CN103649156B - 用于容器的涂料组合物 - Google Patents
用于容器的涂料组合物 Download PDFInfo
- Publication number
- CN103649156B CN103649156B CN201280031780.5A CN201280031780A CN103649156B CN 103649156 B CN103649156 B CN 103649156B CN 201280031780 A CN201280031780 A CN 201280031780A CN 103649156 B CN103649156 B CN 103649156B
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- China
- Prior art keywords
- coating
- coating composition
- weight
- acid
- bisphenol
- 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.)
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- 239000008199 coating composition Substances 0.000 title claims abstract description 60
- 238000000576 coating method Methods 0.000 claims abstract description 49
- 239000011248 coating agent Substances 0.000 claims abstract description 47
- 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 claims abstract description 30
- 229920005862 polyol Polymers 0.000 claims abstract description 23
- 235000013305 food Nutrition 0.000 claims abstract description 22
- 150000003077 polyols Chemical class 0.000 claims abstract description 18
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 14
- 229920000570 polyether Polymers 0.000 claims abstract description 13
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 11
- 229920000728 polyester Polymers 0.000 claims abstract description 11
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims abstract description 10
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 claims abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 28
- 150000005846 sugar alcohols Polymers 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 17
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- 239000011347 resin Substances 0.000 claims description 17
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- -1 polycyclic oxygen Compound Chemical class 0.000 claims description 12
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- 241001597008 Nomeidae Species 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229940106691 bisphenol a Drugs 0.000 claims description 9
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- 239000003431 cross linking reagent Substances 0.000 claims description 7
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- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 229930006000 Sucrose Natural products 0.000 claims description 5
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- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
