JP6426154B2 - ポリマー粒子の表面架橋方法 - Google Patents
ポリマー粒子の表面架橋方法 Download PDFInfo
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- JP6426154B2 JP6426154B2 JP2016513386A JP2016513386A JP6426154B2 JP 6426154 B2 JP6426154 B2 JP 6426154B2 JP 2016513386 A JP2016513386 A JP 2016513386A JP 2016513386 A JP2016513386 A JP 2016513386A JP 6426154 B2 JP6426154 B2 JP 6426154B2
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- polymer
- powder
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- polyamide
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- 229920000642 polymer Polymers 0.000 title claims description 78
- 239000002245 particle Substances 0.000 title claims description 61
- 238000000034 method Methods 0.000 title claims description 52
- 238000004132 cross linking Methods 0.000 title claims description 38
- 239000000843 powder Substances 0.000 claims description 95
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 30
- 239000004952 Polyamide Substances 0.000 claims description 29
- 229920002647 polyamide Polymers 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 28
- 239000004971 Cross linker Substances 0.000 claims description 25
- 238000006116 polymerization reaction Methods 0.000 claims description 22
- 150000003951 lactams Chemical class 0.000 claims description 19
- 150000004985 diamines Chemical class 0.000 claims description 18
- 239000004962 Polyamide-imide Substances 0.000 claims description 16
- -1 acyl lactams Chemical class 0.000 claims description 16
- 239000003431 cross linking reagent Substances 0.000 claims description 16
- 125000000524 functional group Chemical group 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 16
- 229920002312 polyamide-imide Polymers 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 16
- 229920006037 cross link polymer Polymers 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 12
- 230000008018 melting Effects 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 12
- 239000012429 reaction media Substances 0.000 claims description 12
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 7
- 239000002131 composite material Substances 0.000 claims description 7
- 239000002537 cosmetic Substances 0.000 claims description 7
- 239000005056 polyisocyanate Substances 0.000 claims description 7
- 229920001228 polyisocyanate Polymers 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000006386 neutralization reaction Methods 0.000 claims description 6
- 230000005855 radiation Effects 0.000 claims description 6
- 229920006659 PA12 Polymers 0.000 claims description 5
- 230000003213 activating effect Effects 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 229920000572 Nylon 6/12 Polymers 0.000 claims description 4
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- 239000000758 substrate Substances 0.000 claims description 3
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 2
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- 230000000996 additive effect Effects 0.000 claims description 2
- 238000005054 agglomeration Methods 0.000 claims description 2
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- 229920000768 polyamine Polymers 0.000 claims description 2
