CN1863837A - 含有醇官能的有机硅树脂的聚氨酯组合物 - Google Patents
含有醇官能的有机硅树脂的聚氨酯组合物 Download PDFInfo
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- CN1863837A CN1863837A CNA2004800289641A CN200480028964A CN1863837A CN 1863837 A CN1863837 A CN 1863837A CN A2004800289641 A CNA2004800289641 A CN A2004800289641A CN 200480028964 A CN200480028964 A CN 200480028964A CN 1863837 A CN1863837 A CN 1863837A
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Classifications
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
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Abstract
本发明涉及一种聚氨酯组合物,它包括(A)100重量份含至少一个异氰酸酯基的至少一种化合物;(B)0.3-300重量份醇官能的有机硅树脂;(C)最多250重量份有机多元醇;和(D)最多10重量份固化速率改进剂。本发明的聚氨酯组合物可用作可独立应用的涂层或者用作保护性涂层、油漆配方和粉末涂层。本发明的聚氨酯组合物也可与发泡剂和泡孔稳定剂一起配制,以产生热稳定的泡沫体配方。
Description
[0001]本领域已知硅氧烷树脂具有优越的热稳定性和耐候性,其中包括低的吸水性。然而,其韧性、粘合性和尺寸稳定性差(低Tg,高CTE)限制了其应用。聚氨酯树脂显示出非常良好的韧性,但缺点是边缘热稳定性和耐候性。本发明涉及醇官能的有机硅树脂作为制备聚氨酯组合物中的组分或用于电子封装的用途,其中所述聚氨酯组合物可充当保护性涂层,例如用作木地板涂层。或者,可将泡孔稳定剂和发泡剂加入到本发明的聚氨酯组合物中,产生具有提高的热稳定性的的聚氨酯泡沫体。含醇的硅氧烷已在本领域中用于聚氨酯组合物中。例如,在美国专利No.4684538中,公开了有机硅聚氨酯配合物,例如聚硅氧烷聚氨酯(甲基)丙烯酸酯,它以聚硅氧烷醇、聚异氰酸酯和具有对该聚异氰酸酯中的异氰酸酯基具有反应性且在与其反应之后在反应产物内提供烯键式官能团的至少一个官能团的多官能团化合物的反应产物形式获得。该聚硅氧烷醇的分子量为约5000-约50000且具有R′OH端基,其中R′是直链C4-C20亚烷基。这种醇可以以相应的氢化物封端的聚硅氧烷和直链C4-C20ω-链烯基醇的反应产物形式获得。所公开的配合物可用在粘合剂组合物(其用于包括粘结表面例如玻璃的基底)中,和烯键式不饱和单体的聚合物与共聚物中。
[0002]在美国专利No.5814679中,公开了可光固化的硅氧烷组合物与含有醇官能团的长链硅氧烷化合物的共混物。′679专利进一步公开了含硅氧烷的长链醇与环氧官能的可光固化的硅氧烷共聚或共固化,从而使得可形成优良剥离性的可光固化的硅氧烷组合物的配方。
美国专利No.6610777公开了由包括下述的组分形成的涂料组合物:(a)含至少一种反应性官能团的至少一种聚硅氧烷,其中该至少一种聚硅氧烷包括至少一种下述结构单元(I):
R1 nR2 mSiO(4-n-m)/2 (I)
其中每一R1可以相同或不同,代表H、OH、单价烃基或单价硅氧烷基;每一R2可以相同或不同,代表含至少一个反应性官能团的基团,其中m和n满足条件0<n<4,0<m<4和2<(m+n)≤4;(b)羟值范围为100-200的至少一种多元醇;和(c)含对选自至少一种聚硅氧烷(a)中的至少一个反应性官能团和至少一种多元醇(b)中的至少一个官能团中的至少一个官能团具有反应性的至少一个官能团的至少一种反应物,其中每一组分不同,和其中根据挠性试验方法,在70的温度下,由该涂料组合物形成的涂层当固化时的挠性等级为至少6。
[0003]在美国专利No.5939491中,公开了一种可固化的组合物,所述可固化的组合物包括可含有各种反应性官能团的有机聚硅氧烷和含有对该聚硅氧烷中的官能团具有反应性的官能团的固化剂。这种可固化组合物尤其可用于涂料组合物中,所述涂料组合物可在环境和热固化条件下固化,其中它们提供诸如增加的适用期、改进的发粘时间、粘合性、抗擦伤性和抗酸蚀刻之类的优良性能。
该可固化组合物包括含有反应性官能团的有机聚硅氧烷和含有对该有机聚硅氧烷中的官能团具有反应性的官能团的组分,所述聚硅氧烷具有下述通式结构:
其中m为至少1;m′为0-50;n为0-50;R选自OH和连接到硅原子上的单价烃基;Ra具有下述结构:R1-O-X,其中R1是亚烷基、氧基亚烷基或亚烷基芳基;和X是含有选自下述的官能团的部分:OH、COOH、NCO、羧酸酯(例如酯、碳酸酯和酸酐)、伯胺、仲胺、酰胺、氨基甲酸酯和环氧官能团。优选地,可固化组合物包括:(a)含有反应性官能团的有机聚硅氧烷,该聚硅氧烷具有通式(II)或(III),其中m、m′、n、R、Ra和X如上所述;(b)含有反应性官能团的聚合物或低聚物;和(c)含有对(a)和(b)中的官能团具有反应性的官能团的固化剂。在一个优选的实施方案中,n+m和n+m′为2或3。
[0004]本发明涉及一种聚氨酯组合物,它包括:(A)100重量份含至少一个异氰酸酯基的至少一种化合物;(B)3-300重量份含下述单元的醇(carbinol)官能的有机硅树脂:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1和R2各自独立地为氢原子、具有1-8个碳原子的烷基、芳基、具有至少3个碳原子的不含芳基的醇基,或者具有至少6个碳原子的含芳基的醇基,R3是具有1-8个碳原子的烷基,或芳基,a的数值小于或等于0.6,b的数值为0或大于0,c的数值大于0,d的数值小于0.5,和a+b+c+d=1,和条件是当每一R2是甲基时,b的数值小于0.3,和(C)最多250重量份有机多元醇;和(D)最多10重量份固化速率改进剂。
[0005]本发明另一实施方案涉及一种聚氨酯组合物,它包括:(A)100重量份含至少一个异氰酸酯基的至少一种化合物;(B)0.3-300重量份含下述单元的醇官能的有机硅树脂:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1和R2各自独立地为氢原子、具有1-8个碳原子的烷基、芳基、具有至少3个碳原子的不含芳基的醇基,或者具有至少6个碳原子的含芳基的醇基,R3是具有1-8个碳原子的烷基,或芳基,a的数值小于或等于0.6,b的数值为0或大于0,c的数值大于0,d的数值小于0.5,和a+b+c+d=1,和条件是当每一R2是甲基时,b的数值小于0.3,和条件是每一树脂分子平均具有至少一个醇基;(C)最多250重量份有机多元醇;和(D)最多10重量份固化速率改进剂,其中醇基与异氰酸酯基的摩尔比为约0.8∶1到1.2∶1。
[0006]本发明另一实施方案涉及一种聚氨酯组合物,它包括:(A)含至少一个异氰酸酯基的至少一种化合物;和(B)含下述单元的醇官能的有机硅树脂:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1和R2各自独立地为氢原子、具有1-8个碳原子的烷基、芳基、具有至少3个碳原子的不含芳基的醇基,或者具有至少6个碳原子的含芳基的醇基,R3是具有1-8个碳原子的烷基,或芳基,a的数值小于或等于0.6,b为0或大于0,c的数值大于0,d的数值小于0.5,和a+b+c+d=1,和条件是当每一R2是甲基时,b的数值小于0.3,其中醇基与异氰酸酯基的摩尔比为约0.8∶1到1.2∶1。
