US20030088076A1 - Colored thermoplastic resin compositions for laser welding, specific neutral anthraquinone dyes as colorants therefor, and molded product therefrom - Google Patents
Colored thermoplastic resin compositions for laser welding, specific neutral anthraquinone dyes as colorants therefor, and molded product therefrom Download PDFInfo
- Publication number
- US20030088076A1 US20030088076A1 US10/047,686 US4768601A US2003088076A1 US 20030088076 A1 US20030088076 A1 US 20030088076A1 US 4768601 A US4768601 A US 4768601A US 2003088076 A1 US2003088076 A1 US 2003088076A1
- Authority
- US
- United States
- Prior art keywords
- formula
- dye
- alkyl
- aryl
- alkoxy
- 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
- 238000003466 welding Methods 0.000 title claims abstract description 33
- 230000007935 neutral effect Effects 0.000 title claims abstract description 24
- 229920005992 thermoplastic resin Polymers 0.000 title claims abstract description 23
- 239000011342 resin composition Substances 0.000 title claims abstract description 15
- 239000001000 anthraquinone dye Substances 0.000 title claims description 30
- 239000003086 colorant Substances 0.000 title claims description 26
- 239000000203 mixture Substances 0.000 claims abstract description 40
- 239000001044 red dye Substances 0.000 claims abstract description 32
- 239000000975 dye Substances 0.000 claims description 55
- -1 acylamide Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 19
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims description 15
- 229920000728 polyester Polymers 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 239000012744 reinforcing agent Substances 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims 1
- 229920002647 polyamide Polymers 0.000 claims 1
- 239000001045 blue dye Substances 0.000 abstract description 16
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 abstract description 9
- 238000012360 testing method Methods 0.000 description 68
- 230000000052 comparative effect Effects 0.000 description 31
- 239000001043 yellow dye Substances 0.000 description 29
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 25
- 150000004056 anthraquinones Chemical class 0.000 description 25
- 238000001746 injection moulding Methods 0.000 description 25
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 25
- 229910006074 SO2NH2 Inorganic materials 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 125000000565 sulfonamide group Chemical group 0.000 description 18
- 0 CC.[55*]C1=CC=CC=C1NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O.[56*]C.[57*]C.[58*]C1=CC=CC=C1NCC.[60*]C Chemical compound CC.[55*]C1=CC=CC=C1NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O.[56*]C.[57*]C.[58*]C1=CC=CC=C1NCC.[60*]C 0.000 description 14
- 229920002292 Nylon 6 Polymers 0.000 description 13
- 229910001220 stainless steel Inorganic materials 0.000 description 13
- 239000010935 stainless steel Substances 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 8
- 239000001046 green dye Substances 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- 239000004677 Nylon Substances 0.000 description 6
- 239000006229 carbon black Substances 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- 229920001778 nylon Polymers 0.000 description 6
- XBNVWXKPFORCRI-UHFFFAOYSA-N 2h-naphtho[2,3-f]quinolin-1-one Chemical compound C1=CC=CC2=CC3=C4C(=O)CC=NC4=CC=C3C=C21 XBNVWXKPFORCRI-UHFFFAOYSA-N 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 229920006102 Zytel® Polymers 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920006122 polyamide resin Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229920002302 Nylon 6,6 Polymers 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 239000011152 fibreglass Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- FBNCDTLHQPLASV-UHFFFAOYSA-L disodium;5-methyl-2-[[5-(4-methyl-2-sulfonatoanilino)-9,10-dioxoanthracen-1-yl]amino]benzenesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1NC1=CC=CC2=C1C(=O)C1=CC=CC(NC=3C(=CC(C)=CC=3)S([O-])(=O)=O)=C1C2=O FBNCDTLHQPLASV-UHFFFAOYSA-L 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000005562 fading Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000001048 orange dye Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- OJDDBKYNFZEABF-YJOCEBFMSA-N *.C/N=C(/C)N(C)C(C)=O.P Chemical compound *.C/N=C(/C)N(C)C(C)=O.P OJDDBKYNFZEABF-YJOCEBFMSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- ZLCUIOWQYBYEBG-UHFFFAOYSA-N 1-Amino-2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=C(N)C(C)=CC=C3C(=O)C2=C1 ZLCUIOWQYBYEBG-UHFFFAOYSA-N 0.000 description 1
- ZDVRPQIPVMARSE-UHFFFAOYSA-N 11-aminododecanoic acid Chemical compound CC(N)CCCCCCCCCC(O)=O ZDVRPQIPVMARSE-UHFFFAOYSA-N 0.000 description 1
- XFYQEBBUVNLYBR-UHFFFAOYSA-N 12-phthaloperinone Chemical compound C1=CC(N2C(=O)C=3C(=CC=CC=3)C2=N2)=C3C2=CC=CC3=C1 XFYQEBBUVNLYBR-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- UBZVRROHBDDCQY-UHFFFAOYSA-N 20749-68-2 Chemical compound C1=CC(N2C(=O)C3=C(C(=C(Cl)C(Cl)=C3C2=N2)Cl)Cl)=C3C2=CC=CC3=C1 UBZVRROHBDDCQY-UHFFFAOYSA-N 0.000 description 1
- MMINFSMURORWKH-UHFFFAOYSA-N 3,6-dioxabicyclo[6.2.2]dodeca-1(10),8,11-triene-2,7-dione Chemical compound O=C1OCCOC(=O)C2=CC=C1C=C2 MMINFSMURORWKH-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
- VJUKWPOWHJITTP-UHFFFAOYSA-N 81-39-0 Chemical compound C1=CC(C)=CC=C1NC1=CC=C2C3=C1C(=O)C1=CC=CC=C1C3=CC(=O)N2C VJUKWPOWHJITTP-UHFFFAOYSA-N 0.000 description 1
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