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- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 claims description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 2
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- 239000004033 plastic Substances 0.000 claims description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims 1
- 229920001342 Bakelite® Polymers 0.000 claims 1
- UWKWMTBKFCNDDH-UHFFFAOYSA-N N(=NC=NN)CCCCCCN=NC=NN Chemical compound N(=NC=NN)CCCCCCN=NC=NN UWKWMTBKFCNDDH-UHFFFAOYSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000004637 bakelite Substances 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 39
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 abstract description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 33
- 239000002253 acid Substances 0.000 description 20
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 239000004645 polyester resin Substances 0.000 description 12
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- 239000000047 product Substances 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 235000011007 phosphoric acid Nutrition 0.000 description 7
- 229920000058 polyacrylate Polymers 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229920001568 phenolic resin Polymers 0.000 description 6
- 238000007711 solidification Methods 0.000 description 6
- 230000008023 solidification Effects 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
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- GTACSIONMHMRPD-UHFFFAOYSA-N 2-[4-[2-(benzenesulfonamido)ethylsulfanyl]-2,6-difluorophenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=C(F)C=C1SCCNS(=O)(=O)C1=CC=CC=C1 GTACSIONMHMRPD-UHFFFAOYSA-N 0.000 description 2
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
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- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical group CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 1
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- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
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- B65D1/00—Rigid or semi-rigid containers having bodies formed in one piece, e.g. by casting metallic material, by moulding plastics, by blowing vitreous material, by throwing ceramic material, by moulding pulped fibrous material or by deep-drawing operations performed on sheet material
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Landscapes