[0007]本发明另一实施方案涉及一种聚氨酯组合物,它通过包括下述步骤的方法而获得:使(A)100重量份含至少一个异氰酸酯基的至少一种化合物;(B)3-300重量份含下述单元的醇官能的有机硅树脂:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1和R2各自独立地为氢原子、具有1-8个碳原子的烷基、芳基、具有至少3个碳原子的不含芳基的醇基,或者具有至少6个碳原子的含芳基的醇基,R3是具有1-8个碳原子的烷基,或芳基,a的数值小于或等于0.6,b的数值为0或大于0,c的数值大于0,d的数值小于0.5,和a+b+c+d=1,和条件是当每一R2是甲基时,b的数值小于0.3;(C)最多250重量份有机多元醇;和(D)最多10重量份固化速率改进剂反应。
[0008]本发明另一实施方案涉及一种聚氨酯组合物,它通过包括下述步骤的方法而获得:使(A)100重量份含至少一个异氰酸酯基的至少一种化合物;(B)0.3-300重量份含下述单元的醇官能的有机硅树脂:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1和R2各自独立地为氢原子、具有1-8个碳原子的烷基、芳基、具有至少3个碳原子的不含芳基的醇基,或者具有至少6个碳原子的含芳基的醇基,R3是具有1-8个碳原子的烷基,或芳基,a的数值小于或等于0.6,b的数值为0或大于0,c的数值大于0,d的数值小于0.5,和a+b+c+d=1,和条件是当每一R2是甲基时,b的数值小于0.3,和条件是每一树脂分子平均具有至少一个醇基;(C)最多250重量份有机多元醇;和(D)最多10重量份固化速率改进剂反应,其中醇基与异氰酸酯基的摩尔比为约0.8∶1到1.2∶1。
[0009]本发明另一实施方案涉及一种聚氨酯组合物,它通过包括下述步骤的方法而获得:使(A)含至少一个异氰酸酯基的至少一种化合物;和(B)含下述单元的醇官能的有机硅树脂反应:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1和R2各自独立地为氢原子、具有1-8个碳原子的烷基、芳基、具有至少3个碳原子的不含芳基的醇基,或者具有至少6个碳原子的含芳基的醇基,R3是具有1-8个碳原子的烷基,或芳基,a的数值小于或等于0.6,b的数值为0或大于0,c的数值大于0,d的数值小于0.5,和a+b+c+d的数值=1,和条件是当每一R2是甲基时,b的数值小于0.3,其中醇基与异氰酸酯基的摩尔比为约0.8∶1到1.2∶1。
[0010]组分(A)可以是在先前制备交联聚氨酯中使用的任何含多异氰酸酯基的分子。组分(A)中含有至少一个异氰酸酯基的化合物通常可例举异佛尔酮二异氰酸酯三聚体,异佛尔酮二异氰酸酯,甲苯二异氰酸酯,多异氰酸酯,四甲基亚二甲苯基二异氰酸酯,亚苯基二异氰酸酯,二甲苯二异氰酸酯,1,5-萘二异氰酸酯,氯亚苯基2,4-二异氰酸酯,双甲苯二异氰酸酯,二茴香胺二异氰酸酯,甲苯胺二异氰酸酯和烷基化苯二异氰酸酯;亚甲基间隔的芳族二异氰酸酯,如亚甲基联苯基二异氰酸酯,特别是4,4′-异构体(MDI),其中包括烷基化同系物,例如3,3′-二甲基-4,4′-联苯基甲烷二异氰酸酯,氢化物质,例如环亚己基二异氰酸酯,4,4′-亚甲基二环己基二异氰酸酯;混合芳烷基二异氰酸酯,例如四甲基二甲苯二异氰酸酯,OCNC(CH3)2C6H4C(CH3)2NCO,和通常称为异佛尔酮二异氰酸酯的二异氰酸酯,它是3,3,5-三甲基-5-异氰酸甲酯基环己基异氰酸酯;和聚亚甲基异氰酸酯,例如1,4-四亚甲基二异氰酸酯,1,5-五亚甲基二异氰酸酯,1,6-亚己基二异氰酸酯(HMDI),1,7-七亚甲基二异氰酸酯,2,2,4-和2,4,4-三甲基六亚甲基二异氰酸酯,1,10-十亚甲基二异氰酸酯和2-甲基-1,5-五亚甲基二异氰酸酯。上述异氰酸酯可单独或结合使用。
[0011]适合作为组分(A)的可商购材料可例举由Rhodia(Cranbury,NJ)销售的Tolonate XIDT 70SB异佛尔酮二异氰酸酯三聚体(70%固体,12.3wt%NCO)和Desmodur N-100多异氰酸酯(获自Mobay Corp.)。
[0012]对于本发明的目的来说,“醇基”定义为含有至少一个与碳键合的羟基(COH)的任何基团。因此,醇基可含有大于一个COH基,例如
[0013]在组分(B)中的醇官能的有机硅树脂内的R1和R2的烷基可例举甲基、乙基、丙基、丁基、戊基、己基和辛基,其中烷基典型地为甲基。R1和R2的芳基可例举苯基、萘基、苄基、甲苯基、二甲苯基、联苯基、甲基苯基、2-苯乙基、2-苯基-2-甲基乙基、氯代苯基、溴代苯基和氟代苯基,其中芳基典型地为苯基。
[0014]具有至少3个碳原子的不含芳基的醇基可例举具有化学式R4OH的基团,其中R4是具有至少3个碳原子的二价烃基或具有至少3个碳原子的二价烃氧基。R4基可例举选自-(CH2)x-(其中x的数值为3-10)、-CH2CH(CH3)-、-CH2CH(CH3)CH2-、-CH2CH2CH(CH2CH3)CH2CH2CH2-和-OCH(CH3)(CH2)x-的亚烷基,其中x的数值为1-10。具有至少3个碳原子的不含芳基的醇基还可例举具有化学式R6(OH)CH2OH的基团,和R6是具有化学式-CH2CH2(CH2)xOCH2CH2-的基团,其中x的数值为1-10。
[0015]具有至少6个碳原子的含芳基的醇基可例举具有化学式R5OH的基团,其中R5是选自(CH2)xC6H4-(其中x的数值为0-10)、-CH2CH(CH3)(CH2)xC6H4-(其中x的数值为0-10)和-(CH2)xC6H4(CH2)x-(其中x的数值为1-10)的亚芳基。含有芳基的醇基典型地具有6-14个原子。
[0016]在醇官能的有机硅树脂组分(B)中,a的典型数值为0.1-0.6,或者0.2-0.4,b的典型数值为0-0.4,或者0-0.1,c的典型数值为0.3-0.8,或者0.4-0.8,d的典型数值为0-0.3,或者0。当每一R2是甲基时,b的数值小于0.3或者小于0.1。
[0017]醇官能的有机硅树脂每一树脂分子平均具有至少一个醇基。典型地,在醇官能的有机硅树脂上的醇基的当量为100-1000,或者200-800。
[0018]典型地,当醇官能的有机硅树脂中R1或R2含有醇基时,仅仅一个醇基将存在于每一R1或R2上。
[0019]组分(B)的醇官能的有机硅树脂可例举:
含下述单元的醇官能的有机硅树脂:
((CH3)3SiO1/2)a
((R2)CH3SiO2/2)b,其中R2=-(CH2)3C6H4OH
(C6H5)CH3SiO2/2)b,和
(C6H5SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((R1)(CH3)2SiO1/2)6,其中R1=-(CH2)3C6H4OH和
(C6H5SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((R1)(CH3)2SiO1/2)a,其中R1=-(CH2)3C6H4OH和
(CH3SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((R1)(CH3)2SiO1/2)a,其中R1=-(CH2)3OH和
(C6H5SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((R1)(CH3)2SiO1/2)a,其中R1=-(CH2)3OH
(CH3SiO3/2)c和
(C6H5SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((CH3)3SiO1/2)a,
((R2)CH3SiO2/2)b,其中R2=-(CH2)3OH
((C6H5)CH3SiO2/2)b和
(C6H5SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((CH3)3SiO1/2)a,
((R1)(CH3)2SiO1/2)a,其中R1=-(CH2)3OH和
(C6H5SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((R1)(CH3)2SiO1/2)a,其中R1=-CH2CH(CH3)CH2OH
((H)(CH3)2SiO1/2)a和
(C6H5SiO3/2)c,以及
含下述单元的醇官能的有机硅树脂:
((R1)(CH3)2SiO1/2)a,其中R1=-(CH2)3OH
(CH3SiO3/2)c,
其中a的典型数值为0.1-0.6,b的典型数值为0-0.4,和c的典型数值为0.3-0.8。
[0020]优选地,在醇官能的有机硅树脂内的R1+R2+R3基含有足够高的苯基含量,以提供与组分(A)合适的相容性。典型地大于10wt%的R1+R2+R3基是苯基,和甚至更典型地大于25wt%的R1+R2+R3基是苯基。
[0021]通过包括下述步骤的方法:在(C′)氢化硅烷化催化剂,和任选地(D′)至少一种溶剂存在下,使
(A′)含下述单元的至少一种氢官能的有机硅树脂:
(R7 3SiO1/2)a(i)
(R8 2SiO2/2)b(ii)
(R3SiO3/2)c(iii)和
(SiO4/2)d (iv)
其中R7和R8各自独立地为具有1-8个碳原子的烷基,芳基,或氢原子,R3、a、b、c和d如上所定义,a+b+c+d=1,条件是当每一R8是甲基时,b的数值小于0.3,条件是在有机硅树脂内存在至少两个与硅键合的氢原子;和(B′)至少一种乙烯基封端的醇反应,从而制备醇官能的有机硅树脂。制备组分(B)的醇官能的有机硅树脂的方法详细地公开于标题为“醇官能的有机硅树脂”这一悬而未决的专利申请中,在此通过参考将其引入。
[0022]R7和R8中的烷基与芳基与以上对于R1和R2中所述的一样。
[0023]组分(C),有机多元醇(与有机醇同义)可例举乙二醇、1,2-丙二醇、1,3-丙二醇、1,4-丁二醇、2,3-丁二醇、1,6-己二醇、1,8-辛二醇、辛戊二醇、环己烷二甲醇、2-甲基-1,3-丙二醇、甘油、trimeth1,2,61、1,2,4-丁三醇、季戊四醇、甘露糖醇、山梨醇、二甘醇、三甘醇、四甘醇、通常聚(乙烯氧基)二元醇、二丙二醇、通常聚(丙烯氧基)二元醇、二丁二醇、聚(丁烯氧基)二元醇和聚己内酯。可使用的较高分子量的其它多羟基物质是诸如环氧乙烷、环氧丙烷、环氧丁烷、氧化苯乙烯之类的环氧化物和表氯醇的聚合产物。含羟基的聚酯、聚硫醚、聚缩醛、聚碳酸酯和聚酯酰胺也可单独或结合上述多元醇使用。合适的聚酯包括多元醇与多元羧酸,优选二元羧酸的反应产物。常常使用的多元醇包括以上提及的二元醇。二羧酸的实例包括琥珀酸、己二酸、辛二酸、癸二酸、壬二酸、戊二酸、邻苯二甲酸、马来酸和富马酸。典型的聚醚多元醇可例举具有化学式HO(RO)nH的聚亚烷基醚多元醇,其中R是亚烷基和n是足够大的整数,以使该聚醚多元醇的数均分子量为至少250。这些聚亚烷基醚多元醇是聚氨酯产物的公知组分且可通过聚合环醚如环氧烷和二元醇、二羟基醚和通过类似的已知方法来制备。特别常见的高分子量多元醇是聚丁二醇。
[0024]组分(D),固化速率改进剂可以是影响聚氨酯组合物固化时间的任何物质,和包括固化促进剂、固化抑制剂和固化催化剂。实例包括膦化合物,例如三丁基膦、三苯基膦、三(二甲氧基苯基)膦、三(羟丙基)膦和三(氰乙基)膦;盐,例如四苯基四苯基硼酸盐,甲基三丁基四苯基硼酸盐,和甲基三氰乙基四苯基硼酸盐,咪唑,例如2-甲基咪唑,2-苯基咪唑,2-乙基-4-甲基咪唑,2-十一烷基咪唑,1-氰乙基-2-甲基咪唑,1,4-二氢基-6-[2-甲基咪唑基-(1)]-乙基-S-三嗪和2,4-二氰基-6-[2-十一烷基咪唑基-(1)]-乙基-S-三嗪;咪唑盐,例如1-氰乙基-2-十一烷基咪唑偏苯三酸盐,2-甲基咪唑异氰脲酸盐,2-乙基-4-甲基咪唑四苯基硼酸盐和2-乙基-1,4-二甲基咪唑四苯基硼酸盐;胺,例如2,4,6-三(二甲基氨甲基)苯酚,苄基二甲基胺,四甲基丁基胍,N-甲基哌嗪和2-二甲基氨基-1-吡咯啉;铵盐,例如四苯基硼酸三乙铵;二偶氮双环化合物,例如1,5-二氮杂双环(5,4,0)-7-十一碳烯,1,5-二氮杂双环(4,3,0)-5-壬烯和1,4-二氮杂双环(2,2,2)-辛烷;和四苯基硼酸盐,苯酚盐,可溶可熔酚醛树脂盐和这些二氮杂双环化合物的2-乙基己酸盐,和醇,例如间苯二酚。在这些化合物当中,典型地使用叔胺,膦化合物,咪唑化合物,二氮杂双环化合物,及其盐。也可使用双氰胺和三氟化硼。
[0025]组分(D)固化速率改进剂也可例举具有脂族不饱和键的化合物,有机磷化合物,有机硫化合物,含氮化合物和锡化合物。具有脂族不饱和键的化合物的实例包括炔丙醇、烯-炔化合物,和马来酸酯,例如马来酸二甲酯。有机磷化合物的实例是三有机膦,二有机膦,有机phosphones和三有机亚磷酸酯。有机硫化合物包括有机硫醇,二有机硫化物,硫化氢,苯并噻唑,和苯并噻唑亚硫酸氢盐。含氮化合物包括氨,伯、仲或叔烷胺,芳胺,脲和肼。胺可例举三乙胺、三丁胺、N-甲基吗啉、N-乙基吗啉、1,4-二氮杂双环(2,2,2)-辛烷、N-鲸蜡基二甲胺、N-甲基-N′-二甲基氨基乙基哌嗪、N,N-二甲基苄胺、N,N-二甲基环己基胺和1,2-二甲基咪唑。也可使用有机锡化合物且包括诸如羧酸的锡(II)盐,例如乙酸锡(II)、辛酸锡(II)、乙基己酸锡(II)和月桂酸锡(II)之类的物质,以及诸如以二丁基二乙酸锡、二丁基二月桂酸锡、二丁基马来酸锡和二辛基二乙酸锡为例子的羧酸的二烷基锡盐之类的物质。可单独使用这些锡盐或者作为与脒,例如氨基吡啶,氨基嘧啶,肼基吡啶和四氢嘧啶的络合物。也可使用其它金属基化合物,例如铅、铁、汞、铋、钴和锰,且包括诸如乙酰丙酮酸钴(III),萘甲酸钴,萘甲酸锰,油酸铅,环烷酸锌和环烷酸锆之类的化合物。也可使用其它化合物,例如硅杂胺和碱性氮化合物,例如四烷基氢氧化铵,碱金属氢氧化物,例如氢氧化钠,和碱金属醇化物,例如甲醇钠。基于聚异氰酸酯的用量和与聚异氰酸酯反应的物质的用量,通常以约0.01-约10wt%,优选约0.05-约1.0wt%的用量使用组分(D)的固化速率改进剂。
[0026]典型地,在聚氨酯组合物内醇基与异氰酸酯基的摩尔比为约0.8∶1到1.2∶1。
[0027]本发明的聚氨酯组合物可进一步包括常规地在可聚合体系内使用的其它组分。这些组分包括但不限于溶剂、增塑剂、颜料、着色剂、染料、表面活性剂、增稠剂、热稳定剂、流平剂、防堵孔剂、填料、沉降抑制剂、紫外光吸收剂和类似物。添加剂,例如促进剂,热稳定剂,紫外光吸收剂等可紧密地分散在反应混合物内,因此在表观上变为聚合物的一个整体部分。优选的抗氧剂是位阻酚化合物。稳定剂,例如有机亚磷酸酯也是有用的。优选的UV抑制剂是苯并***化合物。
[0028]本发明的聚氨酯组合物可进一步包括以中空微球、煅制氧化硅、沉淀氧化硅、水合硅酸、炭黑、粉末石英、碳酸钙、碳酸镁、硅藻土、硅灰石、焙烧粘土、粘土、滑石、高岭土、氧化钛、膨润土、氧化铁、氧化锌、玻璃球、玻璃珠、云母、玻璃粉、玻璃球、煤灰、丙烯酸树脂粉末、酚醛树脂粉末、陶瓷粉末、沸石、板岩粉、有机纤维和无机纤维为例子的至少一种填料。
[0029]本发明的聚氨酯组合物可进一步包括至少一种泡孔稳定剂和至少一种发泡剂,和任选地增链剂和交联剂。泡孔稳定剂可例举硅氧烷,其中典型地使用硅氧烷聚醚。发泡剂可例举水、液体二氧化碳、CFC、HCFC、HFC和戊烷,其中典型地使用水或水与HCFC的混合物。添加这些成分到本发明的聚氨酯组合物中产生具有提高的热稳定性的聚氨酯泡沫体组合物。
[0030]可通过混合(或机械搅拌)组分(A)和(B),和任何任选的组分,形成均匀混合物,从而制备本发明的聚氨酯组合物。这可通过本领域已知的任何方便的混合方法来实现,其中可例举刮刀、机械搅拌器、含有挡板和/或浆叶的在线混合体系、动力在线混合器、均化器、圆筒辊、三辊磨机、∑形桨式混合机、面包揉面机和双辊磨机。认为混合顺序不是关键的。可预混合组分(A)和(B)和任何任选的组分,且若消粘时间短的话,则在施涂过程中施涂或混合。
[0031]本发明还涉及一种聚氨酯组合物,它通过包括下述步骤的方法而获得:使(A)100重量份含至少一个异氰酸酯基的至少一种化合物;(B)3-300重量份含下述单元的醇官能的有机硅树脂:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1、R2、R3、a、b、c和d如上所定义,和a+b+c+d=1,和条件是当每一R2是甲基时,b的数值小于0.3;(C)最多250重量份有机多元醇;和(D)最多10重量份固化速率改进剂反应。
