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WO1999046334A1 - Melanges miscibles multiconstituants de nylons a proprietes ameliorees - Google Patents

Melanges miscibles multiconstituants de nylons a proprietes ameliorees Download PDF

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Publication number
WO1999046334A1
WO1999046334A1 PCT/US1999/004693 US9904693W WO9946334A1 WO 1999046334 A1 WO1999046334 A1 WO 1999046334A1 US 9904693 W US9904693 W US 9904693W WO 9946334 A1 WO9946334 A1 WO 9946334A1
Authority
WO
WIPO (PCT)
Prior art keywords
nylon
copolymer
weight
composition
amount
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.)
Ceased
Application number
PCT/US1999/004693
Other languages
English (en)
Inventor
Yash P. Khanna
Eric D. Day
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.)
Honeywell International Inc
Original Assignee
AlliedSignal Inc
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 AlliedSignal Inc filed Critical AlliedSignal Inc
Priority to BR9908698-0A priority Critical patent/BR9908698A/pt
Priority to JP2000535705A priority patent/JP2002506109A/ja
Priority to EP99911086A priority patent/EP1062277A1/fr
Priority to AU29813/99A priority patent/AU2981399A/en
Priority to KR1020007010034A priority patent/KR20010041775A/ko
Priority to CA002323204A priority patent/CA2323204A1/fr
Publication of WO1999046334A1 publication Critical patent/WO1999046334A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; 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
    • C08L2203/00—Applications
    • C08L2203/16—Applications used for films
    • 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
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group