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- Ceramic Engineering (AREA)
- Paints Or Removers (AREA)
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- Details Of Rigid Or Semi-Rigid Containers (AREA)
Abstract
一种涂料组合物，其包含具有3至8羟基官能度的聚醚多元醇，和(ⅰ)一种含磷的酸与(ⅱ)一种聚环氧化物和/或聚酯的反应产物。该组合物可用于涂覆各种容器，如食品和饮料容器。该组合物可配制为基本上不含双酚A(BPA)，双酚A二缩水甘油醚(BADGE)和双酚A的其他衍生物。
Description
发明的技术领域
本发明涉及适用于涂覆各种容器，例如食品和饮料容器的组合物。
发明背景
多种涂料已用于涂覆食品和饮料容器的表面。例如，金属罐有时使用滚涂或板带涂覆操作涂覆，即平面或线圈，或适当基材例如钢或铝的片材，用合适的组合物涂覆并固化。然后将经涂覆的基材形成为罐体或罐端。或者，所述涂料组合物可例如通过喷涂、和浸渍来施涂到成型的罐上，然后固化。用于食品和饮料容器的涂料应优选能够高速施涂到基材，并在固化时提供必要的性质以进行需要的最终用途。例如，该涂应对于食品接触来说是安全的，并且具有对基材的优异的粘合力。
许多用于食品和饮料容器的涂料组合物是基于环氧树脂的，它们是双酚A的聚缩水甘油醚。包装涂料中的双酚A，不管是作为双酚A本身(BPA)；其衍生物，例如双酚A的二缩水甘油基醚(BADGE)，由双酚A和双酚F制备的环氧酚醛清漆树脂和多元醇都是有问题的。虽然目前的科学证据表明，可能从现有涂料释放的很少痕量的BPA或BADGE不会对人类有健康危害。然而有些人认为这些化合物对人体健康有害。因此，强烈希望将这些化合物从用于食品和饮料容器的涂料去除。因此，期望的是，用于食品或饮料容器的包装涂料组合物不含可萃取量的BPA，BADGE或BPA的衍生物，并仍具有优异的性质，例如对基材的优异的粘合力。
发明内容
本发明提供了一种涂料组合物，其包含：
(a)具有3到8羟基官能度的聚醚多元醇，和
(b)以下的反应产物：
(ⅰ)含磷的酸，和
(ⅱ)环氧树脂和/或聚酯多元醇。
本发明还提供了所得到的涂覆制品，包括：
(a)基材，和
(b)上述涂料组合物沉积在该基材上的涂层。
所述涂料组合物可以配制成使得其基本不含双酚A(BPA)及其衍生物，例如双酚A二缩水甘油基醚(BADGE)。
详细说明
如本文中使用的，除非有明确说明，所以数量,例如表达数值、范围、量、或百分比的挠性，可读作前面有词语“约”，即使该术语没有明确出现。此外，应注意，复数术语和/或短语涵盖它们的单数等价物，并且反之亦然。例如，“一种”聚合物、“一种”交联剂，和任何其它组分指的是一种或多种这些组分。
当指数值的任何数量范围时，该范围应理解为包含在所述最小和最大范围之间的各个和每一个数和/或分数。
本文使用的术语“多元醇”或其变型宽泛地指每分子具有平均两个或更更多个羟基的物质。术语“多元羧酸”指的是酸及其官能化衍生物，包括能存在的酸酐衍生物，和具有1-4个碳原子的低级烷基酯。
本文中使用的术语“聚合物”宽泛地指预聚物、低聚物以及均聚物和共聚物。术语“树脂”与“聚合物”可互换使用。
术语“丙烯酸类”和“丙烯酸酯”可互换使用(除非这样做会改变意图的含义)并包括丙烯酸、酸酐及其衍生物，例如它们的C1-C5烷基酯，低级烷基取代的丙烯酸，例如，C1-C2取代的丙烯酸，例如甲基丙烯酸，乙基丙烯酸等，和它们的C1-C5烷基酯，除非另有说明。术语“(甲基)丙烯酸类”或“(甲基)丙烯酸酯”意图涵盖丙烯酸类/丙烯酸酯和甲基丙烯酸类/甲基丙烯酸酯形式的所引述的材料，例如，(甲基)丙烯酸酯单体。术语“丙烯酸类聚合物”指的是由一种或多种丙烯酸类单体制备的聚合物。
如本文中使用的，“一种”和“至少一种”以及“一种或多种”可互换使用。因此，例如，包含“一种”聚合物的一种涂料组合物可以解释为指所述涂料组合物包括“一种或多种”聚合物。
如本文中使用的，分子量是通过凝胶渗透色谱法采用聚苯乙烯标准测定的。除非另有说明，分子量以数量平均计(Mn)。
聚醚多元醇具有3至8个，优选6至8个碳原子。合适的聚醚多元醇是具有3至8、优选6至8个羟基的多羟基化合物，与环氧烷的反应产物。合适的多羟基化合物的例子是季戊四醇，三羟甲基丙烷，二季戊四醇，双甘油和糖类如蔗糖、葡萄糖、乳糖和α-甲基葡糖苷。环氧烷的例子是那些含有2至4个碳原子的，如环氧乙烷，1,2-环氧丙烷，1,2-环氧丁烷和2,3-环氧丁烷和它们的混合物。
用于制备所述反应产物的方法是本领域公知的。通常环氧烷与多羟基化合物和合适的催化剂如胺或碱金属氢氧化物和任选的非反应性溶剂如芳族溶剂，例如甲苯或二甲苯，进行混合。调节多羟基化合物与环氧烷的比例，以使得到的羟值为150至600。这样的反应产物可从Dow Chemical Company以商标VORONOL和从Bayer MaterialScience以商标MULTRANOL商购得到。
通常，所述聚醚多元醇按重量计以基于涂料组合物中树脂固体含量的2％至50％的量存在于涂料组合物中。
涂料组合物中还存在含磷的酸与聚环氧化物和/或聚酯树脂的反应产物。
合适的聚环氧化物的分子中含有两个或更多个环氧基或环氧乙烷基，如多元醇的聚缩水甘油醚。典型的聚缩水甘油醚是具有基本不超过2、通常为约1.5至2的1,2-环氧当量，并且优选相对于环氧为双官能团的环氧封端的直链型环氧树脂。聚环氧化物通常具有至少为300，通常为300至2400克/摩尔的数均分子量(Mn)。
多元醇的聚缩水甘油醚的合适的例子可以通过使表卤代醇与多元醇，如二元醇，在碱性缩合和脱卤化氢催化剂，如氢氧化钠或氢氧化钾的存在下形成。有用的表卤代醇包括环氧溴丙烷，二氯丙醇，特别是环氧氯丙烷。
