CN102333833A - 羟基官能油多元醇和由羟基官能油多元醇制备的涂料组合物 - Google Patents

羟基官能油多元醇和由羟基官能油多元醇制备的涂料组合物 Download PDF

Info

Publication number
CN102333833A
CN102333833A CN2010800096894A CN201080009689A CN102333833A CN 102333833 A CN102333833 A CN 102333833A CN 2010800096894 A CN2010800096894 A CN 2010800096894A CN 201080009689 A CN201080009689 A CN 201080009689A CN 102333833 A CN102333833 A CN 102333833A
Authority
CN
China
Prior art keywords
oil
hydroxyl
functional
coating composition
mixture
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.)
Granted
Application number
CN2010800096894A
Other languages
English (en)
Other versions
CN102333833B (zh
Inventor
G·P·克劳恩
G·J·斯特拉
K·J·加德纳
D·J·特尔福德
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Akzo Nobel Coatings International BV
Original Assignee
Akzo Nobel Coatings International BV
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Akzo Nobel Coatings International BV filed Critical Akzo Nobel Coatings International BV
Publication of CN102333833A publication Critical patent/CN102333833A/zh
Application granted granted Critical
Publication of CN102333833B publication Critical patent/CN102333833B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/04—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to gases
    • B05D3/0433—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to gases the gas being a reactive gas
    • B05D3/0453—After-treatment
    • B05D3/046—Curing or evaporating the solvent
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
    • B32B27/285—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42 comprising polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F289/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds not provided for in groups C08F251/00 - C08F287/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/14—Unsaturated oxiranes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
    • 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
    • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • 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
    • C09D191/00—Coating compositions based on oils, fats or waxes; Coating compositions based on derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
    • C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08L61/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
    • C08L61/24—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with urea or thiourea
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08L61/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08L61/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08L61/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Paints Or Removers (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)

Abstract

公开了可用于生产涂料组合物和涂覆表面的羟基官能油多元醇。在某些实施方案中，所述涂料组合物用于涂覆基材如食品和饮料储存用包装材料等。羟基官能油多元醇可通过使环氧化植物油与羟基官能材料在酸催化剂存在下反应而制备。涂料组合物可通过用交联剂交联所述羟基官能油多元醇而制备。

