CA2055262A1 - Moulding compositions which are stable to alcohols and boiling water - Google Patents
Moulding compositions which are stable to alcohols and boiling waterInfo
- Publication number
- CA2055262A1 CA2055262A1 CA 2055262 CA2055262A CA2055262A1 CA 2055262 A1 CA2055262 A1 CA 2055262A1 CA 2055262 CA2055262 CA 2055262 CA 2055262 A CA2055262 A CA 2055262A CA 2055262 A1 CA2055262 A1 CA 2055262A1
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- CA
- Canada
- Prior art keywords
- mol
- acid
- alcohols
- methane
- boiling water
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 22
- 238000000465 moulding Methods 0.000 title claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 150000001298 alcohols Chemical class 0.000 title claims abstract description 11
- 238000009835 boiling Methods 0.000 title claims abstract description 11
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 24
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims abstract description 9
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 claims abstract description 9
- WMRCTEPOPAZMMN-UHFFFAOYSA-N 2-undecylpropanedioic acid Chemical compound CCCCCCCCCCCC(C(O)=O)C(O)=O WMRCTEPOPAZMMN-UHFFFAOYSA-N 0.000 claims abstract description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 239000012744 reinforcing agent Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 238000006068 polycondensation reaction Methods 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- -1 for example Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 2
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910003953 H3PO2 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920001577 copolymer Chemical class 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- JCUZDQXWVYNXHD-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diamine Chemical compound NCCC(C)CC(C)(C)CN JCUZDQXWVYNXHD-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229920006020 amorphous polyamide Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GQZXNSPRSGFJLY-UHFFFAOYSA-N hydroxyphosphanone Chemical compound OP=O GQZXNSPRSGFJLY-UHFFFAOYSA-N 0.000 description 1
- 229940046817 hypophosphorus acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
ABSTRACT
A moulding composition which comprises an amorphous copolyamide obtained by polycondensation of A. 1. 50 - 99.5 mol-% of isophthalic acid, 2. 0.5 - 50 mol-% of dodecanedi-carboxylic acid, and B. 1. 10 - 50 mol-% of decamethylenediamine, 2. 50 - 90 mol-% of bis(4-aminocyclohexyl)methane. The composition is stable to alcohols and boiling water and is useful for manufacturing the objects for which the stability to alcohols is an essential requirement, such as viewing windows in apparatuses.
A moulding composition which comprises an amorphous copolyamide obtained by polycondensation of A. 1. 50 - 99.5 mol-% of isophthalic acid, 2. 0.5 - 50 mol-% of dodecanedi-carboxylic acid, and B. 1. 10 - 50 mol-% of decamethylenediamine, 2. 50 - 90 mol-% of bis(4-aminocyclohexyl)methane. The composition is stable to alcohols and boiling water and is useful for manufacturing the objects for which the stability to alcohols is an essential requirement, such as viewing windows in apparatuses.
Description
- 1 2~
MOULDING COMPaSITIONS WHICH ARE STABLE
TO ALCOHOLS AND BOILING WATER
The invention relates to moulding compositions which are based on amorphous copolyamides and are stable to alcohols and boiling water.
Moulding compositions which are based on amorphous polyamides and are stable to boiling water are known (European Patents 50 742 and 69 700 and German Patent 3 600 015). However, these moulding compositions have a crucial disadvantage as far as their serviceability is concerned - they are not stable to alcohols, such as, for example, methanol, ethanol, propanols, butanols and the like. As the case may be, they tend to become turbid, to swell or to become tacky in the presence of alcohols;
in some cases, they are completely soluble in alcohol. However, for many applications, such as, for example, for spectacle frames or viewing windows in apparatuses, stability to alcohols is an essential prerequisite.
The object of the invention was to provide moulding compositions which do not have the above-mentioned disadvantages, but without losing their other advantageous properties.
This object may be achieved by means of compositions using the copolyamides according to the invention.