Definitions

  • EP Patent 408,390 discloses the use of any polyamide, any copolyamide, or a mixture of polyamides along with amorphous polyamide or a copolyamide.
  • Japanese patent 115,4752 discloses films based on mixtures of an aliphatic polyamide and a partially aromatic amorphous polyamide along with EVOH.
  • AU Patent 8825700 discloses an aliphatic polyamide, e.g., nylon 6 or N6/66 copolymer and an amorphous polyamide. All of these likewise do not teach random copolymers of nylons in certain proportions to form a homogenous, miscible phase composition according to the invention.
  • patents 4,647483; 4,665135 and 4,683170 show blends ofN6 plus a copolymer of N6/N66 or N6/N12 rich in N6 such that the overall blend contains 2.5- 10%, of N66 or N12.
  • the present invention is more effective than the blends of these patents, since more N66 can be incorporated without adverse effects on homogeneity.
  • the invention provides method for producing a uniformly blended semi- crystalline nylon composition which comprises:
  • the invention allows one to incorporate multi-component polyamides, e.g., N66, N12, and amorphous nylons into N6, without observing non-homogeneity in either crystalline or amorphous phase as determined by DSC.
  • multi-component polyamides e.g., N66, N12, and amorphous nylons into N6, without observing non-homogeneity in either crystalline or amorphous phase as determined by DSC.
  • Miscibility 0 in blends traditionally has implied one homogenous amorphous phase but the crystalline phases always reveal their characteristic T m 's.
  • this invention provides multi-component miscible blends with just one amorphous phase and just one crystalline phase, as determined by DSC.
  • Figure 1 shows a graph of the melting pattern of melt blended nylon films.
  • Figure 3 shows a graph of the melting pattern of nylon films based on nylon 6 homopolymer plus nylon 6/nylon 66 (84/16) random copolymer blends.
  • Figure 6 shows a graph of the melting pattern of nylon films based on nylon 6 homopolymer plus nylon 6/nylon 66 (75/25) random copolymer blends.
  • Figure 7 shows a graph of the melting pattern of nylon films.
  • the intensity of the second melting peak is determined by known DSC methods. Such methods include analyzing a film to be tested after drying at 25 °C - 45 °C under vacuum for several hours. The intensity of the major and any minor peaks in DSC are determined by heat of fusion integrated over the melting ranges of the individual peaks. Preferably the composition has only one melting point and no other melting point at all.
  • the composition when the nylon components are blended in a first proportion, the composition has a larger difference between its melting temperature and its crystallization temperature than each of nylon homopolymer A and the copolymer.
  • the nylon composition when the nylon components are blended in a second proportion, the nylon composition has a melting temperature which is about equal to the melting temperature of the nylon homopolymer A.
  • a melting temperature which is about equal to the melting temperature of the nylon homopolymer A means within about + 5 °C of the melting temperature of the nylon homopolymer A.
  • the first component of the inventive composition is a semi-crystalline homopolymer of nylon A which may be comprised of any semicrystalline polyamide homopolymer.
  • Polyamides suitable for use in this invention as semi-crystalline homopolymer of nylon A include aliphatic polyamides or aliphatic/aromatic polyamides.
  • aliphatic polyamides are polyamides characterized by the presence of recurring carbonamide groups as an integral part of the polymer chain which are separated from one another by at least two aliphatic carbon atoms.
  • Illustrative of these polyamides are those having recurring monomeric units represented by the general formula:
  • R 2 and R 3 are different and are alkylene groups having at least 2 carbon atoms, preferably having from 2 to about 12 carbon atoms, or arylene, preferably substituted or unsubstituted phenylene,
  • the nylon composition may further contain an optional non-crystalline, non-crystallizable, amorphous nylon component C.
  • Amorphous nylons are well known in the art and are available commercially. Amorphous nylons are typically prepared by the reaction of at least one diamine with at least two different diacids. The result is a non-crystallizable nylon having no determinable melting point. Amorphous nylons are available as Grivory 21 available from EMS of Switzerland and Zytel amorphous nylon from DuPont.
  • the amount of nylon homopolymer A ranges from about 30 % to about 99 % based on the weight of the blended nylon composition, preferably from about 35 % to about 85 % and more preferably from about 40 % to about 60 % based on the weight of the blended nylon composition.
  • the amount of the copolymer of nylon A with nylon B ranges from about 1 % to about 70 % based on the weight of the blended nylon composition, preferably from about 15 % to about 65 % and more preferably from about 40 % to about 60 % based on the weight of the blended nylon composition.
  • the amount of nylon A in the copolymer ranges from about 70 % to about 95 % based on the weight of the copolymer, preferably from about 70 % to about 90 % based on the weight of the
  • an amorphous nylon When included in the first embodiment of the invention, it is present in the overall composition an amount of from about 1 % to about 30 %, preferably from about 2 % to about 25 % and more preferably from about 5 % to about 20 % based on the weight of the blended nylon composition.
  • the nylon composition also has a single melting temperature.
  • the melting temperature is about equal to the melting temperature of nylon homopolymer A.