- 239000004953 Aliphatic polyamide Substances 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 101001053401 Arabidopsis thaliana Acid beta-fructofuranosidase 3, vacuolar Proteins 0.000 description 1
- 101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- NFPVFWVECIUZQD-ALCCZGGFSA-N C/N=C(/C)N(C)C(C)=O Chemical compound C/N=C(/C)N(C)C(C)=O NFPVFWVECIUZQD-ALCCZGGFSA-N 0.000 description 1
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- 239000004609 Impact Modifier Substances 0.000 description 1
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 229920003231 aliphatic polyamide Polymers 0.000 description 1
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- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- TZYHIGCKINZLPD-UHFFFAOYSA-N azepan-2-one;hexane-1,6-diamine;hexanedioic acid Chemical compound NCCCCCCN.O=C1CCCCCN1.OC(=O)CCCCC(O)=O TZYHIGCKINZLPD-UHFFFAOYSA-N 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
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Classifications
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Definitions
- the instant invention relates to thermoplastic resin compositions with specific anthraquinone dyes. More particularly, the inventions relates to such compositions having improved laser weldability.
- laser welding is widely known for its simple operation, labor savings, improvement of productivity, clear joints, and reduction of production cost. It is useful in various applications including the preparation of molded articles, including hollow shapes, in automobile industries and electric and electronic industries.
- work has intensified in the area of blends of thermoplastic resin and a colorant containing an organic dye or pigment. Better control of the conversion of laser energy to heat is achieved by the addition of such colorants to the resins.
- Laser beams penetrate through transparent articles positioned closer to the laser beam source, and are largely absorbed in the opaque article, which has a relatively higher absorption coefficient in comparison with the aforementioned transparent article. Careful attention to the amount of the colorants therein results in the junction portion being melted and the articles joined together.
- thermoplastic components may be black (carbon black or nigrosine), which is commonly and widely used in the automobile industries and other applications.
- carbon black and nigrosine can not transmit a laser beam with a main wavelength in infra-red region (1200 nm to 800 nm), such as Nd:YAG laser and a diode laser which are of wide use in industries.
- thermoplastic resin compositions both black in appearance can be used for laser-welded molded articles, and both for the transparent and opaque parts subjected to the laser beam.
- a significantly improved transmission to near-infrared light of the laser beam, with excellent and balanced heat-resistance and mechanical properties as required in automobile applications is achieved by including a specific weight percentage of black dyes.
- the object of the present invention is to offer a thermoplastic resin composition capable of offering moldings which appear in black, offer excellent thermal resistance, and are transparent to a laser beam, in particular to the near-infrared light region.
- a further object of the invention is to provide select anthraquinone blue dyes which offer minimal discoloration during molding and in high temperature applications.
- a feature of the invention is the compositions herein can provide a substantially homogenous visual black impression of transparent and opaque articles that appears in black and absorbs the laser beam largely by containing black dyes, welded together by the laser beam, and possess excellent and balanced heat-resistance and mechanical properties as required in automotive parts, electric/electronic components, mechanical components, and many other applications.
- thermoplastic resin compositions for laser welding comprised of thermoplastic resin and a black colorant comprising at least neutral anthraquinone dye which imparts color of blue, absorbs visible light with wave length less than 700 nm and transmits a laser beam with wavelength at 800 nm to 1200 nm.
- neutral anthraquinone dye which imparts color of blue, absorbs visible light with wave length less than 700 nm and transmits a laser beam with wavelength at 800 nm to 1200 nm.
- other red dye which transmit the laser beam with wavelength at 800 nm to 1200 nm in infra-red region such as perinone dyes or monoazo complex dyes can be present at predetermined weight ratio.
- thermoplastic resin composition for laser welding comprising:
- thermoplastic resin [0011] 1) thermoplastic resin
- R 55 and R 58 are independently selected from alkyl groups having 1 to 18 carbon atoms
- R56 and R 59 are independently selected from the group consisting of alkyl, aryl, alkenyl, alkoxy, amino, N-alkylamide, N-arylamide, acyl, acylamide, alkoxycarbonyl, hydroxy, and carboxy groups and halogen atom
- R 57 and R 60 are independently selected from the group consisting of H, alkyl, aryl, alkenyl, alkoxy, amino, N-alkylamide, N-arylamide, acyl, acylamide, carboxy, alkoxycarbonyl, and hydroxy groups and halogen atom
- R 61 , R 62 , R 63 , and R 64 which may be the same or different, are independently selected from the group consisting of H, alkyl, alkenyl, aryl, alkoxy, amino, N-alkylamide, N-arylaminde, acyl, acylamide, carboxy, alkoxycarbonyl, hydroxy group, halogen atom, formula [II-a], and P 1 is NR or CO, wherein R 66 is H, alkyl, or aryl groups.