Thus, according to one aspect, the invention provides a moulding composition which is stable to alcohols and boiling water, which comprises an amorphous copolyamide obtained by polycondensing A. 1. 50 - 99.5 mol-% of isophthalic acid 2. 0.5 - 50 mol-% of dodecanedicarboxylic acid with B. 1. 10 - 50 mol-% of decamethylenediamine 2. 50 - 90 mol-% of bis(4-aminocyclohexyl)methane.
According to another aspect, the invention provides an amorphous copolyamide obtained by polycondensing A. l. 50 - 99.5 mol-% oE isophthalic acid 2. 0.5 - 50 mol-% of dodecanedicarboxylic acid with B. 1. 10 - 50 mol-% of decamethylenediamine 2. 50 - 90 mol-% of bis(4-aminocyclohexyl)methane.
Preference is given to moulding compositions based on copolyamides obtained by polycondensing A. 1. 50 - 99.5 mol-% of isophthalic acid 2. 0.5 50 mol-% of dodecanedicarboxylic acid with B. 1. 20 - 50 mol-% of decamethylenediamine 2. 50 - 30 mol-% of bis(4-aminocyclohexyl)methane.
A further preferred embodiment uses copolyamides in which up to 50 mol-% of the isophthalic acid has been replaced by terephthalic acid. It is furthermore possible to replace some or all of the bis(4-aminocyclohexyl)methane by its methyl derivative, bis(3-methyl-4-aminocyclohexyl)methane.
Decamethylenediamine is ta]~en to mean any aliphatic diamine having the empirical formula CloH24N2 whose amino groups are separated by at least 7 to 10 CH2 units. Diamines may be employed individually or as a mixture.
The copolyamides on which the moulding compositions according to the invention are based have a relative solution viscosity (nrel) in the range from 1.4 to 2.1, preferably in the range from 1.50 to 1.95. The glass transition point (T ) of the . ;~
2 ~
- 2a -copolyamides is in the range from 120 to 180C, preferably in the range from 140 to 170C.
The preparation of the copolyamides is known in principle. The polycondensation of the components is carried out in the melt. The preparation may optionally be carried out in the presence of a phosphorus-derived acid of the general formula H3POn where n = 2 to 4 or triphenyl phosphite.
Suitable phosphorus-derived acids are hypophosphorus acid, phosphorus acid and phosphoric acid.
MOULDING COMPaSITIONS WHICH ARE STABLE
TO ALCOHOLS AND BOILING WATER
The invention relates to moulding compositions which are based on amorphous copolyamides and are stable to alcohols and boiling water.
Moulding compositions which are based on amorphous polyamides and are stable to boiling water are known (European Patents 50 742 and 69 700 and German Patent 3 600 015). However, these moulding compositions have a crucial disadvantage as far as their serviceability is concerned - they are not stable to alcohols, such as, for example, methanol, ethanol, propanols, butanols and the like. As the case may be, they tend to become turbid, to swell or to become tacky in the presence of alcohols;
in some cases, they are completely soluble in alcohol. However, for many applications, such as, for example, for spectacle frames or viewing windows in apparatuses, stability to alcohols is an essential prerequisite.
The object of the invention was to provide moulding compositions which do not have the above-mentioned disadvantages, but without losing their other advantageous properties.
This object may be achieved by means of compositions using the copolyamides according to the invention.
Thus, according to one aspect, the invention provides a moulding composition which is stable to alcohols and boiling water, which comprises an amorphous copolyamide obtained by polycondensing A. 1. 50 - 99.5 mol-% of isophthalic acid 2. 0.5 - 50 mol-% of dodecanedicarboxylic acid with B. 1. 10 - 50 mol-% of decamethylenediamine 2. 50 - 90 mol-% of bis(4-aminocyclohexyl)methane.