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- 238000012546 transfer Methods 0.000 claims description 2
- 150000002918 oxazolines Chemical class 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 10
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- 229910052757 nitrogen Inorganic materials 0.000 description 9
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- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 8
- RKISUIUJZGSLEV-UHFFFAOYSA-N n-[2-(octadecanoylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
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- 230000000052 comparative effect Effects 0.000 description 5
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- 229910000104 sodium hydride Inorganic materials 0.000 description 5
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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- 150000001408 amides Chemical group 0.000 description 4
- 239000011258 core-shell material Substances 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- 229920002292 Nylon 6 Polymers 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
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- 238000005259 measurement Methods 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- HOWGUJZVBDQJKV-UHFFFAOYSA-N n-propyl-nonadecane Natural products CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- ROFWOEQFASWFTK-UHFFFAOYSA-N 1-cyclohexylpropylcyclohexane Chemical compound C1CCCCC1C(CC)C1CCCCC1 ROFWOEQFASWFTK-UHFFFAOYSA-N 0.000 description 2
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920000299 Nylon 12 Polymers 0.000 description 2
- 229920007955 Orgasol® 2002 D NAT 1 Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- QQHJDPROMQRDLA-UHFFFAOYSA-N hexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC(O)=O QQHJDPROMQRDLA-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- BNJOQKFENDDGSC-UHFFFAOYSA-N octadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(O)=O BNJOQKFENDDGSC-UHFFFAOYSA-N 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
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- 238000006068 polycondensation reaction Methods 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 2
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
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- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- IZKZIDXHCDIZKY-UHFFFAOYSA-N heptane-1,1-diamine Chemical compound CCCCCCC(N)N IZKZIDXHCDIZKY-UHFFFAOYSA-N 0.000 description 1
- FBQUUIXMSDZPEB-UHFFFAOYSA-N hexadecane-1,1-diamine Chemical compound CCCCCCCCCCCCCCCC(N)N FBQUUIXMSDZPEB-UHFFFAOYSA-N 0.000 description 1
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 1
- 229920006017 homo-polyamide Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- DDLUSQPEQUJVOY-UHFFFAOYSA-N nonane-1,1-diamine Chemical compound CCCCCCCCC(N)N DDLUSQPEQUJVOY-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 1
- 229940116918 octadecenedioic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- KJOMYNHMBRNCNY-UHFFFAOYSA-N pentane-1,1-diamine Chemical compound CCCCC(N)N KJOMYNHMBRNCNY-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical class ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003140 primary amides Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- FRXCPDXZCDMUGX-UHFFFAOYSA-N tridecane-1,1-diamine Chemical compound CCCCCCCCCCCCC(N)N FRXCPDXZCDMUGX-UHFFFAOYSA-N 0.000 description 1
