CN102834446A - 聚氨酯泡沫烧焦抑制剂 - Google Patents

聚氨酯泡沫烧焦抑制剂 Download PDF

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CN102834446A
CN102834446A CN2010800654710A CN201080065471A CN102834446A CN 102834446 A CN102834446 A CN 102834446A CN 2010800654710 A CN2010800654710 A CN 2010800654710A CN 201080065471 A CN201080065471 A CN 201080065471A CN 102834446 A CN102834446 A CN 102834446A
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约翰·M·德马萨
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Vanderbilt Minerals Ltd
Vanderbilt Chemicals LLC
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Abstract

用于聚氨酯泡沫的烧焦抑制剂组合物由下列组成：(a)约60%至80%重量比的一种或多种衍生的酚类化合物；(b)约15%至35%重量比的一种或多种液态形式的芳香胺；(c)约4%至8%重量比的烷基取代的对苯二酚，以及(d)0%至约1.0%重量比的吩噻嗪。

Description

聚氨酯泡沫烧焦抑制剂
发明背景 
发明领域
本发明涉及用于聚氨酯泡沫组合物的液态烧焦抑制剂组合物。 
现有技术的讨论 
熟悉软质聚氨酯块状型泡沫制造的人已经观察到称为烧焦的现象，其表现为聚合物降解。在外表上，烧焦表现为聚氨酯泡沫块(bun)内部变黑，其可以以色相、明度以及彩度来定量表征。烧焦是已得到充分了解的热氧化降解过程，其通常是涉及泡沫内的聚氨酯基质、聚醚多醇、异氰酸酯(MDI或TDI)以及添加剂的自由基反应的结果。例如，在升高的温度(200°C,392°F)下，基于4,4’-二苯基甲烷二异氰酸酯的热塑性聚氨酯弹性体具有主链断裂的缺点。也已知热引起其他均裂降解过程，如从α碳向醚键的氢原子争夺。所产生的自由基与氧结合，导致氢过氧化物物质的产生，这进一步分裂并传导降解。预期地，基于聚环氧丙烷乙二醇的多元醇不如基于聚乙二醇的那些多元醇稳定，这是由于α碳自由基的稳定性差异所致。因此，烧焦降解遵循得到充分了解的反应途径。在历史上CFC已经用于泡沫制剂来除去过量发热，并由此减少烧焦作用。然而，由于氯氟化碳(CFC)的减少，并且最近过渡型氢氯氟化碳(HCFC)的减少，加上水的增加以补偿(高达6pph)泡沫制剂，烧焦一直是工业的巨大担忧。 
为了抵抗烧焦或者破坏性自由基反应，添加抗氧化剂。专利文献的综述表明了抗氧化剂制剂策略的多样性。 
Baxter的第T968,002号美国防御性公开教导了产生功能性烧焦抑制剂的芳香胺、对苯二酚(下述结构1)以及亚磷酸盐的混合物。Preston的第4,010,211号美国专利公开了有效量的所选二苯胺衍生物单独或还与对苯二酚组合的用途，对苯二酚的作用是抑制聚氨酯泡沫的烧焦。DeMassa 的第6,676,849号美国专利教导了叔-戊基-对苯二酚与商业酚醛树脂的混合物。因此，对苯二酚和衍生物已经用于各种烧焦抑制剂混合物中。 
目前商业上可获得的常规组合物遵循Hinze的第4,275,173号美国专利和Statton的第4,444,676号美国专利的教导，但是基于该主旨其他混合物也出现改变。Suhoza的第4,933,374号美国专利报到了相似的有效烧焦抑制剂混合物，其由以下组成：(a)四[亚甲基(3,5-二-叔丁基-4-羟基氢化肉桂酸酯)]甲烷和(b)二苯胺与二异丁烯的反应产物，其中胺与二异丁烯的摩尔比是1:1.1至1:2.5。稳定剂组合物可以含有第三种协同组分，即吩噻嗪或吩噻嗪的某些烷基衍生物。 
我们已经发现，由如下组成的液态混合物作为聚氨酯泡沫的烧焦抑制剂组合物令人惊奇地优于上文所讨论的混合物： 
(a)一种或多种衍生的酚类化合物 
(b)一种或多种液态形式的芳香胺 
(c)取代的对苯二酚，以及 
(d)任选地，吩噻嗪。 
本发明的详细描述 
用标准的聚氨酯泡沫制剂(表A)检测典型的烧焦抑制剂混合物。也可以使用其他已知的泡沫制剂： 
表A 
    份
  多元醇   100.00
[0018] 
  蒸馏水   5.50
  L5770硅酮(OSi)   1.20
  A127胺催化剂(OSi)   0.47
  Fyrol FR2(Akzo/Nobel)   7.00
  Dabco T9(Air Products)   0.25
  Mondur TD80 Grade A TDI(Bayer AG)   70.80
  添加剂   0.50
本发明烧焦抑制剂的实施方案是多组分液态体系，其包含(重量%计)： 
(1)约60%至80%重量比的酚类化合物或混合物。可接受的衍生的酚醛树脂的实例包括：四[亚甲基(3,5-二-叔-丁基-4-羟基氢化肉桂酸酯)]甲烷、异-辛基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯、异十三烷基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯和2,6二-叔-丁基-4-壬基苯酚或1,2-双(3,5-二-叔-丁基-4-羟基氢化肉桂酰)肼或2,2’-硫代二亚乙基双[3-(3,5-二-t-丁基-4-羟苯基)丙酸酯；i-辛基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯；以及四[亚甲基3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯]甲烷。衍生的酚醛树脂的其他实例包括在第4位被脂肪族、芳香族或脂肪族-芳香族部分取代的且还任选具有诸如O、N、S以及P的杂原子的组合的(2,6-二-叔-丁基)苯酚。 