- R 65 is H, alkyl, aryl, alkoxy, amino, hydroxy, or halogen atom.
- thermoplastic resin compositions for laser welding offer improvements in moldability, solubility in the thermoplastic resin, bleeding and blooming-resistance, transparency to wavelengths of a laser beam at 800 nm to 1200 nm and resistance to chemicals.
- Another advantage is that the composition provides the greater color value to produce the black colorant because of the said neutral anthraquinone dye of formula [I] or [II] as a major component of said colorant and higher heat resistance. Therefore, the compositions of the present invention comprising the black colorant comprising at least said neutral anthraquinone dye as the major component are extremely suitable for thermoplastic resins which requiring melt temperature higher than 300° C. during molding operation.
- compositions of the invention may also contain other yellow dyes in addition to the mixture of anthraquinone dyes with red dyes as one of components of black dyes used as a colorant of the composition, preferably anthraquinone yellow dyes.
- FIG. 1 is a view of the articles in contact with and with a laser beam applied thereto;
- FIG. 2 is identical to FIG. 1, but with the articles of the same color.
- FIG. 3 illustrates a shape and dimensions of a test piece creating a notch in the test piece (60 mm ⁇ 18 mm).
- FIG. 4 is a perspective view of test pieces of FIG. 3 disposed close to each other for a laser welding test and relationship between the test pieces and laser beam.
- FIG. 5 illustrates a shape and dimensions of a test piece creating a notch in the test piece (80 mm ⁇ 40 mm).
- FIG. 6 is a perspective view of test pieces of FIG. 5 disposed close to each other for a laser welding test and relationship between the test pieces and laser beam
- the perinone dyes which are mixed with the above-mentioned anthraquinone dyes for use as a black colorant comprised in the composition of the invention are known products of formula [III].
- the perinone dyes which are mixed with the anthraquinone to produce a black dye may be used alone or in combination thereof.
- Preferred perinone dyes used in the composition of the invention when solubility and / or dispersion in the resin are considered, are those of formula [IV],
- R 14 to R 29 which may be the same or different, are independently an atom or a group selected from the group consisting of H, halogen atom such as Cl, Br, alkyl group having 1 to 18 carbon atoms, alkoxy group having 1 to 18 carbon atoms, aralkyl group, aryl group; m 6 is the number of 1 or 2.
- Dyes which belong to the class of perinone dyes listed in color index are for example C.I.Solvent Orange 60, 78, C.I.Solvent Red 135, 162, 178, 179, C.I.Violet 29, C.I.Pigment Orange 43, C.I.Pigment Red 149. If solubility and dispersibility in the resin are enhanced, solvent type dyes are preferred.
- the monoazo complex dyes which are mixed with the anthraquinone dyes of formula [I] or formula [II] to produce a black dye for use as colorant comprised in the composition of the invention can be represented by formula [V].
- R 30 and R 31 which may be the same or different, are Cl, SO 2 R 32 , SO 2 (-R 33 )(-R 34 ), or H; wherein R 33 and R 34 , which may be the same or different, are independently hydrogen K 2 (D) + atom, linear or branched C1- C4 alkyl; R 32 is linear or branched C1- C4 alkyl; L 3 and L 4 are independently O or COO; (D) + is hydrogen ion, cation of alkali metals, ammonium ion, cations of organic amine including aliphatic primary, secondary and tertiary amines, or quaternary ammonium ion; K 2 is an integer; m 2 is 0, 1 or 2; , M 2 is selected from metals of ionic valency from 2 to 4 (such as Zn, Sr, Cr, Al, Ti, Fe, Zr, Ni, Mn, B[boron] and
- R 35 and R 37 which may be the same of different, are Cl, SO 2 R 32 , SO 2 (-R 33 )(-R 34 ), or H;
- R 33 and R 34 which may be the same or different, are independently hydrogen atom, linear or branched C1- C4 alkyl;
- R 36 and R 38 which may be the same or different, are independently hydrogen atom, linear or branched C1- C18 alkyl, carboxyl, hydroxyl, C1- C18 alkoxy, amino or halogen atoms.
- Suitable cations for use in the above-mentioned monoazo complex dyes are H + ; cations of alkali metal, ammonium ion, cations of organic amine including aliphatic primary, secondary and tertiary amines, quaternary ammonium ion.
- Suitable amines for use in producing the above-mentioned monoazo complex dyes and common in dyestuffs include aliphatic amine, alicyclic amine, alkoxyalkyl amine, amine having alkanol, diamine, amine of guanidine derivatives, and aromatic amine.