  • the amount of nylon homopolymer A ranges from about 30 % to about 99 % based on the weight of the blended nylon composition, preferably about 35 % to about 85 % and more preferably ranges from about 40 % to about 60 % based on the weight of the blended nylon composition.
  • the amount of the copolymer of nylon A with nylon B ranges from about 1 % to about 70 % based on the weight of the blended nylon composition, preferably from about 65 % to about 15 % and more preferably from about 60 % to about 40 % based on the weight of the blended nylon composition.
  • the blend may contain additives which are conventionally used in nylon compositions.
  • additives are pigments, dyes, slip additives, fillers, nucleating agents, plasticizers, lubricants, reinforcing agents, antiblocking agents, stabilizers and inhibitors of oxidation, thermal stabilizers and ultraviolet light stabilizers.
  • such may be present in an amount of about 10% or less based on the weight of the composition.
  • the composition may be formed by dry blending solid particles or pellets of each of the nylon components and then melt blending the mixture at a temperature of at least the melting point of the nylon A homopolymer. Typical melting temperatures range from about 175 °C to about 260 °C, preferably from about 215 °C to about 225 °C, and more preferably from about 220 °C to about 223 °C (for nylon 6). Blending may take place in any suitable vessel such as an extruder, a roll mixer, or the like. Blending is conducted for a period of time required to attain a substantially uniform blend. Such may easily be determined by those skilled in the art. If desired, the composition may be cooled and cut into pellets for further processing, or it may be formed into films and optionally uniaxially or biaxially stretched by means well known in the art.
  • composition produced according to the present invention are found to form extremely uniform films.
  • the upper temperature in DSC was changed to about 300 °C.
  • the T m reported in the examples is the one obtained upon initial heating cycle, i.e., corresponding to the "as received films" cast under the same conditions.
  • Super-cooling is reported as the difference between the reheat cycle T m and T cc ,i.e., corresponding to the heat history imposed prior to the cooling cycle.
  • the T cc cooling curve representing the crystallizability of a particular sample during the 10 °C / minute cooling cycle, was integrated to obtain the heat of crystallization (DH f , J/g ).
  • a DH f 230 J/g for 100% crystalline nylon 6, was used to calculate the crystallinity developed (Close , % ) during the 10 °C / minute cooling scan.
  • DHf 188 J/g, was used. The temperature and DHf calibrations, were assured through a two-point calibration using indium
  • nylon 6 [8207, AlliedSignal], nylon 6(95)/nylon 66(5) [AlliedSignal], nylon 6 (85)/nylon 66(15) [AlliedSignal], nylon 6(80)/nylon 66(20) [AlliedSignal], nylon 6 (70)/nylon 66 (30) [AlliedSignal], nylon 6
  • example 1 The procedure of example 1 is repeated except using commercially available random copolymers of nylon 6/nylon 66 in the proportions indicated in Table 2. These are produced by copolymerizing the nylon 6 and nylon 66 monomeric starting materials. A well known, if not the only
  • a nylon 6/nylon 66 (50/50) copolymer would be made by a polymerization reaction of caprolactam (i.e., monomer for nylon 6) and hexamethylenediamine-adipic acid salt (i.e., monomer for nylon 66 ) in a 50 : 50 proportion.
  • caprolactam i.e., monomer for nylon 6
  • hexamethylenediamine-adipic acid salt i.e., monomer for nylon 66
  • the DT for nylon 6 is 38.4 °C ( ⁇ 0.4 ) and this gradually increases to 46.6 °C ( ⁇ 0.3 ) with the addition of 25%> of nylon 66 component.
  • Example 1 is repeated except the compositions are physical mixtures of commercially available nylon 6 homopolymer and commercially available random N6/N66 copolymers (84/16). Table 3 gives the proportion of each polymer component as well as the proportion of N66 in the overall composition.
  • Example 19 of this invention have a single melting point which is not depressed.
  • Example 3 and Figure 3 show that up to 50% of N6(84) / N66(16) copolymer can be melt blended into N6 homopolymer while retaining a single T m , indicative of a totally homogenous blend. When the amount of copolymer exceeds about 65%, the composition tends to become non- homogeneous. Note that a maximum DT @ 47 °C is observed for this blend system which is much higher than that for either of the two blend constituents, i.e., a case of synergistic interaction between the N6 homopolymer and the N6(84) / N66(16) copolymer (Example 3).
  • the melting temperature of conventional copolymers of nylon 6/nylon 66 are compared to the blends of this invention.
  • N6(21) / N66(79) copolymer when blended into N6, does not offer any advantages in terms of larger DT.
  • Figure 7 shows that N66 homopolymer can similarly be modified by melt blending with a N6(84) / N66(16) copolymer.
  • a blend of 75% N66 homopolymer and 25% N6(84) / N66(16) copolymer appears identical to the N66 homopolymer in terms of melting pattern.
  • Such a miscible blend, containing 21% N6, has a 47 °C higher T m than a conventional random copolymer containing 21% N6 ( Figures 4 & 7 ) and much different from a blend of 79 % N66 and 21% N6 which would be expected to exhibit two Tm's ( Figure 1 ).
  • the copolymer rich in N66 i.e., N6(21) / N66(79) is more effective in enhancing the DT of N66, as opposed to the N6(84) / N66(16) copolymer ( Figure 5 ).
  • N12 can be incorporated in N6 by melt blending N6 homopolymer and a random copolymer of N6(83)/N12(17). The resulting blend is totally homogeneous, characterized by just one T m .
  • Nylon 6 Compositions of Reduced Crystallizability.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Shaping By String And By Release Of Stress In Plastics And The Like (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)