According to another aspect, the invention provides an amorphous copolyamide obtained by polycondensing A. l. 50 - 99.5 mol-% oE isophthalic acid 2. 0.5 - 50 mol-% of dodecanedicarboxylic acid with B. 1. 10 - 50 mol-% of decamethylenediamine 2. 50 - 90 mol-% of bis(4-aminocyclohexyl)methane.
Preference is given to moulding compositions based on copolyamides obtained by polycondensing A. 1. 50 - 99.5 mol-% of isophthalic acid 2. 0.5 50 mol-% of dodecanedicarboxylic acid with B. 1. 20 - 50 mol-% of decamethylenediamine 2. 50 - 30 mol-% of bis(4-aminocyclohexyl)methane.
A further preferred embodiment uses copolyamides in which up to 50 mol-% of the isophthalic acid has been replaced by terephthalic acid. It is furthermore possible to replace some or all of the bis(4-aminocyclohexyl)methane by its methyl derivative, bis(3-methyl-4-aminocyclohexyl)methane.
Decamethylenediamine is ta]~en to mean any aliphatic diamine having the empirical formula CloH24N2 whose amino groups are separated by at least 7 to 10 CH2 units. Diamines may be employed individually or as a mixture.
The copolyamides on which the moulding compositions according to the invention are based have a relative solution viscosity (nrel) in the range from 1.4 to 2.1, preferably in the range from 1.50 to 1.95. The glass transition point (T ) of the . ;~
2 ~
- 2a -copolyamides is in the range from 120 to 180C, preferably in the range from 140 to 170C.
The preparation of the copolyamides is known in principle. The polycondensation of the components is carried out in the melt. The preparation may optionally be carried out in the presence of a phosphorus-derived acid of the general formula H3POn where n = 2 to 4 or triphenyl phosphite.
Suitable phosphorus-derived acids are hypophosphorus acid, phosphorus acid and phosphoric acid.
- 3 - O.Z. 4539 If a catalyst is added, it is employed in an amount of from 0.001 to 1 mol-%, preferably from 0.001 to 0.1 mol-~, based on the sum of all the monomers.
The reaction is carried out in the melt at a temperature in the range from 200 to 350C, preferably from 210 to 320C.
The reaction is u~ually carried out under an inert gas at atmospheric pressure, but may also be carried out under superatmospheric pre sure or reduced pressure.
In order to increase the molecular weight, the copoly-amides may be subjected ~o solid-phase postcondensation in an inert-gas atmosphere.
The copolyamides are converted into moulding compositions in conventional machines by injection moulding or extrusion.
The moulding compositions may additionally contain fillers, such as talc, or reinforcing agents, such as glass fibres, ARAMIDR ~ibres or carbon fibres, and other conventional additives, such as, for example, pigments or stabilisers.
The moulding compositions are converted into mouldings, fibres, films, etc., by conventional processes, such as injection moulding, extrusion or the like.
The moulding compositions according to the invention have surprisingly high stability to alcohols without Lmpair-ment of their good general properties, in particular the stability to boiling water.
The parameters mentioned in the description and the examples were determined using the methods ~elow.
The relative solution viscosity (~r~l) was determined on 2 ~ 6 2 - 4 - O.Z. 453g 0.5 % strength by weight polyamide solutions in m-cresol at 25C.
The glass transition temperature (T8) results from DSC
measurements at a heating xate of 20 K/min.
Examples ~m~
Starting materials: 4.984 kg of isophthalic (30 mol) acid 4.606 kg of dodecane- 120 mol) dicarboxylic acid 2.5~5 kg of n-decamethylene- (15 mol) l,lO-diamine 7.362 kg of bis(4 amino- (35 mol) cyclohexyl)methane 17.000 kg of water 0.340 g of H3PO2 (as a 50 ~ strength by weight aqueous solution) The starting materials were dissolved in water under nitrogen in a polycondensation reactor at 170C and at a pressure of 9 bar. The temperature of the reaction mixture was raised to 230C while maintaining the pressure,and then stirred at this temperature for 1 hour.