[0032]本发明另一实施方案还涉及一种聚氨酯组合物,它通过包括下述步骤的方法而获得:使(A)100重量份含至少一个异氰酸酯基的至少一种化合物;(B)0.3-300重量份含下述单元的醇官能的有机硅树脂:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1、R2、R3、a、b、c和d如上所定义,和a+b+c+d=1,条件是当每一R2是甲基时,b的数值小于0.3,和条件是每一树脂分子平均具有至少一个醇基;(C)最多250重量份有机多元醇;和(D)最多10重量份固化速率改进剂反应,其中聚氨酯组合物中醇基与异氰酸酯基的摩尔比为约0.8∶1到1.2∶1。
[0033]本发明另一实施方案还涉及一种聚氨酯组合物,它通过包括下述步骤的方法而获得:使(A)含至少一个异氰酸酯基的至少一种化合物;(B)含下述单元的醇官能的有机硅树脂反应:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1、R2、R3、a、b、c和d如上所定义,和a+b+c+d=1,h条件是当每一R2是甲基时,b的数值小于0.3;其中醇基与异氰酸酯基的摩尔比为约0.8∶1到1.2∶1。
[0034]此处所使用的“反应”是指在室温(20-25℃)下,混合组分(A)和(B)和任何任选的组分,或者加热含(A)和(B)和任何任选的组分的混合物到高于室温的温度,例如最多200℃的温度下。组分(A)-(D)如上所述。
[0035]本发明的聚氨酯组合物可用作可独立应用的涂料或者用作保护性涂料、油漆配方和粉末涂料中的成分。本发明的聚氨酯组合物也可与发泡剂和泡孔稳定剂一起配制,以产生热稳定的泡沫体配方。
实施例
[0036]材料:
异氰酸酯:Tolonate XIDT 70SB是由Rhodia(Cranbury,NJ)销售的异佛尔酮二异氰酸酯三聚体(70%固体,12.3wt%NCO)。
多元醇:Desmophen870 BA是由BayerCorporation(Pittsburgh,PA)供应的在乙酸丁酯内的羟基官能的聚丙烯酸酯树脂(70%固体)。
异氰酸酯:Desmodur N-3390是由BayerCorporation(Pittsburgh,PA)供应的在乙酸丁酯内的基于六亚甲基二异氰酸酯(HDI)的聚异氰酸酯(90%固体)。
Tegokat218是由Goldschmidt(McDonald,PA)销售的二月桂酸二丁基锡。
试验方法:
量柱斜度器(stylometer)划痕粘附性
[0037]当样品以恒定的行进速度移动时,球形金刚石以恒定的负载速度贴着涂层表面施压。增加力,直到涂层灾变性地破损。破坏力是类似特征和厚度的样品的相对粘附性的量度。认为可开发技术以测量涂层的拉伸强度,弹性极限、抗划性、摩擦系数和其它物理性能。
[0038]划擦平台含有金刚石触针、恒定速度的行进样品台阶和安装在平台下方的测量力的变换器。使用安装在触针上的声音变换器鉴定样品微裂开始时的点并感知涂层或基底的破坏。作为行进距离以及有效摩擦的函数对声能、所施加的金刚石力和切线(金刚石牵引)力作图。
[0039]根据力的测量结果,计算“有效摩擦”并作图。在试验的开始部分期间,金刚石在涂层上滑动,因此声音输出低,有效摩擦恒定。当涂层开始微裂时,声音输出增加。外加力、牵引力、有效摩擦或声能的突然增加称为“事件(events)”。“临界事件”是观察到涂层除去时的最早的点和其力的大小是粘附性的量度。这一结论基于随后破损点的显微证明而作出。
[0040]图像的清晰度(DOI)
反射图像的清晰度或DOI是在反射角处反射的光的传播的量化。它给出了被物体反射的图像多么清晰的指示。本发明涂层的DOI评价涉及在油漆过的表面上投影各种尺寸的图像,并测量可清晰地看到多么小的图像。在待检测样品上,在100mm的规定距离处,由荧光发光盒投影成像图案(Landolt环)。将数值100规定为最小组的环,和将数值90、80、70等规定为接下来均匀地增加的较大环,以定量评价油漆过表面的DOI。当从光盒中投影时,使最小环内部清晰可见的涂层规定为等级100(GM9101P,General Motors Engineering Standard)。
热重分析
[0041]使用TA仪器(New Castle,DE)TGA2950,进行热重分析。将约7-12mg单片试样放置在Pt盘内,并在空气氛围中,以10℃/min加热到1000℃,并连续监控和记录重量损失。报道在500℃下重量损失。基于两次分析估计不确定性为±5%。
实施例1-5A和对比例1
[0042]将表2所述的异氰酸酯、醇官能的有机硅树脂(CSR)(下表1所示)、乙酸丁酯溶剂和有机多元醇加入到混合器皿内,并用刮刀剧烈搅拌。在下表2中,BA表示乙酸正丁酯。在抛光的钢板上进行测试。借助6mil(湿)涂膜涂布器施涂配方。使涂布的面板空气干燥15分钟,然后在265下烘箱固化30分钟。所有样品导致具有优良光泽和流动性的膜,例外的是实施例5的膜表面严重皱褶。测量DOI(参见以上的试验说明)并在表3中报道了结果。
表1
CSR | 组合物 |
1 | MPrOH 0.60TPh 0.378 |
2 | MPrOH 0.355TMe 0.314TPh 0.314 |
3 | MPrOH 0.387TPh 0.583 |
4 | MPrOH 0.180TPh 0.793 |
5 | M0.261MPrOH 0.082TPh 0.628 |
6 | MiBuOH 0.310MH 0.052TPh 0.609 |
7 | M苯酚 0.512TMe 0.423 |
8 | MPrOH 0.38TPh 0.41Q0.21 |
9 | MPrOH 0.372TMe 0.415TPh 0.192 |
10 | MPrOH 0.502TMe 0.450 |
Linear 1 | 3-羟丙基封端的聚二甲基硅氧烷 |
在上表1中:
MPrOH表示(HO(CH2)3)(CH3)2SiO1/2
DPrOH表示(HO(CH2)3)(CH3)SiO2/2
MiBuOH表示(HOCH2CH(CH3)CH2)(CH3)2SiO1/2
M苯酚表示(HOC6H4(CH2)3)(CH3)2SiO1/2
D苯酚表示(HOC6H4(CH2)3)(CH3)SiO2/2
M表示(CH3)3SiO1/2
D表示(CH3)2SiO2/2
DPh表示(C6H5)(CH3)SiO2/2
TPh表示C6H5SiO3/2
TMe表示CH3SiO3/2
MH表示(H)(CH3)2SiO1/2
表2
重量(g) | |||||||
组分 | Ex1 | Ex2 | Ex3 | Ex4 | Ex5 | Ex5A | Cex1 |
多元醇:Desmophen870BA | 59.4 | 60.7 | 55.7 | 55.7 | 49.5 | 49.5 | 61.9 |
BA | 9.2 | 7.9 | 11.9 | 12.5 | 20.7 | 21.1 | 12.9 |
CSR4(50%在BA内) | 6.2 | ||||||
CSR5(50%在BA内) | 6.2 | ||||||
CSR3(50%在BA内) | 7.2 | ||||||
CSR2(50%在BA内) | 6.6 | ||||||
CSR1 | 4.6 | ||||||
CSR10 | 4.2 | ||||||
异氰酸酯:DesmodurN-3390 | 25.2 | 25.2 | 25.2 | 25.2 | 25.2 | 25.2 | 25.2 |
总计 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
有机硅树脂wt%(固体) | 4.6 | 4.5 | 5.5 | 5.1 | 7.4 | 6.8 | 0 |
表中Ex-实施例,Cex-对比例,下同。
表3
在裸钢上涂层的图像清晰度(DOI)
Ex1 | Ex2 | Ex3 | Ex4 | Ex5 | Ex5A | Cex1 | |
DOI | 80 | 100 | 100 | 100 | 100 | 50 | 80 |
实施例1-5A和对比例1的总结
[0043]与不具有任何外加有机硅树脂的基础聚氨酯涂层(Cex1)相比,掺入醇官能的有机硅树脂在大多数情况下表明会提高或维持图像的清晰度。
实施例6-15和对比例2