Abstract

L'invention concerne un procédé relatif à l'élaboration de mélanges très uniformes obtenus par voie fondue, d'homopolymères de nylon semi-cristallins et de copolymères de nylon semi-cristallins. Lesdits mélanges ont un point de fusion significatif unique qui remplace les points de fusion individuels propres aux différents constituants de nylon. Selon une variante, l'écart entre la température de fusion du mélange et sa température de cristallisation est supérieur à l'écart entre ces deux températures pour chacun des homopolymères et copolymères constitutifs susmentionnés. Selon une autre variante, le mélange a une température de fusion à peu près équivalente à celle de l'homopolymère de nylon semi-cristallin.
PCT/US1999/004693 1998-03-10 1999-03-04 Melanges miscibles multiconstituants de nylons a proprietes ameliorees Ceased WO1999046334A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BR9908698-0A BR9908698A (pt) 1998-03-10 1999-03-04 Processo para produzir uma composiçãosemi-cristalina de nylon e filme produzido porfundição ou moldagem
JP2000535705A JP2002506109A (ja) 1998-03-10 1999-03-04 改良された特性を有するナイロンの多成分混和性ブレンド
EP99911086A EP1062277A1 (fr) 1998-03-10 1999-03-04 Melanges miscibles multiconstituants de nylons a proprietes ameliorees
AU29813/99A AU2981399A (en) 1998-03-10 1999-03-04 Multi-component miscible blends of nylons with improved properties
KR1020007010034A KR20010041775A (ko) 1998-03-10 1999-03-04 개선된 특성을 갖는 나일론의 다-성분 혼화가능한 혼합물
CA002323204A CA2323204A1 (fr) 1998-03-10 1999-03-04 Melanges miscibles multiconstituants de nylons a proprietes ameliorees

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US3766498A 1998-03-10 1998-03-10
US09/037,664 1998-03-10

Publications (1)

Publication Number Publication Date
WO1999046334A1 true WO1999046334A1 (fr) 1999-09-16

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Family Applications (1)

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PCT/US1999/004693 Ceased WO1999046334A1 (fr) 1998-03-10 1999-03-04 Melanges miscibles multiconstituants de nylons a proprietes ameliorees

Country Status (7)

Country Link
EP (1) EP1062277A1 (fr)
JP (1) JP2002506109A (fr)
KR (1) KR20010041775A (fr)
AU (1) AU2981399A (fr)
BR (1) BR9908698A (fr)
CA (1) CA2323204A1 (fr)
WO (1) WO1999046334A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001014475A1 (fr) * 1999-08-26 2001-03-01 Alliedsignal Inc. Compositions de moulage de nylon a apparence superficielle amelioree
CN109671875A (zh) * 2017-10-16 2019-04-23 昭和电工包装株式会社 蓄电设备用外包装材料及蓄电设备
US20230038477A1 (en) * 2020-01-24 2023-02-09 The Yokohama Rubber Co., Ltd. Resin composition for refrigerant transporting hoses, and refrigerant transporting hose

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL2906612T3 (pl) * 2012-10-10 2024-09-30 Golden Lady Company S.P.A. Przędze i tkaniny odzieżowe z poliamidu oraz wytworzone z nich ubrania