- XJIAZXYLMDIWLU-UHFFFAOYSA-N undecane-1,1-diamine Chemical compound CCCCCCCCCCC(N)N XJIAZXYLMDIWLU-UHFFFAOYSA-N 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
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- B—PERFORMING OPERATIONS; TRANSPORTING
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Description
本発明は、1つ以上の不安定水素官能基を有する粒子形態のポリマーの表面架橋のための方法に関し、ポリマーの不安定水素官能基と反応できる少なくとも2つの官能基を含む架橋剤を用いる工程を含み、この架橋方法は、ポリマーの融点より低い温度で行われる。
本発明による架橋方法のための原料は、1つ以上の不安定水素官能基を有するポリマーである。
本発明によるポリマーは、粒子の形態であり、これは形状が球体、擬球体または角形であってもよい。一般に、粒子の粒径は、この粒子の製造方法に依存する。
本発明による架橋剤は、ポリマーの不安定水素官能基と反応できる少なくとも2つの官能基を含む。
本発明による1つ以上の不安定水素官能基を有するポリマーの粉末への架橋剤の添加工程は、以下:
(1)架橋剤が液体であるまたは溶媒中にある場合には粒子上に直接架橋剤を含浸させ、次いで反応を開始させるために加熱させるか;
(2)または架橋剤の溶媒中の固体/液体分散液中にポリマー粉末を入れ、ここに架橋反応を開始するための反応温度で架橋剤を添加させるか;
のいずれかの方法で行うことができる。
ポリマーの反応種の生成の先行工程が必要とされる場合がある。反応種、即ち求核性種を生じさせるために、ポリマーから不安定水素を引き抜くのに十分強い塩基を使用できる。
本発明による架橋方法は、「最終」製品としてのポリマー粉末において行うことができる。これはまた重合方法に取り入れることができる。
重合工程、
先行工程において得られた粉末形態のポリマーの上記で定義されるような架橋工程および
反応媒体の中和の任意工程
を含む。
使用される溶媒はモノマーを溶解するが、重合中に生成するポリマー粒子を溶解しない。溶媒の例は特許EP192515に記載されている。有利なことには、溶媒がパラフィン系炭化水素画分であり、この沸点の範囲は、120から170℃であり、有利なことには120と170℃との間、好ましくは140から170℃、有利なことには140と170℃との間である。溶媒は、開始温度、即ち重合が始まる温度においてモノマーで過飽和されてもよい。
触媒は、ラクタムのアニオン性重合のための通常の触媒から選択される。これは、ラクタムの場合には、ラクタムとの反応の後にラクタメートをもたらす程度に十分強い塩基である。幾つかの触媒の組み合わせが想定できる。非限定例としては、水素化ナトリウム、水素化カリウム、ナトリウム、ナトリウムメトキシドおよび/またはナトリウムエトキシドを挙げることができる。導入された触媒の量は、一般にモノマー100モルに対して0.5から3モルの範囲であることができ、有利なことには、モノマー100モルに対して0.5と3モルとの間である。
重合をもたらすおよび/または促進することが役割である活性化剤も添加される。活性化剤は、ラクタム−N−カルボキシアニリド、(モノ)イソシアネート、ポリイソシアネート、カルボジイミド、シアンアミド、アシルラクタムおよびアシルカルバメート、トリアジン、尿素、N−置換イミド、三塩化リンおよびエステルから選択される。これはまた、場合により幾つかの活性化剤の混合物であることもできる。活性化剤はまた、場合により、例えばラクタムとアルキルイソシアネートとを反応させてアシルラクタムを得ることによって、インサイチュで生成することができる。触媒/活性化剤のモル比は、0.2から2の範囲、有利なことには0.2と2との間、好ましくは0.8から1.2、有利なことには0.8と1.2との間である。
アニオン性重合は、連続またはこの他に好ましくはバッチで行われる。バッチで行われる場合には、溶媒が導入され、次いで同時にまたは連続的にモノマー、触媒、活性化剤が導入される。まず溶媒およびモノマーを導入し、次いで例えば共沸蒸留を用いて微量の水を除去し、次いで媒体が無水物になったら触媒を添加することが推奨される。固化が生じるのを防止するためにまたは重合の制御の損失を防止するために、一度ではなく、漸進的またはこの他に所与の導入割合にて活性化剤を導入することが有利な場合がある。重合は、大気圧またはこの他にわずかに大きな圧力(熱溶媒の分圧)下、20℃から溶媒の沸点までの範囲の温度にて、行われる。
本発明による粉末粒子は、上記で記載されるような架橋方法によって得られる。本発明による粒子はまた、上記で記載される架橋方法によって得られることができる。
上記で定義されるような1つ以上の不安定水素官能基を有するポリマーからなる1つ以上の領域および
上記で定義されるような架橋剤で架橋されたポリマーを含む1つ以上の領域
を含む。
上記で定義されるような1つ以上の不安定水素官能基を有するポリマーからなるコアおよび
上記で定義されるような架橋剤で架橋されたポリマーを含むコア上にある層
を含む。
本発明はまた、上記で定義されるような粉末を含む組成物に関する。好ましくは、組成物が熱硬化性組成物である。
本発明は、上記で定義されるような粉末の、複合体、構造接着剤、特に金属、プラスチック、木材、ガラス、紙またはゴム基材に適用できる粉末塗料または液体塗料に基づく基材コーティングおよび転写紙における、特にフィラーまたは補強材としての使用に関する。
平均直径の測定:
例示された粉末の粒子の平均直径は、ISO標準13319に従って測定される。
粉末の分析は、ISO標準11357−3「プラスチック:示差走査熱量分析(DSC)パート3:溶融および結晶化の温度およびエンタルピーの決定」に従って行われる。
溶融エンタルピーは、ポリマーの結晶化度に正比例する。故に2つの製品間の溶融エンタルピーの比較により、これらの結晶化度を比較することができる。
溶解度は、ヘキサフルオロイソプロパノールのリットルあたり1gの粉末を導入することによって測定される。これらの混合物は、非架橋ポリマー鎖を溶解するために24時間周囲温度で維持される。
2800mlの溶媒、次いで連続的に899gのラクタム12、14.4gのEBS(エチレンビスステアルアミド)および73.0gのOrgasol(R)2002 UD NAT1(PA12粉末)を窒素下で維持された反応器中に入れる。300rpmにて撹拌を開始した後、110℃まで徐々に加熱し、次いで存在し得る微量の水を共沸捕捉するために280mlの溶媒を真空下で留去する。