[0044]将下表4所述的异氰酸酯、醇有机硅树脂、乙酸丁酯溶剂和有机多元醇加入到混合器皿内(制备范围为约3-10%Si的配方),并用刮刀剧烈搅拌。
[0045]在配有E-涂层、底漆和黑色头道底漆的钢板(ACTLaboratories;Hillsdale,MI)上进行测试。借助6mil(湿)涂膜涂布器施涂配方。使涂布的面板空气干燥15分钟,然后在265下烘箱固化30分钟。所有样品导致具有优良光泽和流动性的膜。以Kg为单位测量抗划性并在表5中报道了结果。
表4
重量(g) | |||||||||||
组分 | Ex6 | Ex7 | Ex8 | Ex9 | Ex10 | Ex11 | Ex12 | Ex13 | Ex14 | Ex15 | Cex2 |
多元醇:Desmophen870BA | 15.2 | 14.7 | 15.3 | 15.0 | 14.9 | 13.5 | 14.9 | 13.5 | 13.5 | 10.4 | 15.5 |
乙酸正丁酯(BA) | 2.7 | 2.1 | 2.6 | 1.4 | 3.1 | 3.0 | 3.1 | 3.1 | 4.5 | 6.4 | 3.2 |
CSR4(50%在BA内) | 0.8 | 1.9 | |||||||||
CSR5(50%在BA内) | 0.8 | 2.3 | |||||||||
CSR3(50%在BA内) | 0.7 | 2.2 | |||||||||
CSR2(50%在BA内) | 0.7 | 2.1 | |||||||||
CSR1 | 0.7 | 1.9 | |||||||||
异氰酸酯:DesmodurN-3390 | 6.3 | 6.3 | 6.3 | 6.3 | 6.3 | 6.3 | 6.3 | 6.3 | 6.3 | 6.3 | 6.3 |
总计 | 25 | 25 | 25 | 25 | 25 | 25 | 25 | 25 | 25 | 25 | 25 |
有机硅树脂wt%(固体) | 2.3 | 5.7 | 2.3 | 6.7 | 2.2 | 6.9 | 2.0 | 6.4 | 4.5 | 12.7 | 0 |
表5在预涂布的钢上涂层的抗划性(SR)(Kg)
组分 | Ex6 | Ex7 | Ex8 | Ex9 | Ex10 | Ex11 | Ex12 | Ex13 | Ex14 | Ex15 | Cex2 |
SR(Kg) | 2.1 | 1.8 | 1.7 | 1.7 | 2.1 | 1.2 | 1.8 | 1.7 | 1.1 | 2.0 | 1.3 |
实施例6-15和对比例2的总结
[0046]与没有添加任何有机硅树脂的基础聚氨酯涂层相比,掺入醇官能的有机硅树脂表明显著提高抗划性。例外的是,在实施例11和实施例14中,观察到抗划性略微下降。
实施例16-19和对比例3-4
实施例16
[0047]将2.64g醇官能的有机硅树脂6注射到铝盘内。添加2.35gTolonate XIDT 70SB、3.00g乙酸丁酯溶剂和3滴Tegokat218,并在室温下使用木制搅拌棒充分混合各物质。在空气中,在100℃下固化该物质4小时,接着在氮气吹扫的烘箱中,在200℃下后固化1小时。所得物质是坚韧的无色透明固体。在空气中,通过热重分析法分析固化的硅氧烷-聚氨酯混杂材料,并在表6中示出了结果。
实施例17
[0048]将4.16g醇官能的有机硅树脂6注射到铝盘内。添加2.36gDesmodur N-3390、3.00g乙酸丁酯溶剂和3滴Tegokat218,并在室温下使用木制搅拌棒充分混合各物质。在空气中,在100℃下固化该物质4小时,接着在氮气吹扫的烘箱中,在200℃下后固化1小时。所得物质是坚韧的、弹性、半透明的固体。在空气中,通过热重分析法分析固化的硅氧烷-聚氨酯混杂材料,并在表6中示出了结果。
实施例18
[0049]将0.88g醇官能的有机硅树脂7注射到铝盘内。添加2.35gTolonate XIDT 70SB、2.96g乙酸丁酯溶剂和3滴Tegokat218,并在室温下使用木制搅拌棒充分混合各物质。在空气中,在100℃下固化该物质4小时,接着在氮气吹扫的烘箱中,在200℃下后固化1小时。所得物质是坚韧的、略微棕褐色的透明固体。在空气中,通过热重分析法分析固化的硅氧烷-聚氨酯混杂材料,并在表6中示出了结果。
实施例19
[0050]将1.26g醇官能的有机硅树脂6注射到铝盘内。添加2.37gDesmodur N-3390、4.08g Desmophen870BA、2.96g乙酸丁酯溶剂和3滴Tegokat218,并在室温下使用木制搅拌棒充分混合各物质。在空气中,在100℃下固化该物质4小时,接着在氮气吹扫的烘箱中,在200℃下后固化1小时。所得物质是坚韧的、硬质、略微混浊的固体。在空气中,通过热重分析法分析固化的硅氧烷-聚氨酯混杂材料,并在表6中示出了结果。
对比例3
[0051]将5.76g Desmophen870BA注射到铝盘内。添加3.76gTolonate XIDT 70SB、2.96g乙酸丁酯溶剂和3滴Tegokat218,并在室温下使用木制搅拌棒充分混合各物质。在空气中,在100℃下固化该物质4小时,接着在氮气吹扫的烘箱中,在200℃下后固化1小时。所得物质是硬质、发脆的略微混浊的固体。在空气中,通过热重分析法分析固化的聚氨酯材料,并在表6中示出了结果。
对比例4
[0052]将5.78g多元醇Desmophen870BA注射到铝盘内。添加2.35g Desmodur N-3390、2.96g乙酸丁酯溶剂和3滴Tegokat218,并在室温下使用木制搅拌棒充分混合各物质。在空气中,在100℃下固化该物质4小时,接着在氮气吹扫的烘箱中,在200℃下后固化1小时。所得物质是坚韧、硬质的略微混浊的固体。在空气中,通过热重分析法分析固化的聚氨酯材料,并在表6中示出了结果。
表6
成分 | Ex16 | Ex17 | Ex18 | Ex19 | Cex3 | Cex4 |
Desmophen870BA | 4.08g | 5.76g | 5.78g | |||
Desmodur N-3390 | 2.36g | 2.37g | 2.35g | |||
Tolonate XIDT 70SB | 2.35g | 2.35g | 3.76g | |||
CSR 6 | 2.64g | 4.16g | 1.26g | |||
CSR 7 | 0.88g | |||||
乙酸丁酯 | 3.00g | 3.00g | 2.96g | 2.96g | 2.96g | 2.96g |
二月桂酸二丁锡催化剂 | 3滴 | 3滴 | 3滴 | 3滴 | 3滴 | 3滴 |
TGA结果500℃的重量损失%(空气中) | 58.1 | 51.9 | 79.1 | 83.2 | 91.8 | 95.9 |
总结
[0053]实施例16-19表明,在聚氨酯材料中使用醇官能的有机硅树脂作为部分或全部有机多元醇的替代物会提高所得热固性材料的热稳定性(与对照的Cex3和Cex4相比)。
实施例20-25A和对比例5-6
[0054]多元醇:Desmophen870BA是由Bayer Corporation(Pittsburgh,PA)供应的在乙酸丁酯内的羟基官能的聚丙烯酸酯树脂(70%固体)。
异氰酸酯:Desmodur N-3390是由BayerCorporation(Pittsburgh,PA)供应的在乙酸丁酯内的基于六亚甲基二异氰酸酯(HDI)的聚异氰酸酯(90%固体)。
BA:乙酸正丁酯
[0055]再涂布性:相对于具体的涂料配方,规定这一试验的条件(施涂方法,膜厚和固化方案)。在起始固化之后,用相同的油漆配方和对照涂料罩面涂布该样品。在固化该面漆之后,就该第二涂层润湿下面膜的能力评定面板。
5-优良的润湿和流动,没有膜缺陷,例如缩孔和鱼眼
4-轻微的去润湿和/或边缘收缩;最小的缺陷
3-适中的去润湿和/或边缘收缩;最小的缺陷
2-大量的去润湿和/或边缘收缩;少数缺陷
1-大量的去润湿和/或边缘收缩;许多缺陷
0-严重的去润湿和/或边缘收缩;大量的缺陷
[0056]将上述异氰酸酯,上述多元醇,上表1中制备的醇官能的有机硅树脂之一(CSR),和乙酸正丁酯(溶剂)加入到混合器皿中,并采用刮刀剧烈地搅拌。在抛光的钢板上进行试验。借助6mil(湿)涂膜涂布器施涂该配方。使涂布的面板空气干燥15分钟,然后在265下烘箱固化30分钟。评价固化膜的外观,其中1=差和5=优良,和表7记录了这些数值。