在本发明优选的实施方案中，酚组分以：(i)四[亚甲基(3,5-二-叔-丁基-4-羟基氢化肉桂酸酯)]甲烷(“酚1”);(ii)异-辛基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯(“酚2”)；以及(iii)异十三烷基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯(“酚3”)的组合中的一种或多种的形式存在。 
(2)约15%至35%的形成液体的芳香胺，即二烷基二苯基胺或这类芳香胺的混合物，(例如二异丁烯与二苯胺的反应产物，CAS登记号68411-46-1)(“DPA”)。其他芳香胺包括4,4’-二(α,α-二甲基苄基)二苯胺(“DPA2”)等。 
(3)约4%至8%的烷基取代的对苯二酚，例如2,5-二-叔-戊基-对苯二酚(“DTAHQ”)或二-叔-丁基-对苯二酚(“DTBHQ”)，其中最有效的烷基是叔丁基(C4)或异戊基(C5)。 
(4)任选地，0%至1%、优选约0.7%的吩噻嗪(PTZ)。 
烧焦抑制剂可以存在于泡沫制剂中，其范围为每100份多元醇约 0.10-0.75份，优选约0.30-0.60份，更优选约0.35-0.50份。 
数据的定量处理 
用Technidyne Corp.Brightimeter Micro S4-M定量泡沫样品的显色。将来自Hunter L.a.b评定表的L.a.b.值赋予每个变量(亮度(L)、a、b)相应的维度(x,y,z)并产生颜色空间。从样品获取的L.a.b.读数表示与个体泡沫最亮的未烧焦区的颜色离差。在实践中，首先从对照获得L.a.b.读数，并将[(L1,a1,b1)或(L,a,b)1]与个体样品[(L2,a2,b2)或(L,a,b)2]比较。随后报道ΔE值。 
ΔE = ( L 1 - L 2 ) 2 + ( a 1 - a 2 ) 2 + ( b 1 - b 2 ) 2
(L.a.b.)1表示由任意标准或对照获得的值，而(L.a.b.)2表示针对所选样品的值。合成值ΔE定量地表示离开对照的颜色漂移。(有人可能认为ΔE是三维空间的距离公式。因此，利用这种公式测量三维空间中任意两点的距离)。重要的是，ΔE值仅仅是与对照的绝对距离，对于我们而言，其代表从目标泡沫未烧焦区最白部分的变色。因为泡沫的产生逐日地高度依赖ΔE值的环境因素变化。为了标准化所报告的值，我们通常运行与检测泡沫同一天的对照(Ex.K)。随后用检测泡沫ΔE值除以对照ΔE并进行报告。对于具体检验日，该比值有助于一览相对于对照的局部色差。如果合适，我们报道比较ΔE值，而不进行这种标准化程序。 
其他评估 
使本专利所提出的制剂进行微波烧焦检测。在反应后允许所得的泡沫块冷却，并裂开，以进行目视检查。我们将每个制剂与同一天运行的对照(含有常规烧焦抑制剂)进行比较。除了烧焦检测外，我们还发现，当在通风柜和外界荧光下将泡沫暴露于NOx处理时，与对照相比，请求保护的制剂表现良好。我们还发现，新制剂表现出了比常规混合物更低的挥发性，对于用于汽车内饰的PU泡沫而言，这是重要的性能参数。我们的观点是，下文所述的本发明的液态制剂的独特性归因于在各种负荷检测中其比常规混合物更好的烧焦保护性和更低的泡沫变色。 
将根据本发明实施方案的示例性混合物(实施例1-10)(表1)与竞争性混合物(实例C13-C17)(表2)进行比较。在5000ppm(或0.5pph)时，发现本发明的混合物对烧焦的抑制比下述下列比较实例更好：比较实例C13(根据先前提到的Suhoza的专利的教导而制备)；比较实例C15和C16(根据先前提到的Preston的专利的教导而制备的两种制剂变体)；以及比较实例C14(根据先前提到的Hinze和Statton的专利的教导而制备)。 
重要的是，比较实例C15和C16都是固体混合物，它们提供了可能的比较参照，但是缺少本发明组合物所提供的令人满意的液态属性。实例C17即使在不存在二烷基二苯胺的情况下也表现出了少量可接受的烧焦抑制。然而，实现该结果所需的酚类的范围(94.7%)完全位于本发明的范围之外。通常，最佳组合物由烷基-HQ衍生物、二烷基-二苯胺、酚类混合物以及PTZ组成，实施范围为0.5-0.7。 
评估结构变化对对苯二酚的影响。除了优选的2,5-二-叔-戊基-对苯二酚(DTAHQ)之外，还比较了：对苯二酚(HQ)(实例12)、二-叔-丁基-对苯二酚(DTBHQ)(实例10)以及二氯二羟基蒽醌(DCDAQ)(实例12)。显然，对苯二酚环上的烷基取代(DTAHQ,DCBHQ)(实例1-9；实例10)，相对于未取代(HQ)(实例11)或对照改善了烧焦性能。另外，发现氯化取代(DCDAQ)(实例12)，尽管提供了可接受的ΔE比较值，但是导致不可接受的变色。 
因此，仅通过基于具体范围内的本发明的三组分体系来制备烧焦抑制剂组合物，能实现令人惊奇的有效烧焦抑制，而无上文所提到的缺点。 
表1 
Figure BDA00002142053700051
Figure BDA00002142053700061
*对照实施例K还含有9%稀释油Uninap 100SD和0.68%亚磷酸三异癸酯 
表2 
  实施例#   C13   C14   C15   C16   C17
  原料          
  DTAHQ   22.5         4.59
  HQ       80   20  
  DTBHQ          
  DCDAQ          
  DOHQ          
  DPA   67.5   33.1      
  DPA2       20   80  
  酚1           18.12
  酚2     66.2       54.9
  酚3           21.68
  PTZ   1   0.7       0.72
           