- anthrapyridone dyes which are mixed with the anthraquinone dyes of formula [I] or formula [II] to produce a black dye for use as colorants of the invention, can be represented by formula [VI],
- R 67 to R 71 which may be the same or different, are independently selected from the group consisting of H, alkyl, aryl, alkenyl, alkoxy, amino, hydroxy, halogen atom, acyl, acyloxy, acylamide, acyl-N-alkylamide, carboxyl, alkoxycarbonyl, cyclohexylamide, sulfonyl, or formula [VI-a]; and at least one of R 67 to R 74 is of sulfonyl; wherein P 3 is C—R 72 or N; R 72 is H, alkyl, aryl, alkoxy, benzoyl, or benzyl; wherein (G) s+ represents ammonium ion or a cation derived from organic amine compounds or a basic dye; wherein s is 1 or 2, m 5 is an integer from 1 to 4 and K 5 is the ratio of m 5 /s;
- R 73 to R 75 are independently selected from the group consisting of H, alkyl, aryl, alkenyl, alkoxy, amino, N-alkylamide, N-arylamide, hydroxy, halogen atom, acyl, acyloxy, acylamido, acyl-N-alkylamide, carboxyl, alkoxycarbonyl, or sulfonyl.
- Suitable amines for use in producing the above-mentioned anthrapyridone dyes in dyestuffs include aliphatic amine, alicyclic amine, alkoxyalkyl amine, amine having alkanol, diamine, amine of guanidine derivatives, and aromatic amine.
- anthraquinone dyes which absorb less than 500 nm and have colors such as yellow, orange and red, can be mixed with the neutral anthraquinone to produce black colors are described in the COLOR INDEX below.
- compositions suitable to produce the black dyes are reviewed immediately below.
- the neutral anthraquinone dye of the formula [I-4] monoazo complex dye of the formula [V-2]: anthraquinone yellow dye of the formula [a] in a weight ratio of 6:2:1.
- the neutral anthraquinone dye of the formula [I-5] monoazo complex dye of the formula [V-3]: anthraquinone yellow dye of the formula [b] in a weight ratio of 5:2:1.
- the neutral anthraquinone dye of the formula [II-4] monoazo complex dye of the formula [V-2]: anthraquinone yellow dye of the formula [a] in a weight ratio of 5:3:2.
- the neutral anthraquinone dye of the formula [I-2] anthrapyridone dye of the formula [VI-2]: monoazo complex dye of the formula [V-16]: in a weight ratio of 5:3:1.
- the resins utilized as the molded resins for laser welding may be any resin as long as they are thermoplastic resins. Polyamide resins and polyester resins are preferred from the point of view of heat-resistance and transmitting property, although other thermoplastic resins including polycarbonate resins can be used as well, alone, in combination with each other, or in combination with those preferable resins above.
- polyamide resins suitable for use in the present invention include condensation products of dicarboxylic acids and diamines, condensation products of aminocarboxylic acids and ring-opening polymerization products of cyclic lactams.
- dicarboxylic acids useful in this application include adipic acid, azelaic acid, sebacic acid, dodecanedioic acid, isophthalic acid and terephthalic acid.
- suitable diamines include tetramethylene diaamine, hexamethylene diamine, octamethylene diamine, nonamethylene diamine, dodecamethylene diamine, 2-methylpentamethylene diamine, 2-methyloctamethylene diamine, trimethylhexamethylene diamine, bis(p-aminocyclohexyl)methane, m-xylene diamine and p-xylene diamine.
- aminocarboxylic acid 11-aminododecanoic acid can be used.
- useful cyclic lactams include caprolactam and laurolactam.
- condensation products and ring-opening polymerization products include aliphatic polyamides such as nylon 6, nylon 66, nylon 46, nylon 610, nylon 612, nylon 11, nylon 12, semi-aromatic polyamides such as polymetaxylene adipamide (nylon MXD-6), polyhexamethylene terephthalamide (nylon 6T), polyhexamethylene isophthalamide (nylon 6I) and polynonamethylene terephthalamide (nylon 9T), and copolymers and mixtures of these polymers.
- nylon MXD-6 polymetaxylene adipamide
- nylon 6T polyhexamethylene terephthalamide
- nylon 6I polyhexamethylene isophthalamide
- nylon 9T polynonamethylene terephthalamide
- copolymers and mixtures of these polymers examples include nylon 6/66, nylon 66/61, nylon 61/6T and nylon 66/6T.
- polyester molding compositions useful for blending with colorants in the practice of the present invention are known in the art. These include polymers which are, in general, condensation products of dicarboxylic acids and diols.
- Dicarboxylic acids can be selected from the group consisting of adipic acid, azelaic acid, sebacic acid, dodecanedioic acid, terephthalic acid, isophthalic acid, naphthalenedicarboxylic acid and diphenyl dicarboxylic acid
- diols can be selected from the group consisting of ethylene glycol, prcpylene glycol, butanediol, hexanediol, neopentyl glycol, cyclohexanediol, and bisphenol A.