The temperature was subsequently raised to 300C. The water liberated was remo~ed by distillation. After 4 hours at 300C, the copolyamide was discharged from the reactor.
~7rel = 1 . 65 T8 = 149 C
Example 2 St~rting materials: 2.492 kg of isophthalic ~15 mol~
acid -;- 2 ~
The reaction is carried out in the melt at a temperature in the range from 200 to 350C, preferably from 210 to 320C.
The reaction is u~ually carried out under an inert gas at atmospheric pressure, but may also be carried out under superatmospheric pre sure or reduced pressure.
In order to increase the molecular weight, the copoly-amides may be subjected ~o solid-phase postcondensation in an inert-gas atmosphere.
The copolyamides are converted into moulding compositions in conventional machines by injection moulding or extrusion.
The moulding compositions may additionally contain fillers, such as talc, or reinforcing agents, such as glass fibres, ARAMIDR ~ibres or carbon fibres, and other conventional additives, such as, for example, pigments or stabilisers.
The moulding compositions are converted into mouldings, fibres, films, etc., by conventional processes, such as injection moulding, extrusion or the like.
The moulding compositions according to the invention have surprisingly high stability to alcohols without Lmpair-ment of their good general properties, in particular the stability to boiling water.
The parameters mentioned in the description and the examples were determined using the methods ~elow.
The relative solution viscosity (~r~l) was determined on 2 ~ 6 2 - 4 - O.Z. 453g 0.5 % strength by weight polyamide solutions in m-cresol at 25C.
The glass transition temperature (T8) results from DSC
measurements at a heating xate of 20 K/min.
Examples ~m~
Starting materials: 4.984 kg of isophthalic (30 mol) acid 4.606 kg of dodecane- 120 mol) dicarboxylic acid 2.5~5 kg of n-decamethylene- (15 mol) l,lO-diamine 7.362 kg of bis(4 amino- (35 mol) cyclohexyl)methane 17.000 kg of water 0.340 g of H3PO2 (as a 50 ~ strength by weight aqueous solution) The starting materials were dissolved in water under nitrogen in a polycondensation reactor at 170C and at a pressure of 9 bar. The temperature of the reaction mixture was raised to 230C while maintaining the pressure,and then stirred at this temperature for 1 hour.
The temperature was subsequently raised to 300C. The water liberated was remo~ed by distillation. After 4 hours at 300C, the copolyamide was discharged from the reactor.
~7rel = 1 . 65 T8 = 149 C
Example 2 St~rting materials: 2.492 kg of isophthalic ~15 mol~
acid -;- 2 ~
- 5 - O.Z. 4539 2.492 kg of terephthalic (15 mol3 acid 4.606 kg of dodecane (20 mol) dicarboxylic acid 2.585 kg of n-decamethylene- (15 mol) l,10-diamine 7.362 kg of bi~(4-amino- (35 mol) cyclohexyl)methane 17.000 kg of water 0.340 g of H2PO2 (as a 50 % strength by weight aqueous solution) The polycondensation was carried out analogou~ly to Example 1.
~rel = 1 54 Tg = 153~C
Example 3 Starting materials: 4.984 kg of isophthalic (30 mol) acid 4.606 kg of dodecane- (20 mol) dicarboxylic acid :: 20 2.585 kg of n-decamethylene- (15 mol) 1,10-diamine : 8.342 kg of bis(3-methyl- (35 mol) 4-aminocyclohexyl)methane 18.000 kg of water 0.300 g of H3PO2 (as a 50 % strength by weight aqueous solution) The polycondensation was carried out analogously to Ex~mple 1.
~ral = 1.50 Tg = 163C
Example 4 The copolyamides prepared a~ per Examples 1 to 3 were , . , -: :. , ~. - ~ - , . .
. . .
,, - ~ .