Description

羟基官能油多元醇和由羟基官能油多元醇制备的涂料组合物
发明背景
1.发明领域
本发明涉及羟基官能油多元醇，由所述羟基官能油多元醇形成的涂料组合物，用所述涂料组合物涂覆基材的方法以及用所述涂料组合物涂覆的基材。
2.相关技术描述
现有技术主要基于用氨基树脂和酚醛塑料固化的环氧树脂技术。由双酚A基环氧树脂形成的涂料组合物已经用于涂覆食品和饮料用包装材料和容器。然而，在一些消费者和品牌持有人中存在对用于食品和饮料用包装材料和容器中的不含或基本不含双酚A的涂料组合物的需求。
美国专利号5,728,796公开了一种使含环氧化物的化合物与含羟基的脂族化合物在磺酸催化剂存在下反应的方法。该方法用于形成高分子量的环氧树脂。
美国专利号4,012,559公开了一种可辐射固化的涂料组合物，其含有丙烯酸类共聚物、分子量不大于2,000的多官能化合物和环氧化植物油。描述了所述固化组合物可涂覆于金属上以形成预涂覆金属产品。
Guo等人，基于大豆油的硬质聚氨酯泡沫(Rigid Polyurethane FoamsBased on Soybean Oil)，Journal of Applied Polymer Science，第77卷，467-473(2000)教导了环氧化大豆油与甲醇反应以形成环氧化大豆油多元醇，其用于制备在绝热和包装材料中使用的聚氨酯泡沫。
美国专利申请公布号2008/0302694公开了一种可辐射固化的涂料组合物，其含有由环氧化植物油和羟基官能丙烯酸酯或羟基官能甲基丙烯酸酯在磺酸催化剂存在下反应制备的环氧化植物油低聚物。该组合物可用作食品储存中包装材料用涂料。
美国专利号4,212,781公开了通过与可共聚单体在引发剂存在下反应而改性环氧树脂的方法。接枝聚合物通过将加成聚合物接枝到环氧树脂的脂族主链上而由环氧树脂形成。公开了所述方法用于制备涂料组合物用聚合物共混物。
对生产不含双酚A或基本不含双酚A的包装材料用涂料存在需要。本发明羟基官能油多元醇满足该需要且可以用于制备尤其适合作为用于食品和饮料包装材料和容器的包装材料用涂料的涂料组合物。可以配制它们以提供相比于某些市售环氧涂料体系而言更高的施用固体和改进的耐腐蚀性。
发明概述
本发明技术能够提供相比于某些现有技术涂料而言更好耐腐蚀性和更高固体的涂料。更高固体在单程操作中允许更宽的涂覆范围。本发明技术还可以提供作为优异成膜剂的高分子量的尚未胶凝的涂料组合物。
本发明包括生产羟基官能油多元醇的方法。该类方法可以在单一反应器或多个反应器中进行。在本发明某些实施方案中，羟基官能油多元醇通过包括使环氧化植物油与羟基官能材料在酸催化剂存在下反应的步骤的方法制备。
本发明还包括由羟基官能油多元醇制备的涂料组合物。在某些实施方案中，涂料组合物通过包括如下步骤的方法制备：使环氧化植物油与羟基官能材料在酸催化剂存在下反应以形成羟基官能油多元醇和用交联剂交联羟基官能油多元醇以形成涂料组合物。
本发明进一步包括通过如下步骤涂覆基材的方法：混合羟基官能油多元醇与交联剂以形成混合物，将所述混合物施加至基材和交联所述混合物。本发明还包括用所述涂料组合物涂覆的基材。在某些实施方案中，所述基材为罐或包装材料。
发明详述
如上述实施方案和该公开的其他实施方案以及本文所述权利要求书中所用，下列术语通常具有所指含义，但如果本发明权益通过推导出下列术语的更宽含义实现，则这些含义不意味着限制本发明范围。
除了操作实施例外，或除非另有说明，所有表示成分的量、反应条件及所述用于说明书和权利要求书中的那些数值应理解为在所有情况下以术语“约”修正。因此，除非有相反说明，在以下说明书和所附权利要求书中所述的数值参数为可根据通过本发明获得的所需性能改变的近似值。至少而且不打算限制等同于权利要求书范围的教条的应用，各数值参数应根据有效位数和常规四舍五入法解释。尽管阐述本发明宽范围的数值范围和参数为近似值，但是在具体实施例中阐述的数值是尽可能准确地记录的。然而，任何数值本身都含有不可避免地在其各自测量值中发现的由标准偏差导致的某些误差。除非另有说明，本文所有百分数、比率和比例以重量计，尤其是除非另有具体说明，所述组合物中各组分比例以相对于这些组分混合物总质量的百分数给出。
还是在本文中，以端点描述的数值范围包括包含在该范围内的所有数值(例如1-5包括1、1.5、2、2.75、3、3.80、4、5等)。
还是在本文中，“a”、“an”、“the”、“至少一种”和“一种或多种”可互换使用。
还是在本文中，术语“包含”及其变型在这些术语出现在说明书和权利要求书中时不具有限制含义。
在整个申请和权利要求书中公开的术语“例如”、“非限制性地”等以及示例性化合物、范围、参数等意欲以非限制性方式表示本发明实施方案。其他化合物、范围、参数等可由本领域熟练技术人员在不背离本发明精神和范围下使用。
本发明包括至少部分地用本发明涂料组合物涂覆的基材以及涂覆所述基材的方法。本文所用术语“基材”非限制性地包括罐、金属罐、包装材料、容器、贮器或其用于支撑、触碰或接触任何类型食品或饮料的任何部分。术语“基材”、“食品罐”、“食品容器”等对于非限制性实例还包括“罐底”，其可由罐底原料冲压并用于食品和饮料包装材料中。
本发明包括通过使环氧化植物油与羟基官能材料在酸催化剂存在下反应制备羟基官能油多元醇和含有羟基官能油多元醇的涂料组合物的方法。所述羟基官能油多元醇尤其可以用于制备包装材料用涂料。在本发明某些实施方案中，用交联剂交联所述羟基官能油多元醇以形成食品和饮料包装材料和容器用涂料组合物。
环氧化植物油可以单独或与其他环氧化植物油组合使用。环氧化植物油可以由植物油对于非限制性实例通过在植物油中加入过氧化氢和甲酸或乙酸，然后使混合物保持在升高温度下直到部分或全部碳-碳双键转化成环氧基而制备。
植物油主要含有甘油酯，其为甘油和各种不饱和程度的脂肪酸的三酯。对于非限制性实例，本发明中所用环氧化植物油可以由植物油(脂肪酸甘油三酯)制备，例如非限制性地为甘油和具有约12-约24个碳原子的烷基链的脂肪酸的酯。在不饱和甘油酯油中作为甘油三酯的脂肪酸甘油酯通常是指干性油或半干性油。干性油对于非限制性实例包括亚麻子油、紫苏子油及其组合，而半干性油非限制性地包括松浆油、大豆油、红花油及其组合。在某些实施方案中，甘油三酯油具有相同脂肪酸链或具有连接于相同甘油分子上的不同脂肪酸链。在某些实施方案中，所述油具有含非共轭双键的脂肪酸链。在某些实施方案中，单个双键或共轭双键脂肪酸链以少量使用。甘油酯中双键不饱和度可通过碘值(数)测量，碘值(数)表示脂肪酸链中双键不饱和程度。在本发明某些实施方案中所用不饱和脂肪酸甘油酯油具有大于约25或约100-约210的碘值。
本发明所用天然存在植物油对于非限制性实例可为作为甘油酯存在的脂肪酸链的混合物并且非限制性地包括甘油酯脂肪酸酯分布，其中脂肪酸分布可以是无规的，但在所给范围内可以取决于植物来源生长条件而适当改变。在某些实施方案中使用大豆油，其大致包含约11％棕榈酸、约4％硬脂酸、约25％油酸、约51％亚麻酸和约9％亚油酸脂肪酸，其中油酸、亚油酸和亚麻酸为不饱和脂肪酸。在本发明某些实施方案中所用不饱和植物油非限制性地包括甘油酯油，其含有非共轭不饱和脂肪酸甘油酯酯如非限制性地为亚油酸和亚麻酸脂肪酸。
不饱和甘油酯油非限制性地包括玉米油、棉籽油、葡萄籽油、大麻籽油、亚麻子油、芥子油(wild mustard oil)、花生油、紫苏子油、罂粟籽油、菜籽油、红花油、麻油、大豆油、向日葵子油、低芥酸菜子油、松浆油及其混合物。本发明所用脂肪酸甘油酯对于非限制性实例包括含有亚油酸和亚麻酸脂肪酸链的那些，油如非限制性地为大麻籽油、亚麻子油、紫苏子油、罂粟籽油、红花油、大豆油、向日葵子油、低芥酸菜子油、松浆油、葡萄籽油、rattonseed oil、玉米油以及含有高水平亚油酸和亚麻酸脂肪酸甘油酯的类似油。在某些实施方案中，甘油酯可以含有较少量饱和脂肪酸。对于非限制性实例，可以使用主要含有亚油酸和亚麻酸脂肪酸甘油酯的大豆油。在本发明某些实施方案中使用该类油组合。植物油可以通过已知方法完全或部分氧化，例如对于非限制性实例使用酸如非限制性地为为用于环氧化不饱和植物油的不饱和双键的过氧酸。在某些实施方案中所用不饱和甘油酯油包括甘油单酯、甘油二酯及其与甘油三酯或饱和及不饱和脂肪酸的脂肪酸酯的混合物。
在某些实施方案中，环氧化植物油包括玉米油、棉籽油、葡萄籽油、大麻籽油、亚麻子油、芥子油、花生油、紫苏子油、罂粟籽油、菜籽油、红花油、麻油、大豆油、向日葵子油、低芥酸菜子油、松浆油、脂肪酸酯、该类油的甘油单酯或甘油二酯，或其混合物。
在本发明某些实施方案中使用市售来源的环氧化植物油，例如对于非限制性实例为以来自Arkema，Inc的商标名“VIKOLOX”和“VIKOFLEX7170”、来自Chemtura Corporation的商标名“DRAPEX 6.8”和来自FerroCorp的商标名“PLAS-CHECK 775”出售的环氧化大豆油。本发明所用其他环氧化植物油对于非限制性实例包括以来自Arkema，Inc.的商标名“VIKOFLEX 7190”和来自Chemtura Corporation的商标名“DRAPEX10.4”出售的环氧化亚麻子油，环氧化棉籽油，环氧化红花油及其混合物。在某些实施方案中使用环氧化大豆油。