- Preferred polyesters include polyethylene terephtalate (PET), polypropylene terephthalate (3GT), polybutylene terephthalate (PBT), polyethylene 2,6- naphthalate (PEN), polycyclohexane dimethylene terephthalate (PCT) and copolymers and mixtures thereof.
- PET polyethylene terephtalate
- 3GT polypropylene terephthalate
- PBT polybutylene terephthalate
- PEN polyethylene 2,6- naphthalate
- PCT polycyclohexane dimethylene terephthalate
- copolymers some of dicarboxylic acids or some of diols can be added to the condensation products.
- Polyester polymers may be copolymerized a little amount of compnents like trimesic acid, trimellitic acid, pyromellitic acid, glycerol, and pentaerythritol which have more than 3 functional groups. Additional other polymers including poly
- a black colorant useful in the composition of the invention preferably comprises a mixture of neutral anthraquinone dye which imparts colors of blue, absorbs visible light with wavelength less than 700 nm and transmits a laser beam with wavelength at 800 nm to 1200 nm in infra-red region with at least other red dyes which transmit the laser beam with wavelength at 800 nm to 1200 nm in infra-red region, such as perinone dyes or monoazo complex dyes, at predetermined weight ratios.
- the black colorant containing the neutral anthraquinone dye is present in amounts of from 0.01 to 1% by weight, when the composition comprises polyamide 6 as at least the major component of the polyamide resin composition.
- the amount of the above-mentioned dye mixture may be determined by applications requiring different properties associated with the laser welding.
- the composition of the present invention may contain an inorganic filler or reinforcing agent that includes, for example, fibrous reinforcement such as glass fiber and carbon fiber, glass beads, glass flakes, talc, kaolin, wollastonite, silica, calcium carbonate, pottassium titanate and mica.
- fibrous reinforcement such as glass fiber and carbon fiber
- glass beads glass beads
- glass flakes glass flakes
- talc glass flakes
- kaolin kaolin
- wollastonite silica
- silica calcium carbonate
- pottassium titanate and mica
- glass fiber Preferable among them is glass fiber.
- Glass fibers suitable for use in the present invention are those generally used as reinforcing agents for thermoplastic resins and thermosetting resins.
- One or more optional compounds selected from a wide variety of compounds tailored for different applications of the resin compositions can be contained in the composition according to the present invention.
- additive compounds can include flame retardants, impact modifiers, viscosity modifiers, heat resistance improvers, lubricants, antioxidants and UV-and other stabilizers.
- the polyamide resin composition of the present invention may have such additive compounds in such amounts that they do not harm its characteristic properties.
- thermoplastic resin compositions suitable for laser welding which prepare transparent articles for laser beam to achieve welding together with the opaque article for laser beam.
- Suitable opaque articles and its compositions are described for example in DE-A-4432081.
- FIG. 1 is an illustration of a conventional welding arrangement.
- a laser beam 1 is transmitted through the first article 2 to the second article 3 containing laser beam absorbing combination, and the surface 4 of the article 3 that have absorbed the laser energy is melted and pressed with the surface of the first article 2 to weld them together.
- two thermoplastic components 5 and 6 must have different transmission and absorption coefficients and it is difficult to weld at surface 8 two articles having the same color.
- the laser beam 1 is applied to the surface 7 of the component 5 .
- FIGS. 3 and 5 there is shown a lower test piece 10 used in the laser welding test of these examples.
- the noted dimensions creates a notch in the test piece 10 .
- the upper test piece 9 is of the same construction and dimensions.
- FIGS. 4 and 6 there is shown the joinder of the upper test piece 9 to lower test piece 10 , and the movement of the laser 11 (in the direction of the arrow) to form the weld.
- Nylon 6 400 g Anthraquinone blue dye of the following formula [I-4] 0.36 g Perinone red dye of the following formula [IV-3] 0.28 g Anthraquinone yellow dye of the following formula [b] 0.16 g
- Test pieces were prepared and tested as described for Example A, above, and the results are reported in Table 7, below.
- the experimental piece obtained after keeping in an injection molding machine for 15 minutes was fadeless.
- Comparative Example C Nylon 6 (same as Example A) 400 g Anthraquinone violet dye of the following formula [c] 0.68 g Quinopthalone yellow dye of the following formula [d] 0.12 g
- Test pieces were prepared and tested as described for Example A, above, and the results are reported in Table 7, below. The experimental piece obtained after keeping in an injection molding machine for 15 minutes was faded and uneven. Comparative Example D Nylon 6 (same as Example A) 400 g Anthraquinone green dye of the following formula [e] 0.48 g Anthraquinone red dye of the following formula [f] 0.32 g
- Example E Nylon (same as Example A) 400 g Anthraquinone green dye of the following formula [e] 0.48 g Disazo red dye of the following formula [g] 0.32 g
- Test pieces were prepared and tested as described for Example A, above, and the results are reported in Table 7, below. The experimental piece obtained after keeping in an injection molding machine for 15 minutes was faded and uneven.
