WO2002062895A1 - Composition de polyamide/polyisobutylene et procede de preparation de cette derniere - Google Patents

Composition de polyamide/polyisobutylene et procede de preparation de cette derniere Download PDF

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Publication number
WO2002062895A1
WO2002062895A1 PCT/CZ2002/000007 CZ0200007W WO02062895A1 WO 2002062895 A1 WO2002062895 A1 WO 2002062895A1 CZ 0200007 W CZ0200007 W CZ 0200007W WO 02062895 A1 WO02062895 A1 WO 02062895A1
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pib
polyamide
polyisobutylene
conh
vol
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PCT/CZ2002/000007
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English (en)
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Ludek Toman
Ivan Kelnar
Petr Vlcek
Miroslav Janata
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Ústav Makromolekulární Chemie Akademie Ved Ceske Republiky
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Publication of WO2002062895A1 publication Critical patent/WO2002062895A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J177/00—Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Adhesives based on derivatives of such polymers
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • C08L23/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J177/00—Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Adhesives based on derivatives of such polymers
    • C09J177/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J177/00—Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Adhesives based on derivatives of such polymers
    • C09J177/06—Polyamides derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/08—Polymer mixtures characterised by other features containing additives to improve the compatibility between two polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/06—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond

Definitions

  • the invention concerns a polyamide/polyisobutylene composition, in particular the composition containing polyisobutylene functionalized with isocyanate and subsequently with a lactam and/or amide, and the method of its preparation.
  • Polyisobutylenes are materials highly resistant to chemicals including sulphuric acid. With the development of synthesis of block copolymers or reactive polymers, polyisobutylenes had resisted functionalization for a long time. In the early 1980's only, telechelic ⁇ , ⁇ -dihydroxypolyisobutylenes (HO-PIB-OH) were prepared by controlled cationic polymerization and consecutive multistep syntheses (B. Ivan, J. P. Kennedy, N.S.C. Chang, J. Polym. Sci., Polym. Chem. Ed. 18, 3177 (1980)).
  • Telechelic dihydroxypolyisobutylenes became starting materials for preparation of other reactive polyisobutylenes: for example, HO-PIB-OH was converted to PIB bisurethanes by the reaction of HO-PIB-OH with excess toluene diisocyanate ( ⁇ CO/OH -10/1).
  • ⁇ CO/OH -10/1 excess toluene diisocyanate
  • multistep syntheses going from ⁇ , ⁇ -dichloropolyisobutylene J. P. Kennedy, B. Ivan, Designed Polymers by Carbocationic Macromolecular Engineering, Theory and Practice, Hanser Publisher, New York 1991, p. 178) require thorough purification of intermediates and removing reactants and, in addition, only the functional end groups are exchanged, while the PIB backbone remains unchanged.
  • polyamides found use as a fibre material and, for the same reason, in machinery as a construction plastic
  • polyamides also have a number of drawbacks. All polyamides are hygroscopic, the sorbed water content being variable depending on the air humidity. Their water sorption depends on the concentration of polar ⁇ HCO groups in the polymer. These circumstances must be considered in application of polyamides because, as a consequence, mechanical properties such as tensile strength and toughness as well as the dimensions of products change. Hence, they are not applicable in cases where dimension precision is required. To improve these unfavourable properties, blends of polyamides and polyolefms are mostly prepared, which must be compatibilized using appropriate compatibilizers to achieve good mechanical properties. Examples of such blends are:
  • Polyethylene (PE)/PA 6 L.A. Utracki, M. M. Dumoulin, P.Toma, Polym. Eng. Sci. 26, 34, 1986
  • polypropylene (PP)/PA 6 B. Liang, J.L. White, J.E. Spraiell, B. C. Goswami, J. Appl. Polym. Sci. 28, 2011, 1983