在本发明某些实施方案中，羟基官能材料非限制性地包括丙二醇、乙二醇、1，3-丙二醇、新戊二醇、三羟甲基丙烷、二甘醇、聚乙二醇、聚酯、聚碳酸酯、聚烯烃、羟基官能聚烯烃及其混合物。在某些实施方案中，羟基官能材料包括醇如非限制性地为正丁醇、2-乙基己醇、苄醇等，单独或与二醇或多元醇组合。
在某些实施方案中，羟基官能材料以约2∶98-约98∶2或约5∶95-约40∶60的羟基官能材料与环氧化植物油重量比存在。在某些实施方案中，羟基官能材料的羟基官能度与环氧化植物油的环氧官能度的当量比为约0.1∶1-约3∶1。在某些实施方案中，羟基官能度与环氧化植物油的环氧官能度的当量比为约0.2∶1-约3∶1。在某些实施方案中，羟基官能度与环氧化植物油的环氧官能度的当量比为约0.2∶1。
在本发明某些实施方案中，用于促进环氧化植物油与羟基官能材料反应的酸催化剂可以为强酸催化剂，例如对于非限制性实例为一种或多种磺酸或另一强酸(pKa约为3或更小的酸)，三氟甲磺酸，元素周期表(根据IUPAC 1970公约)的第IIA、IIB、IIIA、IIIB或VIIIA族金属的三氟甲磺酸盐，所述三氟甲磺酸盐的混合物，或其组合。在某些实施方案中，酸催化剂的量基于反应混合物总重量可以为约1-约10,000ppm或约10-约1,000ppm。对于非限制性实例，催化剂包括第IIA族金属三氟甲磺酸盐催化剂如非限制性地为三氟甲磺酸镁、第IIB族金属三氟甲磺酸盐催化剂如非限制性地为三氟甲磺酸锌和镉、第IIIA族金属三氟甲磺酸盐催化剂如非限制性地为三氟甲磺酸镧、第IIIB族金属三氟甲磺酸盐催化剂如非限制性地为三氟甲磺酸铝和第VIIIA族金属三氟甲磺酸盐催化剂如非限制性地为三氟甲磺酸钴及其组合。金属三氟甲磺酸盐催化剂的量基于反应混合物总重量对于非限制性实例可以为约10-约1,000ppm或约10-约200ppm。本发明某些实施方案使用呈在有机溶剂中溶液形式的金属三氟甲磺酸盐催化剂。溶剂的实例非限制性地包括水，醇如正丁醇、乙醇、丙醇等以及芳烃溶剂，脂环族极性溶剂如对于非限制性实例为脂环族酮(例如环己酮)，极性脂族溶剂如对于非限制性实例为烷氧基链烷醇、2-甲氧基乙醇，非羟基官能溶剂，及其混合物。
在某些实施方案中，将环氧化植物油和羟基官能材料在酸催化剂存在下加热到约50-约200℃的温度。在环氧化植物油和羟基官能材料合成中可任选包括溶剂以有助于控制粘度。在某些实施方案中，溶剂对于非限制性实例包括酮如非限制性地为甲基戊基酮，芳族溶剂如非限制性地为二甲苯或Aromatic 100，酯类溶剂或其他非羟基官能溶剂，及其混合物。在本发明各实施方案中使用基于反应混合物总重量为约0-约90％或约5-约30％的溶剂。在某些实施方案中，在约2-约3小时之后，消耗＞90％的环氧基。选自上述那些的溶剂以及非限制性地包括羟基官能溶剂的其他溶剂可在冷却时加入。在某些实施方案中，理想的是具有约30-约80的最终NV(不挥发物含量，以重量计)。
在某些实施方案中，羟基官能油多元醇与交联剂混合以形成可固化涂料组合物。在某些实施方案中，混合物进一步包括羟基官能丙烯酸类共聚物、酸官能丙烯酸类共聚物、缩水甘油基官能丙烯酸类共聚物、丙烯酰胺官能丙烯酸类共聚物或其混合物。本发明所用交联剂的非限制性实例包括苯胍胺、苯胍胺-甲醛、甘脲、三聚氰胺-甲醛、酚类交联剂、苯酚甲醛、脲甲醛、异氰酸酯、封端异氰酸酯及其混合物。在各实施方案中，交联剂与羟基官能油多元醇之比为约1∶99-约90∶10或约5∶95-约60∶40。在羟基官能油多元醇和交联剂的混合物中任选可以加入固化催化剂以增强固化。固化催化剂对于非限制性实例包括十二烷基苯磺酸、对甲苯磺酸等及其混合物。在某些实施方案中，其他聚合物如非限制性地为聚醚、聚酯、聚碳酸酯、聚氨酯等及其混合物可以混入涂料组合物中。在某些实施方案中，包装材料用涂料的固化条件在约500-约600°F下为约10-约60秒或在约250-约500°F下为约1-约20分钟。在某些实施方案中，使用配制热固化涂料常用的添加剂如非限制性地为溶剂和滑移助剂(slip aids)。
本发明羟基官能油多元醇和涂料组合物可以包括本领域熟练技术人员已知的常规添加剂，例如非限制性地为流动剂、表面活性剂、消泡剂、防堵孔添加剂、润滑剂、热量释放添加剂和固化催化剂。
羟基官能油多元醇可用于形成可热固化涂料组合物。认为羟基官能油多元醇的羟基官能团可与常规交联剂如三聚氰胺和酚类材料反应。还为(甲基)丙烯酸酯官能的羟基官能化合物不为制备热固化用羟基官能油多元醇的优选材料。
在本发明某些实施方案中，将一种或多种涂料组合物施加至基材，例如对于非限制性实例为罐、金属罐、包装材料、容器、贮器、罐底或其用于支撑或触碰任何类型食品或饮料的任何部分。在某些实施方案中，施加除本发明涂料组合物外的一种或多种涂料，例如对于非限制性实例可以在基材和涂料组合物之间施加底漆。
可以本领域熟练技术人员已知的任何方式将涂料组合物施加至基材。在某些实施方案中，将涂料组合物喷涂或辊涂至基材上。
对于某些应用，溶剂基聚合物溶液对于非限制性实例可以含有约20-约60重量％的聚合物固体。在某些实施方案中利用有机溶剂以促进辊涂或其他施加方法并且该类溶剂可以非限制性地包括正丁醇、2-丁氧基乙醇、二甲苯和其他芳族溶剂和酯类溶剂及其混合物。在某些实施方案中，正丁醇与2-丁氧基乙醇组合使用。在某些实施方案中，本发明涂料组合物可以用已知颜料和遮光剂着色和/或遮盖。对于许多应用，对于非限制性实例包括食品应用，颜料可以为氧化锌、炭黑或二氧化钛。在某些实施方案中，所得涂料组合物通过涂料工业中已知的常规方法施加。因此，对于非限制性实例，喷涂、辊涂、浸涂和流涂施加方法可用于透明和着色膜。在某些实施方案中，在施加至基材上之后，涂料组合物在约130-约250℃或更高的温度下热固化足够长时间以进行完全固化以及使任何挥发性组分挥发。
实施例
本发明将进一步参照以下非限制性实施例描述。应理解这些实施例的变型和改变可由本领域熟练技术人员在不背离本发明精神和范围下做出。
实施例1
制备羟基官能油多元醇
在氮气下搅拌11.0克丙二醇、112.0克环氧化大豆油、30.9克甲基戊基酮和0.036克Nacure A-218(可由King Industries获得)并加热至150℃。在＜155℃下控制初始放热并使混合物在150℃下保持约2小时，然后冷却。环氧乙烷滴定表明环氧基转化率＞99.9％。
实施例2
制备羟基官能油多元醇
将50.9克二甘醇和150克环氧化大豆油加入1升烧瓶中。在20℃下将0.02克Nacure A-218(可由King Industries获得)加入烧瓶中，在氮气下搅拌混合物并加热到160℃。在＜165℃下控制初始放热并使混合物在160℃下保持约3小时。环氧乙烷滴定表明环氧基转化率＞99.9％。在冷却下加入50.3克乙二醇二丁醚而得到80％NV。
实施例3
制备羟基官能油多元醇
将50.0克新戊二醇和150克环氧化大豆油加入1升烧瓶中。在20℃下将0.02克Nacure A-218(可由King Industries获得)加入烧瓶中，在氮气下搅拌混合物并加热到160℃。在＜165℃下控制初始放热并使混合物在160℃下保持约3小时。环氧乙烷滴定表明环氧基转化率＞99.9％。在冷却下加入50.3克乙二醇二丁醚而得到80％NV。
实施例4A
制备羟基官能油多元醇
在氮气下搅拌185.500克丙二醇、812.450克环氧化大豆油和0.206克Nacure A-218(可由King Industries获得)并加热到150℃(141克丙二醇作为未反应溶剂残留)。在＜155℃下控制初始放热并使混合物在150℃下保持约2小时，然后冷却。环氧乙烷滴定表明环氧基转化率＞99.9％。
实施例5
制备羟基官能油多元醇
将150.0克环氧化大豆油、36.8克三羟甲基丙烷和46.7克甲基戊基酮加入1升烧瓶中。在20℃下将0.02克Nacure A218(可由King Industries获得)加入烧瓶中，在氮气下搅拌混合物并加热到150℃。初始放热控制为153℃并使混合物在150℃下保持约3小时，然后冷却。环氧乙烷滴定表明环氧基转化率＞99.9％。
实施例6
制备缩水甘油基官能丙烯酸类共聚物
将1253克乙二醇二丁醚装入5升玻璃烧瓶中并在氮气下加热和搅拌到110℃。在3小时内加入450克甲基丙烯酸缩水甘油酯、525克丙烯酸丁酯、525克甲基丙烯酸甲酯和75克过辛酸叔丁酯的混合物，同时使烧瓶内容物保持在110℃下。然后在烧瓶中加入额外197克乙二醇二丁醚，同时使温度降至95℃。然后在30分钟内加入150克乙二醇二丁醚和25克过辛酸叔丁酯的混合物。然后使烧瓶在95℃下保持60分钟，随后冷却。
实施例7
制备涂料组合物
制备共混物，其由76.14磅实施例5的树脂，57.9磅实施例6的树脂，85.7磅RSO199-可由Cytec Industries获得的酚醛树脂，17.04磅Santolink EP560-可由Cytec Industries获得的酚醛树脂，10.7磅Cymel27-809-可由Cytec Industries获得的苯胍胺树脂，6.06磅Lanco GliddTPG 087-可由Lubrizol Advanced Materials获得的巴西棕榈蜡在溶剂中分散体，4.6磅由30份MPP-620XF-可由Micro Powders，Inc获得的聚乙烯蜡在70份乙二醇二丁醚中组成的分散体，0.387磅Coroc A-620-A2-可由Cook Composites and Polymers获得的丙烯酸流动剂和16.4磅乙二醇二丁醚组成。