- Test pieces were prepared and tested as described for Example A, above, and the results are reported in Table 7, below. The experimental piece obtained after keeping in an injection molding machine for 15 minutes was faded and uneven. TABLE7 Comparative Comparative Comparative Example A Example B Example C Example D Example E Example F Transmission TA 0.96 0.97 0.90 0.95 0.95 0.95 TB 1.00 1.02 0.85 0.86 0.94 0.97 OD 2.42 2.42 2.45 2.42 2.42 2.39 Thermal Resistance ⁇ E 0.46 0.38 1.73 1.55 1.62 1.86 Moisture Resistance ⁇ E 0.75 0.68 1.08 1.56 2.73 1.14 TG/DTA Exothermic peak(° C.)/ 363.3/ 359.1/ 320.9/ 369.7/ 367.2/ 327.4/ Endothermic peak(° C.) none none 179.5 154.6 196.2 102.4
- Unreinforced polyester prepared from terephthalic acid and ethylene glycol the intrinsic viscosity of which is 0.85 when measured at 25° C. as a 1% solution in a mixed solution of phenol and dichlorobenzene with the weight ratio of 1/1) was dried at 120° C. for more than 8 h using a vacuum drying apparatus, and weighed according to the following formulation.
- Polyester 400 g Anthraquinone blue dye of the following formula [I-2] 0.40 g Perinone red dye of the following formula [IV-3] 0.24 g Anthraquinone yellow dye of the following formula [a] 0.16 g
- Test pieces were prepared and tested as described for Example G, above, and the results are reported in Table 8, below. The experimental piece obtained after keeping in an injection molding machine for 15 minutes was fadeless.
- Test pieces were prepared and tested as described for Example G, above, and the results are reported in Table 8, below. The experimental piece obtained after keeping in an injection molding machine for 15 minutes was fadeless. Comparative Example J Polyester (same as Example G) 400 g Anthraquinone violet dye of the following formula [c] 0.68 g Quinopthalone yellow dye of the following formula [d] 0.12 g
- Test pieces were prepared and tested as described for Example G, above, and the results are reported in Table 8, below. The experimental piece obtained after keeping in an injection molding machine for 15 minutes was faded and uneven. Comparative Example K Polyester (same as Example G) 400 g Anthraquinone green dye of the following formula [e] 0.48 g Anthraquinone red dye of the following formula [f] 0.32 g
- Example G Test pieces were prepared and tested as described for Example G, above, and the results are reported in Table 8 , below. The experimental piece obtained after keeping in an injection molding machine for 15 minutes was faded and uneven. Comparative Example L Polyester (same as Example G) 400 g Anthraquinone green dye of the following formula [e] 0.48 g Disazo red dye of the following formula [g] 0.32 g
- Test pieces were prepared and tested as described for Example G, above, and the results are reported in Table 8, below. The experimental piece obtained after keeping in an injection molding machine for 15 minutes was faded and uneven. Comparative Example M Polyester (same as Example G) 400 g Anthraquinone blue dye of the following formula [h] 0.53 g Perinone red dye of the following formula [IV ⁇ 3] 0.18 g Anthraquinone yellow dye of the following formula [a] 0.09 g
- Example G Example I
- Example J Example K
- Example M Transmission TA 0.88 0.93 0.93 0.92 0.93 0.92 0.93 TB 0.85 0.93 0.93 0.89 0.93 0.89 0.96 OD 1.78 1.81 1.80 1.86 1.78 1.85 1.78 Moisture 3.15 3.56 3.30 5.02 4.64 4.48 4.55 Resistance ⁇ E Sublimation Test 5.32 9.72 7.07 19.33 12.36 11.97 17.42 ⁇ E TG/DTA 532.8/ 363.3/ 359.1/ 320.9/ 369.7/ 367.2/ 327.4/ Exothermic none none none 179.5 154.6 196.2 102.4 peak(° C.)/ Endothermic peak(° C.)
- Transmittance (T) in the range of 400 nm to 1200 nm of the test plates with laser beams having respective wavelengths of 940 nm(Semiconductor laser) and 1064 nm (YAG laser) was measured using a U-3410 spectrometer producted by Hitachi with 60 ⁇ sphere photometer for wavelength from ultraviolet to nexr-infrared.
- the ratio (TA) of transmission with 940 nm: transmission with 1064 nm and the ratio (TB) of transmission with 940 nm: tamsmission of natural resin are determined and compared between the examples.
- Appearance of the test plates were evaluated by measuring Reflection Density (OD) of the test plates by Refelection Density meter TR-927 produced by Macbeth. Test plates having higher OD values are judged to have better surface smoothness and rich in gloss.
- TG and DTA of each test colorant powder were measured using TG / DTA analyzers (prodcued by Seiko Instrument, trade name:SII EXSTAR 6000) in a heating furnace that air is introduced into at 200 ml / min, of which temperature is raised from 30 to 55° C. at 10° C./min then when reached to at 550° C. for 28 minutes.