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0170385A1 (fr) * 1984-06-29 1986-02-05 American Can Company Composition à base de nylon, films plastiques en contenant une couche et emballages fabriqués à partir de ceux-ci
US4647483A (en) * 1984-06-29 1987-03-03 American Can Company Nylon copolymer and nylon blends and films made therefrom
US4683170A (en) * 1984-06-29 1987-07-28 American Can Company Nylon copolymer and nylon blends and films made therefrom
US4861838A (en) * 1987-06-22 1989-08-29 Allied-Signal Inc. Process for production of quasi-random copolymers from homopolymers
US4877684A (en) * 1987-08-24 1989-10-31 American National Can Company Nylon carrier for polymer concentrate, and films and packages made with the concentrate
EP0358038A1 (fr) * 1988-08-23 1990-03-14 Viskase Corporation Copolymère de nylon amorphe et films et mélanges de copolyamides
EP0408390A1 (fr) * 1989-07-14 1991-01-16 Du Pont Canada Inc. Film thermoformable de nylon
WO1992015641A2 (fr) * 1991-03-06 1992-09-17 Allied-Signal Inc. Composition de film thermiquement stable et comprenant un polyepsilon-caprolactame
US5359013A (en) * 1990-11-06 1994-10-25 Alliedsignal Inc. Polymer nylon compositions featuring improved rates of crystallization and method for forming the same

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0170385A1 (fr) * 1984-06-29 1986-02-05 American Can Company Composition à base de nylon, films plastiques en contenant une couche et emballages fabriqués à partir de ceux-ci
US4647483A (en) * 1984-06-29 1987-03-03 American Can Company Nylon copolymer and nylon blends and films made therefrom
US4665135A (en) * 1984-06-29 1987-05-12 American Can Company Nylon blends and films made therefrom
US4683170A (en) * 1984-06-29 1987-07-28 American Can Company Nylon copolymer and nylon blends and films made therefrom
US4861838A (en) * 1987-06-22 1989-08-29 Allied-Signal Inc. Process for production of quasi-random copolymers from homopolymers
US4877684A (en) * 1987-08-24 1989-10-31 American National Can Company Nylon carrier for polymer concentrate, and films and packages made with the concentrate
EP0358038A1 (fr) * 1988-08-23 1990-03-14 Viskase Corporation Copolymère de nylon amorphe et films et mélanges de copolyamides
US5053259A (en) * 1988-08-23 1991-10-01 Viskase Corporation Amorphous nylon copolymer and copolyamide films and blends
US5344679A (en) * 1988-08-23 1994-09-06 Viskase Corporation Amorphous nylon copolymer and copolyamide films and blends
EP0408390A1 (fr) * 1989-07-14 1991-01-16 Du Pont Canada Inc. Film thermoformable de nylon
US5359013A (en) * 1990-11-06 1994-10-25 Alliedsignal Inc. Polymer nylon compositions featuring improved rates of crystallization and method for forming the same
WO1992015641A2 (fr) * 1991-03-06 1992-09-17 Allied-Signal Inc. Composition de film thermiquement stable et comprenant un polyepsilon-caprolactame
US5206309A (en) * 1991-03-06 1993-04-27 Allied Signal Inc. Heat stable film composition comprising polyepsiloncaprolactam

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001014475A1 (fr) * 1999-08-26 2001-03-01 Alliedsignal Inc. Compositions de moulage de nylon a apparence superficielle amelioree
US6416704B1 (en) 1999-08-26 2002-07-09 Alliedsignal Inc. Nylon molding compositions having improved surface appearance
CN109671875A (zh) * 2017-10-16 2019-04-23 昭和电工包装株式会社 蓄电设备用外包装材料及蓄电设备
CN109671875B (zh) * 2017-10-16 2023-08-01 株式会社乐索纳克包装 蓄电设备用外包装材料及蓄电设备
US20230038477A1 (en) * 2020-01-24 2023-02-09 The Yokohama Rubber Co., Ltd. Resin composition for refrigerant transporting hoses, and refrigerant transporting hose

Also Published As

Publication number Publication date
CA2323204A1 (fr) 1999-09-16
JP2002506109A (ja) 2002-02-26
AU2981399A (en) 1999-09-27
BR9908698A (pt) 2001-10-30
KR20010041775A (ko) 2001-05-25
EP1062277A1 (fr) 2000-12-27

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