Claims (21)

1.一种包含通过包括使环氧化植物油与羟基官能材料在酸催化剂存在下反应的方法制备的羟基官能油多元醇的涂料组合物。
2.根据权利要求1的涂料组合物，其中所述环氧化植物油包括玉米油、棉籽油、葡萄籽油、大麻籽油、亚麻子油、芥子油、花生油、紫苏子油、罂粟籽油、菜籽油、红花油、麻油、大豆油、向日葵子油、低芥酸菜子油、松浆油、脂肪酸酯、该类油的甘油单酯或甘油二酯，或其混合物。
3.根据权利要求1的涂料组合物，其中所述环氧化植物油衍生自不饱和脂肪酸甘油酯。
4.根据权利要求1的涂料组合物，其中所述环氧化植物油基于所述羟基官能油多元醇总重量以约2-约98份的量存在。
5.根据权利要求1的涂料组合物，其中所述羟基官能材料包括丙二醇、1，3-丙二醇、乙二醇、新戊二醇、三羟甲基丙烷、二甘醇、聚乙二醇、苄醇、2-乙基己醇、聚酯、聚碳酸酯、羟基官能聚烯烃或其混合物。
6.根据权利要求1的涂料组合物，其中所述羟基官能材料的羟基官能度与所述环氧化植物油的环氧官能度的当量比为约0.2∶1-约3∶1。
7.根据权利要求1的涂料组合物，其中所述酸催化剂包括强酸如磺酸，三氟甲磺酸，元素周期表(根据IUPAC 1970公约)的第IIA、IIB、IIIA、IIIB或VIIIA族金属的三氟甲磺酸盐，所述三氟甲磺酸盐的混合物，或其组合。
8.根据权利要求1的涂料组合物，其中所述环氧化植物油与所述羟基官能材料的反应在溶剂存在下进行。
9.根据权利要求8的涂料组合物，其中所述溶剂包括酮、芳族溶剂、酯类溶剂、非羟基官能溶剂或其混合物。
10.根据权利要求1的涂料组合物，其中使根据权利要求1的羟基官能油多元醇与交联剂反应以形成涂料组合物。
11.根据权利要求10的涂料组合物，其中所述交联剂包括苯酚甲醛、三聚氰胺-甲醛、脲甲醛、苯胍胺-甲醛、封端异氰酸酯或其混合物。
12.根据权利要求11的涂料组合物，进一步包含羟基官能丙烯酸类共聚物、酸官能丙烯酸类共聚物、缩水甘油基官能丙烯酸类共聚物、丙烯酰胺官能丙烯酸类共聚物或其混合物。
13.一种通过包括使环氧化植物油与羟基官能材料在酸催化剂存在下反应以形成羟基官能油多元醇和用交联剂交联所述羟基官能油多元醇以形成涂料组合物的方法而制备的涂料组合物。
14.一种涂覆基材的方法，包括以下步骤：
a)通过包括使环氧化植物油与羟基官能材料在酸催化剂存在下反应以形成羟基官能油多元醇的方法制备涂料组合物；
b)将所述羟基官能油多元醇与交联剂混合以形成混合物；
c)将所述混合物施加至基材；和
d)交联所述混合物。
15.用根据权利要求1的涂料组合物涂覆的基材。
16.一种包含通过包括使环氧化植物油与羟基官能材料在酸催化剂存在下反应以形成羟基官能油多元醇的方法制备的羟基官能油多元醇的涂料组合物，其中所述羟基官能材料的羟基官能度与所述环氧化植物油的环氧官能度的当量比为约0.2∶1-约3∶1。
17.根据权利要求16的羟基官能油多元醇，其中所述羟基官能材料包括丙二醇、1，3-丙二醇、乙二醇、新戊二醇、三羟甲基丙烷、二甘醇、聚乙二醇、苄醇、2-乙基己醇、聚酯、聚碳酸酯、羟基官能聚烯烃或其混合物。
18.根据权利要求16的羟基官能油多元醇，其中所述酸催化剂包括强酸如磺酸，三氟甲磺酸，元素周期表(根据IUPAC 1970公约)的第IIA、IIB、IIIA、IIIB或VIIIA族金属的三氟甲磺酸盐，所述三氟甲磺酸盐的混合物，或其组合。
19.一种通过用交联剂交联根据权利要求16的羟基官能油多元醇以形成涂料组合物而制备的涂料组合物。
20.一种涂覆基材的方法，包括以下步骤：
a)通过包括使环氧化植物油与羟基官能材料在酸催化剂存在下反应以形成羟基官能油多元醇的方法制备涂料组合物，其中羟基官能度与所述环氧化植物油的环氧官能度的当量比为约0.2∶1-约3∶1；
b)将所述羟基官能油多元醇与交联剂混合以形成混合物；
c)将所述混合物施加至基材；和
d)交联所述混合物。
21.用根据权利要求20的涂料组合物涂覆的基材。
CN201080009689.4A 2009-03-05 2010-03-02 羟基官能油多元醇和由羟基官能油多元醇制备的涂料组合物 Expired - Fee Related CN102333833B (zh)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US15773209P 2009-03-05 2009-03-05
US61/157,732 2009-03-05
EP09160286 2009-05-14
EP09160286.2 2009-05-14
PCT/EP2010/052577 WO2010100122A1 (en) 2009-03-05 2010-03-02 Hydroxyl functional oil polyols and coating compositions prepared from hydroxyl functional oil polyols

Publications (2)

Publication Number Publication Date
CN102333833A true CN102333833A (zh) 2012-01-25
CN102333833B CN102333833B (zh) 2015-01-21