- TG / DTA analyzers prodcued by Seiko Instrument, trade name:SII EXSTAR 6000
- the amount of dye sublimation was determined by E between before and after white tape attached on each test plate being placed and kept in an oven at 140° C. for 3 hours and was mesaured using a colorimeter (produced by Juki, trade name: JP 7000).
- Fiberglass reinforced nylon 6 (Zytel® 73G30L, available from E. I. DuPont de Nemours and Co.) and dyes were dry-blended with the amount described in Table 9.
- the blended material was molded into two types of test pieces: one for mechanical properties, and the other for laser welding.
- Test pieces for mechanical properties were molded according to the IS03167 on the Toshiba IS 170FIII injection molding machine, with cylinder temperature set at 260° C. and mold temperature at 80° C.
- Test pieces for laser welding with dimensions illustrated as FIG. 3, were molded on the Sumitomo Juki 75T injection molding machine, with cylinder temperature set at 250° C. and mold temperature set at 80° C.
- Example N O P 73G30L kg 4.9925 4.9925 4.99 Blue dye formula [I ⁇ 2] 3.75 g Red dye formula [IV ⁇ 3] 2.25 g Yellow dye formula [a] 1.50 g Green dye formula [e] 4.50 g Red dye formula [g] 3.00 g Carbon black 10 g
- Fiberglass reinforced nylon 66 (Zytel® 7OG33HS1L, available from E. I. DuPont de Nemours and Co.) and dyes were dry-blended with the amount described in the Table 10.
- the blended material was molded into two types of test pieces: one for mechanical properties, and another for laser welding.
- Test pieces for mechanical properties were molded according to the ISO3167 on the Toshiba IS 170FIII injection molding machine, with cylinder temperature set at 280° C. and mold temperature at 80° C.
- Test pieces for laser welding with dimensions illustrated in FIG. 3, were molded on the Sumitomo Juki 75T injection molding machine, with cylinder temperature set at 270° C. and mold temperature set at 80° C.
- Example Q R S 70G33HS1L kg 4.9925 4.9925 4.99 Blue dye formula [I ⁇ 4] 3.75 g Red dye formula [IV ⁇ 3] 2.25 g Yellow dye formula [a] 1.50 g Green dye formula [e] 4.50 g Red dye formula [g] 3.00 g Carbon black 10 g
- Tensile strength MPa 199 207 207 Elongation % 3.4 3.8 3.2 Notched Charpy kJ/m 2 12.3 13.5 11.9 Laser Welding at 80 W 2.5 m/min kgf 97 75 — 5 m/min kgf 195 185 — 10 m/min kgf 194 187 —
- Fiberglass reinforced polyester prepared from terephthalic acid and ethylene glycol the intrinsic viscosity of which is 0.85 when measured at 25° C. as a 1% solution in a mixed solution of phenol and dichlorobenzene with the weight ratio of 1/1 and containing 30wt % chopped strand glass fibers 187H produced by Nippon Electric Glass Co., Ltd. based on a total weight of the polyester resin composition, and dried as described for xample G
- dyes were dry-blended with the amount described in Table 13.
- the blended material was molded into two types of test pieces: one for mechanical properties, and the other for laser welding.
- Test pieces for mechanical properties were molded according to the ISO3167 on the Toshiba IS 170FIII injection molding machine, with cylinder temperature set at 290° C. and mold temperature at 60° C.
- Test pieces for laser welding were molded on the Sumitomo Juki 75T injection molding machine, with cylinder temperature set at 280° C. and mold temperature set at 60° C.
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US10/047,686 US20030088076A1 (en) | 2000-11-13 | 2001-11-13 | Colored thermoplastic resin compositions for laser welding, specific neutral anthraquinone dyes as colorants therefor, and molded product therefrom |
US11/175,823 US7513947B2 (en) | 2000-11-13 | 2005-07-06 | Colored thermoplastic resin compositions for laser welding, specific neutral anthraquinone dyes as colorants therefor, and molded product therefrom |
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US24764700P | 2000-11-13 | 2000-11-13 | |
US10/047,686 US20030088076A1 (en) | 2000-11-13 | 2001-11-13 | Colored thermoplastic resin compositions for laser welding, specific neutral anthraquinone dyes as colorants therefor, and molded product therefrom |
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US11/175,823 Continuation-In-Part US7513947B2 (en) | 2000-11-13 | 2005-07-06 | Colored thermoplastic resin compositions for laser welding, specific neutral anthraquinone dyes as colorants therefor, and molded product therefrom |
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US10/053,074 Abandoned US20030045618A1 (en) | 2000-11-13 | 2001-11-13 | Colored thermoplastic resin compositions for laser welding, specific neutral anthraquinone dyes as colorants therefor, and molded product therefrom |