- ., " , ~
' 2 0 ~ ~ ~ 6 ~
~rel = 1 54 Tg = 153~C
Example 3 Starting materials: 4.984 kg of isophthalic (30 mol) acid 4.606 kg of dodecane- (20 mol) dicarboxylic acid :: 20 2.585 kg of n-decamethylene- (15 mol) 1,10-diamine : 8.342 kg of bis(3-methyl- (35 mol) 4-aminocyclohexyl)methane 18.000 kg of water 0.300 g of H3PO2 (as a 50 % strength by weight aqueous solution) The polycondensation was carried out analogously to Ex~mple 1.
~ral = 1.50 Tg = 163C
Example 4 The copolyamides prepared a~ per Examples 1 to 3 were , . , -: :. , ~. - ~ - , . .
. . .
,, - ~ .
- ., " , ~
' 2 0 ~ ~ ~ 6 ~
- 6 - O.Z. 4539 compared with two commercially available copolyamides (A) and (B) said to be stable to boiling water.
Copolyamide (A) (TROGAMIDB T) contains as monomers terephthalic and trimethylhexamethylenediamine (isomer mixture comprising approximately equal parts by weight of 2,4,4- and 2,2,4-trimethylhexamethylenediamine).
Copolyamide (B) (GRILLAMIDR T~ 55) comprises about 30 mol-% of isophthalic acid, about 30 mol-% of 3,3'-dimethyl-4,4'-diaminodicyclohexylmethane and about 40 mol-% of laurolactam as monomers.
The copolyamides according to the invention and the comparison products were stored in ethanol for 3 weeks at room temperature. While tha copolyamides according to the invention were unchanged in appearance and solution viscosity, the comparison products became tacky after only a few hours. The boiling water test (24 hours in boiling water) likewise caused no change in the copoly-amides according to the invention, while copolyamide (A) became very turbid and copolyamide (B) slightly turbid.
Copolyamide (A) (TROGAMIDB T) contains as monomers terephthalic and trimethylhexamethylenediamine (isomer mixture comprising approximately equal parts by weight of 2,4,4- and 2,2,4-trimethylhexamethylenediamine).
Copolyamide (B) (GRILLAMIDR T~ 55) comprises about 30 mol-% of isophthalic acid, about 30 mol-% of 3,3'-dimethyl-4,4'-diaminodicyclohexylmethane and about 40 mol-% of laurolactam as monomers.
The copolyamides according to the invention and the comparison products were stored in ethanol for 3 weeks at room temperature. While tha copolyamides according to the invention were unchanged in appearance and solution viscosity, the comparison products became tacky after only a few hours. The boiling water test (24 hours in boiling water) likewise caused no change in the copoly-amides according to the invention, while copolyamide (A) became very turbid and copolyamide (B) slightly turbid.
Claims (8)
1. A moulding composition which is stable to alcohols and boiling water, which comprises an amorphous copolyamide obtained by polycondensing A. 1. 50 - 99.5 mol-% of isophthalic acid
2. 0.5 - 50 mol-% of dodecanedicarboxylic acid with B. 1. 10 - 50 mol-% of decamethylenediamine 2. 50 - 90 mol-% of bis(4-aminocyclohexyl)methane.
2. A moulding composition according to claim 1, wherein the copolyamide has been obtained by polycondensing A. 1. 50 - 99.5 mol-% of isophthalic acid 2. 0.5 - 50 mol-% of dodecanedicarboxylic acid with B. 1. 20 - 50 mol-% of decamethylenediamine 2. 50 - 80 mol-% of bis(4-aminocyclohexyl)methane.
2. A moulding composition according to claim 1, wherein the copolyamide has been obtained by polycondensing A. 1. 50 - 99.5 mol-% of isophthalic acid 2. 0.5 - 50 mol-% of dodecanedicarboxylic acid with B. 1. 20 - 50 mol-% of decamethylenediamine 2. 50 - 80 mol-% of bis(4-aminocyclohexyl)methane.