Family

ID=40885936

Family Applications (2)

Application Number Title Priority Date Filing Date
CN201080009688.XA Expired - Fee Related CN102333801B (zh) 2009-03-05 2010-03-02 羟基官能油多元醇丙烯酸类接枝共聚物
CN201080009689.4A Expired - Fee Related CN102333833B (zh) 2009-03-05 2010-03-02 羟基官能油多元醇和由羟基官能油多元醇制备的涂料组合物

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CN201080009688.XA Expired - Fee Related CN102333801B (zh) 2009-03-05 2010-03-02 羟基官能油多元醇丙烯酸类接枝共聚物

Country Status (13)

Country Link
US (2) US20120022186A1 (zh)
EP (2) EP2403885B1 (zh)
KR (2) KR20110132336A (zh)
CN (2) CN102333801B (zh)
AU (2) AU2010220406C1 (zh)
CA (2) CA2753864A1 (zh)
ES (1) ES2693159T3 (zh)
HK (2) HK1162189A1 (zh)
MX (2) MX2011009154A (zh)
MY (1) MY173945A (zh)
RU (2) RU2543878C2 (zh)
WO (2) WO2010100122A1 (zh)
ZA (2) ZA201105580B (zh)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105008470A (zh) * 2013-03-12 2015-10-28 阿克佐诺贝尔国际涂料股份有限公司 用于制备可辐射固化低聚物的协同增效催化剂组合

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9394456B2 (en) 2009-02-24 2016-07-19 Akzo Nobel Coatings International B.V. Latex emulsions and coating compositions formed from latex emulsions
WO2010097353A1 (en) 2009-02-24 2010-09-02 Akzo Nobel Coatings International B.V. Latex emulsions and coating compositions formed from latex emulsions
MX2011009154A (es) 2009-03-05 2011-10-10 Akzo Nobel Coatings Int Bv Polioles de aceite con funcion de hidroxilo y composiciones de recubrimiento preparadas de polioles de aceite con funcion de hidroxilo.
WO2012089746A1 (en) * 2010-12-28 2012-07-05 Akzo Nobel Coatings International B.V. High acid large particle size latex emulsions, enhanced stabilization of high acid large particle size latex emulsions, and coating compositions formed therefrom
KR101949209B1 (ko) 2010-12-29 2019-04-22 아크조노벨코팅스인터내셔널비.브이. 접착 촉진제 수지 조성물 및 상기 접착 촉진제 수지 조성물을 포함하는 코팅 조성물
IN2014CN04275A (zh) * 2011-12-21 2015-07-31 Akzo Nobel Chemicals Int Bv
RU2605418C2 (ru) * 2011-12-21 2016-12-20 Акцо Нобель Коатингс Интернэшнл Б.В. Покрывные композиции на основе растворителей
KR102025208B1 (ko) * 2011-12-21 2019-09-25 아크조노벨코팅스인터내셔널비.브이. 수성 코팅 조성물
US20140329954A1 (en) * 2011-12-28 2014-11-06 Akzo Nobel Coatings International B.V. Acetoacetate Functional Latex Emulsions Cured With Phenolic Resins and Coating Compositions Formed Therefrom
JP2014122323A (ja) 2012-10-31 2014-07-03 Dow Global Technologies Llc 金属包装のためのポリカーボネートコーティング
KR20150083853A (ko) 2012-11-08 2015-07-20 바스프 에스이 경화성 에폭시 수지로서의 2-페닐-1,3-프로판디올의 디글리시딜 에테르 유도체 및 그의 올리고머
US9150685B2 (en) 2012-11-08 2015-10-06 Basf Se Diglycidyl ethers of 2-phenyl-1,3-propanediol derivatives and oligomers thereof as curable epoxy resins
JP2016516110A (ja) 2013-03-15 2016-06-02 アクゾ ノーベル コーティングス インターナショナル ビー ヴィ フェノールステアリン酸をベースとするビスフェノールａフリーのポリエーテル樹脂、およびそれから形成される塗料組成物
CN105283477A (zh) * 2013-03-15 2016-01-27 阿克佐诺贝尔国际涂料股份有限公司 基于苯酚硬脂酸的丙烯酸系接枝聚醚树脂和由其形成的涂料组合物
WO2014188438A1 (en) 2013-05-21 2014-11-27 Asian Paints Ltd. Castor oil derived hydroxy functional acrylic copolymers for surface coating applications
KR102182319B1 (ko) * 2013-06-05 2020-11-25 삼성전자주식회사 전자 기기 및 전자 기기에서 배터리 정보 제공 방법
CN103396342A (zh) * 2013-08-08 2013-11-20 江苏卡特新能源有限公司 基于环氧大豆油改性的多官能度丙烯酸酯光聚合单体制备
US9695139B2 (en) 2013-08-14 2017-07-04 Basf Se Glycidyl ethers of limonene derivatives and oligomers thereof as curable epoxy resins
US11981822B2 (en) 2014-12-24 2024-05-14 Swimc Llc Crosslinked coating compositions for packaging articles such as food and beverage containers
CN107109100B (zh) 2014-12-24 2020-08-25 宣伟投资管理有限公司 用于包装制品例如食品和饮料容器的涂料组合物
US11059989B2 (en) 2017-06-30 2021-07-13 Valspar Sourcing, Inc. Crosslinked coating compositions for packaging articles such as food and beverage containers
CN107109104B (zh) 2014-12-24 2021-01-26 宣伟投资管理有限公司 用于包装制品例如食品和饮料容器的不含苯乙烯的涂料组合物
KR101631606B1 (ko) * 2015-03-20 2016-06-17 동구산업(주) 에폭시화된 식물성 오일로부터 바이오폴리올의 제조방법
WO2016193032A1 (en) 2015-06-02 2016-12-08 Basf Se Diglycidyl ethers of tetrahydrofuran diglycol derivatives and oligomers thereof as curable epoxy resins
CA2993870C (en) 2015-07-31 2023-09-12 The Governors Of The University Of Alberta Synthesis of polyols suitable for castor oil replacement
MY189019A (en) 2016-06-28 2022-01-19 Ptt Global Chemical Public Co Ltd Hybrid polyols based on natural oil polyols
US10703920B2 (en) 2016-09-28 2020-07-07 Ppg Industries Ohio, Inc. Corrosion-resistant epoxidized vegetable oil can interior coating
EP3660067A1 (en) * 2018-11-30 2020-06-03 Henkel AG & Co. KGaA Adhesive composition for flexible lamination
WO2021024033A1 (en) 2019-08-08 2021-02-11 Aditya Birla Chemicals (Thailand) Ltd. (Epoxy Division) A modified epoxy resin
CZ2021507A3 (cs) 2021-11-04 2023-05-17 Synpo, A.S. Epoxy resins
CN115894774A (zh) * 2022-12-16 2023-04-04 嘉宝莉化工集团股份有限公司 一种生物基羟基聚丙烯酸酯乳液及其制备方法和应用

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006012344A1 (en) * 2004-06-25 2006-02-02 Pittsburg State University Modified vegetable oil-based polyols
WO2007127379A1 (en) * 2006-04-27 2007-11-08 Pittsburg State University Enhanced oligomeric polyols and polymers made therefrom
WO2008151286A1 (en) * 2007-06-05 2008-12-11 The Glidden Company Radiation curable coating composition derived from epoxidized vegetable oils