US10/047,686 Abandoned US20030088076A1 (en) | 2000-11-13 | 2001-11-13 | Colored thermoplastic resin compositions for laser welding, specific neutral anthraquinone dyes as colorants therefor, and molded product therefrom |
US11/135,782 Active 2026-08-25 US7485675B2 (en) | 2000-11-13 | 2005-05-23 | Colored thermoplastic resin compositions for laser welding, specific neutral anthraquinone dyes as colorants therefor, and molded product therefrom |
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US (3) | US20030045618A1 (zh) |
EP (2) | EP1353991B2 (zh) |
JP (2) | JP4040460B2 (zh) |
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CN (2) | CN1277871C (zh) |
AT (2) | ATE330991T1 (zh) |
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2001
- 2001-11-13 EP EP20010991091 patent/EP1353991B2/en not_active Expired - Lifetime
- 2001-11-13 AT AT01991091T patent/ATE330991T1/de not_active IP Right Cessation
- 2001-11-13 DK DK01991091T patent/DK1353991T3/da active
- 2001-11-13 AU AU2002230839A patent/AU2002230839A1/en not_active Abandoned
- 2001-11-13 US US10/053,074 patent/US20030045618A1/en not_active Abandoned
- 2001-11-13 DE DE2001621042 patent/DE60121042T3/de not_active Expired - Lifetime
- 2001-11-13 PT PT01991091T patent/PT1353991E/pt unknown
- 2001-11-13 WO PCT/US2001/048326 patent/WO2002038665A2/en active IP Right Grant
- 2001-11-13 CA CA 2423848 patent/CA2423848A1/en not_active Abandoned
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- 2001-11-13 WO PCT/US2001/048331 patent/WO2002038662A1/en active IP Right Grant
- 2001-11-13 EP EP20010991088 patent/EP1353990B2/en not_active Expired - Lifetime
- 2001-11-13 CN CNB018187552A patent/CN1277871C/zh not_active Expired - Lifetime
- 2001-11-13 KR KR20037006479A patent/KR100798266B1/ko active IP Right Grant
- 2001-11-13 AT AT01991088T patent/ATE329957T1/de not_active IP Right Cessation
- 2001-11-13 KR KR20037006490A patent/KR100798254B1/ko active IP Right Grant
- 2001-11-13 CN CNB018187757A patent/CN1250625C/zh not_active Expired - Lifetime
- 2001-11-13 DK DK01991088T patent/DK1353990T3/da active
- 2001-11-13 CA CA 2423940 patent/CA2423940A1/en not_active Abandoned
- 2001-11-13 JP JP2002541991A patent/JP4040460B2/ja not_active Expired - Lifetime
- 2001-11-13 JP JP2002541988A patent/JP4109109B2/ja not_active Expired - Lifetime
- 2001-11-13 US US10/047,686 patent/US20030088076A1/en not_active Abandoned
- 2001-11-13 PT PT01991088T patent/PT1353990E/pt unknown
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2005
- 2005-05-23 US US11/135,782 patent/US7485675B2/en active Active
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US20040144483A1 (en) * | 2002-09-24 | 2004-07-29 | Shuji Sugawara | Laser ray transmitting colored thermoplastic resin composition and method of laser welding |
US7153384B2 (en) * | 2002-11-06 | 2006-12-26 | Orient Chemical Industries, Ltd. | Laser ray transmitting colored thermoplastic resin composition and method of laser welding |
US7732512B2 (en) * | 2003-02-13 | 2010-06-08 | Orient Chemical Industries Co., Ltd. | Laser light transmitting colored polyolefin resin compositions and process for laser welding |
US20060142451A1 (en) * | 2003-02-13 | 2006-06-29 | Heihachi Yushina | Laser light transmitting colored polyolefin resin compositions and process for laser welding |
US7744804B2 (en) * | 2004-03-12 | 2010-06-29 | Orient Chemical Industries, Ltd. | Laser-transmissible composition and method of laser welding |
US20050203225A1 (en) * | 2004-03-12 | 2005-09-15 | Orient Chemical Ind., Ltd. | Laser-transmissible composition and method of laser welding |
US7483647B2 (en) * | 2005-12-27 | 2009-01-27 | Canon Kabushiki Kaisha | Cartridge having a molded resin complex |
US20070147879A1 (en) * | 2005-12-27 | 2007-06-28 | Canon Kabushiki Kaisha | Molded resin complex and method of producing the molded resin complex, and cartridge and method of producing the cartridge |
US20100065200A1 (en) * | 2006-01-18 | 2010-03-18 | Sarver Josephd E | Tetrabenzodiazadiketoperylene pigments in laser welding |
US20080103267A1 (en) * | 2006-10-31 | 2008-05-01 | General Electric Company | Infrared transmissive thermoplastic composition |
EP2500577A1 (de) * | 2011-03-12 | 2012-09-19 | Grundfos Management a/s | Heizungsumwälzpumpe |
WO2012123235A1 (de) * | 2011-03-12 | 2012-09-20 | Grundfos Management A/S | Heizungsumwälzpumpe |
US10047751B2 (en) | 2011-03-12 | 2018-08-14 | Grundfos Management A/S | Heating circulating pump |
US10781308B2 (en) | 2016-02-25 | 2020-09-22 | Mitsubishi Engineering-Plastics Corporation | Resin composition for laser welding and welded body thereof |
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