3. A moulding composition according to claim 1 or 2, wherein up to 50 mol-% of the isophthalic acid has been replaced by terephthalic acid.
4. A moulding composition according to claim 1 or 2, comprising further conventional additives.
5. A moulding composition according to claim 4, wherein the additives are selected from the group consisting of fillers, reinforcing agents, pigments and stabilizers.
6. An amorphous copolyamide obtained by polycondensing A. 1. 50 - 99.5 mol-% of isophthalic acid 2. 0.5 - 50 mol-% of dodecanedicarboxylic acid with B. 1. 10 - 50 mol-% of decamethylenediamine 2. 50 - 90 mol-% of bis(4-aminocyclohexyl)methane.
7. An amorphous copolyamide according to claim 1 and obtained by polycondensing A. 1. 50 - 99.5 mol-% of isophthalic acid 2. 0.5 - 50 mol-% of dodecanedicarboxylic acid with B. 1. 20 - 50 mol-% of decamethylenediamine 2. 50 - 80 mol-% of bis(4-aminocyclohexyl)methane.
8. An amorphous copolyamide according to claim 6 or 7, wherein up to 50 mol-% of the isophthalic acid has been replaced by terephthalic acid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19904036246 DE4036246A1 (en) | 1990-11-14 | 1990-11-14 | COMPARISON-RESISTANT SHAPES TO ALCOHOLS AND BOILING WATER |
| DEP4036246.9 | 1990-11-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2055262A1 true CA2055262A1 (en) | 1992-05-15 |
Family
ID=6418242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2055262 Abandoned CA2055262A1 (en) | 1990-11-14 | 1991-11-12 | Moulding compositions which are stable to alcohols and boiling water |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0485711A3 (en) |
| JP (1) | JPH04268330A (en) |
| CA (1) | CA2055262A1 (en) |
| DE (1) | DE4036246A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5360891A (en) * | 1993-04-03 | 1994-11-01 | Huels Aktiengesellschaft | Colorless and transparent, amorphously processable polyamide molding composition having good resistance to stress cracking and good impact strength |
| US10287395B2 (en) | 2013-11-29 | 2019-05-14 | Lotte Advanced Materials Co., Ltd. | Polyamide resin and method for manufacturing same |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1826229A1 (en) * | 2006-02-27 | 2007-08-29 | Arkema France | Amorphous copolyamides comprising p-bis(aminocyclohexyl)methane and terephtalic acid |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3040155A1 (en) * | 1980-10-24 | 1982-06-03 | Dynamit Nobel Ag, 5210 Troisdorf | TRANSPARENT CLEANING WATER AND STERILIZATION RESISTANT POLYAMID |
| CH667462A5 (en) * | 1985-01-07 | 1988-10-14 | Inventa Ag | TRANSPARENT COPOLYAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR THE PRODUCTION OF MOLDED BODIES. |
-
1990
- 1990-11-14 DE DE19904036246 patent/DE4036246A1/en not_active Withdrawn
-
1991
- 1991-09-14 EP EP19910115639 patent/EP0485711A3/en not_active Withdrawn
- 1991-11-12 CA CA 2055262 patent/CA2055262A1/en not_active Abandoned
- 1991-11-12 JP JP29545191A patent/JPH04268330A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5360891A (en) * | 1993-04-03 | 1994-11-01 | Huels Aktiengesellschaft | Colorless and transparent, amorphously processable polyamide molding composition having good resistance to stress cracking and good impact strength |
| US10287395B2 (en) | 2013-11-29 | 2019-05-14 | Lotte Advanced Materials Co., Ltd. | Polyamide resin and method for manufacturing same |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0485711A3 (en) | 1992-11-19 |
| DE4036246A1 (en) | 1992-05-21 |
| JPH04268330A (en) | 1992-09-24 |
| EP0485711A2 (en) | 1992-05-20 |
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| Date | Code | Title | Description |
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