Family Cites Families (119)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE581943A (zh) 1958-08-25
US3248356A (en) 1963-09-26 1966-04-26 Dow Chemical Co Multisperse acrylic latexes
GB1100569A (en) 1966-02-08 1968-01-24 Dow Chemical Co A process for preparing acrylic latexes
US3424766A (en) * 1966-08-03 1969-01-28 Celanese Coatings Co Epoxidized urethane oils
US3647520A (en) 1970-07-06 1972-03-07 Continental Can Co Electron beam cross-linking of coating compositions containing ethylene unsaturated carboxylic acid copolymers and a melamine composition
US3699061A (en) * 1971-02-22 1972-10-17 Sherwin Williams Co Coating composition containing urethan-modified epoxidized ester and polycarboxylic acid material
US3827993A (en) 1972-06-14 1974-08-06 Sherwin Williams Co Liquid polyol compositions
US3912670A (en) 1973-02-28 1975-10-14 O Brien Corp Radiation curable can coating composition
US4025548A (en) 1974-02-04 1977-05-24 The O'brien Corporation Radiation curable oligomers
US4264483A (en) 1974-08-23 1981-04-28 Whittaker Corporation Decorating ink
JPS5921909B2 (ja) 1974-10-31 1984-05-23 東レ株式会社 放射線硬化性塗料組成物
GB1546726A (en) 1975-06-20 1979-05-31 Toyo Ink Mfg Co Coatings on interior surfaces of metallic cans and on surfaces of metallics sheet material for cans
US4212781A (en) 1977-04-18 1980-07-15 Scm Corporation Modified epoxy resins, processes for making and using same and substrates coated therewith
CA1113643A (en) 1976-12-23 1981-12-01 The Dow Chemical Company Method of water-solubilizing high performance polyether epoxide resins, the solubilized resins and thermoset, hydrophobic coatings derived therefrom
JPS55120613A (en) 1979-03-13 1980-09-17 Hitachi Chem Co Ltd Production of acrylic emulsion polymer
GB2052526B (en) 1979-06-13 1983-03-16 Nippon Soda Co Paints for cathodic electro deposition
CA1143080A (en) 1979-11-19 1983-03-15 Bertram Zuckert Process for producing improved aqueous emulsions of air drying and stoving alkyd resins
US4425450A (en) 1980-10-23 1984-01-10 Ford Motor Company Paint composition comprising hydroxy functional film former and improved stable flow control additive
US4377457A (en) 1980-11-21 1983-03-22 Freeman Chemical Corporation Dual cure coating compositions
AT369774B (de) 1981-06-12 1983-01-25 Vianova Kunstharz Ag Verfahren zur herstellung von waessrigen alkydharzemulsionen fuer lufttrocknende lacke
JPS5821411A (ja) 1981-07-29 1983-02-08 Hitachi Chem Co Ltd 被覆用樹脂組成物
JPS58185604A (ja) 1982-04-26 1983-10-29 Tokuyama Soda Co Ltd ポリメタクリル酸グリシジルラテツクスの製造方法
NZ205206A (en) 1982-08-12 1986-07-11 Scm Corp Water-dispersed coating compositions containing alkylol acrylamide-containing copolymers
FR2536069A1 (fr) 1982-11-17 1984-05-18 Bp Chimie Sa Procede de preparation de produits d'addition d'epoxydes et de composes hydroxyles
DE3246612A1 (de) 1982-12-16 1984-06-20 Henkel KGaA, 4000 Düsseldorf Verfahren zur herstellung modifizierter triglyceride mit im mittel epoxid- und hydroxyl- sowie ethergruppen
JPS6047074A (ja) 1983-08-25 1985-03-14 Dai Ichi Kogyo Seiyaku Co Ltd 防食塗料組成物
US4707535A (en) 1983-10-27 1987-11-17 Union Carbide Corporation Low viscosity adducts of a poly(active hydrogen) organic compound and polyepoxide
FR2554112B1 (fr) 1983-10-28 1986-05-16 Charbonnages Ste Chimique Procede de reticulation de polymeres d'ethylene contenant des fonctions anhydride, compositions polymeres reticulables et application de ces compositions a l'enduction de substrats
JPS60156707A (ja) 1984-01-26 1985-08-16 Hitachi Chem Co Ltd 水性樹脂の製造法
JPS60156708A (ja) 1984-01-26 1985-08-16 Hitachi Chem Co Ltd ビニル変性アルキド樹脂の製造法
JPS63112670A (ja) 1986-10-29 1988-05-17 Kansai Paint Co Ltd 水性被覆用組成物
US4829124A (en) 1986-11-17 1989-05-09 Armstrong World Industries, Inc. Dynamically crosslinked thermoplastic elastomer
CA1296821C (en) 1986-11-17 1992-03-03 Lawrence Clark Dynamically crosslinked thermoplastic elastomer
EP0329027A3 (en) 1988-02-18 1990-10-10 BASF Aktiengesellschaft Epoxide crosslinkable latices
GB8811939D0 (en) 1988-05-20 1988-06-22 Wasson E A Coating process
US4959271A (en) * 1988-07-06 1990-09-25 The Dow Chemical Company Multilayer sheet
JPH0292916A (ja) 1988-09-30 1990-04-03 Kansai Paint Co Ltd 樹脂組成物及び缶用塗料組成物
JPH02232219A (ja) 1989-03-07 1990-09-14 Dainippon Ink & Chem Inc 水性被覆用樹脂組成物
JP2773915B2 (ja) 1989-09-04 1998-07-09 関西ペイント株式会社 缶内面用水性被覆組成物
DE3931623A1 (de) 1989-09-22 1991-04-04 Lechner Gmbh Verfahren zum herstellen eines behaelters
US5043380A (en) 1990-10-29 1991-08-27 The Dexter Corporation Metal container coating compositions comprising an acrylic polymer latex, melamine formaldehyde resin and an phenol formaldehyde resin
GB9027406D0 (en) 1990-12-18 1991-02-06 Ciba Geigy Ag Production of compounds
DE4115146A1 (de) 1991-05-08 1992-11-12 Henkel Kgaa Verfahren zur herstellung von epoxid-ringoeffnungsprodukten mit einem definierten rest-epoxidsauerstoffgehalt
US5318808A (en) 1992-09-25 1994-06-07 Polyset Company, Inc. UV-curable coatings
WO1994012554A1 (en) 1992-11-24 1994-06-09 Minnesota Mining And Manufacturing Company Radiation curable oligomers and magnetic recording media prepared therefrom
US5714539A (en) 1993-10-04 1998-02-03 Ppg Industries, Inc. Polymeric surfactant and latex made therefrom
CA2177174A1 (en) 1993-12-21 1995-06-29 Zeng K. Liao Process to react epoxide-containing compounds and aliphatic alcohols
DE4446877A1 (de) 1994-12-27 1996-07-04 Henkel Kgaa Verfahren zur Ringöffnung von Epoxiden
DE19533168A1 (de) 1995-09-08 1997-03-13 Henkel Kgaa Fettchemische Polyole als Reaktivverdünner
GB2305919B (en) 1995-10-02 1999-12-08 Kansai Paint Co Ltd Ultraviolet-curing coating composition for cans
JPH09183940A (ja) 1995-12-28 1997-07-15 Nippon Paint Co Ltd 水性被覆組成物、製造方法及び被膜
US5733970A (en) 1997-01-28 1998-03-31 The Glidden Company Aqueous dispersed, epoxy crosslinked maleated oil microgel polymers for protective coatings
US5968605A (en) 1997-02-27 1999-10-19 Acushnet Company Electron beam radiation curable inks for game balls, golf balls and the like
US6197878B1 (en) 1997-08-28 2001-03-06 Eastman Chemical Company Diol latex compositions and modified condensation polymers
JP3879203B2 (ja) 1997-11-04 2007-02-07 東洋インキ製造株式会社 活性エネルギー線硬化性化合物、オリゴマー、ならびに塗料組成物
US6156816A (en) 1998-08-20 2000-12-05 Henkel Corporation Screen coating composition and method for applying same
US6225389B1 (en) 1998-08-20 2001-05-01 Henkel Corp. Screen coating composition and method for applying same
US6686335B1 (en) * 1998-09-22 2004-02-03 Cephalon, Inc. Hydroxamate-containing cysteine and serine protease inhibitors
US6433121B1 (en) * 1998-11-06 2002-08-13 Pittsburg State University Method of making natural oil-based polyols and polyurethanes therefrom
US6107433A (en) 1998-11-06 2000-08-22 Pittsburg State University Process for the preparation of vegetable oil-based polyols and electroninsulating casting compounds created from vegetable oil-based polyols
ATE234876T1 (de) * 1998-12-24 2003-04-15 Akzo Nobel Nv Wässrige beschichtungszusammensetzung und ein polyol für eine solche zusammensetzung
US6399672B1 (en) 1999-06-02 2002-06-04 Sartomer Technologies Co., Inc. Oil soluble metal-containing compounds, compositions and methods