[0057]然后,采用相同配方,垂直于起始涂层涂布固化膜,并固化与第一涂层相同的新涂层(空气干燥15分钟,然后在265下烘箱固化30分钟)。表7中评价并记录了每一配方的再涂布性。
表7涂料配方(重量g) | ||||||||||
组分 | Cex5 | Ex20 | Ex21 | Ex22 | Ex23 | Ex24 | Ex25 | Ex25A | Cex6 | 在CSR或Linear1内的苯基wt% |
多元醇 | 15.5 | 11.4 | 12.5 | 12.7 | 14.2 | 13.2 | 12.2 | 11.1 | 13.5 | |
BA | 3.2 | 3.2 | 3.2 | 3.2 | 3.2 | 2.7 | 3.2 | 3.2 | 3.2 | |
CSR4 | 1.5 | 35.3 | ||||||||
CSR5 | 1.6 | 40.0 | ||||||||
CSR6 | 1.6 | 56.6 | ||||||||
CSR7 | 1.7 | 62.2 | ||||||||
CSR8 | 2.2 | 48.3 | ||||||||
CSR9 | 1.6 | 34 | ||||||||
CSR10 | 1.5 | 0 | ||||||||
Linear 1 | 1.7 | 0 | ||||||||
异氰酸酯:DesmodurN-3390 | 6.3 | 6.3 | 6.3 | 6.3 | 6.3 | 6.3 | 6.3 | 6.3 | 6.3 | |
总计 | 25 | 22 | 24 | 24 | 25 | 24 | 23 | 22 | 25 | |
有机硅树脂wt%(固体) | 0 | 10 | 10 | 10 | 10 | 10 | 10 | 10 | 10 | |
起始涂层质量1=差5=完美 | 3 | 4 | 1* | 4 | 3 | 3 | 1** | 1** | 1^ | |
再涂布性1=差5=完美 | 2 | 4 | 2 | 4 | 3 | 3 | 2 | 1 | 1 |
*表示桔皮缺陷
**表示严重的桔皮缺陷
^表示均匀但非常混浊
总结
[0058]含有具有所列苯基的醇官能的有机硅树脂(CSR)的涂层显示出与没有添加硅氧烷的Cex5一样好或者更好的起始涂层质量和再涂布性。对比例Cex6,含有直链醇官能的硅氧烷的涂层显示出差的起始膜质量和再涂布性。
实施例26-29和对比例7
[0059]在聚氨酯泡沫体配方内的醇官能的有机硅树脂
材料:
OPTIMAH2O(Fisher Scientific,Fair Lawn,NJ)
DABCO33LV-含有33%三亚乙基二胺和67%二丙二醇的胶凝催化剂,其获自Air Products and Chemicals,Inc.,Allentown,PA。
DABCOBL-11-含有70%双(二甲基氨基乙基)醚和30%二丙二醇的发泡催化剂,其获自Air Products andChemicals,Inc.,Allentown,PA。
DABCOT-12-含有二月桂酸二丁锡的强胶凝催化剂,其获自AirProducts and Chemicals,Inc.,Allentown,PA。
VORANOL3512A-分子量为约3500的甘油为起始的聚醚多元醇,其获自Dow Chemical Company,Midlad,MI。
TDI-甲苯二异氰酸酯,获自Bayer,Pittsburgh,PA。
DABCODC5982表面活性剂-分散在多元醇内的硅氧烷二元醇共聚物,其获自Dow Corning Corporation,Midlad,MI。
二氯甲烷,获自Fisher Scientific,Fair Lawn,NJ。
方法:
热重分析
[0060]
使用TA仪器(New Castle,DE)TGA2950,进行热重分析。将约7-12mg单片试样放置在Pt盘内,并在独立的试验中,在空气和氮气氛围下,以10℃/min加热到1000℃,并连续监控和记录重量损失。报道在200℃和350℃下的重量损失。基于两次分析估计不确定性为±5%。
对比例7
[0061]称量150.05g VORANOL3512A、5.25g OPT IMAH2O、0.23gDABCO33LV和0.07g DABCOBL-11放入纸料斗中,并在高速下混合30秒。接下来,将0.75g DABCODC5982表面活性剂、0.30gDABCOT-12和22.5g二氯甲烷加入到该料斗中,在中等速度下混合内容物10秒。然后将71.0g甲苯二异氰酸酯加入到料斗内,并在高速下混合内容物5秒。使泡沫上升,并使泡沫体在室温下固化10分钟。最后,将泡沫体放置在200烘箱中20分钟。从烘箱中取出固化的泡沫体,并立即测量高度,且完成热重分析,表8报道了结果。
实施例26
[0062]称量135.05g VORANOL3512A、12.96g来自上表1的CSR5、5.25g OPTIMAH2O、0.23g DABCO33LV和0.07g DABCOBL-11放入纸料斗中,并在高速下混合30秒。接下来,将0.75g DABCODC5982表面活性剂、0.30g DABCOT-12和22.5g二氯甲烷加入到该料斗中,在中等速度下混合内容物10秒。然后将71.0g甲苯二异氰酸酯加入到料斗内,并在高速下混合内容物5秒。使泡沫上升,并使泡沫体在室温下固化10分钟。最后,将泡沫体放置在200烘箱中20分钟。从烘箱中取出固化的泡沫体,并立即测量高度,且完成热重分析,表8报道了结果。
实施例27
[0063]称量90.03g VORANOL3512A、51.84g来自上表1的CSR5、5.25g OPTIMAH2O、0.23g DABCO33LV和0.07g DABCOBL-11放入纸料斗中,并在高速下混合30秒。接下来,将0.75g DABCODC5982表面活性剂、0.30g DABCOT-12和22.5g二氯甲烷加入到该料斗中,在中等速度下混合内容物10秒。然后将71.0g甲苯二异氰酸酯加入到料斗内,并在高速下混合内容物5秒。使泡沫上升,并使泡沫体在室温下固化10分钟。最后,将泡沫体放置在200烘箱中20分钟。从烘箱中取出固化的泡沫体,并立即测量高度,且完成热重分析,表8报道了结果。
实施例28
[0064]称量135.05g VORANOL3512A、14.02g来自上表1的CSR6、5.25g OPTIMAH2O、0.23g DABCO33LV和0.07g DABCOBL-11放入纸料斗中,并在高速下混合30秒。接下来,将0.75g DABCODC5982表面活性剂、0.30g DABCOT-12和22.5g二氯甲烷加入到该料斗中,在中等速度下混合内容物10秒。然后将71.0g甲苯二异氰酸酯加入到料斗内,并在高速下混合内容物5秒。使泡沫上升,并使泡沫体在室温下固化10分钟。最后,将泡沫体放置在200烘箱中20分钟。从烘箱中取出固化的泡沫体,并立即测量高度,且完成热重分析,表8报道了结果。
实施例29
[0065]称量90.03g VORANOL3512A、56.09g来自上表1的CSR6、5.25g OPTIMAH2O、0.23g DABCO33LV和0.07g DABCOBL-11放入纸料斗中,并在高速下混合30秒。接下来,将0.75g DABCODC5982表面活性剂、0.30g DABCOT-12和22.5g二氯甲烷加入到该料斗中,在中等速度下混合内容物10秒。然后将71.0g甲苯二异氰酸酯加入到料斗内,并在高速下混合内容物5秒。使泡沫上升,并使泡沫体在室温下固化10分钟。最后,将泡沫体放置在200烘箱中20分钟。从烘箱中取出固化的泡沫体,并立即测量高度,且完成热重分析,表8报道了结果。
表8
Cex7 | Ex26 | Ex27 | Ex28 | Ex29 | |
有机硅树脂wt%(固体) | 0 | 5.9 | 24.4 | 6.4 | 25.9 |
泡沫高度(mm) | 416.67 | 422.66 | 309.67 | 431.37 | 382.88 |
空气中200℃下的重量损失(%) | 1.55 | 1.03 | 1.87 | 0.10 | 0.53 |