合适的多元醇可以是芳香族，脂肪族或脂环族的，包括但不限于，至少为二元酚的酚类，如二羟基苯类，例如间苯二酚，邻苯二酚和对苯二酚。可以使用的脂肪族多元醇包括，但不限于，甘醇如乙二醇，二甘醇，三甘醇，1,2-丙二醇，1,4-丁二醇，2,3-丁二醇，戊二醇，聚氧化烯二醇；多元醇，如山梨糖醇，甘油，1,2,6-己三醇，赤藓醇与三羟甲基丙烷；以及它们的混合物。合适的环脂族醇的例子是环己烷二甲醇，和优选的聚环氧化物是1,4-环己烷二甲醇的聚缩水甘油醚。
与含磷的酸反应的聚酯树脂中兼具羟基官能团和羧酸官能团。聚酯树脂含有羟基官能度和羧酸官能度。聚酯树脂典型地羟值为20-75mg KOH每克聚酯树脂，且酸值为15-20mg KOH每克聚酯树脂；均基于非挥发性固体测量。
聚酯树脂的数均分子量(Mn)为2000-10,000g/mol。
合适的聚酯树脂典型地通过根据已知方法的缩合(酯化)来制备[参见，例如，Zeno Wicks，Jr.，Frank N.Jones and S.Peter Pappas，Organic Coatings：Science and Technology，Vol.1，pp.122-132(John Wiley&Sons：New York，1992)]。聚酯树脂通常得自被多元酸或酸酐酯化的至少一种多官能醇(多元醇)的混合物，一般为二醇和三醇的混合物。多元酸组分包含α、β-烯属不饱和多元羧酸或酸酐。
聚酯树脂典型地由α、β-烯属不饱和多元羧酸，通常与芳族和/或脂族多元羧酸的混合物，以及多元醇组分，典型地为二醇和三醇的混合物来制备。多元醇和多元羧酸以期望的比例混合并利用标准酯化(缩合)工序反应以提供在聚酯树脂中具有羟基和羧酸的聚酯。
合适的多元羧酸或酸酐的实例包括，但不限于，马来酸酐，马来酸，富马酸，衣康酸，邻苯二甲酸，邻苯二甲酐，间苯二甲酸，偏苯三酸酐，对苯二甲酸，萘二酸，己二酸，壬二酸，琥珀酸，癸二酸和它们的各种混合物。
当使用时，芳族多元羧酸的用量为70重量%，典型地50-65重量%，基于多元羧酸或酸酐的总重量。
合适的二元醇、三元醇和多元醇的例子包括，但不限于，乙二醇，丙二醇，1,3-丙二醇，甘油，二甘醇，二甘醇，三甘醇，三羟甲基丙烷，三羟甲基乙烷，三丙二醇，新戊二醇，季戊四醇，1,4-丁二醇，三羟甲基丙烷，己二醇，环己烷二甲醇，聚乙二醇或聚丙二醇。
如上所述，多元醇成分是一种二元醇和三元醇的混合物。二元醇和三元醇的重量比通常为0.5～10：1。
多元醇成分与聚羧酸的当量比为0.9～1.1：1.0。
与聚环氧化物和/或聚酯树脂反应的含磷的酸可以是次膦酸，膦酸或优选为磷酸。磷酸可以是水溶液的形式，例如，85重量%的水溶液，或者可以是100％的磷酸或超磷酸。该酸以相对于每当量聚环氧化物的环氧基和聚酯的羟基约为0.2-0.5当量的磷酸量提供，也就是说，0.2-0.45P-OH基团每个环氧乙烷基团或每聚酯的羟基。含磷的酸与聚环氧化物和/或聚酯的反应通常在有机溶剂中进行。用于包含聚环氧化物的反应的有机溶剂优选为一种羟基官能化合物，典型的为一种单官能化合物。羟基官能化合物中可以使用的是脂族醇，脂环醇和烷基醚醇。特别优选的羟基官能化合物包括正丁醇和2-丁氧基乙醇。为了与聚酯反应，所述有机溶剂通常是芳族溶剂，酮或酯。其例子包括甲基乙基酮，甲基异丁基酮，乙二醇丁醚乙酸酯和丙二醇甲醚醋酸酯。有机溶剂典型地具有65至250℃的沸点。用于反应的有机溶剂通常以基于含磷的酸、环己烷二甲醇的聚缩水甘油醚和有机溶剂的总重量的约20％至50重量%的含量存在。
反应物和有机溶剂通常在50℃到95℃之间的温度下混合。一旦反应物们接触，将反应混合物保持在优选为90℃至200℃的温度下。该反应通常可以继续进行约45分钟至6小时的时间。
以涂料组合物中树脂固体的重量为基准，反应产物通常在涂料组合物中以按重量计最高达10％重量，优选为0.1～5％重量的量存在。低于0.1重量%的数量会导致涂料组合物对基体较差的粘合力，而高于10重量%不会提供任何附加的优点。
除聚醚多元醇之外，涂料组合物可任选地含有一种辅助聚合物。这些辅助聚合物的实例是丙烯酸类聚合物和聚酯聚合物。
丙烯酸类聚合物优选为得自一种或多种丙烯酸类单体的聚合物。此外，可以使用得自丙烯酸单体的丙烯酸类聚合物的共混物。优选的单体有丙烯酸，丙烯酸甲酯，丙烯酸乙酯，丙烯酸丙酯，丙烯酸丁酯，丙烯酸戊酯，丙烯酸己酯，甲基丙烯酸，甲基丙烯酸甲酯，甲基丙烯酸乙酯，甲基丙烯酸丙酯，甲基丙烯酸丁酯，甲基丙烯酸戊酯和甲基丙烯酸己酯。丙烯酸类聚合物还可含有羟基基团，其典型地得自羟基取代的丙烯酸类或甲基丙烯酸酯。实例包括丙烯酸羟乙基酯和甲基丙烯酸羟丙酯。丙烯酸类聚合物组分的重均分子量优选为至少5,000g/mol，更优选15,000-100,000g/mol。丙烯酸类聚合物典型地酸值为30-70，例如40-60mg KOH/g；羟值为0-100，例如0-70mg的KOH/g，且玻璃化转变温度(Tg)为-20至+100℃，例如+20至+70℃。
聚酯聚合物通过本领域熟知的方法制备，包括一种或多种多元羧酸与一种或多种多元醇的缩聚反应。合适的多元羧酸的实例有邻苯二甲酸，间苯二甲酸，对苯二甲酸，1,4-环己烷二酸，琥珀酸，癸二酸，甲基四氢邻苯二甲酸，甲基六氢邻苯二甲酸，四氢邻苯二甲酸，十二烷二酸，己二酸，壬二酸，萘二酸，均苯四酸，二聚体脂肪酸和/或偏苯三酸。
多元醇组分例如选自二醇或三醇，优选选自它们的混合物。合适的多元醇的实例包括乙二醇，1,3-丙二醇，二乙二醇，二丙二醇，三乙二醇，1,4-丁二醇，2-甲基-1,3-丙二醇，1,4-环己烷二甲醇，1,6-己二醇，新戊二醇，三羟甲基丙烷和甘油。聚酯优选的数均分子量为1000-20,000g/mol。
聚酯聚合物典型地酸值为0-20，例如0-5mg的KOH/g，羟值为50-200，例如70-150mg的KOH/g，玻璃化转变温度(Tg)为-20℃至+50℃，例如-10℃至+40℃。