  • compatibilized maleic anhydride- grafted PP/PA 6 F. Ide, A. Hasegawa, J. Appl. Polym. Sci. 18, 963, 1974
  • ethylene- methacrylic acid copolymer/PA6 W.J. Macknight, R.W. Lenz, P. N. Musto, R.J. Somani, Polym.
  • the subject of the present invention is a polyamide/polyisobutylene based composition consisting of a polyamide/polyisobutylene and/or a copolyamide/polyisobutylene blend and a compatibilizer and/or of a polyamide/compatibilizer and/or copolyamide/compatibilizer whereby the compatibilizer is polyisobutylene functionalized with isocyanate groups and, subsequently, with lactam and/or amide, containing in the chain at least one structure unit of general formula I or II
  • -NHCONHCOR' and/or Y groups are linked to the benzene ring directly or through a linear or branched alkyl group R with 1-10 carbon atoms, R' is an aliphatic or aromatic group, Y is a cyclic lactam grouping
  • the polyamide phase in the composition according to the present invention is a high-molecular-weight compound containing in the main chain -CONH- groups, which occur in the arrangements a, b and c.
  • the structures can be prepared by polycondensation of diamines and dicarboxylic acids such as hexamethylenediamine and adipic acid (PA6/6), polycondensation of amino acids such as 11-aminoundecanoic acid or mixed products (c), or by polymerization of cyclic lactams with 4-12 carbon atoms such as 2- pyrrolidone, hexano-6-lactam and dodecano-12-lactam.
  • diamines and dicarboxylic acids such as hexamethylenediamine and adipic acid (PA6/6)
  • polycondensation of amino acids such as 11-aminoundecanoic acid or mixed products (c)
  • cyclic lactams with 4-12 carbon atoms such as 2- pyrrolidone, hexano-6-lactam and dodecano-12-lactam.
  • the polyisobutylene phase in the composition according to the invention is an isobutylene homopolymer or copolymer, with advantage polyisobutylene-c ⁇ -polyiso- prene and polyisobutylene -co-polystyrene.
  • the functionalized polyisobutylenes used as compatibilizers have molecular weights 600 - 200 000 ( fell) and functionality 1-30 (F).
  • the compatibilizer content in polyamide or copolyamide/polyisobutylene blends ranges from 1 to 20 vol. %, with advantage from 2 to 10 vol. % and its content in the blends with polyamide or copolyamide alone is 1-99 vol. %.
  • the polyisobutylene content in polyamide or copolyamide/polyisobutylene blends is 5-95 vol. %.
  • the further object of the present invention is the method of preparation of the composition, which consists in performing compatibilization and mixing of polymer blends in the temperature range of from 150 to 300 °C, preferably at 240 to 260 °C.
  • the mixing and compatibilization of polymer blends according to the invention is performed in the presence of tin compounds such as dibutyltin dilaurate or dibutyltin diacetate in concentrations of 0.01-0.08 vol. %.
  • the compatibilizers are prepared by the procedure in which first the copolymerization of IB with 3-isopropenyl- ⁇ , ⁇ -dimethylbenzyl isocyanate is performed at a temperature below -10 °C in the presence of a Lewis acid, such as tin tetrachloride.
  • TSA triethylamine
  • the reaction of the isocyanate groups with linear or cyclic amides (lactams) is finally performed at a temperature above 60 °C, or the formed PIB-(NCO) n is directly dosed to the lactam or amide melt.
  • the molar ratio of the tertiary amine to the total concentration of the Lewis acid in the reaction mixture is 1-10 3 , preferably 5 and the molar ratio amide/isocyanate groups is 1-10 3 , with advantage 5.
  • the reaction with amides is performed either in high- boiling solvents or in their mixtures having a boiling point higher than 60 °C, in which both PIB-(NCO) n and amide are soluble, with advantage in toluene or in the amide melt.
  • Polyisobutylenes functionalized with isocyanate and subsequently with lactam or amide with molecular weights M n ranging from 600 to 200 000 are oily, pasty, rubber-like or solid.
  • Fig. 1 Morphology of a PA6/PIB blend prepared according to Example 1 (80/20 vol. %;
  • Fig. 2 The same blend but containing a compatibilizer (PIB-K) in a concentration of 3 vol. % (J, Table 1) and 5 vol. % (K, Table 1) with a distinctly finer phase structure.
  • PIB-K compatibilizer
