylene in combination with one other polyalkene
US9732220B2 (en) 2013-03-13 2017-08-15 Covestro Llc Polymers and polymer blends with enhanced gloss level
CN103740300A (zh) * 2013-12-24 2014-04-23 上海邦中高分子材料有限公司 一种铝塑复合板用高强粘结树脂
CN103740300B (zh) * 2013-12-24 2016-01-06 上海邦中高分子材料有限公司 一种铝塑复合板用高强粘结树脂

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