2つのタイプの粉末を比較した:
架橋されていないOrgasol(R)2002 D NAT1と呼ばれる市販の粉末;この粉末は比較粉末Aを構成する。これは、先に記載された方法に従って調製された粉末に対応するが、架橋工程はない、
実施例1による方法を用いて得られる本発明によるBと示される粉末。
屈折率応答係数K(RI)を測定する。K(RI)は、HFIP中のPA12の濃度に正比例する。201の係数が、Orgasol(R)2002 D NAT1に関して測定され、45の係数が、本発明の粉末に関して測定される。
2452mlの溶媒、次いで連続的に919.3gのラクタム6(カプロラクタム)、4.7gのEBS(エチレンビスステアルアミド)および10.5gのAerosyl(R)R972を窒素下で維持された反応器中に入れる。300rpmにて撹拌を開始した後、110℃まで徐々に加熱し、次いで294mlの溶媒を、存在し得る微量の水を共沸捕捉するために真空下で留去する。
2つのタイプの粉末を比較した:
架橋されていないOrgasol(R)1002 D Nat1と呼ばれる市販の粉末;この粉末は比較粉末Cを構成する。これは、先に記載された方法に従って調製された粉末に対応するが、架橋工程はない、
実施例2による方法を用いて得られる本発明によるDと示される粉末。
粉末を90℃にてm−クレゾールに含浸させる。不溶性粒子が生じ、これがポリアミドDの良好な架橋を特徴付ける。比較粉末Cの場合、不溶性材料は生じない。
ポリアミドの合成:
2800mlの溶媒、次いで連続的に919.3gのラクタム12(ラウリルラクタム)、14.7gのEBS(エチレンビスステアルアミド)および1.84gのSipernat(R)320DSを窒素下に維持された反応器に入れる。300rpmにて撹拌を開始した後、110℃まで徐々に加熱し、次いで存在し得る微量の水を共沸捕捉するために280mlの溶媒を真空下で留去する。
ポリアミド−イミド粉末を以下のように得る。撹拌を伴って120℃にて、メチレンビス(シクロヘキシルイソシアネート)の溶液:ラクタム12に対して0.1モル%のH12MDIを、3時間で反応媒体に添加し、次いで得られた混合物を架橋剤のすべての官能基が消費されるようにさらに2時間放置する。比較粉末Eを構成する、90℃でm−クレゾール中に完全に可溶性のポリアミド−イミド粉末を、次いで得る。
得られた粉末を表面架橋する工程を以下のように行う。撹拌しながら120℃にて、ヘキサメチレンジイソシアネートの溶液:ラクタム12に対して4.9モル%のHMDIを、3時間で反応媒体に添加し、次いで得られた混合物をすべての反応性官能基が消費されるようにさらに2時間放置する。
2つのタイプの粉末を比較した:
上記で記載されるポリアミド−イミドの合成から得られる比較粉末E;
実施例3による方法を用いて得られる本発明によるFと示される粉末。
粉末を90℃にてm−クレゾールに含浸させる。不溶性粒子が生じ、これがポリアミド−イミドFの良好な架橋を特徴付ける。
Claims (15)
- 1つ以上の不安定水素官能基を有する粒子形態の、ポリアミド(ただし、該ポリアミドを構成する繰り返しユニットが、ラクタムおよび式:(Caジアミン).(Cb二酸)に対応するユニット(ここで、aはジアミンの炭素原子の数を表し、bは二酸の炭素原子の数を表し、aおよびbそれぞれは4から36の範囲である)から誘導されるユニットから選択される)、ポリアミド−イミド、ポリウレタン、ポリアミンおよびこれらのポリマーのブレンドから選択されるポリマーの表面架橋のための方法であって、ポリマーの不安定水素官能基と反応できる少なくとも2つの官能基を含む架橋剤を用いる工程を含み、前記架橋方法が、ポリマーの融点より低い温度で行われる方法。
- ポリアミドが、PA6、PA11、PA12、PA6/12、PA6.12、PA6.10、PA10.10、PA10.12、PA6.6、PA8、PA4およびPA4.6、ならびにこれらのポリマーのブレンドから選択されることを特徴とする、請求項1に記載の方法。
- ポリアミドが、PA12であることを特徴とする、請求項2に記載の方法。
- ポリマー粒子が、1から200μmの平均直径を有することを特徴とする、請求項1から3のいずれか一項に記載の方法。
- 架橋剤が、以下の官能基:イソシアネート、カルボジイミド、エポキシ、アシルラクタム、オキサゾリンおよびこの異性体、オキサジンおよびこの異性体、ならびにPCl3を保持する化合物から選択されることを特徴とする、請求項1から4のいずれか一項に記載の方法。
- 架橋剤が、ポリイソシアネートであることを特徴とする、請求項5に記載の方法。
- 架橋剤が、1つ以上の不安定水素官能基を有するポリマーを構成するモノマーの総モル数に対して、0.1から15モル%の含有量であることを特徴とする、請求項1から6のいずれか一項に記載の方法。
- ポリマーの重合方法であって、以下の連続工程:
重合工程、
請求項1から7のいずれか一項に記載の、先行工程で得られた粉末形態のポリマーの架橋工程、および
反応媒体の中和の任意工程
を含む方法。 - 重合工程が、触媒の存在下および活性化剤の存在下で、溶媒の溶液中でのアニオン性重合工程であることを特徴とする、請求項8に記載の方法。
- 請求項1から4に記載の1つ以上の不安定水素官能基を有するポリマーからなる1つ以上の領域、および
請求項1および5から7に記載の架橋剤で架橋された前記ポリマーを含む1つ以上の領域
を含む、ポリマー粉末粒子。 - 請求項1から4に記載の1つ以上の不安定水素官能基を有するポリマーからなるコア、および
請求項1および5から7に記載の架橋剤で架橋された前記ポリマーを含む層
を含むことを特徴とする、請求項10に記載の粒子。 - 請求項10または11に記載の粉末の粒子を含む組成物。
- 複合体、構造接着剤、基材コーティングおよび転写紙における、請求項10または11に記載の粉末の粒子の使用。
- レーザービーム、赤外放射線またはUV放射線から選択される放射線によってもたらされる溶融による粉末の凝集によって対象物を製造するための、請求項10または11に記載の粉末粒子の使用。
- 化粧品組成物における添加剤としての、請求項10または11に記載の粉末の粒子の使用。
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WO2019135844A1 (en) | 2017-12-12 | 2019-07-11 | Hexcel Corporation | Semipreg with thermoplastic toughened novolac-based epoxy resin matrix |
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US20160152782A1 (en) | 2016-06-02 |
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EP2997078B1 (fr) | 2019-06-26 |
FR3005660A1 (fr) | 2014-11-21 |
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