  • n Molecular weights ( n ) of the products were determined by GPC in tetrahydrofuran (THF), the structure of products was analyzed by NMR and IR spectroscopy. The functionality (E) was calculated from ⁇ NMR spectra of products.
  • the first step of the synthesis i.e. the preparation of PIB-(NCO) n ( n , F) was checked by transformation of NCO groups in samples to urethanes by the reaction with methanol using dibutyltin dilaurate as catalyst according to Czech Patent Application PN 1998-1931.
  • PA/PIB, PA/PIB/compatibilizer and PA/compatibilizer blends were usually prepared by 10 min mixing at 250 °C in a laboratory discontinuous Brabender kneader at 50 rpm/min with the W50EH kneading chamber. Mechanical testing of samples was performed in the dry state, immediately after workup. Pieces for Instron 6025 strength tests were prepared after cooling and disintegration by injection molding at 260 °C Type L pieces with a very sharp notch were used for impact tensile toughness tests according to DIN 53448.
  • PIB-(NCO.Ln) n To a mixture of IB (0.53 mol), IDBI comonomer (0.04 mol) and dichloromethane (40 ml) was added tin tetrachloride (0.015 mol) in the temperature range from -50 to -70 °C.
  • the copolymerization gave a yield of 30 g of PIB-(NCO) 5 with functionality ranging from 4 to 6.
  • the reaction was stopped by addition of TEA (0.14 mol) and 80 ml of toluene while stirring. Then the isocyanate groups were reacted with hexano-6-lactam
  • Ln6 (0.133 mol) was dosed into the reactor in a toluene solution (150 ml) and the mixture was refluxed for 10 h. The product was isolated by precipitation of the toluene solution into excess of methanol and dried in vacuo at 40 °C for 5 days. The product,
  • PIB-(NCO.Ln6) n with functionality F-5 and molecular weight ca. 8000 (M n ) was used as compatibilizer (PIB-K) for preparation of composition PA6/PIB/PIB-K.
  • the blends of the following compositions (DBSnDL is dibutyltin dilaurate) were mixed for 10 min:
  • Sn is DBSnDL, ⁇ - stress at break, ⁇ - strain at break, E - Young modulus, a t - toughness (impact tensile strength); measurements were performed at laboratory temperature ( ⁇ 22 °C).
  • the results in Table 1 show an increase in strain of almost one order due to compatibilizer PIB-K when comparing the same blends B and J. It can be also observed that the toughness of the material (F, G, I) increases with increasing content of PIB-K in the composition almost two times (K) compared with the original PA6 (A).
  • the copolymerization was performed up to the yield -30 g of PIB-(NCO) 9 with functionality ranging from 8 to 10.
  • the reaction was stopped by addition of TEA (0.14 mol) and 80 ml of toluene while stirring. Then the isocyanate groups were reacted with 0.133 mol of hexano-6-lactam (Ln6) or 2-pyrrolidone.
  • PIB(NCO.Ln6) 9 and PIB(NCO.Ln4) 9 of molecular weights -18 000 (M n ) were purified and dried by the procedure according to Example 1 and then used as compatibilizers (PIB-K) for preparation of compositions PA6/PIB (-80/20 vol. %)/PIB-K.
  • the compositions containing 40 g PA6, 7.5 g PIB, B50 and 1.5 g PIB-K had the following mechanical properties: ⁇ - 46 MPa, ⁇ - 120 %, E - 1210 MPa, a t - 60 kJ.m "2 .
  • Example 3 The synthesis of isocyanate-functionalized PIB was carried out by the procedure according to Example 1. The product was dosed into the lactam Lnl2 melt and subsequently isolated by precipitation into methanol. After purification and drying, PIB(NCO.Lnl2) 5 of molecular weight 10 000 (M n ) was used as compatibilizer for composition PA6/PIB (-80/20 vol. %)/PIB-K.
  • composition containing 40 g PA6, 7.5 g PIB, B50, 1.5 g PIB-K, and 0.03 g DBSnDL showed the following mechanical properties: ⁇ ⁇ 48 MPa, ⁇ ⁇ 115 %, E ⁇ 1150 MPa, a t - 55 kJ.m "2 .
  • Compatibilizer PIB-K was synthesized according to Example 3 and used for preparation of PA6/copolymer IB-IP (-80/20 %)/PIB-K blend.
  • the composition containing 40 g PA6, 6.5 g IB-IP copolymer, and 2.5 g PIB-K showed the following mechanical properties: ⁇ ⁇ 50 MPa, ⁇ ⁇ 85 %, E ⁇ 1250 MPa, a t ⁇ 61 kJ.m "2 .
  • PA6/6 were as follows: ⁇ ⁇ 72 MPa, ⁇ -190 %, E -1475 MPa, a_ -35 kJ.m ' -2
  • compositions (a) 48.5 g PA6 and 1.5 g PIB-K and (b) 47.5 g PA6 and 2.5 g PIB-K showed the following mechanical properties: (a) ⁇ ⁇ 72.4 MPa, ⁇ -150 %, E -1680 MPa, ⁇ t ⁇ 23.4 kJ.m "2 ; (b) ⁇ -71.2 MPa, ⁇ -160 %, E ⁇ 1540 MPa, ⁇ t ⁇ 30.4 kJ.m '2 .