当存在辅助多元醇时，其存在量最高达90重量%，通常为10～90重量%，基于涂料组合物中树脂固体的重量。
通常在组合物中存在固化剂，其可与聚醚多元醇和辅助多元醇起反应。
可使用的固化剂是苯酚塑料或苯酚-甲醛树脂，以及氨基塑料或三嗪-甲醛树脂。苯酚-甲醛树脂优选为酚醛甲阶型。合适的苯酚的实例有苯酚本身，丁基苯酚，二甲酚和甲酚。经常使用甲酚-甲醛树脂，其典型地被丁醇醚化。对于制备苯酚树脂的化学，参考“The Chemistryand Application of Phenolic Resins or Phenoplasts"，Vol.V，Part I，Dr.Oldring编辑；John Wiley&Sons/Cita TechnologyLimited，London，1997。市售苯酚树脂的实例有PR285和BR612，以及以商标典型地BAKELITE6581LB出售的那些树脂。
氨基塑料树脂的实例通过使三嗪例如三聚氰胺或苯并胍胺与甲醛反应形成的那些。优选地，这些缩合物典型地用甲醇、乙醇、丁醇以及它们的混合物醚化。对于制备和使用氨基塑料树脂的化学，参见“The Chemistry and Applications of Amino Crosslinking Agentsor Aminoplast”，Vol.V，Part II，第21页ff.，Dr.Oldring编辑；John Wiley&Sons/Cita Technology Limited，London，1998。这些树脂以商标例如MAPRENAL MF980市售，以及以商标例如CYMEL303和CYMEL1128，可购自Cytec Industries。典型地，交联剂的存在量为5至50重量％，优选为20至40重量%，这种重量百分比基于涂料组合物中的总树脂固体的重量。
其它任选的成分可以包括在该涂料组合物。通常，涂料组合物将包含稀释剂，诸如水或有机溶剂或水和有机溶剂的混合物，以溶解或分散树脂粘合剂，和含磷的酸与聚环氧化物和/或聚酯多元醇的反应产物。有机溶剂被选择为具有足够的挥发性，以在固化过程，如在175-205℃约5-15分钟的加热过程中，基本完全从涂料组合物中蒸发。合适的有机溶剂的例子有脂肪烃，如矿物油和高闪点的VM＆P石脑油；芳香族烃类，如苯，甲苯，二甲苯和溶剂石脑油100，150，200等；醇类，例如乙醇，正丙醇，异丙醇，正丁醇等；酮类，如丙酮，环己酮，甲基异丁基酮等；酯类，如乙酸乙酯，乙酸丁酯等；二醇，例如乙二醇，乙二醇醚，例如甲氧基丙醇和乙二醇单甲醚和乙二醇单丁醚等。各种有机溶剂的混合物也可使用。对于含有酸官能辅助聚合物的如酸官能丙烯酸类聚合物的水性组合物，所述酸基团至少部分地用胺中和，以帮助在含水介质中的辅助聚合物的分散或溶解。当存在时，稀释剂在涂料组合物中，以基于涂料组合物的总重量，约20至80，如30至70重量%的数量使用。
另一种通常存在于涂料组合物中的任选的成分，是催化剂，用以提高涂料组合物的固化或交联的速率。通常的酸催化剂可以使用，通常以约0.05至5重量％的量存在。合适的催化剂的例子是十二烷基苯磺酸，甲磺酸，对甲苯磺酸，二壬基萘二磺酸和苯基膦酸。已经发现，由于含磷的酸与聚环氧化物和/或聚酯的反应产物的存在，在本发明涂料组合物中的酸催化剂的量与通常预期的不一样大。这些反应产物是酸性的，并已发现有助于涂料组合物的固化。
另一种可用的任选的成分是润滑剂，例如，通过赋予经涂覆的金属基材的片材以润滑性而便于制造金属闭合体的蜡。优选的润滑剂包括，例如，巴西棕榈蜡和聚乙烯型润滑剂。如使用，润滑剂优选以基于所述涂料组合物的树脂固体重量的至少0.1重量%存在于所述涂料组合物中。
另一种可用的任选的成分是颜料，例如二氧化钛。如使用，颜料存在于所述涂料组合物中的量为不大于70重量%，优选不大于40重量%，基于所述涂料组合物中固体的总重量。
表面活性剂可以任选地加入所述涂料组合物以辅助流动和润湿基材。合适的表面活性剂的实例包括，但不限于，壬基苯酚聚醚和盐。如使用，表面活性剂以基于所述涂料组合物的树脂固体重量的至少0.01%且不大于10%的量存在。
在某些实施方式中，用于实施本发明的组合物基本上不含，可以实质上不含，并且可完全不含双酚A及其衍生物或残留物，包括双酚A(“BPA”)和双酚A二缩水甘油基醚(“BADGE”)。此类组合物有时候被称为“无有意BPA的”，因为BPA，包括其衍生物或残留物，不是有意加入的，而是由于从环境不可避免的污染而可能以痕量存在的。所述组合物还可以基本上不含，以及可以实质上不含，并且可完全不含双酚F及其衍生物或残留物，包括双酚F和双酚F二缩水甘油基醚(“BPFG”)。本文中使用的术语“基本上不含”是指所述组合物含有少于1000份每百万份(ppm)，“实质上不含”是指少于100ppm，且“完全不含”是指少于20份每十亿份(ppb)的任何上述化合物、其衍生物或残留物。
本发明的涂料组合物可以施涂到所有种类的容器，并且特别适用于食品和饮料罐(例如，两件式罐，三件式罐等)。除了食品和饮料容器，所述涂料组合物还可以施涂到用于气溶胶引用的容器，例如除臭剂和头发喷雾剂。
两件式罐通过使罐体(典型地为拉伸金属本体)与罐端(典型地为拉伸金属端)连接而制造。本发明的涂料适用于食品或饮料接触的情形，并且可用于所述罐的内部或外部。它们特别适于喷涂、液体涂层、洗涂层，片材涂层，清漆上涂层和边缝涂层。
喷涂包括将所述涂料组合物引入预成型包装容器的内部或外部。典型的适于喷涂的预成型包装容器包括食品罐，啤酒和饮料容器等。然后将经喷涂的预成型容器进行加热以除去残余溶剂并使涂层硬化。
滚涂被描述为由金属(例如，钢或铝)组成的线圈的涂覆，其典型地通过辊涂施加。一旦涂覆，对涂覆线圈进行短的热、紫外线、和/或电磁固化循环，从而使涂层硬化(例如，干燥和固化)。滚涂提供这样的涂覆的金属(例如，钢和/或铝)基材，其可以被制造成制品，例如两件式拉伸食品罐，三件式食品罐，食品罐端，拉伸和冲拔罐，饮料罐端等。