  dE Ex/dE K   1.16   0.81   0.85   1.18   0.72
原料列表 
DTAHQ    2,5-二-叔-戊基-对苯二酚 
HQ       对苯二酚 
DTBHQ    二-叔-丁基-对苯二酚 
DCDAQ    二氯二羟基蒽醌(dichlorodihydroxyanthroquinone) 
DPA      二异丁烯和二苯胺，CAS登记号68411-46-1或烷基化二苯 
         胺和有机磷化合物(NJTSR号01023400-5083P)以及二苯 
         胺的混合物 
DPA2     苯乙烯和2,4,4三甲基戊烯以及二苯胺，产生4,4’-双(α,α- 
         二甲基苄基)二苯胺与其他烷基化和苯乙烯化衍生物(SL) 
         的混合物：CAS 68921-45-9 
酚1      四[亚甲基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯]甲烷 
酚2      异-辛基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯 
酚3      异十三烷基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯 
PTZ      吩噻嗪 。 

Claims (8)

1.用于聚氨酯泡沫的液态烧焦抑制剂组合物，包含：
(a)约60%至80%重量比的一种或多种衍生的酚类化合物；
(b)约15%至35%重量比的一种或多种液态形式的芳香胺；
(c)约4%至8%重量比的烷基取代的对苯二酚；以及
(d)0%至约1.0%重量比的吩噻嗪。
2.如权利要求1所述的组合物，其中所述衍生的酚类化合物选自四[亚甲基(3,5-二-叔-丁基-4-羟基氢化肉桂酸酯)]甲烷；异-辛基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯；异十三烷基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯；十八烷基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯；2,6二-叔-丁基-4-壬基苯酚；1,2-双(3,5-二-叔-丁基-4-羟基氢化肉桂酰基)肼；2,2’-硫代二亚乙基双[3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯；在第4位被脂肪族、芳香族或脂肪族-芳香族部分取代的且任选具有杂原子O、N、S和P的组合的(2,6-二-叔-丁基)苯酚；以及它们的混合物。
3.如权利要求2所述的组合物，其中所述衍生的酚类化合物包含：(i)四[亚甲基(3,5-二-叔-丁基-4-羟基氢化肉桂酸酯)]甲烷；(ii)异-辛基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯；以及(iii)异十三烷基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯的组合中的一种或多种。
4.如权利要求1所述的组合物，其中所述芳香胺是：(a)二异丁烯与二苯胺的反应产物(CAS登记号68411-46-1)，以及(b)4,4’-二(α,α-二甲基苄基)二苯胺)的之一或二者。
5.如权利要求1所述的组合物，其中所述烷基取代的对苯二酚选自2,5-二-叔-戊基-对苯二酚和二-叔-丁基-对苯二酚。
6.如权利要求5所述的组合物，其中所述烷基取代的对苯二酚是2,5-二-叔-戊基-对苯二酚。
7.如权利要求1所述的组合物，其中：
(a)是四[亚甲基(3,5-二-叔-丁基-4-羟基氢化肉桂酸酯)]甲烷、异-辛基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯以及异十三烷基-3-(3,5-二-叔-丁基-4-羟苯基)丙酸酯中的一种或多种；
(b)是二异丁烯与二苯胺的反应产物；
(c)是2,5-二-叔-戊基-对苯二酚；以及
(d)存在吩噻嗪。
8.聚氨酯泡沫组合物，其包含每100份多元醇的约0.10至0.75份权利要求1所述组合物。
CN2010800654710A 2010-03-18 2010-09-23 聚氨酯泡沫烧焦抑制剂 Pending CN102834446A (zh)

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