空气中350℃下的重量损失(%) | 93.34 | 87.30 | 82.70 | 87.08 | 78.40 |
氮气中200℃下的重量损失(%) | 2.37 | 0.98 | 2.22 | 0.98 | 1.13 |
氮气中350℃下的重量损失(%) | 59.39 | 51.34 | 52.21 | 47.80 | 53.47 |
总结
[0066]表8示出了添加醇官能的有机硅树脂到聚氨酯泡沫体配方中降低了在空气和氮气环境内所得泡沫体的重量损失,同时维持与对照物相比类似的泡沫高度。
实施例30和对比例8-10
[0067]材料:
三羟甲基丙烷单烯丙醚(Sigma-Aldrich Chemical Co.,MilwaukeeWI DOW CORNING 6-3570聚合物(三甲基甲硅烷基封端的二甲基甲硅烷氧基/甲基氢甲硅烷氧基共聚物)(Dow Corning,Midland,MI))。
三苯基膦(Sigma-Aldrich Chemical Co.,Milwaukee WI)烯丙醇(Sigma-Aldrich Chemical Co.,Milwaukee WI)FC-24-三氟甲磺酸,获自3M,St.,Paul,Minn.。
方法:
60°光泽
[0068](ASTM D523-89)通过比较来自样品与来自黑色玻璃标准物的镜面反射,获得所测量的光泽等级。采用60°光泽来比较各样品。使用Gloss仪(BYK-Gardner Micro-Tri-gloss,目录号#4522)进行试验。在涂层表面上取最少5次读数,并报道平均值。
[0069]合成两种对比的醇官能的直链聚硅氧烷和醇官能的有机硅树脂,并使用Desmodur N-3390异氰酸酯和Desmophen 870BA多元醇(以提供1∶1的异氰酸酯∶醇的化学计量比)和乙酸丁酯作为稀释溶剂,在9.3wt%的负载下,配制成聚氨酯涂料配方,和表9描述了该配方的细节。另外,制备不含硅氧烷的聚氨酯涂料。使用6mil的涂膜涂布器,将该配方施涂到3″×6″和3″×9″的丙酮脱脂的铝盘上。使涂布的面板空气干燥15分钟,然后在265下烘箱固化30分钟。评价涂布面板的涂层质量,图像清晰度和60°光泽,并在表9中记录了结果。
[0070]如下所述制备实施例30中所使用的醇官能的树脂(CSR30):将水(282.1g)加入到甲基三甲氧基硅烷(858.5g)、苯基三甲氧基硅烷(1249.4g)和三氟甲磺酸(1.05g)的混合物中。在蒸馏除去副产物醇之后,添加甲苯(1368.1g)、四甲基二硅氧烷(435.2g)和乙酸(195.1g)。在50-55℃下加热3小时之后,借助蒸馏除去挥发物,直到反应混合物为80℃。添加甲苯(370.9g)并用水和含水碳酸氢钠洗涤混合物,然后借助共沸蒸馏干燥到约60wt%的浓度。添加烯丙醇(846.8g)。在加热到88℃之后,添加1%Pt/Al2O3(1.53g),并在回流下加热混合物约6小时。添加三苯基膦(0.061g)和脱色碳(3.0g),过滤该混合物,并真空除去挥发物,然后在乙酸丁酯内再溶解成约76wt%的浓度。通过29SiNMR测定所得树脂结构为MPrOH 0.32TMe 0.35TPh 0.33,且基于固体,醇当量为355。
[0071]如下所述制备对比例8(Cex8)中所使用的对比的直链醇官能的聚硅氧烷(Linear2):将铂的二乙烯基四甲基二硅氧烷络合物的甲苯溶液(0.53g 4810ppm的Pt溶液)加入到5cSt 0.76wt%反应性氢(Si-H形式)的三甲基甲硅烷基封端的二甲基甲硅烷氧基/甲基氢甲硅烷氧基共聚物(5.0g)(其以6-3750 Polymer形式获自DowCorning(Midland,MI))和烯丙醇(155.2g)的加热的(65℃)的混合物中,接着另外添加95.0g该共聚物。在≥75℃下保持该混合物30分钟,然后添加三苯基膦(0.0153g)。过滤该混合物并真空除去挥发物。所得材料是不具有RSiO3/2单元且醇当量为249的直链醇硅氧烷低聚物。
[0072]如下所述制备对比例9(Cex9)中所使用的对比的直链醇官能的聚硅氧烷(Linear3):将铂的二乙烯基四甲基二硅氧烷络合物的甲苯溶液(0.56g 4810ppm的Pt溶液)加入到5cSt 0.76wt%反应性氢(Si-H形式)的三甲基甲硅烷基封端的二甲基甲硅烷氧基/甲基氢甲硅烷氧基共聚物(5.03g)(其以6-3750 Polymer形式获自DowCorning(Midland,MI))和三羟甲基丙烷单烯丙醚(170.84g)的加热的(80℃)的混合物中,接着另外添加95.22g该共聚物。在≥85℃下保持该混合物约10分钟,所得材料是不具有RSiO3/2单元且醇当量为169的直链醇硅氧烷低聚物。使用如前所述的有机异氰酸酯(DesmodurN-3390)和有机多元醇(Desmophen 870BA),制备对比例10(Cex10)的涂层。
表9涂料配方(重量g) | ||||
组分 | Ex30 | Cex8 | Cex9 | Cex10 |
Desmophen 870BA | 1.94 | 2.10 | 2.26 | 1.90 |
CSR30(76%在BA内) | 0.71 | |||
Linear 2 | 0.55 | |||
Linear 3 | 0.55 | |||
异氰酸酯:Desmodur N-3390 | 4.35 | 4.36 | 4.19 | 5.10 |
醇有机硅树脂或Linear wt%(固体) | 9.3 | 9.3 | 9.3 | 0 |
起始涂层质量1=差5=完美 | 5 | 3^ | 1* | 4 |
图像清晰度 | 90 | 60 | 10 | 80 |
60°光泽 | 131.2 | 124.3 | 97.4 | 131.3 |
^表示均匀但混浊
*表示桔皮缺陷
实施例30和对比例8-10的总结
[0073]根据表9,结果表明,具有含RSiO3/2单元的醇官能的有机硅树脂的配方提供硅氧烷改性的聚氨酯涂层,且相对于没有添加硅氧烷的聚氨酯体系(Cex10)以及掺入直链硅氧烷的聚氨酯体系(Cex8-9),就起始涂层质量、图像的清晰度和光泽来说,没有降低膜的质量。这使得涂料配制者能掺入具有外加耐热性的硅氧烷(参见实施例16-19)到聚氨酯涂层内,且没有降低外观特征。
Claims (15)
1.一种聚氨酯组合物,它包括:(A)含至少一个异氰酸酯基的至少一种化合物;(B)含下述单元的醇官能的有机硅树脂:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1和R2各自独立地为氢原子、具有1-8个碳原子的烷基、芳基、具有至少3个碳原子的不含芳基的醇基,或者具有至少6个碳原子的含芳基的醇基,R3是具有1-8个碳原子的烷基,或芳基,a的数值小于或等于0.6,b的数值为0或大于0,c的数值大于0,d的数值小于0.5,和a+b+c+d=1,和条件是当每一R2是甲基时,b的数值小于0.3;其中醇基与异氰酸酯基的摩尔比为约0.8∶1到1.2∶1。
2.一种聚氨酯组合物,它包括:(A)100重量份含至少一个异氰酸酯基的至少一种化合物;(B)3-300重量份含下述单元的醇官能的有机硅树脂:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1和R2各自独立地为氢原子、具有1-8个碳原子的烷基、芳基、具有至少3个碳原子的不含芳基的醇基,或者具有至少6个碳原子的含芳基的醇基,R3是具有1-8个碳原子的烷基,或芳基,a的数值小于或等于0.6,b为0或大于0,c的数值大于0,d的数值小于0.5,和a+b+c+d=1,和条件是当每一R2是甲基时,b的数值小于0.3,和(C)最多250重量份有机多元醇;和(D)最多10重量份固化速率改进剂。
3.一种聚氨酯组合物,它包括:(A)100重量份含至少一个异氰酸酯基的至少一种化合物;(B)0.3-300重量份含下述单元的醇官能的有机硅树脂:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1和R2各自独立地为氢原子、具有1-8个碳原子的烷基、芳基、具有至少3个碳原子的不含芳基的醇基,或者具有至少6个碳原子的含芳基的醇基,R3是具有1-8个碳原子的烷基,或芳基,a的数值小于或等于0.6,b的数值为0或大于0,c的数值大于0,d的数值小于0.5,和a+b+c+d=1,和条件是当每一R2是甲基时,b的数值小于0.3,和条件是每一树脂分子平均具有至少一个醇基;(C)最多250重量份有机多元醇;和(D)最多10重量份固化速率改进剂,其中醇基与异氰酸酯基的摩尔比为约0.8∶1到1.2∶1。