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyamides (AREA)

Abstract

La présente invention concerne une composition de polyamide/polyisobutylène qui est formée d'un mélange de polyamide et/ou de copolyamide/polyisobutylène et d'un agent de compatibilisation et/ou d'un mélange de polyamide ou de copolyamide et d'un agent de compatibilisation dans lequel l'agent de compatibilisation est du polyisobutylène fonctionnalisé avec de l'isocyanate et ensuite avec un lactame et/ou un amide contenant dans la chaîne au moins une unité de structure comprenant un groupe représenté par la formule I ou II situé dans le groupe terminal ou sur la chaîne. Dans les formules I et II, Z représente H ou CH3. Le groupe réactif NHCONHCOR' et/ou Y est lié au cycle benzène soit directement soit par l'intermédiaire d'un groupe alkyle R linéaire ou ramifié comprenant entre 1 et 10 atomes de carbone, R' représente un groupe aliphatique ou aromatique, Y représente un groupe lactame, où n est compris entre 3 et 11. Pour préparer lesdites compositions selon l'invention on mélange des mélanges polymères à des températures qui sont comprises entre 150 et 300 °C et qui se situent de préférence entre 240 et 260 °C. Formules I et II
PCT/CZ2002/000007 2001-02-09 2002-02-07 Composition de polyamide/polyisobutylene et procede de preparation de cette derniere WO2002062895A1 (fr)

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CZ2001528A CZ291312B6 (cs) 2001-02-09 2001-02-09 Kompozice na bázi směsi polyamid/polyizobutylen a způsob její přípravy
CZPV2001-528 2001-02-09

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017216023A1 (fr) 2016-06-15 2017-12-21 Basf Se Agent antichoc à base de polyisobutylène pour polyamides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5234993A (en) * 1991-11-08 1993-08-10 E. I. Du Pont De Nemours And Company Process for making polyamide/polyolefin blends having superior improved toughness and stiffness
US5700412A (en) * 1993-11-01 1997-12-23 E. I. Du Pont De Nemours And Company Process for making laminar articles
JPH11302479A (ja) * 1998-04-20 1999-11-02 Nichirin Co Ltd 架橋性液状樹脂およびポリアミドを含む組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5234993A (en) * 1991-11-08 1993-08-10 E. I. Du Pont De Nemours And Company Process for making polyamide/polyolefin blends having superior improved toughness and stiffness
US5700412A (en) * 1993-11-01 1997-12-23 E. I. Du Pont De Nemours And Company Process for making laminar articles
JPH11302479A (ja) * 1998-04-20 1999-11-02 Nichirin Co Ltd 架橋性液状樹脂およびポリアミドを含む組成物

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017216023A1 (fr) 2016-06-15 2017-12-21 Basf Se Agent antichoc à base de polyisobutylène pour polyamides
US10731035B2 (en) 2016-06-15 2020-08-04 Basf Se Impact modifier based on polyisobutane for polyamides

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CZ291312B6 (cs) 2003-01-15

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