洗涂在商业上被描述为对两件式拉伸和冲拔(“D&I”)罐的外部涂覆保护性涂层的薄层。这些D&I罐的外部通过使预成型两件式D&I罐穿过涂料组合物的幕帘而被“洗涂”。当穿过幕帘时，将罐翻转，即将罐的开口端置于“向下”的位置。该涂料组合物的幕帘具有“瀑布状”外观。一旦这些罐穿过该涂料组合物的幕帘，液体涂层材料有效地涂覆每个罐的外部。过量的涂料通过使用“气刀”除去。一旦将期望量的涂料施加到每个罐的外部，使每个罐穿过热、紫外线和/或电磁固化炉以硬化(例如，干燥和固化)该涂料。经涂覆的罐在固化炉区域内的停留时间典型地为1分钟至5分钟。该炉内的固化温度典型地范围在150℃-220℃。
板带涂覆被描述为涂覆被预切割成正方形或矩形“片材”的各种材料(例如，钢或铝)的独立工件。这些片材的典型尺寸大约为一个平方米。一旦涂覆，将各片材固化。一旦硬化(例如，干燥和固化)，收集经涂覆的基材的片材并准备用于后续制造。板带涂覆提供经涂覆的金属(例如，钢或铝)基材，它们可以成功地制造成成型制品，例如两件式拉伸食品罐，三件式食品罐，食品罐端，拉伸和冲拔罐，饮料罐端等。
边缝涂层被描述为将液体涂料喷涂到成型的三件式食品罐的焊接区域。当制备三件式食品罐时，将经涂覆的基材的矩形工件成型为圆柱体。通过热焊接将矩形的每一侧焊接而使圆柱体的形成是永久性的。一旦焊接，各罐典型地需要一层液体涂料来保护暴露的“焊接区”不会随后腐蚀或对所含有的食品物料有其它影响。起这种作用的液体涂料被称作“边缝带条”。典型的边缝带条是喷涂的，并且通过来自焊接操作的残余热以及少量热、紫外线、和/或电磁炉的热而快速固化。
实施例
提供以下实施例以帮助理解本发明，它们不应解释为限制本发明的范围。除非另有说明，所有份数和重量百分比以重量计。
实施例A
磷酸和环己烷二甲醇二缩水甘油醚的反应产物
将110.14克的85％的正磷酸和89.30克丁醇加入到烧瓶中。在氮气惰性层中将混合物加热至230℉(110℃)。当达到该温度时，氮气层被关闭，将463.30克的1,4-环己烷二甲醇二缩水甘油醚(0.286当量磷酸每当量环氧)和151.27克丁醇的预混物在2小时10分钟内加入。在添加过程中，配合料温度保持在低于245℉(118℃)。在完成2小时10分钟进料后，将13.7克丁醇加入到烧瓶中，并将温度降低至219℉(104℃)，并另外保持2小时。将另外17.30克丁醇加入到烧瓶中，所得的反应产物具有65.91重量％的树脂固体含量。
实施例1
包括如下成分混合物的透明清漆：
1含羧酸基团的丙烯酸类树脂，其部分被胺中和并分散在水中。
2来自于Dow Chemical Co的VORANOL360。
3来自于Cytec Industries的甲基化三聚氰胺交联剂。
将这些成分以所示的顺序加入到容器中并温和搅拌，以形成透明清漆。
透明清漆通过0.006线绕拉杆施用于扁平干净的无涂层的铝制饮料罐上。被涂覆的罐在400℉(204℃)的电动通风炉中烘烤180秒，然后在沸腾的去离子水中浸泡30分钟。被涂覆的罐随后用毛巾干燥，交叉划线以形成100个3×3毫米的正方形。将Scotch610带贴在划线区域上并擦亮以粘附到涂层上。在快速拉力下将带移除。在面板的划线区域没有附着物损失。
如上所述的被涂覆的罐也在180℉(82℃)的1％的Joy洗涤剂溶液中浸渍10分钟。被涂覆的罐被干燥并如上所述测试了粘合力。在面板的划线区域没有附着物损失。
实施例2-4
准备一系列的容器涂料组合物。第一种是实施例1的含有蔗糖多元醇的组合物。为了比较的目的，第二种组合物(重量)通过采用相等份数的双酚A多元醇(双酚A与环氧乙烷(1～6摩尔比)的缩合物，从BASF作为MACOL98B获得)代替蔗糖多元醇而制备。第三种组合物为对照标准且不含蔗糖多元醇或双酚A多元醇。
这些组合物通过0.006线绕拉杆施用于扁平干净无涂层的铝制饮料罐上。被涂覆的罐在400℉(204℃)的电动通风炉中烘烤40秒。将被涂覆的罐从烘箱中取出，冷却并评价其粘合力。结果如下：
| 实施例编号 | 粘合力(MEK来回刮擦)1 |
| 2 | 95 |
| 3(比较例) | 90 |
| 4(对照) | 30 |
1用甲基乙基酮(MEK)浸泡的棉花垫被包裹在2磅重的球头锤的球上，并在涂层上来回移动，直到涂层被严重破坏。
Claims (25)
1.一种涂料组合物，包含：
(a)具有3至8羟基官能度的聚醚多元醇，和
(b)以下的反应产物：
(i)含磷的酸，和
(ii)聚环氧化物，
其中所述聚醚多元醇包括糖类与环氧烷的反应产物，所述聚环氧化物包括脂族二醇的二缩水甘油醚。
2.根据权利要求1所述的涂料组合物，其中所述聚醚多元醇具有6至8的羟基官能度。
3.根据权利要求1所述的涂料组合物，其中所述糖类包括蔗糖。
4.根据权利要求1所述的涂料组合物，其中所述环氧烷包括环氧乙烷、环氧丙烷和/或环氧丁烷。
5.根据权利要求1所述的涂料组合物，其中所述聚醚多元醇具有150至600的羟值。
6.根据权利要求1所述的涂料组合物，其中所述含磷的酸是磷酸。
7.根据权利要求1所述的涂料组合物，其基本上不含双酚A和双酚A的衍生物。
8.根据权利要求1所述的涂料组合物，其完全不含有双酚A和双酚A的衍生物。
9.根据权利要求1所述的涂料组合物，其中二醇包括环己烷二甲醇。
10.根据权利要求1所述的涂料组合物，其中所述含磷的酸的用量为0.2-0.5当量每当量聚环氧化物中的环氧基。
11.根据权利要求1所述的涂料组合物，其中所述聚醚多元醇以基于涂料组合物中树脂固体的重量的2重量％至50重量％的量存在。
12.根据权利要求1所述的涂料组合物，其中(b)以基于树脂固体重量最高达10重量％的量存在。
13.根据权利要求1所述的涂料组合物，其进一步包含含有丙烯酸类聚合物和/或聚酯聚合物的多元醇。
14.根据权利要求1所述的涂料组合物，其进一步包含交联剂。