AU7620800A (en) 1999-09-30 2001-04-30 Dow Chemical Company, The Heat stable article, latex composition, and method of making
DE19960693A1 (de) 1999-12-16 2001-07-19 Dupont Performance Coatings Verfahren zur anodischen Elektrotauchlackierung, sowie Elektrotauchlacke
WO2001059020A1 (en) * 2000-02-08 2001-08-16 The C.P. Hall Company Low voc, nonlinear polyester polyol resin-based compositions
DE10048849A1 (de) 2000-10-02 2002-04-18 Basf Coatings Ag Verfahren zur Herstellung eines thermisch und mit aktinischer Strahlung härtbaren Mehrkomponentensystems und seine Verwendung
CN1215115C (zh) 2001-01-15 2005-08-17 尤尼吉可株式会社 聚烯烃树脂水性分散体
US20020151626A1 (en) 2001-02-08 2002-10-17 Hisashi Isaka Curing composition
US6844390B2 (en) 2001-04-09 2005-01-18 Eastman Chemical Company Modified alkyd compositions comprising polyol latex compositions and processes of making them
US6974665B2 (en) 2001-09-06 2005-12-13 University Of Nebraska In situ screening to optimize variables in organic reactions
US6916874B2 (en) 2001-09-06 2005-07-12 Valspar Sourcing, Inc. Coating compositions having epoxy functional stabilizer
CA2482470C (en) * 2002-04-19 2011-06-07 Ciba Specialty Chemicals Holding Inc. Curing of coatings induced by plasma
US20030225149A1 (en) 2002-04-30 2003-12-04 Blazecka Peter G. Process for preparing highly functionalized gamma-butyrolactams and gamma-amino acids
DE10225367C1 (de) 2002-06-06 2003-09-18 Ilf Forschungs Und Entwicklung Härtbare Zubereitungen
US7745508B2 (en) 2002-08-30 2010-06-29 Ppg Industries Ohio, Inc. Compositions and methods for coating food cans
JP2004250505A (ja) 2003-02-18 2004-09-09 Sentan Gijutsu Incubation Systems:Kk コーティング組成物、コーティング薄膜および複合材料
US7122684B2 (en) 2003-03-13 2006-10-17 Roche Colorado Corporation Process for preparing 1,2-diamino compounds
US7960444B2 (en) 2003-04-25 2011-06-14 Dow Global Technologies Llc Vegetable oil based polyols and polyurethanes made therefrom
US8357749B2 (en) 2003-08-25 2013-01-22 Dow Global Technologies Llc Coating composition and articles made therefrom
US8293808B2 (en) * 2003-09-30 2012-10-23 Cargill, Incorporated Flexible polyurethane foams prepared using modified vegetable oil-based polyols
US7192992B2 (en) 2004-02-04 2007-03-20 Ecology Coating, Inc. Environmentally friendly, 100% solids, actinic radiation curable coating compositions for coating thermally sensitive surfaces and/or rusted surfaces and methods, processes and assemblages for coating thereof
DE102004012902A1 (de) 2004-03-17 2005-10-06 Bayer Materialscience Ag Herstellung von neuen strahlenhärtenden Bindemitteln
DE102004047921A1 (de) 2004-10-01 2006-04-06 Bayer Materialscience Ag Polyisocyanate mit sterisch anspruchsvollen Phenolen blockiert
EP2420542B2 (en) 2004-10-20 2018-09-19 Valspar Sourcing, Inc. Article and method of coating
US7321010B2 (en) 2005-03-08 2008-01-22 Johns Manville Fiberglass binder utilizing a curable acrylate and/or methacrylate
CN1323122C (zh) 2005-05-09 2007-06-27 汕头市长崎制漆有限公司 真空镀膜涂料
US7807230B2 (en) 2005-06-16 2010-10-05 Rensselaer Polytechnic Institute Curcumin and curcuminoid compounds, and use thereof as photosensitizers of onium salts
MX2008000776A (es) 2005-07-22 2008-03-10 Nova Chem Inc Sistema, aparato y procedimiento para revestir y curar recipientes desechables.
GB2428678B (en) 2005-08-02 2010-01-27 Univ Keele Glyceride compounds and uses thereof
US8142858B2 (en) 2005-08-11 2012-03-27 Valspar Sourcing, Inc. Bisphenol A and aromatic glycidyl ether-free coatings
DE102005056959A1 (de) 2005-11-29 2007-05-31 W.R. Grace & Co. Conn. Badge- und BPA-freie Dosenbeschichtung
US8043713B2 (en) 2005-12-15 2011-10-25 Dow Global Technologies Llc Compositions and aqueous dispersions
TW200813159A (en) * 2006-04-26 2008-03-16 Dow Corning Korea Ltd A liquid silicone rubber composition for forming breathable coating film on a textile and process for forming a breathable coating film on a textile
US8471072B2 (en) * 2006-05-09 2013-06-25 The Curators Of The University Of Missouri Soy-based polyols
US20080233062A1 (en) 2006-08-24 2008-09-25 Venkataram Krishnan Cationic latex as a carrier for active ingredients and methods for making and using the same
US20080207774A1 (en) 2006-08-24 2008-08-28 Venkataram Krishnan Anionic latex as a carrier for active ingredients and methods for making and using the same
US7910680B2 (en) * 2006-11-08 2011-03-22 Dow Global Technologies Llc Reactive (meth)acrylate monomer compositions and preparation and use thereof
JP5506143B2 (ja) 2006-11-28 2014-05-28 関西ペイント株式会社 ライナー付着性が良好なキャップ用塗料組成物及び当該塗料組成物を塗装したキャップ
KR20100017381A (ko) 2007-04-27 2010-02-16 다우 글로벌 테크놀로지스 인크. 재생가능한 오일로부터의 저 휘발성 물질 코팅, 실란트 및 결합제
US7868085B2 (en) 2007-07-05 2011-01-11 Ppg Industries Ohio, Inc. Aqueous dispersion comprising a branched triol having trimellitic anhydride and associated method
MX2009013258A (es) 2007-07-12 2010-01-25 Cytec Surface Specialties Sa Composiciones de aceite natural acrilado.
CN101195577A (zh) 2007-12-13 2008-06-11 天津工业大学 一种由大豆油制备多元醇的方法
CN101225141B (zh) * 2007-12-28 2011-06-01 沈阳工业大学 以大豆油为原料制备可降解聚合物
ES2437599T3 (es) * 2008-01-24 2014-01-13 Polyone Corporation Catalizadores para la esterificación de sojatos epoxidados y métodos de uso de los mismos
US20100055467A1 (en) 2008-09-02 2010-03-04 Ppg Industries Ohio, Inc. Coating compositions comprising the reaction product of a biomass derived polyol and a lactide
US8921477B2 (en) 2008-10-13 2014-12-30 Eastern Michigan University Conventional latex / nanolatex blends
MX341307B (es) 2008-11-26 2016-08-15 Valspar Sourcing Inc Polimero de poliester-carbamato y composiciones de recubrimiento de este polimero.
RU2391368C1 (ru) 2008-12-24 2010-06-10 Открытое акционерное общество "Конструкторское бюро автоматических линий им. Л.Н. Кошкина" Модифицирующая добавка для водоразбавляемого полимера полиоргансилоксана и сополимера бутадиена со стиролом
WO2010097353A1 (en) 2009-02-24 2010-09-02 Akzo Nobel Coatings International B.V. Latex emulsions and coating compositions formed from latex emulsions
MX2011009154A (es) 2009-03-05 2011-10-10 Akzo Nobel Coatings Int Bv Polioles de aceite con funcion de hidroxilo y composiciones de recubrimiento preparadas de polioles de aceite con funcion de hidroxilo.
CN102421815A (zh) 2009-03-30 2012-04-18 陶氏环球技术有限责任公司 混合分散体及其生产方法
WO2011009024A1 (en) 2009-07-17 2011-01-20 Valspar Sourcing, Inc. Coating compositions for cans and methods of coating
US20120118785A1 (en) 2009-07-24 2012-05-17 Dow Global Technologies Inc. Coated container device, method of making the same
WO2011011705A2 (en) 2009-07-24 2011-01-27 Dow Global Technologies Inc. A coated container device, method of making the same
CN102686638B (zh) 2009-10-30 2015-04-01 陶氏环球技术有限责任公司 醇酸分散体、及其制备方法
WO2012089655A2 (en) 2010-12-28 2012-07-05 Akzo Nobel Coatings International B.V. Radiation curable coating compositions for metal
KR101949209B1 (ko) 2010-12-29 2019-04-22 아크조노벨코팅스인터내셔널비.브이. 접착 촉진제 수지 조성물 및 상기 접착 촉진제 수지 조성물을 포함하는 코팅 조성물
KR102025208B1 (ko) 2011-12-21 2019-09-25 아크조노벨코팅스인터내셔널비.브이. 수성 코팅 조성물
RU2605418C2 (ru) 2011-12-21 2016-12-20 Акцо Нобель Коатингс Интернэшнл Б.В. Покрывные композиции на основе растворителей