4.一种聚氨酯组合物,它通过包括下述步骤的方法而获得:使(A)含至少一个异氰酸酯基的至少一种化合物;和(B)含下述单元的醇官能的有机硅树脂反应:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1和R2各自独立地为氢原子、具有1-8个碳原子的烷基、芳基、具有至少3个碳原子的不含芳基的醇基,或者具有至少6个碳原子的含芳基的醇基,R3是具有1-8个碳原子的烷基,或芳基,a的数值小于或等于0.6,b的数值为0或大于0,c的数值大于0,d的数值小于0.5,和a+b+c+d=1,和条件是当每一R2是甲基时,b的数值小于0.3,其中醇基与异氰酸酯基的摩尔比为约0.8∶1到1.2∶1。
5.一种聚氨酯组合物,它通过包括下述步骤的方法而获得:使(A)100重量份含至少一个异氰酸酯基的至少一种化合物;(B)3-300重量份含下述单元的醇官能的有机硅树脂:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1和R2各自独立地为氢原子、具有1-8个碳原子的烷基、芳基、具有至少3个碳原子的不含芳基的醇基,或者具有至少6个碳原子的含芳基的醇基,R3是具有1-8个碳原子的烷基,或芳基,a的数值小于或等于0.6,b的数值为0或大于0,c的数值大于0,d的数值小于0.5,和a+b+c+d=1,和条件是当每一R2是甲基时,b的数值小于0.3;(C)最多250重量份有机多元醇;和(D)最多10重量份固化速率改进剂反应。
6.一种聚氨酯组合物,它通过包括下述步骤的方法而获得:使(A)100重量份含至少一个异氰酸酯基的至少一种化合物;(B)0.3-300重量份含下述单元的醇官能的有机硅树脂:
(R1 3SiO1/2)a (i)
(R2 2SiO2/2)b (ii)
(R3SiO3/2)c (iii)和
(SiO4/2)d (iv)
其中R1和R2各自独立地为氢原子、具有1-8个碳原子的烷基、芳基、具有至少3个碳原子的不含芳基的醇基,或者具有至少6个碳原子的含芳基的醇基,R3是具有1-8个碳原子的烷基,或芳基,a的数值小于或等于0.6,b的数值为0或大于0,c的数值大于0,d的数值小于0.5,和a+b+c+d=1,和条件是当每一R2是甲基时,b的数值小于0.3,和条件是每一树脂分子平均具有至少一个醇基;(C)最多250重量份有机多元醇;和(D)最多10重量份固化速率改进剂反应,其中醇基与异氰酸酯基的摩尔比为约0.8∶1到1.2∶1。
7.权利要求1或4的聚氨酯组合物,进一步包括(C)有机多元醇。
8.权利要求1、4和7任何一项的聚氨酯组合物,进一步包括(D)固化速率改进剂。
9.权利要求1-8任何一项的聚氨酯组合物,其中:
烷基是甲基;
芳基是苯基;
具有至少3个碳原子的不含芳基的醇基选自通式为R4OH的基团,其中R4选自:
(1)通式为-(CH2)x-的基团,其中x的数值为3-10,
(2)-CH2CH(CH3)-,
(3)-CH2CH(CH3)CH2-,
(4)-CH2CH2CH(CH2CH3)CH2CH2CH2-,和
(5)通式为-OCH(CH3)(CH2)x-的基团,其中x的数值为1-10,和通式为R6(OH)的基团,其中R6是通式为-CH2CH2(CH2)xOCH2CH-的基团,其中在每一情况下,x的数值为1-10;
具有至少6个碳原子的含芳基的醇基是通式为R5OH的基团,其中R5选自:
(1)通式为-(CH2)xC6H4-的基团,其中x的数值为0-10,
(2)通式为-CH2CH(CH3)(CH2)xC6H4-的基团,其中x的数值为0-10,
(3)通式为-(CH2)xC6H4(CH2)x-的基团,其中x的数值为1-10。
10.权利要求1-9任何一项的聚氨酯组合物,其中a的典型数值为0.1-0.6,b的典型数值为0-0.4,c的典型数值为0.3-0.8,和d的典型数值为0-0.3。
11.权利要求1-8任何一项的聚氨酯组合物,其中醇官能的有机硅树脂选自:
含下述单元的醇官能的有机硅树脂:
((CH3)3SiO1/2)a
((R2)CH3SiO2/2)b,其中R2=-(CH2)3C6H4OH
(C6H5)CH3SiO2/2)b,和
(C6H5SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((R1)(CH3)2SiO1/2)a,其中R1=-(CH2)3C6H4OH和
(C6H5SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((R1)(CH3)2SiO1/2)a,其中R1=-(CH2)3C6H4OH和
(CH3SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((R1)(CH3)2SiO1/2)a,其中R1=-(CH2)3OH和
(C6H5SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((R1)(CH3)2SiO1/2)a,其中R1=-(CH2)3OH和
(CH3SiO3/2)c和
(C6H5SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((CH3)3SiO1/2)a,
((R2)CH3SiO2/2)b,其中R2=-(CH2)3OH
((C6H5)CH3SiO2/2)b和
(C6H5SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((CH3)3SiO1/2)a,
((R1)(CH3)2SiO1/2)a,其中R1=-(CH2)3OH和
(C6H5SiO3/2)c,
含下述单元的醇官能的有机硅树脂:
((R1)(CH3)2SiO1/2)a,其中R1=-CH2CH(CH3)CH2OH
((H)(CH3)2SiO1/2)a和
(C6H5SiO3/2)c,以及
含下述单元的醇官能的有机硅树脂:
((R1)(CH3)2SiO1/2)a,其中R1=-(CH2)3OH
(CH3SiO3/2)c,
其中a的典型数值为0.1-0.6,b的典型数值为0-0.4,和c的典型数值为0.3-0.8。
12.权利要求1-11任何一项的聚氨酯组合物,其中大于10wt%的R1+R2+R3基是苯基。
13.权利要求1-12任何一项的聚氨酯组合物,其中该聚氨酯组合物进一步包括选自填料、溶剂、增塑剂、颜料、着色剂、染料、表面活性剂、增稠剂、热稳定剂、流平剂、防堵孔剂、填料、沉降抑制剂、紫外光吸收剂、促进剂、热稳定剂、紫外光吸收剂和抗氧剂中的至少一种成分。
14.权利要求1-13任何一项的聚氨酯组合物,其中聚氨酯组合物进一步包括至少一种泡孔稳定剂和至少一种发泡剂,和任选的增链剂和交联剂。
15.权利要求14的聚氨酯组合物,其中泡孔稳定剂是硅氧烷聚醚和发泡剂选自水、液体二氧化碳、CFC、HCFC、HFC和戊烷。
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JP4939221B2 (ja) | 2012-05-23 |
WO2005037887A1 (en) | 2005-04-28 |
EP1678234A1 (en) | 2006-07-12 |
US20070093618A1 (en) | 2007-04-26 |
US7452956B2 (en) | 2008-11-18 |
ATE534686T1 (de) | 2011-12-15 |
JP2007508425A (ja) | 2007-04-05 |
EP1678234B1 (en) | 2011-11-23 |
CN100556929C (zh) | 2009-11-04 |
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