15.根据权利要求14所述的涂料组合物，其中所述交联剂包括氨基塑料和/或酚醛塑料。
16.根据权利要求13所述的涂料组合物，其中所述多元醇以树脂固体重量的10至90重量％的量存在。
17.根据权利要求14所述的涂料组合物，其中所述交联剂以基于涂料组合物中树脂固体重量的5至50重量％的量存在。
18.根据权利要求1所述的涂料组合物，其中所述脂族二醇为脂环族二醇。
19.涂覆制品，包括：
(a)基材，和
(b)沉积在所述基材的至少一部分上的根据权利要求1的涂料组合物。
20.根据权利要求19所述的涂覆制品，其中所述基材是容器。
21.根据权利要求20所述的涂覆制品，其中所述容器用于食品或饮料。
22.根据权利要求21所述的涂覆制品，其中所述基材是罐。
23.根据权利要求22所述的涂覆制品，其中所述涂料被沉积在罐的外壁上。
24.根据权利要求19所述的涂覆制品，其中所述涂料组合物基本上不含双酚A及其衍生物。
25.根据权利要求19所述的涂覆制品，其中所述涂料组合物不含双酚A及其衍生物。
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| BR122015001646B1 (pt) | 2011-02-07 | 2021-06-15 | Swimc Llc | Composição de revestimento, artigo, e, método |
| US10526502B2 (en) | 2012-08-09 | 2020-01-07 | Swimc Llc | Container coating system |
| JP2015527455A (ja) | 2012-08-09 | 2015-09-17 | ヴァルスパー・ソーシング・インコーポレーテッド | 容器及び他の物品のための組成物並びにその使用方法 |
| JP6538036B2 (ja) * | 2013-10-17 | 2019-07-03 | ヴァルスパー・ソーシング・インコーポレーテッド | ジ（アミド（アルキル）フェノール）化合物、及びその化合物から形成されるポリマー |
| EP3131965B1 (en) | 2014-04-14 | 2024-06-12 | Swimc Llc | Methods of preparing compositions for containers and other articles and methods of using same |
| WO2015179064A1 (en) | 2014-05-19 | 2015-11-26 | Valspar Sourcing, Inc. | Polyethers containing non-bisphenolic cyclic groups |
| EP3026088A1 (en) | 2014-11-27 | 2016-06-01 | PPG Industries Ohio, Inc. | Coating composition comprising a binder formed from polyester and a phosphorus acid |
| BR112017013725B1 (pt) * | 2014-12-31 | 2022-01-04 | Akzo Nobel Coatings International B.V. | Composição de revestimento com base em solvente orgânico e substrato metálico revestido |
| EP3088318A1 (en) * | 2015-04-30 | 2016-11-02 | PPG Industries Ohio, Inc. | Pull tabs for food and/or beverage cans |
| TWI614275B (zh) | 2015-11-03 | 2018-02-11 | Valspar Sourcing Inc | 用於製備聚合物的液體環氧樹脂組合物 |
| US10370151B2 (en) * | 2016-01-15 | 2019-08-06 | Ppg Industries Ohio, Inc. | Containers coated with compositions having enhanced heat-aging properties |
| US20200181317A1 (en) * | 2016-06-27 | 2020-06-11 | Warner Babcock Institute For Green Chemistry, Llc | Bisphenol A-Free Crosslinked Polymer Composition |
| CN111051445B (zh) * | 2017-08-25 | 2023-05-26 | 宣伟投资管理有限公司 | 用于容器和其它制品的粘附促进剂和组合物 |
| EP3628710A1 (en) | 2018-09-26 | 2020-04-01 | Holland Novochem Technical Coatings B.V. | Coating composition |
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2011
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2012
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- 2012-05-22 KR KR1020137034012A patent/KR20140016393A/ko not_active Ceased