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006012344A1 (en) * 2004-06-25 2006-02-02 Pittsburg State University Modified vegetable oil-based polyols
WO2007127379A1 (en) * 2006-04-27 2007-11-08 Pittsburg State University Enhanced oligomeric polyols and polymers made therefrom
WO2008151286A1 (en) * 2007-06-05 2008-12-11 The Glidden Company Radiation curable coating composition derived from epoxidized vegetable oils

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105008470A (zh) * 2013-03-12 2015-10-28 阿克佐诺贝尔国际涂料股份有限公司 用于制备可辐射固化低聚物的协同增效催化剂组合

Also Published As

Publication number Publication date
HK1162189A1 (zh) 2012-08-24
RU2011139425A (ru) 2013-04-10
WO2010100122A1 (en) 2010-09-10
RU2011139424A (ru) 2013-04-10
ES2693159T3 (es) 2018-12-07
KR101695168B1 (ko) 2017-01-11
CA2753911C (en) 2018-04-03
EP2403885B1 (en) 2018-08-29
ZA201105581B (en) 2012-12-27
US20110294946A1 (en) 2011-12-01
AU2010220406C1 (en) 2016-07-21
RU2539981C2 (ru) 2015-01-27
AU2010220405B2 (en) 2016-01-14
CN102333801B (zh) 2015-11-25
MY173945A (en) 2020-02-28
HK1162547A1 (zh) 2012-08-31
WO2010100121A1 (en) 2010-09-10
AU2010220405A1 (en) 2011-08-18
AU2010220406A1 (en) 2011-08-18
ZA201105580B (en) 2012-12-27
US9133292B2 (en) 2015-09-15
RU2543878C2 (ru) 2015-03-10
KR20110132336A (ko) 2011-12-07
AU2010220406B2 (en) 2016-01-14
EP2403914A1 (en) 2012-01-11
EP2403885A1 (en) 2012-01-11
US20120022186A1 (en) 2012-01-26
KR20110131189A (ko) 2011-12-06
CN102333801A (zh) 2012-01-25
MX2011009155A (es) 2011-10-10
CA2753864A1 (en) 2010-09-10
CN102333833B (zh) 2015-01-21
CA2753911A1 (en) 2010-09-10
AU2010220405C1 (en) 2016-04-21
MX2011009154A (es) 2011-10-10

Similar Documents

Publication Publication Date Title
CN102333833A (zh) 羟基官能油多元醇和由羟基官能油多元醇制备的涂料组合物
AU2010220406B9 (en) Hydroxyl functional oil polyols and coating compositions prepared from hydroxyl functional oil polyols
CA2822750C (en) Adhesion promoter resin compositions and coating compositions having the adhesion promoter resin compositions
EP2751201B1 (en) Coating compositions for food and beverage containers
CN105189684A (zh) 具有羟基苯基官能聚合物的涂料组合物
CN104024293A (zh) 水基涂料组合物
CN103998480A (zh) 溶剂基涂料组合物
CN103562256A (zh) 包含2,2’-联苯酚的涂料组合物
US6103834A (en) Polymer composition derived from unsaturated vegetable oils
KR102187118B1 (ko) 하이브리드 가교제 시스템을 이용하여 제조되는 마이크로겔, 및 이로부터 제조되는 마이크로겔을 함유한 코팅 조성물
CN105008470A (zh) 用于制备可辐射固化低聚物的协同增效催化剂组合
WO2022251858A1 (en) Polyester copolymer and coating compositions therefrom having improved corrosion resistance
EP4341311A1 (en) Coating compositions and articles coated therewith

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
REG Reference to a national code

Ref country code: HK

Ref legal event code: DE

Ref document number: 1162189

Country of ref document: HK

C14 Grant of patent or utility model
GR01 Patent grant
REG Reference to a national code

Ref country code: HK

Ref legal event code: GR

Ref document number: 1162189

Country of ref document: HK

CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20150121

Termination date: 20170302

CF01 Termination of patent right due to non-payment of annual fee