- 2012-05-22 AU AU2012258928A patent/AU2012258928B2/en not_active Ceased
- 2012-05-22 PL PL12727959T patent/PL2714765T3/pl unknown
- 2012-05-22 BR BR112013030146A patent/BR112013030146A2/pt not_active Application Discontinuation
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- 2012-05-22 RU RU2013156829/04A patent/RU2561733C2/ru not_active IP Right Cessation
- 2012-05-22 CA CA2836801A patent/CA2836801C/en not_active Expired - Fee Related
- 2012-05-22 EP EP12727959.4A patent/EP2714765B1/en not_active Not-in-force
- 2012-05-22 CN CN201280031780.5A patent/CN103649156B/zh not_active Expired - Fee Related
- 2012-05-23 TW TW101118413A patent/TWI465529B/zh not_active IP Right Cessation
-
2013
- 2013-11-21 ZA ZA2013/08773A patent/ZA201308773B/en unknown
-
2016
- 2016-11-03 US US15/342,201 patent/US20170051174A1/en not_active Abandoned
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4059550A (en) * | 1976-07-06 | 1977-11-22 | Celanese Polymer Specialties Company | Aqueous dispersions of polyhydroxy polyether resins and aminoplast resins |
| US4425451A (en) * | 1982-09-29 | 1984-01-10 | Desoto, Inc. | Epoxy-phosphate aqueous dispersions |
| US4461857A (en) * | 1982-09-29 | 1984-07-24 | Desoto, Inc. | Thermosetting aqueous coating compositions containing epoxy-phosphate dispersions |
| US4739020A (en) * | 1985-12-13 | 1988-04-19 | Ppg Industries, Inc. | Flexible primer composition |
| US6159549A (en) * | 1997-12-17 | 2000-12-12 | Ppg Industries Ohio, Inc. | Flexible phosphatized polyester-urethane primers and improved coating systems including the same |
Also Published As
| Publication number | Publication date |
|---|---|
| CN103649156A (zh) | 2014-03-19 |
| NZ618115A (en) | 2015-06-26 |
| ZA201308773B (en) | 2015-08-26 |
| CA2836801A1 (en) | 2012-11-29 |
| MY167879A (en) | 2018-09-26 |
| RU2013156829A (ru) | 2015-06-27 |
| US20170051174A1 (en) | 2017-02-23 |
| EP2714765B1 (en) | 2017-10-11 |
| TWI465529B (zh) | 2014-12-21 |
| WO2012162299A1 (en) | 2012-11-29 |
| MX2013013651A (es) | 2014-08-01 |
| SG195057A1 (en) | 2013-12-30 |
| US20120301646A1 (en) | 2012-11-29 |
| RU2561733C2 (ru) | 2015-09-10 |
| ES2647890T3 (es) | 2017-12-27 |
| CA2836801C (en) | 2016-10-18 |
| TW201302941A (zh) | 2013-01-16 |
| EP2714765A1 (en) | 2014-04-09 |
| BR112013030146A2 (pt) | 2016-09-27 |
| PL2714765T3 (pl) | 2018-03-30 |
| AU2012258928B2 (en) | 2014-10-09 |
| MX360757B (es) | 2018-11-14 |
| KR20140016393A (ko) | 2014-02-07 |
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